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A striking blend of modern design and timeless barn-inspired architecture, this exceptional 4,250 SF home sits privately on 12.77 acres and offers a rare sense of space, light, and tranquility. Built in 2022, the residence still feels brand new, with 5 BD, 4 BA, and 1 half bath over 3 levels, including a legal accessory apartment. A dramatic two-story foyer sets the tone, showcasing a split staircase w/sleek stainless-steel cabling and an open balcony above. The ML is defined by soaring 9-foot ceilings, reclaimed wood beams, wide-plank white oak floors, and expansive windows and doors that invite natural light into every corner. The open-concept design seamlessly connects the great room to a chef's kitchen outfitted w/premium stainless-steel appliances, a waterfall island & bright breakfast area. The adjoining dining room, anchored by a floor-to-ceiling stone fireplace and access to a side patio, offers flexibility as either a formal gathering space or a relaxed family room. A music room w/tray ceiling provides an ideal setting for a home office or formal dining space. 1st floor primary suite is a private retreat, complete with dual walk-in closets and a spa-like bath featuring a soaking tub and walk-in shower. A powder room & expansive mudroom w/custom cabinetry connect effortlessly to the attached two-car garage, crowned w/a classic cupola. The UL continues to impress with a well-balanced layout. BDRM#2 enjoys an ensuite bath, while BDRMS #3 and #4 share a full BA.

5 Beds ⋅ 5 Baths ⋅ 24153961 MLS

A striking blend of modern design and timeless barn-inspired architecture, this exceptional 4,250 SF home sits privately on 12.77 acres and offers a rare sense of space, light, and tranquility. Built in 2022, the residence still feels brand new, with 5 BD, 4 BA, and 1 half bath over 3 levels, including a legal accessory apartment. A dramatic two-story foyer sets the tone, showcasing a split staircase w/sleek stainless-steel cabling and an open balcony above. The ML is defined by soaring 9-foot ceilings, reclaimed wood beams, wide-plank white oak floors, and expansive windows and doors that invite natural light into every corner. The open-concept design seamlessly connects the great room to a chef's kitchen outfitted w/premium stainless-steel appliances, a waterfall island & bright breakfast area. The adjoining dining room, anchored by a floor-to-ceiling stone fireplace and access to a side patio, offers flexibility as either a formal gathering space or a relaxed family room. A music room w/tray ceiling provides an ideal setting for a home office or formal dining space. 1st floor primary suite is a private retreat, complete with dual walk-in closets and a spa-like bath featuring a soaking tub and walk-in shower. A powder room & expansive mudroom w/custom cabinetry connect effortlessly to the attached two-car garage, crowned w/a classic cupola. The UL continues to impress with a well-balanced layout. BDRM#2 enjoys an ensuite bath, while BDRMS #3 and #4 share a full BA.

5 Upland Pastures Rd, Sherman

$1,700,000

Majestic Sail Harbour Home, in this premier Candlewood Lake community, on 2 sprawling, level acres has it all! Elegant 2 story marble foyer w/circular stair welcomes you, flanked by a formal living & dining room in this classic plan. An expansive kitchen w/bay dining area, offers open views of the family room, tiled 4 season sunroom, in ground pool & masterfully created gardens. A grand primary suite offers an expansive walk-in closet with additional attic storage beyond, a newly updated spa bath & ultimate privacy. A secluded guest suite, accessible by a back staircase, offers multiple closets & a full bath. Two more, well appointed bedrooms share an updated full bath w/ double sinks. ideal space for family & guests alike. A super plus is found in the 3rd floor game room with media center, pool table & more! The glorious, light filled sunroom and adjacent Rutt Kitchen offers a modern take on this classic home. Light, bright, airy and renovated this hime is an exceptional find in this private lake community. Relax & enjoy idyllic & picturesque gardens, surrounding a 42 ft Gunite pool & spa, private dock at community marina (already paid for the season), a game of tennis or pickleball at the community courts & sunbathe at the private sand beach & clubhouse! Just 70-75 minutes to New York city yet a world apart. Enjoy lake living at its finest in Candlewood Lake's premier community of Sail Harbour. Come for a visit ....stay for a lifetime!

4 Beds ⋅ 4 Baths ⋅ 24161436 MLS

Majestic Sail Harbour Home, in this premier Candlewood Lake community, on 2 sprawling, level acres has it all! Elegant 2 story marble foyer w/circular stair welcomes you, flanked by a formal living & dining room in this classic plan. An expansive kitchen w/bay dining area, offers open views of the family room, tiled 4 season sunroom, in ground pool & masterfully created gardens. A grand primary suite offers an expansive walk-in closet with additional attic storage beyond, a newly updated spa bath & ultimate privacy. A secluded guest suite, accessible by a back staircase, offers multiple closets & a full bath. Two more, well appointed bedrooms share an updated full bath w/ double sinks. ideal space for family & guests alike. A super plus is found in the 3rd floor game room with media center, pool table & more! The glorious, light filled sunroom and adjacent Rutt Kitchen offers a modern take on this classic home. Light, bright, airy and renovated this hime is an exceptional find in this private lake community. Relax & enjoy idyllic & picturesque gardens, surrounding a 42 ft Gunite pool & spa, private dock at community marina (already paid for the season), a game of tennis or pickleball at the community courts & sunbathe at the private sand beach & clubhouse! Just 70-75 minutes to New York city yet a world apart. Enjoy lake living at its finest in Candlewood Lake's premier community of Sail Harbour. Come for a visit ....stay for a lifetime!

2 Sail Harbour Dr, Sherman

$1,575,000

Beautifully sited on a gentle rise, this striking Contemporary commands sweeping panoramic views of the surrounding landscape. The home overlooks the iconic Happy Acres Farm, permanently preserved by the Town of Sherman, ensuring timeless pastoral vistas. The open floor plan features three bedrooms, including a main-level primary suite, three full and two half baths, a main-level study, and a dramatic living/dining space with vaulted ceilings and a stone-faced, double-sided bio-ethanol fireplace. The sleek kitchen includes quartz countertops, bar seating, a walk-in pantry, and top-tier SS appliances. The main level's polished concrete floors and walls of oversized windows frame stunning front and rear views, filling the home with natural light. Upstairs are two en suite bedrooms with a large, shared sitting/playroom. Additional features include a walk-up attic with excellent expansion potential, radiant heat throughout the home and three-car garage, plus a separate laundry room. Outdoor living is equally inviting with an eight-person hot tub overlooking the rolling countryside and French doors opening to a covered patio with an outdoor fireplace. There is also your own golf tee! Freshly stained exteriors and newly painted interiors create an elegant, turnkey, move-in-ready residence. Ideally located just 90 minutes from Manhattan and minutes to NYC trains.

3 Beds ⋅ 5 Baths ⋅ 24150804 MLS

Beautifully sited on a gentle rise, this striking Contemporary commands sweeping panoramic views of the surrounding landscape. The home overlooks the iconic Happy Acres Farm, permanently preserved by the Town of Sherman, ensuring timeless pastoral vistas. The open floor plan features three bedrooms, including a main-level primary suite, three full and two half baths, a main-level study, and a dramatic living/dining space with vaulted ceilings and a stone-faced, double-sided bio-ethanol fireplace. The sleek kitchen includes quartz countertops, bar seating, a walk-in pantry, and top-tier SS appliances. The main level's polished concrete floors and walls of oversized windows frame stunning front and rear views, filling the home with natural light. Upstairs are two en suite bedrooms with a large, shared sitting/playroom. Additional features include a walk-up attic with excellent expansion potential, radiant heat throughout the home and three-car garage, plus a separate laundry room. Outdoor living is equally inviting with an eight-person hot tub overlooking the rolling countryside and French doors opening to a covered patio with an outdoor fireplace. There is also your own golf tee! Freshly stained exteriors and newly painted interiors create an elegant, turnkey, move-in-ready residence. Ideally located just 90 minutes from Manhattan and minutes to NYC trains.

105 Rte 39 N, Sherman

$1,518,000

New construction 5 bedroom 4.5 bath modern farmhouse colonial in gated upscale golf community. River Oaks offers private 18 hole golf course under new ownership. Lots of upgrades to the clubhouse, restaurand/bar, and the course. River Oaks also has a community pool and tennis courts. The custom home has 2 primary bedrooms, one on the main level and one upstairs. 3 car attcahed garage. 9 Ft ceilings. Efficient propane fired heat and central air. 4 inch select red oak hardwod floors throughout. Amazing center island kitchen with quartz counters. Fireplace. Awesome versatile layout with large rooms and gathering space. This is an amazing lovel lot with pond, mountain and golf course views. Farmhouse front porch with metal roof. Even more potential in the walkout lower level that opens to huge patio. Still time to customize some things so hurry!!

5 Beds ⋅ 5 Baths ⋅ 24173967 MLS

New construction 5 bedroom 4.5 bath modern farmhouse colonial in gated upscale golf community. River Oaks offers private 18 hole golf course under new ownership. Lots of upgrades to the clubhouse, restaurand/bar, and the course. River Oaks also has a community pool and tennis courts. The custom home has 2 primary bedrooms, one on the main level and one upstairs. 3 car attcahed garage. 9 Ft ceilings. Efficient propane fired heat and central air. 4 inch select red oak hardwod floors throughout. Amazing center island kitchen with quartz counters. Fireplace. Awesome versatile layout with large rooms and gathering space. This is an amazing lovel lot with pond, mountain and golf course views. Farmhouse front porch with metal roof. Even more potential in the walkout lower level that opens to huge patio. Still time to customize some things so hurry!!

4 Pond View Ln, Sherman

$1,295,000

Welcome home to this exceptionally beautiful modern ranch style property, in a gated community and on one of the areas most elite 18 hole Golf Courses. This sprawling 4 bedroom, 3121 sq. ft. floorplan, on one level and located in the Sherman River Oaks Golf Course, is all you will ever need for family, entertainment and quality living. (whether weekend or year round) Enjoy the beautiful scenery from you covered back porch while having your morning coffee or evening delights!! Quality throughout! Hardwood floors. Center island kitchen with stainless appliances and premium choice modern cabinetry. Large vaulted living room with fireplace. Master bedroom has 2 walk in closets, a beautiful bathroom with rain head shower and sliders out to the huge deck overlooking the course. Spacious and bright bedrooms and 2 other full baths. 3.5 baths total. 3 car attached garage with high ceilings. Huge unfinished walkout lower level, roughed for future bathroom and plenty of extra additions. Beautiful views from every room in the house. Paved driveway and nicely landscaped. There is also an optional membership for the clubhouse/golf course amenities which includes use of restaurant, pool, tennis, workout room and terrace.(Under new management). And different tier options for golf. 10 minutes to the New York border on Rt. 55 and right on the Housatonic River! Just under two hours from New York City and minutes from boating on Candlewood Lake. Look no further!!

4 Beds ⋅ 4 Baths ⋅ 24148218 MLS

Welcome home to this exceptionally beautiful modern ranch style property, in a gated community and on one of the areas most elite 18 hole Golf Courses. This sprawling 4 bedroom, 3121 sq. ft. floorplan, on one level and located in the Sherman River Oaks Golf Course, is all you will ever need for family, entertainment and quality living. (whether weekend or year round) Enjoy the beautiful scenery from you covered back porch while having your morning coffee or evening delights!! Quality throughout! Hardwood floors. Center island kitchen with stainless appliances and premium choice modern cabinetry. Large vaulted living room with fireplace. Master bedroom has 2 walk in closets, a beautiful bathroom with rain head shower and sliders out to the huge deck overlooking the course. Spacious and bright bedrooms and 2 other full baths. 3.5 baths total. 3 car attached garage with high ceilings. Huge unfinished walkout lower level, roughed for future bathroom and plenty of extra additions. Beautiful views from every room in the house. Paved driveway and nicely landscaped. There is also an optional membership for the clubhouse/golf course amenities which includes use of restaurant, pool, tennis, workout room and terrace.(Under new management). And different tier options for golf. 10 minutes to the New York border on Rt. 55 and right on the Housatonic River! Just under two hours from New York City and minutes from boating on Candlewood Lake. Look no further!!

32 Long River Rd, Sherman

$1,290,000

A rare opportunity to own a private 3.70-acre retreat in Sherman-set back from the road down a scenic driveway, with a stand out one-of-a-kind oversized six car garage which easily adapts for, car collections, workspace, or recreational needs. Sherman is known for its low taxes, located just 90 minutes from NYC, this property delivers the ideal balance of privacy and convenience. A welcoming columned entry opens to bright, versatile living spaces designed for today's lifestyle, anchored by an oversized great room with vaulted ceilings-perfect for everyday living or entertaining. Hardwood floors span the main level, which features a large open-plan kitchen with casual dining, and a dining room for more formal gatherings, and deck access from kitchen-creating effortless indoor-outdoor flow. Just off the great room a substantial studio/workshop offers exceptional space for hobbies, home office/schooling or running a business. The main-level primary suite includes a remodeled bath, private deck access, and a walk-in cedar closet. Upstairs, a spacious multi-room second primary suite is complemented by two additional bedrooms-one with multiple flexible spaces-ideal for family or guests. . The large basement offers great storage. Outdoors, enjoy the expansive grounds, greenhouse, firepit area it is ready for your customized retreat.maybe a pool or tennis/pickleball court. Over $115,000 in recent improvements, whole-house generator and smart technology add true value.

4 Beds ⋅ 4 Baths ⋅ 24171840 MLS

A rare opportunity to own a private 3.70-acre retreat in Sherman-set back from the road down a scenic driveway, with a stand out one-of-a-kind oversized six car garage which easily adapts for, car collections, workspace, or recreational needs. Sherman is known for its low taxes, located just 90 minutes from NYC, this property delivers the ideal balance of privacy and convenience. A welcoming columned entry opens to bright, versatile living spaces designed for today's lifestyle, anchored by an oversized great room with vaulted ceilings-perfect for everyday living or entertaining. Hardwood floors span the main level, which features a large open-plan kitchen with casual dining, and a dining room for more formal gatherings, and deck access from kitchen-creating effortless indoor-outdoor flow. Just off the great room a substantial studio/workshop offers exceptional space for hobbies, home office/schooling or running a business. The main-level primary suite includes a remodeled bath, private deck access, and a walk-in cedar closet. Upstairs, a spacious multi-room second primary suite is complemented by two additional bedrooms-one with multiple flexible spaces-ideal for family or guests. . The large basement offers great storage. Outdoors, enjoy the expansive grounds, greenhouse, firepit area it is ready for your customized retreat.maybe a pool or tennis/pickleball court. Over $115,000 in recent improvements, whole-house generator and smart technology add true value.

27 Smoke Ridge Dr, Sherman

$1,155,000

Welcome to 7 Anderson Hill Rd - a serene retreat set on over 7 acres of beautifully landscaped grounds, featuring specimen trees and vibrant perennial gardens that create a true sense of peace and privacy. A charming stone gravel driveway leads you to this stunning contemporary home offering 3 bedrooms, 2.5 baths, and a detached, heated 2-car garage. Inside, the dramatic two-story living room makes an immediate impression with its soaring ceilings, freestanding fireplace, and expansive walls of windows that flood the space with natural light. The cozy den provides the perfect spot to relax with a book or enjoy your favorite shows. The open-concept kitchen flows seamlessly into the dining and living areas, making entertaining effortless. It features granite countertops, slate floors, a double wall oven, electric cooktop, dishwasher, and abundant windows that add warmth and character. The dining room, with its wide-plank hardwood floors and wall of windows, is ideal for hosting or simply enjoying your morning coffee while overlooking the scenic property. Upstairs, you'll find two generously sized bedrooms, an oversized walk-in closet, and a shared full bath. The private primary suite is thoughtfully set apart, offering its own fireplace, a large walk-in closet, full bath, and a tranquil private deck nestled among the trees-perfect for starting your day in nature. The finished basement provides valuable additional living space and includes a California walk-in closet.

3 Beds ⋅ 3 Baths ⋅ 24161160 MLS

Welcome to 7 Anderson Hill Rd - a serene retreat set on over 7 acres of beautifully landscaped grounds, featuring specimen trees and vibrant perennial gardens that create a true sense of peace and privacy. A charming stone gravel driveway leads you to this stunning contemporary home offering 3 bedrooms, 2.5 baths, and a detached, heated 2-car garage. Inside, the dramatic two-story living room makes an immediate impression with its soaring ceilings, freestanding fireplace, and expansive walls of windows that flood the space with natural light. The cozy den provides the perfect spot to relax with a book or enjoy your favorite shows. The open-concept kitchen flows seamlessly into the dining and living areas, making entertaining effortless. It features granite countertops, slate floors, a double wall oven, electric cooktop, dishwasher, and abundant windows that add warmth and character. The dining room, with its wide-plank hardwood floors and wall of windows, is ideal for hosting or simply enjoying your morning coffee while overlooking the scenic property. Upstairs, you'll find two generously sized bedrooms, an oversized walk-in closet, and a shared full bath. The private primary suite is thoughtfully set apart, offering its own fireplace, a large walk-in closet, full bath, and a tranquil private deck nestled among the trees-perfect for starting your day in nature. The finished basement provides valuable additional living space and includes a California walk-in closet.

7 Anderson Rd E, Sherman

$1,050,000

Mid-Century Modern Ranch on 4.4 Private Acres in Sherman, CT. Minutes from town center and Candlewood Lake, and just a scenic 90-minute drive from NYC. This one-of-a-kind home delivers style, privacy and serious entertaining space. A newly renovated kitchen (2023) features Bertazzoni appliances, Moroccan terrazzo flooring and leather-finished granite counters. The primary suite offers a fireplace and spa-like bath with heated terrazzo floors, heated towel rack, Kohler double vanity and deep soaking tub. A sun-filled living room and foyer anchor the home, flowing to the primary suite on one side and 2-3 additional bedrooms on the other for guest privacy. Outdoor living shines with a screened porch outfitted with a Forza Forni stucco wood-fired pizza oven and stainless outdoor kitchen workbench, plus a resurfaced gunite saltwater pool (2022). A 720 SF workshop/studio/party barn with 3 skylights and epoxy floors, adds year-round flexibility for work or play. The park-like grounds include dwarf peach and apple trees, kousa dogwood, blackberry and raspberry patches, and abundant wild mushroom foraging: morels, chanterelles, and golden oysters. Recent updates: New roof (2019), full home generator (2019), new oil tank (2019), porch re-screen (2021), repainted exterior & new gutters (2024).

3 Beds ⋅ 2 Baths ⋅ 24196377 MLS

Mid-Century Modern Ranch on 4.4 Private Acres in Sherman, CT. Minutes from town center and Candlewood Lake, and just a scenic 90-minute drive from NYC. This one-of-a-kind home delivers style, privacy and serious entertaining space. A newly renovated kitchen (2023) features Bertazzoni appliances, Moroccan terrazzo flooring and leather-finished granite counters. The primary suite offers a fireplace and spa-like bath with heated terrazzo floors, heated towel rack, Kohler double vanity and deep soaking tub. A sun-filled living room and foyer anchor the home, flowing to the primary suite on one side and 2-3 additional bedrooms on the other for guest privacy. Outdoor living shines with a screened porch outfitted with a Forza Forni stucco wood-fired pizza oven and stainless outdoor kitchen workbench, plus a resurfaced gunite saltwater pool (2022). A 720 SF workshop/studio/party barn with 3 skylights and epoxy floors, adds year-round flexibility for work or play. The park-like grounds include dwarf peach and apple trees, kousa dogwood, blackberry and raspberry patches, and abundant wild mushroom foraging: morels, chanterelles, and golden oysters. Recent updates: New roof (2019), full home generator (2019), new oil tank (2019), porch re-screen (2021), repainted exterior & new gutters (2024).

15 Brinsmade Ln, Sherman

$960,000

Hard to find direct waterfront cottage on a small pristine spring fed lake. Green Pond also known as Emerald Lake is widely regarded as one of the cleanest natural waters in Ct. Additionally, this property is in a gated community and has access to 2 beaches on Candlewood Lake. The 2 bedroom 3 full bath home has amazing lake views and is light and bright with lots of character. Fireplace. Hardwood floors. Central air. Unique land with lots of rock outcroppings. Lots of decking to entertain while enjoying the tranquil lake views. There is a winding path down to the gazebo and your own private dock. Over 200 feet of direct water frontage. Green Pond is a 30 acre lake with no motor boats. Amazing swimming, canoeing, paddle boarding, etc. 2 year old septic. This is a unique offering!!

2 Beds ⋅ 3 Baths ⋅ 24192148 MLS

Hard to find direct waterfront cottage on a small pristine spring fed lake. Green Pond also known as Emerald Lake is widely regarded as one of the cleanest natural waters in Ct. Additionally, this property is in a gated community and has access to 2 beaches on Candlewood Lake. The 2 bedroom 3 full bath home has amazing lake views and is light and bright with lots of character. Fireplace. Hardwood floors. Central air. Unique land with lots of rock outcroppings. Lots of decking to entertain while enjoying the tranquil lake views. There is a winding path down to the gazebo and your own private dock. Over 200 feet of direct water frontage. Green Pond is a 30 acre lake with no motor boats. Amazing swimming, canoeing, paddle boarding, etc. 2 year old septic. This is a unique offering!!

153 Green Pond Rd, Sherman

$930,000

Nestled on a quiet cul-de-sac in the highly desirable Sherman subdivision, this beautifully remodeled country contemporary offers over 2,700 square feet of inviting living space. Designed to capture natural light, the home features an open floor plan with dramatic floor-to-ceiling windows and stunning views of Happy Acres Farm, delivering breathtaking sunsets every evening. At the heart of the home is a striking floor-to-ceiling fieldstone fireplace, perfectly complementing the warm and airy interior. Two sets of sliding doors lead to a spacious deck, ideal for relaxing or entertaining while overlooking the private, park-like yard. The upper level boasts a serene primary suite with vaulted ceilings, skylights, and a tastefully updated en-suite bath. Two additional bedrooms and a versatile home office, easily adaptable for overnight guests, and supported by the four-bedroom septic, complete this level. The lower level offers a generous recreation room, with luxury vinyl flooring, perfect for gatherings and play, along with a workshop, ample storage, and additional garage space. Surrounded by mature trees and perennial gardens, the property provides exceptional privacy in a picturesque setting. Conveniently located just minutes from schools, shopping, dining, and recreational amenities including walking tracks, tennis courts, and Sherman Town Beach on Candlewood Lake. Commuters will appreciate easy access to nearby Metro-North trains, all while benefiting from low taxes, too!

3 Beds ⋅ 3 Baths ⋅ 24161255 MLS

Nestled on a quiet cul-de-sac in the highly desirable Sherman subdivision, this beautifully remodeled country contemporary offers over 2,700 square feet of inviting living space. Designed to capture natural light, the home features an open floor plan with dramatic floor-to-ceiling windows and stunning views of Happy Acres Farm, delivering breathtaking sunsets every evening. At the heart of the home is a striking floor-to-ceiling fieldstone fireplace, perfectly complementing the warm and airy interior. Two sets of sliding doors lead to a spacious deck, ideal for relaxing or entertaining while overlooking the private, park-like yard. The upper level boasts a serene primary suite with vaulted ceilings, skylights, and a tastefully updated en-suite bath. Two additional bedrooms and a versatile home office, easily adaptable for overnight guests, and supported by the four-bedroom septic, complete this level. The lower level offers a generous recreation room, with luxury vinyl flooring, perfect for gatherings and play, along with a workshop, ample storage, and additional garage space. Surrounded by mature trees and perennial gardens, the property provides exceptional privacy in a picturesque setting. Conveniently located just minutes from schools, shopping, dining, and recreational amenities including walking tracks, tennis courts, and Sherman Town Beach on Candlewood Lake. Commuters will appreciate easy access to nearby Metro-North trains, all while benefiting from low taxes, too!

29 Farm Rd, Sherman

$925,000

Impeccably maintained home in desirable Southern Sherman on 3.8 private, flat acres, right along the CT/ NY border. Welcome to 2 Hollow Brook Road! A rare find where every major mechanical, structural and cosmetic update has already been expertly handled. Truly turn-key and ready for its next chapter. This meticulously updated home blends smart infrastructure with a resort-style backyard. Inside find fresh paint, new interior doors and a stunning chef's kitchen with premium GE Cafe appliances. The primary suite is a true sanctuary with new hardwood floors, a completely remodeled spa-like bath with a walk-in glass shower, spacious walk-in closet and a large office that could also be used as a dressing room. Upstairs features new carpets while the finished basement boasts a private 5th bedroom with full bath - 600 SF of space that could also function as an in-law suite, gym or playroom. Outside is an entertainer's dream: a bluestone patio with a built-in grill, heated salt water pool with new LED lighting and a Sundance hot tub, all framed by professional landscaping & irrigation. Mechanicals are top-tier: 2-year-old roof & solar system, 5 new ductless mini-splits, Nest-controlled heating, epoxy-floor garage, constant-pressure well pump, UV water system and a whole-home alarm. There is nothing left to do but move in and enjoy your private country oasis! Sherman boasts a town beach on Candlewood Lake with boat slips. Easy commutes: 45 min to White Plains, 60 miles to NYC.

5 Beds ⋅ 4 Baths ⋅ 24183159 MLS

Impeccably maintained home in desirable Southern Sherman on 3.8 private, flat acres, right along the CT/ NY border. Welcome to 2 Hollow Brook Road! A rare find where every major mechanical, structural and cosmetic update has already been expertly handled. Truly turn-key and ready for its next chapter. This meticulously updated home blends smart infrastructure with a resort-style backyard. Inside find fresh paint, new interior doors and a stunning chef's kitchen with premium GE Cafe appliances. The primary suite is a true sanctuary with new hardwood floors, a completely remodeled spa-like bath with a walk-in glass shower, spacious walk-in closet and a large office that could also be used as a dressing room. Upstairs features new carpets while the finished basement boasts a private 5th bedroom with full bath - 600 SF of space that could also function as an in-law suite, gym or playroom. Outside is an entertainer's dream: a bluestone patio with a built-in grill, heated salt water pool with new LED lighting and a Sundance hot tub, all framed by professional landscaping & irrigation. Mechanicals are top-tier: 2-year-old roof & solar system, 5 new ductless mini-splits, Nest-controlled heating, epoxy-floor garage, constant-pressure well pump, UV water system and a whole-home alarm. There is nothing left to do but move in and enjoy your private country oasis! Sherman boasts a town beach on Candlewood Lake with boat slips. Easy commutes: 45 min to White Plains, 60 miles to NYC.

2 Hollow Brook Rd, Sherman

$922,500

A spacious contemporary located in a resort quality setting. Located above the fairway of the 13th hole of the Club at River Oaks, an 18 hole golf course masterfully designed around the meandering contours of the Housatonic River on beautifully rolling farmland. The home site boasts mountain valley and seasonal river views and is equipped with a heated gunite, infinity edge pool with attached gunite spa & waterfall, designed and constructed by award winning Dobson Pool Co. The home design features a first floor primary suite, flowing and open floorplan combining the living and dining areas with cathedral ceilings. The walls of glass seamlessly connecting the interior and exterior spaces while inviting the surrounding viewscapes into the home. The lower level provides a large family with a second wood burning fireplace, a separate laundry room, and access to two additional private bedrooms, two full baths, all with walk-out french door access to expansive stone terraces, pool, spa and recreation and entertaining areas.

3 Beds ⋅ 4 Baths ⋅ 24157144 MLS

A spacious contemporary located in a resort quality setting. Located above the fairway of the 13th hole of the Club at River Oaks, an 18 hole golf course masterfully designed around the meandering contours of the Housatonic River on beautifully rolling farmland. The home site boasts mountain valley and seasonal river views and is equipped with a heated gunite, infinity edge pool with attached gunite spa & waterfall, designed and constructed by award winning Dobson Pool Co. The home design features a first floor primary suite, flowing and open floorplan combining the living and dining areas with cathedral ceilings. The walls of glass seamlessly connecting the interior and exterior spaces while inviting the surrounding viewscapes into the home. The lower level provides a large family with a second wood burning fireplace, a separate laundry room, and access to two additional private bedrooms, two full baths, all with walk-out french door access to expansive stone terraces, pool, spa and recreation and entertaining areas.

6 River Bend Ln, Sherman

$915,000

Welcome to this impeccably remodeled, three-bedroom, three-bath turn-key home, boasting architectural spaces, trendy colors and sophisticated finishes. Custom millwork and wide plank hardwood floors add tons of style throughout. Designed with a flexible layout and generous entertaining spaces featuring walls of windows, vaulted ceilings and a wood burning stone fireplace in the living room. The kitchen is a chef's dream, with high end appliances and opens directly to the dining area. A bonus loft space is 'cute perfection' and could easily be used for guests / home office / den / arts & crafts. Each of the 3 bathrooms have been thoughtfully and meticulously presented with gorgeous, stylish tiling. The 3 bedrooms have generous closets, naturally. A huge deck is perfect for al fresco dining overlooking a serene, nature-filled yard filled with landscaped plantings. The garage is connected to the basement with ample storage. Nestled close to the tranquil Timber Trails and offering access to Sherman's town beach on Candlewood Lake, this home is a perfect escape. Sherman's quaint town center is nearby with shops, sports fields, tennis courts etc. Commuting is a breeze with easy access to Rte 37 placing you just 90 minutes from Manhattan or 20 mins to Metro North Trains. This is a MUST SEE property!

2 Beds ⋅ 3 Baths ⋅ 24132328 MLS

Welcome to this impeccably remodeled, three-bedroom, three-bath turn-key home, boasting architectural spaces, trendy colors and sophisticated finishes. Custom millwork and wide plank hardwood floors add tons of style throughout. Designed with a flexible layout and generous entertaining spaces featuring walls of windows, vaulted ceilings and a wood burning stone fireplace in the living room. The kitchen is a chef's dream, with high end appliances and opens directly to the dining area. A bonus loft space is 'cute perfection' and could easily be used for guests / home office / den / arts & crafts. Each of the 3 bathrooms have been thoughtfully and meticulously presented with gorgeous, stylish tiling. The 3 bedrooms have generous closets, naturally. A huge deck is perfect for al fresco dining overlooking a serene, nature-filled yard filled with landscaped plantings. The garage is connected to the basement with ample storage. Nestled close to the tranquil Timber Trails and offering access to Sherman's town beach on Candlewood Lake, this home is a perfect escape. Sherman's quaint town center is nearby with shops, sports fields, tennis courts etc. Commuting is a breeze with easy access to Rte 37 placing you just 90 minutes from Manhattan or 20 mins to Metro North Trains. This is a MUST SEE property!

45 Big Trl, Sherman

$850,000

This 4-Bedroom/3-Bath Contemporary Ranch is privately set in desirable southern Sherman, bordering six acres of protected open space and offering a blend of comfort, style, and the convenience of single-level living. Surrounded by nature on a fully usable 2-acre property, the home's inviting L-shaped design fills the interior with natural light while seamlessly connecting indoor living spaces to the outdoors. At the heart of the property is a beautiful heated gunite pool with elegant fieldstone surround, complemented by lush perennial gardens, a fenced one-acre backyard, and expansive lawn areas ideal for recreation or entertaining. Inside, the spacious layout features bright and airy living and dining rooms, along with a large family room enhanced by heated tile flooring and one of two fireplaces. Maple hardwood floors run throughout the main level, adding warmth and continuity. The home offers two primary bedroom suites, including one in the finished walkout lower level-perfect for guests, extended family, or an in-law arrangement. The lower level provides approximately 1,600 square feet of finished space, offering flexibility for recreation, home office, fitness, or private guest quarters. The home underwent a full renovation in 2004, was stylishly remodeled in 2013, and many recent upgrades since. Ideally located in southern Sherman, this easy-living property offers privacy and tranquility while remaining highly convenient for commuters.

4 Beds ⋅ 3 Baths ⋅ 24172237 MLS

This 4-Bedroom/3-Bath Contemporary Ranch is privately set in desirable southern Sherman, bordering six acres of protected open space and offering a blend of comfort, style, and the convenience of single-level living. Surrounded by nature on a fully usable 2-acre property, the home's inviting L-shaped design fills the interior with natural light while seamlessly connecting indoor living spaces to the outdoors. At the heart of the property is a beautiful heated gunite pool with elegant fieldstone surround, complemented by lush perennial gardens, a fenced one-acre backyard, and expansive lawn areas ideal for recreation or entertaining. Inside, the spacious layout features bright and airy living and dining rooms, along with a large family room enhanced by heated tile flooring and one of two fireplaces. Maple hardwood floors run throughout the main level, adding warmth and continuity. The home offers two primary bedroom suites, including one in the finished walkout lower level-perfect for guests, extended family, or an in-law arrangement. The lower level provides approximately 1,600 square feet of finished space, offering flexibility for recreation, home office, fitness, or private guest quarters. The home underwent a full renovation in 2004, was stylishly remodeled in 2013, and many recent upgrades since. Ideally located in southern Sherman, this easy-living property offers privacy and tranquility while remaining highly convenient for commuters.

12 Mauweehoo Hl, Sherman

$830,000

Welcome to this Contemporary masterpiece nestled in the serene town of Sherman, CT. The home boasts incredible curb appeal with crisp white architectural siding, bold dark-trimmed windows, a grand stone-accented entryway, and a spacious attached 2-car garage. Step inside to discover a bright, beautifully updated interior anchored by a massive, sun-drenched living area. the fluid, open-concept floor plan features a magnificent floor-to-ceiling fieldstone fireplace with a raised hearth, pristine gleaming hardwood floors, and seamless transitions into the main living spaces. Large sliding glass doors lead to a private back deck, perfect for indoor-outdoor entertaining. The heart of the home is the chef's kitchen, seamlessly connected to the living room, featuring an expansive quartz island with casual seating, custom white cabinetry with modern black hardware, premium stainless steel appliances, and a stunning tile backsplash. Offering 4 spacious bedrooms, 4 bathrooms, and fluid open-concept living spaces, this home perfectly blends modern luxury with everyday functionality. Situated on a private lot in a highly desirable neighborhood, this turnkey property is ready to welcome its next owners.

4 Beds ⋅ 3 Baths ⋅ 24192388 MLS

Welcome to this Contemporary masterpiece nestled in the serene town of Sherman, CT. The home boasts incredible curb appeal with crisp white architectural siding, bold dark-trimmed windows, a grand stone-accented entryway, and a spacious attached 2-car garage. Step inside to discover a bright, beautifully updated interior anchored by a massive, sun-drenched living area. the fluid, open-concept floor plan features a magnificent floor-to-ceiling fieldstone fireplace with a raised hearth, pristine gleaming hardwood floors, and seamless transitions into the main living spaces. Large sliding glass doors lead to a private back deck, perfect for indoor-outdoor entertaining. The heart of the home is the chef's kitchen, seamlessly connected to the living room, featuring an expansive quartz island with casual seating, custom white cabinetry with modern black hardware, premium stainless steel appliances, and a stunning tile backsplash. Offering 4 spacious bedrooms, 4 bathrooms, and fluid open-concept living spaces, this home perfectly blends modern luxury with everyday functionality. Situated on a private lot in a highly desirable neighborhood, this turnkey property is ready to welcome its next owners.

7 Glenview Dr, Sherman

$815,000

Beautifully sited, this striking Contemporary Cape commands sweeping panoramic views of the surrounding landscape. The home overlooks the iconic Happy Acres Farm, permanently preserved by the Town of Sherman, ensuring timeless pastoral vistas. The open floor plan features three bedrooms, including a main-level primary suite, 3 full baths, main-level office, a dramatic living room space w/vaulted ceilings & a gas log fireplace. The sleek kitchen includes granite countertops, bar seating, & an abundance of cabinet space. The main level also features hdwd floors & walls of oversized windows with stunning front.side & rear views, filling the home with natural light. The upstairs en suite bdrm can also be used as a sitting/playroom & guest quarters or primary bdrm suite. Additional features include a 2.5 car garage, full bsmt just waiting to be finished. Outdoor living is equally inviting with the in-ground pool overlooking the rolling countryside. A four-season sunroom leading out to a newly refurbished deck. Freshly painted exterior & interior, Gas Generac generator, newer roof, new front porch w/slider, new garage doors & front driveway, newer solar panels for energy efficiency! (See Features Sheet for more updates) Enjoy the charm & tranquility of Sherman with beach rights to picturesque Candlewood Lake. Ideally located just 90 minutes from Manhattan & min to NYC train. Come experience the exceptional beauty & peaceful views this special home has to offer!

3 Beds ⋅ 3 Baths ⋅ 24160344 MLS

Beautifully sited, this striking Contemporary Cape commands sweeping panoramic views of the surrounding landscape. The home overlooks the iconic Happy Acres Farm, permanently preserved by the Town of Sherman, ensuring timeless pastoral vistas. The open floor plan features three bedrooms, including a main-level primary suite, 3 full baths, main-level office, a dramatic living room space w/vaulted ceilings & a gas log fireplace. The sleek kitchen includes granite countertops, bar seating, & an abundance of cabinet space. The main level also features hdwd floors & walls of oversized windows with stunning front.side & rear views, filling the home with natural light. The upstairs en suite bdrm can also be used as a sitting/playroom & guest quarters or primary bdrm suite. Additional features include a 2.5 car garage, full bsmt just waiting to be finished. Outdoor living is equally inviting with the in-ground pool overlooking the rolling countryside. A four-season sunroom leading out to a newly refurbished deck. Freshly painted exterior & interior, Gas Generac generator, newer roof, new front porch w/slider, new garage doors & front driveway, newer solar panels for energy efficiency! (See Features Sheet for more updates) Enjoy the charm & tranquility of Sherman with beach rights to picturesque Candlewood Lake. Ideally located just 90 minutes from Manhattan & min to NYC train. Come experience the exceptional beauty & peaceful views this special home has to offer!

3 Taber Rd, Sherman

$770,000

Welcome to this sprawling 5 bedroom Antique Colonial in the beautiful town of Sherman. The property invites you with many gardens, flowers and a serene coy pond. Plenty of parking for year round entertainment. Separate heated and cooled detached garage has been converted to a studio or home office. Can also be converted back to garage if that suits your needs. As you enter the large open foyer, you will see that this home has been tastefully upkept with tons of charm. Enter the newly remodeled living room with beams and beautiful fireplace to keep you nice and warm in the months of winter wonderland. Super versatile layout has option for private master bedroom wing or inlaw/au-pair on Oppposite side of the house. Tons of parking. Brand new septic. Fenced yard. Has its own well plus access to community water if necessary. Great Southern Sherman location for New York commute and directly across from large pond for row boating/fishing. This is great value and a must see. Low taxes

5 Beds ⋅ 3 Baths ⋅ 24186663 MLS

Welcome to this sprawling 5 bedroom Antique Colonial in the beautiful town of Sherman. The property invites you with many gardens, flowers and a serene coy pond. Plenty of parking for year round entertainment. Separate heated and cooled detached garage has been converted to a studio or home office. Can also be converted back to garage if that suits your needs. As you enter the large open foyer, you will see that this home has been tastefully upkept with tons of charm. Enter the newly remodeled living room with beams and beautiful fireplace to keep you nice and warm in the months of winter wonderland. Super versatile layout has option for private master bedroom wing or inlaw/au-pair on Oppposite side of the house. Tons of parking. Brand new septic. Fenced yard. Has its own well plus access to community water if necessary. Great Southern Sherman location for New York commute and directly across from large pond for row boating/fishing. This is great value and a must see. Low taxes

172 Rte 37 S, Sherman

$700,000

Welcome to 33 Skyline Dr in Sherman CT. Located at the northern end of Candlewood Lake in the gated community of Candlewood Lake Estates. Included in the sale is Boat Slip #8 located on Orchard Beach. These slips are limited and carry a value! This year round house offers privacy, wonderful views of the lake and distant mountains. Open floor plan with the living space,(Great room, Dining room, Country Kitchen and half bath) on the upper level to optimize the views and the natural light with so many windows & the vaulted ceilings. Beams & two sided stone fireplace & wide plank pine flooring enhance the rustic charm. The country kitchen is equipped with stainless steel appliances, large deep sink, granite counters, a large island, plenty of seating space & views from both sides of the room. A real pleasure for everyday living & entertaining. The Great room has access to a large deck. Also, vaulted ceilings with beams. The fireplace is a good focal point separating the Great room from the Dining room. The lower level consists of a large primary bedroom with full bath and plenty of closet space. There are two other good sized bedrooms, a laundry room and another full bath. The crawl space basement houses twin oil tanks, the electric water heater & furnace. The house does have central air / warm air heat.

3 Beds ⋅ 3 Baths ⋅ 24195001 MLS

Welcome to 33 Skyline Dr in Sherman CT. Located at the northern end of Candlewood Lake in the gated community of Candlewood Lake Estates. Included in the sale is Boat Slip #8 located on Orchard Beach. These slips are limited and carry a value! This year round house offers privacy, wonderful views of the lake and distant mountains. Open floor plan with the living space,(Great room, Dining room, Country Kitchen and half bath) on the upper level to optimize the views and the natural light with so many windows & the vaulted ceilings. Beams & two sided stone fireplace & wide plank pine flooring enhance the rustic charm. The country kitchen is equipped with stainless steel appliances, large deep sink, granite counters, a large island, plenty of seating space & views from both sides of the room. A real pleasure for everyday living & entertaining. The Great room has access to a large deck. Also, vaulted ceilings with beams. The fireplace is a good focal point separating the Great room from the Dining room. The lower level consists of a large primary bedroom with full bath and plenty of closet space. There are two other good sized bedrooms, a laundry room and another full bath. The crawl space basement houses twin oil tanks, the electric water heater & furnace. The house does have central air / warm air heat.

33 Skyline Dr, Sherman

$690,000

Golden opportunity awaits in one of Sherman's most sought-after neighborhoods. This spacious and private home is ready for your personal touch and offers exceptional potential inside and out. Featuring four generously sized bedrooms plus a versatile bonus room ideal for a gym, studio, playroom, home office, or guest space, the layout provides flexibility for today's lifestyle. The kitchen opens seamlessly to the inviting living room, where vaulted ceilings, hardwood floors, skylights, and sliding glass doors create a bright and airy atmosphere. Step outside to an expansive deck overlooking a peaceful natural setting-perfect for relaxing, entertaining, or enjoying a quiet retreat. A full unfinished basement offers even more opportunity to expand and customize the home to suit your needs. Bring your vision and make this property the home of your dreams. Just 90 minutes from New York City, it is an ideal choice for year-round living or a weekend escape.

4 Beds ⋅ 4 Baths ⋅ 24196187 MLS

Golden opportunity awaits in one of Sherman's most sought-after neighborhoods. This spacious and private home is ready for your personal touch and offers exceptional potential inside and out. Featuring four generously sized bedrooms plus a versatile bonus room ideal for a gym, studio, playroom, home office, or guest space, the layout provides flexibility for today's lifestyle. The kitchen opens seamlessly to the inviting living room, where vaulted ceilings, hardwood floors, skylights, and sliding glass doors create a bright and airy atmosphere. Step outside to an expansive deck overlooking a peaceful natural setting-perfect for relaxing, entertaining, or enjoying a quiet retreat. A full unfinished basement offers even more opportunity to expand and customize the home to suit your needs. Bring your vision and make this property the home of your dreams. Just 90 minutes from New York City, it is an ideal choice for year-round living or a weekend escape.

21 Farm Rd, Sherman

$650,000

Tucked away on a quiet cul-de-sac just 1/2 mile from the New York state line, this home offers an appealing blend of privacy and convenience on two level acres in a tranquil, natural setting. The main level features generously sized rooms, including an eat-in kitchen with sliders to an exterior deck - ideal for indoor-outdoor living. The dining room and family room flank the kitchen, with the family room offering a cozy fireplace and leading to an expansive 26' living room with a striking stone fireplace. Bright spacious interiors create inviting spaces for both everyday living and entertaining. A welcoming foyer, full bath, and combined laundry/mudroom complete the main level. Upstairs, the primary bedroom suite is accompanied by three additional bedrooms, providing ample space for family and guests. Hardwood floors and abundant natural light on the inside, and mature specimen trees and plantings on the outside, enhance the home's appeal. While the home might benefit from updates, its exceptional floor plan, peaceful setting, and prime location offer tremendous upside potential. Sherman residents enjoy access to a town park with tennis courts, jogging track, playground, and beach on Candlewood Lake. Conveniently located just 90 minutes from Manhattan and minutes to the train, this home offers the perfect balance of country charm and commuter accessibility. Subject to probate approval and offered in "as is" condition. A wonderful opportunity to make it your own.

4 Beds ⋅ 3 Baths ⋅ 24160836 MLS

Tucked away on a quiet cul-de-sac just 1/2 mile from the New York state line, this home offers an appealing blend of privacy and convenience on two level acres in a tranquil, natural setting. The main level features generously sized rooms, including an eat-in kitchen with sliders to an exterior deck - ideal for indoor-outdoor living. The dining room and family room flank the kitchen, with the family room offering a cozy fireplace and leading to an expansive 26' living room with a striking stone fireplace. Bright spacious interiors create inviting spaces for both everyday living and entertaining. A welcoming foyer, full bath, and combined laundry/mudroom complete the main level. Upstairs, the primary bedroom suite is accompanied by three additional bedrooms, providing ample space for family and guests. Hardwood floors and abundant natural light on the inside, and mature specimen trees and plantings on the outside, enhance the home's appeal. While the home might benefit from updates, its exceptional floor plan, peaceful setting, and prime location offer tremendous upside potential. Sherman residents enjoy access to a town park with tennis courts, jogging track, playground, and beach on Candlewood Lake. Conveniently located just 90 minutes from Manhattan and minutes to the train, this home offers the perfect balance of country charm and commuter accessibility. Subject to probate approval and offered in "as is" condition. A wonderful opportunity to make it your own.

12 Quaker Ridge Rd, Sherman

$630,000

Discover the perfect blend of comfort, convenience, and seasonal beauty in this privately sited ranch home with seasonal views of Candlewood Lake. Nestled within the sought-after Deer Run Shores Lake Club community, this property offers access to fantastic amenities, including a pool, clubhouse, beach area, and guest parking. This home features spray foam insulation for energy efficiency and a full-house generator for peace of mind. The main level showcases gleaming HWF, a spacious primary suite w/a full bath and access to a serene three-season room, plus two additional bedrooms and a stylish hall bath. The EIK, complete with an island, abundant cabinet storage, and counter space, flows seamlessly into the dining area with direct access to the deck-and slider to three season room. Adding to its charm, the home boasts a welcoming front porch, ideal for sipping your morning coffee or enjoying a quiet evening outdoors. The LR is a cozy retreat with a FP framed by built-ins, recessed lighting, and a wall of sliders leading to the bright three-season room. A convenient mudroom connects the two-car garage to the kitchen, making unloading groceries a breeze. The walk-out lower level offers incredible versatility with a gas fireplace, a large half bath, multiple sliders opening to the patio, two mechanical rooms, and even potential for a wine cellar. Its idyllic location, modern updates, and access to Candlewood Lake's vibrant lifestyle, this home is ready to welcome you.

3 Beds ⋅ 4 Baths ⋅ 24167078 MLS

Discover the perfect blend of comfort, convenience, and seasonal beauty in this privately sited ranch home with seasonal views of Candlewood Lake. Nestled within the sought-after Deer Run Shores Lake Club community, this property offers access to fantastic amenities, including a pool, clubhouse, beach area, and guest parking. This home features spray foam insulation for energy efficiency and a full-house generator for peace of mind. The main level showcases gleaming HWF, a spacious primary suite w/a full bath and access to a serene three-season room, plus two additional bedrooms and a stylish hall bath. The EIK, complete with an island, abundant cabinet storage, and counter space, flows seamlessly into the dining area with direct access to the deck-and slider to three season room. Adding to its charm, the home boasts a welcoming front porch, ideal for sipping your morning coffee or enjoying a quiet evening outdoors. The LR is a cozy retreat with a FP framed by built-ins, recessed lighting, and a wall of sliders leading to the bright three-season room. A convenient mudroom connects the two-car garage to the kitchen, making unloading groceries a breeze. The walk-out lower level offers incredible versatility with a gas fireplace, a large half bath, multiple sliders opening to the patio, two mechanical rooms, and even potential for a wine cellar. Its idyllic location, modern updates, and access to Candlewood Lake's vibrant lifestyle, this home is ready to welcome you.

47 Rt 39th So, Sherman

$515,000

Discover the perfect blend of timeless charm and modern sophistication in the heart of Sherman, CT. This beautifully remodeled 2-bed, 2-bath cottage offers an idyllic lifestyle, situated just minutes from the town beach on Candlewood Lake. This home's classic exterior curb appeal sets a welcoming tone for a residence brimming with character. Inside, exquisite period details have been restored to perfection, including eyebrow windows, exposed beams and rich walnut floors. A wood-burning fireplace serves as the heart of the home, creating a warm, inviting atmosphere for gatherings or quiet winter evenings. An adjoining sunroom is a bright, yet cosy place to relax, work or watch the world go by! The flexible floor plan features a separate dining room that easily converts to a main-level bedroom, perfectly adapting to your lifestyle needs. The kitchen features new, high-end s/steel appliances and a separate laundry room also houses the pantry. A full Bath completes this level. Upstairs, two bedrooms share a stylish full Bath and there is central air throughout the home. The standout highlight of this property is a separate, two-level detached artist's studio. The mezzanine floor has 360 degree views and is a perfect place to explore your creative talents. With French doors opening gracefully to a lush yard and established vegetable garden, this space serves as an inspiring retreat for arts & crafts, a workshop, home office, or a peaceful hang out space.

2 Beds ⋅ 2 Baths ⋅ 24181666 MLS

Discover the perfect blend of timeless charm and modern sophistication in the heart of Sherman, CT. This beautifully remodeled 2-bed, 2-bath cottage offers an idyllic lifestyle, situated just minutes from the town beach on Candlewood Lake. This home's classic exterior curb appeal sets a welcoming tone for a residence brimming with character. Inside, exquisite period details have been restored to perfection, including eyebrow windows, exposed beams and rich walnut floors. A wood-burning fireplace serves as the heart of the home, creating a warm, inviting atmosphere for gatherings or quiet winter evenings. An adjoining sunroom is a bright, yet cosy place to relax, work or watch the world go by! The flexible floor plan features a separate dining room that easily converts to a main-level bedroom, perfectly adapting to your lifestyle needs. The kitchen features new, high-end s/steel appliances and a separate laundry room also houses the pantry. A full Bath completes this level. Upstairs, two bedrooms share a stylish full Bath and there is central air throughout the home. The standout highlight of this property is a separate, two-level detached artist's studio. The mezzanine floor has 360 degree views and is a perfect place to explore your creative talents. With French doors opening gracefully to a lush yard and established vegetable garden, this space serves as an inspiring retreat for arts & crafts, a workshop, home office, or a peaceful hang out space.

9 Rte 37th Ctr, Sherman

$475,000

Rare Sherman, CT opportunity on 2.1 private acres close to to the end of a quiet cul-de-sac. This charming 2-bed, 1-bath home features beautiful hardwood floors throughout, a screened front porch, detached garage, mature landscaping and lots of privacy-classic New England setting minutes from local amenities. Solid bones and high upside: the kitchen can be opened to create a modern open floor plan. The oversized bath can be reworked into a Jack-and-Jill; and a large, dry unfinished basement with high ceilings offers space for a family room, extra bedrooms, office, gym, or potential in-law suite. With vision and finishing touches, significant value can be added. This is a Probate Sale and needs Court Approval. This property is being sold "AS IS".

2 Beds ⋅ 1 Baths ⋅ 24155850 MLS

Rare Sherman, CT opportunity on 2.1 private acres close to to the end of a quiet cul-de-sac. This charming 2-bed, 1-bath home features beautiful hardwood floors throughout, a screened front porch, detached garage, mature landscaping and lots of privacy-classic New England setting minutes from local amenities. Solid bones and high upside: the kitchen can be opened to create a modern open floor plan. The oversized bath can be reworked into a Jack-and-Jill; and a large, dry unfinished basement with high ceilings offers space for a family room, extra bedrooms, office, gym, or potential in-law suite. With vision and finishing touches, significant value can be added. This is a Probate Sale and needs Court Approval. This property is being sold "AS IS".

17 Mauweehoo Hl, Sherman

$440,000

FOUNDATION READY BUILD SITE! Down a quiet stretch of road in the quaint town of Sherman a hidden drive leads you away from the world into 14 acres of absolute tranquility. As you walk the land you'll find the remnants of historic stone walls intertwining through the woods. The air is still, save for the rustle of native trees and the quiet life surrounding a private vernal pond. While the land feels like a wild escape the groundwork for your future has been meticulously laid. There's no need to wonder if you can build, the path has been cleared for you: driveway in place, home site cleared, well installed, septic field, electric and cable run to build site, wetlands and planning & zoning approval - it doesn't get more ready than this! Whether you wish to collaborate with the preeminent local builder who currently holds the permit, or bring your own team to execute a custom design, all the prep work is done and the site is ready for its next chapter. This prime location offers easy commuting to White Plains (just 45 miles away) and New York City (just 60 miles away), as well as easy access to the charming town center, just 2 minutes away. There you'll find community amenities including library, parks, tennis courts, pavilion, and a sandy beach including boat slips on CANDLEWOOD LAKE. Sherman is known for it's low taxes and K-8 school (with a choice of local high schools) thus making this property a rare gem!

24172170 MLS

FOUNDATION READY BUILD SITE! Down a quiet stretch of road in the quaint town of Sherman a hidden drive leads you away from the world into 14 acres of absolute tranquility. As you walk the land you'll find the remnants of historic stone walls intertwining through the woods. The air is still, save for the rustle of native trees and the quiet life surrounding a private vernal pond. While the land feels like a wild escape the groundwork for your future has been meticulously laid. There's no need to wonder if you can build, the path has been cleared for you: driveway in place, home site cleared, well installed, septic field, electric and cable run to build site, wetlands and planning & zoning approval - it doesn't get more ready than this! Whether you wish to collaborate with the preeminent local builder who currently holds the permit, or bring your own team to execute a custom design, all the prep work is done and the site is ready for its next chapter. This prime location offers easy commuting to White Plains (just 45 miles away) and New York City (just 60 miles away), as well as easy access to the charming town center, just 2 minutes away. There you'll find community amenities including library, parks, tennis courts, pavilion, and a sandy beach including boat slips on CANDLEWOOD LAKE. Sherman is known for it's low taxes and K-8 school (with a choice of local high schools) thus making this property a rare gem!

5 Brinsmade Ln, Sherman

$439,000

Charming and completely renovated in 2018, this turnkey 2-bedroom, 2 full bath high ranch in scenic Sherman delivers the perfect mix of modern updates and timeless country charm. Major improvements include new roof, siding, windows, septic, well, and upgraded electrical for easy, low-maintenance living. Sun-filled main level features hardwood floors, deep windowsills, an updated kitchen with natural wood countertops, and a full bath. The home offers a unique and functional layout with two access points to the upper level, creating easy flow and flexibility for everyday living. Convenient access from the kitchen to the yard makes outdoor entertaining, gardening, and dining effortless. The finished lower level with second full bath provides flexible space for guests, home office, recreation room, multi-generational living or rental potential. Set in a peaceful setting with room for gardening, a seasonal brook, and a shed ideal for hobbyists or extra storage, this property is perfect as a full-time home, weekend escape, or income-producing opportunity. Sherman is known for its charm and low taxes. It is a great location for a second/weekend home. Enjoy beach rights and boating on nearby Candlewood Lake less than five minutes away. Known for its historic New England charm, rolling farmland, open space, and relaxed lifestyle, Sherman offers local farms, small shops for everyday essentials, and preserved natural beauty-all just 90 minutes from New York City.

2 Beds ⋅ 2 Baths ⋅ 24174760 MLS

Charming and completely renovated in 2018, this turnkey 2-bedroom, 2 full bath high ranch in scenic Sherman delivers the perfect mix of modern updates and timeless country charm. Major improvements include new roof, siding, windows, septic, well, and upgraded electrical for easy, low-maintenance living. Sun-filled main level features hardwood floors, deep windowsills, an updated kitchen with natural wood countertops, and a full bath. The home offers a unique and functional layout with two access points to the upper level, creating easy flow and flexibility for everyday living. Convenient access from the kitchen to the yard makes outdoor entertaining, gardening, and dining effortless. The finished lower level with second full bath provides flexible space for guests, home office, recreation room, multi-generational living or rental potential. Set in a peaceful setting with room for gardening, a seasonal brook, and a shed ideal for hobbyists or extra storage, this property is perfect as a full-time home, weekend escape, or income-producing opportunity. Sherman is known for its charm and low taxes. It is a great location for a second/weekend home. Enjoy beach rights and boating on nearby Candlewood Lake less than five minutes away. Known for its historic New England charm, rolling farmland, open space, and relaxed lifestyle, Sherman offers local farms, small shops for everyday essentials, and preserved natural beauty-all just 90 minutes from New York City.

35 Rte 39 S, Sherman

$425,000

Nestled on one of our most desirable roads in town, CHURCH ROAD, find this easy living home for individuals seeking a peaceful retreat situated to 2.65 ACRES in back to nature setting. Carefree living w/views of nature and large acreage parcels. Enjoy walking down this road with numerous farms and our adorable brook, The Naromiyocknowhusunkatankshunk Brook (water flowing from the hills) A nature lovers paradise. ML offers LR w/bay windows, kitchen w/door to rear deck, 3 BD and 2 full BA. DR has sliders to spacious rear deck andadjoining screened porch. LL offers flex space for office or addition BD, game/rec room and laundry hookup with access to 1 Car Garage & walkout. Extra parking available. 2M to quaint Town Center/2.5M to Town Park w/Basketball, Baseball, Jogging Path, Jungle Gym, Tennis & Pickle Ball Courts, then a short walk to Town Pavaillion Beach and boat slips on CANDLEWOOD LAKE. 4M to private golf club-The Club @ River Oaks/5M to NY Line/10M to Metro North Train Station/5M to CT Audubon Deer Pond Farm Sanctuary/2M to White Silo Farm & Winery. Welcome to SMALL TOWN USA and low taxes!

3 Beds ⋅ 2 Baths ⋅ 24186664 MLS

Nestled on one of our most desirable roads in town, CHURCH ROAD, find this easy living home for individuals seeking a peaceful retreat situated to 2.65 ACRES in back to nature setting. Carefree living w/views of nature and large acreage parcels. Enjoy walking down this road with numerous farms and our adorable brook, The Naromiyocknowhusunkatankshunk Brook (water flowing from the hills) A nature lovers paradise. ML offers LR w/bay windows, kitchen w/door to rear deck, 3 BD and 2 full BA. DR has sliders to spacious rear deck andadjoining screened porch. LL offers flex space for office or addition BD, game/rec room and laundry hookup with access to 1 Car Garage & walkout. Extra parking available. 2M to quaint Town Center/2.5M to Town Park w/Basketball, Baseball, Jogging Path, Jungle Gym, Tennis & Pickle Ball Courts, then a short walk to Town Pavaillion Beach and boat slips on CANDLEWOOD LAKE. 4M to private golf club-The Club @ River Oaks/5M to NY Line/10M to Metro North Train Station/5M to CT Audubon Deer Pond Farm Sanctuary/2M to White Silo Farm & Winery. Welcome to SMALL TOWN USA and low taxes!

63 Church Rd, Sherman

$410,000

Welcome to rustic Timber Trails and Pepper Pond Road, located in southern Sherman, CT, near the New Fairfield and New York state border, offering a peaceful back-to-nature setting. Techbuilt home, part of the iconic mid-century modern prefabricated designs by architect Carl Koch, blends timeless character with warmth and functionality. Hardwood floors throughout, while the living room is flooded with natural sunlight from floor-to-ceiling windows and features a fireplace & sliders leading to an open-air covered deck. The home offers 2 oversized bedrooms, with potential for 4 bedrooms, lower level with workshop, basement area, and a 2-car garage. The partially fenced yard features mature gardens and plenty of space. Located in sought-after Southern Sherman, easy access to Metro North train stations, approximately 45 minutes to White Plains and 60 miles to Manhattan. Minutes from Sherman's charming town center with tennis and pickleball courts, ball fields, walking trails, hiking, and town beach access on Candlewood Lake with boat slips plus canoe and kayak racks. Enjoy year-round recreation with nearby boating, hiking, skiing, snowboarding, wineries, breweries, apple picking, and farm-to-table dining. Sherman is known for some of the lowest property taxes in Connecticut while offering a peaceful small-town lifestyle with convenient access to everyday amenities. Timber Trails Rd Asso. is $200 a quarter.

2 Beds ⋅ 2 Baths ⋅ 24175536 MLS

Welcome to rustic Timber Trails and Pepper Pond Road, located in southern Sherman, CT, near the New Fairfield and New York state border, offering a peaceful back-to-nature setting. Techbuilt home, part of the iconic mid-century modern prefabricated designs by architect Carl Koch, blends timeless character with warmth and functionality. Hardwood floors throughout, while the living room is flooded with natural sunlight from floor-to-ceiling windows and features a fireplace & sliders leading to an open-air covered deck. The home offers 2 oversized bedrooms, with potential for 4 bedrooms, lower level with workshop, basement area, and a 2-car garage. The partially fenced yard features mature gardens and plenty of space. Located in sought-after Southern Sherman, easy access to Metro North train stations, approximately 45 minutes to White Plains and 60 miles to Manhattan. Minutes from Sherman's charming town center with tennis and pickleball courts, ball fields, walking trails, hiking, and town beach access on Candlewood Lake with boat slips plus canoe and kayak racks. Enjoy year-round recreation with nearby boating, hiking, skiing, snowboarding, wineries, breweries, apple picking, and farm-to-table dining. Sherman is known for some of the lowest property taxes in Connecticut while offering a peaceful small-town lifestyle with convenient access to everyday amenities. Timber Trails Rd Asso. is $200 a quarter.

4 Pepper Pond Rd, Sherman

$400,000

Welcome to 2 Laurel Hill Road North, a peaceful retreat tucked away in the scenic town of Sherman. Surrounded by mature trees and natural beauty, this home offers the privacy and seclusion buyers seek while remaining close to the New Fairfield town line, historic Sherman Center, and the neighboring New Milford community. Enjoy the relaxed lifestyle of Connecticut's lake country, with Candlewood Lake and Squantz Pond nearby for boating, fishing, kayaking, swimming, and quiet days by the water. Sherman is known for its spacious surroundings, charming small-town atmosphere, and slower pace of life, making this an ideal setting for a full-time residence or tranquil weekend escape.

2 Beds ⋅ 1 Baths ⋅ 24195986 MLS

Welcome to 2 Laurel Hill Road North, a peaceful retreat tucked away in the scenic town of Sherman. Surrounded by mature trees and natural beauty, this home offers the privacy and seclusion buyers seek while remaining close to the New Fairfield town line, historic Sherman Center, and the neighboring New Milford community. Enjoy the relaxed lifestyle of Connecticut's lake country, with Candlewood Lake and Squantz Pond nearby for boating, fishing, kayaking, swimming, and quiet days by the water. Sherman is known for its spacious surroundings, charming small-town atmosphere, and slower pace of life, making this an ideal setting for a full-time residence or tranquil weekend escape.

2 Laurel Hill Rd N, Sherman

$336,000

Steeped in history and dripping with cottage charm, the "Maltby Gelston" house is more than just a home-it's a piece of Sherman's history! This residence has worn many hats over its 200 (or so) years: from the homestead of a prominent 19th-century family, to "Brush House", to an early 20th-century harness shop. Today, this iconic "little yellow house" is celebrated as one of the cutest properties in town. Inside, the home oozes character with a layout that favors intimacy and architectural interest. Whether you're seeking a full-time residence, a weekend escape, or writer's retreat, the "stacked room" English-cottage floor plan offers charm at every level: spacious primary suite featuring a freshly remodeled bathroom, living room anchored by a large wood-burning fireplace perfect for long New England winters, dining adjacent to a separate kitchen with stainless appliances, and finished attic serving as a stylish sleeping loft for guests or a quiet sky-lit office. You will spend your summer living on the very private, spacious deck. Meticulously maintained perennial gardens that burst with color and tranquil views of the neighboring horse farm offers your rural zen moment. Take a 3 minute drive or 10 minute jog to Candlewood Lake for beach, boating and kayaking; walking distance to pickleball at Volunteer Park, plus nearby soccer fields, tennis courts & a walking track. Easy access to the Appalachian Trail, Audubon's Deer Park Farm & Pawling Train Station!

1 Beds ⋅ 1 Baths ⋅ 24154621 MLS

Steeped in history and dripping with cottage charm, the "Maltby Gelston" house is more than just a home-it's a piece of Sherman's history! This residence has worn many hats over its 200 (or so) years: from the homestead of a prominent 19th-century family, to "Brush House", to an early 20th-century harness shop. Today, this iconic "little yellow house" is celebrated as one of the cutest properties in town. Inside, the home oozes character with a layout that favors intimacy and architectural interest. Whether you're seeking a full-time residence, a weekend escape, or writer's retreat, the "stacked room" English-cottage floor plan offers charm at every level: spacious primary suite featuring a freshly remodeled bathroom, living room anchored by a large wood-burning fireplace perfect for long New England winters, dining adjacent to a separate kitchen with stainless appliances, and finished attic serving as a stylish sleeping loft for guests or a quiet sky-lit office. You will spend your summer living on the very private, spacious deck. Meticulously maintained perennial gardens that burst with color and tranquil views of the neighboring horse farm offers your rural zen moment. Take a 3 minute drive or 10 minute jog to Candlewood Lake for beach, boating and kayaking; walking distance to pickleball at Volunteer Park, plus nearby soccer fields, tennis courts & a walking track. Easy access to the Appalachian Trail, Audubon's Deer Park Farm & Pawling Train Station!

3 Gelston Rd, Sherman

$205,000

Down a quiet road in the heart of Sherman, this exceptional 5 ACRE parcel offers a rare blend of readiness and wildness. It's a place where nature feels untouched, a private sanctuary defined by moss covered stone outcroppings, a variety of native trees and the constant, melodic song of a babbling brook. The atmosphere is nothing short of MAGICAL. This isn't just raw land; it is a coveted building lot with a thoughtful site plan and health dept approval already in place, positioning you one step closer to breaking ground on your home vision. While the property feels worlds away, it remains perfectly connected to the best of the Litchfield Hills and the Hudson Valley. Enjoy access to the waters of CANDLEWOOD LAKE, local hiking trails, serene fishing spots, all while being just minutes from the small-town charm of Sherman and neighboring Pawling. Whether it's a weekend escape or a permanent change of pace, this property is a rare find, a peaceful haven just 1 hour and 20 minutes from New York City. This is where the landscape sets the tone and your ideas can finally take root.

24163707 MLS

Down a quiet road in the heart of Sherman, this exceptional 5 ACRE parcel offers a rare blend of readiness and wildness. It's a place where nature feels untouched, a private sanctuary defined by moss covered stone outcroppings, a variety of native trees and the constant, melodic song of a babbling brook. The atmosphere is nothing short of MAGICAL. This isn't just raw land; it is a coveted building lot with a thoughtful site plan and health dept approval already in place, positioning you one step closer to breaking ground on your home vision. While the property feels worlds away, it remains perfectly connected to the best of the Litchfield Hills and the Hudson Valley. Enjoy access to the waters of CANDLEWOOD LAKE, local hiking trails, serene fishing spots, all while being just minutes from the small-town charm of Sherman and neighboring Pawling. Whether it's a weekend escape or a permanent change of pace, this property is a rare find, a peaceful haven just 1 hour and 20 minutes from New York City. This is where the landscape sets the tone and your ideas can finally take root.

10 Chimney Hill Rd, Sherman

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