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47 Rt 39th So, Sherman
$630,000
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

11 Gelston Rd, Sherman
$599,000
3 Beds ⋅ 2 Baths ⋅ 24152932 MLS
Charming updated Antique Country Cape in extremely private setting w/low maintenance grounds on 3.7 ACRES. Gelston Road is a desirable country lane - a short horseshoe-shaped dirt road and less than 1 mile from Town. A great offering for weekend getaways or full time privacy. A paved driveway with loads of parking leads to this quaint Home. Main Level offers a vaulted Great Room w/beams, built in bookcases and bookshelves open to Dining Room. Office or small bedroom across from full bath. Primary Bedroom w/private full BA. Both Baths have been updated. Adorable Sunroom/den w/Brick Fireplace. Country Kitchen w/stainless steel appliances overlook private front yard. Upper Level w/2 additional bedrooms. Clean and neat basement w/extra storage. AC/Roth oil tank. Freshly painted. Sought after SHERMAN location for easy commutes. 1M to quaint town center, 2M to community tennis & pickle ball courts, ball field, basketball, walking/jogging path, pavilion and beach on CANDLEWOOD LAKE w/town boat slips, canoe & kayak racks. 4M to private golf club -The Club @ River Oaks. 45M to White Plains/60M to Manhattan. Access to 2 Metro North Train Stations. Come enjoy our low taxes in small town USA!

11 Gelston Rd, Sherman

1 Coburn Rd W, Sherman
$590,000
2 Beds ⋅ 2 Baths ⋅ 24075758 MLS
Enchanting 1700's Antique Home with Modern Artistry and Bucolic Charm! Step back in time, to this extraordinary residence brimming with character and nestled in a tranquil setting. As you enter, you are greeted by the timeless beauty of exposed wooden beams that evoke the home's rich history. The kitchen is a chef's delight, featuring a stunning copper farmhouse sink, which complements the rustic elegance of the space. It's a perfect blend of antique charm & modern functionality. A wood burning fire sets the cozy scene in the living room and the Sunroom is a bright, inspiring space for year round use. The property boasts two well-appointed bedrooms and a versatile attic space which has been creatively transformed into a dual-purpose music room & designer studio; showcasing the home's flexible living spaces that cater to both artistic expression and practical needs. Enjoy the several outdoor entertaining areas where you can "relax" in an ice bath...or warm up by the fire pit! Set in a superbly quiet location, this home is a sanctuary of peace, where the only sounds are those of nature's symphony. The surrounding landscape is a picturesque tapestry of natural beauty, offering a sense of privacy and seclusion that is increasingly rare to find. Located in the charming town of Sherman with access to Candlewood Lake, close to NY-22 for NYC & Metro North Trains. This property is a true gem waiting to be discovered by someone who seeks a lifestyle that is anything but ordinary.

1 Coburn Rd W, Sherman

107 Church Rd, Sherman
$575,000
2 Beds ⋅ 2 Baths ⋅ 24140397 MLS
Discover the charm and tranquility of this inviting country home set on 8+ picturesque acres! The added benefit is that the land has been subdivided into two lots to offer built-in flexibility for future expansion, investment, or resale, while still providing plenty of space & privacy. This warm and welcoming property features 2 bedrooms and 2 full bathrooms, offering comfortable living in a serene setting. The spacious living room boasts a cathedral ceiling, wood-burning fireplace, and abundant natural light, creating the perfect space to relax or entertain. Enjoy the privacy and beauty of nature as the property borders conservation land, ensuring lasting peaceful views and protected surroundings. A rare opportunity to own a versatile and scenic property with endless potential.

107 Church Rd, Sherman

1 Kaylyn Ln, Sherman
$575,000
2 Beds ⋅ 2 Baths ⋅ 24110206 MLS
Nestled on 2 acres of peaceful woodlands, this sprawling 3,203 sq ft Contemporary Ranch offers privacy, space+incredible potential. Step into a bright+spacious Living Room featuring engineered hardwood floors, floor-to-ceiling windows+access to the deck. In the Kitchen are granite countertops, stainless steel appliances+a breakfast bar. An oversized skylight fills the adjoining Dining Room with natural light, while sliding doors open to outdoor living space. The Primary Bedroom Suite includes hardwood floors, full length windows, a dressing area with granite-topped vanity, jetted tub+a large walk-in wardrobe closet. A generously sized 2nd bedroom includes a closet+ceiling fan, and the Den, complete with built-ins+its own closet, can easily function as a 3rd bedroom. An indoor hot tub room with vaulted ceilings+sliders to the deck adds a unique retreat space. The sunken Family Room offers Contemporary flair with its cathedral ceiling, exposed beams, geometric windows, floor-to-ceiling fireplace+direct access to the covered deck. Additional spaces include a main-floor laundry room with washer+dryer, full-sized unfinished basement with workshop+yard access+an oversized attached 2-car garage. Set against a serene backdrop is an in-ground pool. Just minutes from Squantz Pond+Sherman's Town Beach on Candlewood Lake, this property is a nature lover's dream. With some clearing+updating, this home presents an excellent opportunity to create your ideal retreat.

1 Kaylyn Ln, Sherman

15 Wagon Wheel Rd, Sherman
$560,000
1 Beds ⋅ 2 Baths ⋅ 24128605 MLS
Fixer upper on waterfront lot with approximately 100 feet on Squantz Pond! Gorgeous location on beautiful Wagon Wheel Road with views and level access to lake. A diamond in the rough. Large open two-story floor plan on main level with extra loft space on second level. Oversized windows offer beautiful views. A level walk into the water, great for fishing, kayaking, canoeing and just enjoying the lake life! The home is in need of renovation; first floor offers, a large foyer, a spacious kitchen and great room that opens up to a sunroom and an outdoor wood deck overlooking the lake. There is a first-floor bedroom with ensuite potential- toilet and plumbing still there but it had been converted into a nice sized office. There is a hallway full bath on the first floor. There is hardwood flooring throughout, linoleum in the kitchen, parquet floor in the dining area and blue slate in the sunroom. The second floor offers a large loft space for potential additional bedroom/office with a sliding glass door that opens on to a small deck. The large full house basement is a walkout. THIS HOME IS SOLD "AS IS", AND INSPECTIONS ARE FOR THE BUYERS OWN INFORMATION.

15 Wagon Wheel Rd, Sherman

9 Rte 37th Ctr, Sherman
$515,000
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

49 Quaker Ridge Rd, Sherman
$480,000
4 Beds ⋅ 2 Baths ⋅ 24128752 MLS
Cape on Quaker Ridge! Looking for an affordable entry into Sherman? This 4-bedroom, 2-bath Cape, set at the end of a quiet cul-de-sac on sought-after Quaker Ridge Road, offers just that-plus a premium 2.28-acre lot. Owned by the same owner for over 40 years, this home is ready for its next chapter and new owners to enjoy for decades to come. Opportunities for expansion are plentiful, with an unfinished lower level and additional unfinished loft space above the 2-car attached garage (plus a 2-car under-house garage for even more flexibility). The serene lot includes a shed and promises lasting peace and quiet. Inside, the main level features a vaulted-ceiling family room with wood-burning fireplace. An eat-in kitchen with new stainless backsplash with knife rack and hooks, and new dishwasher, plus two bedrooms and a full bath-ideal for those seeking main-level living. Upstairs you'll find two more bedrooms and another full bath. A dining area slider opens to the rear deck and provides convenient access to the garage and loft. Bring your vision and see how this well-located property can become the Sherman home you've been waiting for! Convenient location within 30 minutes of two train stations. Minutes to New Milford, Kent and I84 and minutes to Route 22 in New York. Sherman Town Park Lake access. Sherman provides residents with a choice of five public high schools including New Milford, New Fairfield, Danbury, Henry Abbott Tech and Shepaug. Sold As Is

49 Quaker Ridge Rd, Sherman

17 Mauweehoo Hl, Sherman
$475,000
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

5 Brinsmade Ln, Sherman
$440,000
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

35 Rte 39 S, Sherman
$439,000
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

63 Church Rd, Sherman
$425,000
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

4 Pepper Pond Rd, Sherman
$410,000
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

3 Gelston Rd, Sherman
$336,000
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

2 Coburn Rd W, Sherman
$225,000
24133934 MLS
Absolute Privacy Tucked Away on 1+ Acre in true nature setting- abuts open space. POTENTIAL FOR VIEWS EAST TOWARD TIMBER LAKE. This approved building lot offers an acceptional opportunity awaits a savvy buyer to create their own personal retreat in the small Town of Sherman. Test work completed with approved 4 BDRM Septic Plan. Driveway is 1600 ft long, passiing through a majestic pond at the road entrance. 1 Mile to NY Line! Ease and proximity to Metro North Train Station/5 min to quaint Town Center w/community park, basketball, tennis & pickle ball courts, jogging path/tow boat slips/kayak-canoe racks & sandy beach on CANDLEWOOD LAKE. 10m to private golf club(The Club @ River Oaks) 10 M to Quaker Hill Country Club. 1M to 835 Acres Deer Pond Farm Sanctuary-Audubon Center w/ its 20M of trails. Less than 60M to NYC - makes for a perfect weekend retreat or year round living. Welcome to Small Town USA and our LOW TAXES! Builder available with plans and will walk land.

2 Coburn Rd W, Sherman

10 Chimney Hill Rd, Sherman
$205,000
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

8 Chimney Hill Rd, Sherman
$185,000
24163701 MLS
Discover the tranquil allure of Sherman CT on this 2.10 acre property, just a serene 69-mile drive from NYC. Enveloped in the soothing sounds of Toll Brook as it gracefully flows into Candlewood Lake, this parcel is an approved building lot with an existing site plan and health dept approval. This land presents an excellent opportunity to claim a slice of Sherman's charm with the convenience of a ready-to-build lot with gorgeous mossy rock outcroppings, native trees and plants. Enjoy Sherman's charming town center nearby, offering a library, parks, sandy beach, town boat slips, and easy access to CANDLEWOOD LAKE. A builder is available to discuss custom home designs that integrate seamlessly with this stunning setting. Bring your ideas to this magical backdrop. This setting epitomizes tranquility and natural beauty. Come see for yourself!

8 Chimney Hill Rd, Sherman

64 Skyline Dr, Sherman
$180,000
24161541 MLS
Exceptionally rare opportunity to acquire the very last available lot on Skyline Drive featuring breathtaking views of Candlewood Lake and magnificent sunsets. Prepare to be awestruck at the unparalleled views perched up where eagles glide by! This prime parcel is an approved building lot in the Candlewood Lake Estates subdivision. An experienced Architect/Builder is available to help bring your vision to life. Enjoy deeded access to FOUR PRIVATE BEACHES, including the pristine spring-fed Emerald Lake (Green Pond), minutes from NYC yet worlds away. The gated community, once known as "Little Switzerland" for its charming chateaus nestled in the picturesque mountainous terrain, is also dotted with stunning modern homes. Candlewood Lake Estates offers 2 dedicated boat dockage areas and additional beaches on Candlewood Lake, plus access to Green Pond a peaceful, no motor-boats environment, perfect for swimming, kayaking and paddleboarding. Candlewood Lake Estates is a tax district, not an HOA, with a current mil rate of 5.48. SHERMAN CT is known for it's low taxes and great PreK-8 school (with a choice of local high schools) thus making it a rare gem! Embrace this extraordinary opportunity to craft your own distinctive retreat and enjoy peaceful living. Secure this coveted lot before it's gone!

64 Skyline Dr, Sherman

18 Candlewood Lake Dr, Sherman
$175,000
24127580 MLS
Exclusive Opportunity in Sherman, CT: Build Your Dream Home on Candlewood Lake Estates Prime Building Lot with Partial Candlewood Lake Views - Just Steps from Beach and Docks Discover the ultimate lakeside lifestyle in the prestigious, gated community of Candlewood Lake Estates. This rare 4-bedroom home site is fully approved and ready for your floorplans, offering unparalleled convenience and serenity. Nestled in Sherman, CT, this lot boasts stunning partial views of Candlewood Lake, with easy walking access to private beaches and docks - perfect for boating, swimming, and lakeside relaxation. Key Features: Approved Site Plan: Health Department and Wetlands Commission approvals for a spacious 4-bedroom single-family home - no delays, just start building your vision. Prime Location: Gated enclave ensures privacy and security, with immediate proximity to community amenities including beaches, docks, and recreational facilities. Scenic Appeal: Elevated lot captures seasonal lake vistas, surrounded by mature trees and natural beauty - ideal for a custom retreat. Uniqueness: Rarely available land in Sherman in a gated lake community - don't miss your chance to claim it. Imagine waking up to lake breezes, hosting sunset gatherings on your deck, and creating family memories in one of Connecticut's most coveted waterfront destinations. Whether you're a boating enthusiast or seeking a peaceful escape from the city, this lot delivers it all.

18 Candlewood Lake Dr, Sherman

47 Sunset Dr, Sherman
$40,000
24155439 MLS
Seize the opportunity to build your custom lake retreat on a spectacular, sloped lot overlooking the serene waters of Candlewood Lake. This raw land features dramatic rock outcroppings, providing a unique, natural foundation for your architectural vision. Positioned to capture an incredible westerly view, you will enjoy breathtaking, unobstructed sunsets that paint the sky every evening. Ownership includes access to all Candlewood Lake Estates facilities and amenities, including the private beaches. For those seeking more peaceful waters, the community also provides access to the tranquil Green Pond, where motorized boats are strictly prohibited, ensuring a perfect escape into nature. Create a home as unique as its setting and start living the lake life you've always imagined.

47 Sunset Dr, Sherman

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