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37 Lamppost Dr, Redding
$840,000
4 Beds ⋅ 3 Baths ⋅ 24175748 MLS
Highest and best due 6/1/@ 4PM Nestled on a quiet cul-de-sac in desirable West Redding, this inviting 4 bedroom, 2.5 bath home offers the perfect blend of comfort, space, sustainability, and commuter convenience. Located in a town affectionately known as the "Vermont of Connecticut," Redding is cherished for its scenic wooded landscapes, top ranked schools, and peaceful atmosphere. Inside, a thoughtfully designed floor plan provides both functionality and warmth. The spacious front to back living room features a classic wood burning fireplace, creating the perfect gathering space for relaxing or entertaining. A formal dining room with beautiful built in banquet cabinets, while a private home office offers flexibility for today's work from home lifestyle. A standout feature is the expansive bonus room, currently used as an art studio, offering endless possibilities as a playroom, media room, gym, or creative space. Upstairs, four generously sized bedrooms and two full baths provide comfortable accommodations for family and guests alike. Outdoor living is equally inviting. The large screened in porch is the ideal place to enjoy a quiet morning coffee or unwind with an afternoon cocktail while taking in the peaceful surroundings. Just beyond, the paver patio creates the perfect setting for roasting marshmallows, entertaining guests, or simply enjoying the idyllic scenery that makes Redding so special.

37 Lamppost Dr, Redding

41 Sullivan Dr, Redding
$835,000
5 Beds ⋅ 5 Baths ⋅ 24128636 MLS
Nestled on a quiet cul-de-sac, this beautiful home is sited on 2.2 private acres and combines comfort, charm and flexibility. With five bedrooms - including a private nanny or in-law suite- there's room for everyone. The inviting kitchen opens to a generous family room highlighted by a stunning brick fireplace and french doors that lead to a spacious deck overlooking the serene property. A lovely formal dining room provides the perfect setting for special gatherings, while the living room, complete with its own fireplace, adds warmth and charm. The second floor encompasses the primary bedroom with walk in closet and full bath. Three additional bedrooms and full bath complete the second floor. A finished lower level adds even more versatility, featuring a spacious rec room, library or office and guest room plus a full bath-perfect for visitors, work, or play. Enjoy all the charm Redding has to offer and make this special home your own. Convenient to schools, shopping, commuting with Redding train station minutes away. It's time to make it your own home!

41 Sullivan Dr, Redding

29 Meeker Hill Rd, Redding
$812,500
4 Beds ⋅ 3 Baths ⋅ 24123993 MLS
Welcome to 29 Meeker Hill Road, a warm and inviting 4-bedroom, 2.5-bath home nestled on 2 acres of level, cleared land in beautiful Redding. With nearly 1,900 sq. ft. of living space, this multi-level home is filled with natural light and offers the perfect blend of comfort, charm, and practicality. The property's standout feature is the incredible barn-ideal as a workshop, studio, or creative space. Surrounded by open, usable land, you'll have plenty of room to garden, entertain, or simply enjoy the peace and quiet of country living. This is a rare opportunity to own a home with character, space, and potential in a sought-after community with excellent schools. Don't miss your chance-schedule a showing today and see why 29 Meeker Hill Road is the cozy retreat you've been waiting for. HIGHEST AND BEST BY MONDAY AT 5PM...

29 Meeker Hill Rd, Redding

35 Deer Spring Rd, Redding
$810,000
4 Beds ⋅ 4 Baths ⋅ 24177343 MLS
Classic New England colonial with 3 car garage and 2.05 sprawling level acres with in-ground pool. This home has been lovingly cared for by the same owners for over 30 years. Traditional center hall layout with welcoming entry foyer that leads to the formal living room with hardwood floor, fireplace, and sliders to the rear terrace flanked by floor to ceiling built-in bookshelves; plus elegant dining room with crown and chair rail moldings. Expansive kitchen with center island, sunlit breakfast nook with bay window, skylights, plus adjoining patio overlooking the pool and gardens. The impressive 24' x 22' level great room with full bath makes a wonderful family room, main level primary or guest bedroom, and features walls of windows and sliders to the picturesque backyard. The second floor offers the spacious primary suite with adjoining sitting room, hardwood floors, and private bath; plus two additional cheery bedrooms with shared hall bath. Of note: central air; garden shed; pull down attic with storage; plus expansive, partially finished lower level featuring abundant storage space, workshop, and rec room. Idyllic setting and desirable location, convenient to the West Redding train station and just 69 miles to Midtown. Note: the pool has not been opened in some time and is being sold as-is. It has a vinyl liner which may need to be replaced. Amazing opportunity and unlimited potential in this stately home!

35 Deer Spring Rd, Redding

148 Old Redding Rd, Redding
$800,000
4 Beds ⋅ 3 Baths ⋅ 24169820 MLS
HIGHEST and BEST By TUESDAY MAY 5TH. Tucked away, off the beaten path and down a quiet country lane, this charming 4-bedroom, 2.5-bath Cape Cod home offers a peaceful retreat surrounded by nature. With more than 2,300 square feet of living space, this well-loved home combines warmth, character, and endless potential. The main level features two bedrooms, a full bath, and a flexible layout that includes a kitchen, dining room and living room with a fireplace. A beautiful sun-room overlooking the woods provides a special retreat to unwind from the day. An office/library area with built-in shelves and access to the deck provides the perfect space for working or relaxing. An additional roughed-in bath offers an opportunity for future customization. Upstairs, you'll find two bedrooms and another full bath. A walk-in attic with an adjacent walk-in closet leads to an additional attic space above the garage, presenting excellent storage or expansion possibilities. The partially finished walk-out lower level adds valuable living space, complete with an updated family room with fireplace, laundry area, half bath, updated lighting, and durable LVT flooring-ideal for extended living, guests, or a potential in-law setup.

148 Old Redding Rd, Redding

429 Rock House Rd, Redding
$800,000
4 Beds ⋅ 3 Baths ⋅ 24155279 MLS
Privately set on a serene back lot, this spacious 4-Bedroom, 2.5-Bath Colonial offers the perfect blend of classic charm and everyday comfort. Gleaming Hardwood Floors run throughout the home - excluding the Kitchen and Baths - adding warmth and continuity to the well designed layout. The Main Level features a gracious Formal Living Room with stately FP and Slider access to the expansive, well-maintained wood deck-ideal for relaxing or entertaining while enjoying the changing seasons. The Formal Dining Room is accented by a bright bay window-in fact-there is an abundance of windows throughout the home that allows for plenty of natural light. All Four Bedrooms are located on the Upper Level, offering privacy and a quiet retreat. Mechanical updates include a new furnace and hot water heater installed in 2021. The property features lovely level grounds bordered by light tree cover, creating a peaceful and usable outdoor space. A wonderful opportunity to own a spacious home in a desirable Redding location-Privacy, Comfort, and Natural Beauty all in One! Sale subject to probate approval.

429 Rock House Rd, Redding

1 Long Wall Rd, Redding
$800,000
5 Beds ⋅ 3 Baths ⋅ 24118336 MLS
First time on the market in forty-two years, welcome to 1 Long Wall Road! Situated in the center of Redding, minutes from Redding's schools, on a quiet Cul de sac, where neighbors stroll, walk dogs and families safely ride bikes. Nearby, Georgetown, Bethel and the Redding Market to shop. A multi-generational home on 2.76 acres, mature landscaping and babbling brook, access to Redding's hiking trails. The main house consists of 3 beds and 2 full baths, a breathtaking two-story cathedral ceilinged Great Room with roughhewn timbers and stone fireplace. A large, central kitchen adjoins the great room, den, loft space, dining area, and the large, screened porch looking out over a flat, expansive and bucolic backyard. A second story, primary bedroom suite with large ensuite bath and balcony that leads down to a multi-level, wraparound back deck connecting to the screened porch provides for an ideal entertaining area for family barbeques, festivities or simply serene afternoon siestas! Beautiful slate accents, kitchen counters and bathroom floors, lovingly repurposed by the owners from the roof tiles of their 19th century Vermont farmhouse. The lower level, finished living space converted from a two-car garage includes two separate rooms housing mechanicals with large areas for storage. Integrated into the main house is a spacious 2-bed, 1-bath, legal apartment with kitchen, livingroom w/stone fireplace, dining room. Ideal accessory apartment, access from main house. A must see gem!

1 Long Wall Rd, Redding

471 Newtown Tpke, Redding
$799,000
3 Beds ⋅ 3 Baths ⋅ 24178600 MLS
Beautifully professionally landscaped, level 2-acre lot on the peaceful end of Newtown Turnpike, this charming 3-bedroom, 2.5-bath. Cape combines classic character with modern living. The home has been meticulously maintained and upgraded, offering a perfect retreat in the heart of Redding. Step into the heart of the home: a brand-new custom kitchen featured in the recently added expansion. Designed with both style and functionality in mind, the kitchen boasts white shaker cabinets, quartz countertops, a spacious center island with built-in microwave and beverage fridge, and high-end stainless steel appliances, including a gas cooktop and double-door refrigerator. Two large gold pendant lights and recessed lighting highlight the vaulted ceilings, creating a bright and luxurious atmosphere ideal for cooking and entertaining.

471 Newtown Tpke, Redding

18 Ledgewood Rd, Redding
$797,500
4 Beds ⋅ 3 Baths ⋅ 24169652 MLS
*Best & Final Offers by Monday (5/4) at 2pm* Welcome to 18 Ledgewood, a beautiful Contemporary home offering 2,900 square feet of well-proportioned living space in a desirable Redding, Connecticut setting. This 4-bedroom, 3 full bath home features a flexible layout with a potential main-level 5th bedroom and full bath, ideal for guests, extended family, or a private home office. The home offers generously sized living and dining areas with great natural light, providing a strong foundation for both everyday living and entertaining. The kitchen with breakfast bar features deck access to allow for easy indoor and outdoor entertaining. Upstairs, the additional bedrooms are spacious and well laid out, including a primary suite with ample closet space. Key improvements include a brand new roof and newer mechanicals, offering peace of mind on major components. A finished lower level walk-out to the backyard which is highlighted by an in-ground pool, creates the perfect setting for outdoor enjoyment and summer entertaining. With its exceptional layout, substantial square footage, and prime Redding location, this home presents a fantastic opportunity in a highly desirable area.

18 Ledgewood Rd, Redding

181 Picketts Ridge Rd, Redding
$775,000
4 Beds ⋅ 3 Baths ⋅ 24117718 MLS
Your own private oasis! Just imagine enjoying your morning coffee while watching hummingbirds and butterflies flutter by. Or birds feasting on the seeds of summer flowers. Conveniently located minutes from downtown Ridgefield, commuting routes and the NYC train, this 4-bedroom home can fit so many needs in its 2,420 sq ft of living space on 2 acres. Level backyard play area? Yes. One level living with separate guest space? Yes. A home office with a private entrance? Yes. Chef's kitchen with commercial grade refrigerator and freezer? Yes. Heated garage for a car aficionado? Yes. Add to this the joys of Redding, often called "the Vermont of Connecticut" with award winning schools and a strong pride of community. This home has been tastefully improved over the years to create an ease of living and lots of storage space. Nest thermostats. Automated locks. Full house generator. Deer fencing. Recent improvements include new septic tank (2025); radon air mitigation (2025); new AC (2023); driveway paving (2022). Full list in attachments.

181 Picketts Ridge Rd, Redding

45 Wayside Ln, Redding
$767,000
4 Beds ⋅ 3 Baths ⋅ 24117973 MLS
Sophisticated mid-century inspired modern deck house in the sought after Umpawaug area of West Redding, set back on 4 private acres with scenic views of the neighboring pond. Light, bright & open floor plan with 36'x16' beamed & vaulted great room featuring walls of windows & sliders to the wrap around deck, hardwood floor, fireplace, & custom built-in book shelves. The expansive main level also features the updated kitchen with quartz counters, decorative subway tile backsplash, & S/S appliances; plus adjoining light filled DR with vaulted ceiling & custom built-in display shelving. Total 2,958 sf including the expansive walk-out lower level featuring a spacious FR with floor to ceiling brick fireplace, private office with sliders to the backyard, convenient half bath, laundry room, 23'x13' studio or workshop, plus oversized 2+ car garage. Room for everyone with 4BR & 2 full baths in the private bedroom wing of this sprawling ranch. The primary suite features hardwood floors, dressing area with double closets, & full bath, The additional 3 BRs, all with hardwood floors, share the updated hall bath with pedestal sink & bead board wainscot. Many recent improvements: roof (2019), well pump (2021), generator hook up (2021), septic (2022), boiler (2022), new garage doors (2022), mini split in great room (2023) & more. Top location, convenient to Georgetown shops & restaurants, Mark Twain Library & West Redding station. Idyllic Redding-"The VT of CT" yet just 57 miles to Midtown.

45 Wayside Ln, Redding

172 Gallows Hill Rd, Redding
$760,000
2 Beds ⋅ 2 Baths ⋅ 24161711 MLS
Casually elegant stone & clapboard ranch on stunning property in most desirable West Redding. Park-like setting w/extensive flowering gardens, specimen trees, stone walls, stone patios, & inviting covered pergola seating area. This sophisticated home beckons w/glass breezeway between the 2 car garage w/cheery cupola & the main home w/fieldstone foundation, chimney, & cladding. Generous proportions & open flow including 1,373 sf on the main level plus 735 sf in the walk-out lower level w/total 2-3 BRs & 2 full baths. The heart of this home is the large living room w/custom built-ins & stone fireplace w/wood burning stove insert. The DR, open from the LR for ease of entertaining, features wide board floors & custom built-in shelving/lower cabinets flanking a large picture window. The main floor also features the bright white kitchen w/open shelves, S/S appliances, pantry & views to the stone patio/gardens. The bedroom wing offers one large BR w/multiple closets; 2nd BR w/built-in shelving, currently used as a den; plus the hall bath w/updated vanity & tub/shower. The walk-out lower level has been completely updated to create flexible living space including a family room w/2nd fieldstone fireplace; optional primary suite or guest bedroom w/French door to the stone patio; & full bath featuring glass basin sink & deep soaking tub. Many updates including exterior repainted & brand new roof (2025). Top location in sought after Redding, the "VT of CT," yet just 61 miles to Midtown.

172 Gallows Hill Rd, Redding

27 Apple Ln, Redding
$750,000
3 Beds ⋅ 2 Baths ⋅ 24181066 MLS
Idyllic country ranch in park like setting on 1.1 park like acres on desirable West Redding cul de sac with detached 2 car garage. This elegant home offers mature trees, flowering perennial gardens, deck, pea gravel patio w/stacked stone outdoor fireplace, & expansive rolling lawn. The sprawling main level is light, bright & open with newly refinished bleached hardwood floors & freshly painted interior. Ideal for gracious living & entertaining - enjoy the spacious living room w/brick fireplace flanked by built-in display shelves, plus the large family room/dining room featuring a built-in wet bar, sliders to the balcony/deck, more built-in shelving, plus open to the sunny kitchen showcasing brand new S/S appliances, breakfast nook, & adjoining deck. Step down from the kitchen to the dramatic vaulted sunroom, drenched in natural light, w/skylight, ceiling fan, wood burning stove, & double set of sliders to the deck for outdoor enjoyment. Total 2,265 sf on main & lower levels w/3 bedrooms, one full & one half bath. The primary bedroom offers a full wall of closets w/custom closet systems. All of the bedrooms offer hardwood floors & share the newly refreshed main floor bath with tub/shower enclosure, new fixtures & plantation shutters. Total 420 sf in the walk-out lower level rec room/den with new luxury vinyl plank flooring & newly remodeled powder room. Many additional updates (see Public Remarks Addendum). Top location, convenient to shops/train, & just 57 miles to Midtown.

27 Apple Ln, Redding

5 South Ln, Redding
$740,000
3 Beds ⋅ 2 Baths ⋅ 24160906 MLS
Perched at the crest of Redding Ridge on a lane shared by only five homes, this beautifully restored Cape occupies a truly commanding position. The property encompasses an entire side of South Lane, framed by original stone walls and mature trees that provide a sense of established privacy. In a region known for its rolling terrain, this home offers the rare luxury of an entirely usable, "pancake-flat" lot, providing the perfect vantage point for unobstructed views of both the sunrise and the sunset. The interior of the residence preserves its classic New England charm while embracing a modern, open-concept flow. Original wood-beamed ceilings and hardwood floors run throughout, lending an air of historic authenticity. The heart of the home is a sweeping living room anchored by a large central fireplace, flanked by thoughtful built-ins. For those who love to host, the formal dining room and renovated spaces make this house a true entertainer's delight, with practical upgrades like central air and main-floor laundry. The living space extends gracefully outdoors through an enclosed three-season porch, which serves as a bright transition to the backyard. This porch leads directly to a raised flagstone deck which offers peaceful views of the level grounds. With three generous bedrooms, two fully renovated baths, and a separate two-car garage, this home offers a timeless ridge-top lifestyle that is as functional as it is picturesque.

5 South Ln, Redding

159 Cross Hwy, Redding
$730,000
3 Beds ⋅ 2 Baths ⋅ 24165406 MLS
Charming turn-of-the-century Craftsman farmhouse on one of Redding's most picturesque Scenic Roads - a rare find for those seeking space, character, and a genuine sense of place within reach of the city, but worlds away from it. Featuring authentic period details including crown molding, a bay window, beautiful hardwood floors, and soaring 9-foot ceilings, this three-bedroom, two-bath home balances historic charm with thoughtful modern updates. A newly expanded primary suite and a brand-new full bath on the second floor - complete with new HVAC - make the home as comfortable as it is characterful. Once the original switchboard for Redding Ridge, the property sits on a large, level lot with mature landscaping, spectacular perennial gardens that bloom spring through fall, a deck, brick terrace, and storage shed. The new roof and all-new windows mean the big work is done - just move in. Beyond the property itself, Redding delivers the lifestyle that's increasingly hard to find closer to the city: miles of open space, hiking trails, and beloved local institutions like the Mark Twain Library, New Pond Farm, Huntington State Park, and Putnam Park. It's a town with a strong sense of community, where weekends mean farmers markets and trail walks, not traffic. Additional highlights include an EV charger, generator, and 25 years of careful stewardship. History, updates, and room to grow - all in one of Connecticut's most desired small towns

159 Cross Hwy, Redding

29 Lonetown Rd, Redding
$725,000
3 Beds ⋅ 3 Baths ⋅ 24195147 MLS
Welcome to 29 Lonetown Road, a timeless 1915 Colonial, where historic character, thoughtful updates and an extraordinary setting come together. Set on 1.5 picturesque acres, this lovingly maintained home has been cherished by the same family for more than 36 years and is ready for its next chapter. Inside, original hardwood floors, built-ins and beautiful period details create warmth and character throughout. The main level offers a gracious living room anchored by a stone fireplace, a formal dining room, and a stunning four-season sunroom filled with natural light. The large kitchen blends vintage charm with a commercial-inspired feel, featuring a 6-burner Garland range, center island, generous prep space, pantry with French doors, and easy access to both the bluestone patio and rear deck for indoor-outdoor entertaining. A convenient powder room completes the first floor. Upstairs, the spacious primary suite offers a light-filled retreat with an oversized bath featuring skylights, large walk in shower and dressing area, while 2 additional bedrooms share a full hall bath. Outside, enjoy spectacular sunsets, a peaceful brook winding through the property, enclosed vegetable garden and a detached 2-car garage. Across the street, the Lonetown Marsh Wildlife Sanctuary offers scenic walking trails, protected open space and year-round opportunities to enjoy nature just steps away. A rare opportunity to own a beautifully preserved piece of Redding history in an idyllic setting.

29 Lonetown Rd, Redding

4 Orchard Dr, Redding
$725,000
4 Beds ⋅ 3 Baths ⋅ 24131945 MLS
REQUEST FOR HIGHEST AND BEST. We've received multiple offers. Please submit your highest and best offer by Wednesday, Nov. 12th, at 7:00 PM. Welcome to 4 Orchard Drive, a charming retreat in the heart of Redding, CT. Nestled on a generous 2.5-acre lot, with a circular driveway, this home offers a serene escape, adjoining 6.5 acres of open space with a babbling brook and trails for hiking. The views are breathtaking. This delightful retreat features 4 bedrooms and 2.5 baths, 2 car gar. and fireplace;all perfect for comfortable living. The main level family room with no steps and a full bath, accessible from both the front door and patio-makes it ideal for aging in place. Enjoy hardwood floors throughout most rooms. Newer roof and fresh paint, ensures a move-in ready experience. Enjoy outdoor living on an expansive deck off of the kitchen and dining rooms. Additionally there is a slate patio off of family room. Perfect for entertaining year round or quietly soaking in the natural beauty. In a friendly neighborhood where homes rarely come on the market, this is a unique opportunity. This peaceful oasis is just 15 mins to the fabulous cultural arts center of Ridgefield. Additionally mins to Wilton and Westport, both ideal for shopping, dining, theater and more! Redding is known for their award winning schools, and their open space.

4 Orchard Dr, Redding

12 Granite Ridge Rd, Redding
$725,000
4 Beds ⋅ 2 Baths ⋅ 24099597 MLS
If a property located a short drive to conveniences including public transportation, Caraluzzi's market, the Mark Twain library, restaurants, and retail while situated in a quaint New England neighborhood appeals to you then this home is for you. With 4 bedroom's, 2 full bathroom's, this home features a sleek open-concept design, blending living space with effortless functionality. While each room is filled with natural light, the exterior is a sanctuary of natural and landscaped gardens. You will enjoy entertaining in the expansive 675 square feet open living room-kitchen, and dining area. Just outside the kitchen is a 20'x16' deck with exquisite views of the private backyard. The ground level floor plan offers flexibility with the possibility of an in-law suite. The recreation room and office can easily be returned to a 2-car garage. Set on a park-like 2-acre lot, the property sits on a quiet street ending in a cul-de-sac.

12 Granite Ridge Rd, Redding

Redding
$715,000
4 Beds ⋅ 3 Baths ⋅ 24182601 MLS
Welcome to this stunning 4-bedroom ranch home, nestled on 1.57 secluded acres while still being conveniently close to Georgetown Center, U.S. Route 7, and the train station. The main level features a cozy living room with a fireplace, a spacious kitchen with a dining area, and sliders that open to a large deck-perfect for outdoor entertaining. Enjoy the family room adorned with vaulted ceilings and skylights, along with three generous bedrooms, including a primary suite with a full bath. The lower level offers ample storage, a laundry area, and a versatile studio or in-law apartment complete with its own kitchen and laundry. Don't miss the detached 2-car garage, large parking area, potting shed, full house generator and garden to complete this beautiful property.

Redding

5 Iris Ln, Redding
$710,000
3 Beds ⋅ 2 Baths ⋅ 24165744 MLS
Set on a quiet cul-de-sac within a true neighborhood setting, this 3 bedroom, 2 bath ranch offers easy, one-level living on a beautifully flat .78-acre property, a rare find in Redding. Charming details throughout, including built-ins, multiple window seats, picture windows, and a wood-burning fireplace, create a warm and inviting atmosphere filled with natural light. The kitchen features a Sub-Zero refrigerator and direct access to the deck, making outdoor dining especially convenient. The primary bedroom includes an ensuite bath, while 2 additional bedrooms share the second full bath, providing comfortable space for guests, a home office, or hobbies. A partially finished lower level offers additional usable space, ideal for a gym, media room, or playroom. Central air, a classic ranch layout, and a two-car garage add everyday convenience, while the level yard offers outdoor enjoyment without the maintenance of a larger property. A wonderful alternative to condo living, this home combines charm, space, and the ease of single-level living. Welcome Home! OFFER DEADLINE TUESDAY 4/14 at 12pm.

5 Iris Ln, Redding

101 Sport Hill Rd, Redding
$705,000
2 Beds ⋅ 2 Baths ⋅ 24162857 MLS
Set behind a classic New England stone wall in highly desirable West Redding, this move-in ready home offers space, flexibility, and charm across 2,294 sq ft on the main level plus 952 sq ft in the finished lower level. Thoughtfully laid out and currently utilized as a 3-bedroom, the home includes a versatile additional room ideal for a bedroom, office, or guest space. Bright, open layout with hardwood floors and abundant natural light throughout. The main living areas feature two fireplaces and a wood stove, adding warmth and character, while multiple access points lead to the expansive back deck for seamless indoor-outdoor living. The oversized primary suite offers vaulted ceilings, ceiling fans, and direct deck access, creating a private, retreat-like feel. The finished lower level adds 952 sq ft of valuable additional space, including a recreation room with fireplace, along with a dedicated workshop, laundry area, and ample storage-ideal for recreation, hobbies, or a home gym. Step outside to a large deck with pergola overlooking a peaceful, wooded setting, offering privacy and space for entertaining or everyday enjoyment. Additional highlights include central air conditioning and a layout designed for comfort and functionality. Located in a town known for its top-rated schools, with convenient access to nearby train stations and major routes, making commuting to NYC and surrounding areas both practical and accessible.

101 Sport Hill Rd, Redding

27 W Woodland Dr, Redding
$675,000
4 Beds ⋅ 3 Baths ⋅ 24125735 MLS
Privacy, convenience, and timeless value, all in a truly special Redding setting. Welcome to 27 W Woodland Drive, a charming Colonial offering over 2,000 square feet of living space, tucked away at the end of a peaceful cul-de-sac in a neighborhood with minimal through traffic, offering a comfortable and welcoming environment. This four-bedroom, two-and-a-half-bath home provides the perfect blend of space and comfort. The main level features hardwood floors throughout, a spacious family room with a wood-burning fireplace, a dedicated living room or dedicated office space, an open kitchen with eat-in space that flows into the dining room, making it ideal for entertaining. Conveniently attached is the two-car garage which leads directly into the kitchen, making everyday living easy. Just off the kitchen, you will find laundry access and a deck overlooking the private backyard, perfect for gatherings or quiet relaxation. Upstairs, four generously sized bedrooms with ample closet space add comfort and character, while a walk-up attic provides easy access to storage. The unfinished basement with its own fireplace offers additional potential for future living space or recreation. All mechanicals less than 5 years old. Set on 1.2 private acres, this home offers the best of both worlds, a peaceful setting surrounded by Redding's natural beauty, yet only minutes to major routes: the Merritt Parkway, I-84, and Route 25, making daily commuting and weekend travel remarkably convenient.

27 W Woodland Dr, Redding

477 Newtown Tpke, Redding
$650,000
2 Beds ⋅ 2 Baths ⋅ 24134330 MLS
Welcome to this quintessential Connecticut Cape - an enchanting retreat on 2+ acres, a true gardener's paradise & nature lover's dream. Every room radiates warmth, light & joy, creating an instant sense of HOME. Step inside to find charm & comfort throughout - a spacious dining room with/ hardwood floors & a large picture window overlooking lush seasonal plantings. Living rm w/ cathedral ceiling, cozy fireplace, & sunlight year-round - perfect for cool New England evenings. Updated kitchen is a chef's delight w/ easy flow to the outdoors. When the weather warms, relax on the oversized screened-in porch overlooking manicured gardens, quiet stream & daily visits from birds & wildlife. On cooler days, sit by the porch fireplace & enjoy tranquil views in comfort - a space for every season. First-flr bedroom offers a serene retreat w/ sitting area, vaulted ceilings & floor-to-ceiling window framing breathtaking views of the property. Upstairs, primary suite w/ ample closets & private bath. Outdoors, mature landscaping, perennial gardens & stone pathways create a tapestry of color & texture. Multiple spots to sit, read, dine al fresco, or simply listen to the gentle brook. This Connecticut gem blends timeless charm w/ modern comfort - nestled in a quiet corner of Redding, offering peaceful country living yet close to all conveniences. Ideal as a full-time home or condo alternative - a truly special place to live, relax & entertain.

477 Newtown Tpke, Redding

18 Great Meadow Rd, Redding
$650,000
3 Beds ⋅ 2 Baths ⋅ 24099619 MLS
Welcome to 18 Great Meadow Road, a newly renovated home with a completely flat 2.5 acre lot on a quiet, cul-de-sac street. This house is the perfect combination of country side living but in a state of the art, almost new construction house. Although quiet and scenic, you are only 2 miles from the highly rated Joel Barlow high school and essentially in "central" Fairfield County close to all great neighboring towns. A completely new roof structure including new rafters, plywood and shingles creates the 14-foot cathedral ceiling resulting in a large bright and airy feel very similar to a brand new center hall colonial mansion. Right off the living room is a 4-season sunroom with baseboard heat and two brand new skylights providing year-round light and relaxation. Walk directly out the sunroom to the second level deck which overlooks the backyard, driveway and basketball hoop. The brand new kitchen from start to finish boasts high end, soft close, all wood cabinetry with ample storage including an 8ft pantry cupboard. The countertops are high end Quartz with an extra large center island that comfortably fits 4 or 5 large stools making it a complete eat in kitchen or the perfect spot for entertaining. All new appliances including a Frigidaire Gallery collection, smudge proof, stainless steel French door refrigerator as well as an ultra quiet third rack dishwasher and newly vented 3 speed hood range.

18 Great Meadow Rd, Redding

81-83 Picketts Ridge Rd, Redding
$650,000
4 Beds ⋅ 3 Baths ⋅ 24129044 MLS
TWO houses (#81 and #83) on peaceful over-an-acre property! Unique INVESTMENT Opportunity in Redding! Excellent for multi-generational family, investors or help subsidize your mortgage! Charming Colonial/Cape with detached COTTAGE/IN-LAW. Bright and spacious single family house in the quaint town of Redding. Main floor includes large living room with bay window and open floor plan into formal dining room. Sunlit eat in kitchen with door leading out to the quiet patio and deck overlooking scenic yard space. Main floor primary bedroom with ensuite and laundry as well as the second full bath which is newly renovated and finishes out the first floor. Upper level provides a spacious second bedroom, loft/third bedroom space and a small office nook/flex space. Many updates include: New electrical panel, new water filtration system, new gutters, paint, updated utilities and more. A two bay storage garage make this the perfect place to make home. Beyond the main house is the sweet one-bedroom cottage. Includes living area, new kitchen, bedroom and full bath, washer, dryer, gas heat, separate new septic system and private yard. Good commuting location via I-84/I-694/Rt.7 - Ridgefield restaurants & shopping 10 minutes away. Sherwood Island and Westport are easy 25 minutes (no highways!).

81-83 Picketts Ridge Rd, Redding

78 Black Rock Tpke, Redding
$635,000
2 Beds ⋅ 2 Baths ⋅ 24187187 MLS
Discover the quintessential Redding lifestyle in this charming circa 1898 home, perfectly positioned to enjoy the town's excellent schools, open space, and recreational opportunities like hiking, fishing, and kayaking. This 2/3 bedroom home (3rd bedroom being used as a study) also features and 2 full bathrooms, offering versatile living options, a 3-bedroom septic system, central air, updated electical system, thermo pride boiler with lifetime transferable warranty on the heat exchanger and a new shed in the yard. Step inside to discover timeless character with original hardwood floors and high ceilings. The living areas and 2 bedrooms are highlighted by four fireplaces-three decorative and one fully functional with a heater insert - adding warmth. The dining room boasts exposed beams, original leaded glass windows while newer windows throughout the remainder of the house ensure modern efficiency. Relax and unwind on the inviting covered and screened front porch. Need flexible space? The partially heated basement has been used as a home office, and a newer, spacious shed on the property offers endless potential as a workshop or a creative studio. Additionally, existing expansion plans-drawn up by previous owners-are available to help you visualize future possibilities (not submitted for town approval). Ideally located for an easy commute, you are just moments from Joel Barlow High School and the convenient shopping hubs of Bethel and Georgetown. Being sold "as is".

78 Black Rock Tpke, Redding

10 Shady Ln, Redding
$630,000
5 Beds ⋅ 3 Baths ⋅ 24135649 MLS
Charming Ranch-Style Home with In-Law Potential in Beautiful Redding awaits, if your are looking for your first home or your next one, opportunity knocks in the heart of Redding on a quiet cul-de-sac. This spacious & versatile ranch-style home offers the perfect blend of comfort, functionality, & small-town charm. Step inside the main level, where you'll find a warm & inviting sunken living room with a gas fireplace, hardwood floors, and plenty of natural light. The spacious eat-in kitchen is just waiting for your design ideas. This level also features 3 bedrooms and 2 full baths, providing comfortable one-level living. Downstairs, the fully finished walk out LL opens up a world of possibilities. With its own kitchen, full bath, living room with fireplace, 2 bedrooms, & an office this flexible space walk-outs to the backyard-perfect for use as an accessory apartment, in-law suite, guest quarters, or extended family living. Additional highlights include a 2-car garage, a private yard, and endless potential. Located on a quiet cul-de-sac take advantage of a wonderful opportunity to make this home your own with personal updates and touches. Located in the scenic and welcoming town of Redding, known for its award-winning schools, quaint town center, & over 17 beautiful town parks and nature preserves-you'll enjoy a lifestyle surrounded by nature, yet still close to major amenities. Schedule your private showing today and discover all that Redding living has to offer

10 Shady Ln, Redding

15 Old Mailcoach Rd, Redding
$610,000
2 Beds ⋅ 2 Baths ⋅ 24174036 MLS
THANK YOU FOR YOUR INTEREST. PLEASE SUBMIT HIGHEST AND BEST OFFERS BY TUESDAY MAY 26, 5:00PM. Discover a storybook sanctuary nestled in the heart of Redding, CT. This charming, vintage Cotswold inspired cottage provides a magical retreat that feels worlds away, yet remains perfectly connected. Situated on a lushly landscaped 2.3 acre property, the grounds are a gardener's dream featuring a tapestry of vibrant perennials with mature flowering shrubs and trees. Grow your own produce in the fenced-in vegetable garden or enjoy the serene sounds of nature by your own private pond with babbling brook and charming footbridges. The lovely stone patio is your front row seat to the beauty of the grounds, making it the perfect setting for quiet reflection or dining al fresco. The 1,481 sq. ft. interior features 2 bedrooms and 2 baths plus a large living room with expansive views of the property. Ceiling beams and a fieldstone fireplace add to the charm. There is a large eat-in kitchen with lots of room to customize. While this home does need some updating, recent improvements provide peace of mind, including a new roof and gutters, new windows and a new septic system. This home provides a captivating opportunity whether you are looking for a weekend escape or a permanent residence. This is an estate so there are no disclosures. Sale is not subject to probate approval. SOLD STRICTLY AS IS.

15 Old Mailcoach Rd, Redding

9 Apple Ln, Redding
$579,350
3 Beds ⋅ 2 Baths ⋅ 24173981 MLS
SUBMIT HIGHEST & BEST OFFER BY NO LATER THAN TUESDAY 5/26 AM. ATTORNEY INSISTS ON PLAIN LANGUAGE OFFER. SEE DOCUMENTS: OTHER (1st document) Perched proudly on a mature level 1.3 acres, boasting flowering dogwoods, giant red maples and towering pines is this well cared for 3-bedroom 2-bath Ranch on a quiet cul-de-sac yet so convenient to Georgetown shopping, restaurants, Metro train and commuting roads. Sunny living room with fireplace is open to the dining room, both with large window walls, and next to the eat-in kitchen. Three bedrooms and tub bath complete this level. The basement adds 912 sq ft per the Vision Appraisal field card (see other in documents) It includes a family room with gas log fireplace, office/den, washer & dryer room and basement combination entry & entertainment area with wet bar and shower bath, which accesses the enclosed porch breezeway which leads to the attached 2 car garage as well as to the front and back yards. There is a storage attic area over the garage best accessed from the back. Bring your creative decorating and remodeling ideas and make this gem shine. Revel in the gorgeous land, perfect for gardening and numerous activities with room for a pool. PLEASE NOTE: This property is in an estate and there is no property condition report. However, the mechanicals appear to be newer and well cared for which you can easily see in the basement. NOTE: This property is being sold "AS IS".

9 Apple Ln, Redding

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