Windham County, CT Real Estate | Windham County, CT 4 Bedroom Homes for Sale

Investors Take Notice! Bring your vision and unlock the potential of this Victorian-style two-family property at 55 Main Street in Willimantic. Each unit offers 2 bedrooms and 1 bath, with both bathrooms recently updated with brand-new finishes. While the property would benefit from additional updating and improvements, the opportunity to build equity and maximize its potential is well worth exploring. Ideally located across from Recreation Park, near Eastern Connecticut State University and UConn, and within walking distance to local amenities and the bus line. Whether you're an investor seeking your next project or an owner-occupant looking to offset your mortgage with rental income, this property offers exciting possibilities. Bring your ideas, envision the possibilities, and schedule your showing today!

55 Main St, Windham

$439,000

4 Beds ⋅ 2 Baths ⋅ 24216685 MLS

Tucked away on 2.27 picturesque acres, this beautiful Colonial offers a wonderful combination of privacy, comfort, and country charm! Set well back from the road and surrounded by mature trees, this inviting 4-bedroom, 2-full-bath home offers 1,862 sq. ft. of bright, welcoming living space. Inside, discover beautiful hardwood floors, tasteful finishes, and an abundance of natural light. The attractive kitchen features granite countertops, stylish cabinetry, tile backsplash, and stainless steel appliances. The comfortable living room includes a masonry chimney with woodstove hookup, perfect for creating a cozy gathering space. A particularly desirable feature is the first floor bedroom and full bath, offering flexibility for convenient main-level living or a wonderful home office with peaceful yard views. Sliders from the dining room lead to a spacious deck, ideal for outdoor dining, entertaining, or simply enjoying the natural surroundings. Upstairs are three additional bedrooms and a full bath. The semi-finished basement offers terrific bonus space for a rec room, home gym, hobbies, home office, or more, along with additional storage. A detached 1-car garage/outbuilding completes the picture. Beautifully maintained, thoughtfully presented, and ready to enjoy!

92 Brooklyn Rd, Canterbury

$349,900

4 Beds ⋅ 1 Baths ⋅ 24213064 MLS

Step inside to find hardwood floors throughout, creating a warm and cohesive feel across the home. The updated bathroom and kitchen adds a fresh, modern touch, while the functional layout provides flexibility for family living, guests or a home office. Major improvements have already been taken care of, including a brand-new gas forced air heating system offering an easy conversion to add central air for year-round comfort.The seller removed the hot water baseboard oil system and replaced with the gas forced air heat so he would have the ability to add central air if he wanted to in the future. A new septic system installed in 2023 offers peace of mind for years to come. Outside, enjoy a spacious fenced-in-yard perfect for pets, entertaining or relaxing in privacy. The large back deck extends your living space outdoors and is ideal for gathering, grilling or quiet evenings. Conveniently located close to the MA line with easy access to I-395, this home is perfect for commuters while still offering a peaceful residential setting. Don't miss this opportunity to own the well-updated ranch in a highly accessible location, SHORT SALE being done by Sean Wilder.

18 Leon St, Thompson

$735,000

4 Beds ⋅ 4 Baths ⋅ 24215553 MLS

Some homes just feel like home the moment you arrive, and 48 May Brook Road is one of them! Nestled in one of Woodstock's most desirable neighborhoods, this charming Colonial offers 3,537 square feet of thoughtfully designed living space, picturesque views, and sunsets you'll never grow tired of. A welcoming farmer's porch sets the tone, while the beautifully maintained grounds create an unforgettable first impression. Inside, the main level features an open-concept kitchen with walk-in pantry, dedicated dining area, two spacious living areas including one with a cozy gas fireplace, a private home office, and convenient first-floor laundry. Upstairs, you'll find four generously sized bedrooms and two full bathrooms. The finished walkout lower level offers incredible flexibility with an additional bedroom, full bathroom, media room with equipment included, ample storage, and potential in-law accommodations! Step outside to enjoy the expansive deck overlooking Connecticut's Quiet Corner, beautifully manicured grounds, a storage shed, and even a batting cage! Located within the Woodstock school district, this property offers the perfect combination of comfort, space, and New England charm. Homes like this don't come around often.

48 May Brk, Woodstock

$519,900

4 Beds ⋅ 4 Baths ⋅ 24215433 MLS

Beautifully Remodeled Home with Modern Updates & Separate In-Law Living! Welcome to this beautifully renovated home offering the perfect combination of modern comfort, spacious living, and versatility! Thoughtfully updated throughout, this home features an inviting layout designed for today's lifestyle. The main living area offers 3 spacious bedrooms, 2.5 bathrooms, and a dedicated home office. The bright, open-concept kitchen, dining, and living areas create a seamless flow, perfect for everyday living and entertaining. Convenient main-level laundry adds to the home's functionality. A separate in-law living area provides an excellent opportunity for multigenerational living, extended family, or guests. This private space features 1 bedroom, 1 full bathroom, its own laundry area, and a comfortable living space, all conveniently located on the first floor. Extensive renovations throughout, including a new roof and new furnace, offer added value and peace of mind. Step outside to enjoy the spacious deck, ideal for outdoor entertaining, relaxing, or hosting summer gatherings. The property also features two detached garages, including an oversized heated garage offering exceptional space for vehicles, storage, a workshop, or hobbies. With its beautifully updated interior, flexible living arrangements, and impressive garage space, this property offers something for everyone. Move-in ready and full of possibilities-schedule your private showing today!

33 Machine Shop Hill Rd, Windham

$339,900

4 Beds ⋅ 2 Baths ⋅ 24214694 MLS

Antique charm, meaningful updates, and a backyard alive with nature-this four-bedroom, two-bath Cape offers something special inside and out. A beautiful neighboring pond and wildlife visiting throughout the year create a memorable setting, with a spacious backyard offering room to garden, gather, or simply enjoy the outdoors. Inside, the generous eat-in kitchen features country-style cabinetry, plentiful counter space, and room to come together over a meal. The kitchen flows into a spacious living room, while a first-floor bedroom and bathroom offer flexibility for everyday living. A rear mudroom with a conveniently located laundry area provides a practical entrance from the backyard. The tastefully renovated upstairs reflects the care invested in this home. Updates over the past several years include a newer roof, newer windows, and recently painted exterior, along with additional renovation work that goes beyond cosmetic finishes. From its welcoming kitchen to its natural surroundings, this Cape offers character, space, and the opportunity to make it your own. Come experience the home-and the setting-that photographs can only begin to capture.

100 Rhode Island Line Rd, Putnam

$655,000

4 Beds ⋅ 4 Baths ⋅ 24212443 MLS

Welcome home to this impressive 4-5 BD, 3.5 BA custom Colonial set on 1.85 acres in desirable Killingly setting! Offering generous living space, exceptional versatility, & outdoor amenities, this home is designed for comfortable living & entertaining. Step inside to discover beautiful hdwds throughout dining room, great room, & den. Spacious kitchen is sure to impress with granite, stainless appliances, & breakfast bar-perfect for morning coffee, casual meals, & gathering with family & friends. Gas FP adds warmth & ambiance, while the expansive great room features a vaulted ceiling & sliders leading to a large deck with pergola overlooking the inviting in-ground pool with new liner. Primary suite offers a relaxing retreat with an ensuite bath featuring whirlpool tub, double sink vanity & walk-in closet. Three additional light-filled bdrms provide room for family, guests, or a home office. One of this home's standout features is the large bonus room above the garage with its own private entrance & full bath-ideal for extended-stay guests, teen hangout, or flexible living space. Outside, enjoy your own private retreat with a fenced yard, firepit, & raised garden beds. Three storage sheds, with electricity, provide space for equipment & storage. RV pad with 30-amp electric. 2-car heated garage with multiple shelves & cabinets. C/A, oil heat, generator ready, new well pump tank, new washer & dryer, & mounted TVs & surround sound system. Make this exceptional home yours!

367 Mashentuck Rd, Killingly

$217,500

4 Beds ⋅ 1 Baths ⋅ 24213182 MLS

Charming Antique Colonial - Prime Windham Location Step back in time and experience the warmth and character of this classic 1915 Antique Colonial, beautifully situated on a desirable corner lot in Windham. This inviting home offers four spacious bedrooms and one full bath, along with a generously sized living room perfect for relaxing or entertaining. The bright eat-in kitchen provides a welcoming space for gatherings and everyday living. Enjoy peaceful mornings or cozy seasonal evenings in the sun-filled three-season room, complete with stairs leading directly out to the backyard. The property is surrounded by a charming white picket fence, enhancing its timeless New England appeal. A standout feature is the impressive two-story garage with access from two streets, offering exceptional convenience, storage, or potential workshop space. The full walk-out lower level adds additional functionality and flexibility. Ideally located close to local colleges, this property presents an excellent opportunity for investors, owner-occupants, or those seeking rental potential. Enjoy nearby delicious eateries, unique shops, and easy commuting access to surrounding towns and major routes. This is a truly charming and classic New England home that must be seen to be fully appreciated.

129 Walnut St, Windham

$329,900

4 Beds ⋅ 2 Baths ⋅ 24212685 MLS

What started as just a summer cottage has been transformed over the 50 years of ownership into a great lake view & access home. This home features over 1,700 sq. ft. on two floors, 4 total bedrooms along with 2 full bathrooms. The first floor has a large living room with pellet stove heating that satisfies the major of the heating needs. There is a good working space kitchen along with a rear sunroom/plant room/dining area. There are two bedrooms, a full bathroom with tub/shower along with the laundry on the main level. The second floor was a full addition years ago. There are two very good-sized bedrooms, a sitting area/den, along with an additional full bathroom. You will even find a second story open deck for enjoying nature. Home features a full walk-up attic with good access & storage. The basement, once just a small crawl space, was excavated out and a block foundation was installed. A propane warm air heating system, propane water heater, along with an additional chimney flue for woodstove can be found. Home has deeded access & lake rights to Lake Bungee and is just walking distance from private beaches and boat launches.

101 Beaver Dam Rd, Woodstock

$329,000

4 Beds ⋅ 2 Baths ⋅ 24211232 MLS

Perfect for a first-time homebuyer looking to offset housing costs with rental income. Live in one unit while the tenant helps pay the mortgage. This two-family home offers 2 bedrooms, 1 full bath, a kitchen, living room, and an enclosed front porch. Several recent updates include a NEW ROOF, a NEW GAS HOT WATER HEATER, NEW CARPETING, and a REGLAZED TUB and SINK. Each unit features plenty of off-street parking and a one-car garage. Each unit has its own utilities, NATURAL GAS for heat. The full basement includes washer and dryer hookups and offers plenty of storage space. An enclosed rear porch at ground level leads to a private backyard. Conveniently located, close to downtown, shopping, restaurants, and local amenities, this property combines affordability, comfort, and income-producing potential. A great opportunity for first-time buyers, owner-occupants, or investors looking to build equity while generating rental income.

25 Gilman St, Putnam

$550,000

4 Beds ⋅ 2 Baths ⋅ 24211512 MLS

*MOTIVATED sellers, bring offers* Welcome to this spacious 4 Bedroom Cape, offering a versatile floor plan with plenty of room to spread out, this home blends classic character with thoughtful updates. The main level features beautiful hardwood floors and an inviting eat-in kitchen with a center island and cooktop, wall oven, and plenty of space for everyday meals. A separate dining room, comfortable living room, & additional sitting room provide multiple gathering spaces, with the sitting room offering flexibility as a home office, den, or reading room. Two beautifully remodeled full bathrooms add modern style and convenience, one with radiant heat floors. Upstairs, you'll find four generously sized bedrooms plus a charming hallway nook that offers additional flexible space for a desk, study area, fitness equipment, or hobbies. Loads of closets everywhere! Brand new roof & Skylights offer additional value. Set on 1.7 acres with room to enjoy the outdoors, this property is conveniently located near a golf course, parks, bike trails, and area private schools. A wonderful opportunity to enjoy space, versatility, and the beauty of Pomfret living!

248 Paine Rd, Pomfret

$790,000

4 Beds ⋅ 2 Baths ⋅ 24209026 MLS

Set high above the road at approximately 900 feet in elevation, this beautifully maintained home combines privacy, natural light and a versatile floor plan in a picturesque setting. Southwestern exposure fills the home with sunlight, while the two-story entry and catwalk overlooking the dramatic living room create an impressive sense of space. The living room features a woodstove and direct access to the covered back deck, creating an inviting connection to the outdoors. A charming three-season sunroom at the front of the home provides another bright and comfortable space to enjoy the surrounding setting. The main level offers convenient one-floor living with two bedrooms, a full bath and a laundry room with both exterior and garage access. There is no carpet in the home-hardwood and tile run throughout. Upstairs, the private primary bedroom suite is joined by an additional bedroom and a flexible office/library/den. An unfinished walk-out basement provides excellent storage and plenty of potential for future finished space or possible in-law accommodations. Well insulated with 12-inch foundation walls, a dry basement, good drainage and excellent well water. Enjoy the privacy of the property while being just down the road from the approximately 8,000-acre Yale-Myers Forest with miles of trails and outdoor recreation. Conveniently located only 1 mile to I-84, with easy access to Hartford and approximately one hour to Boston and two hours to New York City.

183 Hillside Rd, Ashford

$625,000

4 Beds ⋅ 3 Baths ⋅ 24210501 MLS

The Benjamin Bosworth House has been part of Eastford's landscape for more than two centuries, and there is still nothing quite like it. Set on 3 acres, this Federal-style home, completed around 1800, offers 4,538 square feet, 4 bedrooms, 2.5 baths and 11 fireplaces. Its defining feature is a rare full-height monitor, once used as a Masonic meeting hall, with built-in benches and fireplaces. Throughout the house, hand-carved woodwork, historic finishes and generously scaled rooms tell the story of its past. The main level includes a formal dining room, parlor, sunlit sitting room, kitchen, studio and workshop, with additional flexible space upstairs. Since purchasing the home in May, the current owner has continued restoration work, including new lime plaster in the parlor and second-floor hall, a retiled upstairs bath and fresh paint in several rooms. Listed on the National Register of Historic Places, this is a remarkable opportunity for someone who appreciates early American craftsmanship and wants to carry its story forward.

89 John Perry Rd, Eastford

$389,900

4 Beds ⋅ 2 Baths ⋅ 24209361 MLS

OVERSIZED Cape w/ NEW FLOORING throughout main level on the end of a cul-de-sac w/ CITY WATER & SEWER! 4 BEDROOMS- 2 LARGE bedrooms upstairs (one has a WALK IN CLOSET) REMODELED bathroom w/ TILE flooring, updated vanity and tub w/ TILE back splash. 2 additional bedrooms on first floor, UPDATED bathroom w/ NEWER toilet and VANITY. SPACIOUS living room, eat in kitchen w/ LARGE ISLAND NEW BOSCH dishwasher, stove & microwave conveying. SLIDER leads to 10 x 12 DECK overlooking .70 of an acre. GENERATOR 8000 WATT will CONVEY for peace of mind during storms. SOME furniture WILL BE CONVEYING. PAVED driveway w/ plenty of parking and ! CLOSE to 395 for easy commute. 28 x40 BASEMENT for ALL your storage. CAN CLOSE ANYTIME! Camera & Audio inside and out.

66 High Meadow Dr, Plainfield

$449,900

4 Beds ⋅ 2 Baths ⋅ 24209513 MLS

Welcome to 78 Hammond Hill Road, a charming New England Cape set on approximately 1.7 picturesque acres in peaceful Hampton Connecticut. This inviting four-bedroom home offers about 2,000 square feet of living space, surrounded by mature landscaping and beautiful countryside views. Enjoy summer days by the in-ground pool, relax overlooking the rolling wooded hills, or explore the spacious grounds and private pond. A detached two-car garage, solar, and additional unfinished space with in-law potential add versatility. This is a wonderful country retreat offering privacy, character, native plants, fruit trees and a quaint private pond. The attached in-law apartment is adjoining and shares the quintessential northeastern Connecticut scenery of Hammond Hill.

78 Hammond Hill Rd, Hampton

$400,000

4 Beds ⋅ 2 Baths ⋅ 24208690 MLS

Vintage 1944 home in the heart of Dayville, set on 2.5 acres at a convenient corner location close to shopping and with easy highway access, close to the Mass & RI lines. The attached garage provides convenient access to the home. The quaint kitchen features cozy bench seating, built-in glass-front storage perfect for displaying collectibles, and a door leading to the screened front porch-an inviting spot to enjoy morning coffee and the changing seasons. The spacious living room offers a sunny bay window, sliders to a private rear patio, hardwood floors, and a cozy fireplace creating a warm and inviting gathering space. The first floor includes a primary bedroom, an additional bedroom or office, and a full bath. Upstairs are two generously sized bedrooms, a large hallway closet, and another full bath. A detached outbuilding offers versatile space for a studio, workshop, or hobby area. Being sold AS IS, this solid home offers an opportunity to bring your vision and updates while preserving its vintage charm and character.

10 Homestead Rd, Killingly

$393,000

4 Beds ⋅ 2 Baths ⋅ 24209373 MLS

Welcome to this inviting 4-5 bedroom, 2-bath Colonial in the heart of Danielson, CT. Set on a generous .35-acre lot with 1,904 square feet of living space, this two-story home blends classic charm with everyday comfort. Gleaming hardwood floors run through the kitchen, living room, and dining room, while the sun-filled living room addition, built in 1999, adds extra space to spread out. The kitchen was refreshed about eleven years ago with new cabinets and countertops, and nearly every appliance has been updated in recent years, with the exception of the microwave. Siding and windows were replaced in 2007, the roof is roughly eleven years old, and the furnace is about 2 years old, meaning many of the big-ticket updates are already done. Upstairs, the bedrooms feature carpet and paint that were refreshed within the past couple of years. Additional highlights include a detached 2-car garage and a walk-up attic filled with natural light from its front-facing windows, perfect for storage or future finished space. Outside, enjoy a large back deck and a fully fenced yard. All of this in a peaceful residential neighborhood with easy access to local roads and amenities. This home truly offers the perfect mix of comfort and convenience.

85 Robertson Ave, Killingly

$399,900

4 Beds ⋅ 2 Baths ⋅ 24209211 MLS

Step into this beautifully maintained 1885 home full of charm and character. The home is in great condition, with updates of roof, exterior paint, windows, wood floors, boiler and electric panel. Crown molding and high ceilings throughout the main level combine to add warmth and flair. A formal living room, family room with built-ins, and large dining area accommodate entertaining, or relaxed living. The primary bedroom suite is on the 2nd level, and features a sitting area, propane fireplace, walk-in closet, and full bath. Host the next gathering on the wrap around porch, complete with haint blue ceiling, or just sip apple cider with a friend. The barn provides great space for storage, hobbies or a workshop. After 50 years, this property is ready for it's next owner.

225 Woodstock Ave, Putnam

$429,900

4 Beds ⋅ 2 Baths ⋅ 24207831 MLS

249 Pond Hill Road, Moosup, CT Discover relaxed water-community living in this beautifully renovated ranch offering just under 2,000 sq. ft. of finished living space with seasonal views of Moosup Pond. Just a short distance from the community beach and boat launch, enjoy convenient access to swimming, boating, fishing, and all that pond life has to offer. Bright and inviting, the main level features an open-concept kitchen, dining, and living area filled with natural light and complemented by refinished hardwood floors. The updated kitchen offers quartz countertops, brand-new appliances, generous cabinetry, and a spacious center island ideal for everyday living and entertaining. A main-level primary bedroom, two additional bedrooms, and a beautifully renovated full bath complete this floor. The fully finished walkout lower level provides even more versatile living space with a generous family room, additional bedroom, second full bath, and dedicated laundry room. Outside, an expansive wraparound deck creates the perfect place to relax, entertain, and take in the peaceful surroundings and water views. Move-in ready and conveniently located near major routes, shopping, and restaurants, this thoughtfully renovated home combines modern updates, flexible living space, and the appeal of the Moosup Pond lifestyle.

249 Pond Hill Rd, Plainfield

$379,900

4 Beds ⋅ 1 Baths ⋅ 24207835 MLS

Welcome to the Benjamin Clarke House - a grand 1700s center entrance colonial located on a 2-acre country lot - complete with rolling lawn, gardens, restored shed and a pond. Spacious house with much restoration complete - 2 upstairs rooms and a bathroom still to be completed by the new owners. Charm and warmth prevail in this beautiful home, including wide board floors, fabulous stone fireplaces, 1st floor laundry and a woodstove. Poured concrete and stone foundation. A 1-car garage completes this lovely property.

19 North Rd, Ashford

$1,425,000

4 Beds ⋅ 5 Baths ⋅ 24205041 MLS

Set amid nearly 120 acres across four deeded lots, this impressive Woodstock property offers an exceptional combination of privacy, space and versatility. The stately Colonial features over 5,000 sq. ft. of living space with 4 bedrooms, 4.1 baths and 12 rooms. A grand two-story foyer leads to a dramatic two-story living room with soaring ceilings and abundant natural light. The spacious kitchen offers extensive cabinetry, granite countertops, stainless steel appliances, a large center island and adjoining dining area with access to the deck. The primary suite features a tray ceiling, walk-in closet and private bath with double vanity, soaking tub and separate shower. A finished walk-up third floor provides flexible bonus space for a home office, recreation room or additional living area. Adding even more versatility is a detached in-law/guest apartment with a separate entrance, kitchen, living area, bedroom, full bath and laundry. Three additional deeded lots are included with the main parcel, bringing the total offering to nearly 120 acres-a truly unique opportunity to enjoy space, privacy and the natural beauty of Woodstock.

329 Rte 198, Woodstock

$679,000

4 Beds ⋅ 3 Baths ⋅ 24202453 MLS

Discover the timeless charm and endless potential of this antique home in Woodstock located down the hill from Woodstock Academy. Situated on a lovely country road while remaining close to all amenities. Entering through the side door into a lovely sitting/dining area with fireplace that opens to the kitchen, which flows into a large living room, perfect for gathering family or entertaining. There is plenty of space for a home office or den too. Head upstairs where there are 4 spacious bedrooms, the primary having its own dressing room, along with 2 full baths. Lovely wood flooring throughout the home. Rich with character and antique details, this special property offers a wonderful opportunity to refresh, restore and make it all your own. Set 8.5 acres, the grounds provide plenty of room for gardening, agriculture and animals or just a quiet place to relax. The beautiful post and beam barn adds character and versatility, while providing the foundation for hobbies, storage, or animals. Come and discover all the amazing features and opportunities this home has to offer!

122 Child Hill Rd, Woodstock

$595,000

4 Beds ⋅ 3 Baths ⋅ 24204008 MLS

Modern amenities meet unmatched seclusion in this 2,000+ sq ft colonial. A mostly level lot offers abundant green space, fruiting plants, and perennials, while the side deck and yard open to a beautiful natural view of the Still River-ideal for outdoor entertaining or quiet, serene living. Inside, gleaming maple floors lead to a first-floor bedroom with attached pass-through bath, a modern eat-in kitchen with double wall ovens and a propane stovetop, a large dining room, and a spacious living room with a functional fireplace. Upstairs, a hallway full bath serves three additional bedrooms, including the primary suite with its own attached full bath. The walk-up attic's excellent ceiling height and volume create a strong opportunity to add livable square footage. The basement's layout and ceiling height are equally well suited to finishing and expanding the home further. An attached two-car garage and paved driveway provide ample parking. If you want modern comfort, privacy, and room to grow in a peaceful woodsy setting, this is the home for you!

47 Sherman Rd, Woodstock

$290,000

4 Beds ⋅ 2 Baths ⋅ 24201649 MLS

INVESTOR OPPORTUNITY IN WILLIMANTIC! Bring your vision to 86 Chestnut Street, an approximately 1,560 SF multifamily property. Originally built in 1887, the property offers timeless architectural character and charm rarely found in newer construction. Conveniently located near downtown Willimantic, Eastern Connecticut State University, shops, restaurants, services, and major area routes. Offered AS-IS, providing an opportunity to renovate and customize to your investment strategy. The property's character, layout, location, and value-add potential make this an excellent opportunity for an investor or owner-occupant. Cash or conventional financing only. No government financing. Buyer to conduct their own due diligence regarding condition, zoning, intended use, and renovation potential.

86 Chestnut St, Windham

$179,999

4 Beds ⋅ 2 Baths ⋅ 24201064 MLS

Bring your vision to this four-bedroom home in Willimantic's Hill Section. With approximately 1,807 square feet of living space, the property features generously sized rooms, tall windows, original woodwork, and period details throughout. With thoughtful updates, this home has the potential to showcase its original character while being tailored to its next owner. Conveniently located near downtown Willimantic, Eastern Connecticut State University, shopping, dining, and major routes. Property is being sold as-is. Also available is 11 Bellevue Street, located behind the property, creating the possibility of a package purchase. One of the parties to the LLC has an active real estate license.

15 Bellevue St, Windham

$1,250,000

4 Beds ⋅ 5 Baths ⋅ 24199467 MLS

Privately tucked away in a serene setting, this exceptional 2022 custom-built residence offers a rare blend of luxury, privacy and everyday comfort. Thoughtfully designed, the home features 4 bedrooms plus expansive finished living space above the garages, offering flexibility for extended family, guests or private retreats. One area was previously used as a private living suite with a bedroom, separate living area and full bath-ideal for guests or multi-generational living. Additional finished spaces include a dedicated movie room and newly added loft. Outside, enjoy your own resort-style escape with an in-ground pool, fully fenced pool area, custom concrete work and fire pit. A long private driveway with underground utilities creates an impressive approach, highlighted by a professionally crafted rock wall at the entrance, with the matching opposite side underway. Mini-splits provide efficient year-round heating and cooling. Located close to Connecticut National Golf Club and surrounded by scenic natural beauty, the property offers access to exceptional outdoor recreation and prime hunting opportunities. Modern construction, versatile living spaces and an incredible sense of seclusion make this more than a home-it's a private lifestyle retreat. A truly rare offering that must be experienced in person. Agent-owned property.

44 Blood Rd, Putnam

$449,900

4 Beds ⋅ 2 Baths ⋅ 24199139 MLS

This exceptional 1740 antique cape is set on a lovely 1.59 acre property with stonewalls. The home has been beautifully maintained, and is in immaculate, move-in condition! The first floor features a bright, sunny kitchen with a walk in pantry, a large dining room, a living room with woodstove, a sitting room, and a home office. The woodstove was installed in 2025, and adds coziness and warmth to the home. Another highlight of the first floor is a beautiful butler's pantry with custom built-ins. There is also a main level full bath with laundry. The second floor has 4 bedrooms, a full bath, and a large walk in attic area for storage. Other features include a lovely screened in back porch, two barns which would be perfect for a hobby farm or a workshop/studio, and an above ground pool. The spacious, private back yard has a large garden area with perennial plants, two raised beds, and four newly planted fruit trees. Recent updates include a new roof in 2025 with a warranty which will convey, a well pump installed two years ago, a new chimney cap, and many new replacement windows. This home is filled with charm and character, and has a great flexible floor plan. Schedule a time to view this exceptional Brooklyn property!

136 Hartford Rd, Brooklyn

$449,999

4 Beds ⋅ 3 Baths ⋅ 24197506 MLS

Investors, take notice! This antique Colonial is situated on an impressive 6.6-acre private lot offering a peaceful setting and endless potential. A portion of the acreage is already cleared, while the property also features three beautiful ponds and plenty of outdoor space to enjoy the tranquil surroundings. Inside, the home offers 4 bedrooms, 3 full bathrooms, and a walk-out basement, providing plenty of space and flexibility for future improvements. A brand-new 200-amp electrical service is already in place, along with a newer heating system, approximately 4 years old, giving the next owner a great start on bringing this property back to life. The home is in need of TLC and updating, but with its antique Colonial character, spacious layout, beautiful acreage, and private setting, the possibilities are plentiful. Whether you're an investor searching for your next project or an owner occupant looking to restore an antique home and create something special, this property is ready for your vision. Schedule your showing today and discover its full potential!

128 Holmes Rd, Pomfret

$749,900

4 Beds ⋅ 3 Baths ⋅ 24197545 MLS

Motivated Sellers! 4.8 Acres total. 2 Beautiful apartments and a large commercial space plus post & beam barn, greenhouse & patios galore! Fully renovated in 2021. 4.8 acres includes additional 1 acre residential lot. Blends historic post-and-beam character with modern updates, offering residential living plus studio, workshop, office, brewing, and creative spaces. Residential areas feature exposed posts and beams, wide-plank pine floors, shiplap, barn doors, butcher-block shelving, and cathedral ceilings. Kitchens include custom hickory and white shaker cabinetry, large center island, leathered granite counters, farmhouse sinks, stainless appliances, and matte-black fixtures. One area was a former display kitchen; renovations added a bedroom, large closet, and living space. Commercial, first floor temperature-controlled space. Walkout basement has concrete floors, substantial storage, multiple exterior doors, and ~8-ft ceilings. Systems include mini-splits, natural-gas heat, second-floor air handler, three-phase power, newer electrical panel, hybrid heat-pump water heater, UV filtration, new well pump, spray-foam insulation, and updated PVC plumbing. Exterior offers greenhouse/sunroom, pergola, large paver area, extensive newer decking, storage shed, private well, and multiple walkouts. Owner estimates parking for ~50 vehicles. Original cupola available for reinstallation.

16 Main St, Plainfield

$459,900

4 Beds ⋅ 2 Baths ⋅ 24194052 MLS

Great single family home with an extra home on property. Level lot. Lots of opportunity to live or invest. Sale includes 683 Norwich Rd.

Plainfield

$499,900

4 Beds ⋅ 3 Baths ⋅ 24194484 MLS

Discover the space and comfort you've been searching for in this sprawling 4-bedroom, 3-full-bath ranch set on a picturesque 3-acre lot. Designed for both everyday living and entertaining, this home offers a spacious layout with both formal and informal living rooms, giving everyone room to relax. The inviting kitchen flows seamlessly into the dining room, where a cozy fireplace creates the perfect gathering space. Step outside to the expansive back deck, accessible from both the kitchen and the primary bedroom, and enjoy peaceful views of the surrounding property. The spacious primary suite features a private full bath and an impressive walk-in closet. Recent updates provide peace of mind and modern appeal, including a new roof, new furnace, new flooring, and beautifully remodeled bathrooms with new vanities, toilets, and a shower insert. Car enthusiasts, hobbyists, or those needing extra storage will appreciate the attached two-car garage, as well as an additional garage located behind the home. With three acres of beautiful land offering endless possibilities for outdoor enjoyment, this property combines privacy, functionality, and comfort in one exceptional package. Schedule your private showing today!

137 Ference Rd, Ashford

$699,900

4 Beds ⋅ 3 Baths ⋅ 24193491 MLS

56 expansive ACRES of pristine Connecticut COUNTRYSIDE with quiet rural atmosphere. Space for HUNTING wildlife viewing and trails. Recreational Haven, Homestead with enough room for FARMING and timber. ENORMOUS 2400 square-foot GARAGE/WORKSHOP with 12 x 12 doors HEATED with two zones, office with a full bathroom and additional bathroom and its OWN Septic! DETACHED two car garage with (two NEW doors) next to a ONE of a KIND almost 3000 square-foot Country home with BEAUTIFUL CRAFTMANSHIP throughout with CUSTOM STONE fireplace in the large living room with a second FIREPLACE in the dining/custom kitchen (new oven and microwave) area for entertaining with an ambience and 1/2 bath laundry area. Upper level has primary bedroom suite and three additional bedrooms with two full bathrooms. 2 brand NEW mini splits $15,000, two NEW wood stoves and piping $14,000, two NEW well pumps $10,000, NEW spray foam and attic $18,000, 10 NEW windows, two NEW front doors and exterior doors $20,000. Peace of mind with a brand NEW GENERAC generator 24,000 Watts $12,000, newer heating system and updated electrical panels NEW $10,000 kennel for the animals.*** Natchaug Forest is across the street***CAMERAS and AUDIO and OCCUPIED-DO NOT GO ON PROPERTY without LISTING AGENT-THANKYOU

233 Fire Tower Rd, Pomfret

$499,000

4 Beds ⋅ 3 Baths ⋅ 24192773 MLS

Almost new! Built in 2025 this stunning raised ranch is move- in ready. The bright, open concept main level features a living room and kitchen with cathedral ceilings and spacious primary suite, 2 additional bedrooms and an additional full bathroom. The fully finished lower level adds a versatile bedroom, another full bathroom-ideal for guests, hobbies, or a home office. The oversized, integrated 2 car garage includes built-in shelving and a dedicated utility room. Inside the entry, a handmade coat rack with bench creates a warm, custom welcome for you and your guests. This home is packed with upgrades including: quartz kitchen countertops, large island with seating for 3, coffee bar/glass front cabinetry, oversized pantry and full privacy tempered glass door leading to the deck. Each bedroom has a custom closet design system to maximize space. All windows have custom shades/blinds. Nuvo whole house water filter system. A beautifully finished, thoughtfully designed home with quality touches at every turn

48 Lake St, Plainfield

$949,900

4 Beds ⋅ 2 Baths ⋅ 24189396 MLS

Four heated garage bays. Over 12 private acres. A brook with its own dam. This is a rare opportunity to own an updated home with an exceptional workshop and endless room to live, work, and play. The heated and air-conditioned garage features four bays, an office loft, air compressor, and dedicated paint bay. Whether you're restoring cars, operating a trade business, storing equipment, or simply need premium workspace, this setup is hard to find. The fully remodeled home offers 4 bedrooms, 2 full baths, and approximately 2,800 square feet. The great room features cathedral ceilings, exposed beams, a fireplace, and walls of glass overlooking the property. The kitchen includes a cozy sitting area with a wood stove, while the dining area is framed by a large picture window. A first-floor bedroom with patio access and a full bath offer flexibility for guests, multigenerational living, a home office, or convenient one-level living. Upstairs, the primary suite includes a soaking tub beneath its own window. Outside, open meadow leads to wooded trails, with a private brook and dam creating a truly unique setting. There's room for horses, hobby farming, gardens, or simply enjoying the privacy. Recent updates include a new roof, Buderus oil furnace, and fresh interior paint. Minutes from the Rhode Island line, this one-of-a-kind property offers privacy, land, and a workshop that's nearly impossible to replicate.

564 Hubbard Rd, Killingly

$549,000

4 Beds ⋅ 3 Baths ⋅ 24187009 MLS

New price with recent improvements! Nestled at the end of a long, winding driveway, this exquisite Colonial home offers timeless New England elegance on over three private, picturesque acres. Surrounded by classic stone walls, sprawling lawns, mature gardens, and inviting outdoor dining spaces, this exceptional property is a secluded retreat rich in historic details and charm. Inside, you'll find four spacious bedrooms with one on the main floor, two and one-half baths, wide-plank hardwood floors, and five fireplaces that create warmth and character in nearly every room. One-of-a-kind hand-painted wall murals and custom artisan details enhance this home's distinctive personality while honoring its antique Colonial aesthetic. Built in 1988 and expanded in 1995 it includes a full basement, abundant storage and modern systems. Every space reflects craftsmanship rarely found in today's market. Located in the historic town of Ashford in Northeast Connecticut's "Quiet Corner" this remarkable property offers the perfect balance of peaceful country living with convenient access to nearby amenities as well as the Connecticut shoreline, Massachusetts, and the beautiful Rhode Island beaches. A truly exceptional offering for those seeking privacy, authenticity, and refined New England living. New roof and new septic system have been installed in last few months. Roof was installed days ago with transferrable 30-year warranty. Entire septic system was replaced months ago.

272 Horse Hill Rd, Ashford

$549,900

4 Beds ⋅ 3 Baths ⋅ 24186226 MLS

Live in this lovely house. 4-5 bedrooms 2.5 bathrooms. Eat-in kitchen, formal living room and formal dining room, first floor office, family room and laundry room. Most rooms have tin ceilings. The second floor is 4 bedrooms and 2 full bathrooms. Have your business in the former church...3300 sq ft with a balcony and a half bathroom. Handicap accessible. You could have your business on the first floor of the house and live on the second floor or you have an amazing 2 story barn....lots of options. All of this is on 1.58 acres. Subject to the recording of the new map, deed and easements.

350 Hartford Pike, Killingly

$1,275,000

4 Beds ⋅ 4 Baths ⋅ 24185273 MLS

Waterfront living at its most private and picturesque on beautiful Chamberlain Lake. Set on 200 feet of private lake frontage, this exceptional custom post-and-beam Cape offers a rare combination of craftsmanship, character, privacy and direct access to the water. Thoughtfully designed and built using timber milled from trees harvested on the property, the home has an unmistakable warmth and authenticity. A dramatic center brick chimney anchors the main living spaces, complemented by wide-board pine floors, exposed beams and abundant windows framing the surrounding landscape and lake. The spacious primary suite features a private balcony overlooking the water, two walk-in closets and a spa-like bath. Generously sized rooms and oversized step-in closets provide exceptional comfort and storage throughout. Step outside and enjoy the best of lake living with a private pathway leading to the water, ideal for swimming, fishing, kayaking and canoeing. Relax on the covered porch, gather around the fire pits, or enjoy the outdoor shower after a day on the lake. Beautifully landscaped grounds create a peaceful and private setting surrounded by mature trees and natural beauty.

95 Pole Bridge Rd, Woodstock

$875,000

4 Beds ⋅ 5 Baths ⋅ 24180671 MLS

NO TRICKS, ALL TREATS here. As the kiddos walk safely at the end of a town road cul-de-sac, up the paved driveway to the pretty front door, peek inside to see the details of this custom built ranch. Arched door ways, soaring ceilings, beautiful windows, and diverse gathering areas. Plenty of space on the more than 3000sqft main level living. What cannot be seen from the front door is the screened porch, covered deck, and pretty pergola with field stone patio. If you need more space, there is in-law style space finished above the garage. The majority of the lower level, walk out with sliders and its own garage, is finished with a media room, full bath, rec area and wet bar. In total, this property offers over 5000sqft of finished space, 3 garages, 2.12 acres, and situated conveniently in South Woodstock.

48 Grey Fox Lndg, Woodstock

$1,995,000

4 Beds ⋅ 4 Baths ⋅ 24180508 MLS

Extraordinary Waterfront Estate. Set on an exceptional 5.5-acre private lot with 265 feet of shoreline frontage, this completely rebuilt luxury residence offers a rare opportunity to own one of Woodstock's premier lakefront properties. Arrive via a long, newly paved private driveway that winds through a tranquil setting before revealing this stunning waterfront retreat. Offering 3,971 square feet, 4 bedrooms, and 4 bathrooms, the home was rebuilt from the ground up with next level quality and craftsmanship. Designed for both elegant entertaining and everyday enjoyment, the layout includes a formal dining room, spacious family room, custom mudroom, and a beautiful living room with propane fireplace overlooking Quasset Lake. The showpiece kitchen is truly one-of-a-kind, featuring handcrafted cabinetry by a New York artisan cabinet maker, thick quartzite countertops, premium built-in appliances, and a dramatic tray ceiling with custom white oak detailing. Luxury finishes continue throughout with veneer plaster walls, custom white oak vanities, a professionally designed primary closet, handmade laundry room cabinetry, and architectural flangeless LED lighting seamlessly integrated into the wood ceilings. Built with 2x6 construction, engineered floor systems, 2x12 roof rafters, red cedar siding and trim, central air, all-new heating and cooling systems, underground 400-amp service, and an automatic whole-house generator. Step outside and embrace the ultimate lake lifestyle.

158 W Quasset Rd, Woodstock

$2,950,000

4 Beds ⋅ 5 Baths ⋅ 24115278 MLS

A rare and refined country estate offering privacy, luxury, and elegance on over 53 acres in scenic Pomfret. This extraordinary 4,442 sq ft custom, Tennessee fieldstone home includes 4 bedrooms and 5 baths-including a private in-law apartment/second primary suite with its own entrance. An additional 16+ acre building lot provides development potential. Surrounded by forest and adjacent to 175 acres of open space, this home sits high with long eastern views into RI! A 1,000 ft paved driveway leads past over 500 ft of hand-laid stone walls to the stunning residence, framed by 10" cedar columns and solid mahogany double doors. The interior exudes craftsmanship with 8' solid wood doors, mahogany floors, 12" triple crown molding, and Marvin windows throughout. The grand great room boasts 20' ceilings and a massive fieldstone fireplace, while the private office stuns with a redwood ceiling, fireplace, and custom cherry built-ins. The chef's kitchen features Viking and Meile appliances, granite counters, cherry details, and opens to a sunny morning room and expansive veranda. The primary suite is a retreat with vaulted ceilings, a luxurious spa bath, radiant heated travertine floors, custom vanities, arched alcoves, and dual walk-ins. Additional highlights include a 3-car garage with Spanish cedar doors, Sonos sound system, generator, 139-head irrigation system, and walk-up basement ready to finish. This is a one-of-a-kind legacy property -stately, expansive, and exquisitely built.

282 & 260 Searles Rd, Pomfret

$1,299,000

4 Beds ⋅ 6 Baths ⋅ 24177811 MLS

Set on 10.3 private acres in desirable Woodstock Valley, Blue Heron Glade offers exceptional privacy, natural beauty and remarkable versatility. A long private drive crosses a cobblestone bridge and opens to a peaceful setting surrounded by stone walls, mature landscaping, abundant wildlife and a large private pond regularly visited by blue herons. More than 6,000 SF of finished living space is thoughtfully arranged into distinct areas for gathering, working, entertaining and retreating, allowing the home to adapt to many different lifestyles. The attached guest/in-law suite lives almost like a home of its own, with a bedroom, full bath, kitchen, loft/office and new white oak flooring. The finished lower level adds a custom speakeasy-style bar, theater and additional flexible rooms. Outdoors, enjoy a fenced inground pool and substantial pool house with granite counters, half bath and outdoor shower. Four oversized garage bays, unfinished loft space and high-speed fiber internet add even more versatility to this remarkable property.

1374 Rte 171, Woodstock

$799,900

4 Beds ⋅ 3 Baths ⋅ 24165439 MLS

TO BE CONSTRUCTED | Starting at $799,900 Welcome to Eastwood Estates, where luxury living meets the natural beauty and tranquility of Woodstock. Set on a picturesque 1.92-acre homesite bordering protected open space and framed by classic New England stone walls, this offering provides a rare opportunity to build a custom home in one of the area's most desirable neighborhoods. Partner with an experienced local builder to create a home that reflects your lifestyle and vision. Choose from thoughtfully designed plans, including a stunning Country Colonial featuring 4 bedrooms and 2.5 baths, or explore alternative layouts, or bring your own ideas to life within the builder's program. Each home is crafted with attention to detail, blending timeless elegance with modern functionality; open living spaces, quality finishes, and design flexibility suited for today's living. Eastwood Estates is governed by covenants that preserve the integrity and value of the neighborhood, including a minimum home size of 2,900 square feet (which may include finished lower-level space). Enjoy the peaceful charm of Woodstock with nearby access to local farms, walking trails, and scenic roads, while still being within reach of everyday conveniences and commuting routes. A unique opportunity to build a home that is both refined and personal, guided every step of the way.

36 Olde Meadow Rd, Woodstock

$674,900

4 Beds ⋅ 4 Baths ⋅ 24150988 MLS ⋅ Grandview Estates BLDG.

Development Opportunity! Fully approved condominium project on a private lot with views, offering a turnkey development package including land, two existing townhouses with garages, and approvals for eight additional units to be built, with fully engineered plans available by request. Town approvals are in place, underground utilities are on site, and initial infrastructure has been completed. Public water and sewer available, condominium documents recorded, and unit building plans are available. Existing units provide immediate value while allowing future expansion of the remaining approved units - ideal for developers seeking income with significant upside. This is an opportunity to own or develop a planned community in the northeast corner of Connecticut, with convenient proximity to both Rhode Island and Massachusetts.

115 Groveland Ave Unit 7 & 8, Putnam

$529,900

4 Beds ⋅ 3 Baths ⋅ 24130625 MLS ⋅ The Preserve At Valley View BLDG.

BEAUTIFUL CUSTOM BUILT CONDOMINIUMS IN A SCENIC AREA OF DAYVILLE! CLOSE TO 395, RHODE ISLAND AND MASSACHUSETTS BORDERS!! TUCKED INTO A BEAUTIFULLY LANDSCAPED AREA OFF OF VALLEY RD IN DAYVILLE. WORK CLOSELY WITH BUILDER AND PICK OUT ALL OF YOUR CABINETS, COUNTERTOPS, FLOORING ETC. TO MAKE IT TRULY YOURS! THESE HIGH END CONDOMINIUMS HAVE BEEN GOING FAST! FIRST PHASE IS NEARLY COMPLETE WITH ALL UNITS SOLD OR CURRENTLY UNDER CONTRACT! EACH UNIT BOASTS 4 BEDROOMS, 3 BATHS AND AN EXTRA FLEX ROOM TO MAKE INTO WHATEVER YOUR IMAGINATION DREAMS OF. HOA IS A LOW $190.00 A MONTH WHICH INCLUDES TRASH REMOVAL, SNOW REMOVAL, GROUNDS MAINTENANCE AND PROPERTY MANAGER. COME SEE WHAT "THE PRESERVE AT VALLEY VIEW" HAS TO OFFER! WE WOULD LOVE TO MEET YOU! Photos are of our model. Design your own floor plan and interior choices. Work closely with the builder.

16 Valley View Dr, Killingly

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