Windham County, CT Single Family Homes for Sale

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Newest Windham County, CT Single Family Homes for Sale

$799,900

4 Beds ⋅ 3 Baths ⋅ 73530654 MLS

36 Olde Meadow Road, Woodstock

$880,000

4 Beds ⋅ 5 Baths ⋅ 24180671 MLS

Welcome to this exceptional custom-built ranch, perfectly situated at the end of a peaceful cul-de-sac in South Woodstock. Offering a great blend of luxury, comfort, and versatility, this impressive home boasts 2,822 square feet of beautifully designed main-level living space, with over 5000 square feet of total finished living area including the private in-law apartment above the garage and the spacious walk-out lower level. Stepping through the front door, be captivated by soaring ceilings, arched doorways, and quality craftsmanship throughout. Generously sized living areas provide the perfect setting for entertaining family and friends, while thoughtfully designed spaces offer comfort and privacy for everyday living. The home features spacious bedrooms, abundant storage, and countless custom details that reflect pride of ownership and meticulous attention to quality. Come see this property to see all that it offers.

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

$419,900

5 Beds ⋅ 3 Baths ⋅ 24179982 MLS

Spacious farmhouse living at its best! This charming 5-bedroom, 2 full bath, and 1 half bath home sits on an expansive 11 acres, offering endless possibilities for privacy, recreation, or hobby farming. Inside, you'll find hardwood flooring throughout and two cozy fireplaces that add warmth and character. The versatile layout includes two additional family rooms that could easily serve as extra bedrooms, a home office, playroom, gym, or guest space - perfect for today's flexible lifestyle needs. Tucked away in a truly special setting, this home is surrounded by federal land, offering direct access to scenic hiking and horseback riding trails just steps from your door. Enjoy the peace and privacy of nature while still having the convenience of recent updates, including a newer boiler and porch. A seldom-available gem with room to grow both inside and out! Enjoy the space, charm, and opportunity this beautiful property provides with peaceful surroundings while still being in close proximity to Mansfield Hollow State Park, as well as nearby shopping and dining options. A rare opportunity to own acreage, space, and convenience all in one - schedule your showing today!

13 Bates Rd, Chaplin

$500,000

3 Beds ⋅ 2 Baths ⋅ 24178930 MLS

Custom passive solar Contemporary set on 5+ private acres surrounded by natural beauty and peaceful scenery. A 5-year-young sunroom with tile flooring offers flexible space for relaxing, gardening, or enjoying year-round views of the landscape. Step outside to the spacious deck, ideal for outdoor dining or quiet mornings overlooking the tranquil setting. The inviting living room features a newer pellet stove and tile flooring designed for comfort and easy maintenance. Country dining room with wide plank floors, exposed reclaimed wood beams, and newer Andersen slider leading to the deck. Bright kitchen includes 3 skylights, porcelain farmhouse sink, solid wood cabinetry, stainless steel appliances, tile floor, and walk-in pantry. Convenient laundry/mudroom connects the kitchen to the attached 2-car garage. First Floor Primary Bed with new carpet, ceiling fan, slider to the deck to listen to the cute garden pond with water fountain. The second floor offers 2 additional bedrooms with exposed wood beams, a partially finished recreation room, and full bath with shower stall. The upper level sunroom includes a propane stove for supplemental heat. Energy-efficient design with strong insulation and berm construction helps maintain comfortable temperatures year-round. Additional updates include newer roof, water heater, washer and dryer, and new well water line. Convenient location close to shopping, dining, and commuter routes. Approx. 25 minutes to UCONN and 40 minutes to Hartford.

30 Grant Hill Rd, Brooklyn

$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

$1,395,000

4 Beds ⋅ 6 Baths ⋅ 24177811 MLS

Set on 10.3 private acres in desirable Woodstock Valley, "Blue Heron Glade" offers a rare blend of privacy, natural beauty, and thoughtfully designed living spaces in Connecticut's Quiet Corner. A long private driveway with a charming cobblestone bridge leads to this exceptional property surrounded by stone walls, abundant wildlife, and a large pond frequented by blue herons. The main residence offers over 6,000SF above grade plus an extensively finished lower level designed for entertaining and everyday comfort. The kitchen features granite countertops, a large center island, and abundant cabinetry. The first-floor primary suite includes tray ceilings, a spa-like bath with double sinks, a 2-person jetted tub, and separate shower. The finished lower level offers a completely unique atmosphere with a custom speakeasy-style bar, theater room, full bath, dog washing station, laundry area, and private office suite with 2 rooms and an additional full bath. An attached in-law apartment has its own bedroom, full bath, kitchen & loft/office area, and newly added white oak flooring. 4 oversized garage bays, 2 of which offer unfinished loft space above. Outside, enjoy the fenced inground pool area with beautifully updated landscaping & a pool house complete with plumbing, granite counters, half bath, & outdoor shower. Fiber internet with mesh nodes provides seamless connectivity throughout the house. A rare Woodstock Valley retreat where privacy, nature, and luxury come together.

1374 Rte 171, Woodstock

$549,900

4 Beds ⋅ 3 Baths ⋅ 24176497 MLS

This stunning 2005-built Colonial offer sophisticated living space, highlighted by gleaming hardwood floors that flow throughout the entire home. The heart of the house is an expansive kitchen featuring premium granite countertops, stainless steel appliances, and a gas stove, opening perfectly to a living area anchored by a cozy gas fireplace. Recent new renovated master bathroom never been use. Designed for modern comfort, the home includes four impressively large bedrooms and the added luxury of central air and a fully finished lower level, ideal for a home media room, gym, or office. Situated on a private, oversized lot, this property combines high-end finishes with the space.

15 Salmon Dr, Brooklyn

$6,950,000

12 Beds ⋅ 9 Baths ⋅ 24101484 MLS

Welcome to Bark Meadow Farm, a 127-acre legacy estate once cherished by the Gulden mustard family in CT's "Quiet Corner." The journey begins at a majestic entrance, where a striking allee of century-old maples stands alongside magnificent oaks nearing 200 years of age. This multi-generational compound offers 12 bedrooms & 7.2 bathrooms across three year-round residences. At the heart is the 1799 Main Residence, a 7,577 SF, 5-bedroom, 5.2-bathroom masterpiece of timeless architecture. Ideal for grand-scale entertaining, the butler's pantry flows seamlessly from the exquisite dining room into a spacious eat-in kitchen, complete with a Viking Professional stove. Additional structures include a 1900 Caretaker's Residence (4 bedrooms) & a 1948 14-stall barn with a 3-bedroom apartment above-ideal for a barn manager or rental income, it also offers great potential for a remote home office. Car collector enthusiasts & woodworking hobbyists will love the ultra-spacious garage, complete with a large workshop, a walk-in laundry/tack room, & a powder room. Amenities abound: 2 inground pools, an enchanting pool house with a potting room, raised-bed gardens, & a tranquil bass pond. Enjoy direct access to the Air Line Trail for riding/hiking. The estate directly abuts the CT Audubon Society land, with its beautiful trails located just a half-mile down the road, while the prestigious Pomfret & Rectory Schools are a mere 1.5 miles away. Conveniently accessible to Hartford, Providence/RI

433 Wrights Crossing Rd, Pomfret

$285,000

3 Beds ⋅ 1 Baths ⋅ 24174794 MLS

Discover the potential in this fixer-upper featuring an ideal floor plan with spacious, flowing living areas and endless possibilities to make it your own. The open and functional layout offers great bones for a renovation project, with generously sized rooms, abundant natural light, and a seamless flow perfect for modern living and entertaining. Whether you're an investor, flipper, or buyer looking to create your dream home, this property is a fantastic opportunity to bring your vision to life while adding significant value. A rare chance to transform a home with incredible potential into something truly special! Property is subject to short sale.

37 Ruth St, Killingly

$749,900

3 Beds ⋅ 4 Baths ⋅ 24173131 MLS

Welcome to this exceptional, custom built brick home, set on a stunning piece of property where quality, craftsmanship, and timeless design come together beautifully. From the moment you step inside, you will appreciate the vaulted ceilings, open layout, and impressive mix of hardwood, marble and tile flooring. The heart of the home features a beautifully designed kitchen with quartz countertops, custom built cupboards, 2 ovens, trash compactor and more! The dining room features a wood-burning fireplace that's never been used! With enough room for the largest table. Off the kitchen, enjoy a heated sunroom that offers peaceful views overlooking the inground pool and hot tub, create a perfect space to relax year-round. The main level offers a spacious primary suite with a separate sitting room, custom walk in closet. The en suite features a soaking tub and walk in shower with a heated lamp, double sink vanity and marble countertops. An office on the main floor provides flexibility for working from home or additional living space. Convenient first floor laundry with a half bath adds every day practicality. Upstairs you'll find two additional bedrooms and a full bathroom. The heated basement has an additional half bathroom and offers endless possibilities for recreation, wood shop, storage, gym, or finished space. Additional features include a four car garage, central air, Buderus, furnace, water softener, 200 amp, electrical service, and security system. This is a rare opportuni

524 Wauregan Rd, Brooklyn

$194,500

3 Beds ⋅ 2 Baths ⋅ 24172614 MLS

Check out this antique Cape just minutes from downtown Danielson! This home has 3 bedrooms located on the upper floor, with plenty of flexible space. The primary floor has many wonderful features including a large kitchen that opens up to the back deck, a full bath, and a dining space. Enjoy overlooking the yard from the enclosed deck! Plumbing did not hold positive air pressure at the time of winterization. This property may qualify for Seller Financing (Vendee). If property was built prior to 1978, Lead Based Paint Potentially Exists. Highest & Best Hold Period active - expires 09/15/2026 01:00 PM CST. All submissions must be in before deadline, no exceptions.

85 Wauregan Rd, Killingly

$649,900

3 Beds ⋅ 3 Baths ⋅ 24163257 MLS

Rare opportunity to own a waterfront ranch with a legal in-law apartment set on over 3 private acres in the peaceful countryside of Ashford. Boasting over 800 feet of direct frontage on a state-owned pond with no other homes on the water, this property offers natural beauty, and a truly one-of-a-kind setting. The main home features a comfortable single-level layout filled with natural light, including a spacious living room with fireplace, an inviting dining area, and a functional kitchen ideal for everyday living and entertaining. Generous bedrooms and well-appointed baths complete the main level. The fully approved in-law apartment provides its own private entrance, kitchen, living area, bedroom, and bath-perfect for multi-generational living, guests, or potential rental income. A partially finished lower level adds valuable flex space for a home office, gym, or recreation room, along with additional storage. Step outside to enjoy serene water views, abundant wildlife, and the peace of having your own private stretch of shoreline-ideal for kayaking, fishing, or simply relaxing in nature. Conveniently located with easy access to Interstate 84 and just a short drive to University of Connecticut, this property combines seclusion with accessibility. A truly unique waterfront retreat offering privacy, versatility, and endless potential.

592 Ference Rd, Ashford

$859,900

3 Beds ⋅ 3 Baths ⋅ 24169232 MLS

Rare opportunity to own 100 feet of beautiful pond frontage in Thompson, CT! From the moment you arrive, you'll fall in love with the peaceful setting, breathtaking water views, and the care that has gone into maintaining this home. Whether you're enjoying your morning coffee overlooking the lake, relaxing in the hot tub, or unwinding after a long day, this property offers a true sense of comfort, relaxation, and escape. This well-maintained 3-bedroom, 2.5-bath home offers approximately 1,437 sq ft of inviting living space and was thoughtfully designed with energy efficiency in mind, featuring both geothermal heating and solar. The home feels warm and welcoming throughout, filled with natural light and plenty of space to make it your own. The partially finished basement offers added flexibility-perfect for a home office, gym, playroom, or additional living space. Outside, the 0.82-acre lot provides plenty of room to entertain, enjoy the outdoors, and take in the natural beauty surrounding you. One of the standout features of this property is the detached 2-car garage with a spacious loft area and half bath, offering endless potential for a studio, workshop, guest space, home office, game room, or whatever fits your lifestyle best. Whether you're searching for a year-round home or a peaceful waterfront retreat, this property offers the perfect blend of comfort, efficiency, and scenic lakeside living-all tucked away in a quiet Thompson location. HOT TUB is STAYING!

9 Becola Rd, Thompson

$480,000

2 Beds ⋅ 2 Baths ⋅ 24168088 MLS

Brand new construction offering easy, modern living! This thoughtfully designed home features 2 bedrooms and 2 full bathrooms with a bright, open floor plan perfect for today's lifestyle. The spacious kitchen showcases a center island, ideal for entertaining, and flows seamlessly into the living and dining areas. Enjoy an abundance of natural light from the many windows throughout. The primary suite offers comfort and privacy, while additional features include central air conditioning and a 2-car garage. Step outside to a deck overlooking a partial lake view. A wonderful opportunity to own a low-maintenance, newly built home in a scenic setting!

10 Indian Run Dr, Thompson

$400,000

1 Beds ⋅ 1 Baths ⋅ 24168085 MLS

6 Indian Run Dr, Thompson

$744,999

3 Beds ⋅ 3 Baths ⋅ 24167102 MLS

Approved building lot on desirable street, property is on a shared driveway. TO BE BUILT: A 2,020 sqft., 3 bedroom, 2.5 bath colonial style home sits on a beautiful 2.6 acre lot. The kitchen features a tile backsplash, oversized island, stainless steel range hood, pantry cabinet, and quartz countertops. The living room flows from the kitchen creating an open feel. Hardwood flooring throughout the home. The staircase is a wonderful centerpiece of the home, with banisters and iron balusters. Upstairs you will find 3 large bedrooms. The primary bedroom features a walk-in closet and attached bath with tile shower and double sink vanity. Forced hot air and A/C climate control the home. Attached 2 bay garage, back deck, walk out basement and front porch are just a few other wonderful features.

106 Church St, Brooklyn

$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

$219,000

4 Beds ⋅ 1 Baths ⋅ 24159602 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

$789,900

3 Beds ⋅ 2 Baths ⋅ 24156839 MLS

80 Aldrich Rd, Putnam

$689,000

2 Beds ⋅ 2 Baths ⋅ 24142329 MLS

Perched above the shoreline of private Witches Woods Lake, this beautifully renovated waterfront retreat pairs breathtaking water views with exceptional privacy and an incredible indoor-outdoor lifestyle. Nearly 800 square feet of brand-new multi-level TimberTech decking takes full advantage of the setting, creating an extraordinary space for entertaining, dining, relaxing, and enjoying the lake below. Thoughtfully and extensively improved, the home features a refreshed granite and stainless kitchen, whole-house mini-split heating and cooling, a new full septic system, Kohler automatic generator, updated baths, and numerous additional improvements throughout. The main level offers an easy flow between the kitchen and living room, two bedrooms, a full bath, and a sun-filled enclosed porch opening directly to the decks and panoramic lake views. The professionally waterproofed, finished walk-out lower level adds valuable flexibility with a spacious recreation room, full bath with laundry, and direct exterior access. A one-car garage, breezeway, and multiple storage areas add everyday convenience, and the home is offered furnished for an easy transition into lake life. Witches Woods Lake is treasured for its peaceful atmosphere and natural beauty, offering kayaking, swimming, fishing, sailing, and regulated power boating, while restrictions on jet skis and personal watercraft help preserve the quiet character of this special waterfront community.

60 Indian Spring Rd, Woodstock

$289,000

3 Beds ⋅ 1 Baths ⋅ 24133723 MLS

RANCH HOME! Bring your vision and make this 3-bedroom, 1-bath ranch your own! Situated on a corner lot, this 960 sq ft home offers great potential with a full basement for added space or storage. Enclosed porch. With some repairs and updates, this property could shine again-ideal for investors, DIY enthusiasts, or first-time buyers looking for a project. Features a dirt driveway and solid bones ready for your finishing touches.

47 Texas Heights Rd, Plainfield

$520,000

4 Beds ⋅ 3 Baths ⋅ 24125003 MLS

Step back in time with this one-of-a-kind 1830 Greek Revival farmhouse, offering 2,150 sq ft of character and charm on a picturesque 0.90-acre lot surrounded by farm land. Just down the hill from historic Woodstock Hill and the Academy, this setting is as scenic as it is convenient. Inside, wide plank floors and distinctive windows frame beautiful country views, while the front entry showcases its original door with full exterior shutters, a hallmark of Greek Revival style. The living room centers on a classic fireplace, and along the upstairs landing a wall of built-in bookshelves creates a welcoming library space. Three bedrooms are located on the second floor, with an additional first-floor room currently serving as a fourth bedroom. The primary includes a walk-in closet and bath with a clawfoot tub. The walk-up attic offers potential for an office, playroom, or studio. The kitchen features a custom layout paired with quality appliances (Sub-Zero fridge & Thor cooktop) and the warmth of a wood stove. Updates include new Trex decking and a newly finished three-season room off the dining room. Historic touches, such as unique wallcoverings and original details, remain intact, blending history, artistry, and the timeless charm of living in Woodstock, CT. Property to be sold in as-is condition.

101 Child Hill Rd, Woodstock

$439,000

4 Beds ⋅ 2 Baths ⋅ 24132242 MLS

Nestled in the peaceful, rural charm of Scotland, CT, this lovingly updated 9-room, 4-bedroom, 2-bathroom home delivers the perfect blend of comfort, character, and modern convenience. From the moment you arrive, you'll feel the embrace of home - and see endless opportunities for family life here. This home is ready for your life to unfold - from quiet weekday mornings to lively gatherings. Step inside to discover a brand-new kitchen designed with both functionality and elegance in mind-featuring modern cabinetry, sleek countertops, and stylish fixtures. Both full bathrooms have been fully renovated. Throughout the home, gleaming hardwood floors flow seamlessly from room to room, adding warmth and character to every space. Set on a serene property surrounded by the natural beauty of eastern Connecticut, this home offers the ideal mix of quiet country living and modern comfort-all within a short drive to nearby amenities, schools, and major routes. SOLD AS-IS.

7 Devotion Rd, Scotland

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Windham County, CT Single Family Homes for Sale

Newest Windham County, CT Single Family Homes for Sale

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