Windham County, CT Real Estate Search

Windham County, CT Single Family Homes for Sale

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Newest Windham County, CT Single Family Homes for Sale

158 W Quasset Rd, 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
13 Bates Rd, Chaplin
$399,900
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
282 & 260 Searles Rd, Pomfret
$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
1374 Rte 171, Woodstock
$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
433 Wrights Crossing Rd, Pomfret
$6,450,000
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
37 Ruth St, Killingly
$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
408 Huntington Rd, Scotland
$350,000
3 Beds ⋅ 2 Baths ⋅ 24172634 MLS
Charming home located at 408 Huntington Rd in Scotland, CT. Set on a spacious lot, this property offers a peaceful country setting with plenty of outdoor space. Inside, you'll find a functional layout with comfortable living areas, a bright kitchen, and well-sized bedrooms. All the wood floors were finished. Apartment on the second floor. A great opportunity for anyone looking for quiet living while still being conveniently located. Don't miss your chance to see this property!

408 Huntington Rd, Scotland
28 Circle Dr, Windham
$160,000
3 Beds ⋅ 2 Baths ⋅ 24171622 MLS
Completely remodeled 3-bedroom, 2-bath mobile home in North Windham! This move-in-ready home has been thoughtfully updated throughout and features a brand-new roof, new appliances, and modern finishes from top to bottom. The interior offers a bright and functional layout with updated flooring, refreshed kitchen and bathrooms, and comfortable living space. With recent upgrades throughout, this home provides a great opportunity for affordable, low-maintenance living. Conveniently located close to shopping, restaurants, and local amenities.

28 Circle Dr, Windham
592 Ference Rd, Ashford
$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
10 Indian Run Dr, Thompson
$415,000
1 Beds ⋅ 1 Baths ⋅ 24168088 MLS
Brand new construction offering easy, modern living! This thoughtfully designed home features 1 bedroom and 1 full bathroom 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 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
106 Church St, Brooklyn
$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
36 Olde Meadow Rd, 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
80 Aldrich Rd, Putnam
$789,900
3 Beds ⋅ 2 Baths ⋅ 24156839 MLS
*Pictures are similar to built* Discover the convenience of one-level living in this beautifully crafted new to-be-built construction ranch offering 2,032 square feet of thoughtfully designed space. Featuring 3 bedrooms and 2 full baths, this home blends comfort and style with an open-concept kitchen, dining, and living area - perfect for entertaining or everyday living. A stunning four-season room invites you to relax year-round while taking in the peaceful surroundings. The spacious primary suite offers a private retreat with a full en-suite bath and a generous walk-in closet. Convenient main-level laundry adds to the ease of single-floor living. The fully walk-out basement offers the option to finish an additional 960 square feet, creating incredible potential for an in-law setup, guest suite, home office, or recreation space. Set on 2.48 private acres in a quiet corner of Putnam, CT, this property provides the serenity you've been searching for while remaining close to local amenities. A rare opportunity to own brand-new construction with room to grow!

80 Aldrich Rd, Putnam
47 Texas Heights Rd, Plainfield
$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
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