Windham County, CT Homes between $700,000 and $800,000 for Sale

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Newest Windham County, CT Homes between $700,000 and $800,000 for Sale

$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

$769,000

3 Beds ⋅ 3 Baths ⋅ 73586961 MLS

A truly extraordinary property, 332 Ravenelle Road offers space, quality, privacy and versatility that are nearly impossible to find! Set on 13.5 gorgeous acres, this expansive ranch was built and occupied by its contractor/builder with exceptional attention to quality throughout. Designed for easy one-floor living, the home features 9-foot ceilings and a spectacular open floor plan anchored by a chef's kitchen and enormous family room-perfect for everyday living and entertaining. The massive 3-car garage boasts impressive 13-foot ceilings, while the 9-foot-ceiling basement runs virtually the full footprint of the home and previously housed the builder's extensive workshop-ideal for a contractor, car enthusiast, hobbyist or home-based business. Outside is your own private retreat with an above-ground pool, fenced area for animals, shed, abundant wildlife and beautiful seasonal views. Approximately 100 acres of landlocked private property and hundreds of acres of conservation land beyond create remarkable surrounding privacy and make this setting especially appealing to hunters and outdoor enthusiasts. Just across the street, West Thompson Lake offers fishing, boating and a public boat launch. A rare combination of exceptional craftsmanship, one-floor living, serious workspace and an incredible country lifestyle!

332 Ravenelle Road, Thompson

$799,000

5 Beds ⋅ 4 Baths ⋅ 24211775 MLS

Set on 19 picturesque acres in Thompson, this unique property offers tremendous flexibility for residential and equestrian use. Formerly used as a two-family home it provides options for single family, multi-generational living, farm staff, owner occupancy, or rental income. The home has been professionally cleaned, with major improvements already completed including a new roof, windows, garage doors, repointed chimney, serviced furnace, new dishwasher in the upper unit, refinished upstairs floors, repainted porch, and rebuilt deck. Kitchens and bathrooms offer an opportunity for additional cosmetic updating and personalization. Equestrian amenities are extensive, including a 12-stall main barn with multiple tack, feed and storage areas, lounge, bathrooms, water, and an approximately 2,000-bale hay loft. The lower barn offers 7 additional stalls with room to expand, plus storage. Two accessory buildings include a garage-style structure ideal for equipment storage. A 50' x 100' indoor arena provides year-round riding, while five fenced grass pastures with automatic waterers offer excellent turnout. With substantial infrastructure, multiple buildings, established fencing, and 19 acres - this property is ready for its next chapter. A rare opportunity for an equestrian estate, boarding or training operation, or simply the space to create your ideal multi-generational property.

91 Church St, Thompson

$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

$779,000

5 Beds ⋅ 4 Baths ⋅ 24209434 MLS

Set high on historic Woodstock Hill, this distinctive 19th-century property offers a rare combination of history, character, exceptional views, flexible living spaces, guest accommodations, gardens, and opportunity. Offering approximately 2,500 square feet, this beautifully maintained home features five bedrooms and three-and-a-half baths, along with multiple living areas and a beautiful sitting porch overlooking the surrounding landscape. The home has been thoughtfully adapted to accommodate both private living and hospitality, creating flexibility for a variety of lifestyles. Two separate, thoughtfully furnished guest suites provide an established short-term rental opportunity and have enjoyed strong bookings. Guests have included parents visiting their children attending Woodstock Academy and Pomfret School, families attending weddings and local events, and visitors seeking to experience the beauty and charm of Woodstock. The grounds offer another exceptional dimension. Flower-growing areas, gardens, and a flower stand have been developed by the current owners during their first year on the property, building upon their longstanding experience with gardening and growing. The property offers an exciting opportunity to continue and expand the flower-growing vision, create a garden-based business, or explore the possibility of a future studio or shop, subject to applicable approvals.

500 Rte 169, Woodstock

$769,900

3 Beds ⋅ 3 Baths ⋅ 24204987 MLS

332 Ravenelle Rd, Thompson

$749,900

5 Beds ⋅ 3 Baths ⋅ 24202466 MLS

Set on nearly 25 private acres in Pomfret, this well maintained and upgraded 3,343 sq ft home offers space, privacy and incredible recreational potential. Features include a 3-car attached garage with an attached workspace, primary suite w/private balcony & jetted tub, central air, ducted heat, a whole-house generator and a heated/cooled basement offering an easy path to additional finished space and extra bedroom potential. Inside, enjoy a beautiful stone fireplace with wood-stove insert, while a screened porch off the dining room overlooks a wooded setting. Extensive covered deck space provides even more outdoor living, including the current hot tub, which is included. A detached, fully insulated and heated garage/workshop with a full 16' door provides exceptional space for vehicles, equipment, hobbies or storage. Established riding and walking trails wind throughout the acreage. The property also features a former in-ground pool with potential for restoration and a former ice rink/tennis/pickleball court ready to be brought back to life. An ideal setting for a private retreat or a horse farm, with abundant space for recreation, equipment, toys and outdoor living. Ideal for anyone seeking a serious workshop, trail riding, outdoor entertaining and room to spread out. A rare combination of acreage, recreation, storage, privacy and flexible space. Conveniently located under 30 miles from Providence, 34 miles from Foxwoods and Mohegan Sun with easy access to I-395.

40 Searles Rd, Pomfret

$799,000

5 Beds ⋅ 4 Baths ⋅ 24203344 MLS

EXCEPTIONAL EQUESTRIAN PROPERTY WITH 19 ACRES & TWO-FAMILY HOME! Set on 19 picturesque acres in Thompson, this unique property offers tremendous flexibility for residential and equestrian use. The two-family home provides options for multi-generational living, farm staff, owner occupancy, or rental income. The home has been professionally cleaned, with major improvements already completed including a new roof, windows, garage doors, repointed chimney, serviced furnace, new dishwasher in the upper unit, refinished upstairs floors, repainted porch, and rebuilt deck. Kitchens and bathrooms offer an opportunity for additional cosmetic updating and personalization. Equestrian amenities are extensive, including a 12-stall main barn with multiple tack, feed and storage areas, lounge, bathrooms, water, and an approximately 2,000-bale hay loft. The lower barn offers 7 additional stalls with room to expand, plus storage. Two accessory buildings include a garage-style structure ideal for equipment storage. A 50' x 100' indoor arena provides year-round riding, while five fenced grass pastures with automatic waterers offer excellent turnout. With substantial infrastructure, multiple buildings, established fencing, and 19 acres - this property is ready for its next chapter. A rare opportunity for an equestrian estate, boarding or training operation, or simply the space to create your ideal multi-generational property.

91 Church St, Thompson

$799,000

24203317 MLS

This is a thriving equestrian facility offering several barns, indoor riding arena, tractor/equipment barns on 19.1 acres with a multi family home.

91 Church St, Thompson

$749,900

7 Beds ⋅ 4 Baths ⋅ 24198629 MLS

Step back in time while enjoying the comforts of today in this exceptional Antique Colonial, built in 1830 and proudly situated on historic Thompson Hill. From the moment you arrive, the home makes a lasting impression with its welcoming wrap-around front porch, tastefully landscaped grounds, and classic circular driveway. The property also features a sizeable barn, offering abundant storage and endless possibilities. There is even an original "privy"! Inside, the 5-bedroom main residence offers generous closet space, 2 full baths, a thoughtfully designed updated kitchen, both formal and informal dining spaces, and beautifully updated bathrooms.A convenient first-floor laundry adds to the functionality of this spacious home, while the property's original character provides the warmth and charm that only an antique Colonial can offer. A standout feature is the spacious two-story in-law apartment, complete with a private entrance and rear deck. With 2 bedrooms and 1 1/2 baths, this versatile space is perfect for extended family, guests, a home office, or other living arrangements. The property has been thoughtfully improved with updated mechanical systems and a brand-new septic system, providing modern peace of mind while maintaining the home's historic character. This home is ideally located just minutes from the Massachusetts and Rhode Island state lines and major commuter routes allowing quick and easy access to the Arts, Dining, Shopping, Medical facilities and Airports

362 Thompson Rd, Thompson

$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

$749,900

3 Baths ⋅ 24196199 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

$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

$789,900

3 Beds ⋅ 2 Baths ⋅ 24156839 MLS

80 Aldrich Rd, Putnam

$750,000

1 Baths ⋅ 24143048 MLS

Own a local landmark, a freestanding 2,324 SF restaurant/bar and 600 SF storage building in Thompson, CT, zoned for commercial use. Newly renovated in 2024, this fully occupied property is under a NNN lease, making it an excellent investment opportunity. Situated at the crossroads of MA and RI, and just minutes from Thompson Speedway, the location has easy access from Exit 50 off Route 395. The property features 30 parking spaces and is nestled in a charming New England village atmosphere, adding to its appeal for both local patrons and visitors. Don't miss out on this prime commercial opportunity!

142 Old Turnpike Rd, Thompson

$750,000

24074507 MLS

41 lot approved sub-division (detached single family units). Town water & sewer reserved for project. Close to I-395 and Route 12. Total of 19.37 acres. For Sale $750,000. DIRECTIONS: I-395 S Exit 43. Turn left on Attawaugan Crossing Rd. Go straight on Ballouville Rd. Just past Church St. on left. I-395 N Exit 43. Turn right on Attawaugan Crossing Rd. Go straight on Ballouville Rd. Just past Church St. on left.

38-82 Ballouville Rd, Killingly

$799,500

24102801 MLS

* City Water, Septic, and Gas * Located across the street from Walmart Supercenter * Traffic Count: 14,900 * Conceptual Plans for Various Uses * Zoning Uses: Retail, Self Storage/Contractor Bays, Apartments/Condos * Zone: PC * Nearby Tenants: McDonald's, CVS, NAPA, Advance Auto Parts, Dollar Tree, Ocean State Job Lot, Dunkin', KFC, AutoZone, & (coming soon) Tractor Supply

405 Providence Rd, Brooklyn

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Windham County, CT Homes between $700,000 and $800,000 for Sale

Newest Windham County, CT Homes between $700,000 and $800,000 for Sale

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