Windham County, CT Real Estate Search

Windham County, CT Homes between $500,000 and $600,000 for Sale

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Newest Windham County, CT Homes between $500,000 and $600,000 for Sale

$533,000
5 Beds 2 Baths 24203884 MLS
Beautifully restored 1880 Colonial farmhouse set on an impressive 18.03 acres, offering a wonderful opportunity for farming, homesteading, or simply enjoying the peace and beauty of the countryside. Approximately 10 acres are fenced and well suited for cows, goats, sheep, horses, or other agricultural uses. The property also features a greenhouse, multiple outbuildings, and a farm stand building along the road-perfect for selling farm-fresh goods. The home offers the charm and character you would expect from an 1880 farmhouse, combined with thoughtful updates. The spacious kitchen features an open floor plan, granite countertops, and an abundance of new cabinetry. A convenient mudroom off the side entrance includes a large closet and full bath. The kitchen flows naturally into the family room, where numerous windows fill the space with natural light. Enjoy the warmth of the wood stove and access to the back deck overlooking the beautiful property. The formal dining room and living room provide additional gathering spaces, with the living room featuring a pellet stove. Two additional rooms are currently being used as offices and laundry. The primary bedroom and two additional bedrooms showcase beautiful original wide-board flooring, adding to the home's timeless character. The land is truly special, bordering the scenic Mt. Hope River and offering open space, privacy, and endless possibilities. With its historic charm, extensive acreage, outbuildings, agricultural potential

813 Westford Rd, Ashford

$500,000
3 Beds 3 Baths 24204889 MLS
"Exceptional Raised Ranch with Custom Greenhouse, New Composite Deck, Solar & Flexible Finished Lower Level" Welcome to this thoughtfully enhanced 3-bedroom, 2.5-bath raised ranch set on 0.75 beautifully maintained acres in North Grosvenordale. Offering 2,628 square feet of living space, this home combines comfortable everyday living with exceptional spaces for entertaining, gardening, fitness, and relaxation. The spacious eat-in kitchen provides direct access to a custom-built greenhouse, making it easy to enjoy gardening throughout the seasons. Outside, established gardens and a brand-new composite deck create a wonderful setting for morning coffee, outdoor dining, or just relaxing. The main level features two professionally designed full bathrooms, including one with a walk-in shower and another with a luxurious soaking tub. The finished lower level provides impressive versatility, with 2 separate exterior entrances, pellet stove, half bath, laundry, and a state-of-the-art exercise space. The garage-under has been transformed into a dedicated home gym and could offer additional possibilities for recreation, hobbies, or potential in-law accommodation, subject to buyer verification and applicable requirements. Additional highlights include new water heater and solar panels. Originally built in 1965, this unique property has been designed to offer modern amenities while maintaining the character and functionality of a classic raised ranch.

1 Corttiss Rd, Thompson

$589,000
2 Beds 2 Baths 24201418 MLS
There's something special about being able to see the lake from home and be at the water in just a short walk. Welcome to 4 Oak Drive, a thoughtfully cared-for 2-bedroom, 2-full-bath home with a spacious loft in the Lake Bungee community. With deeded lake and beach rights and views of the water, this newer home sits on an inviting corner lot surrounded by colorful flowers, raised vegetable gardens and touches of classic New England charm. Traditional stone walls along the adjoining historic cemetery add to the peaceful character of the setting. Inside, the open-concept kitchen with granite countertops and center island flows comfortably into the dining and living areas, with windows bringing in plenty of natural light and views toward the lake. Step out onto the deck to unwind and enjoy the glowing sunsets that cast a warm light across the property. Both bedrooms are on the main level, including the primary with a large walk-in closet, private full bath and sliders to its own small deck. Upstairs, the open loft offers flexible additional space along with two closets and attic storage. The full walk-out basement with sliders provides plenty of storage and potential for future finished living space. Generator hookup ready for added peace of mind. Lovingly maintained and easy to settle into, this home offers a welcoming place to enjoy the seasons, the lake and the simple pleasures of home, all while being conveniently located near the Massachusetts line and area amenities.

4 Oak Dr, Woodstock

$585,000
3 Beds 2 Baths 24202735 MLS
Timeless New England character, generous living spaces, and exceptional versatility come together in this historic home. Set on approximately 1.2 acres, this distinctive 1850 Colonial offers nearly 2,400 square feet of living space along with a detached carriage house that adds another dimension of possibilities to this unique property. Step inside and discover the warmth and character of a classic Georgian colonial. Generously proportioned living and dining rooms provide an inviting backdrop for everyday living and entertaining, while hardwood flooring enhances the home's historic appeal. The kitchen is appointed with granite countertops and stainless steel appliances, creating a comfortable gathering space with a blend of traditional charm and modern convenience. A flexible room on the main level, paired with access to a full bath, offers options for an office, guest room, den, or potential first-floor bedroom. Upstairs, three well-sized bedrooms provide comfortable retreats, accompanied by a second full bath and conveniently located laundry. Updated roof, windows and central air are thoughtful enhancements One of the property's most distinctive features is the detached carriage house. Previously utilized as in-law or guest space and equipped with its own electric meter and heating system, this versatile building offers exciting potential. Additional workshop and loft storage. Outdoor patio and stunning front porch lends endless enjoyment. A true showpiece of a home!

1015 North Rd, Killingly

$549,900
3 Beds 3 Baths 24201270 MLS
There's something special about being the first to call a brand-new home your own! Set within a desirable Bunggee lake community in Woodstock Valley, this new construction Cape offers approximately 2,230 sq. ft. of finished living space across three levels with 3 bedrooms and 2.5 baths. The main level features an expansive wraparound kitchen, sliders leading to the back deck, and two separate living spaces that can easily adapt to your lifestyle. Create an eat-in kitchen with two living areas, a living room and den, or use one as a spacious formal dining room. A convenient half bath and laundry room complete the first floor. Upstairs are two generous bedrooms, a full bath, and a spacious primary suite with its own private bath and walk-in closet. The finished walkout lower level adds even more flexibility for a family room, home office, gym, hobbies, or additional recreation space and connects directly to the one-car under-house garage. Outside, the private backyard is surrounded by mature trees with a level, open area offering plenty of room for entertaining, gardening, play, or simply relaxing outdoors. The home is nearing its completion, giving you the opportunity to be its very first owner and enjoy all the benefits of new construction without starting from scratch. A great combination of space, privacy, flexibility, and lake-community living! Lake rights and fully recreational amenities offered by Bunggee Lake, including boating, fishing, and swimming opportunities.

61 Red Cedar Rd, Woodstock

$519,000
4 Beds 3 Baths 24200078 MLS
Welcome home to your own private retreat! Set on 1.09 beautifully landscaped acres in a quiet neighborhood, this well built and thoughtfully maintained home offers 4 bedrooms, 2.5 bathrooms, an attached 2 car garage, an inground pool and a private tennis court. Lovingly maintained and ready for your own personal touches, this home offers an incredible opportunity to make it truly your own. The main level features a streamlined kitchen with Corian countertops and a cozy dining area overlooking the patio and pool. Enjoy your morning coffee in the inviting den, complete with a fireplace, custom paneling and built in bookcases. A main level bedroom, half bathroom, formal dining room and spacious living room provide plenty of flexibility for everyday living and entertaining. Upstairs, you will find two additional bedrooms, a full bathroom and a spacious primary suite with its own private bathroom. The finished lower level offers even more living space with a large entertainment area, bar, office, utility area and cedar lined walk in closet. Major updates include a new roof in 2022, windows and driveway in 2020, chimney liner in 2023, pool pump in 2023, resurfaced tennis court in 2022 and sump pump in 2020. Additional features include 200 amp electrical service, a Buderus furnace, attic fan and well expansion tank. Conveniently located approximately 18 minutes from UConn, 17 miles from Norwich and 34 miles from Hartford, this peaceful property offers space, privacy and amenitie

56 Sundale Dr, Windham

$550,000
5 Beds 4 Baths 24198620 MLS
Set on nearly 4 private acres, 21 Linkkila Lane offers the space, flexibility, and peaceful setting that make country living feel special. Start your morning with coffee on the deck while taking in the surrounding landscape and watching the horses at the neighboring horse farm. Inside, this beautifully updated log home strikes the perfect balance between cozy character and clean, modern updates. An abundance of natural light keeps the home feeling bright and airy, while wide plank floors add warmth and charm throughout. A gorgeous brick fireplace anchors the living room, creating an inviting gathering space. The main house features 3 spacious bedrooms, 3 full bathrooms, an extensively renovated kitchen, updated baths, new windows throughout, and a spacious walk-in pantry. Screened-in porches along the back offer additional space to relax and enjoy the peaceful surroundings. A separate in-law suite adds even more versatility with its own kitchen, 2 bedrooms, full bathroom, and separate utilities. Recent improvements include 2 updated kitchens, 4 renovated full bathrooms, new windows in 2025, 2 new water heaters, and refinished decks in 2026. A partially finished basement provides additional usable space and storage. Conveniently located near local schools, UConn, Eastern Connecticut State University, and surrounding towns, this home offers a unique combination of privacy, character, modern comfort, and flexible living.

21 Linkkila Ln, Chaplin

$579,000
4 Beds 4 Baths 73564561 MLS
Custom-built Cape with ADU on 1.62 acres just minutes from Thompson Speedway Motorsports Park, home to a racing track and the Raceway Golf Club, with easy access to 395. This one-of-a-kind property is a true car enthusiast's dream, anchored by a massive eight-car barn garage, ideal for collectors and hobbyists alike. The 1,552 square foot main house offers two bedrooms, hardwood and native pine floors throughout, a custom maple staircase, and French doors leading to an English garden. The kitchen features cherry cabinets and granite countertops, and the dining room includes a fireplace. Upstairs, the primary bedroom opens to a private deck overlooking the backyard. A partially finished basement adds flexible living space, Mitsubishi mini-split heating and cooling keeps every room comfortable, and a whole-house generator offers year-round peace of mind. A two-car garage with a ramp provides convenient access into the home. The property also includes a fully separate 576 square foot accessory dwelling unit with two bedrooms, one bath, a full kitchen, an additional downstairs room, and its own laundry and private garage, perfect as a guest house, home office, in-law or rental. Set in a peaceful country setting in Connecticut's Quiet Corner, this property offers space, versatility, and craftsmanship rarely found together. Subject to seller securing suitable housing. Seller has a next home under contract. Some photos have been virtually staged.

22 Kingsbury Rd, Thompson

$579,000
2 Beds 3 Baths 24199517 MLS
Custom-built Cape with an Accessory Dwelling Unit (ADU) on 1.62 acres just minutes from Thompson Speedway Motorsports Park, home to a racing track and the Raceway Golf Club, with easy access to 395. This one-of-a-kind property is a true car enthusiast's dream, anchored by a massive eight-car barn garage, ideal for collectors and hobbyists alike. The 1,552 square foot main house offers two bedrooms, hardwood and native pine floors throughout, a custom maple staircase, and French doors leading to an English garden. The kitchen features cherry cabinets and granite countertops, and the dining room includes a fireplace. Upstairs, the primary bedroom opens to a private deck overlooking the backyard. A partially finished basement adds flexible living space, Mitsubishi mini-split heating and cooling keeps every room comfortable, and a whole-house generator offers year-round peace of mind. A two-car garage with a ramp provides convenient access into the home. The property also includes a fully separate 576 square foot accessory dwelling unit with two bedrooms, one bath, a full kitchen, an additional downstairs room, and its own laundry and private garage, perfect as a guest house, home office, in-law, or rental. Set in a peaceful country setting in Connecticut's Quiet Corner, this property offers space, versatility, and craftsmanship rarely found together. Subject to Seller securing suitable housing, Seller has next home under contract.

22 Kingsbury Rd, Thompson

$539,000
3 Beds 3 Baths 24199032 MLS
Welcome to 88 Grand View Terrace, where mid-century modern character meets a fresh, thoughtful renovation. Set on a half-acre in an established Brooklyn neighborhood, this beautifully updated home offers an open, light-filled layout with gorgeous hardwood floors, custom lighting and a spacious living/dining area featuring a classic brick fireplace. The brand-new kitchen complements the home's style with warm modern cabinetry, quartz countertops that continue to a full-height quartz backsplash, and striking GE Cafe, matte black appliances. One of the home's standout architectural features is the dramatic open staircase, surrounded by expansive windows that flood the space with natural light while beautifully connecting the upper and lower levels and creating a cohesive flow throughout the home. The upper level features two spacious bedrooms and a designated office, offering flexibility as a potential fourth bedroom or guest room. The completely finished lower level continues the home's polished feel with an additional living area, wet bar and an impressive primary suite complete with an oversized walk-in closet and beautifully remodeled private bath with double sinks and a marble tile walk-in shower. (Glass door and wall to be added prior to closing) Extensive updates include remodeled Kitchen and bathrooms, tile flooring, refinished hardwood floors, updated electrical and plumbing, energy-efficient heating and cooling, a new roof, new thermal-pane windows, doors and more.

88 Grand View Ter, Brooklyn

$500,000
4 Beds 4 Baths 24193694 MLS
Everyone loves a great wrap-around front porch, & this one feels like it was made for slowing down. Wrapped in classic columns & overlooking one of Connecticut's most scenic historic districts, this 1830 home offers 4 bedrooms, 3.5 bathrooms, & over 2,800 square feet filled with original character. Step inside to an elegant oak staircase, original hardwood floors, crown molding, & an interior that reminds you why people continue to fall in love with historic homes. The oversized living room is filled with natural light from dramatic floor-to-ceiling windows. A formal dining room flows into the eat-in farmhouse-style kitchen, where a remarkable brick fireplace once served as the home's original indoor cooking hearth. A first-floor en suite bedroom provides flexibility for guests, multigenerational living, or a private home office, while upstairs you'll find three additional bedrooms plus additional rooms ideal for offices, art studios, a library, or hobby space. Outside, the large rear deck overlooks a just over 3/4-acre, partially fenced lot with plenty of room to entertain, garden, or simply enjoy the outdoors. A new roof installed in 2026, solar panels that help offset electric costs, & a one-car garage add everyday convenience. Located along scenic Route 169 in Brooklyn's historic district, you'll enjoy the charm of Connecticut's Quiet Corner just five minutes from everyday conveniences & approximately 45 minutes from both Providence & Worcester.

31 Canterbury Rd, Brooklyn

$579,900
3 Beds 2 Baths 24193202 MLS
Pristine 1998 Contemporary Cape, situated on 4.62 private and peaceful acres. Built to modern standards, pairing turn-of-the-millennium construction efficiency with a rare, spacious acreage footprint. Modern kitchen features granite countertops, eat-in and island seating, and access to a newly remodeled (2023) Wolf composite deck. The high-quality deck material contains no wood fillers, making it virtually moisture-proof and perfect for outdoor living. Beautiful open floor plan connects the kitchen to a vaulted, beamed, living room, complete with a cozy wood-burning fireplace and abundant natural light from the two-story dormers. Bedrooms & Loft are ideal for both single-level living, with three spacious bedrooms located on the first floor, and a generous loft overlooking the entire lower level, perfect as an office or reading room. The primary bedroom features a walk-in closet and en suite bathroom, fully remodeled in 2023. The second bathroom was remodeled in 2025. A generous lower level is finished with carpeted flooring, includes a full bar, with plenty of space for a den or home gym. Heated by a premium Buderus boiler installed in 2009 and controlled NEST Programmable Thermostats. Outside, your home is guarded by security and Ring Cameras. The easy-to-care-for, spacious level yard abuts a private, treed perimeter. Updates include a new roof and siding (2017, 2018), updated drainage, stonework, and entrance walkway pavers (2019, recently re-sanded

305 Fox Rd, Putnam

$599,000
2 Beds 3 Baths 24187780 MLS
Perfect Countryside Elegance. Welcome to 511 Perrin Road, an exceptional country estate gracefully set atop a private 3.5-acre hillside in scenic Woodstock. A long paved driveway winds through picturesque grounds to this beautifully crafted home, where timeless architecture meets modern efficiency with 100% owned solar. Designed for effortless one-floor living, the residence features a luxurious first-floor primary suite, private executive office, gleaming hardwood floors, exquisite custom built-ins, and an inviting open living and dining area anchored by a dramatic back to back wood-burning fireplace. The custom Brunarhans kitchen is a showcase of quality craftsmanship and thoughtful design. The home boasts 2,393 SqFt of finished living space with 2.5 baths. The second level offers a spacious guest bedroom, full bath, and a connected bonus room, providing exceptional flexibility for family and guests. Step outside to enjoy the serenity of the private patio, a charming pond, and sweeping open grounds. The expansive lawn offers outstanding potential for a boutique vineyard, gardens, or equestrian pursuits, with horses and household pets permitted and ample room for paddocks. Completing this remarkable property is an oversized two-car garage with a private workshop. A rare combination of privacy, elegance, sustainability, and refined country living. A truly exceptional offering in one of Woodstock's most desirable locations.

511 Perrin Rd, Woodstock

$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

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