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

29 Marcy Ln, Thompson
$599,900
3 Beds ⋅ 3 Baths ⋅ 24215871 MLS
Discover a truly unique property offering three full levels of versatile living space, exceptional privacy, and an outdoor setting designed to be enjoyed in every season. The main level welcomes you with a grand family room featuring soaring vaulted ceilings, a walkout to the expansive rear deck, and a charming front sitting porch. The beautifully renovated kitchen showcases butcher block countertops, stainless steel appliances, and a stunning center island, complemented by a dedicated dining area with a custom coffee station and bay window that fills the space with natural light. An elegant arched doorway leads to a second living room featuring a propane gas fireplace, creating a warm and inviting retreat. A full bathroom with a beautifully designed tiled shower and French doors opening to a private deck complete this level. Upstairs, you'll find three bedrooms, including a spacious primary bedroom with ample room for additional furnishings, along with a flexible bonus room ideal for a home office, guest room, or additional bedroom. A full bathroom with a convenient in-home washer and dryer adds everyday functionality. The fully finished lower level expands the possibilities even further, offering a private room currently used as a bedroom, an additional common area currently set up as a workout room, and a third full bathroom with a tub and shower. Set on nearly five private acres, the outdoor amenities are just as impressive.

29 Marcy Ln, Thompson

33 Machine Shop Hill Rd, Windham
$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

15 Margaret Henry Rd, Killingly
$565,000
3 Beds ⋅ 3 Baths ⋅ 24210184 MLS
Discover the charm of Connecticut's Quiet Corner! Set on a beautiful, level 5+-acre lot, this spacious modern 3 bedroom colonial home offers the perfect blend of privacy, recreation &convenience. This move in ready home features a tremendous amount of updates including newer roof, siding, windows, pool liner and chimney plus updated kitchen! Wood Spacious open floor plan showcases and updated kitchen with granite counters, newer appliances and an abundance of cabinetry plus generous dining area with sliders and access to the oversized deck. The fireplaced family room with 4 casement windows allows an abundance of natural light to flow in, a large living room provides extra space for entertaining during the holidays and 1st floor laundry for convenience. Upstairs features 3 generous sized bedrooms with ample closet space. Primary bedroom with updated full bath plus 2 additional bedrooms with generous closet space. An oversized 2-car garage provides additional storage, while abundant off-street parking accommodates boats, RVs, trailers and other recreational vehicles.The property is an outdoor oasis featuring an inviting in-ground pool, patio (updated) and deck areas perfect for summer entertaining. Think ahead! In winter, the expansive acreage offers plenty of room for ATV fun and outdoor recreation. A rare metal outbuilding with electricity, overhead door and possible access to Route 6, is ideal for collector cars, motorcycles, equipment, workshop space or other hobbies

15 Margaret Henry Rd, Killingly

54 Westford Rd, Eastford
$574,900
3 Beds ⋅ 2 Baths ⋅ 24212900 MLS
Step onto this property and you are immediately taken with its beauty. Mature landscaping filled with ornamental and native trees including 1000's of spring bulbs, summer lilies, and other perennials surrounded by the stone walls that characterize so much of New England charm. This 1900's home has been carefully updated to highlight its character and history with all the conveniences we have learned to love. The entry way welcomes you with vintage cherry floors, The kitchen has been completely remodeled with new cabinets, quartz countertops, and new appliances. The back ell consists of a walk-in pantry, an oversized mud room with laundry and new 3/4 bath as well as an office with private entrance on the first floor. Spacious Dining room, featuring Washington fir floors is right off the kitchen. The large living room with fireplace, is open to sunroom/family room with ample space for you to spread out and enjoy entertaining. A beautiful staircase leads to three bedrooms, all with wood flooring and remodeled full bathroom. There are possibilities for an in-law suite with not too much effort. Refinished plaster walls and fresh paint throughout. Almost 4 acres gives you room to spread your wings. Open field, perfect for grazing your animals. Concrete pad, ready for your new garage or barn. Most windows replaced; roof on the ell of the house is brand new. Mechanicals are up to date. Ready to for you to move right in!

54 Westford Rd, Eastford

1 Corttiss Rd, Thompson
$500,000
3 Beds ⋅ 3 Baths ⋅ 73580137 MLS
SELLER OFFERING CLOSING COST CREDIT!"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

813 Westford Rd, Ashford
$533,000
3 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

1 Corttiss Rd, Thompson
$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

4 Oak Dr, Woodstock
$539,000
2 Beds ⋅ 2 Baths ⋅ 24201418 MLS
There's something special about seeing the lake from home and being 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. Offering deeded lake & beach rights and water views, simply walk across the street to the boat launch and enjoy easy access to the lake. This newer home sits on an inviting corner lot surrounded by colorful flowers and raised vegetable gardens, plus an oversized shed less than a year old for additional storage. Traditional stone walls along the adjoining historic cemetery add to the peaceful New England setting. Inside, the open-concept kitchen with granite countertops and center island flows comfortably into the dining and living areas, with plenty of natural light and views toward the lake. Step onto the deck to unwind and enjoy the glowing sunsets. Both bedrooms are on the main level, including the primary with a large walk-in closet, private full bath and sliders to its own deck. Upstairs, the spacious loft offers flexible additional living space, two closets and attic storage. The full walk-out basement with sliders provides excellent storage and potential for future finished space. Generator hookup ready. Lovingly maintained and move-in ready, this welcoming home offers a wonderful place to enjoy the lake, the seasons and the simple pleasures of home, conveniently located near the MA line and area amenities.

4 Oak Dr, Woodstock

1015 North Rd, Killingly
$565,000
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

61 Red Cedar Rd, Woodstock
$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

21 Linkkila Ln, Chaplin
$525,000
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

88 Grand View Ter, Brooklyn
$519,900
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

272 Horse Hill Rd, Ashford
$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

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