Ashford Real Estate

Welcome to Ashford, Connecticut – a hidden gem nestled in the picturesque Windham County. With its rich history, stunning natural landscapes, and vibrant community spirit, Ashford offers a unique blend of rural charm and modern convenience that makes it an ideal place to call home.

As you explore Ashford, you'll be captivated by its scenic beauty, characterized by rolling hills, lush forests, and serene lakes. The town is a haven for outdoor enthusiasts, with numerous hiking trails, fishing spots, and parks that invite residents to immerse themselves in nature. The nearby Mashamoquet Brook State Park is perfect for family outings, offering picnic areas and trails that wind through enchanting woodlands.

Ashford boasts a strong sense of community, with local events and festivals that bring residents together throughout the year. The town's rich history is reflected in its well-preserved architecture and charming downtown area, where you can find quaint shops, delightful eateries, and friendly faces. The local farmers' market is a must-visit, showcasing the best of Connecticut’s produce and artisanal goods.

Education is a priority in Ashford, with highly-rated schools dedicated to fostering a nurturing environment for students. The town’s commitment to community engagement and safety makes it an excellent choice for families and individuals alike.

With its perfect blend of tranquility and accessibility, Ashford is conveniently located near major highways, making it easy to reach larger cities while enjoying the peacefulness of small-town living. Discover the warmth and charm of Ashford, where every day feels like a breath of fresh air. Come and experience the beauty and community spirit that await you!

Newest Listings in Ashford

$349,900

3 Beds ⋅ 2 Baths ⋅ COMING SOON Status ⋅ 24206405 MLS

welcome to this very private set way off the road treasure This home has high cathedral ceiling great room with lots of cabinets open floor plan to private deck 3 nice size bedrooms half of the basement is finished walkout. plumbing is in placed for an additional bath in the laundry room location. This property is full of mature fruit trees stone walls and to top it off a huge workers garaged can fit up to 3 cars in there with loads of shelving and storage area.

85 Mansfield Rd, Ashford

$533,000

5 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 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

$429,500

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24204485 MLS

This thoughtfully renovated three bedroom, two full-bath raised ranch sits on an impressive 1.3 acres on Lake Chaffee. This home features an updated electrical system, new propane boiler, new windows with custom blinds, new appliances, an eat-in kitchen and a separate breakfast nook. Additionally, this property offers an attached two car garage and a dedicated gym area/bonus room offering flexible additional space. Enjoy beautiful lake views from the spacious deck overlooking the lake, along with beach and lake access for year-round enjoyment. Experience paddle boarding, kayaking, swimming, even ice skating and ice fishing in the off season, practically in your front yard. A unique combination of privacy, space, modern updates, and lakefront lifestyle in desirable location! Contact the listing agent for a list of all renovations completed.

76 Lakeview Dr, Ashford

$384,900

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24205788 MLS

Lakefront living at its best on beautiful Lake Chaffee! This considerately renovated two bedroom, one full-bath cottage offers the perfect blend of charm, comfort, and modern updates. Features include a versatile loft, propane heating stove, generator hookup, new roof, and new electrical and plumbing throughout. Enjoy relaxing or entertaining on the spacious deck overlooking the lake, with a walkway leading directly to your private dock and lake access. A wonderful opportunity to enjoy year-round or seasonal lakeside living in a desirable location! Contact list agent for a list of all renovations completed.

73 Lakeview Dr, Ashford

$380,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24203220 MLS

Welcome to 21 Deerfield Dr in Ashford! This beautifully updated 3 bed, 2 bath home offers 1,872 square feet of finished living space and is located within the Lake Chaffee community. The open floor plan creates an easy flow throughout the main level, featuring an updated kitchen, spacious living and dining area, primary bedroom with full bath, and convenient first-floor laundry. The finished lower level offers even more space with fresh carpeting and a flexible space ideal for both an entertaining space and bedroom, home office, gym, or playroom. The property is part of the Lake Chaffee Improvement Association with an annual fee for plowing, road & lake maintenance. The sale also includes an additional .24-acre lot located directly across the street, providing added space and potential.

21 Deerfield Dr, Ashford

$219,000

2 Baths ⋅ ACTIVE Status ⋅ 24204279 MLS

*Property recently has been fully cleaned out*. 20 minutes from UCONN. Rare value-add and redevelopment opportunity situated on 3.5 acres with over 3,200 square feet of existing space. Currently configured as a mixed-use commercial property, this expansive parcel offers outstanding potential for residential conversion, multifamily redevelopment, mixed-use investment, expansion, or additional development, subject to buyer due-diligence and all required approvals. Engineering plans/evaluation, septic design plans, and soil testing have already been completed to evaluate the feasibility of residential conversion, providing a valuable head start for future development. No municipal approvals have been obtained. Ideally located on Route 89 with excellent visibility and convenient access to UCONN, this property offers exceptional potential for investors, developers, shop owners, contractors, seeking a long-term value-add opportunity. Recent Connecticut housing legislation encouraging additional housing development may further enhance the property's future potential, subject to applicable laws, zoning requirements, and municipal approvals. Property is being sold strictly as-is. Buyer is responsible for verifying all zoning, permitted uses, engineering, approvals, subdivision potential, and development opportunities.

259 Ference Rd, Ashford

$399,900

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24203208 MLS

Agricultural animal zoned property tucked privately back from the road on 6.76 secluded acres. This truly unique reproduction Antique Saltbox evokes the feeling of stepping back into an earlier New England era. Built in 1994 with remarkable rustic character, the home features wide-plank wood flooring, exposed beams and materials sourced from the property itself. The spacious interior offers an open floor plan on the first floor with lots of windows and natural light and includes an office and 4th bedroom. On the second floor are 3 bedrooms including a fireplaced primary bedroom with walk-in closet. The main second floor full bath was designed with walk in shower and oversized jetted tub. A walk-out basement provides a workshop and additional storage space.For those dreaming of a horse property, hobby farm or a quieter way of life connected to the land, the impressive 28' x 32' barn offers 2 stalls and space for substantial vehicle/equipment storage. A full second-floor loft has potential for finishing. Stone walls adorn private wooded land and an electric fence further enhance the quintessential farm style country setting.The home requires some restoration to return it to its original beauty, and has been priced accordingly. For the buyer who appreciates authenticity, craftsmanship and the timeless appeal of rural New England, this is a property unlike most others. Buyer to perform due diligence regarding their intended animal or agricultural use.To convey as seen and as-is.

138 Krapf Rd, Ashford

$425,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24201631 MLS

Fully remodeled from top to bottom in 2021, this beautiful 1,996-square-foot Colonial seamlessly blends modern updates with timeless charm. Featuring 3 spacious bedrooms and 3 full bathrooms, this inviting home offers plenty of space for comfortable everyday living and entertaining. The open lower-level floor plan creates a warm, welcoming flow with flexible living spaces designed to fit a variety of needs. The updated kitchen features granite countertops, adding both style and durability to the heart of the home. Upstairs, you'll find three generously sized bedrooms and two full bathrooms, including a private primary suite with an ensuite bathroom and walk-in closet. A true standout is the impressive 720-square-foot detached outbuilding, offering endless possibilities as a workshop, studio, home business, hobby space, or barn. Whether you need additional workspace, storage, or a creative retreat, this versatile structure provides exceptional flexibility. With extensive 2021 renovations, a thoughtfully designed layout, open living spaces, and an outstanding detached outbuilding, this property is truly move-in ready and ready to welcome its next owner. A nice combination of country setting, modern comfort, and incredible versatility!

307 Mansfield Rd, Ashford

$599,900

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24202476 MLS

Tucked away on more than 12 acres in the peaceful countryside of Ashford, this contemporary 4-bedroom, 2.5-bath home offers an incredible sense of privacy while still providing plenty of space both inside and out. Surrounded by mature trees and natural beauty, the property feels like its own private retreat. Inside, hardwood flooring mini split systems for central air, and abundant natural light create a warm and inviting atmosphere throughout the main living spaces. The spacious kitchen offers plenty of cabinetry and counter space, while the adjoining dining area opens directly to the large back deck, creating an easy flow for everyday living and entertaining. The primary suite is a standout, featuring its own full ensuite bath and private balcony overlooking the wooded surroundings-the perfect place to enjoy a quiet morning or unwind at the end of the day. Three additional bedrooms provide plenty of flexibility for family, guests, a home office, or hobby space. Take advantage of the efficiency and savings the solar panels that are owned outright provide! Outside is where this property truly shines. The expansive 12+ acre setting offers a rare level of seclusion, with a mix of open lawn and surrounding woods creating a peaceful backdrop in every direction. A large deck extends the living space outdoors and provides plenty of room for entertaining, relaxing, or simply taking in the scenery.

120 Cushman Rd, Ashford

$489,999

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24201756 MLS

Have you ever wanted your own private backyard beach with private dock? This turnkey, one-level, direct waterfront, year-round home has its own private beach, completed in 2025, along with numerous recent upgrades. Non-motorized watercraft & outboard motors 5 horsepower or less are permitted on the lake by property owners & guests only. Included are several kayaks with a stand, paddle boat, patio set, new shed, floating doc and other outdoor seating, along with custom furniture inside to fit the home in the living room, sunroom, kitchen, and a newer TV w/ wall mount. The relaxing sunroom offers beautiful views of the water and features a new large Anderson picture window with professionally installed remote control blinds and a sliding door out to the deck. This exterior offers easy maintenance with vinyl siding, a newer roof, and composite decking. New foam insulation was installed in 2025. The interior offers commercial-grade laminate floors throughout, and the spacious kitchen is updated with quality-crafted cabinets with pull-out drawers. Entering into the kitchen and living room/dining area are an open floor plan with a brick fireplace. The large master bedroom was completed recently by combining a 2nd bedroom and is on the other side of the kitchen with a 2nd smaller room that's listed as a bedroom currently being used as a storage room and does have the washer and dryer included.

60 Ashford Lake Dr, Ashford

$650,000

5 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24198311 MLS

Here's your opportunity to have the feeling of a little piece of Vermont while being in Connecticut. About 7 minutes to the highway and 10 minutes to UConn. 17.3 acres creating such a unique setting. Knowlton Brook Runs through the property feeding a beautiful pond. The property is surrounded by treed areas with a lot of nature's feeling integrated into the living areas of the property. Tranquil is an understatement. First floor of this home has three bedrooms, primary bedroom has private bath, Main bath, living room, dining room, kitchen and family room. There is a lower-level rec room and an additional half bath. The Lower-level In-law apartment has private entry, 2 bedrooms, living room, kitchen and a full bath. Two car garage. Two-story barn.

97 Cushman Rd, Ashford

$385,000

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24196755 MLS

Experience a secluded Ranch in the pretty-as-picture setting of a Rural Community of Ashford, CT. Enjoy 2 acres of Private Country living. Property includes a small Horse stall and a newly built enormous 24' X 30' garage for all sorts of hobbies or mechanical recreation. The home boasts a spacious Master Bedroom with a walk-in closet. A second bedroom on the main floor and one on the lower level, which can be used for a third bedroom or office. The comfortable eat-in kitchen has a corner built-in, not far from the generous Sun-filled Living room. This home has been in the family for many years. It is updated and well taken care of. This Rustic location will serve your family for many years to come. Plenty of space for a pool, vegetable garden, flower garden, and your FOREVER DREAMS!

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