Ashford Homes under $400,000

Welcome to Ashford, Connecticut, a hidden gem nestled in the heart of Windham County. Known for its picturesque landscapes and charming small-town vibe, Ashford offers a unique blend of rural tranquility and modern convenience. With its lush greenery, serene lakes, and abundant outdoor activities, it’s no wonder that Ashford is a sought-after destination for families and nature enthusiasts alike.

Ashford boasts a rich history and a close-knit community that welcomes newcomers with open arms. The town is dotted with quaint shops, local eateries, and community events that foster a strong sense of belonging. Whether you’re strolling through the historic district or exploring the scenic trails at the nearby Natchaug State Forest, you’ll find that Ashford is a place where life slows down, and neighbors become friends.

For those looking to invest in a home without breaking the bank, Ashford has an array of charming properties available for under $400,000. From cozy single-family homes to inviting townhouses, there’s something for everyone in this price range. These homes often feature spacious yards, modern amenities, and easy access to the town’s natural beauty, making them perfect for first-time buyers or those seeking a peaceful retreat.

In Ashford, you’ll enjoy the best of both worlds: a serene lifestyle surrounded by nature, yet just a short drive from larger cities and amenities. Discover the charm of Ashford today and find your dream home in this wonderful community!

Newest Ashford Homes under $400,000

$399,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24211443 MLS

Numerous improvements have been completed since 2024 at this 3-bedroom, 1.5-bath ranch set on 5.14 acres in Ashford. Updates include a new septic system with basement plumbing, new oil tank, new attic insulation, furnace service, chimney repointing and new chimney cap, tree removal, and professional survey. Inside, the home offers refinished hardwood floors, a bay window, and a beautiful fieldstone fireplace in the living room. The eat-in kitchen features knotty pine cabinetry and a cozy breakfast nook. An enclosed breezeway connects the main house to the one-car garage, providing convenient access and additional storage. Each bedroom offers built-in storage, while the walk-out lower level provides excellent potential for a family room, home office, workshop, or additional living space. The home is also generator-ready with a transfer switch. The property offers privacy, outdoor space, and room to enjoy the peaceful Ashford setting while remaining conveniently located to area amenities and UConn.

108 Krapf Rd, Ashford

$385,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24198024 MLS

One-of-a-kind Ashford home in an extraordinary country setting! Offering approximately 2,866 sq. ft., 4 bedrooms and 3.5 baths, this distinctive home has evolved over the years into a wonderfully flexible floor plan well suited to multigenerational living, working from home or simply spreading out. Character is everywhere, from wide-board wood floors and exposed beams to two fireplaces and a terrific library with extensive built-ins. The spacious kitchen, multiple living areas and combination of first- and second-floor spaces offer possibilities rarely found in a conventional home. Set on 1.71 acres with garage, outbuildings, open yard and wooded surroundings, the setting is equally special. Immediately beyond the property is Joshua's Trust's 60+ acre Josias Byles Sanctuary, with extensive Boy Scouts of America land farther beyond, creating an exceptional backdrop of woods, wildlife and open space. The home is livable now while offering plenty of opportunity for its next owner to make it their own. Refinishing the wood floors, exterior painting and other thoughtful improvements could make a remarkable difference. A truly unusual property for buyers who value space, character, flexibility and nature.

111 Ashford Center Rd, Ashford

$330,000

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24208659 MLS

Situated on a tranquil lot in a quiet Ashford neighborhood, this inviting 2-bedroom, 2-bathroom ranch offers an open floor plan and versatile living spaces across two levels. Step inside to a light-filled main level where the spacious living room features low-maintenance vinyl flooring and glass sliders opening directly onto the back deck. The remodeled eat-in kitchen (2023) boasts sleek granite countertops, generous cabinet storage, and a dedicated eating area for daily meals. Two well-proportioned bedrooms with vinyl flooring and ample closet storage complete the main level, along with a full bath. Downstairs, the partially finished lower level expands your options with vinyl flooring and flexible additional rooms, ideal for a home office, recreation room, and/or gym. Sliders lead out to a private patio overlooking a peaceful, wooded backyard, creating a wonderful setup for outdoor relaxation and quiet mornings. Major recent improvements include a new hot water heater (2024) and a new roof (2025) for added peace of mind. Enjoy the serene setting while staying conveniently connected. The property offers easy access to major highways and state roads, as well as excellent proximity to UConn Storrs, local dining, and surrounding state parks. Schedule your private showing today!

31 Chetelat Dr, Ashford

$219,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24208211 MLS

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 strong potential for multifamily conversion, redevelopment, expansion, mixed-use investment, income-producing use, or possible additional building opportunities, subject to buyer due diligence and local approvals. Ideal opportunity for investors, developers, contractors, or those seeking a long-term development play with substantial upside potential. Conveniently located with ample possibilities for repositioning and future use. Property to be sold strictly as-is. Buyer to perform all due diligence regarding zoning, approvals, permitted uses, subdivision potential, and development possibilities.

259 Ference Rd, Ashford

$389,900

4 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24207835 MLS

Welcome to the Benjamin Clarke House - a grand 1700s center entrance colonial located on a 2-acre country lot - complete with rolling lawn, gardens, restored shed and a pond. Spacious house with much restoration complete - 2 upstairs rooms and a bathroom still to be completed by the new owners. Charm and warmth prevail in this beautiful home, including wide board floors, fabulous stone fireplaces, 1st floor laundry and a woodstove. Poured concrete and stone foundation. A 1-car garage completes this lovely property.

19 North Rd, Ashford

$349,900

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24206405 MLS

Tucked well back from the road, this private property offers room to relax, garden, and make the most of the outdoors. Inside, a great room with soaring cathedral ceilings anchors the open floor plan, while abundant kitchen cabinetry provides plenty of storage. The living area opens to a private deck, and three generously sized bedrooms offer comfortable space for everyday living. The walkout basement is partially finished, with plumbing in place for an additional bathroom in the laundry area. Outside, mature fruit trees and stone walls add character to the grounds, and a farmer's well supplies water for gardening. A spacious workshop garage accommodates up to three cars and offers extensive shelving and storage.

85 Mansfield Rd, 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

$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!

Ashford

$379,000

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24197449 MLS

Lake Life! Year-round Home! Welcome to Ashford CT. 2mi to Rte 84 E/W entrance/exit to Boston, NY or Mass, 12mi to Sturbridge, MA. Easy commute. This home offers spectacular lake access and views. Sunrise to sunset enjoy the amenities of Lake Chaffee Beaches, kayaking, small boats, walks, fishing and much more! The 2009 home shines from head to toe. Enter through the front patio door with room to sit and enjoy the view. flowers and plantings. Hardwood floors, granite kitchen counters and island, stainless appliances, cathedral ceilings, hickory cabinets upgraded to include slide out drawers, corner cabinets and more. Two sets of glass sliders to the front deck makes this home bright and cheery. The Open Floor Plan allows for great conversations. The loft also with sliders to a rear deck. Perfect for guest room, office or to have a morning coffee or evening sip on the deck to sit and relax while you watch the birds or sunsets, beautifully. Full bathroom has a walk-in double shower space. Landscaped with flower gardens. Lots of space in the basement area for storage, An oversized garage with electricity ideal for storage or a workshop. Another convenient storage shed on the lush yard. Propane radiant heat and on demand hot water for optimal efficiency. The Home has lake rights to lake Chaffee, boat launch for small boats. Generator Hook-up in place for your convenience. Come visit to see this amazing home.

290 Ference Rd, Ashford

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