Windham Homes under $400,000

Welcome to Windham, Connecticut, a vibrant town nestled in the heart of Windham County. With its rich history, charming neighborhoods, and a warm sense of community, Windham offers a perfect blend of small-town charm and modern convenience. Known for its picturesque landscapes, this quaint town is surrounded by lush greenery and beautiful parks, making it an ideal spot for outdoor enthusiasts and families alike.

Windham boasts a diverse range of homes, including a fantastic selection of properties priced under $400,000. Whether you’re a first-time homebuyer, looking to downsize, or seeking an investment opportunity, Windham has something to suit your needs. From cozy single-family homes to townhouses and charming bungalows, the real estate market here offers a variety of options that combine affordability with comfort.

The town is also home to excellent schools, vibrant local businesses, and a strong sense of community spirit. Residents enjoy a variety of recreational activities, from hiking and biking in the nearby parks to exploring the local farmers' market, which showcases the best of Connecticut's produce and artisanal goods.

With its convenient access to major highways and public transportation, Windham is perfectly situated for commuters, making it easy to reach nearby cities while enjoying the tranquility of suburban life. Discover the charm of Windham, where you can find your dream home without breaking the bank. Explore the incredible opportunities waiting for you in this welcoming community!

Newest Windham Homes under $400,000

$217,500

4 Beds ⋅ 1 Baths ⋅ 24213182 MLS

Charming Antique Colonial - Prime Windham Location Step back in time and experience the warmth and character of this classic 1915 Antique Colonial, beautifully situated on a desirable corner lot in Windham. This inviting home offers four spacious bedrooms and one full bath, along with a generously sized living room perfect for relaxing or entertaining. The bright eat-in kitchen provides a welcoming space for gatherings and everyday living. Enjoy peaceful mornings or cozy seasonal evenings in the sun-filled three-season room, complete with stairs leading directly out to the backyard. The property is surrounded by a charming white picket fence, enhancing its timeless New England appeal. A standout feature is the impressive two-story garage with access from two streets, offering exceptional convenience, storage, or potential workshop space. The full walk-out lower level adds additional functionality and flexibility. Ideally located close to local colleges, this property presents an excellent opportunity for investors, owner-occupants, or those seeking rental potential. Enjoy nearby delicious eateries, unique shops, and easy commuting access to surrounding towns and major routes. This is a truly charming and classic New England home that must be seen to be fully appreciated.

129 Walnut St, Windham

$84,900

2 Beds ⋅ 2 Baths ⋅ 24212872 MLS

Welcome home to comfort, convenience, and move-in-ready appeal! This lovingly maintained two-bedroom, two-bathroom home, built in 2003, offers thoughtful updates and an inviting setting for everyday living. Updated laminate flooring, tile floors in both bathrooms, and select updated lighting fixtures create a fresh, welcoming feel. All appliances are included, along with the washer and dryer, making your transition that much easier. Enjoy morning coffee on the deck or settle in for a relaxing evening outdoors. With its well-cared-for interior and appealing updates, this home is ready for your personal touches and next chapter. Discover the possibilities and picture yourself at home! Schedule your private showing today.

21 Haley Ln, Windham

$319,900

3 Beds ⋅ 2 Baths ⋅ 24189966 MLS

This lovely home has been thoughtfully updated and well maintained over the years. Recent improvements include a brand-new 40-year roof, beautifully refinished hardwood floors, and fresh paint through the majority of the home. Additional updates include Anderson windows, newer interior and exterior light fixtures, a brand-new beautiful black granite slab for the fireplace, a hatchway, dual oil tanks, rounded archways, and solid six-panel doors. The kitchen features custom-made solid wood cabinetry, including convenient pull-out pantry drawers, along with a newer countertop. The full baths have also been updated, including a second-floor bath with a valuted ceiling, as well as two new toilets. The basement has been freshly sealed, with the walls and floor treated with Drylok for added protection. The exterior was freshly painted including the spacious 14' x 21' deck and is ready for outdoor entertaining. Outside, the property offers a beautiful, open and level lot along with a substantial 12' x 16' outbuilding, providing plenty of space for storage, hobbies, a workshop, or other possibilities. Inside, you'll find spacious bedrooms, with skylights on the second floor bringing in an abundance of natural light. With its classic Cape charm, numerous updates, flexible living space, and generous outdoor areas, this home offers a wonderful combination of character, comfort, and functionality.

75 Mullen Hill Rd, Windham

$299,900

4 Beds ⋅ 2 Baths ⋅ 24211582 MLS

Cute country cape! First floor bedroom, full bathroom and laundry room. Formal dining room and large living room. Three bedrooms upstairs with another full bathroom. Great country porch for relaxing, large Trex deck overlooks the wonderful private backyard. Full basement and outbuilding for storage. A short commute to ECSU, UConn, and shopping. Easy to show!

24 Lovers Ln, Windham

$288,000

3 Beds ⋅ 1 Baths ⋅ 24210578 MLS

Welcome to this well-cared-for home, where thoughtful updates and a comfortable layout create an inviting place to call home. The spacious eat-in kitchen provides plenty of room for meals and entertaining and flows naturally into the living area. The home offers three bedrooms and a well-maintained bathroom. A full walkout basement provides excellent potential space, whether you need a recreation room, home office or workshop. Outside, you'll find a private deck, paved driveway, an a carport for convenient parking and outdoor enjoyment. The roof was newly installed in September 2026, providing an important recent improvement for the next owner. With its comfortable floor plan, outdoor amenities, and opportunity to expand, this home offers plenty of room to make it your own. Situated in a peaceful and desirable part of town, the property is also conveniently located near UConn and Eastern Connecticut State University.

154 Manners Ave, Windham

$269,900

3 Beds ⋅ 1 Baths ⋅ 24210071 MLS

Solid one level home, updated windows, vinyl siding, upgraded to natural gas heat, hardwood floors, potential to finish the basement, utility shed on the lot, all set on a beautiful corner lot off of a quiet cul-du-sac. (note: Town records show the address as Lauter Ave, the street sign is labeled Phillip Lauter Ave.) Oil tank in basement is no longer used, offered with the tank as-is.

149 Lauter Ave, Windham

$349,900

5 Beds ⋅ 2 Baths ⋅ 24210038 MLS

Spacious two-family home offering 5 bedrooms, 2 baths, a large basement, detached garage, covered front porch, and flexible space throughout. Great opportunity for an owner-occupant or investor. Unit 1 offers approximately 1,453 sq. ft. with 3 bedrooms and 1 full bath. The first floor features a large bedroom, spacious living room, kitchen, and full bath, with two additional bedrooms upstairs. The unit also has access to an approximately 1,201 sq. ft. unfinished basement with washer and dryer and plenty of storage space. Unit 2 offers approximately 1,026 sq. ft. with 2 bedrooms and a 3/4 bath. It includes a living room, kitchen, large bedroom with balcony, second bedroom, and approximately 216 sq. ft. of additional attic/storage space on the third floor. The property also includes a 462 sq. ft. detached garage and off-street parking. Convenient opportunity to live in one unit while renting the other, or add a two-family property to your investment portfolio. Furniture shown in the photos can be included with the sale at no additional cost.

19 Bellevue St, Windham

$315,000

4 Beds ⋅ 2 Baths ⋅ 24207636 MLS

Investors and owner-occupants, take notice! This well-maintained two-family home is ideally situated on a quiet dead-end street and offers an excellent opportunity for both rental income and owner occupancy. One unit is currently unoccupied, providing flexibility for a buyer looking to move in while generating rental income from the second unit. Each spacious unit features 2 bedrooms, 1 full bath, and approximately 1,000 square feet of living space, with comfortable layouts and strong rental appeal. Separate utilities simplify ownership and management, while basement laundry hookups provide added convenience for tenants. Set on nearly half an acre, the property offers plenty of outdoor space, a welcoming front porch, and an abundance of off-street parking. Conveniently located near shopping, dining, schools, and major routes, this property combines a peaceful setting with easy access to everyday amenities. Whether you're looking to expand your investment portfolio or take advantage of an owner-occupied opportunity, this versatile two-family property is ready to deliver flexibility, space, and potential. Highest and Best by 8pm Friday 10/20/2026.

11 Type Rd, Windham

$304,900

3 Beds ⋅ 1 Baths ⋅ 24201525 MLS

A delightful gem of a home, this Cape is set in the heart of Willimantic. This home offers easy access to town, shopping, and commuting routes. A charming, move-in-ready opportunity is updated and ready for its next owner, with an open-air plan and unique, tasteful finishing touches throughout. Fresh, modern updates within the last 4 years include: kitchen with granite counters and new stainless appliances (oven/range, microwave, range hood, refrigerator, dishwasher), first-floor bath, carpet in the upstairs bedrooms, newer vinyl siding, windows, roof, and furnace, 3-zone heat for comfort and efficiency. First-floor primary bedroom - easy single-level living, first-floor laundry in the expansive four-season sunroom, sunroom opens to a deck overlooking a very private backyard with stone walls, 3 bedrooms, 1 full bath, 6 rooms total, original wood panel interior doors; updated insulated exterior doors. Added features include, connected Bluetooth speaker in the shower, electric fireplace insert and, under-house 1-car garage plus private driveway (4 parking spaces) and Solar - schedule your tour today!

349 Mansfield Ave, Windham

$70,000

2 Beds ⋅ 2 Baths ⋅ 24203883 MLS

One level living in this mobile home located in Stone Gate Manor. Home offers large, covered deck, nice shed for storage and backs up to woods. Home has a nice open floor plan with a large living room open into the eat in kitchen with lots of good cabinet space. Laundry off kitchen, Primary bedroom has private full bath with shower stall and garden tub, walk in closet. On the other side of Mobile home the second bedroom and another full bath so it is like having two primary bedrooms. Located close to shopping and highways for easy access. Park approval needed

30 Haley Ln, Windham

$189,000

2 Beds ⋅ 1 Baths ⋅ 24205506 MLS

Welcome to 28 Lovers Ln in Windham! This inviting home offers comfortable living spaces and plenty of potential to make it your own. Enjoy a functional layout with bright rooms, generous living areas, and a setting that provides both convenience and privacy. The property offers outdoor space for relaxing, entertaining, or enjoying the changing New England seasons. Conveniently located near local shopping, dining, schools, parks, and major routes, this home provides easy access to everyday amenities while maintaining a peaceful residential feel. A wonderful opportunity to enjoy all that Windham has to offer-schedule your showing today!

28 Lovers Ln, Windham

$82,900

2 Beds ⋅ 2 Baths ⋅ 24204985 MLS

Welcome to this well-maintained 2-bedroom, 2-full-bath mobile home located in Stonegate Manor, offering a comfortable and functional floor plan. The primary bedroom features a private full bath and walk-in closet, while the two bedrooms are thoughtfully situated at opposite ends of the home for added privacy. The fully applianced kitchen includes a convenient snack bar, with a dedicated laundry area down the hall. Enjoy the added comfort of Central Air Conditioning throughout the home. A newer roof (2021) and updated windows adds peace of mind, while the 12x12 roofed deck provides a great space for relaxing. A storage shed adds additional convenience. While the home retains some original finishes, it has been well cared for, is clean, and move-in ready. Conveniently located near shopping, restaurants, gas stations, and other everyday amenities, this home offers comfortable living in a convenient location. Park approval is required. Monthly park fee is $769

29 James Dr, Windham

Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.