Windham Homes under $250,000

Welcome to Windham, Connecticut – a charming town nestled in the heart of Windham County, where rich history meets modern living. Known for its picturesque landscapes and vibrant community spirit, Windham offers a unique blend of rural charm and urban convenience. With its historic downtown area, scenic parks, and friendly neighborhoods, it’s no wonder that Windham is a sought-after destination for families, young professionals, and retirees alike.

For those seeking affordable housing options, Windham presents an incredible opportunity with homes available for under $250,000. This affordability does not compromise on quality; you’ll find a variety of charming properties that cater to diverse lifestyles. Whether you're looking for a cozy single-family home, a quaint bungalow, or a well-maintained townhouse, Windham has something to fit every taste and budget.

Imagine settling into a welcoming community where you can enjoy local festivals, farmers' markets, and outdoor activities year-round. With easy access to major highways, commuting to nearby cities is a breeze, making Windham an ideal location for those who work in Hartford or surrounding areas.

In Windham, you’re not just buying a house; you’re investing in a lifestyle rich in culture, community, and natural beauty. Explore the possibilities today and discover the perfect home that suits your needs without breaking the bank. Embrace the charm of Windham and make it your new home!

Newest Windham Homes under $250,000

$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

$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

$135,000

3 Beds ⋅ 2 Baths ⋅ 24204778 MLS

This Cute, Clean and Spacious, 3-bedroom, 2 bath home in the Stonegate Manor has 1152 Square Feet of Living Space. Appliances convey. There is an 8x10 Shed that conveys as well. Updates are as follows.... Roof is only 2 years old, and hot water heater only 3-4 years old. New flooring and subflooring in primary bedroom/bath. 2 pets are allowed per park regulations. Park has No age requirement! This home abuts the woods with a Walking Trail leading to the Willimantic Reservoir and surrounding Natchaug River and Mansfield Hollow watershed system. Close to Route 6, Airport, shopping, restaurants and more. Public water and public sewer.

57 Circle Dr, Windham

$179,999

4 Beds ⋅ 2 Baths ⋅ 24201064 MLS

Bring your vision to this four-bedroom home in Willimantic's Hill Section. With approximately 1,807 square feet of living space, the property features generously sized rooms, tall windows, original woodwork, and period details throughout. With thoughtful updates, this home has the potential to showcase its original character while being tailored to its next owner. Conveniently located near downtown Willimantic, Eastern Connecticut State University, shopping, dining, and major routes. Property is being sold as-is. Also available is 11 Bellevue Street, located behind the property, creating the possibility of a package purchase. One of the parties to the LLC has an active real estate license.

15 Bellevue St, Windham

$159,999

6 Beds ⋅ 2 Baths ⋅ 24201036 MLS

Bring your vision to this six-bedroom home in Willimantic's Hill Section. With approximately 1,948 square feet of living space, the property features generously sized rooms, hardwood flooring, tall windows, original woodwork, and period details throughout. A brand-new roof has already been installed, providing a great start for future improvements. With thoughtful updates, this home has the potential to showcase its original character while being tailored to its next owner. Conveniently located near downtown Willimantic, Eastern Connecticut State University, shopping, dining, and major routes. Property is being sold as-is. Also available is 15 Bellevue Street, located at the front of the property, creating the possibility of a package purchase. One of the parties to the LLC has an active real estate license.

11 Bellevue St, Windham

$199,900

2 Beds ⋅ 2 Baths ⋅ 24197730 MLS ⋅ Elm Tree Village BLDG.

FRESH PAINT TO COME! Seller will be painting downstairs bathroom and living room with neutral tones! Welcome to 29 Kathleen Drive, Unit 3B, a spacious two-bedroom townhouse-style condo offering a flexible layout, finished lower level, and comfortable everyday living. This is one of the few units with a Finished Basement! The main level features an inviting living area with an easy flow for everyday living, while central air keeps the home comfortable through the warmer months. Upstairs are two well-sized bedrooms and a full bath, and the finished lower level adds valuable flexibility for a family room, home office, gym, playroom, or hobby space. With 1.5 baths, natural gas heat, and the convenience of condo living, this home offers a practical layout with room to spread out. Set within the established Elm Tree Village community, residents can also enjoy shared outdoor amenities including tennis courts and picnic areas. Conveniently located near Eastern Connecticut State University, shopping, dining, and major routes, this is an easy-to-manage home with versatile living space and a location that keeps everyday essentials close by.

29 Kathleen Dr Unit 3B, Windham

$126,900

2 Beds ⋅ 1 Baths ⋅ 24194799 MLS

Totally remodeled conveniently located in N. Windham in the much desired Stonegate Park. 2 bedroom, one bath with a new Trex Deck with new solar lighting installed in 2026. This deck overlooks a beautifully landscaped yard. The home is located on a dead-end and close to many amenities. You won't be disappointed, inside you will find a freshly painted home, new rugs, new appliances ranging from 2024-2026, new kitchen counter, sink etc.2026 New 40-gallon water heater 2024, new furnace 2024, 2nd propane tank 2025. Plex tubing throughout 2024. Nothing for you to do. Come take a look you won't be disappointed.

57 James Dr, Windham

$210,000

2 Beds ⋅ 2 Baths ⋅ 24190308 MLS ⋅ Elm Tree Village BLDG.

Move-in ready 2-bedroom, 1.5-bath townhouse-style condo offering comfortable, low-maintenance living in a desirable community. The main level features a spacious living room, a kitchen with updated appliances, designated dining area and a convenient half bath. Upstairs are two generously sized bedrooms and a full bathroom. The full basement provides abundant storage, washer and dryer hookups, and potential for additional finished living space. Major mechanical updates include a new heating system, central air conditioning, and water heater, all replaced within the past year. Additional highlights include an attached one-car garage, driveway parking for two vehicles, and access to community tennis courts. Conveniently located near shopping, restaurants, and major routes while offering a quiet residential setting. A great opportunity for owner-occupants or investors alike.

29 Kathleen Dr Unit 5C, Windham

$224,900

3 Beds ⋅ 1 Baths ⋅ 24170683 MLS

Well-maintained 3-bedroom ranch located on a quiet dead-end street. This 960 sq. ft. home offers convenient one-level living with an eat-in kitchen, spacious living area, and a full unfinished basement providing ample storage and future potential. Situated on a level lot, the property features a fenced backyard, mature shade trees that enhance curb appeal, and a wooded backdrop beyond the rear fence for added privacy. Ample off-street parking. Lovingly cared for over many years and ready for its next owner to add their own updates and personal touches.

147 Orchard Hill Ln, Windham

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