Windham County, CT Real Estate Search

Windham County, CT Homes between $250,000 and $300,000 for Sale

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Newest Windham County, CT Homes between $250,000 and $300,000 for Sale

$293,000
3 Beds ⋅ 1 Baths ⋅ 24205667 MLS
Welcome to 10 Centennial Street! This charming 3-bedroom, 1-bath home offers a great combination of comfort, updates, and plenty of potential. Recent improvements include an updated roof, heating system, flooring, and appliances, giving the next owner a great head start. Inside, you'll find a comfortable and functional layout with plenty of opportunity to add your own personal touches and truly make the space your own. Whether you're a first-time buyer, downsizing, or looking for a home where you can build equity over time, this property offers lots of possibilities. An oversized detached two-car garage adds even more value, providing excellent space for parking, storage, a workshop, or hobbies. Conveniently located near local amenities, shopping, dining, and major routes, 10 Centennial Street is a wonderful opportunity to bring your vision and make this home your own!

10 Centennial St, Putnam
$267,000
6 Beds ⋅ 2 Baths ⋅ 24205724 MLS
Seller says Sell Sell Sell.. Looking for your next investment property?? Look no further. If you been searching for a home that's move in ready, while allowing you to update it at your own pace, this is it! With solid bones and only cosmetic improvements needed, this is a fantastic opportunity to create instant equity. While generating income at same time... Solar on property is not owned Buyer and buyer agents to do due diligence on solar. bank requires owner occupied borrowers for solar loan.

144 Prospect Ave, Killingly
$285,000
3 Beds ⋅ 1 Baths ⋅ 24204890 MLS
Welcome to 3 Bristol St! Tucked away in a quiet Windham neighborhood, this well cared for home is a gardeners dream! Surrounded by established perennial gardens and fruit trees, the property offers a peaceful, tranquil setting while remaining just minutes from downtown and University areas. The flexible floor plan provides plenty of options, including an office that could easily be another bedroom or flex space. The inviting country kitchen features a center island and beautiful wide plank flooring, creating a warm and comfortable gathering space. Outdoor enthusiasts and gardeners will love the established landscaping, fruit trees, and the opportunity to keep the chickens. The chicken coop can be included with the sale. Recent improvements include a split-ductless heating and air conditioning system, REEM water heater, newer windows, updated flooring, crown moldings and a sewer line connection. Available for immediate occupancy!

3 Bristol St, Windham
$285,000
1 Beds ⋅ 1 Baths ⋅ 24201537 MLS ⋅ River Walk Condominiums BLDG.
Enjoy carefree one level living in the Beautiful River Walk over 55 Condo Complex. You'll love the open floor plan where the kitchen and dining area flows into the large living room with cathedral ceilings and big windows for great natural light. There's a spacious primary bedroom with double closets for plenty of storage, and an additional room that's perfect for an office or study. In the bath you'll find a double vanity, walk-in shower and stackable washer and dryer. Radiant propane heat and central air will keep you comfy all year. The attached garage walks right into the kitchen for ease in bringing in the groceries. Enjoy the peaceful outdoors on the inviting front porch or your rear patio with privacy fence. Just off Allen Hill Rd, minutes to Route 6 & 395. Quiet country living at its best!

21 River Walk Dr Unit 21, Brooklyn
$299,900
3 Beds ⋅ 2 Baths ⋅ 24203286 MLS
Bring your ideas and make this 3-bedroom, 1.5-bath ranch your own! Situated on a .58-acre lot, this home offers a great layout with plenty of potential for someone ready to add their personal touches. Enjoy the convenience of first-floor laundry, an attached garage, and a full walk-out basement offering plenty of storage and possibilities for additional space. A newer water heater is already in place. The home does need some TLC and updating, but with a little work, it could really shine. A great opportunity to build some sweat equity and create a home that's truly your own.

35 Gilman St, Putnam
$279,900
3 Beds ⋅ 2 Baths ⋅ 24201681 MLS
Welcome to this 7 room, 2 bath, ranch style home, with a detached garage, located on 2 Acres. set back off the road. If you have been looking for country living, this may be your home. Fully applianced kitchen (laundry set-up conveniently located), Kitchen eating nook, plus a formal dining room. All located on one floor living. Bring your ideas. lots of potential to make it your own.

337 Hampton Rd, Chaplin
$290,000
3 Beds ⋅ 1 Baths ⋅ 24203002 MLS
Charming, Cozy, and 100% Move-In Ready! Everything has been done for you! Just three short years ago, this adorable 3-bed, 1-bath home received a complete tune-up, including a new roof, modern mechanicals, and a stylishly updated kitchen with modern appliances. Loved for its practical layout, you'll find main-floor laundry right where you need it. Step outside to your private, level backyard-a perfect canvas for gardeners, weekend BBQs, or late-night stargazing by the shed. Just unpack and start living!

19 River St, Plainfield
$290,000
4 Beds ⋅ 2 Baths ⋅ 24201649 MLS
INVESTOR OPPORTUNITY IN WILLIMANTIC! Bring your vision to 86 Chestnut Street, an approximately 1,560 SF multifamily property. Originally built in 1887, the property offers timeless architectural character and charm rarely found in newer construction. Conveniently located near downtown Willimantic, Eastern Connecticut State University, shops, restaurants, services, and major area routes. Offered AS-IS, providing an opportunity to renovate and customize to your investment strategy. The property's character, layout, location, and value-add potential make this an excellent opportunity for an investor or owner-occupant. Cash or conventional financing only. No government financing. Buyer to conduct their own due diligence regarding condition, zoning, intended use, and renovation potential.

86 Chestnut St, Windham
$289,900
2 Beds ⋅ 2 Baths ⋅ 24200050 MLS
Spacious mixed-use current 3 unit but possible 2 family located in the heart of town offering endless possibilities for investors, business owners, or owner-occupants. The first floor features two commercial storefronts with excellent visibility and foot traffic, ideal for retail or officeThe second floor offers a well-sized 2-bedroom apartment providing additional rental income or owner occupancy potential. Centrally located in town near the post office, local amenities with strong exposure and flexible usage opportunities. A unique opportunity to own an income-producing property with commercial and residential versatility.

8 Palmer Rd, Scotland
$295,000
2 Beds ⋅ 2 Baths ⋅ 24199710 MLS ⋅ Cottages At Pomfret BLDG.
A rare opportunity at The Cottages at Pomfret! This turnkey townhouse is full of charm and offers easy, comfortable living in a peaceful Pomfret setting. Step inside to a welcoming main level with a spacious living area, kitchen and dining space, all designed for an easy flow whether you're entertaining or simply relaxing at home. Just outside, an extended paver patio creates a lovely outdoor extension of the living space- perfect for morning coffee, summer dinners, a little gardening or unwinding at the end of the day. Upstairs, you'll find two comfortable bedrooms plus a surprisingly spacious additional room currently being used as a third bedroom, offering wonderful flexibility for guests, a home office, hobby space or whatever best suits your lifestyle. With 1.5 baths, central air, an attached garage and an unfinished basement providing plenty of additional storage, this home offers the right combination of comfort, practicality and versatility. Move-in ready and tucked within an established condominium community, this is your opportunity to enjoy low-maintenance townhouse living and all the charm of Pomfret.

234 Killingly Rd, Pomfret
$289,900
3 Beds ⋅ 1 Baths ⋅ 24198984 MLS
"First-floor living at its best! This charming 3-bedroom home features beautiful hardwood floors, a cozy fireplace for those cool New England evenings, and a whole-house generator to keep you comfortable when the power goes out. Situated on a desirable corner lot, the property also offers a paved driveway, storage shed, and convenient access to I-395. A wonderful opportunity for comfortable and convenient living in a great location."

28 Daggett St, Plainfield
$299,000
6 Beds ⋅ 2 Baths ⋅ 24193499 MLS
This two-family property offers solid bones and strong potential. Each unit provides a functional layout with 3 bedrooms and ample space including finished walk-up attic. Home has been used as a single family for the last 20 year's second floor kitchen needs to be reinstated. Ideal for investors, contractors, or owner occupants looking to build equity, this home needs work but delivers a great opportunity to create long-term value. Conveniently located in the heart of Putnam near local amenities and major routes, this property is a chance to transform a multi-unit home into a reliable income producing asset.

57 Wilkinson St, Putnam
$280,000
2 Beds ⋅ 2 Baths ⋅ 73564030 MLS
Welcome to Unit 2 at 18 Ballou Street in Putnam! This beautifully remodeled home offers a fresh, move-in-ready interior with a functional layout and plenty of additional space.The main level features hardwood floors throughout the living and dining areas, creating a bright and open space for everyday living and entertaining. The updated kitchen flows conveniently into the dining area and provides access to the back deck.Upstairs, you’ll find two bedrooms along with a full bathroom, keeping the sleeping areas separate from the main living space.The attached garage provides secure parking and additional storage, plus a bonus room located directly off the garage. This flexible space offers plenty of possibilities for a home office, gym, gaming room, hobby area, or private hangout space.With remodeled living spaces, hardwood floors, an attached garage, private deck, bonus space, and a convenient Putnam location, Unit 2 offers a great combination of comfort, functionality, and value.

18 Ballou St Unit 2, Putnam
$299,900
3 Beds ⋅ 1 Baths ⋅ 24198542 MLS
A rare opportunity to create your own waterfront retreat on Alexander's Lake. This 3-bedroom, 1-bath home offers 1,282 square feet of living space with direct lake frontage and a setting that's hard to beat. Inside, you'll find a spacious living area with a brick fireplace and stone flooring, along with a sunroom positioned to take in the water views. Step outside onto the large deck overlooking the lake, with direct access to the water just steps away. The home is ready for renovation, giving the next owner the opportunity to update the space while taking full advantage of its waterfront location. Spend your days kayaking, paddleboarding, fishing or boating on Alexander's Lake, where electric motors only are permitted. Property is located on leased land and sale is subject to Probate Court approval. A little work, a great setting, and plenty of potential-bring your vision and create your own place on the lake.

111 Island Rd, Killingly
$299,900
4 Beds ⋅ 1 Baths ⋅ 24195103 MLS
Should go ANY Financing! HUGE 16 x 19 DECK to enjoy your Summer evenings! 4 Bedrooms with NEW Carpet! LARGE family room w/ Woodstove and NEW carpet, Laundry area w/ 2 bedrooms on lower level. Main level has NEW flooring in living room and hallway big bay window for natural light. BRAND NEW cabinets, counter, sink and has appliances too with NEW flooring in eat in kitchen. Slider leads to deck. Bathroom has NEW vanity, toilet and flooring. City water, sewer, 2026 hot water heater and shed conveys. LOW TAXES!

39 Beechwood Blvd, Plainfield
$274,900
4 Beds ⋅ 2 Baths ⋅ 24193997 MLS
Offered for the first time in 24 years and loaded with high-ticket updates, this spacious 1648 ft.2 Cape Cod offers four bedrooms, two full baths, and is set on a private .61 acre lot in a small neighborhood! Over the past 12 years, the seller performed substantial updates including a new metal roof, installed a new central air system with new ductwork, converted from oil to propane, added a high efficiency propane furnace and on-demand water heater, updated 200 AMP electrical, plus a new well pump and retention tank! You can add your personal touch throughout the interior and enjoy everything this Home has to offer! The main level offers a spacious eat-in kitchen with large pantry and access to the side deck, living room with HW floors and abundant natural light, bedroom with HW floors, super convenient full bath and separate 8'5" by 9'7" laundry room! Upstairs find three spacious bedrooms, including the primary with his and her closets, and a shared full bath! Other updates include newer windows (2005 - 2010), septic system (1989) and new Well (1985). The walkout portion of the lower level used to house a wood stove and was set up as a 350 ft.2 rec room, while the basement is great for storage. The yard has lots of possibilities and comes with 2 storage sheds! Centrally located minutes from shopping, restaurants, golf, parks, trails, and farms, while ECSU is 10 minutes away, and UConn Storrs is 15 minutes!

27 Gamache Ln, Windham
$290,000
3 Beds ⋅ 2 Baths ⋅ 24196295 MLS
Investment or owner-occupant opportunity in Killingly! Whether you are looking to expand your portfolio with instant cash flow or occupy one unit while letting the tenant help cover your mortgage, this well-maintained, character-filled, multi-family home provides the perfect footprint. Current first-floor tenant holds an active lease through February 2027. The second floor tenant in process of moving out. Detached 4-car garage adds to income potential, with 2 bays already rented.

19 Cady St, Killingly
$265,000
3 Beds ⋅ 1 Baths ⋅ 24194523 MLS
Check out this home with great potential! With a little vision and sweat equity this house could be transformed into the home of your dreams. The backyard is spacious, private, and ready for you to relax in. Subject to probate court approval.

39 Sterling Hill Rd, Plainfield
$250,000
2 Beds ⋅ 1 Baths ⋅ 24194151 MLS
Calling all investors, contractors, and ambitious renovators! Enjoy a rare opportunity just moments from beautiful Quaddick Lake with a seasonal water view, deeded right-of-way access to the lake, and close proximity to Quaddick State Park for boating, fishing, swimming, hiking, and year-round recreation. The property features a 2-bedroom, 1-bath main home and a detached 1-car garage with an upstairs accessory dwelling unit, offering additional flexibility and potential (buyer to perform due diligence regarding permitted uses). Inside, you'll find a nostalgic time capsule featuring warm wood cabinetry, vintage wallpaper, retro finishes, and a bright dining room surrounded by windows. Rich with character and ready for its next chapter, this property presents an exceptional opportunity to restore, renovate, or reimagine. Sold strictly as-is, the property requires significant renovation throughout and should be considered a substantial rehabilitation project.

16 Breaults Ln, Thompson
$299,900
24193379 MLS
Imagine building your dream home on more than 5 scenic acres and creating your own private residential helicopter estate. This unique property is home to Yankee Airstrip (CT13), an officially licensed Connecticut private airstrip, offering the opportunity for a future owner to pursue conversion to a private heliport, allowing you to build a custom home, construct a hangar, and enjoy the convenience of a helipad right in your own backyard. Perched at approximately 720 feet in elevation, the property features breathtaking views, spectacular sunrises, and the peace and privacy of Connecticut's beautiful countryside, while remaining just minutes from shopping, restaurants, three prestigious preparatory schools, and other local amenities. Whether you're a helicopter owner, aviation enthusiast, or someone looking for an extraordinary homesite with endless possibilities, this is a rare opportunity to create a one-of-a-kind residential aviation property. Design your dream home, build your hangar, and enjoy the convenience of flying directly from your own property. Partial owner financing may be considered. Schedule your private tour today and discover the possibilities. If you would rather just purchase and use this property as the existing air strip, please check out MLS listing 24156652 for more pictures and details. Come take a look-let's talk!

1450 North Rd, Killingly
$300,000
24188739 MLS
22.2-acre building lot offering endless possibilities in desirable Woodstock! Whether you're a builder, investor, or looking for the perfect location to build your forever home, this property is ready for your vision. Approximately 0.5 acres have already been cleared, and valuable due diligence has been completed, including a town-approved septic design, engineered site plan, and professionally delineated and marked wetlands. Neighboring lots have been surveyed, adding to the property's appeal. Enjoy the privacy and beauty of country living with plenty of space for your dream home while remaining conveniently located near local amenities and major routes. A rare opportunity to own a large parcel with much of the groundwork already in place. Bring your plans and make your dream a reality!

Route 197, Woodstock
$285,000
2 Beds ⋅ 2 Baths ⋅ 24187714 MLS ⋅ Putnam Riverview BLDG.
This townhouse offers both convenience and spaciousness. Located nicely to all shopping, parks, hospital and the highway. End unit with a one car garage. The fully applianced kitchen, and 1/2 bath. On the upper level are 2 large bedrooms and a full bath. Each bedroom has plenty of closet space. New gas/range/oven, microwave does not work AGENT RELATED TO SELLER

257 Sabin St Unit 21, Putnam
$299,900
6 Beds ⋅ 3 Baths ⋅ 24187426 MLS
Excellent opportunity to own a spacious 2-family home with great flexibility for investors or owner-occupants. The first unit offers 2 bedrooms and 1 full bath, while the second unit features a generous 4-bedroom, 2-bath layout, providing plenty of space for larger households or strong rental potential. A 2-car garage adds valuable parking and storage, making this property even more attractive. Whether you're looking to expand your investment portfolio, live in one unit and rent the other, or accommodate extended living arrangements, this multi-family home offers versatility, functionality, and long-term value. Sold as is where is. Needs work

14 Carey St, Windham
$275,000
3 Beds ⋅ 2 Baths ⋅ 24186792 MLS
Full of character, this 3-bedroom, 2 full bath home offers a spacious and functional layout in a convenient, walkable location. The main level features a large living room, a spacious kitchen with plenty of room to cook and gather, a dedicated dining room, a versatile bonus room perfect for a home office or playroom, and the convenience of first-floor laundry. All three bedrooms are located upstairs, offering separation from the main living spaces. Connected to city water and sewer and close to shops, restaurants, schools, and everyday amenities, this home is ready for its next chapter.

602 N Main St, Killingly
$299,900
24174800 MLS
On a private road surrounded by unspoiled natural beauty, this remarkable 79-acre property offers exceptional privacy and endless potential. Two brooks enhance the landscape - Lebanon Brook along the western boundary and Porter Pond Brook to the east. The land features a mix of wetlands and highlands, heavily wooded with abundant timber resources. Create your secluded homestead in the wilderness among other large-acreage parcels, with enough lumber to build and heat your home for years to come. The property includes approximately 300 feet of road frontage on Ide Perrin Road, 1,143 feet of frontage on Pole Bridge Road, and 416 feet of frontage by right-of-way. Please do not walk the property without your Realtor present.

00 Ide Perrin Rd, Woodstock
$285,000
3 Beds ⋅ 1 Baths ⋅ 24174794 MLS
Discover the potential in this fixer-upper featuring an ideal floor plan with spacious, flowing living areas and endless possibilities to make it your own. The open and functional layout offers great bones for a renovation project, with generously sized rooms, abundant natural light, and a seamless flow perfect for modern living and entertaining. Whether you're an investor, flipper, or buyer looking to create your dream home, this property is a fantastic opportunity to bring your vision to life while adding significant value. A rare chance to transform a home with incredible potential into something truly special! Property is subject to short sale.

37 Ruth St, Killingly
$275,000
2 Beds ⋅ 2 Baths ⋅ 24165775 MLS ⋅ Whetstone Mills BLDG.
Whether you are a first-time buyer, downsizing or looking for low maintenance living this condo is ideal. Escape to tranquility in this beautiful 2 bedroom 1230 sqft condo nestled in a serene forest surrounded setting. Inside the spacious living room welcomes you with a cozy fireplace ideal for chilly evenings. The primary bedroom is a true retreat featuring an elegant Palladian window that fills the space with ample natural light. The thoughtfully designed layout offers both functionality and charm. Enjoy the perfect blend of nature and comfort with peaceful wooded views. All newer carpet and freshly painted. Tile flooring in Kitchen and bath. Cute deck for plants and enjoying nature.Oversized 2 car garage gives you plenty of storage space. Close to RI line.

604 Whetstone Mls Unit 604, Killingly
$300,000
24163641 MLS
Experience the quintessential beauty of this New England countryside on this breathtaking 8.8 acres. This property offers a rare sense of pastoral peace without sacrificing convenience. Located less than a quarter-mile from I-395, you can enjoy a quiet, rural lifestyle with seamless transit to Boston, Providence, and NYC right at your doorstep. Buyer should do their own Due Diligence.

100 Hubbard Hill Rd, Killingly
$265,000
1 Baths ⋅ 24163683 MLS
TURNKEY AUTO SALES & SERVICE ON ROUTE 12 - 10,200 cars/day past the door, 60+ vehicle paved lot, 0.3 mi from I-395 Exit 28. Equipment conveys: 2 vehicle lifts, tire machine, air compressor, waste-oil tank & security system - operate day one, or seller removes it all at his expense for a clean shell. 1,496 SF reinforced-concrete building with finished concrete floors, overhead door, and 200 SF office. Flexible CI zoning supports 25+ uses: auto repair, used-car sales, tire/body shop, detailing, towing, contractor or fleet base, fabrication, equipment rental and more. ENVIRONMENTAL: Connecticut's Transfer Act sunset on 3/1/2026 - this sale requires NO Transfer Act filing and no certifying party (PA 25-6), a major change for auto-use properties. I-395 Enterprise Corridor location: Amazon last-mile and ULINE's 1.25M SF facility within 1 mile; the neighboring auto businesses stay consistently busy. Dealer-license roadmap (Town Certificate of Approval of Location + DMV K-7) available for serious buyers. Showings by appointment.

960 Norwich Rd, Plainfield
$299,900
24156652 MLS
Discover an extraordinary aviation opportunity in the heart of Connecticut's country side. This licensed private landing area known as Yankee Airstrip - CT 13 offers pilots and aviation enthusiasts a rare chance to own their piece of the sky. Positioned at a 720 ft. elevation, the property features a well-maintained 1700 ft. turf runway that's 90 ft. wide. The airfield fits perfectly in Dayville's rolling landscape, where morning mist dances across the landing field and afternoon flights offer breathtaking views of New England's changing seasons. Whether you're a seasoned pilot looking for a base of operations or an aviation dreamer ready to take flight, this property offers functionality wrapped in natural beauty.. The surrounding area provides convenient access to essential amenities. 3 Prep-Schools and shopping options within a reasonable distance. Hartford and Boston are an approximately 30 minute flight, with Providence even closer at less than 20 minutes. Don't miss out on this exciting opportunity. Schedule a showing today! Partial Owner Financing Considered. This property is also being marketed as a residential building lot with the possibility of converting the landing strip into a helipad , please look at MLS 24193379 Come take a tour and let's talk!

1450 North Rd, Killingly
$299,900
24142256 MLS
Discover the potential of this 1.07 acre lot. The property currently features a barn structure, but the true value lies in the land itself, being located on a private - no outlet road! With ample space to develop to dream property. Explore the possibilities this well-situated property has to offer. Trailer on property does not convey.

71 Deerfield Dr, Sterling
$275,000
7 Beds ⋅ 4 Baths ⋅ 24138836 MLS
Mixed-use investment property with multiple income streams and strong value-add potential. The property is zoned B-1A and currently configured with two occupied residential units generating income, plus two additional gutted residential units with plumbing in place, ready for build-out. The property also includes a commercial storefront with a separate entrance, offering flexibility for a variety of permitted uses. B-1A zoning may allow for additional residential units, subject to municipal approvals. Additional income opportunities include four dedicated storage spaces, ideal for ECSU students or nearby tenants, two garage bays, and an on-site parking lot, all of which convey with the property. Property is being sold as-is.

129 Valley St, Windham
$289,000
3 Beds ⋅ 1 Baths ⋅ 24133723 MLS
RANCH HOME! Bring your vision and make this 3-bedroom, 1-bath ranch your own! Situated on a corner lot, this 960 sq ft home offers great potential with a full basement for added space or storage. Enclosed porch. With some repairs and updates, this property could shine again-ideal for investors, DIY enthusiasts, or first-time buyers looking for a project. Features a dirt driveway and solid bones ready for your finishing touches.

47 Texas Heights Rd, Plainfield
$295,000
24074457 MLS
Level, lightly wooded commercial lot, next to retail plaza and Cumberland Farms. 2.79 acres. 535' road frontage. Zone VC Village Commercial. Both Well and Septic needed. $295,000. PERMITTED USES: Retail, Services, Office, Indoor Recreation, Motel... BY SPECIAL PERMIT: Church, School, Museum, Multi-use (mixed use)...

19 Knollwood Dr, Canterbury
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