Windham CT Real Estate

120 North Street Windham CT 06226

MLS Number 24204552

  • Multi Family Multi-Family For Sale
  • Square Feet 3,389
  • Acreage 0.26
  • Bedrooms 10
  • Bathroom 5

Income producing multi family property offering a strong opportunity for investors or owner occupants alike. One unit is currently not leased, providing immediate leasing potential or flexibility for owner occupancy. Property presents the opportunity to generate rental income with additional upside potential over time. Detached garage offers added utility with potential for storage, workshop space, or future supplemental income opportunities. Conveniently located near Eastern Connecticut State University, downtown Willimantic, shopping, dining, and major commuter routes. Great opportunity to add a multifamily asset to an investment portfolio. One of the parties to the LLC has an active real estate license.

Listed by Michelle Mandel of Carl Guild & Associates

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$/month over payments
Federal 30-year interest rate: 7.24% last updated on Oct 29, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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7 Scarborough Road Windham CT 06280

Windham, CT7 Scarborough Road

Price$499,900

Est. Mortgage: $/month

MLS Number 24210893

  • Single Family
  • Square Feet 1,664
  • Bedrooms 3
  • Bathroom 3
  • Year Built 2026

Beautiful new country home to be built on a picturesque 1.03-acre lot, offering the perfect blend of quality, comfort, and modern design. The thoughtfully designed open floor plan features solid wood flooring, vaulted ceilings in the living and dining rooms, and an abundance of natural light. The custom kitchen will showcase granite countertops and plenty of space for cooking and entertaining. Enjoy the convenience of 2 full baths plus a half bath, central air conditioning, and an attached 2-car garage. This is your opportunity to personalize and customize a brand-new home to fit your style and needs. Build the home you've been dreaming of in a peaceful country setting!

Listed by Cathyann M. Schulte of Countryside Realty

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$/month over payments
Federal 30-year interest rate: 7.24% last updated on Oct 29, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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33 Machine Shop Hill Road Windham CT 06266

MLS Number 24215433

  • Single Family
  • Square Feet 2,548
  • Bedrooms 4
  • Bathroom 4
  • Year Built 1850

Looking for a home with a little extra room to spread out? This beautifully renovated single-family home offers the perfect combination of modern updates, comfort, and flexibility! One of its standout features is the additional first-floor living space, offering added privacy and versatility for a variety of lifestyle needs. This separate area features comfortable finished living space, a full bathroom, and its own laundry area, providing convenience and functionality. The bright, open-concept kitchen, dining, and living areas create a welcoming atmosphere perfect for everyday living and entertaining. A dedicated home office provides additional flexibility, while convenient main-level laundry adds even more functionality. Extensively remodeled throughout, this move-in-ready home showcases beautiful modern updates, including a new roof and new furnace, offering added value and peace of mind. Step outside to enjoy the spacious deck, perfect for relaxing or entertaining. The property also features two detached garages, including an oversized heated garage, offering exceptional space for vehicles, storage, a workshop, or hobbies. With its beautifully updated interior, flexible floor plan, additional first-floor living space, and impressive garage accommodations, this property offers more than meets the eye! Enjoy the comfort of single-family living with a little extra space to make your own. Schedule your private showing today!

Listed by Michele Geragotelis of RE/MAX Bell Park Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.24% last updated on Oct 29, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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28 Pleasant Street Windham CT 06226

MLS Number 24204645

  • Multi Family Multi-Family For Sale
  • Square Feet 2,674
  • Acreage 0.53
  • Bedrooms 5
  • Bathroom 3

3 Family well maintained for sale in Willimantic with extra large lot size, .53 ac. and extra large out building for garage, storage and workbench area with power. 2 units on first floor with one unit on second floor. close and convenient to Main Street and bus line. Historical home been in family for generations. see agent remarks

Listed by Kathy Dubay of I.M.A. Realty LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 7.24% last updated on Oct 29, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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260 Summit Street Windham CT 06226

MLS Number 24185574

  • Multi Family Multi-Family For Sale
  • Square Feet 2,939
  • Acreage 0.13
  • Bedrooms 9
  • Bathroom 4

Opportunity awaits with this multi-family property in Willimantic. Featuring multiple residential units with a mix of layouts, this property offers flexibility for both investors and owner-occupants seeking rental income. Conveniently located near Eastern Connecticut State University, shopping, restaurants, parks, public transportation, and major commuter routes. Separate living spaces provide privacy for occupants while the property's central location adds to its long-term appeal. Whether you're looking to expand your investment portfolio or offset your housing costs with rental income, this property presents a versatile opportunity in a convenient location. One of the parties to the LLC has an active real estate license.

Listed by Michelle Mandel of Carl Guild & Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 7.24% last updated on Oct 29, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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45 Whittemore Street Windham CT 06226

Windham, CT45 Whittemore Street

Price$374,900

Est. Mortgage: $/month

MLS Number 24184708

  • Single Family
  • Square Feet 1,718
  • Bedrooms 3
  • Bathroom 2
  • Year Built 1967

Welcome home to this lovingly maintained 3-bedroom, 2-bath Ranch set on nearly half an acre in Willimantic. A welcoming slate-tiled foyer leads into a spacious living room that flows seamlessly into the dining area, creating a bright and inviting space filled with natural light. The eat-in kitchen features warm wood cabinetry, granite countertops, and ample workspace for meal preparation. Step outside to the composite deck overlooking the fenced backyard, perfect for relaxing, entertaining, gardening, or play. The home offers a primary suite with a private bath and two additional bedrooms. Laundry is currently located in the third bedroom but can easily be relocated to the basement, where washer and dryer hookups already exist. The walkout lower level is unfinished and offers endless possibilities for future expansion, including additional living space, a home office, gym, or potential in-law setup. Additional features include a spacious two-car garage with storage, central air, a boiler and heat pumps for efficient heating and cooling. Move right in and make it your own!

Listed by Nadia Kachwaha of KW Legacy Partners

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$
%
$/month over payments
Federal 30-year interest rate: 7.24% last updated on Oct 29, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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33 Old Brooklyn Turnpike Windham CT 06280

Windham, CT33 Old Brooklyn Turnpike

Price$359,000

Est. Mortgage: $/month

MLS Number 24215945

  • Single Family
  • Square Feet 1,701
  • Bedrooms 3
  • Bathroom 3
  • Year Built 1947

Country living at its best with this Contemporary Cape w/1711sqft, 3 Bedrm, 3 Full Baths, HUGE 1000 plus sqft BARN/GARAGE/OUTBUILDING ON 2.64 ac of level land with a stream. Perfect property for hobbys, animals, storage, wood working, home based business and much more. Open floor plan w/ 2 Foyer entrances w/ tiles floors, open kitchen & dining rm with slider to your private deck. Living rm with a woodstove. 1st floor large bedrm w/ full bath with tile floor & adorable barn doors. 2nd floor has a Master suite w/ Full bath w/a jacuzzi tub. 2nd master bed w/vaulted ceilings & french doors to a private deck. Separate office, play rm or could be a large walkin closet & a 3rd FULL BATH. BARN/OUT BUILDING/ GARAGE w/ a full attic floored. So many possibilities in this home. Bring your horses, home based business, 4 wheelers, dirt bike, green house, storage, man cave, garage, chicken coop & so much MORE. Sits privately off the road with lots of space for gardens on a nice level lot. Many updates throughout the years including windows, roof, septic tank, well tank & much more. Solar panels to save money on power. Power bill is approx 80 dollars a month. Sits on a dead end street. Come live in the country close to all major routes, airport, Hartford, cssinos for ONLY 365,000

Listed by Irene Adams of Signature Properties of N.E.

$
$
%
$/month over payments
Federal 30-year interest rate: 7.24% last updated on Oct 29, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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19 Bellevue Street Windham CT 06226

MLS Number 24210038

  • Multi Family Multi-Family For Sale
  • Square Feet 2,678
  • Acreage 0.14
  • Bedrooms 5
  • Bathroom 2

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.

Listed by Kris J. Lippi of Get Listed Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.24% last updated on Oct 29, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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207 Summit Street Windham CT 06226

MLS Number 24216414

  • Single Family
  • Square Feet 2,318
  • Bedrooms 3
  • Bathroom 2
  • Year Built 1892

Step into a truly one-of-a-kind home where history, character, and creativity come together. Originally built circa 1892 as the historic Hilltop Hose Company No. 3 Firehouse, this remarkable property has been thoughtfully transformed into an eclectic single-family residence while honoring its architectural roots. The 1,000-square-foot first floor offers an expansive open layout with soaring ceilings, creating an impressive space for everyday living and entertaining. Nearly as spacious, the versatile third-floor retreat includes a full bathroom, extensive built-in storage, counter space, and a private balcony-making it ideal as a generous primary suite, guest room, living area, home office, creative studio, or flexible multigenerational living space. Distinctive Art Deco-inspired design elements add personality throughout, creating a home unlike any other. The composite and stone patio, landscaped yard, and the refreshing shade of mature trees make it an ideal spot to enjoy your morning coffee or unwind at the end of the day. The impressive stone foundation basement boasts high ceilings, a laundry area with utility sink, and clean storage space. Conveniently located near Eastern Connecticut State University, downtown Willimantic's restaurants, shops, entertainment, and local events, with easy access to Route 6 and a short drive to UConn. A rare opportunity to own a distinctive property where historic charm and modern comfort blend into an unforgettable place to call home.

Listed by Sue Esposito of Home Selling Team

$
$
%
$/month over payments
Federal 30-year interest rate: 7.24% last updated on Oct 29, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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15 Cracow Avenue Windham CT 06280

Windham, CT15 Cracow Avenue

Price$324,999

Est. Mortgage: $/month

MLS Number 24214512

  • Single Family
  • Square Feet 1,228
  • Bedrooms 3
  • Bathroom 2
  • Year Built 1972

Imagine summer mornings with coffee on the new Trex deck, afternoons spent by your in-ground pool, and evenings launching a kayak right into the river behind your backyard. At 15 Cracow Ave, that lifestyle comes together with the comfort of an updated 3-bedroom, 2-bath ranch where many of the big-ticket improvements have already been taken care of. Inside, the open floor plan was made for gathering. The remodeled kitchen features quartz countertops and soft-close cabinetry and opens directly into the dining area and spacious living room, where a wood-burning fireplace becomes the centerpiece on cooler New England nights. Down the hall, the true primary suite gives you something rarely found at this price point-a private full bathroom with double vanities-along with two additional bedrooms and a second full bath.

Listed by AJ Davis of Better Homes and Gardens Real Estate Executive Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 7.24% last updated on Oct 29, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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125 Mountain Street Windham CT 06226
Coming Soon

MLS Number 24157885

  • Single Family
  • Square Feet 2,781
  • Bedrooms 5
  • Bathroom 2
  • Year Built 1900

Discover the possibilities with this spacious two-family property! Whether you're looking to owner-occupy one unit while utilizing the second or exploring the potential of renting both, this property offers flexibility to suit your needs. Both living spaces feature comfortable areas for relaxing and entertaining, while the kitchens provide ample cabinet and counter space for everyday convenience. Enjoy the generous yard, offering plenty of room for outdoor activities and gatherings. The property may also offer potential for future subdivision or additional development, subject to town approval and buyer due diligence. Don't miss the opportunity to explore all this property has to offer!

Listed by Lisa Antrum of KW Legacy Partners

$
$
%
$/month over payments
Federal 30-year interest rate: 7.24% last updated on Oct 29, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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14 Carey Street Windham CT 06226

Windham, CT14 Carey Street

Price$299,900

Est. Mortgage: $/month

MLS Number 24187426

  • Multi Family Multi-Family For Sale
  • Square Feet 2,700
  • Acreage 0.27
  • Bedrooms 6
  • Bathroom 3

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

Listed by Amy P. Rio of Better Homes and Gardens Real Estate Executive Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 7.24% last updated on Oct 29, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

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