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: 7.4% last updated on Oct 15, 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

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$/month over payments
Federal 30-year interest rate: 7.4% last updated on Oct 15, 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: 7.4% last updated on Oct 15, 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

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$/month over payments
Federal 30-year interest rate: 7.4% last updated on Oct 15, 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

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$
%
$/month over payments
Federal 30-year interest rate: 7.4% last updated on Oct 15, 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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505 Summit Street Extension Windham CT 06226
Coming Soon

Listing Number X95118858

  • Exclusive Residential
  • Sale or Lease for sale

Coming Soon!  Beautiful Bungalow full of charm and tons of updates. Walking distance to ECSU. Roof 2024, Boiler 2026, Newer Bathroom and Kitchen, New vinyl siding 2026. Newer windows and blown in insulation about 10 years ago. This is a must see for Owner occupants and investors. Town has as a 4 bedroom which is possible in the layout. Three bedrooms upstairs and one on first floor.

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$
%
$/month over payments
Federal 30-year interest rate: 7.4% last updated on Oct 15, 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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86 Chestnut Street Windham CT 06226

MLS Number 24201649

  • Multi Family Multi-Family For Sale
  • Square Feet 1,560
  • Acreage 0.16
  • Bedrooms 4
  • Bathroom 2

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.

Listed by Marcus Hamilton of CENTURY 21 Shutters & Sails

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$/month over payments
Federal 30-year interest rate: 7.4% last updated on Oct 15, 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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129 Valley Street Windham CT 06226

MLS Number 24138836

  • Multi Family Multi-Family For Sale
  • Square Feet 3,963
  • Acreage 0.25
  • Bedrooms 7
  • Bathroom 4

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.

Listed by Kyle West of eXp Realty

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$/month over payments
Federal 30-year interest rate: 7.4% last updated on Oct 15, 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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220 Plains Road Windham CT 06280

MLS Number 24180936

  • Land
  • Acreage 25.7
  • MLS Status Active
  • Other Amenities Waterfront
  • Zoning R3

Wonderful potential development opportunity. Road frontage on 2 roads, approximately 1350' of frontage on Plains Rd., and approximately 450' of frontage on Anna Maria Ln., and existing cul-du-sac subdivision. Possible 7-8 lots subdivision to be created.

Listed by Rick Nassiff of KW Legacy Partners

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$
%
$/month over payments
Federal 30-year interest rate: 7.4% last updated on Oct 15, 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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29 Kathleen Drive Windham CT 06226

Windham, CT29 Kathleen Drive

Price$199,900

Est. Mortgage: $/month

MLS Number 24197730

  • Condo
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,492
  • Year Built 1987

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.

Listed by Steph Rush of RE/MAX Legends

$
$
%
$/month over payments
Federal 30-year interest rate: 7.4% last updated on Oct 15, 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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760 Main Street Windham CT 06226

Windham, CT760 Main Street

Price$157,900

Est. Mortgage: $/month

MLS Number 24172978

  • Land
  • Acreage 0.17
  • Co List Office Name Lyman Real Estate
  • MLS Status Active
  • Other Amenities Waterfront

Highly visible main street location in the middle of Willimantic's dining, retail, historic district, and municipal office area. Public water, sewer & gas, 57 ft road frontage, 12,500 traffic count with .17 of an acre in the B1 zone.

Listed by Maxwell Lyman and Ron Lyman of Lyman Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 7.4% last updated on Oct 15, 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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90 Serwan Avenue Windham CT 06226

Windham, CT90 Serwan Avenue

Price$49,000

Est. Mortgage: $/month

MLS Number 24160418

  • Land
  • Acreage 0.29
  • MLS Status Active
  • Other Amenities Waterfront
  • Zoning R4

This nice residential lot sits on the edge of Mansfield and Windham. This property offers an opportunity to secure residential land in an established neighborhood with essential utilities accessible. Zoning: R-4 (Residential) Utilities: Public water and public sewer are available in the street; electricity and cable are also accessible at the site. Taxes are $109 (2025). Situated in a residential setting, this lot is within walking distance to ECSU and just minutes from the vibrant amenities of downtown Willimantic as well as ja 15 minute drive to UConn. Mansfield Hollow State Park and major retailers are short distances away with easy access to major commuting routes including Storrs Road, Route 6, 32, and 66. Agent and Owner related.

Listed by Sharon L. Stokland of List N Show LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 7.4% last updated on Oct 15, 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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