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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$
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$/month over payments
Federal 30-year interest rate: 7.18% last updated on Nov 5, 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: 7.18% last updated on Nov 5, 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: 7.18% last updated on Nov 5, 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: 7.18% last updated on Nov 5, 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

MLS Number 24157885

  • Multi Family Multi-Family For Sale
  • Square Feet 2,781
  • Acreage 0.76
  • Bedrooms 5
  • Bathroom 3

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: 7.18% last updated on Nov 5, 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: 7.18% last updated on Nov 5, 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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Nov 5, 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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Nov 5, 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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55 Main Street Windham CT 06266

MLS Number 24216737

  • Multi Family Multi-Family For Sale
  • Square Feet 1,386
  • Acreage 0.09
  • Bedrooms 4
  • Bathroom 2

Investors Take Notice! Bring your vision and unlock the potential of this Victorian-style two-family property at 55 Main Street in Willimantic. Each unit offers 2 bedrooms and 1 bath, with both bathrooms recently updated with brand-new finishes. While the property would benefit from additional updating and improvements, the opportunity to build equity and maximize its potential is well worth exploring. Ideally located across from Recreation Park, near Eastern Connecticut State University and UConn, and within walking distance to local amenities and the bus line. Whether you're an investor seeking your next project or an owner-occupant looking to offset your mortgage with rental income, this property offers exciting possibilities. Bring your ideas, envision the possibilities, and schedule your showing today!

Listed by Annmarie A. Fortier of Coldwell Banker Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Nov 5, 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: 7.18% last updated on Nov 5, 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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270 South Windham Road Windham CT 06226

Windham, CT270 South Windham Road

Price$115,000

Est. Mortgage: $/month

MLS Number 24219114

  • Condo
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 765
  • Year Built 1968

Welcome to Cedar Crest in South Windham! This second-floor end-unit condo features two bedrooms, one full bath, a separate living room, and an eat-in kitchen with room for a dining table. In-unit laundry and two assigned off-street parking spaces add everyday convenience. Located just off Route 32, the condo offers easy access to downtown Willimantic, Eastern Connecticut State University, and UConn's Storrs campus.

Listed by John Brewer and Patrick Garrett of Exceptional Real Estate LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Nov 5, 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 Cloran Street Windham CT 06226

Windham, CT28 Cloran Street

Price$8,500

Est. Mortgage: $/month

MLS Number 24217749

  • Land
  • Acreage 0.17
  • MLS Status Active
  • Other Amenities Waterfront
  • Zoning R2

.17 Acre residential corner lot located in Windham! Conveniently located on the corner of Cloran and Alice St, with dual road frontage measuring over 95 ft total. Close to local highways and amenities. Buyer to perform all due diligence regarding zoning, utilities, and buildability

Listed by Maria Convertito of Regency Real Estate,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Nov 5, 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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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.