Windham CT Real Estate

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

MLS Number 24210578

• Single Family
• Square Feet 1,032
• Co List Office Name Rivera Realty LLC
• Bedrooms 3
• Bathroom 1

Welcome to this well-cared-for home, where thoughtful updates and a comfortable layout create an inviting place to call home. The spacious eat-in kitchen provides plenty of room for meals and entertaining and flows naturally into the living area. The home offers three bedrooms and a well-maintained bathroom. A full walkout basement provides excellent potential space, whether you need a recreation room, home office or workshop. Outside, you'll find a private deck, paved driveway, an a carport for convenient parking and outdoor enjoyment. The roof was newly installed in September 2026, providing an important recent improvement for the next owner. With its comfortable floor plan, outdoor amenities, and opportunity to expand, this home offers plenty of room to make it your own. Situated in a peaceful and desirable part of town, the property is also conveniently located near UConn and Eastern Connecticut State University.

Listed by Chely Rivera and Gabriela Rivera of Rivera Realty LLC

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

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

MLS Number 24159602

• Single Family
• Square Feet 1,078
• Bedrooms 4
• Bathroom 1
• Year Built 1915

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.

Listed by Lisa M. Therecka of Therecka & Associates LLC

MLS Number 24197730

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

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. 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

MLS Number 24208017

• Single Family
• Square Feet 1,152
• Bedrooms 3
• Bathroom 2
• Year Built 1910

Welcome to 38 Wilson Street in Willimantic, offering a spacious 7-bedroom, 2-bathroom layout on approximately 0.17 acres. Built in 1910, this property provides ample room for comfortable living, guests, or flexible use. The home's established character and convenient, easy access to local shopping, dining, schools, parks, and everyday amenities. A versatile opportunity for buyers seeking generous bedroom space and a property with potential.

Listed by Thomas Mele of Social & Co Realty

MLS Number 24205506

• Single Family
• Square Feet 1,000
• Bedrooms 2
• Bathroom 1
• Year Built 1952

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!

Listed by Thomas Mele of Social & Co Realty

MLS Number 24201064

• Single Family
• Square Feet 1,807
• Bedrooms 4
• Bathroom 2
• Year Built 1880

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.

Listed by Michelle Mandel of Carl Guild & Associates

MLS Number 24171622

• Single Family
• Square Feet 1,152
• Bedrooms 3
• Bathroom 2
• Year Built 2001

*** Highest and Best due 12pm Monday 8/10/2026 Completely remodeled 3-bedroom, 2-bath mobile home in North Windham! This move-in-ready home has been thoughtfully updated throughout and features a brand-new roof, new appliances, and modern finishes from top to bottom. The interior offers a bright and functional layout with updated flooring, refreshed kitchen and bathrooms, and comfortable living space. With recent upgrades throughout, this home provides a great opportunity for affordable, low-maintenance living. Conveniently located close to shopping, restaurants, and local amenities.

Listed by Arielle Ruffin of Choice Realty