Windham CT Real Estate

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

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

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

MLS Number 24201525

• Single Family
• Square Feet 1,336
• Bedrooms 3
• Bathroom 1
• Year Built 1951

A delightful gem of a home, this Cape is set in the heart of Willimantic. This home offers easy access to town, shopping, and commuting routes. A charming, move-in-ready opportunity is updated and ready for its next owner, with an open-air plan and unique, tasteful finishing touches throughout. Fresh, modern updates within the last 4 years include: kitchen with granite counters and new stainless appliances (oven/range, microwave, range hood, refrigerator, dishwasher), first-floor bath, carpet in the upstairs bedrooms, newer vinyl siding, windows, roof, and furnace, 3-zone heat for comfort and efficiency. First-floor primary bedroom - easy single-level living, first-floor laundry in the expansive four-season sunroom, sunroom opens to a deck overlooking a very private backyard with stone walls, 3 bedrooms, 1 full bath, 6 rooms total, original wood panel interior doors; updated insulated exterior doors. Added features include, connected Bluetooth speaker in the shower, electric fireplace insert and, under-house 1-car garage plus private driveway (4 parking spaces) and Solar - schedule your tour today!

Listed by Paul Cutler of Keller Williams Realty Gr.Worc

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

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 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 24215087

• Single Family
• Square Feet 1,420
• Bedrooms 2
• Bathroom 1
• Year Built 1960

Adorable ranch/split level home! Convenient yet quiet non through road. Walk to the bus lines and shopping. Cute 2 bedroom home with updated bath, living room with fireplace. LVP and tile flooring throughout.Three outbuildings, side porch, and front patio. Heated lower level needs updating but great for expansion. Attached garage and walkout basement. Newer septic tank.Great backyard, paved driveway, set up a showing today.

Listed by Rick J. Loranger of Coldwell Banker Realty

MLS Number 24213182

• 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 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. One of the parties to the LLC has an active real estate license.

Listed by Michelle Mandel of Carl Guild & Associates