Windham CT Real Estate

254 Beaver Hill Road Windham CT 06256

MLS Number 24174325

  • Single Family
  • Square Feet 1,808
  • Bedrooms 3
  • Bathroom 2
  • Year Built 2004

Hidden Acres is a rare opportunity to own 70+ secluded acres where rustic charm, craftsmanship, and modern functionality come together. Tucked away in a private setting, this extraordinary farm features a 14,400-square-foot equestrian facility with a 12-stall barn and indoor riding arena, ideal for horse enthusiasts, trainers, or those seeking a premier recreational property. A heated 1,920-square-foot garage with three-phase power offers exceptional versatility for workshops, equipment storage, or business operations. The thoughtfully crafted custom-built 1,808-square-foot, three-bedroom home blends comfort with rustic character, featuring stunning trim details and rich oak hardwood floors milled from timber harvested directly from the land. Completing this one-of-a-kind retreat is a dock-diving pool for dogs, adding a fun and unique amenity for pet lovers. Hidden Acres is a truly special property where rustic living, privacy, and purpose unite.

Listed by Lori A. Vogel of William Raveis Real Estate

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$/month over payments
Federal 30-year interest rate: 6.53% last updated on May 28, 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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253 Brick Top Road Windham CT 06280

MLS Number 24140956

  • Land
  • Acreage 56.4
  • MLS Status Active
  • Other Amenities Golf, Waterfront
  • Zoning R2

64+/- acres on Route 14, the largest parcel available in Willimantic with access to public water and sewer. Three parcels sell together, 253 Brick Top 56.40 acres, 303R Brick Top 5.75 acres, 267 Brick Top 1.64 acres. Allowed uses: schools, museums, clubs, daycare, nursing homes, camping areas, private clubs and recreational facilities, commercial kennels, boarding facilities Several existing structures in varying condition, value is in the land

Listed by David Mieczynski of National Realty Advisors LLC

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$/month over payments
Federal 30-year interest rate: 6.53% last updated on May 28, 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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120 North Street Windham CT 06226

MLS Number 24177946

  • 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.

Listed by Michelle Mandel of Carl Guild & Associates

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$/month over payments
Federal 30-year interest rate: 6.53% last updated on May 28, 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 Sycamore Terrace Windham CT 06280

Windham, CT7 Sycamore Terrace

Price$449,000

Est. Mortgage: $/month

MLS Number 24176079

  • Single Family
  • Square Feet 2,816
  • Co List Office Name eXp Realty
  • Bedrooms 5
  • Bathroom 3

Welcome Home to this beautifully updated 5-bedroom Colonial tucked away on a dead end road on a private, wooded .78-acre lot. Step inside to a sun-filled living room where the fireplace sets the tone for cozy New England evenings, flowing seamlessly into the formal dining room and updated kitchen - ideal for hosting holidays or casual weeknight meals. Just off the main level, the bright 3-season room with slider access serves as a true extension of the living space, overlooking the backyard. A main-level office or fifth bedroom adds everyday flexibility. Upstairs offers four generously sized bedrooms and a full bath, while the finished, heated walk-out lower level with full bath and laundry provides even more room to work, play, or unwind. Just a short distance to Shetucket Plains Road Park & Route 32.

Listed by John Michael Varrone and Terry Varrone of eXp Realty

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$/month over payments
Federal 30-year interest rate: 6.53% last updated on May 28, 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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99 Bellevue Street Windham CT 06226

MLS Number 24178511

  • Single Family
  • Square Feet 2,166
  • Bedrooms 5
  • Bathroom 2
  • Year Built 1932

Wonderful opportunity to own this charming Craftsman-style home in the desirable Hill Section of Willimantic. Built circa 1932, this well-maintained home is filled with timeless character and original details including beautiful natural woodwork, lovely wood doors, glass door knobs, built-ins, and classic architectural charm throughout. The remodeled kitchen features beautiful cabinetry, granite countertops, and ample workspace, blending modern convenience with the home's original warmth and character. Recently renovated full bathrooms on both the first and second floors offer added comfort and functionality. The flexible floor plan includes a bright sunroom/home office on the main level, ideal for remote work, hobbies, or additional living space. Most of the home features energy-efficient replacement windows. The second floor includes a partially finished walk-in storage room with excellent potential for future expansion into additional living area, studio space, or a bonus room. A large full basement and detached storage shed provide abundant storage options. Additional features include a 2-car under garage and established setting conveniently located close to Eastern Connecticut State University, downtown dining, shopping, and entertainment, with easy access to Route 6 and just minutes to University of Connecticut. A rare opportunity to own a home full of charm, character, and future potential.

Listed by Sue Esposito of Home Selling Team

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$/month over payments
Federal 30-year interest rate: 6.53% last updated on May 28, 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 24158358

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

Investors take notice! This home is a money maker. Whether you decide to owner-occupy this spacious home while rental income helps with the mortgage, or rent out both units, you can't go wrong. The living areas provide warm spaces perfect for relaxing or gathering with friends and family. The kitchens offer ample cabinet and counter space, making everyday cooking convenient and enjoyable. The large yard space can be enjoyed year round. The lot may also have the potential to be subdivided to add another home. All information should be verified with the town. Don't miss this opportunity!

Listed by Lisa Antrum of KW Legacy Partners

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$/month over payments
Federal 30-year interest rate: 6.53% last updated on May 28, 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. Current NOI is approximately $38,291, with substantial upside through completion of the two remaining residential units. Property is being sold as-is. Rent roll and financials available upon request.

Listed by Kyle West of eXp Realty

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$
%
$/month over payments
Federal 30-year interest rate: 6.53% last updated on May 28, 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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43 Hilltop Drive Windham CT 06256
Open House

MLS Number 24178737

  • Single Family
  • Next Open House: Sat 06/6 10:30 am. to 12:30 pm.
  • Square Feet 1,820
  • Bedrooms 3
  • Bathroom 2

This charming 3bedroom home blends fresh updates with future possibilities. The remodeled kitchen and new flooring (main level) create a bright, modern feel from the moment you walk in. Enjoy morning coffee on the deck, easy parking with the attached garage, and the freedom to design the lower level into whatever space you've been dreaming of. A home that fits your life today-and tomorrow. There is a powder room on the main floor and a full bath (tub/shower combo) on the upper floor. Furnace was replaced in 2022. Perfect location in the Oak Forest Village; convenient to UCONN, ECSU, Windham Hospital, Golf Courses, Shopping and Airline North State Park Trail. Charles H. Barrows STEM Academy is just down the road.

Listed by Joan M. Casey of RE/MAX Legends

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$
%
$/month over payments
Federal 30-year interest rate: 6.53% last updated on May 28, 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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1 Gem Drive Windham CT 06226

Windham, CT1 Gem Drive

Price$289,000

Est. Mortgage: $/month

MLS Number 24171983

  • Single Family
  • Square Feet 912
  • Co List Office Name Home Selling Team
  • Bedrooms 3
  • Bathroom 2

Welcome to 1 Gem Drive. This well cared for 3-bedroom, 2-bath raised ranch offers comfort, charm, and space to enjoy both inside and out. The home features additional finished space in the lower level, perfect for a family room, home office, or guest area, complete with a full bath. Step into a bright and inviting layout designed for easy living, with plenty of room for both relaxing and entertaining. Start your mornings on the peaceful screened-in porch-the perfect spot for coffee and quiet moments. In the afternoons, head out to the large fenced-in yard, where beautifully flowering trees create a picturesque setting ideal for gatherings, gardening, or simply unwinding. With its thoughtful upkeep and inviting indoor and outdoor spaces, this home is ready to welcome its next owner. Don't miss the opportunity to make it yours.

Listed by Stephen Galinat and John F. Fulton of Home Selling Team

$
$
%
$/month over payments
Federal 30-year interest rate: 6.53% last updated on May 28, 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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66 Gifford Avenue Windham CT 06226

Windham, CT66 Gifford Avenue

Price$269,000

Est. Mortgage: $/month

MLS Number 24175215

  • Single Family
  • Square Feet 1,010
  • Bedrooms 2
  • Bathroom 1
  • Year Built 1952

There's something special about a home that instantly feels warm and welcoming, and this charming 2 bedroom ranch in Windham does exactly that. From the moment you walk inside, sunlight pours through the living room, reflecting beautifully off the hardwood floors and creating a space that simply feels like home. The open layout makes everyday living easy, with a cozy dining area that flows naturally into the eat-in kitchen featuring stainless steel appliances, abundant cabinetry, and plenty of room to cook, gather, and make memories. Both bedrooms offer hardwood flooring, ceiling fans, and generous closet space, creating comfortable retreats at the end of the day. Downstairs, the unfinished basement is ready for your imagination whether you envision a home gym, workshop, recreation room, or additional living space. Outside is where this home truly shines. Relax beneath the covered patio with your morning coffee, listen to the sounds of nature, and enjoy the privacy of the peaceful backyard with various fruit trees. Thoughtfully updated with new kitchen appliances, kitchen flooring, fresh paint, professionally cleaned vents, a new furnace motor, and new water heater, this home offers both comfort and peace of mind. Whether you're just starting out, downsizing, or looking for a place to truly make your own, this inviting ranch is ready to welcome its next chapter.

Listed by Tina Frigeri of KW Legacy Partners

$
$
%
$/month over payments
Federal 30-year interest rate: 6.53% last updated on May 28, 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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119 Quercus Avenue Windham CT 06226

Windham, CT119 Quercus Avenue

Price$250,000

Est. Mortgage: $/month

MLS Number 24152527

  • Single Family
  • Square Feet 1,160
  • Bedrooms 3
  • Bathroom 2
  • Year Built 1890

Tucked into The Oaks, one of Willimantic's most beloved neighborhoods, this 1890s Cape Cod is a home that feels instantly welcoming. Built by the Willimantic Linen Company, it reflects a simpler time, beginning with a covered front porch and a thoughtfully scaled interior that feels comfortable and inviting. The 1,160 square foot home offers three bedrooms and a cozy living room featuring the home's original central fireplace, a natural gathering spot on cooler New England days. Hardwood flooring runs through much of the home, while select areas feature original wide plank floors secured with square nails, authentic details that add warmth and character. Out back, a deck overlooks a sweet, manageable yard that is easy to enjoy and easy to care for. A detached one car garage and an additional shed provide practical storage. Set along tree lined streets surrounded by charming Victorian style cottages, this home offers a wonderful opportunity to settle into a neighborhood with real history and a strong sense of peace. Property to be sold in as-is condition.

Listed by Kristen Kaskela of Berkshire Hathaway NE Prop.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.53% last updated on May 28, 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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26 Plains Road Windham CT 06280

MLS Number 24164604

  • Single Family
  • Square Feet 2,758
  • Bedrooms 4
  • Bathroom 2
  • Year Built 1732

*** Dutch Colonial Style Home Brimming with History and Potential *** This home is the former parsonage for St. Paul's Episcopal Church, with many antique features reminiscent of its time - gambrel style roof, colonial American style woodwork, wide plank floors, field stone foundation and walk ways, and accretive architecture. The home is sprawling with over 2700 Sqft, 4 bedrooms, 1 1/2 baths, large mud/laundry room, spacious eat-in kitchen, and large, lower level workshop area with natural lighting. It is steps away from historic Windham Center and Town Green, and is surrounded by other beautiful antiques homes. Per town record New gas line (2020), new stainless steel chimney liner (2020), new oil hot air furnace (2019), and oil tank (2015). Cash, conventional or rehab loans only. Home is in a historic district, rules and regulations can be found at the Town of Windham website. ***This is an estate sale, subject to probate court approval. Buyer to do due-diligence. Being sold in AS-IS/WHERE-IS including personal property ***

Listed by Christy L. Lofstrom of ERA Blanchard & Rossetto

$
$
%
$/month over payments
Federal 30-year interest rate: 6.53% last updated on May 28, 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.