Windham CT Real Estate

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18 Hilltop Drive Windham CT 06256

MLS Number 24202946

  • Condo
  • Bedrooms 5
  • Bathroom 3
  • Square Feet 1,758
  • Year Built 1998

Welcome to desirable Oak Forest Village. This move-in-ready home offers one of the most spacious floor plans in the complex, with 3 bedrooms on the main floor and 2 on the lower level for ample room to spread out. With two and a half baths, enjoy the privacy of a primary bedroom with an en suite full bath. The open-concept living space features a remodeled kitchen with modern two-tone cabinets, stainless steel appliances, granite countertops and a breakfast bar, along with a designated dining area and a spacious living room with a vaulted ceiling. Perfect for both quiet nights in and holiday hosting. The hardwood floors were just refinished in preparation for the sale, and the half bath in the finished lower level was recently remodeled as well. A 2-car garage with automatic openers offers easy access and additional storage, while the deck and backyard provide space for gatherings, gardening, and outdoor relaxation. You're conveniently close to many amenities, including shopping, dining, golf, ECSU plus the Charles H. Barrows STEM Academy right on Tuckie Rd, and walking trails right behind the neighborhood. All ready and waiting for you!

Listed by Anne Newmyer of Simply Sold Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Aug 27, 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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18 Hilltop Drive Windham CT 06256

MLS Number 24202822

  • Single Family
  • Square Feet 1,758
  • Bedrooms 5
  • Bathroom 3
  • Year Built 1998

Welcome to desirable Oak Forest Village. This move-in-ready home offers one of the most spacious floor plans in the complex, with 3 bedrooms on the main floor and 2 on the lower level for ample room to spread out. With two and a half baths, enjoy the privacy of a primary bedroom with an en suite full bath. The open-concept living space features a remodeled kitchen with modern two-tone cabinets, stainless steel appliances, granite countertops and a breakfast bar, along with a designated dining area and a spacious living room with a vaulted ceiling. Perfect for both quiet nights in and holiday hosting. The hardwood floors were just refinished in preparation for the sale, and the half bath in the finished lower level was recently remodeled as well. A 2-car garage with automatic openers offers easy access and additional storage, while the deck and backyard provide space for gatherings, gardening, and outdoor relaxation. You're conveniently close to many amenities, including shopping, dining, golf, ECSU plus the Charles H. Barrows STEM Academy right on Tuckie Rd, and walking trails right behind the neighborhood. All ready and waiting for you!

Listed by Anne Newmyer of Simply Sold Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Aug 27, 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: 6.66% last updated on Aug 27, 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: 6.66% last updated on Aug 27, 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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41 Ashland Street Windham CT 06226
Coming Soon

MLS Number 24202429

  • Single Family
  • Square Feet 1,715
  • Bedrooms 4
  • Bathroom 2
  • Year Built 1915

Rare find kind of property! This property is complete with many incredible features. First Cape style home is 4 beds and 1.5 baths. Carpeted living room, first floor bedroom with a secondary bedroom that is currently being used as laundry room. Two additional rooms upstairs. Updated Galley style kitchen with granite countertops and plenty of cabinet space. Smaller eatin or informal dining area which leads into great room that looks out over the back yard. Oversized two car garage with lots of room for storage. All the mechanicals are updated including new furnace, electric hot water heater and oil tank. This home is equipped with a propane whole house generator. Your completely fenced in back yard is home to a screened in gazebo, a carefree detached garage, a storage shed and an unbelievable two story barn which has electric and insulated on lower level (WAIT until you see this barn!! Possible make it an ADU or second living space. THIS IS THE ONE YOU HAVE BEEN LOOKING FOR!!!! Priced to be VERY COMPETETIVE. Just a short walk to park springs or a little bit longer walk to center of town.

Listed by Christopher F. Grant of Christopher F. Grant Broker

$
$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Aug 27, 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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Aug 27, 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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27 Gamache Lane Windham CT 06256

MLS Number 24193997

  • Single Family
  • Square Feet 1,648
  • Bedrooms 4
  • Bathroom 2
  • Year Built 1960

Offered for the first time in 24 years and loaded with high-ticket updates, this spacious 1648 ft.2 Cape Cod offers four bedrooms, two full baths, and is set on a private .61 acre lot in a small neighborhood! Over the past 12 years, the seller performed substantial updates including a new metal roof, installed a new central air system with new ductwork, converted from oil to propane, added a high efficiency propane furnace and on-demand water heater, updated 200 AMP electrical, plus a new well pump and retention tank! You can add your personal touch throughout the interior and enjoy everything this Home has to offer! The main level offers a spacious eat-in kitchen with large pantry and access to the side deck, living room with HW floors and abundant natural light, bedroom with HW floors, super convenient full bath and separate 8'5" by 9'7" laundry room! Upstairs find three spacious bedrooms, including the primary with his and her closets, and a shared full bath! Other updates include newer windows (2005 - 2010), septic system (1989) and new Well (1985). The walkout portion of the lower level used to house a wood stove and was set up as a 350 ft.2 rec room, while the basement is great for storage. The yard has lots of possibilities and comes with 2 storage sheds! Centrally located minutes from shopping, restaurants, golf, parks, trails, and farms, while ECSU is 10 minutes away, and UConn Storrs is 15 minutes!

Listed by Jim Burnett of Eagle Eye Realty PLLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Aug 27, 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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1008 Windham Road Windham CT 06266

MLS Number 24190067

  • Single Family
  • Square Feet 2,340
  • Bedrooms 5
  • Bathroom 2
  • Year Built 1950

Do you need an IN-LAW apartment? A Home business? May even be a possible 2 family. It's Possible with this home. Check the Town Hall for all possibilities. VERY LARGE single-family home with 5 bedrooms and 1 1/2 bathrooms. Nice yard, HUGE Dining room, Large Kitchen, a dramatic entrance to the second level!!! Two separate decks, bay windows with lots of natural light. Property needs some work, but the elbow grease will make you TONS of equity. Come look and make an offer!!!

Listed by Victoria Schroeder of Kazantzis Real Estate,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Aug 27, 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: 6.66% last updated on Aug 27, 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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18 Laurel Lane Windham CT 06280

Windham, CT18 Laurel Lane

Price$239,000

Est. Mortgage: $/month

MLS Number 24202236

  • Single Family
  • Square Feet 864
  • Bedrooms 2
  • Bathroom 1
  • Year Built 1958

Welcome home to this beautifully maintained 2-bedroom, 1-bath ranch nestled in a welcoming Windham community. This move-in-ready home offers excellent condition throughout, with a thoughtfully finished basement providing valuable additional living space. A one-car garage adds convenience and storage, while the lovely landscaping creates inviting curb appeal and a pleasant outdoor setting. Ideally located near shopping, medical facilities, universities, and area casinos, this home offers easy access to everyday amenities and entertainment. A wonderful opportunity for those seeking comfort, convenience, and a well-cared-for home in a desirable location.

Listed by Fiona Stevens of Simply Sold Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Aug 27, 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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147 Orchard Hill Lane Windham CT 06226

MLS Number 24170683

  • Single Family
  • Square Feet 960
  • Bedrooms 3
  • Bathroom 1
  • Year Built 1971

Well-maintained 3-bedroom ranch located on a quiet dead-end street. This 960 sq. ft. home offers convenient one-level living with an eat-in kitchen, spacious living area, and a full unfinished basement providing ample storage and future potential. Situated on a level lot, the property features a fenced backyard, mature shade trees that enhance curb appeal, and a wooded backdrop beyond the rear fence for added privacy. Ample off-street parking. Lovingly cared for over many years and ready for its next owner to add their own updates and personal touches.

Listed by Heather Meehan and Frank Villazante of Meehan & Daughters Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Aug 27, 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 Walnut Street Windham CT 06226

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Aug 27, 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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