Windham County, CT Real Estate Search

Windham County, CT Homes for Sale

Our website features the best Windham County, CT real estate search for homes available. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

Windham County, CT Homes for Sale

Avg. No of Beds
Avg. No of Baths
Avg. Living Ft2
Avg. Listing Price
Cost per ft2
Days on Market

Curious about what’s happening in the Windham County, CT real estate market? Sign up for a  Windham County, CT Real Estate Market Report to see what’s active, under contract, and sold!

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Newest Windham County, CT Homes for Sale

158 W Quasset Rd, Woodstock
$1,995,000
4 Beds ⋅ 4 Baths ⋅ 24180508 MLS
Extraordinary Waterfront Estate. Set on an exceptional 5.5-acre private lot with 265 feet of shoreline frontage, this completely rebuilt luxury residence offers a rare opportunity to own one of Woodstock's premier lakefront properties. Arrive via a long, newly paved private driveway that winds through a tranquil setting before revealing this stunning waterfront retreat. Offering 3,971 square feet, 4 bedrooms, and 4 bathrooms, the home was rebuilt from the ground up with next level quality and craftsmanship. Designed for both elegant entertaining and everyday enjoyment, the layout includes a formal dining room, spacious family room, custom mudroom, and a beautiful living room with propane fireplace overlooking Quasset Lake. The showpiece kitchen is truly one-of-a-kind, featuring handcrafted cabinetry by a New York artisan cabinet maker, thick quartzite countertops, premium built-in appliances, and a dramatic tray ceiling with custom white oak detailing. Luxury finishes continue throughout with veneer plaster walls, custom white oak vanities, a professionally designed primary closet, handmade laundry room cabinetry, and architectural flangeless LED lighting seamlessly integrated into the wood ceilings. Built with 2x6 construction, engineered floor systems, 2x12 roof rafters, red cedar siding and trim, central air, all-new heating and cooling systems, underground 400-amp service, and an automatic whole-house generator. Step outside and embrace the ultimate lake lifestyle.

158 W Quasset Rd, Woodstock

433 Wrights Crossing Rd, Pomfret
$6,450,000
12 Beds ⋅ 9 Baths ⋅ 24101484 MLS
Welcome to Bark Meadow Farm, a 127-acre legacy estate once cherished by the Gulden mustard family in CT's "Quiet Corner." The journey begins at a majestic entrance, where a striking allee of century-old maples stands alongside magnificent oaks nearing 200 years of age. This multi-generational compound offers 12 bedrooms & 7.2 bathrooms across three year-round residences. At the heart is the 1799 Main Residence, a 7,577 SF, 5-bedroom, 5.2-bathroom masterpiece of timeless architecture. Ideal for grand-scale entertaining, the butler's pantry flows seamlessly from the exquisite dining room into a spacious eat-in kitchen, complete with a Viking Professional stove. Additional structures include a 1900 Caretaker's Residence (4 bedrooms) & a 1948 14-stall barn with a 3-bedroom apartment above-ideal for a barn manager or rental income, it also offers great potential for a remote home office. Car collector enthusiasts & woodworking hobbyists will love the ultra-spacious garage, complete with a large workshop, a walk-in laundry/tack room, & a powder room. Amenities abound: 2 inground pools, an enchanting pool house with a potting room, raised-bed gardens, & a tranquil bass pond. Enjoy direct access to the Air Line Trail for riding/hiking. The estate directly abuts the CT Audubon Society land, with its beautiful trails located just a half-mile down the road, while the prestigious Pomfret & Rectory Schools are a mere 1.5 miles away. Conveniently accessible to Hartford, Providence/RI

433 Wrights Crossing Rd, Pomfret

500 Hampton Rd, Pomfret
$364,000
2 Baths ⋅ 24173858 MLS
Position your business where visibility, flexibility, and opportunity come together. This beautifully updated commercial property offers over 2,600 sq ft of single-level space at the highly traveled Abington 4 corners of Rt 44 and Rt 97 - a prime location designed to maximize exposure and business growth. Inside, a welcoming front entry opens into a spacious main area filled with endless potential. Ideal for retail, office, industrial, studio, showroom, or service-based use, the flexible layout can easily adapt to your vision. Two additional rooms flow openly off the main space, perfect for offices, meeting rooms, workstations, or added retail display areas. The property also features two half bathrooms, an employee kitchenette/breakroom, and rear access with a second entrance and exit. Outside, a charming picnic and luncheon area offers a great space for employees to relax. Additional functionality includes a lower parking area with a large overhead garage door and expansive storage or maintenance space. An upper driveway and parking area provide easy access for customers and staff, while the smaller garage offers convenient loading, storage, and direct building entry. Extensive recent upgrades include a brand-new roof, refinished original floors, new sheetrock, updated windows, new bathrooms, fresh interior and exterior paint, landscaping, and more. With exceptional visibility on a state highway and endless commercial potential, this is a move-in ready business locatio

500 Hampton Rd, Pomfret

13 West Pkwy, Plainfield
$2,200,000
24161940 MLS
Prime opportunity to own a custom-built 15,000 square foot commercial/industrial facility located within the highly desirable Plainfield Industrial Park. This versatile property offers a flexible layout ideal for manufacturing, distribution, contractor operations, light assembly, or flex office/warehouse users. The building features ADA-compliant office space including seven private offices, reception area, conference room, and employee lounge. Approximately 7,500 square feet of warehouse space is complemented by central air conditioning and 18-25 foot clear span ceiling heights, creating an efficient environment for a wide range of industrial or operational needs. Constructed with 5-6 inch reinforced concrete floors and polished concrete finishes, the warehouse area is designed for durability and heavy-duty use. The building includes six (6) 14-foot overhead doors, allowing for efficient loading and operational flexibility. Additional building features include radiant heated floors, hydro-air heating system, oil-water separator, and a surveillance security system, supporting a variety of industrial and contractor uses while providing added operational security. The exterior offers 12 on-site parking spaces, irrigation, and rear private storage, creating a functional and professional setting for employees and daily operations. Strategically located just 0.5 miles from Interstate 395, the property provides excellent accessibility for trucking and regional distribution.

13 West Pkwy, Plainfield

Start Your Search

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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.

How much is your home worth?

Get instant property value now!