Windham County, CT Real Estate Search

Windham County, CT 4 Bedroom Homes for Sale

Our website features the best real estate search for 4 bedroom homes available in Windham County, CT and surrounding areas. 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.

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 4 Bedroom Homes for Sale

$2,495,000
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

$2,950,000
4 Beds 5 Baths 24115278 MLS
A rare and refined country estate offering privacy, luxury, and elegance on over 53 acres in scenic Pomfret. This extraordinary 4,442 sq ft custom, Tennessee fieldstone home includes 4 bedrooms and 5 baths-including a private in-law apartment/second primary suite with its own entrance. An additional 16+ acre building lot provides development potential. Surrounded by forest and adjacent to 175 acres of open space, this home sits high with long eastern views into RI! A 1,000 ft paved driveway leads past over 500 ft of hand-laid stone walls to the stunning residence, framed by 10" cedar columns and solid mahogany double doors. The interior exudes craftsmanship with 8' solid wood doors, mahogany floors, 12" triple crown molding, and Marvin windows throughout. The grand great room boasts 20' ceilings and a massive fieldstone fireplace, while the private office stuns with a redwood ceiling, fireplace, and custom cherry built-ins. The chef's kitchen features Viking and Meile appliances, granite counters, cherry details, and opens to a sunny morning room and expansive veranda. The primary suite is a retreat with vaulted ceilings, a luxurious spa bath, radiant heated travertine floors, custom vanities, arched alcoves, and dual walk-ins. Additional highlights include a 3-car garage with Spanish cedar doors, Sonos sound system, generator, 139-head irrigation system, and walk-up basement ready to finish. This is a one-of-a-kind legacy property -stately, expansive, and exquisitely built.

282 & 260 Searles Rd, Pomfret

$1,450,000
4 Beds 6 Baths 24177811 MLS
Set on 10.3 private acres in desirable Woodstock Valley, "Blue Heron Glade" offers a rare blend of privacy, natural beauty, and thoughtfully designed living spaces in Connecticut's Quiet Corner. A long private driveway with a charming cobblestone bridge leads to this exceptional property surrounded by stone walls, abundant wildlife, and a large pond frequented by blue herons. The main residence offers over 6,000SF above grade plus an extensively finished lower level designed for entertaining and everyday comfort. The kitchen features granite countertops, a large center island, and abundant cabinetry. The first-floor primary suite includes tray ceilings, a spa-like bath with double sinks, a 2-person jetted tub, and separate shower. The finished lower level offers a completely unique atmosphere with a custom speakeasy-style bar, theater room, full bath, dog washing station, laundry area, and private office suite with 2 rooms and an additional full bath. An attached in-law apartment has its own bedroom, full bath, kitchen & loft/office area, and newly added white oak flooring. 4 oversized garage bays, 2 of which offer unfinished loft space above. Outside, enjoy the fenced inground pool area with beautifully updated landscaping & a pool house complete with plumbing, granite counters, half bath, & outdoor shower. Fiber internet with mesh nodes provides seamless connectivity throughout the house. A rare Woodstock Valley retreat where privacy, nature, and luxury come together.

1374 Rte 171, Woodstock

$429,557
4 Beds 2 Baths 24176334 MLS
Step into a world of timeless beauty and refined New England charm in this extraordinary 1922 Antique Colonial Victorian, perfectly nestled in the heart of Putnam, Connecticut. Rich with character, elegance, and architectural detail, this remarkable residence beautifully blends historic sophistication with thoughtful modern updates. From the moment you enter, you are welcomed by an absolutely breathtaking grand staircase - a stunning focal point that instantly captures the home's elegance and unforgettable presence. Sunlight pours throughout the spacious interior, highlighting beautiful hardwood flooring, classic craftsmanship, and a warm, inviting atmosphere designed for both everyday living and elegant entertaining. The main level offers a graceful flowing layout featuring a spacious living room, an elegant formal dining room, and a generously sized kitchen ready to host holidays, celebrations, and memorable gatherings. Four spacious bedrooms provide comfort and versatility, while updated bathrooms offer the perfect balance of modern convenience and timeless style. One of the home's most exceptional and rare features is the expansive third floor, offering three additional heated rooms with brand-new carpeting. Whether envisioned as a luxurious primary suite retreat, home office space, guest quarters, creative studio, playroom, fitness area, or additional living space, the possibilities are truly endless. Outside, the property continues to impress with a fenced, level

55 Mechanics St, Putnam

$659,900
4 Beds 3 Baths 24160228 MLS
"Buyer's loss, your gain." Modern Luxury meets timeless design on a Cul-De-Sac in Thompson, CT! 38 Madison Ave was custom-built home in 2020 and set on nearly 2 private acres, this masterpiece redefines move-in ready. Located in a subdivision with underground utilities, this home offers an impeccable blend of curb appeal and sophisticated design. The Exquisite Interior Design boosts the heart of the home a chef's dream kitchen, with a gorgeous quartz island, professional-grade stainless appliances, and a stunning marble-inlay herringbone backsplash. The open-concept layout flows effortlessly into a living area anchored by a dramatic floor-to-ceiling stone-textured accent wall w/electric fireplace. Escape to the expansive Primary Suite, a true sanctuary featuring: A freestanding soaking tub set against a custom mosaic niche and a double vanity with sleek matte black fixtures. A dedicated office alcove with vaulted ceilings and abundant natural light and 3 spacious closets to keep your things organized. Outdoor Living: A large composite deck overlooks a lush, private, and wooded backyard-perfect for quiet mornings or entertaining guests. Home has Central Air, high-efficiency forced air, and a spacious 2-car attached garage. Recently painted throughout! Additional Space: Ready to be finished basement offers the perfect footprint for added living, private home gym or a cozy media room. Schedule your tour today to see this GORGEOUS home! Mins to 395 and Center of Thompson

38 Madison Ave, Thompson

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.