Windham Homes for Sale

Welcome to Windham County, Connecticut—a hidden gem that perfectly blends charming New England character with modern convenience. Nestled in the northeastern part of the state, Windham County is renowned for its picturesque landscapes, vibrant communities, and rich history. From the lush rolling hills to the serene lakes, this county offers a tranquil escape while still being within easy reach of urban amenities.

Windham County is home to a variety of towns, each with its own unique charm. Whether you’re exploring the quaint streets of Willimantic, enjoying the scenic beauty of Mansfield, or experiencing the rich heritage of Putnam, you'll find a welcoming community that prides itself on its local culture and outdoor activities. With an array of parks, hiking trails, and recreational areas, nature enthusiasts will feel right at home.

For those considering a move to this enchanting area, the real estate market in Windham County is thriving. Homes for sale range from historic colonial houses to modern single-family homes, catering to diverse tastes and budgets. Whether you’re a first-time homebuyer or looking to downsize, you’ll discover properties that boast spacious yards, updated interiors, and proximity to local amenities.

With its blend of small-town charm and vibrant community spirit, Windham County is not just a place to live—it's a place to thrive. Explore the homes for sale today and discover the perfect setting for your next chapter in this idyllic corner of Connecticut!

Newest Windham Homes for Sale

$825,000

5 Beds ⋅ 3 Baths ⋅ 24204013 MLS

This beautiful old Colonial home was built on one of the first four parcels of land when Brooklyn was first settled. The historic character is seen throughout the home but with many modern amenities. Five Bedrooms, 2.5 Baths, 2 Fireplaces, 2 Woodstoves, Hot air heat, Newer Windows and beautiful old wood flooring. The attached heated workshop, with 220 Amp Electrical Service, is state of the art and offers many uses. There is a very cool walkup attic, and several outbuildings. The land consists of 21.6 Acres of land with open fields, woodlands and frontage on Blackwell's brook. This lovely setting is off the main road for peace and quiet. The amount of frontage has potential for subdivision and is eligible for a free split.

26 Beecher Rd, Brooklyn

$125,000

2 Beds ⋅ 1 Baths ⋅ 24204737 MLS

Welcome home to this cozy 2-bedroom, 1-bath mobile home offering a peaceful and private setting. Tucked away on a back lot, this home provides plenty of privacy and a quiet place to relax. Inside, a pellet stove adds warmth and comfort during the colder months. Outside, a large shed provides plenty of additional space for storage, tools, lawn equipment, or hobbies. With its private back yard and comfortable layout, this home is a great opportunity for anyone looking for affordable living with a little extra peace and quiet.

12 R And R Park, Killingly

$145,000

3 Beds ⋅ 2 Baths ⋅ 24204778 MLS

This Cute, Clean and Spacious, 3-bedroom, 2 bath home in the Stonegate Manor has 1152 Square Feet of Living Space. Appliances convey. There is an 8x10 Shed that conveys as well. Updates are as follows.... Roof is only 2 years old, and hot water heater only 3-4 years old. New flooring and subflooring in primary bedroom/bath. 2 pets are allowed per park regulations. Park has No age requirement! This home abuts the woods with a Walking Trail leading to the Willimantic Reservoir and surrounding Natchaug River and Mansfield Hollow watershed system. Close to Route 6, Airport, shopping, restaurants and more. Public water and public sewer.

57 Circle Dr, Windham

$509,000

3 Beds ⋅ 2 Baths ⋅ 1422207 MLS

Looking for a home that exudes the character and craftsmanship of bygone days without the challenges of a true antique? 15 Paine District Road looks and feels like it's been here for centuries, but this gorgeous reproduction Saltbox is less than 40 years old. Hand-built by its original owner with extraordinary attention to craftsmanship and period-inspired detail, it offers the warmth and character of early New England architecture recreated for modern living. Huge blocks of granite form the entry steps to each of the three doors, while exposed rough hewn beams and an oversized fireplace harken back to quieter days. Custom cabinetry and millwork by the renowned craftsmen at Brunarhans can be found throughout the home, from the solid wood kitchen, custom chair rails and molding to the raised paneled wall surrounding the fireplace. The kitchen features a cooking island and charming bay window dining nook with built-in seating. The flexible floor plan offers 3 bedrooms, including one on the first floor currently used as an office with more beautiful built in floor to ceiling custom cabinetry. The second floor offers a spacious primary and two additional bedrooms, the smaller one currently being used as a separate laundry area and playroom. The oversized garage includes a workshop area and storage loft. If you think this property looks pretty now, just imagine it when the fall foliage blooms. Act now and you can be moved in by peak leaf season, your pumpkins and scarecrow await!

15 Paine District Road, Woodstock

$679,000

4 Beds ⋅ 3 Baths ⋅ 24202453 MLS

Discover the timeless charm and endless potential of this antique home in Woodstock located down the road from Woodstock Academy and situated on a lovely country road while remaining close to all amenities. Entering through the side door into a lovely sitting/dining area with fireplace that opens to the kitchen, which flows into a large living room, perfect for gathering family or entertaining. There is plenty of space for a home office or den too. Head upstairs where there are 4 spacious bedrooms, the primary having its own dressing room, along with 2 full baths. Lovely wood flooring throughout the home. Rich with character and antique details, this special property offers a wonderful opportunity to refresh, restore and make it all your own. Set 8.5 acres, the grounds provide plenty of room for gardening, agriculture and animals or just a quiet place to relax. The beautiful post and beam barn adds character and versatility, while providing the foundation for hobbies, storage, or animals. Come and discover all the amazing features and opportunities this home has to offer!

122 Child Hill Rd, Woodstock

$1,200,000

3 Beds ⋅ 4 Baths ⋅ 24199723 MLS

Enter this property with a long winding driveway to the home nestled and surrounding by woods. 10.25 Acres zoned AG-2.Three bay Garage attached with an above Covered Deck for large family gatherings! Plus a separate Garage with front and back doors. Outdoor Wood Boiler to heat your home, Patio and Heated Inground Pool, Irrigation system and underground Utilities. Primary Bedroom with his and her closets and bath with a Jaccuzi tub and radiant heat in the floors. Kitchen has a huge center island with a breakfast nook and formal dining, Tiled counters along with tile flooring , 3 Bdrms, 3 baths. Step up Living Room with a Center Stone Fireplace, Bar, Wood Flooring, Spiral staircase to upper level for office space. Lower level has a Den and exercise area and Sauna Room. Security System. Close to Mass and RI lines. Shopping and Golfing nearby. So much to view.Very unique home. Don't Hesitate Call Today for your private showing.

126 E Putnam Rd, Putnam

$350,000

3 Beds ⋅ 1 Baths ⋅ 24198208 MLS

FIRST TIME OFFERED!! Lovingly built and maintained by the original owners, this well-constructed home offers quality, character, and a convenient location near I-395 and the Rhode Island border. Located on a dead-end road and situated on a beautiful corner lot, this property INCLUDES the .58-acre house lot PLUS an ADDITIONAL .31-acre wooded lot at 510 FALL BROOK RD for a TOTAL OF .89 ACRES. Inside, discover solid wood floors beneath the carpeting, newer kitchen cabinetry, and a truly unique antique oven/range that adds charm and personality to the kitchen. The finished breezeway is a wonderful bonus space, featuring a stone-faced wall and sliders leading to the backyard deck, perfect for enjoying the spacious backyard. Garden enthusiasts will love the abundant space to cultivate their own outdoor haven. Anderson Renewal windows, approximately 4-5 years old, provide peace of mind, while central air adds year-round comfort. The one-car attached garage features an electric door opener. The lower level offers a practical work area with a built-in workbench, washer and dryer, and utility sink. PRICED TO SELL, this is a rare opportunity to own a solid, owner-built home with a beautiful corner lot, an additional wooded parcel, and an excellent location close to major highways and the Rhode Island line.

34 Fall Brook Rd, Killingly

$324,999

3 Beds ⋅ 1 Baths ⋅ 24204531 MLS

Welcome to this charming 3-bedroom, 1-bathroom ranch-style home in Plainfield, offering comfortable one-level living with a peaceful, set-back-from-the-road setting. This move-in-ready home features a brand-new roof and new windows, providing added peace of mind for years to come. Inside, you'll find new luxury vinyl plank (LVP) flooring throughout the main living areas, along with new carpeting in the bedrooms for added comfort. The property is served by public septic. Full home inspection, termite, radon and water testing just completed and available for review upon request. With major updates already completed, and a welcoming ranch layout, this Plainfield home is ready for its next owner to make it their own. Come see all it has to offer! Agent owned.

23 Shepard Hill Rd, Plainfield

$489,900

3 Beds ⋅ 2 Baths ⋅ 24202685 MLS

Welcome to this beautifully maintained open-concept ranch, built in 2008 and situated on a private, level 3.6-acre lot. Offering 3 bedrooms and 2 full bathrooms, this home combines modern comfort with spacious single-level living. The bright, open floor plan features gleaming hardwood floors, tray and cathedral ceilings and two gas fireplaces. The kitchen boasts stainless steel appliances, granite countertops, tall cabinets and a convenient desk area. You'll find a seamless flow between the kitchen, dining, and living areas, making it ideal for both everyday living and entertaining. A sun-filled sunroom provides the perfect spot to relax and enjoy views of the surrounding property, while the deck offers additional outdoor living space for gatherings or peaceful mornings. Car enthusiasts, hobbyists, and those in need of extra storage will appreciate the impressive 5-car garage capacity, including an attached 3-car garage and a detached 2-car garage. The expansive 2100 sq ft basement presents excellent potential for future finishing with a bath location already plumbed in. The possibilities are endless to create additional living space, a recreation room, home gym, or workshop. Don't miss this opportunity to own a move-in-ready ranch with room to grow both inside and out!

6 Zoldak Dr, Windham

$509,000

3 Beds ⋅ 2 Baths ⋅ 24204065 MLS

Looking for a home that exudes the character and craftsmanship of bygone days without the challenges of a true antique? 15 Paine District Road looks and feels like it's been here for centuries, but this gorgeous reproduction Saltbox is less than 40 years old. Hand-built by its original owner with extraordinary attention to craftsmanship and period-inspired detail, it offers the warmth and character of early New England architecture recreated for modern living. Huge blocks of granite form the entry steps to each of the three doors, while exposed rough hewn beams and an oversized fireplace harken back to quieter days. Custom cabinetry and millwork by the renowned craftsmen at Brunarhans can be found throughout the home, from the solid wood kitchen, custom chair rails and molding to the raised paneled wall surrounding the fireplace. The kitchen features a cooking island and charming bay window dining nook with built-in seating. The flexible floor plan offers 3 bedrooms, including one on the first floor currently used as an office with more beautiful built in floor to ceiling custom cabinetry. The second floor offers a spacious primary and two additional bedrooms, the smaller one currently being used as a separate laundry area and playroom. The spacious garage includes a workshop area and storage loft. If you think this property looks pretty now, just imagine it with the bloom of foliage. Act now and you can be moved in by peak leaf season, your pumpkins and scarecrow await!

15 Paine District Rd, Woodstock

$415,000

4 Beds ⋅ 1 Baths ⋅ 24196428 MLS

~*~ BRING YOUR CREATIVITY ~ TOOL BOX & LONG TERM VISION to 303 RIVERSIDE DRIVE!! ~*~ ... Although this Property Requires The "3 RRRs" Renovation, Repairs & Restoration .... It will be a Rewarding Opportunity for the Right Buyer!!!... Being Sold As-Is....This Cape Style House comes with 4 Sprawling Acres of Wooded Privacy! Not to Mention the "Aged" wide Stonewall Borders!... The House offers 1,652 Square Feet of Living Space across 2 Floors ~ 4 Very Good Sized Bedrooms - 2 on Each Level!.. This Classic Layout has a Wood Fireplace, Dining Area and Sun Room!.. Oil Heat, Private Well & Private Septic (Recently inspected showing a functioning system)... The Crown Jewel of this Property is the Two-Story Barn!!.. Need extra Storage? Need a Work Shop? Need a Fun Place for the Grandkids to hang out?... Endless Possibilities!!.. And there's More..... 1-Car Garage and a Separate Structure on the hill once used as a Kids Place House! .... The back part of the land borders the AIRLINE TRAIL !.. Highway Access is only Minutes to I-395! You will be close to Antique Shopping , Great Dining & Entertainment in the Surrounding Towns!!... Bring your Furry Friends to the West Thompson Dam ~ walking trails. You are also close to the Woodstock Orchards ~ Just in time for "Pick Your own Apples!!" ... Or Relax with an Adult Beverage at the Tree House Brewery and/or Taylor Brook Vineyard!... Don't miss this Opportunity !! :)

303 Riverside Dr, Thompson

$600,000

4 Beds ⋅ 3 Baths ⋅ 24204008 MLS

Modern amenities meet unmatched seclusion in this 2,000+ sq ft colonial. A mostly level lot offers abundant green space, fruiting plants, and perennials, while the side deck and yard open to a beautiful natural view of the Still River-ideal for outdoor entertaining or quiet, serene living. Inside, gleaming maple floors lead to a first-floor bedroom with attached pass-through bath, a modern eat-in kitchen with double wall ovens and a propane stovetop, a large dining room, and a spacious living room with a functional fireplace. Upstairs, a hallway full bath serves three additional bedrooms, including the primary suite with its own attached full bath. The walk-up attic's excellent ceiling height and volume create a strong opportunity to add livable square footage. The basement's layout and ceiling height are equally well suited to finishing and expanding the home further. An attached two-car garage and paved driveway provide ample parking. If you want modern comfort, privacy, and room to grow in a peaceful woodsy setting, this is the home for you!

47 Sherman Rd, Woodstock

Start Your Search

IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but is not guaranteed. © 2026 State-Wide Multiple Listing Service. All rights reserved. Data Last Updated:

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.