Windham Real Estate

Welcome to Windham, a hidden gem nestled in the picturesque landscapes of New England! This charming town, located in the heart of Windham County, Connecticut, is known for its rich history, vibrant community, and stunning natural beauty. With a population that values both tradition and progress, Windham offers a unique blend of small-town charm and modern amenities, making it an ideal place to call home.

As you explore Windham, you’ll be captivated by its historic architecture, including the beautifully preserved buildings in the downtown area. The town is steeped in history, with roots dating back to the 18th century, and this heritage is reflected in its local culture and community events. Windham is home to several parks and recreational areas, such as the scenic Windham Town Green and the expansive Willimantic River, providing residents with ample opportunities for outdoor activities, from hiking and biking to fishing and picnicking.

Families will appreciate the excellent educational institutions, including public schools that are dedicated to fostering a supportive learning environment. The community is also rich in arts and culture, with various festivals, galleries, and theaters that showcase local talent and bring residents together.

Windham’s location offers easy access to major highways, making it a convenient spot for commuting to nearby cities like Hartford and Norwich. Whether you’re looking for a cozy single-family home, a charming condo, or a spacious rental, Windham has a diverse real estate market that caters to all lifestyles. Come discover the warmth and welcoming spirit of Windham – your new home awaits!

Newest Listings in Windham

$749,900

4 Beds ⋅ 3 Baths ⋅ 5109291 MLS

Welcome to a truly unforgettable property where amazing grounds, winding stone pathways, a koi pond with cascading waterfall, and an in-ground pool create the setting for a spectacular private retreat. 34 Sharon Road is a one-of-a-kind Garrison offering remarkable craftsmanship, an enchanting garden setting, and incredible potential for its next chapter. Set among mature trees and extensive stonework, this 4 bedrooms, 2.5 baths home offers 2,780 sq. ft. of official living area, plus a four-season greenhouse and striking Hartford conservatory. Inside, hardwood floors and exceptional custom trim create warmth and character throughout. The showstopping family room features a soaring vaulted ceiling, dramatic exposed beams, rich wood detailing, and an impressive floor-to-ceiling brick fireplace. The custom kitchen includes maple cabinetry, granite countertops, a center island, and two ranges—including a professional-grade Viking range with matching hood. Generous living and entertaining spaces provide a flexible layout ready to be reimagined. All four bedrooms are located upstairs, including a primary suite with its own en-suite bathroom. The unfinished lower level offers lots of potential, including a spacious work area, loads of storage, and access to a two-car garage. Whether used for hobbies, projects, recreation, or additional storage, this lower level provides valuable flexibility. The Asian-inspired gardens and water features make the outdoor setting truly special. The distinctive conservatory and four-season greenhouse with built-in heat lines offer exciting possibilities for gardeners, artists, or anyone dreaming of a truly unique sanctuary. The home and grounds require work and have deferred maintenance. Property is being sold as-is. Bring your creativity and unlock the full potential of this hidden Windham gem! Come visit the Open House 9/12 (Sat) and 9/13 (Sun) from 1:30PM-3:00PM

34 Sharon Rd, Windham

$824,900

3 Beds ⋅ 2 Baths ⋅ 5109201 MLS

Gorgeous custom built ranch in highly desirable Windham Estates. Stunning facade and recessed entryway add to the most inviting curb appeal. Foyer is open to kitchen and expansive living room. Gas fireplace flanked by built in shelving with crown moldings and warm toned hardwood flooring throughout. Tall maple cabinetry with stainless appliances, center island and 6 foot patio doors highlight the beautifully equipped kitchen. Pantry and laundry room are conveniently tucked away off the main living area. Flex space adjacent to kitchen, ideal den or home office overlooks wooded landscape and fenced inground pool area. Primary en Suite with double sinks and walk in shower with designer tile and stone tops. Additional bedrooms and full bath are well sized and neutral tones continue with the cohesive floorplan. Deck and screened porch make entertaining poolside comfortable for enjoyable seasonal living. Generator, central air, central vac, irrigation and direct entry attached two car garage. True one level living in almost 2100 sf with quality upgrades are a rare find in this sought after community. Top performing school system in Southern NH's most coveted town. Come see this gem! OPEN HOUSES Friday 9/11, 4pm-6pm, Saturday 9/12, 10am-12 and Sunday 9/13, 10am-12.

8 Rolling Ridge Rd, Windham

$1,375,000

5 Beds ⋅ 4 Baths ⋅ 5109182 MLS

Welcome Home to Luxury & Space in Windham! Nestled on a quiet cul-de-sac on a private .89 acre lot, this stunning colonial offers sophisticated craftsmanship, modern amenities, and multi-level living. Designed with exceptional attention to detail, this light-filled home delivers the perfect layout for both daily living and large scale entertaining. The heart of the home is the Gourmet Chef's Kitchen equipped with a center island, granite countertops, double wall ovens, gas cooktop, mini fridge, and stainless steel appliances. The oversized kitchen effortlessly opens into the family room with a fireplace featuring detailed crown molding and rich hardwood flooring throughout. The dedicated formal dining room and private home office is accented by wainscoting and a high-ceiling entry foyer with hardwood staircase. Upstairs you will be impressed with the generous sized primary bedroom suite featuring an updated full bath with soaking tub, separate shower, double sinks and large walk in closet. There are 3 additional bedrooms, a full bath and laundry room on this level. The expansive 3rd floor has a home theater with chairs, projector and screen. There is also a bedroom and bonus room. Need more space? The finished walkout basement offers a bar, sauna, game room and plenty of storage space. Step outside into your own private resort-style oasis. The beautifully landscaped backyard is designed for high-end entertaining and everyday relaxation, highlighted by a sparkling heated saltwater pool complete with a relaxing waterfall feature. Host summer gatherings with ease at the fully equipped outdoor kitchen, or step into the dedicated pool house for shade, convenience, and extra storage. Whether lounging by the water or dining under the stars, this outdoor retreat delivers the ultimate setting for luxury outdoor living. THIS PROPERTY IS A GEM! Don't Delay! Schedule your private showing today!

24 Nathan Rd, Windham

$415,000

2 Beds ⋅ 3 Baths ⋅ 5109138 MLS

Enjoy low-maintenance living at Hardwood Heights in Windham, offering comfort, space, and character. Skylights fill the home with natural light, while the fireplace adds warmth and charm. Fresh interior paint, new baseboards, durable vinyl flooring, and a brand-new heating and cooling system make this home move-in ready. The spacious kitchen flows into the dining and living areas, while the upstairs bedrooms offer recessed lighting, ceiling fans, powered skylight shades, and en-suite bathrooms. The updated primary bath features a newer tub and shower. A private deck, partially finished lower level, and generous garage storage provide added flexibility and convenience. Close to shopping, dining, and major commuter routes. Welcome home! Showings begin at the open house on Saturday 9/12 @ 2pm.

62 Stacey Cir, Windham

$399,000

2 Beds ⋅ 3 Baths ⋅ 5109111 MLS

Welcome to this desirable townhouse in popular Windham, NH, offering an ideal blend of space, flexibility and value with no age restrictions and pets allowed. The main level features a comfortable family room with fireplace, dining area and kitchen, creating an easy layout for everyday living and entertaining. A convenient half bath with laundry completes the first floor. Upstairs, the spacious primary bedroom suite includes a bonus loft area that can easily serve as a home office, reading nook, craft space or whatever fits your lifestyle. The second bedroom offers the added convenience of its own private bath, making it perfect for guests. Need even more space? The basement offers two additional bonus rooms with endless possibilities for a home gym, office, hobby room, playroom or media space. An attached one car garage, central air and a condo fee that includes water, sewer, trash, snow removal and lawn care add to the convenience. The home could use some fresh paint and new carpet, giving you the opportunity to add your own personal touches and make it truly yours. Priced with this in mind, there is excellent potential to build instant equity, and the seller is offering a concession toward painting to help get you started. Bring your vision and take advantage of this opportunity to own a home in one of Windham’s sought after communities! Showings begin Friday, September 11th in the afternoon. Welcome Home!

61 Stacey Cir, Windham

$599,000

3 Beds ⋅ 2 Baths ⋅ 5108856 MLS

Set on 1.84 acres in a desirable Windham location, this 3-bedroom, 2-bath split-level offers space, privacy, and plenty of potential to make it your own. Tucked away on a dead-end road and situated across from a former apple farm, the property enjoys a peaceful setting while still being convenient to everything Windham has to offer. An added bonus is direct access to the rail trail right from the property, perfect for walking, biking, and enjoying the outdoors. Inside, hardwood flooring runs throughout much of the main level, while a spacious sunroom and wood-burning stove add warmth and character. Step outside onto the deck overlooking the private backyard, offering a wonderful setting to relax, entertain, or simply enjoy the surrounding natural landscape. The finished lower level provides additional living space with flexibility for a family room, home office, gym, or more, and a two-car garage offers added convenience and storage. Ready for your personal touches and updates, this home presents an exciting opportunity to create something truly your own in one of Windham’s most desirable communities. With nearly two acres, a peaceful setting, and a versatile layout, there is so much potential to make this property shine.

36 Governor Dinsmore Rd, Windham

$884,900

2 Beds ⋅ 3 Baths ⋅ 5108741 MLS

Introducing an exceptional new luxury duplex community in one of Windham's most desirable locations. Thoughtfully designed for today's lifestyle, these stunning new homes combine modern elegance, quality craftsmanship, and energy-conscious construction to create the perfect balance of comfort, style, and convenience. Step inside and discover bright, open living spaces enhanced by soaring ceilings, oversized windows, and carefully curated finishes throughout. The heart of each home features a beautifully appointed kitchen with quartz countertops, stylish accents, and seamless flow into the spacious living area, where a cozy fireplace creates the perfect gathering place for family and friends. Designed with flexibility in mind, these homes offer versatile living areas and multipurpose flex spaces to accommodate work, hobbies, guests, or changing lifestyle needs. Enjoy effortless indoor-outdoor living with a welcoming covered front porch and a private patio or deck for relaxing and entertaining. Upstairs, retreat to a luxurious primary suite featuring dual vanities, a custom tiled shower with glass enclosure, and two generous walk-in closets. A second bedroom, full bath, expansive loft, and convenient second-floor laundry provide both comfort and functionality. Additional features include a two-car garage, full unfinished basement offering future expansion potential, and several green-building features designed to help reduce energy costs while supporting a low-maintenance, executive lifestyle. Ideally situated near major highways, shopping, dining, recreation, nature trails, and Windham's highly regarded schools, this exciting new community offers the perfect combination of luxury, convenience, and modern living. *** This is a construction site and for your safety it is shown by appointment ONLY (or at the scheduled open house) *** GPS 47 North Lowell Rd.

5 Campbell Way Unit 2, Windham

$1,100,000

2 Beds ⋅ 3 Baths ⋅ 5108732 MLS

Rarely does an opportunity come along to own a brand-new home in such a desirable lakefront setting. Set on a peaceful road overlooking beautiful Cobbetts Pond, this property combines privacy, natural beauty, and access to one of Windham’s most sought-after recreational communities. With zoning variances and approvals in place and construction well underway, this thoughtfully designed year-round residence is already framed and approaching the sheetrock stage, with anticipated completion by the end of October. The home features two bedrooms, two full bathrooms, and three levels of living space. Both bedrooms have balcony access, creating a peaceful retreat to relax and enjoy the tranquil water views. The main level also offers a walk-out deck, providing an inviting outdoor space to take in the beautiful lake surroundings. The walk-out lower level adds valuable living space and flexibility, while the elevated setting allows the home to capture the beauty of its surroundings. Deeded beach rights and water access provide the opportunity to enjoy all that Cobbetts Pond has to offer, from summer days on the water to quiet evenings overlooking the lake. Ideally situated for both relaxation and convenience, this private lakeside setting remains within easy reach of major highways, Boston, Tuscan Village, airports, and area schools. This is a rare opportunity to own a distinctive, brand-new residence in one of Windham’s premier lake communities, with the construction already underway and the vision becoming a reality.

14 Second St, Windham

$569,000

6 Beds ⋅ 5 Baths ⋅ 5108718 MLS

Set on a scenic country property in Windham, this expansive home offers exceptional space, flexibility and a setting with real character. Currently used as a large single-family residence, the home was originally built as a three-family property, with a common entrance serving two living areas and a separate entrance to the garden-level apartment. A central stairwell can connect the spaces, creating options for a large household, multi-generational living, guests, home offices or future reconfiguration. The three living areas include full kitchens, generous living rooms and a total of six bedrooms, with expansive rooms and large windows throughout. There is also ample storage and flexible space for a workshop, studio or dedicated home office. The grounds are where this property becomes especially memorable. Shaped over the years by an artist’s eye and a love of the land, the organic gardens feel established, abundant and wonderfully personal, with fruit trees, flowering shrubs, mature plantings and productive raised beds built at waist height. Several decks and screened porches invite you to slow down and take in the setting, while the property unfolds into a pond, large meadow, playing field, trout stream and walking trails, with views toward Turkey Mountain Ridge. There is a quiet, almost timeless quality here that is increasingly hard to find. Located off the beaten path in picturesque Windham, yet convenient to Southern Vermont skiing, hiking and year-round recreation, the property offers room to live, create, gather and breathe. The home does need TLC and updating, but its scale, versatile layout, organic gardens, land and natural setting make it a true diamond in the rough with tremendous potential.

1113 Old Cheney Rd, Windham

$499,000

3 Beds ⋅ 2 Baths ⋅ 5108371 MLS

Tucked into the peaceful woods of Windham, Vermont, this cherished Timber Ridge residence offers a rare opportunity to own a piece of true Vermont legacy. Custom built and lovingly held by the same family across three generations, this home is filled with decades of storied memories, seasonal celebrations, and effortless mountain living. Set on a picturesque one acre wooded parcel, the home’s expansive wrapping decks elevate you straight into the canopy, creating an immersive, treehouse like atmosphere. Whether you are sipping morning coffee surrounded by autumn foliage or relaxing after a day on the slopes, the setting offers complete tranquility and privacy. Inside, the layout balances comfort, versatility, and classic rustic charm. Enjoy seamless single level living with a spacious primary suite located right on the main floor. The home features three dedicated bedrooms (currently designated as four on the town lister card), offering ample space for a crowd. A finished bonus room, previously used as a home office , adapts easily to a bunk room, play area, or secondary media lounge. The pellet stove keeps it warm and the separate entrance allows for privacy. A dedicated workshop provides the ideal footprint for tuning skis, maintaining gear, or tackling creative hands on projects. Located in the heart of the Green Mountains, Timber Ridge serves as an exceptional four season basecamp. Winter enthusiasts will appreciate having five major ski areas within a 30-minute drive, while summer brings endless outdoor recreation, from nearby lakes, ponds, and hidden waterfalls to vibrant local farmers markets, hiking trails, and artisanal shops. This special home stands ready to welcome its next chapter and a new generation of mountain memories.

756 Birch Hill Rd, Windham

$775,000

3 Beds ⋅ 3 Baths ⋅ 5108121 MLS

OFFER DEADLINE TUESDAY 9/8 4:00pm. Gorgeous custom cape set in a beautiful cul-de-sac neighborhood, with easy access to I-93 at exit 3. You’re sure to appreciate that the home is set back on a professionally landscaped lot. The entrance opens to the formal dining room, with hardwoods and vaulted ceiling with skylights, all opening to a balcony. Enjoy the gorgeous custom kitchen, with big center island, granite counters and stainless-steel appliances. A vaulted ceiling living room is located off the front foyer. The office/den opens to a dramatic two-story solarium, with handsome wood ceilings, taking in the views of surrounding woodlands. The family room is open to the kitchen and features hardwood floors and a stone fireplace. Tucked privately off the dining room is a beautiful sunroom, featuring the warmth of wood walls, with vaulted ceiling and skylights. Completing the first floor is a powder room with an elegant vanity and a laundry area. The second-floor features three bedrooms with lovely updated baths. The spacious primary suite features a brand-new private, 3/4 bath. The interior is all freshly painted and new carpeting in bedrooms. The walk-out lower level features a huge gathering room with daylight windows, and sliders to the patio. The mudroom offers direct access to two-car garage. The outdoor living space has a wonderful patio area and a huge deck. You will also find raised beds for your gardening needs. This home has a warm and inviting appeal with dramatic cotemporary features. Don’t hesitate… this is an excellent value in sought after Windham NH.

38 Sharon Rd, Windham

$695,000

3 Beds ⋅ 3 Baths ⋅ 5107952 MLS

Brand-new construction in beautiful Windham, Vermont! This thoughtfully designed three-bedroom home with an additional bonus room offers the comfort, efficiency, and ease of new construction paired with a peaceful Vermont setting. Filled with natural light, the home features bright, welcoming living spaces and a versatile floor plan designed for both everyday living and weekend escapes. The bonus room provides valuable flexibility for a home office, guest space, playroom, or den. An attached two-car garage makes Vermont living especially convenient, providing sheltered parking along with plenty of room for skis, bikes, outdoor gear, and storage. Outside, the yard offers space to relax, play, garden, or entertain, while the firepit creates the perfect gathering spot for summer evenings, crisp fall nights, and après-ski get-togethers. Located in the quiet mountain community of Windham, this property puts four-season recreation within easy reach. Five major ski areas—Stratton, Bromley, Magic Mountain, Okemo, and Mount Snow—are all located within approximately 35 miles of town, providing an incredible variety of winter adventures. When the snow melts, explore nearby hiking and biking trails, enjoy fishing, paddling and swimming, or spend the day at destinations such as Lowell Lake and Jamaica State Parks. The greater Windham region is known for its extensive trail network and abundant opportunities for hiking, mountain biking, snowshoeing, cross-country skiing, and snowmobiling. Whether you're searching for a full-time Vermont residence or a low-maintenance mountain getaway, this newly built home offers a wonderful combination of modern comfort, outdoor space, and access to everything that makes Southern Vermont special.

717 Horsenail Hill Rd, Windham

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