Search Windham Homes and Real Estate

Windham Homes for Sale

About Windham New YorkWindham NY Homes for Sale in the Catskills

Windham is a smaller town in New York located in Greene County. Residents of Windham live in an area that has a rural feel. A majority of Windham residents own their homes. This area is popular due to its ski resort. The town of Windham, located in the heart of the Catskills, is a quiet, quaint village.

Outfitted with all the creature comforts needed to make this an ideal all-year-round vacation home. Windham offers a lot of bars, and restaurants, as well as shops, and boutiques. Windham is known for its mountain ski resort. The small town in the Catskills has a great ambiance and is only a few hours from the big New York City. This area is known for being the Northeast's premier year-round outdoor recreation destination. There are excellent trails and skiing, and Windham mountain has a lot to offer in all seasons. If you are a resident or vacationer, you will want to check out the Windwood Inn, Windham Golf Club, Alpine Spa, Skyride, and world-class bike park. Windham is a great place for your family with all of the activities and amenities at your fingertips. Whether you are a full-time resident or a vacation homeowner, Windham is a great place to be.

Dating back to the late 1700’s, Windham is one of the oldest towns in the region and is often referred to as the “gem of the Catskills.” While the town is rich in history, its charm and beautiful downtown district entices both locals as well as tourists visiting the area. The Historic Main Street looks like the backdrop to a movie and is lined with locally owned boutiques, restaurants, coffee shops and more, ensuring there is something to enjoy for those of all ages. If browsing the local shops isn’t up your alley, fear not, for there is a lot more to explore in Windham!

Windham is surrounded by an abundance of outdoor recreation, from skiing and snow sports, to hiking, ample biking trails, golf courses and more. Take a stroll along the famous Windham Path and enjoy sips from The Vineyards at Windham. The town hosts multiple annual, seasonal, and regular events, from tree lightings to farmers markets and more, the town has kept a true community feel, despite the growth that Windham continues to see each year. A perfect escape, Windham is a true oasis tucked into the mountains, an idyllic place for those of all ages to call home

Windham Schools

Windham offers great schools for its residents who are school-aged children. In Windham, your children will attend, Windham-Ashland-Jewett Central School. This K-12 school is situated in a beautiful mountainous area within Catskill State Park. The school's mission statement is to provide the resources and environment that maximize the opportunity for every student to reach his or her academic, creative, and athletic potential.

Windham Real Estate

Windham offers a range of available real estate. You can find single-family homes, townhomes, condominiums, and vacant land. A good percentage of residents are part-time residents using their property as vacation homes. Some new developments are coming to the area with townhomes and semi-attached homes to accommodate the resort town. Depending on what you are looking for, you can find a secluded log cabin or a single-family home in a community with an abundance of amenities.

What to Know About Windham

A Mountain Town

Windham is a year-round destination, and the same can be said for its namesake, the Windham Mountain Resort. During the summer months, golf 18 holes on the Windham Country Club public golf course. When snow falls and blankets the Catskills, enjoy the best of 1,600 vertical feet of skiing. 

Local Cuisine 

Home to the finest dining in the Catskills, come to Windham hungry and leave satisfied. Eat local at the Windham Local Public House, utilizing farm-sourced ingredients in creative dishes. Enjoy a glass of wine on a date night at the Ze Windham Wine Bar. Breakfast is the most important meal of the day, so we suggest the Catskill Mountain Country Store and Restaurant for an unforgettable meal. 

Unique Activities

With a plethora of unlimited activities and other such charming places to explore, it comes as no surprise that Windham is a popular destination for adventure enthusiasts as well as relaxed travelers. Walk along The Windham Path, and sip wine at The Vineyard at Windham. Browse some of the most visually stunning art displays at the Windham Fine Arts Gallery. 

The Best Neighborhoods 

Living in Windham offers residents a sparse suburban feel with the allure of urban accessibilities whilst living the life of hometown warmth. Full of historic charm, many featured well-established neighborhoods such as Pomfret, South Woodstock, and Woodstock just to name a few, provide a harmonious blend of suburban living with proximity to essential amenities. 

Great Education

The renowned Windham-Ashland-Jewett Central School District serves the town of Windham and the source of education is the K-12 school, Windham Ashland Central School. Students are offered a strong educational foundation fostering growth and the transition from the elementary to high school learning level, whilst providing support services to students in future endeavors of higher education or joining the workforce. 

Local Events 

Windham for its size has a strong sense of community, and for its scenic advantage, offers some of the finest seasonal events to date. Celebrate fall foliage with fifty vendors of local crafts and foods at Windham’s 29th Annual Autumn Fair. When the town of Windham is blanketed in snow, don’t miss the colorful and cheery Holiday Celebration & Tree Lighting and Annual Light Parade in December. 

Interested in the allure of the Gem of the Catskills? Whether it is the year-round outdoorsy amenities that draw you or the well-established communities near a fine K-12 school, Windham has it all. 

What Locals Say About The Area

“I moved to Catskill a few months ago. I like living here. I spent my weekend hiking around the area of Catskill Mountain. I went to the lake and stream to do fishing. In Catskill mountain, the scenes are so beautiful. I would love to do skiing one day at Hunter. The people are so friendly. We do have a lot of local farmer markets every week in the summer.”-Niche

In Conclusion

To learn more about relocating to Windham or any Catskills real estate, contact our office at any time. We would love to assist you with any real estate needs whether it is buying, selling, or investing.

Want to rent before you buy in the Catskills!? Learn more

Windham Homes for Sale

$2,899,000
7 Beds 6 Baths 152967 MLS
Welcome to luxury mountain living at its finest! This brand-new custom-built 7 Bed, 5.5 Bath mountain chalet spares no expense in providing the ultimate living experience. Prepare to be wowed as you step inside and feast your eyes on the breathtaking direct views of Windham that greet you. With four En Suite bedrooms, including a private guest suite, this home offers the perfect blend of comfort and privacy. Set on five acres of private land, you'll have plenty of space to unwind and enjoy the tranquility of nature. And with no HOA to worry about, you'll have the freedom to make this home truly your own. The heart of this chalet is the imported German kitchen and bar, complete with a hidden pantry, huge island, double dishwashers, and a Viking 8 burner stove. Whether you're a culinary connoisseur or just enjoy entertaining, this kitchen is sure to impress. The attention to detail in this home is superb, from the Vermont-made white oak wide-plank floors to the large format Porcelanosa tile in the bathrooms. Every aspect has been meticulously designed with luxury in mind. Lighted mirrors, Kohler fixtures, and counters add an elegant touch to the bathrooms, creating a spa-like atmosphere. Step outside and experience true mountain living on the Trex wraparound back porch, complete with a covered lounge area. Imagine sipping your morning coffee or hosting memorable dinner parties while taking in the panoramic views. The front porch is equally inviting, beckoning you to relax and soak up the fresh mountain air. Inside, the floating interior stairs with glass railings provide a modern and sleek touch. The vaulted great room, loft, and open floor plan create an expansive and inviting atmosphere that is perfect for entertaining. High ceilings throughout add a sense of grandeur and sophistication to every room. Practical amenities are not forgotten in this home. Radiant heat throughout ensures your comfort on even the coldest winter days. A whole house generator provides peace of mind, knowing that you'll never be without power. Two Garages offer ample space for your vehicles and storage needs. Smart home features are seamlessly integrated into this chalet. The Sonos sound system allows you to stream your favorite music throughout the house, while Ring Cameras provide an added layer of security. The MyQ Smart Garage system allows you to control your garage doors remotely, and ADT ensures your home is protected. Don't miss this opportunity!

110 Old Road, Windham

$849,000
4 Beds 2 Baths 152702 MLS
Farmhouse Venue on Main Street Windham, greets you with a charming rocking front porch that harks back to an earlier era, year is restored for modern country living. This site offers a unique village setting complete with a post and beam barn and a large, fenced backyard. Step inside from the original covered horse and carriage hitching post, leading through elegant French doors into the main parlor. Here, you'll discover 125-year-old wide plank wood floors that have been meticulously restored, a spindle rail center staircase, original doors and genuine hardware. The inviting living room boasts a clay-fired brick fireplace with a chestnut mantle, perfect hanging holiday stockings. The country kitchen maintains its farm house charm with an authentic porcelain-fired sink nestled into quartz countertops, white subway tile backsplash, and a beverage center equipped with a wine cooler for entertaining. Enjoy your Apre' ski meals at the large dining room table surrounded by friends and family. The main floor features two bedrooms, including the primary suite concealed behind pocket doors, offering a turret sitting area, walk-in closet, and a spacious country style bathroom. The second floor accommodates two additional bedrooms, office and a center hall bathroom. Enjoy BBQ's and evening star gazing from the rear wrap deck highlighted by a new Aspen Hot tub, ideal for relaxing and viewing the ski slopes. The two-story barn offers substantial ground-level storage or the opportunity to embark on your own business venture, as Main Street offers both residential and commercial settings to open shop with great village exposure. Reach out to us today for a private tour and to explore barn restoration possibilities.

5449 Route 23, Windham

$910,000
4 Beds 4 Baths 152706 MLS
Discover serenity in this exquisite cedar contemporary home with seasonal slope views nestled in a private wooded setting, just 5 minutes from the charming resort town of Windham and a mere 2.5 hours outside of New York City. This stunning property offers a harmonious blend of rustic charm and modern amenities. Step inside to find a home that radiates warmth and sophistication. Hardwood floors and vaulted ceilings adorned in pine create an airy and inviting atmosphere, with tons of glass ensuring each room is bathed in natural light. Two cozy fireplaces further complement the ambiance. A spacious kitchen equipped with stainless steel appliances, double ovens, granite countertops, and a large breakfast bar is open to a spacious dining room with sliding glass doors that lead to an expansive deck, patio and firepit area making indoor and outdoor entertaining seamless. Four generously sized bedrooms, including two ensuite sanctuaries on the second floor, offer comfort and relaxation. The primary ensuite features a jetted tub, a fireplace, and French doors leading to a bright, flexible space that is currently used as a home office. This home is the perfect package featuring central air conditioning, a generator, a paved driveway, and an attached 2-car garage leading to a full unfinished basement. The property's landscaping is designed to enhance its woodland setting, with stone walls, walkways, and a patio blending seamlessly with the forest backdrop. 429 Mill Street isn't just a home; it's an invitation to enjoy life's simple pleasures in a setting of unmatched beauty and privacy. With its emphasis on natural landscapes, luxurious amenities, and proximity to recreational activities, it represents the ideal fusion of comfort and adventure. Schedule an in-person viewing today!

429 Mill Street, Windham

$2,775,000
9 Beds 7 Baths 152420 MLS
Step into a winter wonderland with this exclusive ski house at The Windham Mountain Club - where luxury meets adventure, right at the doorstep of the slopes. Your dream of a slopeside retreat awaits. Nestled on Windham Mountain's East side, this 6,859 square foot home exudes a perfect blend of rustic charm and modern sophistication. Its interior, wrapped in pine on walls and ceilings, radiates warmth and elegance. The great room, with its floor-to-ceiling walls of glass and a soaring 20-foot pine ceiling, magnificently brings the outdoors in, offering breathtaking mountain and ski slope views. This architectural choice ensures the space is bathed in natural light, enhancing the home's inviting atmosphere. This exquisite retreat showcases an expansive open layout that invites the splendor of the outdoors into every room. The state-of-the-art kitchen, boasting granite countertops, a breakfast bar, dual dishwashers, and a Viking range, caters to culinary enthusiasts, supported by two generous dining areas. One such area seamlessly flows to a wrap-around deck with a BBQ area, the quintessential settings for open-air dining amidst nature's backdrop.This home comfortably hosts up to 20 guests within its nine spacious bedrooms, including ensuites on both the first and second floors. The primary suite on the second floor can be closed off as a separate wing of the home, offering the utmost privacy. It serves as a sanctuary of tranquility, boasting awe-inspiring mountain vistas, his and her closet space, a fireplace, and direct access to a private balcony. Entertainment and leisure are at the heart of the home, featuring a high-end home theater with surround sound, a tremendous game room, and four inviting wood-burning fireplaces for cozy evenings after enjoying a day on the slopes. A ski enthusiast's dream, there is a dedicated ski and gear room with radiant heat. Modern conveniences such as central air conditioning, a backup generator, and a security system ensure comfort and safety throughout all seasons. Offered optionally as fully furnished (as a separate negotiation), this property stands ready to welcome you to a lifestyle of luxury in the mountains.This abode at The Windham Mountain Club is not merely a house but a sanctuary for those seeking the serenity of mountain living without forgoing convenience, amenities and luxury. Call to arrange a private tour.

150 Trailside Road, Windham

Start Your Search