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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

$1,199,000
3 Beds ⋅ 3 Baths ⋅ 154124 MLS
Discover the perfect blend of modern comfort and serene seclusion in this 2,342 sq ft, 3 bed/3 bath contemporary Cape. Located in the heart of Windham yet offering complete privacy, this home is a tranquil retreat. Renovated in 2005, it features a chef's kitchen, a comfortable living room with a wood-burning fireplace, and French doors that lead to a stone patio ideal for entertaining. The main floor also includes a library-office, an enclosed heated porch great for getting comfortable with a book and a cup of tea, and a laundry room for added convenience.Upstairs, the luxurious master suite impresses with vaulted ceilings, a Juliet balcony overlooking this mini estate, and skylights that flood the space with natural light. You'll also find the other two bedrooms and a spacious hall bath. Radiant heat beneath tile and wood floors adds comfort and style. Set on over 2.5 acres, this property is a nature lover's paradise, boasting a covered porch, landscaped grounds, and a peaceful pond for lounging and picnics.Outbuildings include "The Red House," an unfinished 2-story house currently used for storage, offers plenty of potential for transformation. The structure offers a spacious layout; it's a blank canvas ready for updates and your creativity. There is also a pool house and a smaller storage shed. My favorite is a cozy seasonal cabin, complete with electricity and a woodstove, it's a charming space for relaxation or creativity. Inside, you'll find a comfortable bed, a sitting area, and a desk perfect for a studio or quiet retreat. The inground pool, surrounded by lush greenery, provides a tranquil setting for relaxation or hosting gatherings.Just minutes from the Windham Path and the town's best restaurants. Close to skiing, golf, hiking, mountain biking, and the laid-back Catskill scene with wineries, breweries, and farm-to-table dining, this property offers a peaceful escape with endless possibilities. All this just 2.5 hours from NYC.

Windham
$180,000
154389 MLS
Welcome to Lot 79 at Windham Vista Six, where you can secure one of six premier building lots on one of Windham, NY's most sought-after country roads. This 4.72-acre parcel sits at the end of a tranquil, no-outlet road, offering unparalleled privacy and serenity. Lot 79 is shovel ready, with a formal survey and an approved septic design already in place, allowing you to begin construction without delay.The lot's topography is especially appealing, featuring a level front that gradually inclines towards the mid and back sections of the property. This natural slope is ideal for creating a house with a finished walkout basement, adding value and versatility to your future home. Enjoy a mostly wooded view with the potential for mountain vistas. If you desire more space, you have the option to purchase the adjoining Lot 80 for a combined acreage of 8.3 acres. This will not only provide additional acreage but also offer higher elevation with stunning mountain and ski slope views. Strategically positioned less than 5 minutes from the heart of Windham, this property provides convenient access to local amenities. It's also just 10 minutes away from the Windham Ski Resort, making it an ideal retreat for winter sports enthusiasts. Additionally, being only 2.5 hours from New York City makes it a convenient getaway for those seeking respite from urban life.Lot 79 offers a unique blend of seclusion, convenience, and readiness for development. Imagine your bespoke residence in this idyllic setting and seize this exceptional opportunity. Contact us today to schedule an appointment to walk this gorgeous property!

79 Begley Rd, Windham
$998,500
8 Beds ⋅ 8 Baths ⋅ 154472 MLS
Historic Inn on Main Street in downtown section of the Ski/Resort Community of Windham, NY. 7 Guest Suites plus Owners Apartment and Photo/Music/Art Studio. Well appointed and turn-key. (formerly rated #1 on Trip Advisor) Sale to settle an Estate.

5320 Ny 23, Windham
$1,300,000
3 Beds ⋅ 3 Baths ⋅ 154461 MLS
One of the most iconic pieces of Real Estate in Windham, New York is Back on the Market!! Seller Financing Available! Nestled in the Heart of Windham on bustling Main Street, this unique mixed-use property offers a blend of commercial & retail opportunity plus income generating apartments. The perfect investment that is fully rented and generating great returns that could easily carry a financing element! A community staple that houses The Main Street Market, formerly Todaro's, plus 3 additional 1 Bedroom 1 Bath Apartments upstairs. Situated on Main Street, this building benefits from high visibility and foot traffic, ideal for any retail business looking to thrive in a vibrant community setting. Whether you continue its current successes or attempt a new venture, the possibilities are endless. The ground floor features a spacious retail area, perfect for a variety of businesses. The space is designed to attract both locals and the influx of tourists Windham sees throughout the year. Above the retail space lie three spacious apartments that have been rented for years. This property presents an excellent opportunity for investors looking for dual income streams. The rental potential from both the retail and residential components ensures a steady cash flow, with the added benefit of appreciation in a sought-after location. With the right vision, there's potential for expansion or modification. The property could be an ideal candidate for those looking to add their personal touch or capitalize on Windham's growing popularity. The property being mixed-use, offers flexibility in how the space can be utilized. Have it be owner / operator and live upstairs or just rent of all 4 spaces and generate great monthly cash flow, the choice is yours. The building not only serves as a community hub but also as a cultural landmark on Main Street. This property on Main Street, Windham, is more than just a building; it's an opportunity to own a piece of a thriving small town. Whether you're looking to start or expand a business, invest in real estate, or find a unique place to call home, this property offers the best of both worlds. Contact us today to arrange a viewing and explore the possibilities this gem on Main Street has to offer. There's an additional back lot not included in the sale but can be if interested that's already subdivided as a blank canvas ready to build another retail or residential structure with access Municipal Water & Sewer!

5344 Main St., Windham
$175,000
154386 MLS
Welcome to Windham Vista Six Six exclusive building lots being offered for development just before the gates of the sought after Windmont community off of Begley Road in Windham, NY. Each lot offers unique characteristics in terms of view and topography, but all allow for secluded building envelopes that can be nestled into the forest for the utmost privacy. Lot 76 is a surveyed 5-acre building lot boasting 405 feet of road frontage, charming stone walls that extend the length of the left and rear boundary lines, potential mountain views with clearing, and secluded building envelope options throughout the property. The property's topography is mostly level for approximately two-thirds of its depth before gently sloping towards a beautiful ledge at the back. This knoll is the ideal spot for building your dream home and lends the perfect topography and setting for a future infinity pool, hot tub, and firepit site with stone walkways, and potential mountain and ski slope views (pending clearing). The seller has already drafted a private road agreement, ensuring shared maintenance responsibilities among homeowners,providing peace of mind for road upkeep. Typical costs range from a nominal $1,200 to $1,500 annually per lot/homeowner. Bring your own house plan or inquire about our preferred builder's vast portfolio of luxury home projects in Windham. Why Choose to Work with Our Preferred Builder? Working with our preferred builder means you're partnering with an expert who has a proven track record of creating luxurious communities throughout Windham. Here's what you can expect: Vast Experience: Benefit from decades of expertise in luxury home building.Inspirational Tours: Tour several new construction communities and past builds to inspire your design. Custom Design: Choose from our extensive portfolio or inspire us with your unique vision. Seamless build process from start to finish. This is an Exclusive Opportunity to become a proud owner of one of only six available lots in this exclusive offering. Your future home will be surrounded by some of the most high-end luxury homes in Windham, adding to and preserving the value of your investment. Don't miss the opportunity to create your dream oasis at Vista Six; Lot 76. Contact us today to learn more and begin your journey towards owning a piece of this exclusive, luxurious community.

76 Off Begley Rd, Windham
$319,000
2 Beds ⋅ 3 Baths ⋅ 154417 MLS
This charming townhouse offers the perfect combination of privacy and convenience, located just minutes from Windham slopes, village shops, restaurants and golf courses. Nestled at the end of a quiet drive, this 2-bedroom home, each with bath and features an additional loft area, ideal for extra sleeping space or a home office. Cozy up by the fireplace after a day on the slopes, or enjoy the serene surroundings year-round as part of a four-season community. The property benefits from reasonable HOA fees and taxes, making it an excellent choice for both seasonal getaways or full-time living. Within minutes of skiing, hiking, venues, golf, this location offers great investment and rental opportunities. Beautifully maintained . Get in before ski season and start enjoying.

76 Loo Bridge Lane Unit 12B, Windham
$699,900
3 Beds ⋅ 3 Baths ⋅ 154281 MLS
Nestled in the scenic beauty of Windham, NY, this unique octagon house offers a truly one-of-a-kind retreat close to skiing, golf, and hiking adventures. Set on over 5 acres of parklike surroundings, this property provides plenty of space for relaxation and exploration. The main home features 3 bedrooms and 2.5 baths, offering comfort and charm with stunning mountain views. The perfect country location with an animal farm just up the road to enhance the country stay.Adding even more appeal, the property includes a cozy tiny house on wheels that can be relocated to any part of the land, a whimsical tree house perfect for outdoor adventures, and spacious garages and man cave/she shed for all your storage needs. Situated on a beautiful country road, this property combines tranquility with convenience, making it an excellent investment opportunity for Airbnb enthusiasts or anyone seeking a fun full time or weekend getaway for family and friends. With its unique character and incredible setting and just a little different from the rest, this home is perfect for those looking to escape to the country

215 Siam Road, Windham
$1,200,000
4 Beds ⋅ 4 Baths ⋅ 154308 MLS
Picture Perfect Setting! Stunning Views, minutes to town and ski resort. Beautiful open concept first floor with abundance of natural light (southern exposure) greets you in this 4 bedroom, 3.5 bath mountain home. Elegant cathedral ceiling living room with impressive natural stone wood burning fireplace, with plenty of room to entertain family and friends. Kitchen with pantry/ laundry room, as well as large dining area, all facing out to gorgeous views of the surrounding mountains. (wonderful seasonal views of Windham Resort) The sliding doors to the large wrap around decking bring privacy and the beauty of nature to enjoy all year long. Spacious ensuite primary bedroom, with second wood burning fireplace, sliding doors opening to more picturesque views. The lower level offers 3 more spacious bedrooms. One is bunk room, has two sets of bunks, also offers bonus room which can be TV room, Study or extra bedroom, currently has wonderful Murphy bed. And 2 more full baths. Enjoy Windham year-round, Skiing, boarding, golf, hiking biking, fall foliage is Wonderful, also have your choice of all the great restaurants.

490 Mill Street, Windham
$29,900
154272 MLS
This 1.8-acre parcel of land is a secluded gem nestled in the woods, offering a serene escape from the hustle and bustle of everyday life. Located just 10 minutes from the charming towns of Windham and Hunter, as well as the natural retreats of CD Lane Park and Colgate Lake, this property combines both convenience and seclusion.The land is part of an original subdivision, though its precise boundaries can be challenging to determine without a survey. This could be a great opportunity for someone who values privacy and is ready for a bit of adventure in finding their own slice of nature. The area is perfect for camping or setting up an RV, providing a tranquil hideaway with a natural backdrop.Electricity is available quite a bit up the road if needed to be brought in , though this parcel itself remains off the grid, enhancing its off-the-beaten-path allure. Access to the property involves a rough, overgrown road that was once part of the original subdivision layout. This could require some effort to clear and make more accessible, but it also means you'll have a private entry to your retreat.The road is not town maintained. This is priced as an unimproved lot.In summary, this land is ideal for those looking to immerse themselves in nature while still being close to popular recreational spots. It offers the promise of solitude and adventure, with the added benefit of being near well-loved destinations for outdoor enthusiasts. Or, just a parcel to hold on to until it is eventually developed

51 White Face Mt. Trail, Windham
$1,745,000
6 Beds ⋅ 6 Baths ⋅ 153972 MLS
High Peak is an exquisite modern abode with sweeping, views of Windham High Peak and the surrounding mountains. This beautifully crafted home spans approximately 5,500 square feet across three levels. The property offers an impressive 2,000 square feet of versatile workshop, studio, and garage space, suitable for multiple uses. Sited over 3 acres, it features a tennis court, landscaped gardens, and a pond. This residence has been impeccably maintained and recently updated with a custom kitchen, central air, and ash wood flooring. .As you approach, the heated Bluestone porch and double-height entrance foyer create a striking first impression. Entering, the open-concept main floor leads to the living/family room, highlighted by a fireplace, skylights, and deck access. The natural light and panoramic views are spectacular. The kitchen and dining areas flow seamlessly from the living room, offering the perfect setting for social gatherings. Bertazzoni and Sub-Zero appliances, quartz countertops, and custom cabinetry complete the kitchen. The main floor features a half bath and office. The bespoke staircase, framed by a wall of glass, serves as an impressive architectural centerpiece.The primary suite occupies the upper floor, accessed via a sunlit landing. Upon entry, you're greeted by breathtaking views from the private lounge with fireplace. The sunken bedroom offers ample built-in wardrobe space, while the marble bathroom, complete with radiant heat, adds a touch of elegance. The upper level includes two additional bedrooms, each with ensuite bathrooms, skylights, and storage.The lower level includes two bedrooms, with access to a walkout terrace. This level also features a family room with fireplace, a sauna, shower, half bath, laundry room, wine storage, and direct access to the tennis court.Built by the current owners for year-round family living, this home is the epitome design and comfort. Selected for its prime location and amazing views, 12 Jacob Strasse Rd offers privacy while being just a 5-minute drive from the new Windham Mountain Club, restaurants, and various seasonal activities. Situated about 2.5 hours from NYC, Windham is experiencing a vibrant all-season renaissance, attracting exploding interest and investment in the area

12 Jacob Strasse Road, Windham
$279,000
2 Beds ⋅ 2 Baths ⋅ 154256 MLS
Tucked away amongst the quiet pines of the Catskill Mts. and just a stone's throw away from the vibrant village of Windham, this townhouse is a rare find. Located a short drive from Windham Mt. Club and Hunter Mt., this unit offers comfort, convenience and natural beauty. This 1 bedroom townhome includes an additional large loft and 2 full baths. Natural light from windows and skylights along with the warmth of a central fireplace create an inviting atmosphere. The main level has a pleasant entryway into the open floor plan which includes a primary bedroom, full bath, kitchen, and living room. The spiral staircase leads to a large, added loft area with a private bathroom. This area can be used as bonus sleeping space, an office, workout room, or kids' space. The possibilities are endless! The newly remodeled deck is the perfect place to relax while savoring the crisp mountain air and warm sunshine. Whether you're an outdoor enthusiast who enjoys the slopes, golfing, hiking, and biking or someone who simply wants to relax in the mountains, this townhouse offers the perfect homebase for your adventures.Don't miss out on this rare opportunity to own this 1 bedroom with additional loft in the desirable community of Windham Ridge!Unit is offered at $279,000 and is sold fully furnished.

91 Windham Ridge Road Unit 18B, Windham
$348,888
2 Beds ⋅ 2 Baths ⋅ 154190 MLS
SCORE-One of the last of the affordable townhouse/condos on the mountain top in luxurious Windham NY. Corner Unit!! With new condo prices Skyrocketing in this beautiful resort area, you can own this multilevel 2bd 2bth home w/soaring ceilings, multiple decks off both your living and bedrooms spaces, fireplace with separate level for all mechanical and storge. Short Term Rental, ski with the mountain minutes away, or in the summer swim in your own club pool, or just relax by the pool and decompress from all the stress-as you look out on the famous Catskill Mountains.Amazing Value

26 Townhouse Lane Unit 4A, Windham
$889,000
3 Beds ⋅ 3 Baths ⋅ 154092 MLS
Welcome to the Windham Round Haus located just minutes from the Windham Resort.AUnique Architectural Retreat with Renowned Interior Design by Hendley & Co.Experience the epitome of modern luxury with this architecturally stunning home, masterfully furnished and decorated by the acclaimed Hendley & Co. Located just 2.5 hours from NYC in the charming ski town of Windham, NY, this contemporary retreat is a true gem for vacation homebuyers or savvy investors. Aesthetically intriguing and vacation homebuyer or investor appealing! This gorgeously renovated contemporary with two car garage is proudly sited on 5 lush acres in the quaint little ski town of Windham, NY- just 2.5 hours outside of NYC. With over 2,800 sqft of living space, this sleek abode offers two stories of modern architecture, and an open layout complete with a circular glass great room, tremendous kitchen, three-four bedrooms and three bathrooms. From the vaulted ceilings, curved walls, and vintage wood stove to the wide spiral staircase, every inch is set to impress. The views from the glass encompassed great room will soon turn from amber fall foliage to snowflakes gently falling. The chef of the house is sure to appreciate cooking in the well- equipped kitchen that is open to the living room/entertaining spaces. The primary bedroom is separated from the other two-three bedrooms offering a peaceful sanctuary to retreat to after a long day on the slopes, enjoying the area's festivals, or any of the other various outdoor activities that the Catskills have to offer. Downstairs, loved ones will find an office with floor- to- ceiling glass, two comfortable bedrooms and one full bath that have been tastefully renovated and painted in warm earth tones. Enjoy hours of relaxing or entertaining in the home's central air conditioning, basking in the sunshine on one of two decks, or roasting marshmallows beside the fire pit. Currently established as a thriving Airbnb, this is the perfect investment property, weekend escape, or full-time residence. Timing is everything!Imagine yourself in your dream upstate property, ready to enjoy the vibrant fall colors, brisk hikes, crisp nights by the fire, and carving Windham's ski slopes fthis season! Schedule a viewing today!

407 Mill Street Street, Windham
$485,000
3 Beds ⋅ 1 Baths ⋅ 154088 MLS
Introducing a treasure in the heart of Windham, where charm and convenience beautifully coalesce. This three-bedroom oasis offers a newly renovated, low maintenance home that encapsulates comfort and serenity.Set amidst the breathtaking mountain views, this property boasts an enchanting creekside grotto. The firepit area is an idyllic spot for tranquil evenings under the stars, a feature so serene you'll forget you're in the heart of town. The harmonious sounds of the backyard creek and nearby Batavia Kill further augment this haven's tranquility.Beyond the allure of nature, the dwelling's prime location can't be ignored. Just a leisurely stroll away from the vibrant town center, you're also in close proximity to culinary delights at Babblers Restaurant and the Union & Post Restaurant. Whether you're in the mood for an intimate dinner or a lively night out, you're always minutes away from top-notch dining options.The world-renowned Windham Ski Resort is just a five-minute drive away, making this the perfect retreat for ski enthusiasts. Adventure or relaxation, this residence accommodates every whim.With potential as a rewarding second home or a lucrative investment property, this dwelling offers a plethora of possibilities. The convenience of the location, combined with the serene setting and the allure of the surrounding mountains, make this property a truly captivating find in the Windham real estate market. Embrace the chance to make it your own today.

5134 Route 23, Windham
$449,000
4 Beds ⋅ 2 Baths ⋅ 154036 MLS
Warm and welcoming old style country farmhouse. Completely renovated inside with some original touches remaining. Sizeable eat-in kitchen and living area with original fireplace. Convenient mud/laundry room off of kitchen. Sit on the new deck and enjoy beautiful wide open mountain and ski slope views. Large detached 16 x 32 out-building with sliders opening out to a 12 x 12 deck - So many possibilities with this building: attach it to the house as an addition, make a workshop and garage, office space, separate income producing apartment. Large enough to offer lots of options. This home also has a proven rental history. New roof, new furnace, new insulation, new windows, LED lighting, all within the last 2 years. It is central to everything, just a few miles to restaurants, skiing, hiking, walking paths and town.

821 Mitchell Hollow Road, Windham
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