Windham, NY Homes under $500,000

Discover the perfect blend of charm, space, and convenience in this beautiful 4-bedroom, 2-bathroom countryside home, ideally located less than 3 hours from NYC. Set on scenic land in historic Windham NY. This vibrant small town is surrounded by renowned ski resorts; this is the ideal getaway or year-round residence.An exceptionally inviting home that is perfect for guests or extended family,

Brian Cohen RHR Realty Group

Charming 4-Bedroom Ranch on 1.6 Acres in Windham, NYDiscover your dream retreat in the heart of the Catskills! Nestled in the picturesque village of Windham, just minutes from vibrant downtown and the renowned Windham Mountain Resort with its array of restaurants and shops, this spacious 4-bedroom, 2-bathroom ranch offers the perfect blend of comfort and charm.Situated on a

Fred Mazza Bunce Realty

Perched above the road on a private and wooded1.50 acres, opposite the Windham Path, sits this thoughtfully renovated 3 bedroom, 2.5 bath . this home is ready for you to enjoy year round! The bright and airy professional kitchen offers GE Cafe appliances 8-9 years old,, striking granite counters and island. The generous dining area affords plenty of room for family and friends. Enjoy lush green

Irene Pinto Brainard Ridge Management

Great opportunity to own a vacation home in Windham! Lots of room for loved ones & guests.Featuring 5 bedrooms, 2 1/2 baths, open floor plan, and wood burning fireplace. Property has a pond.Conveniently located to Elm Ridge Club which has tennis courts, swimming pool & recreation room.Windham Mountain Club is minutes away.

Sheila Word Coldwell Banker Village Green

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

Jason Dugo Dugo Realty

Brainard Ridge Charmer!Ready for 4 season active life style. Charming 3 bedroom, 2 bath plus extra sleeping alcove, Brainard Ridge Townhome. Open and airy floor plan, lots of natural light! Cozy living room with large wood burning fireplace, nice dining area, cheery kitchen, Primary bedroom with ensuite bath, plus extra sleeping alcove. Lower level with bunkroom, and guest bedroom, second full

Patricia Charbonneau Brainard Ridge Management

Walk to the Windham Path from this newly renovated two story home. Offered fully furnished, stocked with everything you need to greet your next guest, this active Airbnb is ready for the next owner. Two first floor bedrooms each with their own beautifully new tiled bath. New kitchen with butcher block counter tops, new appliances with induction stove. Upstairs 2 more bedroom with its own half

Cynthia Welch Welch Realty Inc.

Just a stones throw from the slopes at Windham Mountain, you will find this gem. A 5 bedroom, 3 bathroom village home that has been fully renovated while maintaining much of the original character. The exterior boasts a rocking chair porch, abundant space for entertaining or enjoying, extensive garden area, hot tub, orchard(apples and pears), hiking, bird watching, and so much more! The turn-key

Jessica Surbeck WINDSTAR REALTY GROUP LLC

Charming 3-Bedroom Retreat in Serene Wooded SettingNestled on a private road in a tranquil wooded haven, this newly renovated 3-bedroom, 2-bath retreat seamlessly blends modern comforts with cozy charm. Perfect as a primary residence, vacation home, or income-generating AirB&B, this property offers exceptional versatility and appeal.Key Features:Upper Level: Spacious

Fred Mazza Bunce Realty

Whether your search is for personal use or investment property, this Windham Farmhouse, just steps from the center of town, offers versatility and plenty of room for the whole family. A unique three floor layout allows for everyone to have their own space. The first and lowest level is the main living area: Kitchen, Dining, Living Room as well as a bedroom and full bath. The sunroom is an added

Sharri Cunningham Bunce Realty

Charming 4-Bedroom Townhome Just Minutes from Windham Slopes!Discover this beautifully designed townhome in a vibrant four-season community, just five minutes from Windham's premier ski slopes, golf courses, scenic walking paths, top-rated restaurants, and stunning hiking trails. This thoughtfully crafted three-level home offers:4 Spacious Bedrooms + Bonus Room - Plenty of space for family and

John Pumilia Shaw Country Realty, Inc.

Dreaming of a quick escape from NYC's chaos? Just 2.5 hours from the city, nestled in the heart of the Catskill Mountains, lies this breathtaking 4-bedroom, 3.5-bath townhouse with access to a community pool and shuttle service to and from the Windham Mountain Resort. This spacious three-story townhouse seamlessly blends comfort and adventure. With an open concept floor plan, vaulted ceilings,

Regina Tortorella Coldwell Banker Village GreenW