luxury houses with pool for sale Windham, United States

Discover a rare Catskills retreat in Round Top, NY, offering 6.3 peaceful acres with open land, wooded edges, and sweeping mountain views. Ideal as a weekend escape or full-time residence, this property includes two beautiful homes, modern amenities, and nearby access to trails, waterfalls, and local dining. It blends total privacy with a prime location close to Hudson, Woodstock, ski resorts, and year-round recreation.The main home is a striking 6,748 sq ft postmodern chalet (including the finished basement) filled with natural light and designed for comfort, creativity, and entertaining. Its dramatic centerpiece is a 2,500 sq ft great room with soaring ceilings and exceptional acoustics—a space once used by opera performers and perfect for gatherings, celebrations, music, or quiet relaxation. With six bedrooms, seven bathrooms, central A/C, and an attached two-car garage, the home delivers spacious living with modern convenience. Zoning for residential and entertainment use offers added flexibility for hosting events or retreats.The residence is equipped with a whole-house generator, security system, and direct-to-station fire alarm, providing peace of mind. The finished basement adds more than 2,000 sq ft of flexible living space, including a sauna, bathrooms, a laundry room, a large flex room suitable for a gym, studio, or recreation area, plus generous storage and a separate entrance that expands layout options even further.Outdoor living is a defining feature. An deck and patio with hot tub beside them, showcases beautiful mountain views, creating a resort-like experience year-round. Below, a stone patio and fire pit offer additional space for relaxing and entertaining. Thoughtful landscaping enhances curb appeal while maintaining a low-maintenance, natural look.A second home, a charming Cape-style guest house, adds significant versatility. With three bedrooms, two bathrooms, and an open kitchen-living layout, it's ideal for multi-generational living, rental potential, private guest accommodations, or a dedicated creative retreat. The dual-home setup makes the property especially attractive for buyers seeking space, privacy, and flexibility.The location elevates the entire lifestyle. A bike trail directly behind the property leads to waterfalls, swimming holes, and wooded stretches perfect for hiking and biking. Round Top restaurants are close enough to walk to, offering convenience with small-town charm. Golfers will appreciate being only minutes from Blackhead Mountain's scenic course, while skiers can reach Hunter and Windham Resorts in about thirty minutes. Nearby towns like Hudson, Ashland, and Woodstock add arts, dining, and culture to your orbit, making this a true four-season destination.Whether you're seeking a private mountain retreat, a luxurious weekend getaway, or a spacious home with room for guests and gatherings, this property stands out as a rare Catskills offering. With two homes, stunning mountain views, extensive indoor-outdoor living spaces, and a prime location near top attractions, this estate delivers a lifestyle of relaxation, beauty, and possibility.A 3D Walkthrough Tour is available in the digital Lookbook or by request.

The Clove House in Elka Park- There are places in the Catskills where the journey is every bit as beautiful as the destination. 1958 Platte Clove Road is one of them. Set on just over two acres in Elka Park, this four-bedroom, three-bath mountain retreat sits amid one of the Catskills' most dramatic landscapes--where winding mountain roads climb past waterfalls, deep forest and rocky cloves, and miles of celebrated hiking trails are just moments away. Inside, the house is designed for relaxed four-season living. A woodstove sets the tone after a day on the mountain, while the lower-level recreation space--with ping-pong and Pop-A-Shot--offers plenty of room for gathering and play. An attached one-car garage adds everyday practicality. Out back, a generous deck looks toward the surrounding mountains and creates the perfect perch for morning coffee, summer dinners and long autumn afternoons. A swim spa adds another layer of four-season enjoyment-equally inviting for a refreshing summer dip or a warm soak after a day of hiking or sking. A separate ADU adds another layer of possibility--ideal as a studio, office, creative retreat or additional flexible space. Close to Platte Clove Preserve, Plattekill Falls, Huckleberry Point and some of the Catskills' most extraordinary hiking, 1958 Platte Clove Road is more than a mountain house. It's a front-row seat to the Catskills!

Legacy estate built into a hillside at 2,400 feet above sea level with far-reaching mountain views, Sul Monte is a of rare architectural pedigree and natural beauty. Commissioned in 1921 by opera legend Amelita Galli-Curci and designed by Harrie Thomas Lindeberg, one of the most respected country house architects of the 20th century, the home blends European country house traditions with an American sense of scale and ease. The result is a residence both gracious and grounded, expressive in form yet timeless in spirit. Set on 61 acres of terraced lawns, wildflower meadows, specimen trees, and woodlands with walking trails, the property offers sweeping views across the Catskills. Its half-timbered facade, leaded glass windows, and sculpted cedar shake roof evoke the romance of the English countryside, while interiors reveal over 8,200 square feet designed for both entertaining and private living. Enter through the porte cochere into an all-season mudroom leading to the spacious eat-in kitchen and adjacent breakfast room. From here, a generous butler's pantry, complete with original cabinetry, a vintage warming cabinet, and a zinc-clad sink, connects to both the informal dining room with leaded glass and stone floors and the formal dining room with beamed ceilings, fireplace, and a built-in bar concealed behind paneled doors. At the heart of the home, the living room blends comfort, character, and versatility. A wall of built-in bookcases displays books and personal collections, while a deluxe billiards table anchors the space beneath its original pendant light. A cozy seating area centers around the carved mantel bearing Galli-Curci's initials flanked by foxes, an enduring nod to Sul Monte's storied past. With leaded glass windows, wide-plank floors, and period details throughout, the room invites both lively gatherings and quiet evenings at home. Just beyond, a sunroom perfectly frames Catskill Mountain views and offers an inviting spot for a morning read or evening aperitif. Monumental windows framed in stone flood the great room with natural light, accentuating its soaring ceilings and exposed timber trusses. Originally Galli-Curci's private rehearsal studio, the space now serves as a magnificent setting for music, gatherings, or peaceful downtime. Its scale, light, and craftsmanship give the great room a presence that's both impressive and inviting. Up a private staircase from the great room, the primary suite is rich in character, with a barrel-vaulted ceiling, diamond-paned windows, and a deep window seat perfectly poised for taking in the grounds and views beyond. The suite includes a dressing room lined with mirrored closet doors and an en suite bath with original tilework and fixtures, positioned to capture western sunset light. Five additional bedrooms are gracious and well-proportioned, four of which feature finely crafted built-in closets. All six of the home's bathrooms retain original 1920s porcelain fixtures. Tucked into a beautifully landscaped corner of the grounds, the saline, heated pool also enjoys expansive views and offers a tranquil escape just a short stroll across the lawn from the house, ideal for a morning swim, a relaxed afternoon, or gathering with friends at sunset. Other features include an indoor sauna, expansive flagstone terrace, a small barn, a charming shed, and a four-room studio space with a bathroom and kitchen above the garage, currently used as a potter's studio, with potential for guest or staff accommodations with additional improvements. Located minutes from Belleayre Mountain Ski Resort and the hamlets of Phoenicia, Margaretville, and Fleischmanns, Sul Monte is just 2.5 hours from NYC and within easy reach of Woodstock and other Hudson Valley destinations. More than a residence, Sul Monte is a piece of architectural heritage, shaped by Lindeberg's belief that great homes are meant not just to endure, but to be lived in fully and shared generously.

Architect-Designed Modern Retreat with Unparalleled Views Over Woodstock! Perched high above the Town of Woodstock, this rare and exceptional home offers a front-row seat to breathtaking panoramic views that stretch from the mountains to the Ashokan Reservoir. Designed by noted architect Les Walker, this contemporary residence evokes the magic of living in a luxurious treehouse--where every room is immersed in natural light and dramatic scenery. Wake to stunning sunrises and unwind to radiant sunsets from the comfort of your open floor plan living space, where a soaring floor-to-ceiling bluestone fireplace anchors the heart of the home. Expansive windows line the entire south-facing rear of the house, bringing the outdoors in and framing unforgettable vistas year-round. Enjoy seamless indoor-outdoor living with two spacious decks--one screened for breezy summer nights, and one open for sun-soaked afternoons. The chef's kitchen flows effortlessly into the main living area, ideal for entertaining or quiet evenings by the fire. The main floor primary ensuite features a walk-in closet, built-in shelving, and serene views, while two flexible-use rooms offer space for a home office, media room, or guest quarters. Smart thermostats add modern comfort. Step outside to your private bluestone patio with a heated saline inground pool, outdoor kitchen, and firepit--your personal oasis nestled in the Catskills. A finished studio space above the 440 sq. ft. garage offers even more options for creativity or guests. Additional features include solar panels with battery pack, a circular drive for easy access, and meticulous attention to detail throughout. A truly rare offering--private, peaceful, and just minutes to the vibrant arts, dining, and community of Woodstock. A 3D Walkthrough Tour is available in the digital Lookbook or by request.