Available Listings

$1,199,000 (USD)
Active

Cairo Area Single Family Home

Active

404 Winter Clove Road Round Top, NY 12473

6 Bed
7 Baths
8284 sqft
MLS# 20255898
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.
Listing by: Hudson Valley Catskills MLS / Listed By: Regina Tortorella, Coldwell Banker Village Green Realty
$1,199,000 (USD)
Active

Prattsville Area Single Family Home

Active

172 Hank Oliver Prattsville, NY 12468

3 Bed
3 Baths
3400 sqft
MLS# 20261626
Build your Catskills dream home on 10 private acres with panoramic mountain views while working alongside local builder Richard Tait of Tait Construction, bringing 30 years of experience and an extensive portfolio of quality homes to your project. From site work through final finishes, the entire process is professionally managed.

The proposed 3,400 sq ft modern farmhouse features open-concept living and an impressive 640 sq ft wraparound porch designed to capture the surrounding countryside and mountain views. Buyers who get involved early have the opportunity to customize the design, floor plan preferences and finishes, working alongside the builder/developer from the beginning through the finishing details.

Set on a quiet, no-outlet country road surrounded by rolling farmland and pristine countryside, the 10-acre homesite offers privacy, open skies and sweeping Catskill views. Road access, electric, proposed well, septic design and site preparation help streamline the path to construction. Optional enhancements include a 22KW generator, spring water connection, underground electric, private pond and steel roof.

For those dreaming bigger, an additional 14+ acres directly across the road is available, featuring rolling open acreage, a scenic stream and 6-stall horse barn--ideal for equestrian use, recreation or creating a larger Catskills estate. Ask the listing agent for additional acreage and barn pricing.

Convenient to Windham, Hunter and Belleayre Mountains, yet tucked away in the beautiful Western Catskills countryside.

Get in early, make it your own, and build with confidence from the ground up.
Listing by: Hudson Valley Catskills MLS / Listed By: Lisa Jaeger, Coldwell Banker Village Green Realty
$1,199,000 (USD)
Active

Windham Area Single Family Home

Active

78 Buckskin Windham, NY 12496

4 Bed
4 Baths
3977 sqft
MLS# 20261997
Welcome to Windmont--Windham's most exclusive gated community--where luxury living meets the serenity of a private, thousand-acre natural preserve. Opportunities to own here are few and far between, making this a truly rare offering.

Enter through secured gates and follow a scenic road to a paved, winding driveway that leads to this beautifully updated contemporary home, privately sited on 5 acres and bordering over 1,000 acres of protected state and city land, delivering unmatched privacy, natural beauty, and direct access to trails right from your backyard.

Step inside to a tiled foyer with a stunning wide, curved staircase and soaring ceilings, setting the tone for the home's elegant design. The residence is drenched in natural light throughout its 4,000 sq ft of living space, highlighted by gleaming wood floors and an open, airy layout.

The main living spaces are designed to impress, featuring a dramatic great room with vaulted ceilings, exposed beams, a wood-burning fireplace, and a built-in wet bar--perfect for après-ski gatherings. From here, step out onto one of two expansive decks, including a brand-new deck with a new hot tub, all overlooking a peaceful, private yard. A secondary living room provides additional space to relax or entertain.

The kitchen is both stylish and functional, offering stainless steel appliances, granite countertops, and seamless flow into a formal dining room through elegant French doors.

With four bedrooms plus a generous flex room currently used as a fifth bedroom, there's room for everyone. The first-floor primary en-suite is a retreat of its own, featuring dual walk-in closets and a jetted soaking tub surrounded by windows with tranquil views of the outdoor firepit. **Included in the bedroom count are two en-suites--one on the first floor and one on the second--**providing comfort and privacy for both owners and guests.

Architectural details such as arched doorways and multiple access points to the expansive decks enhance the home's charm, while seasonal ski slope views peek through the trees--reminding you just how close you are to the action.

A mud/ski room and attached three-car garage make mountain living effortless, while recent upgrades--including a new roof, new deck and hot tub, freshly painted exterior, a water filtration system, generator, a newer a Buderus furnace (installed in 2022), new water pump, and a newly installed sewer riser for easier access to the septic system--ensure peace of mind. The home is equipped with a newer Buderus G215/6 (256K BTU) furnace, regularly serviced with its most recent service completed in December 2025. A Eufy security system is included in the sale, and high-speed fiber optic internet through Mid-Hudson Cable provides seamless connectivity for both work and leisure.

Located just minutes to Windham Mountain Club, local golf courses, and the town's restaurants and shops, this property offers the perfect balance of privacy, luxury, and convenience--all just 2.5 hours from NYC.
Listing by: Hudson Valley Catskills MLS / Listed By: Regina Tortorella, Coldwell Banker Village Green Realty
$1,198,000 (USD)
Active

New Paltz Area Single Family Home

Active

227 Mountain Rest New Paltz, NY 12561

3 Bed
3 Baths
2712 sqft
MLS# 20265446
RARE OFFERING ADJACENT TO THE MOHONK PRESERVE! A beautiful, ecologically intended home surrounded by native gardens is tucked away on a winding wooded driveway off Mountain Rest Road, on top of the Shawangunk Ridge, a stone's throw from the Mohonk Mountain House entrance. Hike/mountain bike OUT YOUR DOOR onto protected land and easily access Bonticou Crag and other carriage paths and trails laced through the Mohonk Preserve. (with membership of course!)
The home was thoughtfully renovated over the years to bring the magic of the natural world outside ...inside! One enters through a cedar covered porch into an expansive, open-concept living room, kitchen, and dining room that creates a fluid, airy heart of the home, bathed in natural light, completely blurring the line between indoor comfort and the natural world. This stunning open space flows directly out onto a huge two-level deck, featuring a pergola and greenhouse, offering the perfect platform for entertaining, relaxing, and taking in the panoramic views of your self-sustaining ecosystem. A large hot tub is perfect for evening star-gazing. Two bedrooms are on the main floor and the third is on the lower level in addition to an office space that has its own exterior entrance for a possible home business. (One of the current owners has an at-home chiropractic office.) The third bedroom on the lower level also has it's own ingress/egress and could be a 2nd office. There are three full bathrooms and one even has a sauna! There is a highly functional laundry room with dedicated space for the washer, dryer, chest freezer, and utility sink. There is also an exercise room off the lower garage entrance. This home combines modern living with exceptional energy efficiency, significantly reducing your monthly utility bills. The attic features premium spray foam insulation directly under the roofline, creating a tightly sealed thermal envelope that helps keep the house comfortable year-round. Heating and cooling are powered by a highly efficient multi-zone heat pump system, allowing for precise temperature control in different areas of the house. The garage features an installed EV car charger. Best of all, extensive solar panel arrays span across two optimal roof surfaces, harnessing maximum sunlight to generate clean, renewable electricity and offset your energy bills.
A decade ago, this property was a blank canvas and over the years the owners have intentionally transformed the nearly 4 acres, with a deep respect for the local ecosystem. Many of the invasive plants have been removed and, in their place, they have planted a vibrant tapestry of Hudson Valley native plants; inviting back the local birds, pollinators, and wildlife. This ecological commitment shines through in the eco-conscious landscaping choices, including the planting of sustainable ''no mow'' grass and the addition of a gorgeous, planted meadow featuring vibrant lupines and echinacea. The outdoor space features gardens and foraging highlights: 5 distinct specialized gardens all secured by professional deer fencing: the Vegetable Garden, the Arboretum, the Evergreen Area, the East Garden Tree Nursery, and a large Permaculture area in addition to an active sugar bush that generates gallons of maple syrup each year. Enjoy a sustainable, future-ready lifestyle without sacrificing comfort. Amenities are very close by in New Paltz and Poughkeepsie on the Hudson side of the Shawangunk Ridge, as well as High Falls/Stone Ridge on the Catskill side. The Thruway exit is minutes away. For the next owner, this property offers a rare chance to be the next caretaker of a beautiful, well thought-out turnkey homestead that will offer them a deeply peaceful sanctuary and an ability to access over 8,000 protected acres.
**************OPEN HOUSE******************
Saturday October 10th 1:OO-4:OO
Listing by: Hudson Valley Catskills MLS / Listed By: Anne "Hilton" Purvis, Coldwell Banker Village Green Realty
$1,195,000 (USD)
Active

Bearsville Area Single Family Home

Active

388-390 Wittenberg Road Bearsville, NY 12409

5 Bed
4 Baths
3475 sqft
MLS# 1016096
Virtual Tour
A rare opportunity just minutes from the heart of historic Woodstock, this exceptional country compound pairs the timeless character of a beautifully updated farmhouse with the privacy and tranquility of an estate-like setting. A long private drive unfolds through peaceful, park-like grounds where meadow, mature woods, gardens, and abundant nature create a remarkable sense of seclusion so close to town. At the center of it all, the classic farmhouse has been thoughtfully transformed for modern living while preserving the warmth and authenticity that make a Woodstock home so distinctive. An expansive wraparound porch and deck invite long afternoons outdoors, elegant entertaining, and evenings beneath the stars from the hot tub. Inside, natural light pours through generous windows and skylights, illuminating an open and welcoming interior where a spacious living room flows effortlessly into the dining area and striking gourmet kitchen, anchored by a dramatic stone island. A soaring vaulted family room overlooks the meadow and woods and features a woodstove and direct access to the deck, creating an extraordinary gathering space—or the possibility of a main-level primary suite. A separate den offers an ideal home office or studio, while a gym/yoga room, laundry room and full bath add versatility to the first floor. Upstairs, three bedrooms and another full bath retain the farmhouse's old-world charm, including a serene and generously proportioned primary bedroom and a second bedroom with its own inviting nook.
Adding another dimension to this extraordinary property is a beautifully maintained storybook cottage, privately positioned toward the front of the grounds with its own parking, patio, and yard. Currently licensed for Airbnb use, the cottage offers an appealing opportunity for short-term rental income while remaining equally suited as an elegant guesthouse, private retreat, or longer-term residence. Its charming two-story interior features a comfortable living room, eat-in kitchen, full bath, and two upstairs bedrooms, creating a completely independent destination within the property. With hiking, nature preserves, and the Catskills landscape nearby—and the galleries, restaurants, shops, music, and cultural life of Woodstock only a few miles away—this is a particularly rare convergence of location, privacy, architectural character, and flexibility. Whether envisioned as a refined full-time residence, an exceptional weekend escape, or a private country compound with a valuable guest and rental component, this turnkey property captures the essence of elevated Woodstock living: a classic farmhouse reimagined for today, surrounded by natural beauty, with space to retreat, gather, entertain, and simply enjoy an extraordinary place to call home.
A 3D Walkthrough Tour is available in the digital Lookbook or by request.
Listing by: ONEKEY as distributed by MLS GRID / Listed By: Eric Amaral, Coldwell Banker Village Green Realty
$1,195,000 (USD)
Active

Woodstock Area Single Family Home

Active

388-390 Wittenberg Bearsville, NY 12409

5 Bed
4 Baths
3475 sqft
MLS# 20265618
A rare opportunity just minutes from the heart of historic Woodstock, this exceptional country compound pairs the timeless character of a beautifully updated farmhouse with the privacy and tranquility of an estate-like setting. A long private drive unfolds through peaceful, park-like grounds where meadow, mature woods, gardens, and abundant nature create a remarkable sense of seclusion so close to town. At the center of it all, the classic farmhouse has been thoughtfully transformed for modern living while preserving the warmth and authenticity that make a Woodstock home so distinctive. An expansive wraparound porch and deck invite long afternoons outdoors, elegant entertaining, and evenings beneath the stars from the hot tub. Inside, natural light pours through generous windows and skylights, illuminating an open and welcoming interior where a spacious living room flows effortlessly into the dining area and striking gourmet kitchen, anchored by a dramatic stone island. A soaring vaulted living room overlooks the meadow and woods and features a woodstove and direct access to the deck, creating an extraordinary gathering space - or the possibility of a main-level primary suite. A separate den offers an ideal home office or studio, while a gym/yoga room, laundry room and full bath add versatility to the first floor. Upstairs, three bedrooms and another full bath retain the farmhouse's old-world charm, including a serene and generously proportioned primary bedroom and a second bedroom with its own inviting nook.
Adding another dimension to this extraordinary property is a beautifully maintained storybook cottage, privately positioned toward the front of the grounds with its own parking, patio, and yard. Currently licensed for Airbnb use, the cottage offers an appealing opportunity for short-term rental income while remaining equally suited as an elegant guesthouse, private retreat, or longer-term residence. Its charming two-story interior features a comfortable living room, eat-in kitchen, full bath, and two upstairs bedrooms, creating a completely independent destination within the property. With hiking, nature preserves, and the Catskills landscape nearby - and the galleries, restaurants, shops, music, and cultural life of Woodstock only a few miles away - this is a particularly rare convergence of location, privacy, architectural character, and flexibility. Whether envisioned as a refined full-time residence, an exceptional weekend escape, or a private country compound with a valuable guest and rental component, this turnkey property captures the essence of elevated Woodstock living: a classic farmhouse reimagined for today, surrounded by natural beauty, with space to retreat, gather, entertain, and simply enjoy an extraordinary place to call home.
A 3D Walkthrough Tour is available in the digital Lookbook or by request.
Listing by: Hudson Valley Catskills MLS / Listed By: Eric Amaral, Coldwell Banker Village Green Realty
$1,150,000 (USD)
Active

Saugerties Area Single Family Home

Active

382 Band Camp Road Saugerties, NY 12477

4 Bed
3 Baths
2112 sqft
MLS# 1050958
Virtual Tour
Charming Antique Home & Private Catskill Mountain Retreat! Welcome to this charming antique home nestled on over three private acres between Woodstock and Saugerties, offering the perfect blend of historic character, modern updates, and year-round Catskill Mountain living. This beautifully remodeled 4-bedroom, 2.5-bath home has been thoughtfully updated, while preserving its original charm. Nearly every major system has been improved, including heating and cooling, septic, electric, and solar panels, providing modern comfort and peace of mind. Step outside and discover your own private backyard oasis, featuring a fenced-in, heated saltwater inground pool and a brand-new hot tub -- perfect for relaxing, entertaining, and enjoying long summer days. A separate studio offers additional space of 640 square feet, for guests, a home office, creative pursuits, or a private retreat. The location is ideal for enjoying everything the Catskill Mountains and Hudson River Valley have to offer. You're conveniently situated between the vibrant communities of Woodstock and Saugerties, with easy access to acclaimed cultural destinations including the Woodstock Playhouse, Bearsville Theater, and Orpheum Theater, as well as hiking, biking, skiing, swimming, dining, music, and countless other year-round activities. Whether you're looking for a full-time residence, weekend escape, or private Catskills retreat, this special property offers character, comfort, modern infrastructure, and an exceptional outdoor lifestyle -- all in one truly inviting setting. There is so much more to discover here. Come experience this unique Catskill Mountain property for yourself. The property is currently being used as a very successful Airbnb.
Listing by: ONEKEY as distributed by MLS GRID / Listed By: Sara Gorman Maliha, Coldwell Banker Village Green Realty
$1,150,000 (USD)
Active

Saugerties Area Single Family Home

Active

382 Band Camp Saugerties, NY 12477

4 Bed
3 Baths
2112 sqft
MLS# 20265460
OPEN HOUSE SATURDAY 10/24/26...11 TO 1PM....Charming Antique Home & Private Catskill Mountain Retreat! Welcome to this charming antique home nestled on over three private acres between Woodstock and Saugerties, offering the perfect blend of historic character, modern updates, and year-round Catskill Mountain living. This beautifully remodeled 4-bedroom, 2.5-bath home has been thoughtfully updated, while preserving its original charm. Nearly every major system has been improved, including heating and cooling, septic, electric, and solar panels, providing modern comfort and peace of mind. Step outside and discover your own private backyard oasis, featuring a fenced-in, heated saltwater inground pool and a brand-new hot tub -- perfect for relaxing, entertaining, and enjoying long summer days. A separate studio offers additional space of 640 square feet, for guests, a home office, creative pursuits, or a private retreat. The location is ideal for enjoying everything the Catskill Mountains and Hudson River Valley have to offer. You're conveniently situated between the vibrant communities of Woodstock and Saugerties, with easy access to acclaimed cultural destinations including the Woodstock Playhouse, Bearsville Theater, and Orpheum Theater, as well as hiking, biking, skiing, swimming, dining, music, and countless other year-round activities. Whether you're looking for a full-time residence, weekend escape, or private Catskills retreat, this special property offers character, comfort, modern infrastructure, and an exceptional outdoor lifestyle -- all in one truly inviting setting. There is so much more to discover here. Come experience this unique Catskill Mountain property for yourself. The property is currently being used as a very successful Airbnb.
Listing by: Hudson Valley Catskills MLS / Listed By: Sara Gorman Maliha, Coldwell Banker Village Green Realty
$1,149,000 (USD)
Active

Windham Area Single Family Home

Active

292 #3 South Windham, NY 12496

5 Bed
6 Baths
3643 sqft
MLS# 20254832
Luxury STR Investment Opportunity Across from Windham Mountain Club -- turnkey option, income-producing, and Owner Financing available with as little as 20 pct down- perfectly positioned in one of the Catskills' most desirable four-season destinations.

Located within walking distance to Windham's restaurants, shops, nightlife, and ''The Valley,'' Windham Mountain Club's exciting new expansion featuring pools, tennis, pickleball, spa amenities, golf, and more, this luxury townhouse delivers the ultimate combination of lifestyle and investment potential.

This proven Airbnb/Vrbo-friendly property offers the option to be sold fully furnished and can include transferable future bookings already secured for upcoming ski seasons--allowing the new owner to generate immediate rental income from day one.

A rare opportunity for investors seeking a high-demand short-term rental in a prime resort location with exceptional year-round appeal.

Inside, the home features an open-concept design ideal for entertaining, a chef's kitchen with granite countertops and stainless-steel appliances, a spacious great room with fireplace, central air conditioning, heated garage, multiple en-suite bedrooms, and a large deck with beautiful mountain and ski slope views. Just steps from shuttle access and minutes to skiing, hiking, golf, spas, and dining, this is the perfect Catskills getaway, second home, or high-performing investment property only 2.5 hours from NYC.

Option to purchase furnished. Future bookings may be transferred at closing if the purchaser wishes. Immediate ROI potential in the heart of Windham.

Schedule an in-person viewing today!
Listing by: Hudson Valley Catskills MLS / Listed By: Regina Tortorella, Coldwell Banker Village Green Realty