About This Home

This 6-bedroom, 7-bathroom single family at 404 Winter Clove Road in Round Top, NY is listed for $1,199,000 ($145 per sqft). Built in 2000, the home offers 8,284 sqft of living space on a 6.30 acres lot.

Key Features

  • Built in 2000
  • 6.30 acre lot
  • 2 stories
  • Fireplace

Property Details

2 stories
7 full
2-car garage
2000

Amenities

FireplaceA/C
Listing Description

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 r

oom, 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.

Monthly Cost Estimate

$6,413/mo

20% down · 6.5% · 30 years

Principal$867
Interest$5,196
Insurance$350

Estimates only. Actual payments may vary.

Location

404 Winter Clove Road

Round Top, NY 12473

Features & Amenities

Interior Features

Entrance FoyerHigh CeilingsHot TubOpen FloorplanSauna

Property Details

Flooring

WoodTile - Ceramic

Construction

Frame

Outdoor Features

PatioDeck

Parking

DrivewayGarageOff Street

Heating

BaseboardHot Water(Heating)Oil

Cooling

Central Air

Appliances

Washer/DryerRefrigeratorRangeDishwasher

Questions & Answers

This 6-bedroom, 7-bathroom single family at 404 Winter Clove Road is listed at $1,199,000 ($145/sqft). The estimated monthly payment is $6,413 based on 20% down, a 30-year loan at 6.5% interest, estimated insurance.

Key features include: Built in 2000, 6.30 acre lot, 2 stories, Fireplace. Interior Features: Entrance Foyer, High Ceilings, Hot Tub.

This property is listed by Regina Tortorella.

RT

Regina Tortorella

Agent at Coldwell Banker Village Green Realty

Listed by Coldwell Banker Village Green Realty · Broker phone: 5187344200 · View on Broker Site · Broker website

MLS# 20255898· Source: Hudson Valley Catskill Region MLS· 333 days on PropertySimple

Copyright © 2026 Hudson Valley Catskill Region MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

404 Winter Clove Road, Round Top, NY 12473

Open this listing in: