404 Winter Clove Road

Round Top, NY
$ 1,199,000 Beds 6 Baths 7 Sq 8,284 Virtual Tour
Monthly Estimate* How much can I afford?

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.

Active

  • Price
  • $ 1,199,000
  • City
  • Round Top
  • Bedrooms
  • 6
  • Full Bathrooms
  • 7
  • County
  • Greene
  • Half Bathrooms
  • 0
  • Area
  • Cairo
  • Lot Size
  • 6.3 Acres
  • Zip
  • 12473
  • Sqr Footage
  • 8,284
  • Year Built
  • 2000
  • Taxes
  • $ 33895
  • Style
  • Contemporary
  • MLS#
  • 20255898
Listed By: Regina Tortorella with Coldwell Banker Village GreenW.
Data Source: Ulster County MLS

Features

General

Sewer Septic Tank
Heating Baseboard,Hot Water,Oil
Cooling Central Air
Roof Asphalt,Shingle
Appliances Washer/Dryer,Refrigerator,Range,Dishwasher
Zoning 01
Garage Spaces 2
Patio/Porch Features Deck,Patio
Architectural Style Contemporary
Security Features Fire Alarm,Security System
Construction Materials Frame
Year Built 2000
Electric 200+ Amp Service,Generator
View Mountain(s)
Township Cairo
Levels Two
Property Subtype Single Family Residence
County Greene
New Construction false
Property Type Residential
Attached Garage true
Garage Y/N true
Other Structures Guest House
Full Baths 7
Status Active
City Round Top
High School District Cairo-Durham Central School District
Zoning Description 500 - Rec & Entertn
MLS Area Cairo
Lot Size Units Acres
Lot Size Square Feet 274428
Tax Annual Amount 33895
MLS Area Minor Cairo
Virtual Tour https://storybookviewer.com/105923-128699
Structure Type House
Standard Status Active
Tax Assessed Value 483600
Tax Lot 12
Legal Description 135.00-2-12
New Construction false

Interior Features

Interior Amenities Entrance Foyer,High Ceilings,Hot Tub,Open Floorplan,Sauna
Basement Finished,Full,Sump Pump,Walk-Out Access,Walk-Up Access
Flooring Ceramic Tile,Wood
Fireplace Features Other
Basement (Y/N) true
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N true
Above Grade Finished Area 5884
Laundry Features Lower Level
Total Bedrooms 6
Below Grade Finished Area 2400
Total Baths 7

Exterior Features

Parking Features Garage Faces Front,On Site,Outside,Off Street,Driveway
Lot Features Back Yard,Cleared,Landscaped,Level,Meadow,Open Lot,Views
Water Source Well
Lot Size Area 6.3
Foundation Details Concrete Perimeter
Building Area Total 8284
Lot Size Acres 6.3
Road Surface Type Paved

Amenities

  • Foreclosure
  • Views
  • Short Sale
  • New Construction
  • Adult 55+
  • Lease To Own
  • No HOA Fees
  • Furnished
  • Primary On Main
  • Air Conditioning
  • Seller Finance
  • Green
  • Fixer Upper
  • Horse
  • Golf
  • Fireplace
  • Deck
  • Garage
  • Basement
  • Pool

Affordability Calculator

$3,786

Per Month

Based on the average sale price from the Delmar, NY office

  • Monthly Principal & interest $2,658
  • Monthly Property Taxes $1,062
  • Monthly Home Insurance $67
Adjust Payment Options
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Let's determine your purchasing power. Working with my mortgage partner, you'll have the information you need to shop for a home with confidence.

Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA, or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

Schools

Elementary School Unknown Elementary School
Middle School Unknown Middle School
High School Unknown High School

Price History

1/13/2026 Listed $1,350,000
8/11/2026 11% - $1,199,000

Property vs Zip Code Average in 12473

Price
AVG $240K
$1.2M
Taxes
AVG $3,616
$33,895
Year Built
AVG 1982
2000

Areas That We Cover

404 Winter Clove Road Round Top, NY is a Single Family Home for sale at $1199000 with 8284 sqft and a lot size of 6.3 Acres Acre(s). 404 Winter Clove Road Round Top has 6 bedrooms, 7 baths and was built in 2000. The property's zip code is 12473 which is in Round Top, NY

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

All information deemed reliable, but not guaranteed, and should be independently verified. The real estate information and related content displayed on this site is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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