404 Winter Clove Rd

Round Top, NY 12473

$1,350,000
Price
6
Beds
8,284 Sq. Ft.
$163 / Sq. Ft.
8,284
Sq. Ft.
$163
per Sq. Ft.
Virtual Tour
Virtual Tour
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a kitchen with stainless steel appliances granite countertop a refrigerator and a sink
a kitchen with stainless steel appliances granite countertop a refrigerator and a stove top oven
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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...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.
  1. Listed by Regina Tortorella • Coldwell Banker Village GreenW
    P: (914)-466-0329 C: (914)-466-0329 secondhomeguru@gmail.com
  2. Listed by Aaron Perer • Coldwell Banker Village GreenW
    P: (518)-734-4200 aaronperer.realestate@gmail.com

Property Details for 404 Winter Clove Road

Zoning
01
Zoning Description
500 - Rec & Entertn
Basement YN
Yes
LISTING UPDATED: 12/03/2025 01:42 PM

Property Details for 404 Winter Clove Road

StatusActive
MLS #20255898
Days on Market29
Taxes$33,895 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built2000
Lot Size6.30 AC / 274,428 SF
CountyGreene County

Location

Listing Courtesy of Coldwell Banker Village GreenW
Add your commute

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Building Information for 404 Winter Clove Road

Stories-Year Built2000Building Size-Lot Size6.30 AC / 274,428 SF

Payment Calculator

$9,495 per month

30 year fixed, 6.28% Interest

Principal and Interest

$6,671

Property Taxes

$2,825

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 404 Winter Clove Road

Summary
Location and General Information
  • Directions: NY Thruway to Cairo. Head south on Main St, right on Mountainview. Go 2 mi, stay left onto Rt 39. After 1.3 mi left on Hearts Content Rd, then right on Winter Clove Rd; house is 1/4 mi on right.
  • Township: Cairo
  • MLS Area Major: Cairo
  • County: Greene
  • Latitude: 42.247788
  • Longitude: -74.030126
  • MLS Area Major: Cairo
  • Sign On Property YN: No
  • Mountain(s): Yes
Taxes and HOA
  • Association Fee: $.00
  • Parcel Number: 135.00-2-12
  • Tax Block: 2
  • Tax Legal Description: 135.00-2-12
  • Tax Annual Amount: $33,895.00
Parking
  • Attached Garage YN: Yes
  • Garage YN: Yes
  • Garage Spaces: 2.0
  • Garage YN: Yes
  • Attached Garage YN: Yes
  • Garage Spaces: 2.0
  • Driveway: Yes
  • Garage Faces Front: Yes
  • Off Street: Yes
  • On Site: Yes
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Property
Lot Information
  • New Construction YN: No
  • Lot Size Acres: 6.3
  • Above Grade Finished Area: 5884.0
  • Below Grade Finished Area: 2400.0
  • Living Area: 8284.0
  • Lot Size Area: 6.3
  • Lot Size Units: Acres
  • Lot Size Square Feet: 274428.0
  • Above Grade Finished Area: 5884.0
  • Below Grade Finished Area: 2400.0
  • Lot Size Acres: 6.3
  • Contemporary: Yes
  • Frame: Yes
  • Cleared: Yes
  • Landscaped: Yes
  • Level: Yes
  • Meadow: Yes
  • Open Lot: Yes
  • Views: Yes
  • House: Yes
Property and Assessments
  • Owner Name: Jonathan Barriga
  • Total Floor Plans Count: 0
  • Property Type: Residential,Single Family Residence
  • Year Built: 2000
  • Property Sub Type: Single Family Residence
  • New Construction YN: No
  • Page: 3003
  • Section: 135.00
Taxes and HOA
  • Tax Assessed Value: 483600.0
  • Tax Lot: 12
Utilities
  • Generator: Yes
  • Septic Tank: Yes
  • Well: Yes
Interior and Exterior Features
Exterior Features
  • Guest House: Yes
  • Patio: Yes
  • Shingle: Yes
  • Fire Alarm: Yes
  • Security System: Yes
Interior Features
  • Basement YN: Yes
  • Fireplaces Total: 0
  • Fireplace YN: Yes
  • Room Total: 0
  • Bathrooms Total (Integer): 7
  • Bathrooms Total (Decimal): 7.0
  • Bathrooms Total (Notational): 7.0
  • Cooling: Yes
  • Heating: Yes
  • Bedrooms Total: 6
  • Bathrooms Full: 7
  • Bathrooms Half: 0
  • Bathrooms Half: 0.0
  • Fireplace YN: Yes
  • Dishwasher: Yes
  • Range: Yes
  • Refrigerator: Yes
  • Finished: Yes
  • Full: Yes
  • Sump Pump: Yes
  • Walk-Out Access: Yes
  • Walk-Up Access: Yes
  • Central Air: Yes
  • Ceramic Tile: Yes
  • Wood: Yes
  • Concrete Perimeter: Yes
  • Baseboard: Yes
  • Oil: Yes
  • Entrance Foyer: Yes
  • High Ceilings: Yes
  • Hot Tub: Yes
  • Open Floorplan: Yes
  • Lower Level: Yes
  • Two: Yes
Mobile Home
Mobile Home Information
  • Sign On Property YN: No
Rental
Rental Information
  • Occupant Type: Owner
  • Occupant Type: Owner

Property History for 404 Winter Clove Road

DateEvent & SourcePriceAppreciation
Sep 26, 2022

Sold (Public Record)

Public Record #1500530708

$950,000—
DateEvent & SourcePrice
09/26/2022

Sold (Public Record)

Public Record #1500530708

$950,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 404 Winter Clove Road

Taxable ValueLand$37,400Additions$446,200Total$483,600
Tax Record2024$20,126 ($1,677 / month)
Home Facts
Baths8Total Finished SqFt5,884 SqFtAbove Grade Finished SqFt5,884 SqFtStories3Lot Size274,428 SqFtStyleRecreationalYear Built2000Zoning01 - NOT ZONECountyGREENEAPN192400 135.00-2-12Fireplace TypeHas Fireplace

Schools near 404 Winter Clove Road

This home is within Cairo-Durham Central School District.
Rating
School
Type
Grades
Distance
Cairo Elementary School
Public - K to 5
Cairo Durham Middle School
Public - 6 to 8
Cairo Durham High School
Public - 9 to 12
Rating
School
Distance
Cairo Elementary School
PublicK to 5

Cairo Durham Middle School
Public6 to 8

Cairo Durham High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 404 Winter Clove Road, Round Top, NY 12473

404 Winter Clove Road is a single family home for sale in Round Top, NY 12473. This property was listed for sale on December 1, 2025 by Coldwell Banker Village GreenW, it's currently listed at $1,350,000. It has been on the market for a total of 29 days and was last sold on September 26, 2022. This listing's school district is Cairo-Durham Central School District. Nearby schools include Cairo Elementary School, Cairo Durham Middle School and Cairo Durham High School. 404 Winter Clove Road is a 6-bed, 7-bath, 8,284 sqft single family home built in 2000.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Coldwell Banker Village GreenW

The source of the displayed data is either the property owner or public record provided by non-governmental third parties. It is believed to be reliable but not guaranteed. This information is provided exclusively for consumers’ personal, non-commercial use. The data relating to real estate for sale or lease on this webpage comes from the the IDX Program of OneKey® MLS, Columbia Greene Northern Dutchess MLS, Hudson Valley Catskill Regional MLS and Ulster County Board of REALTORS. Real estate listings held by brokerage firms other than Compass are marked with a OneKey® MLS, Columbia Greene Northern Dutchess MLS, Hudson Valley Catskill Regional MLS or Ulster County Board of REALTORS Logo. Use of these search facilities other than by a consumer seeking to purchase or lease real estate is prohibited. The accuracy of all information is deemed reliable but not guaranteed and should be verified through personal inspection by and/or with appropriate professionals. The data contained herein is copyrighted by the IDX Program of OneKey® MLS, Columbia Greene Northern Dutchess MLS, Hudson Valley Catskill Regional MLS and Ulster County Board of REALTORS and is protected by all applicable copyright laws. Any unauthorized dissemination of this information is in violation of copyright laws and is strictly prohibited. Information Copyright 2025, OneKey® MLS, Columbia Greene Northern Dutchess MLS, Hudson Valley Catskill Regional MLS and Ulster County Board of REALTORS. All rights reserved. Data last updated: 12/03/2025 01:42 PM