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404 Winter Clove Road, Round Top, NY 12473 (MLS# 20255898)


$1,350,000
404 Winter Clove Road
Round Top, NY 12473
MLS# 20255898
6 beds  |  7 baths  |  8284 sqft


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photo_offline_037 photo_offline_034 photo_offline_002 photo_offline_039 photo_offline_001 3 Bedrooms / 2 Bath Guest House Dining Room in the main house Dining Room in the main house Dining Room in the main house Dining Room in the main house Dining Room in the main house photo_online_052 photo_online_053 Kitchen in the main house Kitchen in the main house photo_online_047 photo_online_005 photo_online_070 photo_online_006 photo_online_067 photo_online_008 Ballroom w/DJ booth and walls designed for optimum acoustics photo_online_009 Ballroom w/DJ booth and walls designed for optimum acoustics photo_online_010 Ballroom w/DJ booth and walls designed for optimum acoustics photo_online_012 Ballroom w/DJ booth and walls designed for optimum acoustics photo_online_013 Ballroom w/DJ booth and walls designed for optimum acoustics photo_online_014 Ballroom w/DJ booth and walls designed for optimum acoustics photo_online_015 photo_online_065 photo_online_019 photo_online_075 photo_online_020 photo_online_077 photo_online_021 photo_online_022 photo_online_023 photo_online_024 photo_online_027 photo_online_028 photo_online_029 photo_online_030 photo_online_031 photo_online_032 photo_online_033 photo_online_034 photo_online_035 photo_online_036 photo_online_037 photo_online_038 photo_online_039 photo_online_040 photo_online_011 photo_online_017 photo_online_018 photo_online_084 photo_online_085 photo_online_041 photo_online_080 photo_online_079 photo_online_078 photo_online_042 photo_online_043 photo_online_089 photo_online_088 photo_online_064 photo_online_056 photo_online_057 photo_online_058 photo_online_059 photo_online_060 photo_offline_043 photo_online_061 photo_online_062 photo_online_063 photo_online_086 photo_online_083 photo_online_087 photo_online_082 photo_online_081 photo_offline_018 photo_online_007 photo_online_016 Hot Tub photo_offline_020 photo_offline_023 photo_offline_022 photo_offline_015 photo_offline_021 photo_offline_040 photo_offline_035 photo_offline_016 photo_offline_033 photo_offline_031 photo_offline_010 photo_online_100 photo_online_095 photo_online_098 photo_online_099 photo_offline_011 photo_offline_005 photo_offline_004 photo_offline_014 photo_online_096 photo_online_094 photo_offline_032 photo_offline_019 photo_offline_017 photo_offline_044 photo_offline_045 photo_offline_041 photo_offline_042 photo_offline_024 photo_offline_006 photo_offline_025 Area Photos Area Photos Area Photos photo_offline_007 photo_offline_008 This waterfall is not on the property, but is located in the immediate area. It is accessible via the trail directly behind the home. photo_offline_030 photo_offline_009 photo_online_093 photo_online_004 photo_online_001 photo_online_002 photo_online_003 photo_offline_036

Property 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 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.

Details
Documents
Contract Information
Listing Agreement: Exclusive Right To Sell
Owner Name: Jonathan Barriga
Occupant Type: Owner
Lease Considered YN: No
Current Price: $1,350,000
Original List Price: 1350000
List Price: $1,350,000
Status: Active
Listing Contract Date: 2025-12-01
Property Sub Type: Single Family Residence
Location, Tax, and Legal
911 Address: 404 Winter Clove Road, Round Top
Township: Cairo
School District: Cairo-Durham Central School District
General Tax: 21203
School Tax: 12692
Tax Annual Amount: 33895
Assessors Full Market Value: 1381700
Tax Assessed Value: 483600
Tax Legal Description: 135.00-2-12
Parcel Number: 135.00-2-12
Tax Lot: 12
Tax Block: 2
Tax Exemptions YN: No
Zoning: 01
Zoning Description: 500 - Rec & Entertn
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.
General Property Information
Bathrooms Half: 0
Above Grade Finished Area: 5884
Below Grade Finished Area: 2400
Lot Size Acres: 6.3
New Construction YN: No
Garage YN: Yes
Attached Garage YN: Yes
Garage Spaces: 2
Sign On Property YN: No
Basement YN: Yes
Fireplace YN: Yes
Fireplaces Total: 0
List Price/SqFt: 162.96
Bedrooms Total: 6
Bathrooms Total: 7
Bathrooms Full: 7
Living Area: 8284
Year Built: 2000
Remarks and Miscellaneous
Public Remarks: 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.
Status Change Information
Status Change Timestamp: 2025-12-01
Major Change Timestamp: 2025-12-01T20:54:50Z
Major Change Type: New Listing
Appliances
Dishwasher: 1
Range: 1
Refrigerator: 1
Washer/Dryer: 1
Architectural Style
Contemporary: 1
Basement
Finished: 1
Full: 1
Sump Pump: 1
Walk-Out Access: 1
Walk-Up Access: 1
Book Information
Liber/Book: 2022
Page: 3003
Section: 135.00
Construction Materials
Frame: 1
Cooling
Central Air: 1
Electric
200+ Amp Service: 1
Generator: 1
Fireplace Features
Other: 1
Flooring
Ceramic Tile: 1
Wood: 1
Foundation Details
Concrete Perimeter: 1
Heating
Baseboard: 1
Hot Water: 1
Oil: 1
Interior Features
Entrance Foyer: 1
High Ceilings: 1
Hot Tub: 1
Open Floorplan: 1
Sauna: Sauna, Sauna
Sauna: 1
Laundry Features
Lower Level: 1
Levels
Two: 1
Lot Features
Back Yard: 1
Cleared: 1
Landscaped: 1
Level: 1
Meadow: 1
Open Lot: 1
Views: 1
Other Structures
Guest House: 1
Parking Features
Driveway: 1
Garage Faces Front: 1
Off Street: 1
On Site: 1
Outside: 1
Patio And Porch Features
Deck: 1
Patio: 1
Road Surface Type
Paved: 1
Roof
Asphalt: 1
Shingle: 1
Security Features
Fire Alarm: 1
Security System: 1
Sewer
Septic Tank: 1
Structure Type
House: 1
View
Mountain(s): 1
Water Source
Well: 1
Showing Requirements
Call Listing Agent: 1
Email Listing Agent: 1
Listing Agent Must Accompany: 1
Text Listing Agent: 1
Showing Information
Showing Attended YN: Yes
Showing Instructions: Buyer's pre-approval of proof of funds is required at the time showings are requested.
Location Tax and Legal
Street Number: 404
Street Name: Winter Clove Road
County: Greene
State: NY
Zip Code: 12473
Town (Taxable): Cairo
Property Features
Appliances: Dishwasher; Range; Refrigerator; Washer/Dryer
Architectural Style: Contemporary
Basement: Finished; Full; Sump Pump; Walk-Out Access; Walk-Up Access
Construction Materials: Frame
Cooling: Central Air
Electric: 200+ Amp Service; Generator
Fireplace Features: Other
Flooring: Ceramic Tile; Wood
Foundation Details: Concrete Perimeter
Heating: Baseboard; Hot Water; Oil
Interior Features: Entrance Foyer; High Ceilings; Hot Tub; Open Floorplan
Laundry Features: Lower Level
Levels: Two
Lot Features: Back Yard; Cleared; Landscaped; Level; Meadow; Open Lot; Views
Other Structures: Guest House
Parking Features: Driveway; Garage Faces Front; Off Street; On Site; Outside
Patio And Porch Features: Deck; Patio
Road Surface Type: Paved
Roof: Asphalt; Shingle
Security Features: Fire Alarm; Security System
Sewer: Septic Tank
Structure Type: House
View: Mountain(s)
Water Source: Well
Showing Requirements: Call Listing Agent; Email Listing Agent; Listing Agent Must Accompany; Text Listing Agent

Listing Courtesy of Coldwell Banker Village GreenW
Listing Agent: Regina Tortorella

Information deemed reliable but not guaranteed.