Earlin Rosa
Licensed Real Estate Salesperson
REALTOR®
Stamford, NY
Office: (607) 652-2220 (845) 430-6465

404 Winter Clove Road, Round Top, NY 12473

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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, its 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 Mountains 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 youre 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.

404 Winter Clove Road | MLS# 20255898

This single family home located at 404 Winter Clove Road, Round Top, NY 12473 is currently listed for sale with an asking price of $1,350,000. This property was built in 2000 and has 6 bedrooms and 7 full baths with 8284 sq. ft. Winter Clove Road is located within the Cairo-Durham Central School District school district. Search Round Top real estate on earlin-rosa.timberlandproperties.com today.

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Property Features

Property Type: Residential - Single Family
Basement: Yes
Cooling: Central Air
Fuel Type: Oil
Garage: 2 car attached
Heating: Baseboard, Hot Water, Oil
Home Style: Contemporary
Lot Size: 6.30 Acres
Roof Type: Asphalt, Shingle
Stories: 2.0
Taxes: $33,895
Year Built: 2000

Amenities

Entrance Foyer
High Ceilings
Hot Tub
Open Floorplan
Sauna

Feature Descriptions

Appliances: Washer/Dryer, Refrigerator, Range, Dishwasher
Days on Site: 92
Exterior: Frame
Fireplace: Other
Flooring: Ceramic Tile, Wood
Laundry: Lower Level
Lot: Back Yard, Cleared, Landscaped, Level, Meadow, Open Lot, Views
Parcel #: 135.00-2-12
Parking: Garage Faces Front, On Site, Outside, Off Street, Driveway
Patio/Porch: Deck, Patio
Road Surface: Paved
Security: yes
Security Features: Fire Alarm, Security System
Sewer: Septic Tank
SQFT Total: 8284
Water: Well

Local Schools

School District: Cairo-Durham Central School District

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Estimated Payment

$ 6,222.85 per month $3,004.51 Principal & Interest $2,824.58 Property Tax $393.75 Homeowner's Insurance

Change Payment Information

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years/fixed
yearly
yearly (est.)
(Payments are an estimate and may vary by lender)

Demographics

Listed By / Shown By

Listing By

Agency Name: Coldwell Banker Village GreenW

Shown By

Agent Name: Earlin Rosa
Agent Phone: (845) 430-6465
Agency Title: Timberland Properties

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All information is deemed reliable but not guaranteed. All properties are subject to prior sale, change, or withdrawal. Neither broker(s), nor agent(s) shall be responsible for any typographical errors, misinformation, or misprints, and shall be held totally harmless. Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information 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. Information on this site was last updated 03/03/2026. The listing information on this page last changed on 03/03/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Tue 03/03/2026 1:11:57 AM EST) or Global MLS (last updated Tue 03/03/2026 1:06:55 AM EST) or New York State Alliance MLS (last updated Tue 03/03/2026 1:10:29 AM EST) or Hudson Valley Catskill Region MLS (last updated Tue 03/03/2026 12:11:14 AM EST) or OneKey MLS (last updated Tue 03/03/2026 1:10:05 AM EST). Real estate listings held by brokerage firms other than Timberland Properties may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

All information is deemed reliable but not guaranteed. All properties are subject to prior sale, change, or withdrawal. Neither broker(s), nor agent(s) shall be responsible for any typographical errors, misinformation, or misprints, and shall be held totally harmless.

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