74 Hilltop Road, Rhinebeck, NY 12572 (MLS# 20261450)

Listing Agreement: Exclusive Right To Lease

Owner Name: Winham

Current Price: $12,000

Original List Price: 12000

List Price: $12,000

Status: Active

Listing Contract Date: 2026-04-08

Property Sub Type: Single Family Residence

911 Address: 74 Hilltop Road, Rhinebeck, NY 12572

Township: Rhinebeck

School District: Rhinebeck Central School District

Elementary School: Chancellor Livingston Elementary

Parcel Number: 135089-6370-00-210115-0000

Directions: From Rhinebeck Village, Route 308 to White Schoolhouse Rd. L onto Hilltop Rd. House on the right with Sign on the tree.

Bathrooms Half: 1

Above Grade Finished Area: 3273

Below Grade Finished Area: 0

Lot Size Acres: 6.8

Association YN: No

New Construction YN: No

Garage YN: Yes

Attached Garage YN: No

Garage Spaces: 1

Waterfront YN: No

Flood Plain YN: No

Senior Community YN: No

Sign On Property YN: No

Basement YN: No

Fireplace YN: No

Wood Stove YN: Yes

List Price/SqFt: 3.67

Bedrooms Total: 3

Bathrooms Total: 4

Bathrooms Full: 3

Living Area: 3273

Year Built: 1993

Public Remarks: Welcome to 1000 Oaks, a distinctive Rhinebeck country retreat. Set on 6.8 acres, this summer rental offers a 3,200+ square-foot main house and a heated 14' x 26' gunite pool, all surrounded by the quiet beauty of the Hudson Valley landscape. Like many exceptional homes shaped by a clear point of view, 1000 Oaks reflects the spirit of wabi-sabi, the time-honored Japanese philosophy that finds beauty in imperfection, simplicity, and harmony with the natural world. Here, the landscaping remains intentionally natural, wildflowers are welcomed and cultivated, and materials such as wood, fieldstone, and brick are thoughtfully woven throughout the property. Inside and out, a soft palette of earthy, low-contrast tones creates an atmosphere that is calm, grounded, and quietly beautiful. The home offers several especially appealing features. The family room includes an attached full bath, making it ideal for visiting guests. On the second floor of the tower, an office provides two dedicated workspaces, while the tower's third floor serves as a workout space, with walls of windows overlooking the property. In summer, once the trees are fully leafed out, the setting becomes especially secluded and serene. The heated pool is, of course, one of the season's great pleasures. Despite its sense of privacy and retreat, 1000 Oaks is conveniently located just 6 miles from the center of Rhinebeck Village, 6 miles from the Taconic State Parkway, and only a short distance from the Rhinebeck Performing Arts Center. Whether your summer in Rhinebeck or the Hudson Valley is devoted to rest, work, culture, or simply a change of rhythm, 1000 Oaks offers a setting with a strong sense of place. Its beauty is not formal or showy. It lies, instead, in the quiet coherence of the house, the land, and the life they make possible together. A 3D Walkthrough Tour is available in the digital Lookbook or by request.

Status Change Timestamp: 2026-04-08

Major Change Timestamp: 2026-04-08T13:15:09Z

Major Change Type: New Listing

Dishwasher: 1

Dryer: 1

Free-Standing Refrigerator: 1

Gas Range: 1

Microwave: 1

Oven: 1

Range: 1

Range Hood: 1

Refrigerator: 1

Stainless Steel Appliance(s): 1

Washer: 1

Water Heater: 1

Water Softener: 1

Contemporary: 1

Asphalt: 1

Attic/Crawl Hatchway(s) Insulated: 1

Frame: 1

Wood Siding: 1

Ductless: 1

Wall Unit(s): 1

French Doors: 1

Sliding Doors: 1

200+ Amp Service: 1

Circuit Breakers: 1

Generator Hookup: 1

Garden: 1

Lighting: 1

Storage: 1

Brick: 1

Ceramic Tile: 1

Concrete: 1

Hardwood: 1

Vinyl: 1

Block: 1

Heat Pump: 1

Oil: 1

Radiant Floor: 1

Beamed Ceilings: 1

Built-in Features: 1

Cathedral Ceiling(s): 1

Double Vanity: 1

High Ceilings: 1

High Speed Internet: 1

Walk-In Closet(s): 1

Tri-Level: 1

Back Yard: 1

Front Yard: 1

Garden: 1

Landscaped: 1

Many Trees: 1

Meadow: 1

Native Plants: 1

Rock Outcropping: 1

Secluded: 1

Sloped: 1

Wooded: 1

Generator: 1

Satellite Dish: 1

Garage(s): 1

See Remarks: 1

Deck: 1

Front Porch: 1

Patio: 1

Mixed: 1

Filtered: 1

Gas Heat: 1

Gunite: 1

Heated: 1

In Ground: 1

Outdoor Pool: 1

Updated/Remodeled: 1

County Road: 1

Private Road: 1

Gravel: 1

Asphalt: 1

Septic Tank: 1

Well: 1

Insulated Windows: 1

Wood Stoves Total: 1

Wood: 1

24 Hour Notice: 1

Appointment Only: 1

Listing Agent Must Accompany: 1

No Lockbox: 1

Showing Attended YN: Yes

Showing Advance Notice: 24

Bathroom: 1

Bathroom Level: First

Bedroom: 1

Dining Room: 1

Dining Room Level: First

Exercise Room: 1

Exercise Room Level: Third

Family Room: 1

Family Room Level: First

Kitchen: 1

Kitchen Level: First

Living Room: 1

Living Room Level: First

Office: 1

Office Level: Second

Primary Bathroom: 1

Primary Bedroom: 1

Primary Bedroom Level: First

Utility Room: 1

Utility Room Level: First

Street Number: 74

Street Name: Hilltop

Street Suffix: Road

County: Dutchess

State: NY

Zip Code: 12572

Town (Taxable): Dutchess