21 Winston Drive, Rhinebeck, NY 12572
21 Winston Drive

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Last listing price: $1,450,000



Set back off a quiet country road is this sprawling 5,396 sq ft home which sits on a gently sloped hill on over 3 lush and landscaped acres with a heated in-ground pool, tennis court, 2-car garage, and separate garage building in the heart of Rhinebeck.


The home opens into an impressive foyer with its grand staircase and a wall of windows that looks out on the pool and the wooded yard beyond. To the right of the foyer, you’ll find the home’s ample and bright living room with cathedral ceilings, oversized windows, skylights, and a wood-burning fireplace as well as a separate family/tv room that overlooks the pool, tennis court, and yard. The rest of the ground floor includes a large eat-in kitchen, separate formal dining room, bonus room (currently being used as an office), a half bath, laundry room, and access to the attached 2-car garage.


At the end of the hallway, you’ll find a spacious primary bedroom suite with a sitting area and a recently renovated en-suite bathroom with a luxurious soaking tub, glass shower, and walk-in closet. Upstairs are three generously-sized bedrooms (one with a walk-in closet and another with extra space for seating, a play area, or storage), an additional full bathroom, and tons of extra space including a large rec room (currently being used as a billiards room) and a bright bonus room with skylights that can accommodate many uses (playroom, yoga, gym, workspace, storage, etc). The enormous basement (partially finished with concrete floors and drywall partitions) extends the full footprint of the house and opens to the yard for easy access to the pool and tennis court.


Outside, a beautifully paved patio surrounds the heated in-ground pool and steps down to the fenced tennis court, both of which are surrounded by trees offering privacy. Perfectly situated just minutes to dining and shopping on Mill St and E Market St in the Village of Rhinebeck, 8 minutes to Red Hook, 15 minutes to Tivoli, and 20 minutes to Kingston. Hiking, biking, and fishing at Ferncliff Forest and Poets’ Walk Park are just 8 minutes away. The Rhinecliff Amtrak line is just 12 minutes away and a less than 2-hr drive will have you in NYC!



5,396 Sq.Ft. LIVING AREA

3.07 Acres lot

Features & Amenities


  • total bedrooms4
  • Total bathrooms2.5
  • full bathrooms2
  • half bathroom1
  • Flooring Ceramic, Hardwood
  • Fireplace Wood, Living Room
  • APPLIANCES Dishwasher, Dryer, Microwave, Oven-Built In, Range, Refrigerator, Washer, Other/See Remarks
  • other interior Features Skylights

Area & Lot

  • Status Sold
  • Living Area5,396 Sq.Ft.
  • Lot Area3.07 Acres
  • MLS® ID20212828
  • YEAR BUILT1993
  • Architecture StylesContempo
  • School DistrictRhinebeck Central School District


  • Garage Space2
  • water SourceDrilled Well
  • lot featuresLandscaped, Private, Slope-Gently, Wooded
  • sewerSeptic-Ingr
  • SubstructureFrame/Stick
  • other exterior FeaturesStand By Generator, Partial Fenced, Balcony, Inground Pool, Tennis Court


  • Sales Price$1,450,000
  • Real Estate Tax $5,025
  • Zoning RC5

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