20 Winding Hills Dr

Florida NY 10921

2644 sq. ft.

60984 sq. ft.

Single-Family

Last sold for $572,000

Brian Caplicki, last sold this property on 29 October 2026 after 203 days on market.

Overview

From the moment you step inside, there’s an ease to this home that’s hard to explain but easy to feel. Light moves effortlessly through each space, the layout just makes sense, and everything about it invites you to settle in and stay awhile. At just over 2,600 square feet, this home hits that ideal balance… not too big, not too small, but perfectly sized for the way you actually live. The split-level design is where it truly stands out. The main level opens into a bright, connected space where the living room, dining area, and kitchen flow seamlessly together. Sunlight reflects off the hardwood floors, while custom built-ins add warmth, character, and function. The kitchen offers generous workspace, abundant cabinetry, and a natural connection to the dining area, making everyday living and entertaining feel effortless. Upstairs, four spacious bedrooms and two full bathrooms provide comfort and privacy. The lower level adds an entirely different layer of flexibility, featuring an additional bedroom, a half bath, and a versatile space that can easily adapt to your needs… whether that’s a guest suite, home office, gym, or a place to unwind. Step outside and the pace slows down. There’s a quiet here… the sound of birds in the morning, open sky above, and a sense of calm that makes you want to linger a little longer. A portion of the yard is fenced, while the larger space beyond gives you room to relax, create, or simply enjoy having space around you. Positioned between Warwick and Goshen, this location gives you the best of both worlds. You’re surrounded by some of the Hudson Valley’s most sought-after destinations… from wineries, orchards, and farm markets to charming village shops, restaurants, and year-round events. Whether it’s a morning at a local farm stand, an afternoon exploring nearby trails, or an evening out in Warwick’s vibrant downtown, everything is within easy reach. Major commuter routes are close by, and NYC is approximately 55 miles away, making this a perfect balance of accessibility and escape. This is the kind of home that feels balanced in every way… in size, in layout, and in the lifestyle it offers.

Features

4 bedrooms

3 bathrooms

2644 sq. ft. floor area

60984 sq. ft. lot size

Single-Family

Estimated Value

Based on this property and similar 4 bedroom single-family properties sold in Florida over the last 12 months, the estimated median property value of 20 Winding Hills Dr is $714k.

Median value

$714k

Estimated value range

$305k - $2.5m

Median days on market

Estimated value trend

increase over the last 12 months

Average days on market is based on recent, comparable sales in Florida. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 20 Winding Hills Dr

2026

Sold

$572,000

29 Oct 2026 by Brian Caplicki, of Keller Williams Hudson Valley

Happy sellers in Florida

We have insufficient information to provide an overview of customer satisfaction for Florida. Viewing the agent profiles, reviews and sales for Florida can provide insights for this location.