560 Winding Hill Rd

Off Market

560 Winding Hill Rd

Montgomery NY 12549

2644 sq. ft.

653400 sq. ft.

Single-Family

Last sold for $660,000

Philip Szumlaski, last sold this property on 19 December 2025 after 87 days on market.

Overview

Welcome to 560 Winding Hill Road, a 4-bedroom, 2.5-bath Colonial set on 15 private acres in the desirable Pine Bush School District. This home offers the perfect combination of comfort, functionality, and outdoor enjoyment for everyday living. A welcoming front porch opens into a bright and spacious interior featuring hardwood floors throughout much of the main level. The living room, anchored by a wood-burning fireplace, creates a warm and inviting gathering space, while the formal dining room is ideal for dinners and celebrations. The naturally sunlit eat-in kitchen offers stainless steel appliances, tile flooring, and plenty of space for daily meals. Upstairs, the oversized primary suite provides a true retreat with a walk-in closet, jacuzzi tub, and separate shower. Practical features include a 2-car garage, full unfinished basement with endless storage potential, and generator hook-up for peace of mind. Outdoors, the property invites year-round enjoyment—host summer barbecues on the back deck, gather around the firepit on crisp fall evenings, or take advantage of private trails that wind through your very own 15 acres. All this is just minutes from local parks, restaurants, shopping, fitness centers, and commuter routes—making it easy to balance country living with modern convenience. 560 Winding Hill Road is more than a home; it’s a place to grow, relax, and enjoy every season.

Features

4 bedrooms

3 bathrooms

2 carspaces

2 garage spaces

2644 sq. ft. floor area

653400 sq. ft. lot size

Single-Family

Estimated Value

Based on this property and similar 4 bedroom single-family properties sold in Montgomery over the last 12 months, the estimated median property value of 560 Winding Hill Rd is $645k.

Median value

$645k

Estimated value range

$255k - $967.5k

Median days on market

Estimated value trend

13%

increase over the last 12 months

Average days on market is based on recent, comparable sales in Montgomery. 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 560 Winding Hill Rd

2025

Sold

$660,000

19 Dec 2025 by Philip Szumlaski, of Keller Williams Realty

2016

Sold

$302,000

08 Feb 2016 by Marion Bruhns, of Howard Hanna Rand Realty

Happy sellers in Montgomery

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

Local market activity for 4 bedroom single-family properties in Montgomery

In the last 12 months, 26 four-bedroom single-family properties similar to 560 Winding Hill Rd, have been sold.

This represents a 31% increase in four-bedroom single-family properties sales when compared to the previous 12 months.

Sold

For Sale

Interested in selling?

People are reaching out to these agents in Montgomery for a market analysis.

Maureen E Cronin

at Cronin & Company Real Estate

(68 reviews)

Get a market analysis

Mary Jo Coleman

at Curasi Realty, Inc.

(1 review)

Get a market analysis

Walkenia Perez

at Halo Realty Properties LLC

(1 review)

Get a market analysis

Marianna Pulley

at Joseph Baratta Company Realty

(3 reviews)

Get a market analysis

Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in Montgomery

Maureen E Cronin

Sellers who recommend Maureen E Cronin have praised them for being local expert, responsive, clear communication, honest, patient, supportive, and proactive