220 Winding Hill Rd, Montgomery, NY 12549

Off market sep 2014 for $328K

$625,539

Est. refi paymentEst. refi $2,124/mo

•

2,620

sq ft

220 Winding Hill Rd, Montgomery, NY 12549

About this home

Wooded lot with stone walls. 2-story entrance, 9' ceilings on the 1st floor. Formal LR and DR w/crown moulding + chair rail. Large kitchen open to breakfast area and FR with woodburning FP. Half bath, and an office or 4th BR. All floors hardwood or tile on both levels. The 2nd floor has 3 generous sized BRs and 2 full baths. MBA has a large jetted tub + separate tiled shower. MBR has large walk-in-closet. Full basement for expansion if needed. Fuel tank in basement. Additional Information: HeatingFuel:Oil Above Ground,ParkingFeatures:2 Car Attached,

Single-familyProperty Type

2000Year Built

2 acresLot Size

$239Est. Price/Sq.Ft.

2 car garageParking

Listing by Michele Barnette • Clickit Realty

Bought with Lyra Blumenthal • RE/MAX Benchmark Realty Group

Redfin checked: 2 minutes ago

•Source:OneKey® MLS as Distributed by MLS Grid #H4408106

Redfin Estimate

$625,539

$297K since sold in September 2014$5,000 since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 4% higher than the average sale price ($601K) of 6 comparable homes.

SOLD AUG 14, 2026
$599,000
A
3 beds2.5 baths2,236 sq ft
18 Locust Dr, Montgomery, NY 12549
Listing by Keller Williams Realty
SOLD SEP 3, 2026
$450,000
B
3 beds2 baths1,624 sq ft
559 Hill Ave, Walden, NY 12586
Listing by Cronin & Company Real Estate
SOLD JUL 17, 2026
$840,000
C
3 beds2.5 baths2,596 sq ft
2 Boyce Rd, Pine Bush, NY 12566
Listing by Curasi Realty, Inc.
SOLD AUG 20, 2026
$669,000
D
3 beds2 baths2,958 sq ft
291 Comfort Trl, Montgomery, NY 12549
Listing by Howard Hanna Rand Realty
SOLD JUL 6, 2026
$450,000
E
3 beds2 baths2,275 sq ft
2 Bruyn Ave, Pine Bush, NY 12566
Listing by YourHomeSold Guaranteed Realty
SOLD OCT 30, 2025
$600,000
F
3 beds2.5 baths2,340 sq ft
322 Union School Rd, Middletown, NY 10941
Listing by Howard Hanna Rand Realty

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$396,548

Est. take-home

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Est. cash available

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Rent

$2,953/mo

Redfin rental estimate

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Market trends in 12549, NY

Last updated October 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price

101.5%

+2.2% MoM

Median sale price

$503K

$7K MoM

Avg. days on market

34d

5 days MoM

Recently sold homes

3 MoM

New listings for sale

$275,000
3 beds1 bath1,440 sq ft
1740 State Route 17k, Montgomery, NY 12549
Listing by Keller Williams Valley Realty
$529,900
3 beds2.5 baths1,720 sq ft
237 Goodwill Rd, Montgomery, NY 12549
Listing by Century 21 E & M Williams Rlty
OPEN SUN, 11AM TO 1PM
$674,999
4 beds2.5 baths2,402 sq ft
71 Van Alst Rd, Montgomery, NY 12549
Listing by Century 21 Full Service Realty
$499,000
4 beds1.5 baths1,920 sq ft
56 Old Rt-208, Montgomery, NY 12549
Listing by MK Realty Inc
See all

Provided by Redfin

Sale history for 220 Winding Hill Rd

Date

Event

Price

HGMLS #4408106

Sep 19, 2014

Price Changed

$328,500

$125/sq ft

Sep 19, 2014

Sold

$328,500

$125/sq ft

Jul 12, 2014

Contingent

—

Jul 12, 2014

Price Changed

$335,000

$128/sq ft

Apr 17, 2014

Listed

$335,000

$128/sq ft

Wooded lot with stone walls. 2-story entrance, 9' ceilings on the 1st floor. Formal LR and DR w/ crown moulding + chair rail. Large kitchen open to breakfast area and FR with woodburning FP. Half bath, and an office or 4th BR. All floors hardwood or tile on both levels. The 2nd floor has 3 generous sized BRs and 2 full baths. MBA has a large jetted tub + separate tiled shower. MBR has large walk-in-closet. Full basement for expansion if needed. Fuel tank in basement.

OneKey® MLS as Distributed by MLS Grid #H4408106

Sep 19, 2014

Sold

$328,500

$125/sq ft

Apr 17, 2014

Listed

$335,000

$128/sq ft

OneKey® MLS as Distributed by MLS Grid #H550057

Mar 9, 2014

Listing Removed

—

Aug 15, 2013

Listed

$349,000

$133/sq ft

Public Records

Sep 18, 2012

Sold

$330,000

$126/sq ft

HGMLS #523618

Aug 17, 2012

Sold

$330,000

$126/sq ft

Aug 8, 2012

Delisted

—

Aug 8, 2012

Price Changed

$339,900

$130/sq ft

Mar 15, 2012

Listed

$330,000

$126/sq ft

OneKey® MLS as Distributed by MLS Grid #H523618

Aug 17, 2012

Sold

$330,000

$126/sq ft

Mar 15, 2012

Listed

$339,900

$130/sq ft

Public Records

Jun 8, 2006

Sold

$399,900

$153/sq ft

Public Records

May 23, 2000

Sold

$29,000

$11/sq ft

Year

Property tax

Land + Additions

Assessment*

2026

$11,680

$16,800 + $113,600

$130,400

2025

$11,680 (−0.1%)

$16,800 + $113,600

$130,400

2024

$11,692 (+0.3%)

$16,800 + $113,600

$130,400

2023

$11,663 (+3.0%)

$16,800 + $113,600

$130,400

2022

$11,320 (+0.1%)

$16,800 + $113,600

$130,400

2021

$11,304 (−3.9%)

$16,800 + $113,600

$130,400

2020

$11,760 (+1.5%)

$16,800 + $113,600

$130,400

2019

$11,583 (+9.2%)

$16,800 + $113,600

$130,400

2018

$10,610 (+1.3%)

$16,800 + $113,600

$130,400

2017

$10,474 (−8.3%)

$16,800 + $113,600

$130,400

2016

$11,425 (+8.9%)

$16,800 + $113,600

$130,400

2015

$10,490 (+21.5%)

$16,800 + $113,600

$130,400

2014

$8,635

$16,800 + $113,600

$130,400

Tax history for 220 Winding Hill Rd

Year

Property tax

Land + Additions

Assessment*

2026

$11,680

$16,800 + $113,600

$130,400

2025

$11,680 (−0.1%)

$16,800 + $113,600

$130,400

2024

$11,692 (+0.3%)

$16,800 + $113,600

$130,400

2023

$11,663 (+3.0%)

$16,800 + $113,600

$130,400

2022

$11,320 (+0.1%)

$16,800 + $113,600

$130,400

2021

$11,304 (−3.9%)

$16,800 + $113,600

$130,400

2020

$11,760 (+1.5%)

$16,800 + $113,600

$130,400

2019

$11,583 (+9.2%)

$16,800 + $113,600

$130,400

2018

$10,610 (+1.3%)

$16,800 + $113,600

$130,400

2017

$10,474 (−8.3%)

$16,800 + $113,600

$130,400

2016

$11,425 (+8.9%)

$16,800 + $113,600

$130,400

2015

$10,490 (+21.5%)

$16,800 + $113,600

$130,400

2014

$8,635

$16,800 + $113,600

$130,400

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

2.5

Stories

Lot width

—

Lot depth

—

Lot size

2 Acres

Year renovated

—

Sq. Ft.

2,424

Year built

2000

Style

Single Family Residential

County

Orange County

APN

332600A01200000010470000000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Oct 8, 2026.

Property details

Parking

Parking Information
Parking Total: 2
Parking Features: Attached, Driveway, Garage Door Opener, Garage

Garage Information
Garage Spaces: 2
Has Garage

Interior

Fireplace Information
Has Fireplace
Fireplaces Total: 1

Heating & Cooling
Cooling: Central Air
Heating: Hot Water, Oil, Other

Interior Features
Interior Features: Ceiling Fan(s),Primary Bathroom,Walk-In Closet(s)
Appliances: Cooktop, Dishwasher, Dryer, Microwave, Washer, Oil Water Heater
Levels: Two

Room Information
Basement YN: Yes
Attic: Scuttle
Rooms Total: 7
Basement: Full

Bathroom Information
Bathrooms Full: 2
Bathrooms Half: 1

Exterior

Exterior Features
Construction Materials: Frame, Vinyl Siding
Waterfront YN: No

Lot Information
Additional Parcels YN: No
Lot Features: Wooded

Property Information
Stories: 2
Living Area Source: Public Records
Property Sub Type: Single Family Residence

Financial

Tax Information
Tax Year: 2014
Tax Source: Other
Tax Annual Amount: $8,854

Financial Information
Buyer Financing: Conventional

Utilities

Utility Information
Sewer: Septic Tank
Utilities: Trash Collection Private

Location

School Information
Elementary School: Pinehurst Elementary School
Middle Or Junior School: Crispell Middle School
High School: Pine Bush Senior High School
High School District: Pine Bush

Location Information
Directions: 17K North from Village of Montgomery across bridge, right onto Corbett Rd., left onto W. Corbett Rd., becomes Winding Hill Rd., house on rt
County Or Parish: Orange County

Public facts

Beds: 3
Baths: 2.5
Sq. Ft.: 2,424
Stories: 2.0
Lot Size: 2 acres
Style: Single Family Residential
Year Built: 2000
Year Renovated: —
County: Orange County
APN: 332600A01200000010470000000

Home facts updated by county records on Oct 8, 2026

Around this home

Schools

K - 12
Preschool & daycare

E J Russell Elementary School

Public PreK-5 • Assigned • 3.9mi

5/10

Crispell Middle School

Public 6-8 • Assigned • 4.2mi

6/10

Pine Bush Senior High School

Public 9-12 • Assigned • 3.8mi

6/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

4/10 Heat Factor

6 days above 98° expected this year, 13 days in 30 years

4/10 Wind Factor

9% chance of strong winds in next 30 years

2/10 Air Factor

1 unhealthy days expected this year, 1 days in 30 years

Provided by First Street

Historical weather

Montgomery, NY • 12549

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.7 hours in June and 3.8 hours in December, placing it below the U.S. average for solar exposure.

8.7 hrs

3.8 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$595,000 – $720,000

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Home values near 220 Winding Hill Rd

Data from public records.

Address	Redfin Estimate
222 Winding Hill Road, Montgomery, NY 4 Beds \| 3 Baths \| 3000 Sq. Ft.	$776,746
243 Winding Hill Road, Montgomery, NY 4 Beds \| 3 Baths \| 2269 Sq. Ft.	$499,873
210 Winding Hill Road, Montgomery, NY 3 Beds \| 1 Baths \| 1384 Sq. Ft.	$379,036
239 Winding Hill Road, Montgomery, NY 2 Beds \| 1 Baths \| 1120 Sq. Ft.	$327,522
51 Judson Road, Montgomery, NY 3 Beds \| 2 Baths \| 1492 Sq. Ft.	$549,730
16 Judson Road, Montgomery, NY 3 Beds \| 3 Baths \| 2300 Sq. Ft.	$554,856
127 W Corbett Road, Montgomery, NY 1 Beds \| 1.5 Baths \| 1800 Sq. Ft.	$462,804

Address	Redfin Estimate
250 Winding Hill Road, Montgomery, NY 3 Beds \| 1 Baths \| 1456 Sq. Ft.	$467,939
280 Winding Hill Road, Montgomery, NY 4 Beds \| 3 Baths \| 3032 Sq. Ft.	$715,209
212 Winding Hill Road, Montgomery, NY - Beds \| - Baths \| 672 Sq. Ft.	—
233 Winding Hill Road, Montgomery, NY 3 Beds \| 2.5 Baths \| 2140 Sq. Ft.	$462,514
2 Judson Road, Montgomery, NY 4 Beds \| 2.5 Baths \| 3276 Sq. Ft.	$780,007
34 Judson Road, Montgomery, NY 4 Beds \| 2 Baths \| 1876 Sq. Ft.	$523,292
115 W Corbett Road, Montgomery, NY 3 Beds \| 2 Baths \| 1363 Sq. Ft.	$442,083

Address	Redfin Estimate
248 Winding Hill Road, Montgomery, NY 2 Beds \| 1.5 Baths \| 1778 Sq. Ft.	$464,619
204 Winding Hill Road, Montgomery, NY 2 Beds \| 1 Baths \| 800 Sq. Ft.	$297,570
218 Winding Hill Road, Montgomery, NY 3 Beds \| 1 Baths \| 1300 Sq. Ft.	$427,503
221 Winding Hill Road, Montgomery, NY 1 Beds \| - Baths \| - Sq. Ft.	$248,034
41 Judson Road, Montgomery, NY 3 Beds \| 3.5 Baths \| 1972 Sq. Ft.	$514,671
120 W Corbett Road, Montgomery, NY 3 Beds \| 2 Baths \| 1248 Sq. Ft.	$454,003
104 W Corbett Road, Montgomery, NY 4 Beds \| 1 Baths \| 1018 Sq. Ft.	$307,076

Property information provided by OneKey® MLS as Distributed by MLS Grid when last listed in 2014. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 12549, NY

Sale history for 220 Winding Hill Rd

Tax history for 220 Winding Hill Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 12549

Home values near 220 Winding Hill Rd

More real estate resources