565 Winding Hill Rd, Montgomery, NY 12549

Off market nov 2018 for $46K

$743,195

Est. refi paymentEst. refi $312/mo

•

3.5 ba

•

4,363

sq ft

565 Winding Hill Rd, Montgomery, NY 12549

About this home

Custom craftsman farmhouse in pastoral country setting! This spacious 3200 sq. ft. 4 Bedroom home has so much to offer with unlimited possibilities & room to expand. Situated on 5 acres with an expansive barn and silo too!, 2 car garage, great outdoor living with wrap around porch, stone patio, barbeque pit & vast open space with pond. This home has been totally renovated,carefully & lovingly preserved, with a mix of rustic charm & modern finishes - quality rare to find - Mahogany siding,gourmet Kitchen with copper sink,commercial 6 burner double oven gas stove, subzero refrigerator, hand crafted cherry cabinets, hickory floors & dual stone fireplaces between formal dining & Kitchen, sun drenched den/office with custom spiral staircase, Master Suite with soaring ceilings, & master bath with double sinks,claw foot tub, shower with glass enclosure & huge walk in closet with built ins. Lower level offers partially finished Family Rm. & Den. 3rd Bath to be installed. An extraordinary home! Additional Information: HeatingFuel:Oil Above Ground,ParkingFeatures:2 Car Detached,

Single-familyProperty Type

1898Year Built

5.1 acresLot Size

$170Est. Price/Sq.Ft.

2 spacesParking

Listing by Gina De Cerbo • RE/MAX Benchmark Realty Group

Bought with Rosella Perpepaj • BHHS Hudson Valley Properties

Source:OneKey® MLS as Distributed by MLS Grid #H4701680

Redfin Estimate

$743,195

$696K since sold in November 2018$1,000 since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 34.7% higher than the average sale price ($552K) of 6 comparable homes.

SOLD SEP 25, 2026
$500,000
A
4 beds3 baths2,260 sq ft
5328 Searsville Rd, Pine Bush, NY 12566
Listing by Keller Williams Realty
SOLD AUG 20, 2026
$669,000
B
3 beds2 baths2,958 sq ft
291 Comfort Trl, Montgomery, NY 12549
Listing by Howard Hanna Rand Realty
SOLD AUG 11, 2026
$555,500
C
5 beds3 baths3,200 sq ft
53 W Corbett Rd, Montgomery, NY 12549
Listing by eXp Realty
SOLD APR 7, 2026
$530,000
D
4 beds3 baths3,144 sq ft
1085 County Route 17, Montgomery, NY 12549
Listing by Howard Hanna Rand Realty
SOLD SEP 24, 2026
$430,000
E
4 beds2.5 baths1,710 sq ft
70 County Route 17, Pine Bush, NY 12566
Listing by Howard Hanna Rand Realty
SOLD FEB 19, 2026
$625,000
F
4 beds3.5 baths2,912 sq ft
135 Benedict Rd, Montgomery, NY 12549
Listing by Keller Williams Realty

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Earn from this home

Sell

$667,451

Est. take-home

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Refinance

Est. cash available

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Rent

$3,886/mo

Redfin rental estimate

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Market trends in 12549, NY

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

99.4%

0.8% MoM

Median sale price

$510K

$63K MoM

Avg. days on market

39d

2 days MoM

Recently sold homes

5 MoM

New listings for sale

$514,900
3 beds2 baths1,760 sq ft
103 Bullville Rd, Montgomery, NY 12549
Listing by ARC Realty 1 in Sales
COMING SOON
$599,900
4 beds2.5 baths2,340 sq ft
24 Emperor Ln, Montgomery, NY 12549
Listing by Curasi Realty, Inc.
$324,000
3 beds1 bath1,200 sq ft
2031 State Route 17k, Montgomery, NY 12549
Listing by HomeSmart Homes & Estates
$699,900
4 beds2.5 baths2,681 sq ft
21 Francis Harrison Ct, Montgomery, NY 12549
Listing by HomeSmart Homes & Estates
OPEN TODAY TO 2PM
$349,750
3 beds2.5 baths1,437 sq ft
18 Autumn Leaf Ct, Montgomery, NY 12549
Listing by Compass Greater NY, LLC
See all

Provided by Redfin

Sale history for 565 Winding Hill Rd

Date

Event

Price

Public Records

Nov 27, 2018

Sold

$46,761

$11/sq ft

OneKey® MLS as Distributed by MLS Grid #H4701680

May 17, 2017

Sold

$425,000

$97/sq ft

May 17, 2017

Listing Removed

—

Mar 30, 2017

Listed

—

Mar 30, 2017

Price Changed

$435,000

$100/sq ft

Mar 30, 2017

Sold

$425,000

$97/sq ft

Mar 30, 2017

Price Changed

$59,000

$14/sq ft

Feb 21, 2017

Contingent

—

Jan 20, 2017

Listed

$435,000

$100/sq ft

OneKey® MLS as Distributed by MLS Grid #H4606201

Nov 16, 2016

Listing Removed

—

Feb 16, 2016

Listed

$439,900

$101/sq ft

HGMLS #4606201

Aug 31, 2016

Contingent

—

HVCRMLS #20160646

Feb 16, 2016

Listed

$439,900

$101/sq ft

Public Records

Oct 16, 2002

Sold

$230,000

$53/sq ft

Year

Property tax

Land + Additions

Assessment*

2026

$13,279

$21,100 + $123,400

$144,500

2025

$13,279

$21,100 + $123,400

$144,500

2024

$13,271 (+0.3%)

$21,100 + $123,400

$144,500

2023

$13,227 (+3.1%)

$21,100 + $123,400

$144,500

2022

$12,827 (+1.5%)

$21,100 + $123,400

$144,500

2021

$12,637 (−3.8%)

$21,100 + $123,400

$144,500

2020

$13,141 (+1.4%)

$21,100 + $123,400

$144,500

2019

$12,956 (+1.1%)

$21,100 + $123,400

$144,500

2018

$12,815 (+8.6%)

$21,100 + $123,400

$144,500

2017

$11,800 (−7.5%)

$21,100 + $123,400

$144,500

2016

$12,751 (+57.7%)

$21,100 + $123,400

$144,500

2015

$8,088 (+3.0%)

$21,100 + $123,400

$144,500

2014

$7,850

$21,100 + $81,000

$102,100

Tax history for 565 Winding Hill Rd

Year

Property tax

Land + Additions

Assessment*

2026

$13,279

$21,100 + $123,400

$144,500

2025

$13,279

$21,100 + $123,400

$144,500

2024

$13,271 (+0.3%)

$21,100 + $123,400

$144,500

2023

$13,227 (+3.1%)

$21,100 + $123,400

$144,500

2022

$12,827 (+1.5%)

$21,100 + $123,400

$144,500

2021

$12,637 (−3.8%)

$21,100 + $123,400

$144,500

2020

$13,141 (+1.4%)

$21,100 + $123,400

$144,500

2019

$12,956 (+1.1%)

$21,100 + $123,400

$144,500

2018

$12,815 (+8.6%)

$21,100 + $123,400

$144,500

2017

$11,800 (−7.5%)

$21,100 + $123,400

$144,500

2016

$12,751 (+57.7%)

$21,100 + $123,400

$144,500

2015

$8,088 (+3.0%)

$21,100 + $123,400

$144,500

2014

$7,850

$21,100 + $81,000

$102,100

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

Property details

Interior

Basement Information
Basement Type: Full

Bathroom Information
# of Full Baths: 3
# of 1/2 Baths: 1

Heating & Cooling
Air Conditioning Type: Central
Heating Fuel Type: Electric
Heating Type: Hot Air

Fireplace Information
# of Fireplaces: 3
Has Fireplace

Room Information
# of Rooms: 9

Exterior

Exterior Information
Physical Condition: Good
Building Style Type: Old
Exterior Wall: Wood

Property Information
Subdivision Name: CHERRY
Living Sq. Ft: 4,363
Ground Floor Sq. Ft: 2,002
# of Stories: 2
Legal Description: LT 1 CHERRY SUB MAP 157-98

Lot Information
# of Buildings: 1
Land Sq. Ft: 222,156
Legal Lot Number: 60
Legal Block Number: 1
School Tax District: PINE BUSH
Municipality Name: CRAWFORD
Acres: 5.1
Zoning Code: RA07
State Use Description: SINGLE FAMILY RESID

Utility Information
Sewer Type: Private
Water Service Type: Private

Financial

Assessor Information
Assessment Year: 2025

Public facts

Beds: 5
Baths: 3.5
Sq. Ft.: 4,363
Stories: 2.0
Lot Size: 5.1 acres
Style: Single Family Residential
Year Built: 1898
Year Renovated: —
County: Orange County
APN: 332600A01700000010600000000

Home facts updated by county records on Oct 8, 2026

Around this home

Schools

E J Russell Elementary School

Public PreK-5 • Assigned • 3.9mi

5/10

Crispell Middle School

Public 6-8 • Assigned • 4.1mi

6/10

Pine Bush Senior High School

Public 9-12 • Assigned • 3.7mi

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

3/10 Fire Factor

0.15% chance of being in a wildfire in next 30 years

4/10 Heat Factor

7 days above 98° expected this year, 15 days in 30 years

4/10 Wind Factor

10% chance of strong winds in next 30 years

2/10 Air Factor

1 unhealthy days expected this year, 2 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

$707,000 – $855,000

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Listing by HomeSmart Homes & Estates

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Home values near 565 Winding Hill Rd

Data from public records.

Address	Redfin Estimate
550 Winding Hill Rd, Montgomery, NY 4 Beds \| 2.5 Baths \| 2478 Sq. Ft.	$577,359
544 Winding Hill Rd, Montgomery, NY 5 Beds \| 3.5 Baths \| 2943 Sq. Ft.	$669,318

Address	Redfin Estimate
571 Winding Hill Rd, Montgomery, NY 5 Beds \| 3.5 Baths \| 3292 Sq. Ft.	$651,062
568 Winding Hill Rd, Montgomery, NY 3 Beds \| 2.5 Baths \| 2944 Sq. Ft.	$879,707

Address	Redfin Estimate
560 Winding Hill Rd, Montgomery, NY 4 Beds \| 2.5 Baths \| 2644 Sq. Ft.	$678,689
491 Winding Hill Rd, Montgomery, NY 4 Beds \| 2.5 Baths \| 2989 Sq. Ft.	$670,507

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in 12549, NY

Sale history for 565 Winding Hill Rd

Tax history for 565 Winding Hill Rd

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 565 Winding Hill Rd

More real estate resources