571 Winding Hill Rd, Montgomery, NY 12549

Off market mar 2021 for $440K

$672,129

Est. refi paymentEst. refi $3,229/mo

•

3.5 ba

•

3,292

sq ft

571 Winding Hill Rd, Montgomery, NY 12549

About this home

Knockout interior! Like new, beautifully redone w no expense spared 3236 sf, 9 rm custom, elegant bilonial w uprades, high end features & amenties galore on 1.9 level,prof landscaped acs & huge recent deck to entertain. Dramatic open floor plan w contemporary style& flair. vaulted ceilings, hardwood & marble,ceramic & Travertine tile flrs, 4 sets French drs, central air & more. Gourmet kit, Expresso cabinets, mother of pearl back splash, ss appliances, quartz counters, 8.5x4’ center island w sink. Enormous mstr bedroom w high ceilings, balcony, wk in closet , master bath w Aerated champagne bubble bath tub, shower, marble fls & walls,heated towel rack Main bath has rain shower & granite, 2nd mstr bedroom w bath & 3rd bed. 1st level has spacious Family rm, den/rec rm & bedroom. Gas hookup for 2 fireplaces. Furnishings at additional cost available.Close to major shopping, malls, hwys, Winding Hills Park & Golf course. Why wait. It’s a WOW Additional Information: HeatingFuel:Oil Above Ground,ParkingFeatures:2 Car Attached,

Single-familyProperty Type

2002Year Built

1.9 acresLot Size

$204Est. Price/Sq.Ft.

2 spacesParking

Listing by Marion Bruhns • Howard Hanna Rand Realty

Bought with Patricia Hyer • Howard Hanna Rand Realty

Source:OneKey® MLS as Distributed by MLS Grid #H6031852

Redfin Estimate

$672,129

$232K since sold in March 2021$23K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 10.7% higher than the average sale price ($607K) of 6 comparable homes.

SOLD OCT 20, 2026
$674,500
A
4 beds3.5 baths3,011 sq ft
41 Philip Dr, Montgomery, NY 12549
Listing by Stonewall Realty Group LLC
SOLD NOV 2, 2026
$505,000
B
4 beds2.5 baths1,800 sq ft
7 Judson Rd, Montgomery, NY 12549
Listing by Howard Hanna Rand Realty
SOLD AUG 13, 2026
$599,000
C
4 beds3.5 baths3,264 sq ft
281 Lake Shore Dr, Pine Bush, NY 12566
Listing by Ridge & Valley RE Corp
SOLD JAN 27, 2026
$640,000
D
3 beds3.5 baths3,141 sq ft
61 W Corbett Rd, Montgomery, NY 12549
Listing by BHHS Hudson Valley Properties
SOLD APR 18, 2026
$550,000
E
3 beds3 baths3,021 sq ft
34 Feiertag Rd, Middletown, NY 10941
Listing by 1st Independent Realty Grp
SOLD SEP 11, 2026
$675,000
F
4 beds2.5 baths2,923 sq ft
19 Pirog Rd, Pine Bush, NY 12566
Listing by Howard Hanna Rand Realty

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Earn from this home

Sell

$318,464

Est. take-home

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Refinance

Est. cash available

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Rent

$3,567/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

100.7%

0.8% MoM

Median sale price

$500K

$4K MoM

Avg. days on market

44d

10 days MoM

Recently sold homes

4 MoM

New listings for sale

$489,000
3 beds3 baths2,400 sq ft
17 Union School Rd, Montgomery, NY 12549
Listing by Anatole House LLC
$275,000
3 beds1 bath1,440 sq ft
1740 State Route 17k, Montgomery, NY 12549
Listing by Keller Williams Valley Realty
$519,000
3 beds2.5 baths1,720 sq ft
237 Goodwill Rd, Montgomery, NY 12549
Listing by Century 21 E & M Williams Rlty
See all

Provided by Redfin

Sale history for 571 Winding Hill Rd

Date

Event

Price

Public Records

Mar 8, 2021

Sold

$440,000

$134/sq ft

OneKey® MLS as Distributed by MLS Grid #H6031852

Oct 27, 2020

Sold

$440,000

$134/sq ft

Jun 4, 2020

Price Changed

$419,999

$128/sq ft

Jun 4, 2020

Price Changed

$439,999

$134/sq ft

May 27, 2020

Price Changed

$419,999

$128/sq ft

May 20, 2020

Price Changed

$429,999

$131/sq ft

Apr 18, 2020

Relisted

—

Apr 16, 2020

Listing Removed

—

Apr 5, 2020

Listed

$439,900

$134/sq ft

HGMLS #4500094

Apr 24, 2015

Sold

$195,000

$59/sq ft

Apr 24, 2015

Price Changed

$195,000

$59/sq ft

Mar 10, 2015

Contingent

—

Mar 10, 2015

Price Changed

$209,900

$64/sq ft

Mar 7, 2015

Relisted

—

Jan 26, 2015

Contingent

—

Jan 2, 2015

Listed

$209,900

$64/sq ft

OneKey® MLS as Distributed by MLS Grid #H4500094

Apr 23, 2015

Sold

$195,000

$59/sq ft

Jan 2, 2015

Listed

$209,900

$64/sq ft

Public Records

Mar 26, 2002

Sold

$399,000

$121/sq ft

Year

Property tax

Land + Additions

Assessment*

2026

$14,225

$16,700 + $138,100

$154,800

2025

$14,225

$16,700 + $138,100

$154,800

2024

$14,217 (+0.3%)

$16,700 + $138,100

$154,800

2023

$14,170 (+3.1%)

$16,700 + $138,100

$154,800

2022

$13,741 (+9.2%)

$16,700 + $138,100

$154,800

2021

$12,585 (−0.2%)

$16,700 + $127,200

$143,900

2020

$12,613 (+1.4%)

$16,700 + $122,000

$138,700

2019

$12,436 (+1.1%)

$16,700 + $122,000

$138,700

2018

$12,301 (+1.2%)

$16,700 + $122,000

$138,700

2017

$12,160 (−12.0%)

$16,700 + $122,000

$138,700

2016

$13,819 (+1.0%)

$16,700 + $122,000

$138,700

2015

$13,684 (+2.9%)

$16,700 + $139,900

$156,600

2014

$13,295

$16,700 + $139,900

$156,600

Tax history for 571 Winding Hill Rd

Year

Property tax

Land + Additions

Assessment*

2026

$14,225

$16,700 + $138,100

$154,800

2025

$14,225

$16,700 + $138,100

$154,800

2024

$14,217 (+0.3%)

$16,700 + $138,100

$154,800

2023

$14,170 (+3.1%)

$16,700 + $138,100

$154,800

2022

$13,741 (+9.2%)

$16,700 + $138,100

$154,800

2021

$12,585 (−0.2%)

$16,700 + $127,200

$143,900

2020

$12,613 (+1.4%)

$16,700 + $122,000

$138,700

2019

$12,436 (+1.1%)

$16,700 + $122,000

$138,700

2018

$12,301 (+1.2%)

$16,700 + $122,000

$138,700

2017

$12,160 (−12.0%)

$16,700 + $122,000

$138,700

2016

$13,819 (+1.0%)

$16,700 + $122,000

$138,700

2015

$13,684 (+2.9%)

$16,700 + $139,900

$156,600

2014

$13,295

$16,700 + $139,900

$156,600

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

Property details

Interior

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

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

Room Information
# of Rooms: 8

Exterior

Exterior Information
Physical Condition: Average
Building Style Type: Colonial
Exterior Wall: Aluminum/Vinyl

Property Information
Subdivision Name: CHERRY
Living Sq. Ft: 3,292
Ground Floor Sq. Ft: 1,248
# of Stories: 2
Legal Description: LT 2 CHERRY SUB MAP 157-98 GRANT OF R O W O & R 5/31/02 L 5928

Parking & Garage Information
Parking Type: Attached Garage
Garage/Parking Sq. Ft: 700
Garage / Carport Type: Attached

Lot Information
# of Buildings: 1
Land Sq. Ft: 82,764
Legal Lot Number: 61
Legal Block Number: 1
School Tax District: PINE BUSH
Municipality Name: CRAWFORD
Acres: 1.9
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.: 3,292
Stories: 2.0
Lot Size: 1.9 acres
Style: Single Family Residential
Year Built: 2002
Year Renovated: —
County: Orange County
APN: 332600A01700000010610000000

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 • 4.0mi

5/10

Crispell Middle School

Public 6-8 • Assigned • 4.2mi

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)

32°

16°

36°

19°

54°

31°

63°

40°

70°

49°

80°

58°

84°

64°

80°

56°

75°

52°

63°

42°

52°

33°

37°

22°

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

$639,000 – $773,000

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Two and a half acres • Vaulted ceilings • Oversized windows

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New listings for sale in 12549

$489,000

3 beds3 baths2,400 sq ft

17 Union School Rd, Montgomery, NY 12549

Renovated ranch • Skylights • Oversized windows

Listing by Anatole House LLC

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Two story home • Picturesque property • Mature trees

Listing by Keller Williams Valley Realty

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Updated home • Renovated kitchen • Quartz counter-tops

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Home values near 571 Winding Hill Rd

Data from public records.

Address	Redfin Estimate
565 Winding Hill Rd, Montgomery, NY 5 Beds \| 3.5 Baths \| 4363 Sq. Ft.	$707,768
544 Winding Hill Rd, Montgomery, NY 5 Beds \| 3.5 Baths \| 2943 Sq. Ft.	$699,533
585 Winding Hill Rd, Montgomery, NY 4 Beds \| 4.5 Baths \| 3738 Sq. Ft.	$808,183
556 Winding Hill Rd, Montgomery, NY 2 Beds \| 1 Baths \| 900 Sq. Ft.	$325,714
128 Youngblood Rd, Montgomery, NY 4 Beds \| 2 Baths \| 2328 Sq. Ft.	$540,025
201 Youngblood Rd, Montgomery, NY 2 Beds \| 2.5 Baths \| 1898 Sq. Ft.	$436,300
156 Youngblood Rd, Montgomery, NY 4 Beds \| 2.5 Baths \| 1926 Sq. Ft.	$560,018

Address	Redfin Estimate
550 Winding Hill Rd, Montgomery, NY 4 Beds \| 2.5 Baths \| 2478 Sq. Ft.	$600,117
568 Winding Hill Rd, Montgomery, NY 3 Beds \| 2.5 Baths \| 2944 Sq. Ft.	$881,460
499 Winding Hill Rd, Montgomery, NY 3 Beds \| 2 Baths \| 1512 Sq. Ft.	$471,888
145 Youngblood Rd, Montgomery, NY 6 Beds \| 3.5 Baths \| 4760 Sq. Ft.	—
140 Youngblood Rd, Montgomery, NY 3 Beds \| 1.5 Baths \| 1960 Sq. Ft.	$352,855
211 Youngblood Rd, Montgomery, NY 4 Beds \| 2 Baths \| 2376 Sq. Ft.	$663,840
139 Youngblood Rd, Montgomery, NY 4 Beds \| 3 Baths \| 3114 Sq. Ft.	$550,084

Address	Redfin Estimate
560 Winding Hill Rd, Montgomery, NY 4 Beds \| 2.5 Baths \| 2644 Sq. Ft.	$702,226
496 Winding Hill Rd, Montgomery, NY 3 Beds \| 2 Baths \| 2184 Sq. Ft.	$488,411
582 Winding Hill Rd, Montgomery, NY 3 Beds \| 2 Baths \| 2024 Sq. Ft.	$544,467
232 Youngblood Rd, Montgomery, NY 4 Beds \| 2 Baths \| 2308 Sq. Ft.	$518,333
155 Youngblood Rd, Montgomery, NY 2 Beds \| 2.5 Baths \| 2246 Sq. Ft.	$572,208
224 Youngblood Rd, Montgomery, NY 3 Beds \| 2 Baths \| 1671 Sq. Ft.	$524,500
134 Youngblood Rd, Montgomery, NY 4 Beds \| 2.5 Baths \| 2744 Sq. Ft.	$695,660

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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 571 Winding Hill Rd

Tax history for 571 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 571 Winding Hill Rd

More real estate resources