280 Winding Hill Rd, Montgomery, NY 12549

Off market oct 2024 for $730K

$715,209

Est. refi paymentEst. refi $5,273/mo

•

3,032

sq ft

280 Winding Hill Rd, Montgomery, NY 12549

About this home

Welcome home to your wooded paradise! This 3000+sf home on 8 acres is a private oasis which lends itself to multi generational living as well as working from home. Off the entry hall is an open floor plan LR with beautiful stone fplc, DR with sliders out to expansive deck & recently renovated kitchen. Down the hall is the laundry, renovated full bath & large room with high ceiling & WIC, currently being used as a main floor master. Off the living room is a den/office as well as 2 more main floor bedrooms & full bath. Upstairs is a master suite with full bath & WIC. The partial bsmt has utilities & crawl space access & walks out to the front & rear yard. There is an additn'l finished area accessible from driveway as well as bsmt, which was previously used for a home business. Detached 3 car garage w/electric offers plenty of storage & loft. Semi inground pool partially sunk in & fenced in. All hardwood floors just refinished. Large pond in front. PBSD Additional Information: HeatingFuel:Oil Above Ground,ParkingFeatures:3 Car Detached,

Single-familyProperty Type

1980Year Built

8 acresLot Size

$236Est. Price/Sq.Ft.

3 car garageParking

Listing by Elizabeth Vasapolli • Howard Hanna Rand Realty

Contact: (845) 294-3100

Bought with Elizabeth Vasapolli • Howard Hanna Rand Realty

Redfin checked: 2 minutes ago

•Source:OneKey® MLS as Distributed by MLS Grid #H6308975

Redfin Estimate

$715,209

$15K since sold in October 2024$4,000 since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 13.5% higher than the average sale price ($630K) of 6 comparable homes.

SOLD NOV 2, 2026
$505,000
A
4 beds2.5 baths1,800 sq ft
7 Judson Rd, Montgomery, NY 12549
Listing by Howard Hanna Rand Realty
SOLD OCT 20, 2026
$674,500
B
4 beds3.5 baths3,011 sq ft
41 Philip Dr, Montgomery, NY 12549
Listing by Stonewall Realty Group LLC
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 AUG 17, 2026
$647,500
D
4 beds2.5 baths2,956 sq ft
1 Boxwood Ln, Montgomery, NY 12549
Listing by Howard Hanna Rand Realty
SOLD APR 7, 2026
$530,000
E
4 beds3 baths3,144 sq ft
1085 County Route 17, Montgomery, NY 12549
Listing by Howard Hanna Rand Realty
SOLD NOV 3, 2026
$870,000
F
3 beds3 baths1,894 sq ft
114 Last Rd, Middletown, NY 10941
Listing by Howard Hanna Rand Realty

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Earn from this home

Sell

$109,071

Est. take-home

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Refinance

Est. cash available

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Rent

$3,611/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 280 Winding Hill Rd

Year

Property tax

Land + Additions

Assessment*

2026

$13,713

$23,000 + $130,100

$153,100

2025

$13,713 (+10.4%)

$23,000 + $130,100

$153,100

2024

$12,418 (+0.3%)

$23,000 + $115,500

$138,500

2023

$12,387 (+3.0%)

$23,000 + $115,500

$138,500

2022

$12,023 (+0.1%)

$23,000 + $115,500

$138,500

2021

$12,006 (−3.9%)

$23,000 + $115,500

$138,500

2020

$12,490 (+18.6%)

$23,000 + $115,500

$138,500

2019

$10,528 (+1.2%)

$23,000 + $115,500

$138,500

2018

$10,404 (+0.9%)

$23,000 + $115,500

$138,500

2017

$10,306 (−15.1%)

$23,000 + $115,500

$138,500

2016

$12,134 (+8.4%)

$23,000 + $115,500

$138,500

2015

$11,193 (+11.4%)

$23,000 + $115,500

$138,500

2014

$10,046

$23,000 + $115,500

$138,500

Tax history for 280 Winding Hill Rd

Year

Property tax

Land + Additions

Assessment*

2026

$13,713

$23,000 + $130,100

$153,100

2025

$13,713 (+10.4%)

$23,000 + $130,100

$153,100

2024

$12,418 (+0.3%)

$23,000 + $115,500

$138,500

2023

$12,387 (+3.0%)

$23,000 + $115,500

$138,500

2022

$12,023 (+0.1%)

$23,000 + $115,500

$138,500

2021

$12,006 (−3.9%)

$23,000 + $115,500

$138,500

2020

$12,490 (+18.6%)

$23,000 + $115,500

$138,500

2019

$10,528 (+1.2%)

$23,000 + $115,500

$138,500

2018

$10,404 (+0.9%)

$23,000 + $115,500

$138,500

2017

$10,306 (−15.1%)

$23,000 + $115,500

$138,500

2016

$12,134 (+8.4%)

$23,000 + $115,500

$138,500

2015

$11,193 (+11.4%)

$23,000 + $115,500

$138,500

2014

$10,046

$23,000 + $115,500

$138,500

*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

Stories

Lot width

—

Lot depth

—

Lot size

8 Acres

Year renovated

—

Sq. Ft.

3,032

Year built

1980

Style

Single Family Residential

County

Orange County

APN

332600A01200000010141200000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Oct 8, 2026.

Property details

Parking

Parking Information
Parking Total: 3
Parking Features: Detached, Driveway, Garage

Garage Information
Garage Spaces: 3
Has Garage

Interior

Fireplace Information
Has Fireplace
Fireplaces Total: 1

Heating & Cooling
Cooling: Ductwork, ENERGY STAR Qualified Equipment
Heating: Electric, Oil, Baseboard, Heat Pump

Interior Features
Interior Features: Master Downstairs,First Floor Full Bath,Eat-in Kitchen,Entrance Foyer,Granite Counters,Primary Bathroom,Open Kitchen,Walk-In Closet(s)
Appliances: Stainless Steel Appliance(s), Indirect Water Heater, Dishwasher, Dryer, Microwave, Refrigerator, Washer
Flooring: Hardwood
Levels: Three Or More
Patio And Porch Features: Deck

Room Information
Basement YN: Yes
Attic: Partial
Rooms Total: 7
Basement: Partial, See Remarks, Walk-Out Access
Additional Rooms: Office

Bathroom Information
Bathrooms Full: 3

Exterior

Exterior Features
Construction Materials: Frame, Wood Siding
Waterfront YN: Yes

Pool Information
Pool Features: Above Ground

Lot Information
Additional Parcels YN: No
Lot Features: Sloped, Stone/Brick Wall, Wooded

Property Information
Stories: 3
Living Area Source: Public Records
Property Sub Type: Single Family Residence
Property Condition: Estimated

Financial

Tax Information
Tax Year: 2023
Tax Source: Municipality
Tax Annual Amount: $12,400

Financial Information
Buyer Financing: FHA

Utilities

Utility Information
Electric Company: Orange & Rockland
Sewer: Septic Tank
Utilities: Trash Collection Private

Location

School Information
Elementary School: E J Russell 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 Montgomery to Corbett Rd. Left on West Corbett, Left on Winding Hill Rd to #280
County Or Parish: Orange County

Public facts

Beds: 4
Baths: 3.0
Sq. Ft.: 3,032
Stories: 2.0
Lot Size: 8 acres
Style: Single Family Residential
Year Built: 1980
Year Renovated: —
County: Orange County
APN: 332600A01200000010141200000

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 • 3.8mi

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

3/10 Fire Factor

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

4/10 Heat Factor

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

3/10 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

$680,000 – $823,000

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Listing by Keller Williams Valley Realty

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Home values near 280 Winding Hill Rd

Data from public records.

Address	Redfin Estimate
359 Winding Hill Road, Montgomery, NY 5 Beds \| 4 Baths \| 7114 Sq. Ft.	$1,256,511
250 Winding Hill Road, Montgomery, NY 3 Beds \| 1 Baths \| 1456 Sq. Ft.	$467,939
405 Winding Hill Road, Montgomery, NY 3 Beds \| 3.5 Baths \| 2968 Sq. Ft.	$668,177
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
51 Judson Road, Montgomery, NY 3 Beds \| 2 Baths \| 1492 Sq. Ft.	$549,730

Address	Redfin Estimate
220 Winding Hill Road, Montgomery, NY 3 Beds \| 2.5 Baths \| 2620 Sq. Ft.	$630,834
248 Winding Hill Road, Montgomery, NY 2 Beds \| 1.5 Baths \| 1778 Sq. Ft.	$464,619
409 Winding Hill Road, Montgomery, NY 4 Beds \| 2.5 Baths \| 2485 Sq. Ft.	$632,203
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
217 Winding Hill Road, Montgomery, NY 2 Beds \| 2 Baths \| 1848 Sq. Ft.	$553,028
2 Judson Road, Montgomery, NY 4 Beds \| 2.5 Baths \| 3276 Sq. Ft.	$780,007

Address	Redfin Estimate
222 Winding Hill Road, Montgomery, NY 4 Beds \| 3 Baths \| 3000 Sq. Ft.	$776,746
365 Winding Hill Road, Montgomery, NY 3 Beds \| 2 Baths \| 1820 Sq. Ft.	$592,156
243 Winding Hill Road, Montgomery, NY 4 Beds \| 3 Baths \| 2269 Sq. Ft.	$499,873
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
65 Judson Road, Montgomery, NY 4 Beds \| 2.5 Baths \| 2104 Sq. Ft.	—
41 Judson Road, Montgomery, NY 3 Beds \| 3.5 Baths \| 1972 Sq. Ft.	$514,671

Property information provided by OneKey® MLS as Distributed by MLS Grid when last listed in 2024. 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 280 Winding Hill Rd

Tax history for 280 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 280 Winding Hill Rd

More real estate resources