Off market aug 2018 for $232K

$440,339

Est. refi paymentEst. refi $1,844/mo

•

1,716

sq ft

258 Riley Rd, New Windsor, NY 12553

About this home

Wonderful home on Large property could have many uses! Many Original features inside Home. Den/Office/dining room, Eat in-tiled kitchen; large pantry/laundry off kitchen in basement Three outbuildings, one a 1 horse barn. The back of the garage features a large, high ceiling studio/workshop with one whole wall of windows, and views of woods and meadows, was used as a photo studio for 20 yrs. The setting of the house with a long circular gravel drive and easy access to road make it ideal for a small business. Large outer buildings good for storage or work. The 5 acres provide privacy with old woods on two sides, surrounded by stone walls and gardens around the house. Conveniently close to all shopping needs. All this 1 Hr from NYC. Additional Information: Amenities:Storage,HeatingFuel:Oil Above Ground,ParkingFeatures:2 Car Detached,

Single-familyProperty Type

1900Year Built

5.4 acresLot Size

$257Est. Price/Sq.Ft.

2 spacesParking

Listing by Matthew Depesa • Weichert Realtors

Bought with Danielle Roche • Howard Hanna Rand Realty

Redfin checked: 2 minutes ago

•Source:OneKey® MLS as Distributed by MLS Grid #H4821098

Redfin Estimate

$440,339

$208K since sold in August 2018$8,000 since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 20.8% higher than the average sale price ($365K) of 6 comparable homes.

SOLD JUL 29, 2026
$350,000
A
3 beds1.5 baths1,470 sq ft
309 Windsor Hwy, New Windsor, NY 12553
Listing by HomeSmart Homes & Estates
BOUGHT WITH REDFIN AUG 14, 2026
$490,000
B
3 beds2 baths1,900 sq ft
3 Regimental Pl, New Windsor, NY 12553
Listing by RE/MAX Benchmark Realty Group
SOLD JUL 10, 2026
$329,000
C
3 beds2 baths1,864 sq ft
67 Bethlehem Rd, New Windsor, NY 12553
Listing by Charles J Buser
SOLD AUG 26, 2026
$352,000
D
3 beds2 baths1,184 sq ft
610 Mount Airy Rd, New Windsor, NY 12553
Listing by John J Lease REALTORS Inc
SOLD MAY 12, 2026
$265,000
E
3 beds1 bath1,525 sq ft
70 Meadowbrook Ln, New Windsor, NY 12553
Listing by Biagini Realty
SOLD JUN 24, 2026
$402,000
F
3 beds1 bath1,438 sq ft
85 Holloran Rd, New Windsor, NY 12553
Listing by RE/MAX Benchmark Realty Group

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Earn from this home

Sell

$257,979

Est. take-home

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Refinance

Est. cash available

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Rent

$2,215/mo

Redfin rental estimate

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Market trends in 12553, NY

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

101.1%

+0.5% MoM

Median sale price

$445K

$15K MoM

Avg. days on market

38d

1 days MoM

Recently sold homes

0 MoM

New listings for sale

OPEN TODAY, 12PM TO 2PM
$370,000
3 beds1.5 baths1,296 sq ft
1 Rocky Ln, New Windsor, NY 12553
Listing by eXp Realty
NEW 9 HRS AGO
$495,000
3 beds2.5 baths2,302 sq ft
202 Iron Forge Ln, New Windsor, NY 12553
Listing by RE/MAX Benchmark Realty Group
NEW 11 HRS AGO
$69,900
2 beds2 baths784 sq ft
3146 Route 9w Unit 6A, New Windsor, NY 12553
Listing by Howard Hanna Rand Realty
OPEN OCT 10, 12PM TO 2PM
$679,000
4 beds2.5 baths2,376 sq ft
2508 Constitution Way, New Windsor, NY 12553
Listing by Howard Hanna Rand Realty
$475,000
3 beds2 baths1,456 sq ft
3 Hilltop Dr, New Windsor, NY 12553
Listing by Corcoran Country Living
$619,900
5 beds2 baths— sq ft
110-112 S Jacqueline St, New Windsor, NY 12553
Listing by RE/MAX Benchmark Realty Group
OPEN TODAY, 12PM TO 2PM
$539,900
5 beds2 baths2,316 sq ft
22 Hill View Dr, New Windsor, NY 12553
Listing by KW Hudson Valley United
$449,900
3 beds1.5 baths1,314 sq ft
14 Valewood Dr, New Windsor, NY 12553
Listing by eXp Realty
OPEN SUN, 5PM TO 7PM
$285,000
3 beds1.5 baths1,512 sq ft
276 Temple Hill Rd #706, New Windsor, NY 12553
Listing by eRealty Advisors, Inc
$569,900
5 beds3 baths2,291 sq ft
39 Clintonwood Dr, New Windsor, NY 12553
Listing by HomeSmart Homes & Estates
See all

Provided by Redfin

Sale history for 258 Riley Rd

Year

Property tax

Land + Additions

Assessment*

2026

$9,189

$20,000 + $22,300

$42,300

2025

$9,189 (+3.6%)

$20,000 + $22,300

$42,300

2024

$8,871 (+0.7%)

$20,000 + $22,300

$42,300

2023

$8,807 (−2.1%)

$20,000 + $22,300

$42,300

2022

$8,997 (−0.2%)

$20,000 + $22,300

$42,300

2021

$9,014 (−0.7%)

$20,000 + $22,300

$42,300

2020

$9,076 (−27.8%)

$20,000 + $22,300

$42,300

2019

$12,572 (+693.2%)

$20,000 + $22,300

$42,300

2018

$1,585 (−64.9%)

$20,000 + $22,300

$42,300

2017

$4,522 (−50.2%)

$20,000 + $22,300

$42,300

2016

$9,078 (+92.2%)

$20,000 + $22,300

$42,300

2015

$4,723 (−16.5%)

$20,000 + $22,300

$42,300

2014

$5,654

$20,000 + $22,300

$42,300

Tax history for 258 Riley Rd

Year

Property tax

Land + Additions

Assessment*

2026

$9,189

$20,000 + $22,300

$42,300

2025

$9,189 (+3.6%)

$20,000 + $22,300

$42,300

2024

$8,871 (+0.7%)

$20,000 + $22,300

$42,300

2023

$8,807 (−2.1%)

$20,000 + $22,300

$42,300

2022

$8,997 (−0.2%)

$20,000 + $22,300

$42,300

2021

$9,014 (−0.7%)

$20,000 + $22,300

$42,300

2020

$9,076 (−27.8%)

$20,000 + $22,300

$42,300

2019

$12,572 (+693.2%)

$20,000 + $22,300

$42,300

2018

$1,585 (−64.9%)

$20,000 + $22,300

$42,300

2017

$4,522 (−50.2%)

$20,000 + $22,300

$42,300

2016

$9,078 (+92.2%)

$20,000 + $22,300

$42,300

2015

$4,723 (−16.5%)

$20,000 + $22,300

$42,300

2014

$5,654

$20,000 + $22,300

$42,300

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

Public record

Public record
Zoning

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

5.2 Acres

Year renovated

1916

Sq. Ft.

1,716

Year built

1900

Style

Single Family Residential

County

Orange County

APN

334800A03500000010752000000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Sep 28, 2026.

Property details

Parking

Parking Information
Parking Total: 2
Parking Features: Detached, Driveway

Interior

Heating & Cooling
Cooling: None
Heating: Baseboard, Hot Water, Oil, Radiant

Interior Features
Interior Features: Eat-in Kitchen
Appliances: Refrigerator, Tankless Water Heater
Levels: Three Or More
Patio And Porch Features: Patio, Porch

Room Information
Basement YN: Yes
Attic: Scuttle
Rooms Total: 8
Basement: Partially Finished, See Remarks, Walk-Out Access

Bathroom Information
Bathrooms Full: 1

Exterior

Exterior Features
Construction Materials: Cedar, Clapboard, Frame
Other Structures: Barn(s), Outbuilding, Workshop
Waterfront YN: No

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

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

Financial

Tax Information
Tax Year: 2016
Tax Source: Municipality
Tax Annual Amount: $9,300

Financial Information
Buyer Financing: Conventional

Utilities

Utility Information
Sewer: Public Sewer
Utilities: Trash Collection Public

Location

School Information
Middle Or Junior School: MEADOW HILL GLOBAL EXPLORATIONS MAGNET SCHOOL
High School: Newburgh Free Academy
High School District: Newburgh

Location Information
Hamlet: New Windsor
Directions: Route 94 to Riley to # 258 across from NW water tank
County Or Parish: Orange County

Public facts

Beds: 3
Baths: 1.0
Sq. Ft.: 1,716
Stories: 2.0
Lot Size: 5.2 acres
Style: Single Family Residential
Year Built: 1900
Year Renovated: 1916
County: Orange County
APN: 334800A03500000010752000000

Home facts updated by county records on Sep 28, 2026

Around this home

Schools

Some nearby schools may not be within this home's attendance zone. Please check the Newburgh City School District website to verify.

Vails Gate High Tech Magnet School

Public K-5 • 0.9mi

4/10

Temple Hill School

Public K-8 • 1.2mi

3/10

Newburgh Free Academy Main Campus

Public 9-12 • 3.9mi

3/10

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

13% 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

New Windsor, NY • 12553

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 8.6 hours in June and 4 hours in December, placing it below the U.S. average for solar exposure.

8.6 hrs

4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$419,000 – $507,000

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Listing by Corcoran Country Living

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Listing by RE/MAX Benchmark Realty Group

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Home values near 258 Riley Rd

Data from public records.

Address	Redfin Estimate
271 Riley Road, New Windsor, NY 3 Beds \| 2.5 Baths \| 1800 Sq. Ft.	$535,967
281 Riley Road, New Windsor, NY 3 Beds \| 2 Baths \| 1344 Sq. Ft.	$420,017

Address	Redfin Estimate
203 Riley Road, New Windsor, NY 2 Beds \| 1 Baths \| 1986 Sq. Ft.	$477,241
213 Riley Road, New Windsor, NY 3 Beds \| 2 Baths \| 2024 Sq. Ft.	$503,698

Address	Redfin Estimate
285 Riley Road, New Windsor, NY 2 Beds \| 2 Baths \| 1532 Sq. Ft.	$432,450
300 Riley Road, New Windsor, NY 3 Beds \| 2 Baths \| 1550 Sq. Ft.	$435,303

Property information provided by OneKey® MLS as Distributed by MLS Grid when last listed in 2018. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 12553, NY

Sale history for 258 Riley Rd

Tax history for 258 Riley Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 12553

Home values near 258 Riley Rd

More real estate resources