NEW 16 HRS AGO

For sale

$399,999

Est. $2,956/mo —

•

1,716

sq ft

258 Riley Rd, New Windsor, NY 12553

About this home

**5.2 ACRES OF POSSIBILITIES IN THE HEART OF THE HUDSON VALLEY!** A rare opportunity to own 5.2 acres in desirable New Windsor, offering space, versatility, and incredible potential! Whether you envision a country retreat, hobby farm, gardening, recreational space, or simply room to spread out, this unique property offers an opportunity to bring your vision to life. **PET LOVERS, TAKE NOTICE!** The property also features a huge chain-link fenced enclosure, providing a spacious, designated outdoor area for your beloved pets to roam, play, and enjoy the fresh country air! Why not give your furry friends their very own park. The property features a charming older home with approximately 1,700 square feet of living space, along with several existing functional outbuildings offering additional storage, workshop, and hobby possibilities. The home is livable but dated, presenting an excellent opportunity to renovate, personalize, and make it your own. Public tax records reflect a three-bedroom home; two original bedrooms were combined to create a spacious primary bedroom with a walk-in closet. An additional unfinished upper-level room offers potential for future improvements. The flexible floor plan includes additional living areas suitable for a den, home office, or guest-use space **LOCATION, LOCATION, LOCATION!** Enjoy the benefits of country-style living while remaining conveniently located near shopping, supermarkets, restaurants, schools, and everyday amenities. Nearby Salisbury Mills-Cornwall and Beacon train stations provide commuter rail options to NYC, with access to major highways including I-87 and I-84. New York Stewart International Airport is also conveniently located in New Windsor. Approximately 55 miles north of New York City, the area offers access to everything the beautiful Hudson Valley is known for—scenic mountains, hiking and biking trails, wineries, orchards, farmers markets, parks, Hudson River waterfront destinations, and year-round outdoor recreation. Explore nearby Cornwall, Newburgh, Beacon, and historic West Point.

Single-familyProperty Type

1900Year Built

5.2 acresLot Size

$233Price/Sq.Ft.

2 car garageParking

Listing by Alexandra Zinko • Century 21 Realty Center

Contact: 845-781-8100

Listing updated: Nov 6, 2026 at 05:01am

Redfin checked: a few seconds ago

•Source:OneKey® MLS as Distributed by MLS Grid #1065243

Payment calculator

$2,956 per month

Principal and interest$2,127

Property taxes

$766

HOA dues

Home insurance

$63

Utilities

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Open houses

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Nearby open houses (10)

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7,405 sq ft lot • Built 1886
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3 beds2.5 baths2,982 sq ft
24 Wildwood Dr, Rock Tavern, NY 12575
0.46 acre lot • 2 garage spots • Built 2024
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$825,000
4 beds3.5 baths2,876 sq ft
5 Rustic Dr, Rock Tavern, NY 12575
0.38 acre lot • 2 garage spots • Built 2026
Listing by Serhant LLC
OPEN SAT, 11AM TO 2PM3D WALKTHROUGH
$725,000
3 beds2.5 baths1,875 sq ft
21 Rustic Dr, Rock Tavern, NY 12575
0.29 acre lot • 2 garage spots • Built 2026
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OPEN SAT, 11AM TO 1PM
$1,895,000
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$539,000
4 beds2.5 baths2,500 sq ft
409 Carlton Cir, New Windsor, NY 12553
0.3 acre lot • Garage • Built 1975
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1 Sanford Ave, Chester, NY 10918
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$625,000
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OPEN SUN, 12PM TO 2PM
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4 Corey Ln, Cold Spring, NY 10516
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Around this home

Schools

K - 12
Preschool & daycare

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

Market insights

258 Riley Rd · $399,999

DAYS ON MARKET

The average home goes pending in 44 days.

SALE-TO-LIST

Most homes are selling 0% below list price.

LIST PRICE

Median sale price in this area is $498,868. (25% higher than this home)

PRICE DROP

19% of homes in this area have had a price drop in the past month.

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
Built-in features
Eat-in kitchen
Formal dining room
Natural woodwork
Open kitchen
Home office
Partial attic
Unfinished basement

Bathrooms
1 full bathroom

Kitchen
Cooktop
Dishwasher
Microwave
Oven
Refrigerator

Laundry & utility
Washer
Dryer

Heating & cooling
Electric heating
Electric cooling
Wood-burning fireplace in the living room

Sale and tax history for 258 Riley Rd

Sale History
Tax History

Date

Event

Price

OneKey® MLS as Distributed by MLS Grid #1065243

Nov 5, 2026

Listed

$399,999

$233/sq ft

OneKey® MLS as Distributed by MLS Grid #H4821098

Aug 30, 2018

Sold

$232,000

$135/sq ft

Jul 5, 2018

Contingent

—

May 11, 2018

Listed

$250,000

$146/sq ft

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,

OneKey® MLS as Distributed by MLS Grid #H4724143

Nov 28, 2017

Listing Removed

—

May 27, 2017

Listed

$259,999

$152/sq ft

Public Records

Aug 7, 1998

Sold

$50,000

$29/sq ft

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

Public record

Public record
Zoning

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

5.2 Acres

Year renovated

1916

Finished Sq. Ft.

1,716

Unfinished Sq. Ft.

—

Total 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 Oct 8, 2026.

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

93/ 100

Exceptional sunlight

Sunscore

This home receives average direct sun exposure in New Windsor. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

9.3 hrs

5.3 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 258 Riley Rd

We cannot show automated home-value estimates for this home.

Nearby homes have recently sold between $390,000 and $526,500.

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $390K to $527K.

SOLD SEP 11, 2026
$499,900 Last sold price
3 beds2.5 baths1,818 sq ft
10 Ona Ln, New Windsor, NY 12553
Listing by Cronin & Company Real Estate
$42/sq ft
smaller lot
65 years newer
SOLD SEP 23, 2026
$526,500 Last sold price
3 beds2 baths1,646 sq ft
414 Philo St, New Windsor, NY 12553
Listing by Greene Realty Group
$87/sq ft
smaller lot
73 years newer
SOLD SEP 4, 2026
$475,000 Last sold price
3 beds1.5 baths1,344 sq ft
21 Continental Dr, New Windsor, NY 12553
Listing by RE/MAX Benchmark Realty Group
$120/sq ft
smaller lot
64 years newer
SOLD JUL 14, 2026
$400,000 Last sold price
4 beds1 bath1,335 sq ft
239 Leslie Ave, New Windsor, NY 12553
Listing by Serhant LLC
$67/sq ft
smaller lot
46 years newer
SOLD OCT 22, 2026
$431,600 Last sold price
3 beds2.5 baths1,894 sq ft
11 Ona Ln, New Windsor, NY 12553
Listing by KW Hudson Valley United
$5/sq ft
smaller lot
66 years newer
SOLD DEC 19, 2025
$390,000 Last sold price
3 beds1 bath1,296 sq ft
12 Provost Dr, New Windsor, NY 12553
Listing by K. Fortuna Realty, Inc.
$68/sq ft
smaller lot
64 years newer