- 4 bds
- 3 ba
- 3,408 sqft
LISTING BY: HOWARD HANNA RAND REALTY
New Windsor NY Real Estate & Homes For Sale
93 results
- 110 Winding Brook Court, New Windsor, NY 12553
Showcase - 258 Riley Road, New Windsor, NY 12553
- 3 bds
- 1 ba
- 1,716 sqft
LISTING BY: CENTURY 21 REALTY CENTERCharming older home
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- Peaceful setting
- 28 Marshall Drive W, New Windsor, NY 12553
- 3 bds
- 2 ba
- 1,616 sqft
LISTING BY: HOMESMART HOMES & ESTATESBeautifully updated
- 75 Old Temple Hill Road, New Windsor, NY 12553
- 3 bds
- 2 ba
- -- sqft
LISTING BY: RE/MAX BENCHMARK REALTY GROUP5 days on Zillow
- 18 Square Hill Rd Lot 123, New Windsor, NY 12553
- 3 bds
- 2 ba
- 1,344 sqft
LISTING BY: HOWARD HANNA RAND REALTYSpacious backyard
- 7 Kearney Drive, New Windsor, NY 12553
- 2 bds
- 2 ba
- 1,056 sqft
LISTING BY: KELLER WILLIAMS REALTY16 days on Zillow
- 2002 Independence Drive, New Windsor, NY 12553
- 4 bds
- 3 ba
- 2,889 sqft
LISTING BY: HOWARD HANNA RAND REALTY4 hours ago
- 20 Ivy Rock Lane, New Windsor, NY 12553
- 3 bds
- 2 ba
- 2,165 sqft
LISTING BY: RE/MAX BENCHMARK REALTY GROUP35 days on Zillow
- 2081 Independence Drive, New Windsor, NY 12553
- 4 bds
- 3 ba
- 2,808 sqft
LISTING BY: HOWARD HANNA RAND REALTYImmaculate interior
- Single-level living
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- 117 Sandpiper Lane #1C, New Windsor, NY 12553
- 3 bds
- 2 ba
- 1,850 sqft
LISTING BY: RE/MAX BENCHMARK REALTY GROUPOpen: Fri 12am-2pm (11/13)
- 41 Ona Lane, New Windsor, NY 12553
- 4 bds
- 3 ba
- 1,872 sqft
LISTING BY: EXIT REALTY CONNECTIONS17 days on Zillow
- 6 Lannis Avenue, New Windsor, NY 12553
- 3 bds
- 3 ba
- 2,148 sqft
LISTING BY: EREALTY ADVISORS, INCNew roof
- 17 Willow Parkway, New Windsor, NY 12553
- 3 bds
- 2 ba
- 1,760 sqft
LISTING BY: SHAHAR MANAGEMENT LLCNew roof
- 40 Birchwood Drive, New Windsor, NY 12553
- 4 bds
- 3 ba
- 1,296 sqft
LISTING BY: HOWARD HANNA RAND REALTYShowcase 
- 50 Cromwell Terrace #6, New Windsor, NY 12553
- 2 bds
- 1 ba
- 880 sqft
LISTING BY: ARTISAN REALTYPrice cut: $16,000 (11/2)
- 409 Carlton Circle, New Windsor, NY 12553
- 4 bds
- 3 ba
- 2,500 sqft
LISTING BY: FOUR SEASONS SOTHEBY'S INT'L RTudor-style home
- Start survey
Help others discover what makes this area unique.
Fill out a short survey to help others know what it's like to live here. - 118 King George Drive, New Windsor, NY 12553
- 2 bds
- 1 ba
- 1,152 sqft
LISTING BY: KELLER WILLIAMS REALTY23 days on Zillow
- 2508 Constitution Way, New Windsor, NY 12553
- 4 bds
- 3 ba
- 2,376 sqft
LISTING BY: HOWARD HANNA RAND REALTYShowcase 
- 206 Tamerisk Lane, New Windsor, NY 12553
- 3 bds
- 3 ba
- 1,630 sqft
LISTING BY: HOWARD HANNA RAND REALTYNew cabinetry and hardware
- 105 Pine Drive, New Windsor, NY 12553
- 3 bds
- 2 ba
- 1,392 sqft
LISTING BY: KELLER WILLIAMS VALLEY REALTYCozy fireplace
- 263 Riley Road, New Windsor, NY 12553
- 4 bds
- 2 ba
- 2,432 sqft
LISTING BY: CURASI REALTY, INC.Open: Sun 11am-1pm (11/15)
- 120 Highwood Drive, New Windsor, NY 12553
- 3 bds
- 3 ba
- 1,633 sqft
LISTING BY: RIVER REALTY SERVICES, INC.Fully finished basement
- 10 Oakwood Terrace #37, New Windsor, NY 12553
- 3 bds
- 3 ba
- 1,400 sqft
LISTING BY: RE/MAX BENCHMARK REALTY GROUPTranquil wooded views
- 16 McDonald Court, New Windsor, NY 12553
- 4 bds
- 3 ba
- 2,772 sqft
LISTING BY: KELLER WILLIAMS VILLAGE SQ RLTOpen: Sat 12-2pm (11/14)
- 22 Hill View Drive, New Windsor, NY 12553
- 5 bds
- 2 ba
- 2,316 sqft
LISTING BY: KW HUDSON VALLEY UNITEDPrice cut: $26,000 (10/22)
- 160 Highwood Drive, New Windsor, NY 12553
- 3 bds
- 3 ba
- 1,994 sqft
LISTING BY: COMPASS GREATER NY, LLCMaster bedroom suite
- 56 days on Zillow
- 1964 State Route 32, New Windsor, NY 12553
- 4 bds
- 3 ba
- 3,160 sqft
LISTING BY: RE/MAX BENCHMARK REALTY GROUPPrice cut: $45,100 (11/11)
- 102 Pleasant Hill Road, New Windsor, NY 12553
- 5 bds
- 5 ba
- 4,499 sqft
LISTING BY: HOWARD HANNA RAND REALTY31 days on Zillow
- 51 days on Zillow
- 809 Fairway Court, New Windsor, NY 12553
- 3 bds
- 3 ba
- 2,290 sqft
LISTING BY: RE/MAX BENCHMARK REALTY GROUPOpen: Sat 1-3pm (11/14)
- 9 Broad Street, New Windsor, NY 12553
- 4 bds
- 2 ba
- 1,757 sqft
LISTING BY: COMPASS GREATER NY, LLC16 days on Zillow
- Working fireplace
- 57 Keats Drive, New Windsor, NY 12553
- 3 bds
- 2 ba
- 1,704 sqft
LISTING BY: RE/MAX BENCHMARK REALTY GROUPModern updates throughout
- 276 Temple Hill Road #1305, New Windsor, NY 12553
- 3 bds
- 2 ba
- 1,512 sqft
LISTING BY: HOMESMART HOMES & ESTATESModern finishes throughout
- 241 Garden Street, New Windsor, NY 12553
- 3 bds
- 3 ba
- 1,812 sqft
LISTING BY: KW HUDSON VALLEY UNITEDPrice cut: $10,000 (10/22)
- 66 Silver Spring Road, New Windsor, NY 12553
- 3 bds
- 1 ba
- 1,592 sqft
LISTING BY: HOWARD HANNA RAND REALTYPrivate koi pond
- 584 Shore Drive, New Windsor, NY 12553
- 4 bds
- 3 ba
- 2,518 sqft
LISTING BY: UNITED RE HUDSON VALLEY EDGEPrice cut: $20,000 (10/14)
- 15 days on Zillow
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Buying a Home in New Windsor NY: Frequently Asked Questions
How much do homes cost in New Windsor NY?
Homes across New Windsor, NY have a Zillow Home Value Index of $444,321 as of September 2026, a figure that reflects the value of all homes in the area rather than only those currently on the market. The median list price of homes for sale is $460,000, which is above the index, so asking prices on active listings run higher than the broader measure.
Are home values going up or down in New Windsor NY?
Home values in New Windsor, NY have increased 3.9% over the past year as of September 2026. That brings the Zillow Home Value Index to $444,321.
Is New Windsor NY a buyer's or seller's market?
New Windsor, NY is currently a buyer's market, according to Zillow Market Temperature. That label generally means buyers have more time to decide and more room to negotiate. Price cuts have been taken on 21.6% of current listings.
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