335

Recently Sold New Windsor, NY Homes

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  • 5 Sunrise Terrace, New Windsor, NY 12553

    $590,000

    Sold May 28, 2026

    5 Sunrise Terrace, New Windsor, NY 12553

    • 4 Beds
    • 2.5 Baths
    • 1,968 Sq Ft
    • Built 1950

    Last Sold Summary

    • 7% Above List Price
    • $300/SF
    • 29 Days On Market

    Current Estimated Value $578,879

    Last Listing Agent Zachary Crosby Tyler's Estates LLC

    5 Sunrise Terrace, New Windsor, NY 12553
  • 303 Windsor Hwy, New Windsor, NY 12553

    $450,000

    Sold Dec 09, 2025

    303 Windsor Hwy, New Windsor, NY 12553

    • 2 Beds
    • 1 Bath
    • 600 Sq Ft
    • Built 1938

    Last Sold Summary

    • $750/SF
    • 0 Days On Market

    Last Listing Agent Joel Lowy MS Realty Group USA, Inc

    303 Windsor Hwy, New Windsor, NY 12553
  • 323 Sycamore Dr, New Windsor, NY 12553

    $685,000

    Sold Jan 14, 2026

    323 Sycamore Dr, New Windsor, NY 12553

    • 4 Beds
    • 3.5 Baths
    • 3,512 Sq Ft
    • Built 1986

    Last Sold Summary

    • 2% Below List Price
    • $195/SF
    • 74 Days On Market

    Current Estimated Value $702,932

    Last Listing Agent Haakim Byrd HomeSmart Homes & Estates

    323 Sycamore Dr, New Windsor, NY 12553
  • 111 Cedar Ave, New Windsor, NY 12553

    $489,000

    Sold Jun 29, 2026

    111 Cedar Ave, New Windsor, NY 12553

    • 3 Beds
    • 3 Baths
    • 1,248 Sq Ft
    • Built 2026

    Last Sold Summary

    • $392/SF
    • 16 Days On Market

    Current Estimated Value $338,388

    Last Listing Agent Waldina Almazan RE/MAX Benchmark Realty Group

    111 Cedar Ave, New Windsor, NY 12553
  • 11 Hudson Dr, New Windsor, NY 12553

    $370,000

    Sold Feb 10, 2026

    11 Hudson Dr, New Windsor, NY 12553

    • 4 Beds
    • 2 Baths
    • 1,408 Sq Ft
    • Built 1960

    Last Sold Summary

    • 1% Above List Price
    • $263/SF
    • 54 Days On Market

    Current Estimated Value $383,281

    Last Listing Agent Alexander Panet Real Broker NY LLC

    11 Hudson Dr, New Windsor, NY 12553
  • 49 Mertes Ln, New Windsor, NY 12553

    $370,000

    Sold Nov 13, 2025

    49 Mertes Ln, New Windsor, NY 12553

    • 4 Beds
    • 1 Bath
    • 1,627 Sq Ft
    • Built 1954

    Last Sold Summary

    • 8% Below List Price
    • $227/SF
    • 87 Days On Market

    Current Estimated Value $409,319

    Last Listing Agent Frank Gerbes RE/MAX Benchmark Realty Group

    49 Mertes Ln, New Windsor, NY 12553
  • 6 Jefferson Ave, New Windsor, NY 12553

    $875,000

    Sold Oct 15, 2025

    6 Jefferson Ave, New Windsor, NY 12553

    • 4 Beds
    • 3.5 Baths
    • 2,733 Sq Ft
    • Built 2024

    Last Sold Summary

    • 9% Above List Price
    • $320/SF
    • 278 Days On Market

    Last Listing Agent George Koudounas RE/MAX Benchmark Realty Group

    6 Jefferson Ave, New Windsor, NY 12553
  • 3510 John Paul Jones Ln, New Windsor, NY 12553

    $760,000

    Sold Jul 16, 2026

    3510 John Paul Jones Ln, New Windsor, NY 12553

    • 4 Beds
    • 2.5 Baths
    • 2,276 Sq Ft
    • Built 2010

    Last Sold Summary

    • 9% Above List Price
    • $334/SF
    • 10 Days On Market

    Current Estimated Value $696,217

    Last Listing Agent John Ruggieri BHHS Hudson Valley Properties

    3510 John Paul Jones Ln, New Windsor, NY 12553
  • 155 Erie Ave, New Windsor, NY 12553

    $400,000

    Sold Dec 02, 2025

    155 Erie Ave, New Windsor, NY 12553

    • 3 Beds
    • 1.5 Baths
    • 1,192 Sq Ft
    • Built 1900

    Last Sold Summary

    • 3% Above List Price
    • $336/SF
    • 32 Days On Market

    Current Estimated Value $375,668

    Last Listing Agent Christina Tsatsaron HomeSmart Homes & Estates

    155 Erie Ave, New Windsor, NY 12553
  • 404 Carlton Cir, New Windsor, NY 12553

    $460,000

    Sold Apr 24, 2026

    404 Carlton Cir, New Windsor, NY 12553

    • 3 Beds
    • 2.5 Baths
    • 2,146 Sq Ft
    • Built 1974

    Last Sold Summary

    • 10% Below List Price
    • $214/SF
    • 100 Days On Market

    Current Estimated Value $470,977

    Last Listing Agent Ruth Pena Tejeda Exit Realty Achieve

    404 Carlton Cir, New Windsor, NY 12553
  • 14 Cimorelli Dr, New Windsor, NY 12553

    $559,000

    Sold Dec 05, 2025

    14 Cimorelli Dr, New Windsor, NY 12553

    • 4 Beds
    • 2 Baths
    • 1,908 Sq Ft
    • Built 1966

    Last Sold Summary

    • 4% Above List Price
    • $293/SF
    • 41 Days On Market

    Current Estimated Value $559,759

    Last Listing Agent Ewa Kusmierek eXp Realty

    14 Cimorelli Dr, New Windsor, NY 12553
  • 41 Creamery Dr, New Windsor, NY 12553

    $500,000

    Sold Jan 15, 2026

    41 Creamery Dr, New Windsor, NY 12553

    • 3 Beds
    • 2.5 Baths
    • 1,872 Sq Ft
    • Built 1984

    Last Sold Summary

    • 5% Above List Price
    • $267/SF
    • 24 Days On Market

    Current Estimated Value $514,392

    Last Listing Agent Jade Oliverio Howard Hanna Rand Realty

    41 Creamery Dr, New Windsor, NY 12553
  • 412 Sand Gate Dr, New Windsor, NY 12553

    $77,900

    Sold Jan 07, 2026

    412 Sand Gate Dr, New Windsor, NY 12553

    • 2 Beds
    • 1 Bath
    • 728 Sq Ft
    • Built 2018

    Last Sold Summary

    • 13% Below List Price
    • $107/SF
    • 127 Days On Market

    Last Listing Agent Sandra Spector Howard Hanna Rand Realty

    412 Sand Gate Dr, New Windsor, NY 12553
  • 2806 Cherry Tree Way, New Windsor, NY 12553

    $699,000

    Sold Mar 17, 2026

    2806 Cherry Tree Way, New Windsor, NY 12553

    • 4 Beds
    • 2.5 Baths
    • 3,500 Sq Ft
    • Built 2004

    Last Sold Summary

    • 7% Below List Price
    • $200/SF
    • 140 Days On Market

    Current Estimated Value $712,375

    Last Listing Agent Karen Taphorn Howard Hanna Rand Realty

    2806 Cherry Tree Way, New Windsor, NY 12553
  • 545 Shore Dr, New Windsor, NY 12553

    $680,000

    Sold Apr 10, 2026

    545 Shore Dr, New Windsor, NY 12553

    • 4 Beds
    • 3 Baths
    • 2,695 Sq Ft
    • Built 1971

    Last Sold Summary

    • 9% Below List Price
    • $252/SF
    • 270 Days On Market

    Current Estimated Value $674,784

    Last Listing Agent Michael Rostanzo Tactical Realty LLC

    545 Shore Dr, New Windsor, NY 12553
  • 14 Creamery Dr, New Windsor, NY 12553

    $542,900

    Sold Jul 08, 2026

    14 Creamery Dr, New Windsor, NY 12553

    • 3 Beds
    • 2.5 Baths
    • 2,020 Sq Ft
    • Built 1982

    Last Sold Summary

    • 9% Above List Price
    • $269/SF
    • 13 Days On Market

    Current Estimated Value $516,509

    Last Listing Agent Ruth Garcia Keller Williams Prestige Prop

    14 Creamery Dr, New Windsor, NY 12553
  • 1802 Hawthorn Way, New Windsor, NY 12553

    $475,000

    Sold Dec 22, 2025

    1802 Hawthorn Way, New Windsor, NY 12553

    • 3 Beds
    • 2.5 Baths
    • 2,139 Sq Ft
    • Built 2012

    Last Sold Summary

    • $222/SF
    • 32 Days On Market

    Current Estimated Value $482,347

    Last Listing Agent Philip Szumlaski Keller Williams Realty

    1802 Hawthorn Way, New Windsor, NY 12553
  • 505 Barberry Ln Unit 91, New Windsor, NY 12553

    $320,000

    Sold Sep 16, 2025

    505 Barberry Ln Unit 91, New Windsor, NY 12553

    • 2 Beds
    • 1.5 Baths
    • 1,312 Sq Ft
    • Built 1988

    Last Sold Summary

    • 2% Above List Price
    • $244/SF
    • 18 Days On Market

    Current Estimated Value $332,430

    Last Listing Agent JOHN SCARANO Keller Williams Realty

    505 Barberry Ln Unit 91, New Windsor, NY 12553
  • 223 Margo St, New Windsor, NY 12553

    $440,000

    Sold Feb 02, 2026

    223 Margo St, New Windsor, NY 12553

    • 3 Beds
    • 1.5 Baths
    • 1,691 Sq Ft
    • Built 1961

    Last Sold Summary

    • 7% Above List Price
    • $260/SF
    • 41 Days On Market

    Current Estimated Value $437,944

    Last Listing Agent Tyler Prokosch John J Lease REALTORS Inc

    223 Margo St, New Windsor, NY 12553
  • 9 Louise Dr, New Windsor, NY 12553

    $375,000

    Sold Dec 23, 2025

    9 Louise Dr, New Windsor, NY 12553

    • 3 Beds
    • 2.5 Baths
    • 1,750 Sq Ft
    • Built 1974

    Last Sold Summary

    • 23% Below List Price
    • $214/SF
    • 223 Days On Market

    Current Estimated Value $397,535

    Last Listing Agent JoCATENA HARGROVE Century 21 Hudson Valley Rlty.

    9 Louise Dr, New Windsor, NY 12553
  • Lot 1 Bethlehem Rd, New Windsor, NY 12553

    $208,000

    Sold Dec 08, 2025

    Lot 1 Bethlehem Rd, New Windsor, NY 12553

    • Land
    • 1.52 Acres
    • $136,842 per Acre

    Last Sold Summary

    • 11% Below List Price
    • 348 Days On Market

    Last Listing Agent Shawn Larry SHAHAR Management LLC

    Lot 1 Bethlehem Rd, New Windsor, NY 12553
  • 11 Shaker Ct, New Windsor, NY 12553

    $465,000

    Sold May 20, 2026

    11 Shaker Ct, New Windsor, NY 12553

    • 3 Beds
    • 2.5 Baths
    • 1,492 Sq Ft
    • Built 1987

    Last Sold Summary

    • 4% Above List Price
    • $312/SF
    • 10 Days On Market

    Current Estimated Value $469,661

    Last Listing Agent Stephanie Dignan Compass Greater NY, LLC

    11 Shaker Ct, New Windsor, NY 12553
  • 276 Temple Hill Rd Unit 1117, New Windsor, NY 12553

    $265,000

    Sold May 27, 2026

    276 Temple Hill Rd Unit 1117, New Windsor, NY 12553

    • 2 Beds
    • 1 Bath
    • 1,026 Sq Ft
    • Built 1986

    Last Sold Summary

    • 1% Below List Price
    • $258/SF
    • 41 Days On Market

    Current Estimated Value $261,876

    Last Listing Agent Jennifer Gold RE/MAX Benchmark Realty Group

    276 Temple Hill Rd Unit 1117, New Windsor, NY 12553
  • 85 Holloran Rd, New Windsor, NY 12553

    $402,000

    Sold Jun 24, 2026

    85 Holloran Rd, New Windsor, NY 12553

    • 3 Beds
    • 1 Bath
    • 1,438 Sq Ft
    • Built 1900

    Last Sold Summary

    • 2% Above List Price
    • $280/SF
    • 95 Days On Market

    Current Estimated Value $389,092

    Last Listing Agent Kathleen Rafferty RE/MAX Benchmark Realty Group

    85 Holloran Rd, New Windsor, NY 12553
  • 810 Blooming Grove Turnpike Unit 36, New Windsor, NY 12553

    $238,000

    Sold Mar 31, 2026

    810 Blooming Grove Turnpike Unit 36, New Windsor, NY 12553

    • 2 Beds
    • 1 Bath
    • 1,260 Sq Ft
    • Built 1965

    Last Sold Summary

    • 1% Above List Price
    • $189/SF
    • 13 Days On Market

    Last Listing Agent Philip Szumlaski Keller Williams Realty

    810 Blooming Grove Turnpike Unit 36, New Windsor, NY 12553
  • 618 Crab Apple Ln, New Windsor, NY 12553

    $319,000

    Sold Apr 28, 2026

    618 Crab Apple Ln, New Windsor, NY 12553

    • 2 Beds
    • 1.5 Baths
    • 1,228 Sq Ft
    • Built 1994

    Last Sold Summary

    • 2% Below List Price
    • $260/SF
    • 21 Days On Market

    Current Estimated Value $321,401

    Last Listing Agent John Willis Howard Hanna Rand Realty

    618 Crab Apple Ln, New Windsor, NY 12553
  • 3 Clemence Dr, New Windsor, NY 12553

    $795,000

    Sold May 12, 2026

    3 Clemence Dr, New Windsor, NY 12553

    • 4 Beds
    • 2.5 Baths
    • 3,653 Sq Ft
    • Built 2004

    Last Sold Summary

    • 4% Below List Price
    • $218/SF
    • 71 Days On Market

    Current Estimated Value $792,347

    Last Listing Agent Tristen Sierra Coldwell Banker Realty

    3 Clemence Dr, New Windsor, NY 12553
  • 28 Park Hill Dr, New Windsor, NY 12553

    $460,000

    Sold Aug 18, 2026

    28 Park Hill Dr, New Windsor, NY 12553

    • 3 Beds
    • 2.5 Baths
    • 1,513 Sq Ft
    • Built 1965

    Last Sold Summary

    • 8% Below List Price
    • $304/SF
    • 44 Days On Market

    Current Estimated Value $494,667

    Last Listing Agent Danielle Raguzin Re-Max Experience

    28 Park Hill Dr, New Windsor, NY 12553
  • 19 Split Tree Dr, New Windsor, NY 12553

    $400,000

    Sold Jul 15, 2026

    19 Split Tree Dr, New Windsor, NY 12553

    • 4 Beds
    • 2 Baths
    • 1,836 Sq Ft
    • Built 1965

    Last Sold Summary

    • 14% Below List Price
    • $218/SF
    • 82 Days On Market

    Current Estimated Value $426,516

    Last Listing Agent Jade Oliverio Howard Hanna Rand Realty

    19 Split Tree Dr, New Windsor, NY 12553
  • 6 Farmstead Rd, New Windsor, NY 12553

    $535,000

    Sold Feb 27, 2026

    6 Farmstead Rd, New Windsor, NY 12553

    • 3 Beds
    • 2 Baths
    • 2,768 Sq Ft
    • Built 1966

    Last Sold Summary

    • 2% Above List Price
    • $193/SF
    • 92 Days On Market

    Current Estimated Value $547,885

    Last Listing Agent Hayley Butterfield LPT Realty Tri-State, LLC

    6 Farmstead Rd, New Windsor, NY 12553
  • 107 Denniston Dr, New Windsor, NY 12553

    $770,000

    Sold May 26, 2026

    107 Denniston Dr, New Windsor, NY 12553

    • 4 Beds
    • 2.5 Baths
    • 3,065 Sq Ft
    • Built 2002

    Last Sold Summary

    • 9% Below List Price
    • $251/SF
    • 43 Days On Market

    Current Estimated Value $779,110

    Last Listing Agent Brittany Barry HV Premier Properties Realty

    107 Denniston Dr, New Windsor, NY 12553
  • 5 Buttermilk Dr, New Windsor, NY 12553

    $380,000

    Sold Dec 01, 2025

    5 Buttermilk Dr, New Windsor, NY 12553

    • 3 Beds
    • 1.5 Baths
    • 1,700 Sq Ft
    • Built 1983

    Last Sold Summary

    • 9% Above List Price
    • $224/SF
    • 0 Days On Market

    Current Estimated Value $397,159

    Last Listing Agent Federico Prada Curasi Realty, Inc.

    5 Buttermilk Dr, New Windsor, NY 12553
  • 10 Oakwood Terrace Unit 38, New Windsor, NY 12553

    $200,000

    Sold Aug 27, 2026

    10 Oakwood Terrace Unit 38, New Windsor, NY 12553

    • 2 Beds
    • 1.5 Baths
    • 1,200 Sq Ft
    • Built 1966

    Last Sold Summary

    • 9% Below List Price
    • $167/SF
    • 180 Days On Market

    Current Estimated Value $186,000

    Last Listing Agent Steve Vinti Weichert Realtors

    10 Oakwood Terrace Unit 38, New Windsor, NY 12553
  • 3 Saint Anne Dr, New Windsor, NY 12553

    $380,000

    Sold Jan 16, 2026

    3 Saint Anne Dr, New Windsor, NY 12553

    • 3 Beds
    • 1.5 Baths
    • 1,392 Sq Ft
    • Built 1959

    Last Sold Summary

    • 5% Below List Price
    • $273/SF
    • 104 Days On Market

    Current Estimated Value $397,726

    Last Listing Agent Penny Alper Your Move Matters LLC

    3 Saint Anne Dr, New Windsor, NY 12553
  • 8 E Green Rd, Rock Tavern, NY 12575

    $256,000

    Sold Sep 18, 2025

    8 E Green Rd, Rock Tavern, NY 12575

    • 5 Beds
    • 2 Baths
    • 1,962 Sq Ft
    • Built 1947

    Last Sold Summary

    • 14% Below List Price
    • $130/SF
    • 47 Days On Market

    Current Estimated Value $327,217

    Last Listing Agent Joy Gallagher Weichert Realtors

    8 E Green Rd, Rock Tavern, NY 12575
  • 276 Temple Hill Rd Unit 2604, New Windsor, NY 12553

    $260,000

    Sold Mar 19, 2026

    276 Temple Hill Rd Unit 2604, New Windsor, NY 12553

    • 2 Beds
    • 2 Baths
    • 1,176 Sq Ft
    • Built 1986

    Last Sold Summary

    • 4% Above List Price
    • $221/SF
    • 30 Days On Market

    Last Listing Agent Jahnny Crespo RE/MAX Town & Country

    276 Temple Hill Rd Unit 2604, New Windsor, NY 12553
  • 276 Temple Hill Rd Unit 2513, New Windsor, NY 12553

    $240,000

    Sold Mar 27, 2026

    276 Temple Hill Rd Unit 2513, New Windsor, NY 12553

    • 2 Beds
    • 2 Baths
    • 1,176 Sq Ft
    • Built 1986

    Last Sold Summary

    • 9% Below List Price
    • $204/SF
    • 42 Days On Market

    Current Estimated Value $255,739

    Last Listing Agent Tameeka Williams KFortuna All Aspects Realty

    276 Temple Hill Rd Unit 2513, New Windsor, NY 12553
  • 117 Holly Dr, New Windsor, NY 12553

    $485,000

    Sold Dec 05, 2025

    117 Holly Dr, New Windsor, NY 12553

    • 3 Beds
    • 1.5 Baths
    • 1,731 Sq Ft
    • Built 1941

    Last Sold Summary

    • 4% Above List Price
    • $280/SF
    • 19 Days On Market

    Current Estimated Value $488,519

    Last Listing Agent Gina De Cerbo RE/MAX Benchmark Realty Group

    117 Holly Dr, New Windsor, NY 12553
  • 2033 Little Britain Rd, Rock Tavern, NY 12575

    $610,000

    Sold Jan 27, 2026

    2033 Little Britain Rd, Rock Tavern, NY 12575

    • 3 Beds
    • 2.5 Baths
    • 2,698 Sq Ft
    • Built 2004

    Last Sold Summary

    • 5% Below List Price
    • $226/SF
    • 41 Days On Market

    Current Estimated Value $625,063

    Last Listing Agent Steve Esposito HomeSmart Homes & Estates

    2033 Little Britain Rd, Rock Tavern, NY 12575
  • 276 Temple Hill Rd Unit 2808, New Windsor, NY 12553

    $300,000

    Sold Jun 26, 2026

    276 Temple Hill Rd Unit 2808, New Windsor, NY 12553

    • 3 Beds
    • 1.5 Baths
    • 1,530 Sq Ft
    • Built 1986

    Last Sold Summary

    • 12% Below List Price
    • $196/SF
    • 87 Days On Market

    Current Estimated Value $319,267

    Last Listing Agent Kelly Roebuck Curasi Realty, Inc.

    276 Temple Hill Rd Unit 2808, New Windsor, NY 12553

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