4,457

Philipstown, NY Homes

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  • /29

    $1,325,000

    • 6 Beds
    • 3 Baths
    • 2,400 Sq Ft

    24 Rock St, Cold Spring, NY 10516

    Exceptional 3-Unit Investment Property in the Heart of Cold SpringRare opportunity to own a well-maintained three-unit residential rental property on a side street in the charming Village of Cold Spring. This income-producing building features three spacious two-bedroom apartments, each with separate electric meters, electric heat, and electric hot water—offering convenience and simplified

    William Pugh Houlihan Lawrence Inc.

    24 Rock St, Cold Spring, NY 10516
  • /50

    $8,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • 5,210 Sq Ft
    • House for Rent

    138 Main St, Cold Spring, NY 10516

    For the first time ever, 138 Main Street is available for rent! This stunning, recently updated home is over 2800 square feet and combines modern comfort with loads of historic charm. Nestled right in the heart of Main Street in the beautiful sought after village of Cold Spring, you can walk to all the shops and the train, just over an hour from NYC. Built with entertaining in mind, the open

    Mishara Canino Robert A. McCaffrey Realty Inc

    138 Main St, Cold Spring, NY 10516
  • 27 Arden Dr, Garrison, NY 10524

    $602,500

    Sold Jun 26, 2026

    27 Arden Dr, Garrison, NY 10524

    • 3 Beds
    • 2.5 Baths
    • 1,378 Sq Ft
    • Built 1985

    Last Sold Summary

    • 4% Below List Price
    • $437/SF
    • 37 Days On Market

    Current Estimated Value $618,506

    Last Listing Agent Jonathan Clyman JCT Realty Group Inc.

    27 Arden Dr, Garrison, NY 10524
    • 10 Northern Ave, Cold Spring, NY 10516

      Not Listed For Sale

      10 Northern Ave, Cold Spring, NY 10516

      • 2 Beds
      • 1.5 Baths
      • 961 Sq Ft
      • Built 1972
      10 Northern Ave, Cold Spring, NY 10516

      Last Sold Summary

      • 36 Days On Market

      Last Listing Agent Robert Nobile Robert A. McCaffrey Realty Inc

  • /42

    $2,490,000

    $360K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,493 Sq Ft

    215 Lane Gate Rd, Cold Spring, NY 10516

    Serene Country Living with a Contemporary Metro VibeWelcome to this one-of-a-kind country retreat, set on one of Cold Spring’s most desirable roads and immersed in the natural beauty of the Hudson Valley. Bordering a 100-acre nature preserve and offering a private walk to a secluded pond, 215 Lane Gate is a sophisticated contemporary sanctuary where architecture, comfort, and nature come

    William Pugh Houlihan Lawrence Inc.

    215 Lane Gate Rd, Cold Spring, NY 10516
  • /32

    $2,595 Per Month

    • 3 Beds
    • 1 Bath
    • 740 Sq Ft
    • Apartment for Rent

    2 Morris Ave Unit 203, Philipstown, NY 10516

    If you want to be in the heart of the village this charming apartment is for you! This spacious, light filled corner unit offers oversized rooms and brand-new double-pane windows designed to help reduce outside noise. The restaurant building is soundproofed, providing additional peace and comfort. The large, fully equipped eat-in kitchen features stainless steel appliances and plenty of space for

    Melanie Benson Robert A. McCaffrey Realty Inc

    2 Morris Ave Unit 203, Philipstown, NY 10516
  • 2680 U S 9, Cold Spring, NY 10516

    $2,050,000

    Sold Jun 17, 2026

    2680 U S 9, Cold Spring, NY 10516

    • 2 Beds
    • 2.5 Baths
    • 1,300 Sq Ft
    • Built 2020

    Last Sold Summary

    • 59% Below List Price
    • $1,577/SF
    • 376 Days On Market

    Last Listing Agent Melissa Carlton Houlihan Lawrence Inc.

    2680 U S 9, Cold Spring, NY 10516
    • 45 Manitou Rd, Philipstown, NY 10524

      Not Listed For Sale

      45 Manitou Rd, Philipstown, NY 10524

      • 3 Beds
      • 4.5 Baths
      • 2,861 Sq Ft
      • Built 2006
      45 Manitou Rd, Philipstown, NY 10524

      Last Sold Summary

      • 31 Days On Market

      Last Listing Agent Abbie Carey Houlihan Lawrence Inc.

  • /29

    $3,100,000

    • 3 Beds
    • 3.5 Baths
    • 3,896 Sq Ft

    481 Old Albany Post Rd, Garrison, NY 10524

    Deep within the Hudson Highlands, along the historic Old Albany Post Road, this extraordinary 28-acre estate offers a rare union of architectural significance, enduring privacy, and natural beauty. Beyond handcrafted iron gates framed by stone pillars, a winding drive disappears into mature woodlands before revealing a residence that feels quietly woven into the landscape. Stone and timber

    Craig Watters Compass Greater NY, LLC

    481 Old Albany Post Rd, Garrison, NY 10524
  • 43 Yesterday Dr, Cold Spring, NY 10516

    $710,000

    Sold May 05, 2026

    43 Yesterday Dr, Cold Spring, NY 10516

    • 2 Beds
    • 3 Baths
    • 2,620 Sq Ft
    • Built 2012

    Last Sold Summary

    • 9% Below List Price
    • $271/SF
    • 175 Days On Market

    Current Estimated Value $711,924

    Last Listing Agent Audra Maccariello Coldwell Banker Realty

    43 Yesterday Dr, Cold Spring, NY 10516
    • 63 Lovell Ln, Philipstown, NY 10524

      Est $2,886,176

      Not Listed For Sale

      63 Lovell Ln, Philipstown, NY 10524

      • 5 Beds
      • 4 Baths
      • 3,971 Sq Ft
      • Built 1949
      63 Lovell Ln, Philipstown, NY 10524

      Last Sold Summary

      • 50 Days On Market

      Last Listing Agent Joanna Rizoulis Julia B Fee Sothebys Int. Rlty

  • /32

    $549,000

    Pending
    • 3 Beds
    • 1.5 Baths
    • 1,512 Sq Ft

    355 Sprout Brook Rd, Garrison, NY 10524

    Move right in to this beautifully maintained raised ranch home offering the perfect blend of comfort, style and functionality. Filled with natural light, this inviting home features three bedrooms, one-and-a-half bath, hardwood floors, central air conditioning and a spacious 2 car garage. The heart of the home is the expansive great room with vaulted ceiling and skylights creating an open and

    Christine DiChiara Coldwell Banker Realty

    355 Sprout Brook Rd, Garrison, NY 10524
  • 63 Manitou Station Rd, Garrison, NY 10524

    $930,000

    Sold Mar 26, 2026

    63 Manitou Station Rd, Garrison, NY 10524

    • 3 Beds
    • 2 Baths
    • 1,918 Sq Ft
    • Built 1906

    Last Sold Summary

    • 5% Below List Price
    • $485/SF
    • 103 Days On Market

    Current Estimated Value $949,005

    Last Listing Agent Melissa Carlton Houlihan Lawrence Inc.

    63 Manitou Station Rd, Garrison, NY 10524
    • 11 Ironstone Rd, Philipstown, NY 10524

      Not Listed For Sale

      11 Ironstone Rd, Philipstown, NY 10524

      • 2 Beds
      • 2 Baths
      • 1,170 Sq Ft
      • Built 1985
      11 Ironstone Rd, Philipstown, NY 10524

      Last Sold Summary

      • 180 Days On Market

      Last Listing Agent Chelsea Carlton Houlihan Lawrence Inc.

  • /40

    $675,000

    • 3 Beds
    • 2 Baths
    • 1,234 Sq Ft

    212 Old Albany Post Rd, Garrison, NY 10524

    Beyond its rustic stone wall, discover 212 Old Albany Post Road, a charming split-level three-bedroom, two-bath ranch tucked back on a lovely, level two-acre parcel in Garrison, New York. A generous setback provides both privacy and wonderful curb appeal along this historic country lane as it meanders through Garrison's bucolic landscape.Cheerful and inviting, the home offers a

    Austin Wright Moore Compass Greater NY, LLC

    212 Old Albany Post Rd, Garrison, NY 10524
  • 41 Winston Ln, Garrison, NY 10524

    $415,000

    Sold Oct 27, 2025

    41 Winston Ln, Garrison, NY 10524

    • 1 Bed
    • 2 Baths
    • 1,000 Sq Ft
    • Built 1983

    Last Sold Summary

    • 9% Above List Price
    • $415/SF
    • 33 Days On Market

    Current Estimated Value $489,558

    Last Listing Agent Annpauline Creamer Houlihan Lawrence Inc.

    41 Winston Ln, Garrison, NY 10524
    • 26 Yesterday Dr, Cold Spring, NY 10516

      Est $724,151

      Not Listed For Sale

      26 Yesterday Dr, Cold Spring, NY 10516

      • 2 Beds
      • 2.5 Baths
      • 2,396 Sq Ft
      • Built 2013
      26 Yesterday Dr, Cold Spring, NY 10516

      Last Sold Summary

      • 95 Days On Market

      Last Listing Agent Claudia Dizenzo Hudson River Line Realty

  • /21

    $690,000

    Pending
    • 2 Beds
    • 2 Baths
    • 2,071 Sq Ft

    28 Yesterday Dr, Cold Spring, NY 10516

    Welcome to Glassbury Court of Cold Spring! Stunning Hamilton model features one floor living in a pristinely kept 55+ adult community. Nestled in the gorgeous Hudson Valley just 50 miles from Manhattan, live in the convenience of the midpoint between Cold Spring village and Fishkill. Have the easy access to restaurants and every amenity you can imagine, together with the gorgeous surrounding

    Lance Pahucki William Raveis-New York LLC

    28 Yesterday Dr, Cold Spring, NY 10516
  • 169 Old Albany Post Rd, Philipstown, NY 10524

    $428,400

    Sold Jan 22, 2026

    169 Old Albany Post Rd, Philipstown, NY 10524

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Built 1965

    Last Sold Summary

    • 4% Above List Price
    • $428/SF
    • 28 Days On Market

    Current Estimated Value $450,867

    Last Listing Agent Maria Vele Keller Williams Realty Partner

    169 Old Albany Post Rd, Philipstown, NY 10524
    • 27 Knollwood Ln, Cold Spring, NY 10516

      Est $727,708

      Not Listed For Sale

      27 Knollwood Ln, Cold Spring, NY 10516

      • 4 Beds
      • 3 Baths
      • 2,373 Sq Ft
      • Built 1975
      27 Knollwood Ln, Cold Spring, NY 10516

      Last Sold Summary

      • 209 Days On Market

      Last Listing Agent Susan Cuomo Mauti Real Broker NY LLC

  • /50

    $1,100,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 2,746 Sq Ft

    16 Chestnut St, Cold Spring, NY 10516

    Welcome to 16 Chestnut, village living at its finest, historic charm centrally located in Cold Spring, walkable to the shops and restaurants of Main Street and Metro North. Upon entry, the scale is impressive from the high ceilings in the front hall to the large living room with fireplace and proper dining room to a recently remodeled kitchen, half bath and first floor laundry. The kitchen floors

    Ann McBride-Alayon Hudson River Line Realty

    16 Chestnut St, Cold Spring, NY 10516
  • 25 E Mountain Rd S, Cold Spring, NY 10516

    $650,000

    Sold Jul 24, 2026

    25 E Mountain Rd S, Cold Spring, NY 10516

    • 4 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • Built 1960

    Last Sold Summary

    • 4% Below List Price
    • $433/SF
    • 103 Days On Market

    Current Estimated Value $662,114

    Last Listing Agent Sabrina Zeoli Limited Editions Realty, Inc.

    25 E Mountain Rd S, Cold Spring, NY 10516
    • 55 Moffat Rd, Cold Spring, NY 10516

      Not Listed For Sale

      55 Moffat Rd, Cold Spring, NY 10516

      • 3 Beds
      • 3 Baths
      • 5,018 Sq Ft
      • Built 2002
      55 Moffat Rd, Cold Spring, NY 10516

      Last Sold Summary

      • 225 Days On Market

      Last Listing Agent Terese Olsen Houlihan Lawrence Inc.

  • /40

    $3,200,000

    • 5 Beds
    • 4.5 Baths
    • 6,216 Sq Ft

    20 S Mountain Pass Spur, Garrison, NY 10524

    Just 60 minutes from Manhattan, this exceptional Hudson Highlands retreat offers a rare combination of architectural character, protected natural surroundings, and direct access to some of the region’s most celebrated outdoor destinations. Set on 13 private acres across two separate lots—including a second vacant, buildable parcel—the property is tucked away on a quiet dirt road known for its

    Annabel Taylor Four Seasons Sothebys Intl

    20 S Mountain Pass Spur, Garrison, NY 10524
  • 12 Valley Ln, Garrison, NY 10524

    $620,000

    Sold Oct 03, 2025

    12 Valley Ln, Garrison, NY 10524

    • 3 Beds
    • 2 Baths
    • 2,000 Sq Ft
    • Built 1975

    Last Sold Summary

    • 1% Below List Price
    • $310/SF
    • 37 Days On Market

    Current Estimated Value $658,666

    Last Listing Agent Maria Campanelli BHHS River Towns Real Estate

    12 Valley Ln, Garrison, NY 10524
    • 8 Manitou Rd, Garrison, NY 10524

      Est $982,063

      Not Listed For Sale

      8 Manitou Rd, Garrison, NY 10524

      • 4 Beds
      • 3.5 Baths
      • 2,288 Sq Ft
      • Built 1880
      8 Manitou Rd, Garrison, NY 10524

      Last Sold Summary

      • 39 Days On Market

      Last Listing Agent Rebekah Tighe Robert A. McCaffrey Realty Inc

  • /33

    $1,500,000

    • 4 Beds
    • 4.5 Baths
    • 5,906 Sq Ft

    19 Twin Bridges Rd, Garrison, NY 10524

    Privately set on nearly 20 acres in Garrison, 19 Twin Bridges Road offers an incredible sense of space and seclusion surrounded by the natural beauty of the Hudson Highlands.Inside, nearly 6,000 square feet of living space centers around a dramatic great room with soaring ceilings, clerestory windows, a stone fireplace and walls of glass overlooking the wooded property. The spacious kitchen

    Katherine Cucchiarella Houlihan Lawrence Inc.

    19 Twin Bridges Rd, Garrison, NY 10524
  • 2791 Route 9, Cold Spring, NY 10516

    $800,000

    Sold Jun 30, 2026

    2791 Route 9, Cold Spring, NY 10516

    • 4 Beds
    • 2 Baths
    • 1,706 Sq Ft
    • Built 1955

    Last Sold Summary

    • 14% Above List Price
    • $469/SF
    • 44 Days On Market

    Current Estimated Value $720,646

    Last Listing Agent Ann McBride-Alayon Hudson River Line Realty

    2791 Route 9, Cold Spring, NY 10516
    • 36 Healy Rd, Cold Spring, NY 10516

      Est $536,352

      Not Listed For Sale

      36 Healy Rd, Cold Spring, NY 10516

      • 1 Bed
      • 1.5 Baths
      • 958 Sq Ft
      • Built 1910
      36 Healy Rd, Cold Spring, NY 10516

      Last Sold Summary

      • 28 Days On Market

      Last Listing Agent Peter Tomann Houlihan Lawrence Inc.

  • /2

    $75,000

    • Land
    • 10,890 Sq Ft
    • $300,000 per Acre

    3 Morris Rd, Garrison, NY 10524

    Vacant land offered with sale of neighboring house at 1 Morris Rd.

    Brandon Bonfils Brown Harris Stevens

    3 Morris Rd, Garrison, NY 10524
  • 7 Treeline Cir, Cold Spring, NY 10516

    $73,000

    Sold Jul 01, 2026

    7 Treeline Cir, Cold Spring, NY 10516

    • 2 Beds
    • 1 Bath
    • 812 Sq Ft
    • Built 2004

    Last Sold Summary

    • 9% Below List Price
    • $90/SF
    • 38 Days On Market

    Last Listing Agent Gregory Schmalz Weichert Realtors

    7 Treeline Cir, Cold Spring, NY 10516
    • 107 S Highland Rd, Garrison, NY 10524

      Est $5,475,902

      Not Listed For Sale

      107 S Highland Rd, Garrison, NY 10524

      • 6 Beds
      • 6.5 Baths
      • 9,635 Sq Ft
      • Built 2014
      107 S Highland Rd, Garrison, NY 10524

      Last Sold Summary

      • 457 Days On Market

      Last Listing Agent Lindsay Matthews Houlihan Lawrence Inc.

  • /10

    $75,000

    $9K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 735 Sq Ft

    3485 U S 9, Nelsonville, NY 10516

    Welcome to The Cold Spring Mobile Home Park in the charming village of Cold Spring, New York. Nestled in a peaceful setting, this home offers comfortable, easy living with a functional layout and abundant natural light. The interior features a welcoming living room with a fireplace, dining area, kitchen, 2 bedrooms & a bath. There is also a deck, shed and 2 parking spaces. Enjoy the tranquility

    Jeffrey Hanrahan Keller Williams Realty Group

    3485 U S 9, Nelsonville, NY 10516
  • 35 Garrison Woods Rd, Garrison, NY 10524

    $1,610,000

    Sold Dec 12, 2025

    35 Garrison Woods Rd, Garrison, NY 10524

    • 3 Beds
    • 3.5 Baths
    • 3,758 Sq Ft
    • Built 1984

    Last Sold Summary

    • 8% Below List Price
    • $428/SF
    • 20 Days On Market

    Current Estimated Value $1,679,650

    Last Listing Agent Linda Hoffmann Houlihan Lawrence Inc.

    35 Garrison Woods Rd, Garrison, NY 10524
    • 113 Putnam Rd, Garrison, NY 10524

      Est $547,877

      Not Listed For Sale

      113 Putnam Rd, Garrison, NY 10524

      • 3 Beds
      • 1.5 Baths
      • 1,404 Sq Ft
      • Built 1945
      113 Putnam Rd, Garrison, NY 10524

      Last Sold Summary

      • 18 Days On Market

      Last Listing Agent Mary Jean Staudohar Douglas Elliman Real Estate

  • /23

    $575,000

    $73K PRICE DROP Pending
    • 2 Beds
    • 1.5 Baths
    • 1,456 Sq Ft

    41 Chapman Rd, Garrison, NY 10524

    The charm of Hudson Valley living is evident in this Garrison, NY home. Set on two tax lots totaling 2.5 acres, it offers privacy and a peaceful natural setting.This Cape Cod–style home features generously sized, light-filled rooms. The living area accommodates both living and dining, with a floor-to-ceiling window and sliding doors opening to the deck for an easy connection to the landscape.

    Abbie Carey Houlihan Lawrence Inc.

    41 Chapman Rd, Garrison, NY 10524
  • 64 Paulding Ave, Cold Spring, NY 10516

    $1,125,000

    Sold Oct 31, 2025

    64 Paulding Ave, Cold Spring, NY 10516

    • 5 Beds
    • 4.5 Baths
    • 3,630 Sq Ft
    • Built 1890

    Last Sold Summary

    • 2% Above List Price
    • $310/SF
    • 23 Days On Market

    Current Estimated Value $1,218,046

    Last Listing Agent Ann McBride-Alayon Hudson River Line Realty

    64 Paulding Ave, Cold Spring, NY 10516
    • 58 Aqueduct Rd, Garrison, NY 10524

      Est $706,867

      Not Listed For Sale

      58 Aqueduct Rd, Garrison, NY 10524

      • 4 Beds
      • 3 Baths
      • 2,626 Sq Ft
      • Built 1968
      58 Aqueduct Rd, Garrison, NY 10524

      Last Sold Summary

      • 201 Days On Market

      Last Listing Agent Robert Mulvey William Raveis Real Estate

  • /21

    $100,000

    $75K PRICE DROP
    • Land
    • 3.4 Acres
    • $29,412 per Acre

    50 Winston Ln, Philipstown, NY 10524

    Discover a prime opportunity to build your “meant-to-be” home on this expansive parcel of unimproved land in the Town of Philipstown. Located within the R-40 zoning district, the property offers approximately 3.4 acres in a low-density residential setting—ideal for those seeking privacy, space, and tranquility. The R-40 designation allows for the construction of one single-family detached

    Michael LaMorte eXp Realty

    50 Winston Ln, Philipstown, NY 10524
  • 21 Private Way, Garrison, NY 10524

    $1,420,000

    Sold Jun 23, 2026

    21 Private Way, Garrison, NY 10524

    • 3 Beds
    • 4 Baths
    • 2,470 Sq Ft
    • Built 2004

    Last Sold Summary

    • 2% Below List Price
    • $575/SF
    • 23 Days On Market

    Current Estimated Value $1,421,344

    Last Listing Agent Diana Polack Compass Greater NY, LLC

    21 Private Way, Garrison, NY 10524

Showing Results 41 - 80, Page 2 of 18

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