4,506

Philipstown, NY Homes

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  • 39 Upland Dr, Garrison, NY 10524
    39 Upland Dr, Garrison, NY 10524
    39 Upland Dr, Garrison, NY 10524
    /24

    $355,000

    • 2 Beds
    • 1 Bath
    • 1,160 Sq Ft

    39 Upland Dr, Garrison, NY 10524

    Welcome to 39 Upland Drive, Garrison, NY! This charming property offers great potential for a variety of uses, including as a weekend getaway or short-term rental opportunity (subject to local regulations). Featuring classic Hudson Valley charm and surrounded by nature, this home provides a peaceful setting while remaining conveniently close to major highways, hiking trails, and the Hudson River.

    Felix Pena RE/MAX Benchmark Realty Group

    39 Upland Dr, Garrison, NY 10524
  • 41 Mountain Brook Dr, Cold Spring, NY 10516

    $815,000 Sold Sep 06, 2025

    • 2,544 Sq Ft
    • $320/SF
    • 55 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1996

    41 Mountain Brook Dr, Cold Spring, NY 10516

    This charming four-bedroom home is nestled on a picturesque parcel in the heart of the Hudson Valley, with direct access to protected New York State land—offering hiking trails right from your doorstep. Located in the sought-after Cold Spring area, this property is all about peace, privacy, and the beauty of nature. Outside, enjoy timeless stone walls, flourishing perennial gardens, and mature

    Linda Hoffmann Houlihan Lawrence Inc.

    41 Mountain Brook Dr, Cold Spring, NY 10516
  • 56 Aqueduct Rd, Garrison, NY 10524
    56 Aqueduct Rd, Garrison, NY 10524
    56 Aqueduct Rd, Garrison, NY 10524
    /33

    $450,000

    • 3 Beds
    • 2 Baths
    • 1,340 Sq Ft

    56 Aqueduct Rd, Garrison, NY 10524

    Welcome to 56 Aqueduct Road in Garrison’s desirable Continental Village! This charming 3-bedroom, 2-bath home sits on a beautifully landscaped 0.4 acre lot within a lake community offering swimming, fishing, and beach access. Inside, enjoy a bright and inviting layout featuring a renovated kitchen and full bath, spacious living room, and a den/home office. A three-season screened-in deck

    Steven Connolly Twin Bridges Properties

    56 Aqueduct Rd, Garrison, NY 10524
  • 8 Manitou Rd, Garrison, NY 10524

    $932,500 Sold Aug 29, 2025

    • 2,288 Sq Ft
    • $408/SF
    • 39 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1880

    8 Manitou Rd, Garrison, NY 10524

    Privacy and space abound with stone pathways, mature trees, a glorious garden and views of the Hudson Highland mountains surrounding this charming, well maintained home. There's a stream worthy of a dip or just a visit to gaze at the sparkling water, enjoy the sounds of nature, and experience the thriving wildlife. Plenty of space to live, work, garden and entertain make this an idyllic country

    Rebekah Tighe Robert A. McCaffrey Realty Inc

    8 Manitou Rd, Garrison, NY 10524
  • 2680 Route 9, Cold Spring, NY 10516
    2680 Route 9, Cold Spring, NY 10516
    2680 Route 9, Cold Spring, NY 10516
    /5

    $1,900,000

    • Land
    • 66 Acres
    • $28,788 per Acre

    2680 Route 9, Cold Spring, NY 10516

    65+ acres of rolling terrain offers endless possibilities in Cold Spring, NY. Subdivide into as many as 6 potential home sites, several boasting sweeping Hudson Highlands views with potential access points at Old Albany Post Road and Route 9 or preserve the entire parcel for your extraordinary private estate. Access easements can be negotiated to align with your vision. Ideally located just

    Melissa Carlton Houlihan Lawrence Inc.

    2680 Route 9, Cold Spring, NY 10516
  • 825 New York 9d, Philipstown, NY

    $825,000 Sold Aug 28, 2025

    • Land
    • 20 Acres
    • $41,250 per Acre
    • 434 Days On Market

    825 New York 9d, Philipstown, NY

    A rare opportunity to purchase a spectacular 20-acre sanctuary of natural beauty within walking distance to the cozy waterfront community of Garrison. This prime parcel of land is pure serenity, cocooned in a woodland oasis with a meandering stream and waterfall and scenic Hudson River views. It’s a hiker’s paradise with trails that include a portion of the historic Benedict Arnold flight path,

    Dalia Valdes Julia B Fee Sothebys Int. Rlty

    825 New York 9d, Philipstown, NY
  • 47 Healy Rd, Cold Spring, NY 10516
    47 Healy Rd, Cold Spring, NY 10516
    47 Healy Rd, Cold Spring, NY 10516
    /25

    $590,000

    • 3 Beds
    • 1 Bath
    • 1,042 Sq Ft

    47 Healy Rd, Cold Spring, NY 10516

    If you’re looking to be close to Cold Spring Main Street while still enjoying the beauty of nature in a private setting, this home is for you! Located in the Village of Nelsonville, just minutes from the Hudson riverfront, Metro-North Cold Spring station, hiking trails, and the Haldane Central School District. The main level offers everything you need on one floor, including a living room, dining

    Rebecca Bardes Houlihan Lawrence Inc.

    47 Healy Rd, Cold Spring, NY 10516
  • 104 Crest Rd, Cold Spring, NY 10516

    $700,000 Sold Aug 28, 2025

    • 2,232 Sq Ft
    • $314/SF
    • 97 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1969

    104 Crest Rd, Cold Spring, NY 10516

    This remarkable house offers staggering, panoramic mountain views, XL window panes throughout the living space, a deck that runs the length of the house for entertaining, & a screened in porch to enjoy the outdoors. A must-see, this house has modern SS appliances, top of the line quartz countertops, and a beautiful view. Scenic views can also be enjoyed from the Master BR, the Living Room, and

    Komal Garewal Winwin Realty

    104 Crest Rd, Cold Spring, NY 10516
  • 43 Yesterday Dr, Cold Spring, NY 10516
    43 Yesterday Dr, Cold Spring, NY 10516
    43 Yesterday Dr, Cold Spring, NY 10516
    /40

    $727,000

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

    43 Yesterday Dr, Cold Spring, NY 10516

    Welcome to 43 Yesterday Drive in beautiful Cold Spring, NY—where luxury living meets peaceful Hudson Valley charm. Nestled just 50 miles north of Manhattan and moments from the heart of the Cold Spring village, this location offers the perfect blend of convenience and tranquility. Enjoy easy access to Route 9, boutique shops, fine dining, and the Metro-North station for seamless travel to

    Audra Maccariello Coldwell Banker Realty

    43 Yesterday Dr, Cold Spring, NY 10516
  • 125 Barrett Pond Rd, Cold Spring, NY 10516

    $580,000 Sold Aug 21, 2025

    • 1,103 Sq Ft
    • $526/SF
    • 36 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1967

    125 Barrett Pond Rd, Cold Spring, NY 10516

    This cheerful charmer has the best of both worlds: It's private and woodsy with easy access and proximity to the village of Cold Spring. In addition to the spacious living room with working fireplace there is a 250 square foot three-season sunroom with a cathedral ceiling, exposed beams and views of the trees and rock outcroppings. The kitchen is brand new and features honed quartz countertops,

    Rebekah Tighe Robert A. McCaffrey Realty Inc

    125 Barrett Pond Rd, Cold Spring, NY 10516
  • 34 Hudson Ridge, Garrison, NY 10524
    34 Hudson Ridge, Garrison, NY 10524
    34 Hudson Ridge, Garrison, NY 10524
    /41

    $2,195,000

    • 4 Beds
    • 4 Baths
    • 3,734 Sq Ft

    34 Hudson Ridge, Garrison, NY 10524

    At Hudson Ridge, the essentials of a home, location, design, and space, come together with ease. Recently reimagined to capture natural light and a contemporary aesthetic, it offers a setting that is both open and inviting. Set on nearly five acres, the property has the character of a country estate. The main level is anchored by a spacious living room with a modern free standing fireplace and

    Abbie Carey Houlihan Lawrence Inc.

    34 Hudson Ridge, Garrison, NY 10524
  • 16 Nelson Ln, Garrison, NY 10524

    $678,500 Sold Aug 21, 2025

    • 1,164 Sq Ft
    • $583/SF
    • 75 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1972

    16 Nelson Ln, Garrison, NY 10524

    Charming updated Garrison home just steps to GUFS Prek-8 Blue Ribbon School. Lovely flat pasture like sunny 1-acre parcel on a quiet country dead-end dirt road with stream and bonus storage sheds. Move right in or bring your vision and renovate/expand & upsize to create your forever upstate dream home in the heart of much sought-after Garrison NY. Low yearly RE taxes of only $7,824

    Jeffrey Green Compass Greater NY, LLC

    16 Nelson Ln, Garrison, NY 10524
  • 1004 Old Albany Post Rd, Garrison, NY 10524
    1004 Old Albany Post Rd, Garrison, NY 10524
    1004 Old Albany Post Rd, Garrison, NY 10524
    /5

    $375,000

    • Land
    • 2.11 Acres
    • $177,894 per Acre

    1004 Old Albany Post Rd, Garrison, NY 10524

    Gorgeous approved lot on desirable Old Albany Post Rd. in the heart of Garrison! Property borders New York State land and adjacent to Fahnestock Park, with access to Catfish Pond. Private and wooded, but minutes from historic Cold Spring Village. Newly updated board of health approval for a four bedroom home. Driveway and curtain drains installed. Bring your building plans!

    Craig Roffman Houlihan Lawrence Inc.

    1004 Old Albany Post Rd, Garrison, NY 10524
  • 2 Forsonville Ln, Garrison, NY 10524

    $850,000 Sold Aug 19, 2025

    • 2,076 Sq Ft
    • $409/SF
    • 86 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1896

    2 Forsonville Ln, Garrison, NY 10524

    Welcome to Forsonville Lane—where history meets modern comfort.Dating back to the 1890s, Forsonville Lane was once home to some of Garrison’s earliest estates. This beautifully updated residence blends timeless charm with modern convenience, featuring an open floor plan and a newly renovated kitchen surrounded by windows.The home includes three bedrooms and a dedicated flex room, now

    Abbie Carey Houlihan Lawrence Inc.

    2 Forsonville Ln, Garrison, NY 10524
  • 1070 Route 9d, Garrison, NY 10524
    1070 Route 9d, Garrison, NY 10524
    1070 Route 9d, Garrison, NY 10524
    /47

    $4,995,000

    • 8 Beds
    • 7 Baths
    • 10,626 Sq Ft

    1070 Route 9d, Garrison, NY 10524

    Gothic Revival Country House.Welcome to the Hurst-Pierrepont Estate. This Gothic beauty, situated in the picturesque Hudson Valley is truly a one of a kind offering. The house completed in 1867, designed by Alexander Jackson Davis for Edwards Pierrepont as a country home, sits on almost 20 verdant acres with pool, patio, pond, perennial gardens and specimen trees. Preserving the home's

    Heather Fitzgerald Coldwell Banker Realty

    1070 Route 9d, Garrison, NY 10524
  • 25 Ferris Dr, Garrison, NY 10524

    $651,900 Sold Aug 15, 2025

    • 1,937 Sq Ft
    • $337/SF
    • 33 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1952

    25 Ferris Dr, Garrison, NY 10524

    Located in Continental Village, this beautifully refreshed 3 BR/2 BA home boasts a kitchen w SS appliances and quartz countertops, a primary bathroom with his & hers vanities, and a large living space with an open floor plan and fireplace, perfect for entertaining. The community offers a clubhouse, tennis courts, and lake while being perfectly nestled away from the bustle. Close to Route 9 for

    Komal Garewal Winwin Realty

    25 Ferris Dr, Garrison, NY 10524
  • 11 Hustis Rd, Cold Spring, NY 10516
    11 Hustis Rd, Cold Spring, NY 10516
    11 Hustis Rd, Cold Spring, NY 10516
    /24

    $627,000

    • 4 Beds
    • 2 Baths
    • 1,720 Sq Ft

    11 Hustis Rd, Cold Spring, NY 10516

    Welcome to this vintage charmer – the perfect mountain retreat or second home! Nestled on a private lot, this warm and welcoming residence offers comfortable living and timeless appeal. Relax and entertain with ease thanks to a generous pool deck and abundant outdoor space. Step inside to an inviting main living area, where an authentic wood-burning fireplace creates a cozy focal point for

    Evelyn Jean Delere Christie's Int. Real Estate

    11 Hustis Rd, Cold Spring, NY 10516
  • 1051 Old Albany Post Rd, Garrison, NY 10524

    $904,000 Sold Aug 13, 2025

    • 1,672 Sq Ft
    • $541/SF
    • 16 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1970

    1051 Old Albany Post Rd, Garrison, NY 10524

    Privately situated on almost 5 serene acres, on one of the most sought after and idyllic country roads in Garrison, this charming 3 bedroom 3 bath dutch gambrel center chimney colonial is an ideal find for those seeking serenity without sacrificing convenience. The main floor welcomes you into a light bright living room with windows on three sides, wood burning fireplace, full bath and first

    Melissa Carlton Houlihan Lawrence Inc.

    1051 Old Albany Post Rd, Garrison, NY 10524
  • 67 Angels Way, Garrison, NY 10524
    67 Angels Way, Garrison, NY 10524
    67 Angels Way, Garrison, NY 10524
    /38

    $2,800,000

    • 4 Beds
    • 5 Baths
    • 4,277 Sq Ft

    67 Angels Way, Garrison, NY 10524

    Wooded retreat meets modern comfort in this breathtaking Garrison home, perched atop a gently rolling hill on 5.3 private, park-like acres and abutted by state land. With its blend of soaring ceilings, warm woodwork, and sweeping Hudson River views, this home strikes a rare balance: grand in scale, yet deeply cozy—perfectly suited for both year-round living and weekend escapes. Double barn doors

    Melissa Carlton Houlihan Lawrence Inc.

    67 Angels Way, Garrison, NY 10524
  • 130 Putnam Rd, Garrison, NY 10524

    $580,000 Sold Aug 12, 2025

    • 1,680 Sq Ft
    • $345/SF
    • 23 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1960

    130 Putnam Rd, Garrison, NY 10524

    Welcome to this charming and meticulously maintained ranch-style home located in the desirable Continental Village community of Philipstown. Set on a peaceful street, this 3-bedroom, 1.5-bath home offers the perfect blend of comfort, convenience, and Hudson Valley charm. Step inside to discover a sun-filled interior showcasing gleaming hardwood floors, a spacious living room, and an updated

    Pauline Angrisani Coldwell Banker Realty

    130 Putnam Rd, Garrison, NY 10524
  • 43 Winston Ln, Philipstown, NY 10524
    43 Winston Ln, Philipstown, NY 10524
    43 Winston Ln, Philipstown, NY 10524
    /15

    $75,000

    • Land
    • 1.05 Acres
    • $71,429 per Acre

    43 Winston Ln, Philipstown, NY 10524

    Welcome to the beautiful town of Garrison NY- 43 Winston Lane—an exceptional opportunity to own a property in the heart of beautiful Putnam County. This picturesque 1.05-acre vacant lot is nestled in one of Garrison’s most tranquil and scenic areas, surrounded by nature and upscale residences. Located at the corner of Winston Lane and Upland Drive, the property offers privacy, a gentle slope, and

    Sharon Jett Houlihan Lawrence Inc.

    43 Winston Ln, Philipstown, NY 10524
  • 2792 Route 9, Cold Spring, NY 10516

    $610,000 Sold Aug 08, 2025

    • 1,300 Sq Ft
    • $469/SF
    • 21 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1943

    2792 Route 9, Cold Spring, NY 10516

    Imagine coming home to this perfectly enchanting, storybook cottage just up the road from Cold Spring Village! Set back amidst perennial cottage gardens, this Cape Cod charms on first sight, and as its extensive updates reveal themselves, your affection will only grow. This warmly refined home offers four flexible spaces with closets and a full bath on each floor, allowing for multiple bedroom,

    Claudia Dizenzo Hudson River Line Realty

    2792 Route 9, Cold Spring, NY 10516
  • 4 Treeline Cir Unit 4, Cold Spring, NY 10516
    4 Treeline Cir Unit 4, Cold Spring, NY 10516
    4 Treeline Cir Unit 4, Cold Spring, NY 10516
    /10

    $144,900

    • 2 Beds
    • 1 Bath
    • 570 Sq Ft

    4 Treeline Cir Unit 4, Cold Spring, NY 10516

    accepted offer 11/8/2025. A RARE FIND! 2015 mobile home in lovely coop community. 2hours notice no appointments after dark. Inside so light and bright with beautiful white cabinets, upgraded kitchen applicances including cooktop and dutch doors wall oven, tile backsplash. This is a wonderful home with lots of upgrades, that needs to be seen. Newer modern bathroom with large tile shower. Washer,

    ANITA CHESTER BHHS Hudson Valley Properties

    4 Treeline Cir Unit 4, Cold Spring, NY 10516
  • 14 Constitution Dr, Cold Spring, NY 10516

    $630,000 Sold Aug 06, 2025

    • 1,152 Sq Ft
    • $547/SF
    • 29 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1957

    14 Constitution Dr, Cold Spring, NY 10516

    Nestled in the picturesque village of Cold Spring, this delightful 3-bedroom, 2-bathroom single-family ranch offers the perfect blend of comfort, convenience, and natural beauty. Set on a level yard with lush gardens and a charming greenhouse, this home is ideal for those who love outdoor living and gardening.Inside, you’ll find a warm and welcoming layout with spacious bedrooms and two

    Elizabeth Koski Coldwell Banker Realty

    14 Constitution Dr, Cold Spring, NY 10516
  • TBD Sky Ln, Garrison, NY 10537
    TBD Sky Ln, Garrison, NY 10537
    TBD Sky Ln, Garrison, NY 10537
    /12

    $130,000

    • Land
    • 0.93 Acre
    • $139,785 per Acre

    TBD Sky Ln, Garrison, NY 10537

    Escape to Serenity in Garrison- tucked away on a private road, this stunning .93-acre property offers unparalleled privacy and breathtaking views. Surrounded by nature, yet just minutes from the train station and all local amenities, it's the perfect blend of seclusion and convenience. Whether you're looking to build your dream home or create a peaceful weekend retreat, this scenic parcel

    Amanda Wilcox eXp Realty

    TBD Sky Ln, Garrison, NY 10537
  • 5 Railroad Ave, Cold Spring, NY 10516

    $825,000 Sold Aug 04, 2025

    • 1,140 Sq Ft
    • $724/SF
    • 12 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1867

    5 Railroad Ave, Cold Spring, NY 10516

    Step back in time without sacrificing modern comforts in this beautifully preserved and thoughtfully updated 1867 brick home located in the picturesque village of Cold Spring, NY. Nestled on a quiet street just a short walk to the Metro-North train station, village shops, restaurants, and scenic Hudson River trails, this home blends history, convenience, and charm. Inside, you will find two

    Chia-Jung Dion Julia B Fee Sothebys Int. Rlty

    5 Railroad Ave, Cold Spring, NY 10516
    • 21 Red Oak Ln, Garrison, NY 10524
      21 Red Oak Ln, Garrison, NY 10524
      21 Red Oak Ln, Garrison, NY 10524
      /35

      Est $1,866,604 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 2,500 Sq Ft

      21 Red Oak Ln, Garrison, NY 10524

      21 Red Oak Ln, Garrison, NY 10524

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