16

Philipstown, NY Homes for Sale with Acreage

Section Image
  • 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
  • 2680 U S 9, Cold Spring, NY 10516
    2680 U S 9, Cold Spring, NY 10516
    2680 U S 9, Cold Spring, NY 10516
    /29

    $3,800,000

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

    2680 U S 9, Cold Spring, NY 10516

    Minutes from Metro North and charming Cold Spring village, this equestrian paradise offers a rare blend of natural beauty and accessibility. Seller was meticulous in her assemblage of the property, from materials and construction to layout. With a state-of-the-art 16-stall banked metal barn with separate office/day room, indoor and outdoor arenas and an acre of fenced land ready for gardening,

    Melissa Carlton Houlihan Lawrence Inc.

    2680 U S 9, 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
  • 32 Winston Ln, Garrison, NY 10524
    32 Winston Ln, Garrison, NY 10524
    32 Winston Ln, Garrison, NY 10524
    /10

    $45,000

    • Land
    • 1.05 Acres
    • $42,857 per Acre

    32 Winston Ln, Garrison, NY 10524

    Tucked away in a peaceful, wooded setting, this 1.046-acre unimproved lot offers beautiful natural surroundings, mature trees, and the charm of a scenic backyard mountain stream. Located within the Continental Village community, this property provides a rare opportunity to create a custom home in a quiet, nature-filled environment. Enjoy seasonal mountain views, and the serenity of a natural

    Virginia Corbett eXp Realty

    32 Winston Ln, Garrison, NY 10524
  • 42 Dicks Castle Rd, Garrison, NY 10524
    42 Dicks Castle Rd, Garrison, NY 10524
    42 Dicks Castle Rd, Garrison, NY 10524
    /45

    $1,625,000

    • 3 Beds
    • 3 Baths
    • 2,700 Sq Ft

    42 Dicks Castle Rd, Garrison, NY 10524

    Rising above the Hudson Highlands with commanding views and unmistakable stone architecture, Dicks Castle remains one of the region’s most recognizable and storied landmarks. A Moorish style castle fashioned after Alhambra in Granada, Spain and situated on 26 wooded acres, the exterior features turrets, arches and courtyards surrounded by sculptures and stone walls well over 100 years old. This

    Kimberly Renzi Coldwell Banker Realty

    42 Dicks Castle Rd, Garrison, NY 10524
  • 50 Winston Ln, Philipstown, NY 10524
    50 Winston Ln, Philipstown, NY 10524
    50 Winston Ln, Philipstown, NY 10524
    /21

    $175,000

    • Land
    • 3.4 Acres
    • $51,471 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 Christie's Int. Real Estate

    50 Winston Ln, Philipstown, NY 10524
  • 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
  • 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
  • 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
  • 517 E Mountain Rd N Unit 515-517, Cold Spring, NY 10516
    517 E Mountain Rd N Unit 515-517, Cold Spring, NY 10516
    517 E Mountain Rd N Unit 515-517, Cold Spring, NY 10516
    /25

    $680,000

    • 3 Beds
    • 2 Baths
    • 1,619 Sq Ft

    517 E Mountain Rd N Unit 515-517, Cold Spring, NY 10516

    Discover 515-517 East Mountain Road North—a turnkey ranch perched atop the mountain, where timeless charm meets contemporary living on over 2 acres. This exceptional home artfully blends old-world details with modern additions, creating a perfect harmony of character and comfort.The main house has been beautifully renovated and expanded, featuring a brand-new 264 sq. ft. addition that

    Natalia Rathbauer Julia B Fee Sothebys Int. Rlty

    517 E Mountain Rd N Unit 515-517, Cold Spring, NY 10516
  • 16 Fox Hollow Ln, Garrison, NY 10524
    16 Fox Hollow Ln, Garrison, NY 10524
    16 Fox Hollow Ln, Garrison, NY 10524
    /31

    $1,595,000

    • 3 Beds
    • 3 Baths
    • 4,464 Sq Ft

    16 Fox Hollow Ln, Garrison, NY 10524

    Located in Garrison, NY, this country carriage-style house was once part of the estate of Samuel Sloan, a prominent railroad magnate who settled in the Hudson Valley during the 1850s.Charming and filled with natural light, the home has been meticulously renovated from top to bottom, seamlessly blending comfort, style, and functionality.The gardens, thoughtfully designed by the owner,

    Abbie Carey Houlihan Lawrence Inc.

    16 Fox Hollow Ln, Garrison, NY 10524
  • Lot 3 Woods Rd, Barryville, NY 10516
    Lot 3 Woods Rd, Barryville, NY 10516
    Lot 3 Woods Rd, Barryville, NY 10516
    /13

    $199,900

    • Land
    • 34.74 Acres
    • $5,754 per Acre

    Lot 3 Woods Rd, Barryville, NY 10516

    Looking for a spot to build your dream home? Look no further! This nice level wooded lot has a stream that runs through the front of the property. Located close to the towns of Barryville and Yulan. Just minutes from the majestic Delaware River. Schedule your appointment today!

    Brankica Curreri Eagle Valley Realty

    Lot 3 Woods Rd, Barryville, NY 10516
  • 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
  • 11 Cross Creek Rd, Cold Spring, NY 10516
    11 Cross Creek Rd, Cold Spring, NY 10516
    11 Cross Creek Rd, Cold Spring, NY 10516
    /43

    $799,999

    • 6 Beds
    • 3 Baths
    • 1,616 Sq Ft

    11 Cross Creek Rd, Cold Spring, NY 10516

    Nestled just off Route 9 and bordered by a gently rolling creek, this charming Dutch Colonial offers a rare opportunity to experience the natural beauty and quiet lifestyle Cold Spring, NY is known for. Set on over an acre of land, the home is surrounded by mature trees and open lawn, creating a private and peaceful retreat. The property features a versatile 4-bedroom residence with a 2-bedroom

    Andy Khan Silverside Realty LLC

    11 Cross Creek Rd, Cold Spring, NY 10516
  • 52 Justins Way, Garrison, NY 10524
    52 Justins Way, Garrison, NY 10524
    52 Justins Way, Garrison, NY 10524
    /5

    $375,000

    • Land
    • 7.77 Acres
    • $48,263 per Acre

    52 Justins Way, Garrison, NY 10524

    Gorgeous wooded lot on private mountain road! The perfect bucolic setting for your new Garrison home! 5 BR board of health approval in place. Bring your plans. Owner can GC project.

    Craig Roffman Houlihan Lawrence Inc.

    52 Justins Way, Garrison, NY 10524
  • 31 Ridgecrest Rd, Lake Peekskill, NY 10537
    31 Ridgecrest Rd, Lake Peekskill, NY 10537
    31 Ridgecrest Rd, Lake Peekskill, NY 10537
    /5

    $99,000

    • Land
    • 2.13 Acres
    • $46,523 per Acre

    31 Ridgecrest Rd, Lake Peekskill, NY 10537

    Set on over 2 acres, this exceptional building lot offers sun-drenched westerly exposure, postcard-worthy sunset views, and coveted access to Lake Peekskill. The parcel has already been cleared, providing a seamless start for construction and an advantageous layout for solar panels. With preserved land directly next door, you'll enjoy enduring privacy and a peaceful natural setting. Convenient to

    Peggy Jackson Houlihan Lawrence Inc.

    31 Ridgecrest Rd, Lake Peekskill, NY 10537
New York Putnam County Philipstown

Homes for Sale with Acreage in Philipstown, NY

Home Trends in Philipstown, NY

On average, homes in Philipstown, NY sell after 180 days on the market compared to the national average of 53 days. The median sale price for homes in Philipstown, NY over the last 12 months is $732,500, down 64% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$732,500
Median Single Family Sale Price
$732,500
Average Price Per Sq Ft
$579
Number of Homes for Sale
0
Last 12 months Home Sales
2
Months of Supply
0.00
Median List Price
$782,000
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
-64%
How to Buy a Home How to Finance a Home How to Sell a Home

In Philipstown, there are currently 16 homes for sale with acreage, providing ample space for homeowners to customize their living environment, whether for expansive gardens, outdoor entertaining, or enhanced privacy. Whether you're in search of a spacious family home with plenty of room to roam, a property ripe for development, or simply seeking space and tranquility, homes for sale with acreage in Philipstown, NY offer the flexibility to tailor your living experience to your preferences. Browse the selection of homes for sale with land in Philipstown and discover the potential and freedom that comes with owning your own piece of property.

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group