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Philipstown, NY Houses for Sale

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  • /40

    $899,000 Open Sat 11AM - 1PM

    • 4 Beds
    • 2 Baths
    • 2,200 Sq Ft

    1080 E Mountain Rd S, Cold Spring, NY 10516

    This beautifully maintained four-bedroom, two-bath Colonial home is a rare find-a true turnkey equestrian retreat that seamlessly blends classic architectural charm with high-end modern updates. Situated on a tree-lined, professionally landscaped lot, this property offers privacy, serenity, and rural elegance, making it a welcoming haven for both people and animals. For the dedicated equestrian,

    Agent Photo

    Shaylene Neumann

    Houlihan Lawrence

    (845) 583-1298

    1080 E Mountain Rd S, Cold Spring, NY 10516
  • /38

    $1,495,000

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

    21 Private Way, Garrison, NY 10524

    Wooded retreat meets modern comfort in this spacious Garrison home, perfectly tucked away on nearly 5 private acres!This light-filled home is a true Hudson Valley hideaway! Set atop a gently rolling hill, the home’s dramatic profile immediately sets the tone: elevated, airy, and surrounded by nature.Upon entry into the main living area, you’re greeted by soaring ceilings, oversized windows, and

    Agent Photo

    Diana Polack

    Compass Greater NY, LLC

    (845) 261-0983

    21 Private Way, Garrison, NY 10524
  • /3

    $989,999

    • 3 Beds
    • 2.5 Baths
    • 2,394 Sq Ft

    6 Belvedere St E, Cold Spring, NY 10516

    Welcome to The Ellington, a stunning "To Be Built" 3 bedroom, 2 1/2 bath Contemporary Colonial in the charming Village of Cold Spring. This 3 bedroom, 2 .5 bath home offers hardwood floors throughout for timeless beauty and durability, an inviting family room w/wood burning fireplace that is open to a stylish eat-in kitchen with custom kitchen cabinetry, granite countertops and stainless

    Jonathan Miller Joncar Realty Inc

    6 Belvedere St E, Cold Spring, NY 10516
  • /45

    $1,100,000 Open Sat 10AM - 1PM

    • 3 Beds
    • 2 Baths
    • 1,836 Sq Ft

    107 Lane Gate Rd, Cold Spring, NY 10516

    Set along the quiet and scenic stretch of Lane Gate Road, 107 Lane Gate Road in Cold Spring, NY, offers an idyllic blend of refined country living and contemporary design. This architecturally striking three-bedroom, two-bathroom home is nestled on nearly two acres of peaceful, wooded land on one of the Hudson Valley’s most beloved country roads. Lane Gate is admired for its winding beauty,

    Ninfa Meehan Compass Greater NY, LLC

    107 Lane Gate Rd, Cold Spring, NY 10516
  • /36

    $988,000

    • 4 Beds
    • 3.5 Baths
    • 2,288 Sq Ft

    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
  • /23

    $1,450,000

    • 4 Beds
    • 4.5 Baths
    • 3,840 Sq Ft

    33 Victoria Dr, Cold Spring, NY 10516

    Modern Farmhouse recently built by a local craftsman. Situated on over 9 acres, this four-bedroom home has many custom details including 9' ceilings throughout, recently refinished wood flooring, custom trim and cabinetry, and built-in closets. Light and bright, the heart of the home is the open-concept chef’s kitchen with magnificent walnut island and matching walnut shelving, Viking appliances,

    Craig Roffman Houlihan Lawrence Inc.

    33 Victoria Dr, Cold Spring, NY 10516
  • /27

    $1,250,000

    • 5 Beds
    • 1.5 Baths
    • 2,806 Sq Ft

    24 Mountain Ave, Cold Spring, NY 10516

    Step back in time with this extraordinary 5-bedroom period home, built in 1897 and offering over 2,800 square feet of living space across three gracious floors. Located in the Historic Village of Cold Spring, this home is one of the largest you'll find within the Village—an increasingly rare opportunity.From the moment you enter, you're greeted by remarkably preserved original woodwork that

    Kathyrine Tomann Houlihan Lawrence Inc.

    24 Mountain Ave, Cold Spring, NY 10516
  • /43

    $1,275,000

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

    64 Paulding Ave, Cold Spring, NY 10516

    Located in the village of Cold Spring, a short walk away from the shops and restaurants of Main Street and the Metro North station, sits magical 64 Paulding, an 1890 rare, architectural gem. Tucked away on a uniquely large 1+ acre parcel with a level yard and in-ground pool, the expansive grounds, rare for a village property, create a private park-like setting adorned with mature trees, including

    Ann McBride-Alayon Hudson River Line Realty

    64 Paulding Ave, Cold Spring, NY 10516
  • /50

    $1,750,000

    • 4 Beds
    • 2.5 Baths
    • 3,604 Sq Ft

    1081 E Mountain Rd S, Cold Spring, NY 10516

    A dream come true! Cross the private bridge to your new future!! A serene & totally private retreat setting w/a view of the mountains & the tranquil sounds of your stream leading to your own majestic custom built, by owner, Queen Anne Victorian style home, w/numerous hidden features that enhances the quality of the home situated on 12.5 acres of lush Mother Nature!! Welcoming you is an expansive

    Maria Litrenta William Raveis Real Estate

    1081 E Mountain Rd S, Cold Spring, NY 10516
  • /27

    $1,475,000

    • 2 Beds
    • 3.5 Baths
    • 2,250 Sq Ft

    563 Route 9d, Garrison, NY 10524

    Escape to this breathtaking home in the heart of Garrison, NY, where tranquility meets convenience. Nestled atop over 2.5 acres of gorgeous maturely landscaped land, sits this charming 2/3 bedroom, 4-bathroom property offering expansive views of the majestic Hudson River, providing an idyllic backdrop for daily living. Located just 1.5 hours from NYC, it offers the perfect blend of serenity and

    Ryan Kominski Coldwell Banker Realty

    563 Route 9d, Garrison, NY 10524
  • /50

    $380,000

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

    41 Winston Ln, Garrison, NY 10524

    Charming Loft Home in Historic Continental Village – Garrison, NY Discover a rare gem in the heart of historic Continental Village: a unique one-bedroom loft home offering rustic character, creative space, and modern comfort—all set on a full acre just over an hour from NYC.Step inside and enjoy a light-filled interior with skylights, two full bathrooms, a separate laundry room, and a

    Annpauline Creamer Houlihan Lawrence Inc.

    41 Winston Ln, Garrison, NY 10524
  • /30

    $875,000 Open Sun 12:30PM - 2PM

    • 2 Beds
    • 2 Baths
    • 2,254 Sq Ft

    58 Winston Ln, Garrison, NY 10524

    Welcome to 58 Winston Lane in desirable Garrison NY. Lives like a 3bedroom with low yearly RE taxes of just $11,180. Hurry and close just in time to take advantage of the 2025-2026 school year in Garrison's coveted Blue Ribbon School District. Move right in to this fun, young contemporary with many recent upgrades such as wide plank oak flooring, Bosch Heat Pump HVACs, on-trend open kitchen with

    Jeffrey Green Compass Greater NY, LLC

    58 Winston Ln, Garrison, NY 10524
  • /47

    $3,250,000

    • 5 Beds
    • 7 Baths
    • 4,935 Sq Ft

    17 Half Moon Ridge, Cold Spring, NY 10516

    Welcome to your dream country house, nestled on a beautiful level five-acre property on a private road at Cold Spring's gateway to the Hudson Highlands. This expansive home offers the perfect blend of luxurious comfort and serene outdoor living, reminiscent of a private resort.Enjoy the ease of walkable access to Cold Spring’s charming shops, cafes, and cultural attractions, as well as

    Rudolf Vandommele Houlihan Lawrence Inc.

    17 Half Moon Ridge, Cold Spring, NY 10516
  • /46

    $950,000

    • 3 Beds
    • 3 Baths
    • 2,950 Sq Ft

    20 Deer Ridge Rd, Garrison, NY 10524

    Nestled on a serene, park-like 3.8-acre lot in beautiful Garrison, this custom-built Lindal Cedar Home offers a rare blend of natural beauty, privacy, and convenience. Home backs up to and has direct access to the NYS Appalachian Trail so no additional home can be built around this property. This 3-bedroom, 3-bath contemporary home is the perfect escape from the hustle and bustle of everyday

    Jean Ellen Baker RE/MAX Town & Country

    20 Deer Ridge Rd, Garrison, NY 10524
  • /42

    $625,000

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

    12 Valley Ln, Garrison, NY 10524

    Welcome to this beautifully updated and meticulously maintained raised ranch in the sought-after Continental Village community of Garrison, NY. Tastefully updated and maintained to perfection this home is set on a private and serene .81-acre lot, this home offers 3 spacious bedrooms, 2 full bathrooms, and a versatile office or guest space. The sun-filled living room flows seamlessly into the

    Maria Campanelli BHHS River Towns Real Estate

    12 Valley Ln, Garrison, NY 10524
  • /37

    $650,000

    • 3 Beds
    • 2 Baths
    • 1,873 Sq Ft

    440 Sprout Brook Rd, Garrison, NY 10524

    Located just one hour from NYC, this well-maintained home offers the perfect balance of convenience, comfort, and natural beauty. Set on a peaceful creekside lot, the property features an open-concept layout and timeless design details.Inside, the mid-century style kitchen opens into a bright living space ideal for everyday living or entertaining. The spacious primary bedroom is set apart

    Liudmila Lobeeva eXp Realty

    440 Sprout Brook Rd, Garrison, NY 10524
  • /31

    $829,000

    • 4 Beds
    • 2.5 Baths
    • 2,544 Sq Ft

    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
  • /25

    $519,000

    • 3 Beds
    • 1 Bath
    • 1,530 Sq Ft

    10 Hy Vue Terrace, Cold Spring, NY 10516

    MOTIVATED SELLER! ! ! 1500+ square feet of cozy charm comes 3 bedrooms and open plan kitchen and dining room with a comfy living room and fireplace. The home has wood flooring and central A/C and laundry. There is access from the kitchen to an enclosed porch and also access to a large patio decking with its own Tiki Bar for entertaining. It is the perfect location for commuting or for shopping.

    Patrick O'Sullivan LIMITED EDITIONS REALTY INC

    10 Hy Vue Terrace, Cold Spring, NY 10516
  • /31

    $920,000

    • 3 Beds
    • 2 Baths
    • 1,551 Sq Ft

    1136 Route 9d, Garrison, NY 10524

    Beautifully updated turnkey mini estate on just under an acre offers all of the easy maintenance of a condo without the HOA. Nestled in the heart of Garrison, this 3-bedroom, 2-bath home offers 1,551 square feet of inviting, light-filled living space with a warm, open-concept layout full of character. Enjoy cooking and entertaining in the recently renovated kitchen featuring brand new stainless

    Melissa Carlton Houlihan Lawrence Inc.

    1136 Route 9d, Garrison, NY 10524
  • /28

    $595,000

    • 4 Beds
    • 2.5 Baths
    • 2,002 Sq Ft

    20 Division St, Cold Spring, NY 10516

    Welcome to 20 Division Street, a captivating piece of history nestled in the heart of picturesque Cold Spring, NY. Built in 1790, this charming residence boasts 2,002 square feet of living space, featuring four spacious bedrooms and three bathrooms. Step outside to discover the beautifully updated exterior, complete with brand new pavers, modern siding, and a newly installed roof, ensuring both

    Debra Russo Serhant LLC

    20 Division St, Cold Spring, NY 10516
  • /43

    $950,000

    • 3 Beds
    • 2.5 Baths
    • 2,696 Sq Ft

    10 S Mountain Pond, Garrison, NY 10524

    Relax in a sanctuary for nature and the human spirit nestled in the Hudson Highlands. This unique artist’s home offers a serene 2-acre escape surrounded by babbling brooks, a pond, native ferns and moss, and protected green space—truly a “mini-Manitoga”! The multiple decks and winding pathways of the attractive two-story stone and shingle residence invite you into the heavenly sights, sounds and

    Ann McBride-Alayon Hudson River Line Realty

    10 S Mountain Pond, Garrison, NY 10524
  • /36

    $799,999

    • 4 Beds
    • 2.5 Baths
    • 4,170 Sq Ft

    24 Babbling Brook Ln, Cold Spring, NY 10516

    Experience the ultimate in privacy, serenity, and design at this one-of-a-kind retreat in the heart of Cold Spring. Nestled on a secluded lot, this beautifully crafted 4-bedroom, 3-bath residence features dramatic cathedral ceilings that elevate the space and frame stunning panoramic views of the surrounding natural landscape. Whether you're seeking a peaceful escape or a stylish full-time

    Luis Peralta Pena Real Broker NY LLC

    24 Babbling Brook Ln, Cold Spring, NY 10516
  • /32

    $2,790,000

    • 6 Beds
    • 4.5 Baths
    • 4,520 Sq Ft

    996 Route 9d, Garrison, NY 10524

    Step into a living legacy at “The Birches” a timeless masterpiece nestled in the heart of Garrison. Originally commissioned in 1882 by the Osborn family and designed by the legendary Gothic Revival master, Ralph Adams Cram, this architectural gem has been meticulously restored to its original glory to preserve its rich heritage while incorporating all of the comforts of contemporary living. From

    Melissa Carlton Houlihan Lawrence Inc.

    996 Route 9d, Garrison, NY 10524
  • /25

    $630,000

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

    11 Hustis Rd, Cold Spring, NY 10516

    Welcome to this charming 4-bedroom, 2-bathroom home on a private lot along Hustis Road in Cold Spring. Set back from the road, this peaceful retreat offers an in-ground pool, two spacious decks, and a breezeway connecting the two-car garage to the home—perfect for outdoor entertaining and relaxation. Inside, the open-concept kitchen and dining area have been beautifully renovated, leading into

    Nicole LaRosa Compass Greater NY, LLC

    11 Hustis Rd, Cold Spring, NY 10516
  • /29

    $4,970,000

    • 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
  • /31

    $1,750,000

    • 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
  • /5

    $1,400,000

    • 8 Beds
    • 4 Baths
    • 8,500 Sq Ft

    26 Coleman Rd, Philipstown, NY 10524

    This unique gem will not be available with the new owner until May of 2028. However, it can be held as an investment with the new owner until then. EIGHT Bedrooms, 2 full baths and 2.5 baths. Upgraded and expanded septic, Sprinklers and Generator included in sale. Interior Professional Photos to follow. Currently used as a Residential Facility. Purchase an investment as you await living in

    Angela Briante Briante Realty Group, LLC

    26 Coleman Rd, Philipstown, NY 10524
  • /37

    $2,800,000

    • 5 Beds
    • 5 Baths
    • 4,691 Sq Ft

    25 Red Oak Ln, Garrison, NY 10524

    Situated on two lots for a total of 15.5 acres, offering an abundance of privacy is only the beginning of what you will find as you enter the grounds. Welcome to 25 Red Oak Lane, an hour from Manhattan you will begin your tour with a Colonial home. This main house built in 1990, features 4 bedrooms, 2.5 baths, and updates during 2018-2021. Commence at the front walkway and find an expansive front

    Anna Hawley Howard Hanna Rand Realty

    25 Red Oak Ln, Garrison, NY 10524
  • /25

    $849,500

    • 4 Beds
    • 3 Baths
    • 2,860 Sq Ft

    103 Old Highland Turnpike, Garrison, NY 10524

    NOTE: Please , DON'T walk property WITHOUT PERMISSION. Surveillance cameras. This newly renovated and upgraded chalet home offers ambiance and charm from the moment you step through the door. Cathedral ceilings throughout the house give a sense of height and brightness. The large windows in every room bring the outside in. The stone fireplace is the centerpiece of the open-concept floor plan. A

    Qizhan Yao Realmart Realty LLC

    103 Old Highland Turnpike, Garrison, NY 10524
  • /40

    $799,000

    • 3 Beds
    • 2 Baths
    • 2,160 Sq Ft

    27 Maple Rd, Lake Peekskill, NY 10537

    True happiness awaits! Privacy and relaxation are the benchmarks of this Putnam Valley escape. Abundant greenery, and a lavish lawn provide the backdrop to your own year-round oasis. Take a dip in the refreshing pool and lay out on the new Trex deck. Fully updated living space sports a stylish open-concept layout, full of natural light and generous spaces. Formal living room w/picture window,

    Alice Regan Julia B Fee Sothebys Int. Rlty

    27 Maple Rd, Lake Peekskill, NY 10537

Why Live in Philipstown

Philipstown, New York, located 58 miles from New York City in the Hudson Valley, is known for its recreational opportunities and charming hamlets. The area features rolling, mountainous terrain with preserved land and extensive hiking trails, including the Hudson Highlands State Park with over 70 miles of trails and a section of the Appalachian Trail. Cold Spring and Garrison are the primary hamlets, with Cold Spring offering a bustling Main Street with shopping and dining, while Garrison is more residential and surrounded by nature. Points of interest include the Constitution Marsh and Audubon Center, Castle Rock Park, and the Boscobel House and Gardens, which hosts garden tours, festivals, and concerts. The area also has a thriving arts scene with the Garrison Art Center and the Depot Theater providing year-round workshops, exhibits, and live entertainment. Philipstown offers a variety of home styles, including Colonial Revival, split-level, and farmhouse, with options ranging from condos and townhouses to larger estate homes with Hudson River views. The Haldane Central School District and Garrison Union Free School District serve the area, both highly rated. For shopping and dining, Cold Spring features Angelina’s Pizza & Brew and Foodtown, while Garrison offers upscale dining at The Bird & Bottle Inn. The Hudson line provides convenient train access to New York City, and nearby hospitals include Montefiore St. Luke’s Cornwall and NewYork-Presbyterian Hudson Valley Hospital.

Home Trends in Philipstown, NY

Housing Trends

Median Sale Price
$3,875,000
Median Single Family Sale Price
$3,875,000
Average Price Per Sq Ft
$858
Number of Homes for Sale
1
Last 12 months Home Sales
25
Months of Supply
0.50
Median List Price
$3,900,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
15%
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