Philipstown, NY Homes

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  $875,000 Pending

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

  1080 E Mountain Rd S, Cold Spring, NY 10516

  This exquisitely maintained four-bedroom, two-bathroom Colonial home offers a rare opportunity to own a turnkey equestrian retreat, combining classic architectural charm with thoughtful, high-end updates throughout. Nestled on a beautifully landscaped and tree-lined lot, the property exudes warmth, privacy, and rural elegance, making it an ideal sanctuary for both people and animals. Designed for

  

  Shaylene Neumann

  Houlihan Lawrence Inc.

  (845) 583-1298

  1080 E Mountain Rd S, Cold Spring, NY 10516
• Explore Philipstown

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  /9

  $2,700 per month

  Apartment for Rent

  2 Beds

  95 Main St, Cold Spring, NY 10516

  Located right on Main Street in the Middle of the Village of Cold Spring. 2 Bedroom 2 bathroom apartment is in a great location 4 blocks from the train station. Enjoy off street parking and laundry across the hall. It has a large eat in kitchen, a large master suite with private bathroom with tub, a full living room, second full bathroom, and second bedroom. Located on the second floor of the

  95 Main St, Cold Spring, NY 10516
• 

  $550,000 Sold Nov 26, 2025

  • 2,002 Sq Ft
  • $275/SF
  • 73 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1790

  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
• 

  Est $896,259 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,984 Sq Ft

  1551 Route 9, Garrison, NY 10524

  1551 Route 9, Garrison, NY 10524
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  $310,000

  • Land
  • 2.43 Acres
  • $127,572 per Acre

  106 Upland Dr, Garrison, NY 10524

  Wooded 2.43 Acres in Scenic Garrison – Build Your Dream HomeOpportunity awaits on this 2.43-acre wooded parcel in desirable Garrison, NY. With over 200 feet of road frontage and adjacent to a vacant lot, this raw land offers privacy and potential. Located in the Lakeland School District and just 5.8 miles from the Garrison train station for an easy NYC commute. Enjoy nearby Fahnestock State

  

  Noreen Parrell

  William Raveis Real Estate

  (845) 448-8372

  106 Upland Dr, Garrison, NY 10524
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  /6

  $1,800 per month

  • 1 Bed
  • 1 Bath
  • 1,000 Sq Ft
  • Apartment for Rent

  21 Armando Rd Unit B, Cold Spring, NY 10516

  1 Bedroom apartment in private home. Rent includes, heat, water, electric & cable. Move in ready, lovely engineered wood flooring, large open eat in kitchen and plenty of privacy. Just pack your bags and move right in. Credit report and references required. Apartment is on the lower level of the main home.

  Christine Colasurdo Garrison Realty Group

  21 Armando Rd Unit B, Cold Spring, NY 10516
• 

  $585,000 Sold Nov 18, 2025

  • 2,500 Sq Ft
  • $234/SF
  • 50 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1970

  600 Sprout Brook Rd, Putnam Valley, NY 10579

  Welcome to this spacious 4-bedroom, 2-bath Raised Ranch offering versatile living space and a beautiful backyard setting. The main level features a bright living room, open kitchen, dining area, and a generous family room that opens to a screened-in porch, perfect for relaxing or entertaining. You'll also find a primary bedroom, two additional bedrooms, and a full bath on this level. The walk-out

  Margherita Eccleston Houlihan Lawrence Inc.

  600 Sprout Brook Rd, Putnam Valley, NY 10579
• 

  Est $638,000 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,590 Sq Ft

  63 Horton Rd, Cold Spring, NY 10516

  63 Horton Rd, Cold Spring, NY 10516
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  /14

  $499,000 Pending

  • Land
  • 18.5 Acres
  • $26,973 per Acre

  87 Crest Rd, Philipstown, NY 10516

  Private 18.5-Acre Building Site in Cold Spring Surrounded by Protected LandAn exceptional opportunity to own 18.5 private acres in the heart of the Hudson Valley. Located in desirable Cold Spring and surrounded by protected land, this expansive parcel offers the perfect blend of seclusion and accessibility—just minutes from the vibrant artistic communities of Cold Spring and

  

  Steven Gray

  Compass Greater NY, LLC

  (845) 335-3907

  87 Crest Rd, Philipstown, NY 10516
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  /10

  $1,775 per month

  • 1 Bed
  • 1 Bath
  • 665 Sq Ft
  • Condo for Rent

  2560 U S 9 Unit B, Cold Spring, NY 10516

  Newly Renovated Large 1 Bedroom Apartment with Large Deck located in Cold Spring.

  2560 U S 9 Unit B, Cold Spring, NY 10516
• 

  $566,000 Sold Nov 14, 2025

  • 950 Sq Ft
  • $596/SF
  • 29 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1860

  7 Market St, Cold Spring, NY 10516

  This 1860s Cold Spring Village cottage is brimming with heart. Steps from the riverfront, Main Street, schools, and Metro North, this home makes village living effortless. Step inside to a sunlit living space where every detail tells a story - exposed ceilings with knotty pine beams, reclaimed hardwood floors, charming shiplap pine walls and a warmth you can feel the moment you walk through the

  Melissa Carlton Houlihan Lawrence Inc.

  7 Market St, Cold Spring, NY 10516
• 

  Est $774,707 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,295 Sq Ft

  1 Division St, Cold Spring, NY 10516

  1 Division St, Cold Spring, NY 10516
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  /28

  $515,000

  • 2 Beds
  • 2.5 Baths
  • 1,806 Sq Ft

  11 Revolution Rd, Cold Spring, NY 10516

  Prime Location! Experience the best of both worlds just 50 miles from Manhattan with relaxed condo living and outdoor amenities reminiscent of a country house. Conveniently situated between the charming village of Cold Spring and Fishkill, this well-lit two-bedroom unit features high ceilings and immediate access to hiking trails and open skies. Additional amenities include access to the

  

  Bill Hussung

  Robert A. McCaffrey Realty Inc

  (845) 470-6263

  11 Revolution Rd, Cold Spring, NY 10516
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  /24

  $6,500 per month

  • 6 Beds
  • 4.5 Baths
  • 4,900 Sq Ft
  • House for Rent

  76 Whippoorwill Pond Rd Unit 78, Garrison, NY 10524

  Private estate on almost 70 private acres. Minutes to railroad, schools, shopping and miles of hiking trails, (complete with your own private pond and tennis court). Ideal weekend retreat or full time residence. Entertain in the warmer months on your multi level decks with mountain/distant riverveiws. A rare home first time being offered as a rental. Call for additional details

  Edward Preusser A.D.Preusser, Inc.

  76 Whippoorwill Pond Rd Unit 78, Garrison, NY 10524
• 

  $1,125,000 Sold Oct 31, 2025

  • 3,630 Sq Ft
  • $310/SF
  • 23 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1890

  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
• 

  Est $1,333,139 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 3,840 Sq Ft

  26 Main St, Cold Spring, NY 10516

  26 Main St, Cold Spring, NY 10516
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  /2

  $3,250,000

  • 5 Beds
  • 7.5 Baths
  • 6,370 Sq Ft

  2010 Us-9, Garrison, NY 10524

  Discover the perfect blend of classic charm and modern luxury at The Garrison Estate. This exquisitely transformed 1930s Hudson Valley home was meticulously reinvented from top to bottom in 2023 and offers 6,800 square feet of alluring living space on 12.28 acres. The colonial center hall has been painstakingly renovated to keep its traditional charm and elegance while infusing many playful and

  LINDSAY ROTHMAN Compass Greater NY LLC

  2010 Us-9, Garrison, NY 10524
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  /36

  $3,400 per month

  • 2 Beds
  • 1 Bath
  • 1,700 Sq Ft
  • Condo for Rent

  3 Orchard Ln Unit Cold Spring NY rare find, Cold Spring, NY 10516

  A beautiful un-furnished rental in Cold Spring NY, surrounded by gardens and stunning views. Have morning coffee while watching the sun rise over the mountain view or take advantage of nice weather by having breakfast out on the large private deck. From the newly renovated bathroom, to the spacious open floor plan, this beautiful spacious rental is sure to please. Extra large closets,  big,

  3 Orchard Ln Unit Cold Spring NY rare find, Cold Spring, NY 10516
• 

  $3,411,000 Sold Oct 31, 2025

  • 4,935 Sq Ft
  • $691/SF
  • 55 Days On Market

  • 5 Beds
  • 7 Baths
  • Built 2002

  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
• 

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 980 Sq Ft

  5 Fourth St, Cold Spring, NY 10516

  5 Fourth St, Cold Spring, NY 10516
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  /24

  $849,000

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

  1136 Route 9d, Garrison, NY 10524

  Charming Historic Retreat in GARRISON/COLD SPRING- Just over an hour from Manhattan ! Beautifully renovated early 20th -century schoolhouse, now a stylish 3-bedroom , 2 bathroom haven. Nestled in the scenic Hudson Valley, this unique property features:A spacious open-concept eat-in kitchen perfect for entertaining Cozy wood-burning pellet fireplace for year around warmthInground heated

  Richard Healy Corcoran Country Living

  1136 Route 9d, Garrison, NY 10524
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  /24

  $6,000 per month

  • 4 Beds
  • 3 Baths
  • 2,616 Sq Ft
  • House for Rent

  376 Lane Gate Rd, Cold Spring, NY 10516

  Spectacular Hudson river views, beautiful grounds, in-ground pool and total privacy. 24 x 16 Living room w. fieldstone frplc, redwood paneling and 20 ft. of glass opening to covered porch. Family rm. w. wood burning stove which opens onto deck. FDR, Den or 1st flr. BR. w. bath. 4 BR's, 3 Bths. A Unique country retreat or full time private residence on 12 acres. Additional Information:

  Nora Preusser A.D.Preusser, Inc.

  376 Lane Gate Rd, Cold Spring, NY 10516
• 

  $950,000 Sold Oct 30, 2025

  • 2,696 Sq Ft
  • $352/SF
  • 116 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1973

  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
• 

  Est $1,206,601 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,656 Sq Ft

  28 Justins Way, Garrison, NY 10524

  28 Justins Way, Garrison, NY 10524
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  /20

  $950,000

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

  63 Manitou Station Rd, Garrison, NY 10524

  Gracefully set in the heart of Garrison, this beautifully updated c.1906 Cape blends original craftsmanship with fresh, modern design. Each room is filled with natural light and timeless detail - from the gable windows and hardwood floors to the built-in bookcases that frame a cozy wood-burning fireplace. With a versatile layout, this home invites you to settle in and stay awhile. The eat-in

  Melissa Carlton Houlihan Lawrence Inc.

  63 Manitou Station Rd, Garrison, NY 10524
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  /32

  $12,000 per month

  • 6 Beds
  • 4.5 Baths
  • 4,520 Sq Ft
  • House for Rent

  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
• 

  $710,000 Sold Oct 28, 2025

  • 2,312 Sq Ft
  • $307/SF
  • 89 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1964

  69 Clove Brook Dr, Cold Spring, NY 10516

  Welcome to 69 Clove Brook Drive, meticulously maintained well-loved ranch on a quiet cul de sac, situated on 1 plus acres with mature plantings, specimen trees and rock outcroppings in a beautiful tranquil setting; Nature enthusiasts will love this home as the property literally borders Fahnestock State park, a 14,000+ acres state park adjacent to your property; Cold Spring has an incredible

  Suzanne Welch Coldwell Banker Realty

  69 Clove Brook Dr, Cold Spring, NY 10516
• 

  Est $1,144,500 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 5,092 Sq Ft

  14 Orchard Ln, Cold Spring, NY 10516

  14 Orchard Ln, Cold Spring, NY 10516
• 

  

  /21

  $1,499,000

  • 3 Beds
  • 2 Baths
  • 3,528 Sq Ft

  3 Horsemens Trail, Cold Spring, NY 10516

  Endless possibilities! This family estate/compound is situated on 13+ private acres. The main home is of post & beam construction from a reclaimed 18th century home. Wide board Pine flooring throughout the home’s open floor plan. Bright natural light illuminates the main living area & kitchen. Living room features wood stove & cathedral ceilings. There are 2 generous sized bedrooms on main living

  Matthew McGroarty River Realty Services, Inc.

  3 Horsemens Trail, Cold Spring, NY 10516
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  /8

  $2,650 per month

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Apartment for Rent

  161 Main St, Cold Spring, NY 10516

  Very spacious 2nd floor 2Br apartment with a new kitchen with granite countertops, an updated bathroom, ample closets and washer/dryer in the building. Conveniently located to everything that makes the Village of Cold Spring so appealing. Off street parking for one car. Available Immediately.

  Jonathan Miller Joncar Realty Inc

  161 Main St, Cold Spring, NY 10516
• 

  $1,590,000 Sold Oct 28, 2025

  • 4,950 Sq Ft
  • $321/SF
  • 49 Days On Market

  • 2 Beds
  • 5 Baths
  • Built 1897

  55 Dicks Castle Rd, Garrison, NY 10524

  Live as if you are on vacation every day in this extraordinary 4,950 sq. ft. residence at the legendary Dick’s Castle in Garrison. From your 1,000 sq. ft. private balcony with unobstructed Hudson River Views, watch dazzling sunsets and sweeping panoramas that extend north toward the Shawangunk Ridge and south across Storm King & Bear Mountain. According to The New York Times, Dicks Castle is

  Lesli Uribe Corcoran Country Living

  55 Dicks Castle Rd, Garrison, NY 10524
• 

  Not Listed For Sale

  • 3 Beds
  • 4.5 Baths
  • 2,861 Sq Ft

  45 Manitou Rd, Philipstown, NY 10524

  45 Manitou Rd, Philipstown, NY 10524
• 

  

  /23

  $1,375,000

  • 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
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  /49

  $5,950 per month

  • 2 Beds
  • 3 Baths
  • 1,368 Sq Ft
  • House for Rent

  77 Lake Dr, Cold Spring, NY 10516

  Welcome to your enchanting lakeside haven in the Valhalla Highlands community, a retreat unlike any other. This historically restored lakefront home offers a seamless fusion of 1930’s nostalgia and contemporary luxury. Almost every room offers captivating vistas of the tranquil waters, inviting you to immerse yourself in the serene ambiance of lakeside living. The home features 2 bedrooms and 3

  Valerie Codino Keller Williams Realty Group

  77 Lake Dr, Cold Spring, NY 10516
• 

  $415,000 Sold Oct 27, 2025

  • 1,000 Sq Ft
  • $415/SF
  • 33 Days On Market

  • 1 Bed
  • 2 Baths
  • Built 1983

  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 walk-in

  Annpauline Creamer Houlihan Lawrence Inc.

  41 Winston Ln, Garrison, NY 10524
• 

  Est $725,344 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,373 Sq Ft

  27 Knollwood Ln, Cold Spring, NY 10516

  27 Knollwood Ln, Cold Spring, NY 10516
• 

  

  /28

  $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
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  $2,500 per month

  • 2 Beds
  • 1 Bath
  • 850 Sq Ft
  • Apartment for Rent

  70 Main St Unit 2, Cold Spring, NY 10516

  Cold Spring NY 2 Bedroom Apartment On Main St few Hundred feet to the train with shops, Restaurants close by. Plenty of Natural light, washer and dryer in unit, Small dogs considered .

  James Doorhy eRealty Advisors, Inc

  70 Main St Unit 2, Cold Spring, NY 10516
• 

  $250,000 Sold Oct 27, 2025

  • 1,206 Sq Ft
  • $207/SF
  • 40 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1945

  13 Old Postal Rd, Cold Spring, NY 10516

  This charming bungalow in the town of Cold Spring is perfect for a weekend retreat or year-round living. Just a short walk to local shops and restaurants, the home is also close to scenic state parks, art galleries, and museums that make Cold Spring so special. Enjoy the outdoors in all 4 seasons, and take advantage of the low property taxes. All of this, just a 90 minute drive grand Midtown

  Aidan Ruane David Ruane Realty Associates

  13 Old Postal Rd, Cold Spring, NY 10516
• 

  Est $472,036 Not Listed For Sale

  • 1 Bed
  • 1.5 Baths
  • 958 Sq Ft

  36 Healy Rd, Cold Spring, NY 10516

  36 Healy Rd, Cold Spring, NY 10516

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