Highland, NY Homes

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  /21

  $369,000 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 1,707 Sq Ft

  38 Roxanne Blvd, Highland, NY 12528

  Opportunity knocks with this three bedroom, two bathroom split ranch situated on one acre, on a quiet cul-de-sac road. Beautiful hardwood floors and desirable floor plan. Bring your vision as this home is full of potential! The lower level walkout area of the home is finished with a full bathroom. Conveniently located just minutes to the Village of New Paltz or Poughkeepsie Bridge.

  

  Amy Hawks

  Berardi Realty

  (845) 203-3694

  38 Roxanne Blvd, Highland, NY 12528
• 

  

  

  /13

  $2,300 per month

  Trailview Place

  2 Beds

  42 Toc Dr, Highland, NY 12528

  Welcome to your new home in the heart of Highland, NY! This apartment community offers comfort and convenience in a prime location. Situated just steps away from the scenic rail trail and the iconic Mid-Hudson Bridge, outdoor enthusiasts will love the easy access to biking, walking, and breathtaking views. If you're a commuter, the nearby train station provides a stress-free option for travel.

  42 Toc Dr, Highland, NY 12528
• 

  $51,000 Sold Oct 31, 2025

  • Land
  • 5.04 Acres
  • $10,119 per Acre

  • 361 Days On Market

  0 Summit Dr Unit KEYH6318306, Highland, NY 12732

  5+ acre lot in a gated community with lake rights to Timber Lake, come build your dream home! Enjoy fishing, swimming, boating on a beautiful private lake in a gated community.

  Dawn Payne Payne Team LLC

  0 Summit Dr Unit KEYH6318306, Highland, NY 12732
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  /34

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 740 Sq Ft

  73 New Paltz Rd, Highland, NY 12528

  73 New Paltz Rd, Highland, NY 12528
• 

  

  

  /3

  $469,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  224 Vineyard Ave, Highland, NY 12528

  Ready-To-Build 3-Bedroom Home with Mountain Views - Prime Location Near TownThis won't last long ready to-built. Still time to customize the floor plan, pick colors, countertops and more. 3-bedroom, 2-bathroom home on a scenic .24-acre lot with stunning Illinois Mountain views. Perfectly situated just minutes from town, you'll enjoy close proximity to restaurants, the train station,

  

  Danielle Carlson-murphy

  Start Home Smart, Inc.

  (845) 581-7956

  224 Vineyard Ave, Highland, NY 12528
• 

  

  /12

  $2,600 per month

  • 2 Beds
  • 2.5 Baths
  • 1,200 Sq Ft
  • Apartment for Rent

  42 Maple Ave Unit 2, Highland, NY 12528

  Beautiful country setting, just up the street the Gunk House Resturant in Clintondale, houses this picturesque stately Victorian three family home. The available two bedroom offers a full galley kitchen, formal dining room, spacious living room with beamed ceiling, half bath and main bedroom and full bath on the main level. The second level touts two bedrooms and office (flex space) and full

  Laurie Dellavilla Miller Professional Realty Group

  42 Maple Ave Unit 2, Highland, NY 12528
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  /37

  $491,000 Sold Oct 31, 2025

  • 2,366 Sq Ft
  • $208/SF
  • 74 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 1983

  258 Martin Ave, Highland, NY 12528

  Major space meets major opportunity: This versatile 2-family home nestled on 2 sunny acres offers privacy plus big potential for comfortable living and extra income. Perfectly adaptable, you can rent both units, live in one while renting the other, or knock down a wall to create a spacious single-family residence. The first unit is an extra roomy, one-level home featuring three bedrooms and two

  Hayes Clement Compass Greater New York, LLC

  258 Martin Ave, Highland, NY 12528
• 

  Est $498,382 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,923 Sq Ft

  876 South St, Highland, NY 12528

  876 South St, Highland, NY 12528
• 

  

  /18

  $299,999 Pending

  • 2 Beds
  • 1 Bath
  • 1,336 Sq Ft

  22 Woodside Place, Highland, NY 12528

  Welcome to 22 Woodside Place, a beautifully updated 2-bedroom home full of charm and modern upgrades. Step inside to find a bright living space with bay windows, a refreshed kitchen featuring painted cabinets and all new appliances (2024), and a newly redone bathroom. This home is packed with improvements: central HVAC tucked into the attic for efficient heating and cooling, a new washer and

  MARIA FUERTES Redfin Real Estate

  22 Woodside Place, Highland, NY 12528
• 

  

  /15

  $1,500 per month

  Highland Crossing

  1 Bed

  3501 9w Route, Highland, NY 12528

  Welcome to Highland Crossing Community in Highland, New York! Our newly renovated one-bedroom apartments, nestled near the charming village of Highland, provide cozy living for those who love small-town life. Each unit is modern and comfortable, offering a touch of rustic charm. Located near the village, you'll have easy access to local shops, restaurants, and community events, while enjoying the

  3501 9w Route, Highland, NY 12528
• 

  $325,000 Sold Oct 30, 2025

  • 1,027 Sq Ft
  • $316/SF
  • 21 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1991

  422 Gregory Ct Unit 307, Highland, NY 12528

  TRULY NOTHING TO DO BUT MOVE IN! Welcome to this meticulously maintained upper-level end unit, where vaulted ceilings and skylights flood the space with abundant natural light, adding a sense of openness and refined elegance throughout. The seamless flow between the dining and living area exudes warmth and sophistication, offering an inviting space to unwind or entertain. A stunning, sleek eat-in

  Nancy Diehl Rita Levine Real Estate

  422 Gregory Ct Unit 307, Highland, NY 12528
• 

  Est $228,749 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,414 Sq Ft

  117 Half Moon Rd, Highland, NY 12528

  117 Half Moon Rd, Highland, NY 12528
• 

  

  /31

  $450,000

  • 4 Beds
  • 2 Baths
  • 1,428 Sq Ft

  10 Carly Dr, Highland, NY 12528

  Discover the perfect blend of comfort, convenience, and lifestyle in this beautifully maintained 4-bedroom, 2-bathroom single-level home, tucked away in a peaceful cul-de-sac in sought-after Highland, NY. Sitting on a full acre, this property offers endless possibilities space to entertain, relax, and enjoy outdoor living. Cool off all summer long in the above-ground pool, or take in the privacy

  Megan Krusen eXp Realty

  10 Carly Dr, Highland, NY 12528
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  /13

  $1,800 per month

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

  560 State Route 44 55 Unit D, Highland, NY 12528

  Discover your new home in this cozy 2 bedroom, 1 bathroom apartment located on the top floor behind the Mobile Gas Station in Highland, NY. Enjoy the convenience of having heat and hot water included in your rent. This apartment is available immediately and boasts a prime location with easy access to local amenities. Don't miss out on this great opportunity! Contact us today to schedule a viewing.

  Anthony Minieri Keller Williams Hudson Valley

  560 State Route 44 55 Unit D, Highland, NY 12528
• 

  $50,000 Sold Oct 27, 2025

  • Land
  • 5.63 Acres
  • $8,881 per Acre

  • 51 Days On Market

  Lot#26 Timber Lake Dr, Highland, NY 12792

  Build your dream home on Private 5 acre parcel with lake rights down the road in lovely gated community. Lake access, beach, boating, fishing within walking distance from the Lake.

  Jane Panico Realty Promotions Inc

  Lot#26 Timber Lake Dr, Highland, NY 12792
• 

  

  /28

  Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 1,866 Sq Ft

  16 Washington Ave, Highland, NY 12528

  16 Washington Ave, Highland, NY 12528
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  /36

  $565,000

  • 2 Beds
  • 2.5 Baths
  • 1,364 Sq Ft

  5 Willow Dock Rd, Highland, NY 12528

  A truly special home that seamlessly blends the charm of its century-old origins with modern-day comfort and design. Tucked away on a quiet dead-end road, it offers sweeping Hudson River views from nearly every room, inviting you to experience the river’s beauty through all four seasons. Just steps from the water’s edge, this historic treasure provides a front-row seat to breathtaking sunrises

  Lindsay Rothman Compass Greater NY LLC

  5 Willow Dock Rd, Highland, NY 12528
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  /5

  $1,500 per month

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

  3501 Us-9w Unit 15, Highland, NY 12528

  Property Id: 2218543Welcome to Highland Crossing Community in Highland, New York! Our newly renovated one-bedroom apartments, nestled near the charming village of Highland, provide cozy living for those who love small-town life. Each unit is modern and comfortable, offering a touch of rustic charm. Located near the village, you'll have easy access to local shops, restaurants, and

  3501 Us-9w Unit 15, Highland, NY 12528
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  /43

  $240,000 Sold Oct 27, 2025

  • 2,314 Sq Ft
  • $104/SF
  • 109 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1896

  312 Crescent Ave, Highland, NY 12528

  A Romantic Restoration Opportunity | New Paltz NY Area 3BD | 2BA | Victorian w/ Carriage House/StudioLocated in the beautiful hamlet of Clintondale Tucked in the rolling farm country of the Hudson Valley, (lots of farms equals low taxes) just 90 minutes from NYC by car bus or train. Metro north and Amtrak 14 mins away this quintessential Victorian offers a rare opportunity to

  Machree Quaker The Machree Group, LLC

  312 Crescent Ave, Highland, NY 12528
• 

  

  /35

  Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,100 Sq Ft

  60 New Paltz Rd Unit 62, Highland, NY 12528

  60 New Paltz Rd Unit 62, Highland, NY 12528
• 

  

  /42

  $415,000

  • 3 Beds
  • 2 Baths
  • 1,547 Sq Ft

  41 New Paltz Rd, Highland, NY 12528

  Stop everything, this is the one! Perfectly situated on just under an acre, this quintessential brick Cape is the definition of small-but-mighty charm. Backing directly to the beloved Hudson Valley Rail Trail, this home offers that rare blend of classic character, modern updates, and an unbeatable location. Step inside to find a bright, welcoming kitchen with space to dine in, a formal dining

  Leigh Wagner-Quintana Keller Williams Hudson Valley

  41 New Paltz Rd, Highland, NY 12528
• 

  

  /34

  $2,900 per month

  • 3 Beds
  • 2.5 Baths
  • 1,550 Sq Ft
  • Apartment for Rent

  104 North Rd, Highland, NY 12528

  Available now! New construction duplex located right in Highland on North Road. Unit includes 3 bedrooms, 2 1/2 baths, full unfinished basement and approximately 1550 sq. ft. This home features stone front with large windows, lots of natural light, upgraded vinyl siding, luxury vinyl plank floors, 9 foot ceilings on first floor making this home feel more open. The craftsmen style interior will

  Marisa Bellacicco Century 21 Alliance Rlty Group

  104 North Rd, Highland, NY 12528
• 

  $300,000 Sold Oct 21, 2025

  • 946 Sq Ft
  • $317/SF
  • 62 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 2003

  660 Gregory Ct Unit 410, Highland, NY 12528

  Welcome to this beautifully updated 2nd-floor condo offering a perfect blend of comfort, convenience, and style. This spacious unit features 2 generously sized bedrooms plus a versatile flex room—ideal as a potential 3rd bedroom, home office, guest room, or creative space to suit your lifestyle. Recent updates throughout, including luxury vinyl plank flooring and fresh paint, this home exudes a

  John Durso Keller Williams Realty Partner

  660 Gregory Ct Unit 410, Highland, NY 12528
• 

  Not Listed For Sale

  • 9 Beds
  • 5 Baths
  • 1,000 Sq Ft

  50 John White Rd, Highland, NY 12528

  50 John White Rd, Highland, NY 12528
• 

  

  /26

  $599,000

  • 4 Beds
  • 2 Baths
  • 2,510 Sq Ft

  340 Vineyard Ave, Highland, NY 12528

  Step back in time with this spacious Victorian home full of original charm and character. Nestled on 41.10 acres of scenic land with mountain views. This property features a detached barn, 2 car garage and a classic summer kitchen. This property offers endless potential for restoration or creative retreat spaces. Inside you will find hardwood floors, birch cabinets with amazing stainless

  Ronnie Rebis Grist Mill Real Estate

  340 Vineyard Ave, Highland, NY 12528
• 

  

  /4

  $2,250 per month

  • 2 Beds
  • 1.5 Baths
  • 1,300 Sq Ft
  • Condo for Rent

  14 Orchard Hill Cir Unit 14, Highland, NY 12528

  Property Id: 2230771Explore the ideal sanctuary in Highland, New York! This vibrant community boasts a mix of 2 and 3 bedroom townhouses and 1 bedroom studios. Revel in the convenient proximity to local boutiques, dining establishments, and the full spectrum of Highland's amenities. Furthermore, the nearby rail trail beckons outdoor enthusiasts and nature admirers, creating an exceptional

  14 Orchard Hill Cir Unit 14, Highland, NY 12528
• 

  $758,000 Sold Oct 17, 2025

  • 3,253 Sq Ft
  • $233/SF
  • 107 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2005

  2 Fieldstone Ct, Highland, NY 12528

  Stunning colonial with contemporary flair gem boasts 4 large spacious bedrooms and 2.5 luxurious bathrooms, providing ample space for comfortable living. Step inside to discover a beautifully updated interior with modern finishes throughout. The 2-story living room creates an inviting space for gatherings, while the chef's kitchen features a sleek open layout, ideal for entertaining guests. Have

  Joseph Brown RE/MAX Real Property Group

  2 Fieldstone Ct, Highland, NY 12528
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  /35

  Est $494,759 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,972 Sq Ft

  27 Ose Rd, Highland, NY 12528

  27 Ose Rd, Highland, NY 12528
• 

  

  /24

  $575,000

  • 3 Beds
  • 1 Bath
  • 2,086 Sq Ft

  269 Orchard Rd, Highland, NY 12528

  Nestled among scenic orchards is this beautiful, updated nineteenth century farm house situated on almost 20 acres of beautiful pasture land and woods. This charming 3 bedroom home has a lovely full bath and plenty of living space for both humans and horses alike. The current owner keeps her horses on the property which is equipped with 2 run-in sheds and 7 shed row stalls which all have power

  Daniel Balassone VYLLA Home

  269 Orchard Rd, Highland, NY 12528
• 

  

  /12

  $2,200 per month

  • 2 Beds
  • 1 Bath
  • 1,654 Sq Ft
  • Apartment for Rent

  8 Marie Unit 2, Highland, NY 12528

  Picaresque Country Charmer is set on 2 plus acres of lush greenery. Updated and fresh appeal makes this spacious 2nd floor 2 Bedrooms a great choice. if you're looking to relocate this summer, you don't want to miss this one. offers an eat in kitchen with nook, living room, pantry and updated full bath. Each apartment has its own driveway and plenty of extra parking for guests in the common

  Michelle Ayala BHHS HUDSON VALLEY PROP-L

  8 Marie Unit 2, Highland, NY 12528
• 

  $450,000 Sold Oct 16, 2025

  • 1,633 Sq Ft
  • $276/SF
  • 87 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1940

  224 Martin Ave, Highland, NY 12528

  Welcome to this charming ranch style home featuring 3 cozy bedrooms. The primary bedroom has a large full bath, perfect for comfortable living. As you step inside you will be greeted by beautiful wood floors that flow seamlessly throughout the living spaces. The spacious kitchen boasts a charming breakfast area with sliders leading to the stone patio, making it the ideal spot for casual dining or

  Dawn Passante Coldwell Banker Village Green

  224 Martin Ave, Highland, NY 12528
• 

  Est $182,000 Not Listed For Sale

  847 N Chodikee Lake Rd, Highland, NY 12528

  847 N Chodikee Lake Rd, Highland, NY 12528
• 

  

  /33

  $499,900

  • 4 Beds
  • 2 Baths
  • 2,640 Sq Ft

  98 North Rd, Highland, NY 12528

  This charming 1900 farmhouse in Highland, New York, offers a comfortable and spacious living space with original wide custom moldings and beautiful oak hardwood flooring. Enjoy the beautiful sunlight in the fully finished sunroom. The kitchen is open with plenty of counter space and new appliances. Large dining area. The primary bedroom is on the first floor with windows facing three sides. enjoy

  Dawn Passante Coldwell Banker Village GreenN

  98 North Rd, Highland, NY 12528
• 

  

  /6

  $1,800 per month

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

  1 Orchard Hill Cir Unit 2D, Highland, NY 12528

  Property Id: 2218457Explore the ideal sanctuary in Highland, New York! This vibrant community boasts a mix of 2 and 3 bedroom townhouses and 1 bedroom studios. Revel in the convenient proximity to local boutiques, dining establishments, and the full spectrum of Highland's amenities. Furthermore, the nearby rail trail beckons outdoor enthusiasts and nature admirers, creating an exceptional

  1 Orchard Hill Cir Unit 2D, Highland, NY 12528
• 

  $355,000 Sold Oct 10, 2025

  • 2,444 Sq Ft
  • $145/SF
  • 74 Days On Market

  • 3 Beds
  • 6 Baths
  • Built 2000

  785 South St, Highland, NY 12528

  This unique property is like no other. Once you enter you will be surprised at the space inside as well as the 13 acres outside. Great opportunity for you to own a one of a kind property that you can make it your own by adding some TLC and vision to make your own oasis. Come see this diamond in the rough that is close to major highways and shoppping area.

  Brenda Watington W Manor LLC

  785 South St, Highland, NY 12528
• 

  Est $676,760 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,713 Sq Ft

  131 Baileys Gap Rd, Highland, NY 12528

  131 Baileys Gap Rd, Highland, NY 12528
• 

  

  /48

  $509,900

  • 3 Beds
  • 3 Baths
  • 1,824 Sq Ft

  62 Clearwater Rd, Highland, NY 12528

  Discover unparalleled privacy in this beautifully maintained home, set on its own serene acreage. Step inside to find a warm and inviting interior featuring hardwood floors throughout the main living areas and plush carpet in the bedrooms for comfort. The living room is anchored by a gorgeous stone fireplace, creating the perfect gathering spot for cozy evenings or entertaining guests. The

  Patricia Lucey Picture It Sold, LLC

  62 Clearwater Rd, Highland, NY 12528
• 

  

  /6

  $1,500 per month

  • 1 Bed
  • 1 Bath
  • 450 Sq Ft
  • Apartment for Rent

  560 State Route 44 55 Unit E, Highland, NY 12528

  Discover your new home in this cozy 1 bedroom, 1 bathroom apartment located on the top floor behind the Mobile Gas Station in Highland, NY. Enjoy the convenience of having heat and hot water included in your rent. This apartment is available immediately and boasts a prime location with easy access to local amenities. Don't miss out on this great opportunity! Contact us today to schedule a viewing.

  Anthony Minieri Keller Williams Hudson Valley

  560 State Route 44 55 Unit E, Highland, NY 12528
• 

  $329,000 Sold Oct 09, 2025

  • 1,121 Sq Ft
  • $293/SF
  • 78 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1800

  37 Maple Ave, Highland, NY 12528

  Freshly redone, Colonial style house 1,000 feet to the Hudson & Highland Landing Park. The open floor plan downstairs gives that airy fresh touch. Beautiful all new kitchen and appliances. Lots of windows. Upstairs, 3 spacious bedrooms and 2 full bathrooms. Make this opportunity your home and enjoy the beauties of the Hudson and this sweet contemporary home.

  Meyer Stoessel Keller Williams Hudson Valley

  37 Maple Ave, Highland, NY 12528
• 

  Est $766,779 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 3,275 Sq Ft

  326 Perkinsville Rd, Highland, NY 12528

  326 Perkinsville Rd, Highland, NY 12528

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