Highland, NY Homes

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  /21

  $450,000

  • 4 Beds
  • 2 Baths
  • 2,266 Sq Ft

  12 Woodside Place, Highland, NY 12528

  Come see this home that offers a perfect combination of charm, convenience, and community. This beautiful 4-bedroom, 2-bath home is full of character, featuring original hardwood floors and elegant French doors. The spacious living and dining areas are ideal for family gatherings, while the kitchen boasts stunning granite countertops, perfect for cooking and entertaining. Enjoy peaceful mornings

  Geraldine Gaudioso Century 21 Alliance-NP

  12 Woodside Place, Highland, NY 12528
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• 

  

  

  /46

  $2,400 per month

  • 2-3 Beds
  • 1 Bath
  • 1,464 Sq Ft
  • Condo for Rent

  244 Vineyard Ave Unit 1, Highland, NY 12528

  Fantastic first floor apartment in a three family home in Highland, NY.Apartment features:Three large bedrooms.Master bedroom has a lighted walk-in closet.One bedroom features a closet plus large bookshelves. One full bathroom upgraded with closet.Newly updated, large eat in kitchen with ceiling fan, with entrance to mudroom and back entrance to home.43 inch

  244 Vineyard Ave Unit 1, Highland, NY 12528
• 

  $370,000 Sold Jul 02, 2025

  • 1,956 Sq Ft
  • $189/SF
  • 108 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1987

  45 Cotter Rd, Highland, NY 12528

  Nestled on a picturesque 5.2-acre lot in Highland, NY, this charming 3-bedroom, 2.5-bathroom home offers a perfect blend of comfort and natural beauty. Spanning 1,956 sq ft, this inviting residence provides plenty of space for families or anyone looking for a serene retreat. The lush, expansive grounds feature open areas perfect for outdoor activities, gardening, or simply enjoying the tranquil

  Virginia Corbett eXp Realty

  45 Cotter Rd, Highland, NY 12528
• 

  Est $424,464 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,672 Sq Ft

  625 Milton Turnpike, Highland, NY 12528

  625 Milton Turnpike, Highland, NY 12528
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  /36

  $575,000

  • 3 Beds
  • 2.5 Baths
  • 2,242 Sq Ft

  17 Dogwood Knolls, Highland, NY 12528

  Incredible home with stunning renovations; this one of a kind raised ranch has over 2,200 sq.ft. featuring 3/4 bedrooms two and a half baths, PLUS bonus room and 2 car garage. Located in a peaceful setting of 3.3 private acres on the dead-end road; you get the "best of both worlds" a residential neighborhood that's also easily accessible to main roads, shopping and restaurants! This home has

  Gzim Hakanjin Coldwell Banker Realty

  17 Dogwood Knolls, Highland, NY 12528
• 

  

  /8

  $2,300 per month

  • 2 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Apartment for Rent

  718 Milton Turnpike Unit A, Highland, NY 12528

  Welcome to this charming and updated 2-bedroom, 2-bathroom home in the heart of Highland, NY! Featuring beautiful hardwood floors throughout, this cozy residence offers a perfect blend of comfort and convenience. Enjoy a spacious living room filled with natural light, a formal dining room ideal for gatherings, and a functional layout designed for easy living. The home has been thoughtfully

  Anthony Minieri Keller Williams Hudson Valley

  718 Milton Turnpike Unit A, Highland, NY 12528
• 

  

  /18

  $350,000 Sold Jul 01, 2025

  • 1,900 Sq Ft
  • $184/SF
  • 64 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1986

  25 Deller Rd, Highland, NY 12528

  Comfortable single level ranch home with 3 bedrooms and two full bathrooms. The one car garage has been converted into a beautiful light-filled family room for additional living space. Enjoy the large eat-in kitchen, just off the dining room. Sliders lead out to back deck with its private yard that's perfect for entertaining and summer barbecues. There's even a full unfinished basement for extra

  Dawn Passante Coldwell Banker Village GreenN

  25 Deller Rd, Highland, NY 12528
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  /4

  Not Listed For Sale

  TBD New Paltz Rd, Highland, NY 12528

  TBD New Paltz Rd, Highland, NY 12528
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  /22

  $425,000

  • 2 Beds
  • 1 Bath
  • 1,365 Sq Ft

  59 South St, Highland, NY 12528

  Charming 1900 Two-Story Farmhouse with Vintage Character... Step into timeless charm with this lovingly cared for two-story farmhouse, built circa 1900 and brimming with original character. Featuring authentic hardwood floors, this 2-bedroom home offers cozy living spaces, walk-in closets, and a woodstove perfect for those crisp Hudson Valley evenings. Enjoy peaceful mornings on the classic

  jeff farnell John J Lease REALTORS Inc

  59 South St, Highland, NY 12528
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  /29

  $1,800 per month

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • Condo for Rent

  203 Bedell Ave Unit 203 Bedell Apt B, Highland, NY 12528

  A quiet scenic neighborhood with a beautiful Hudson Valley view - close to New Paltz (thruway access), Poughkeepsie (train station). It is convenient for commuting to colleges. 15 minutes to the Walkway Over the Hudson.

  203 Bedell Ave Unit 203 Bedell Apt B, Highland, NY 12528
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  /35

  $680,000 Sold Jun 27, 2025

  • 1,656 Sq Ft
  • $411/SF
  • 20 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1974

  14 Tina Dr, Highland, NY 12528

  Nestled on a serene, wooded acre, this thoughtfully renovated 3-bedroom, 2-bathroom home offers a harmonious blend of mid-century charm and modern comfort. Its distinctive double gambrel roofline and A-frame silhouette set it apart, creating an inviting retreat just minutes from the quaint village of Highland and the vibrant communities of New Paltz and Poughkeepsie, providing easy access to

  Monica Schwerberg Compass Greater NY, LLC

  14 Tina Dr, Highland, NY 12528
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  /3

  Est $101,810 Not Listed For Sale

  30 Amanda Cir, Highland, NY 12528

  30 Amanda Cir, Highland, NY 12528
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  /49

  $509,000

  • 3 Beds
  • 1.5 Baths
  • 1,092 Sq Ft

  13 Sharon Dr, Highland, NY 12528

  Beautiful Ranch totally renovated ,new roof 2025 ,new siding 2025.Offer 3 bath and 1.5 Bath .Welcome to this charming ranch style home featuring 3 cozy bedrooms. As you step inside you will be greeted by beautiful commerce 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

  Drita Shala Howard Hanna Rand Realty

  13 Sharon Dr, Highland, NY 12528
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  /25

  $6,000 per month

  • 3 Beds
  • 2.5 Baths
  • 2,661 Sq Ft
  • House for Rent

  33 Maple Ave, Highland, NY 12528

  Beautiful, Hidden gem in Highland,NY. Offers complete privacy yet is minutes away from the quaint hamlet of Highland and the Walkway Over the Hudson State Park. Also nearby to New Paltz and Poughkeepsie. The stylish appointed home includes three bedrooms, two deck areas, a gas grill, and an outdoor woodturning fireplace. Comes furnished but may be negotiable.Tenant pays utilities. Lease could be

  Jonathon Romano-Chander BHHS HUDSON VALLEY PROP-NP

  33 Maple Ave, Highland, NY 12528
• 

  

  /23

  $678,734 Sold Jun 27, 2025

  • 1,754 Sq Ft
  • $387/SF
  • 25 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1998

  368 Plutarch Rd, Highland, NY 12528

  Privately sited among mature and flowering trees with plenty of open space to play is this well-maintained home located minutes to the vibrant towns of New Paltz and Highland. New Paltz School District. Upon entering you'll find gleaming oak floors, a light-filled open living room with wood-burning fireplace and dining area overlooking the back yard and large deck. The kitchen is central

  Helen Coyle Bergstein Helen Coyle Bergstein

  368 Plutarch Rd, Highland, NY 12528
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  /35

  Est $579,463 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,650 Sq Ft

  135 Chapel Hill Rd, Highland, NY 12528

  135 Chapel Hill Rd, Highland, NY 12528
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  /24

  $575,000

  • 4 Beds
  • 2.5 Baths
  • 2,342 Sq Ft

  27 Salk Dr, Highland, NY 12528

  Welcome to this beautifully maintained 4-bedroom, 2.5-bath Colonial perfectly blending timeless charm with modern conveniences. Located in a great commuter location, just minutes from the Mid-Hudson Bridge and local shopping, this home offers space, comfort, and unbeatable accessibility.The inviting living room features a cozy fireplace, ideal for relaxing evenings, while the family room and

  Margaret Thorne Keller Williams Hudson Valley

  27 Salk Dr, Highland, NY 12528
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  /18

  $1,425 per month

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

  28 Vineyard Ave Unit 28A, Highland, NY 12528

  NEWLY UPDATED 1 BED, 1 BATH FIRST FLOOR RANCH STYLE END UNIT RENTAL FEATURING A COZY AND OPEN CONCEPT FLOOR PLAN. ENJOY EASY TO MAINTAIN LUXURY VINYL FLOORING THROUGHOUT AND A FRESHLY PAINTED INTERIOR IN NEUTRAL PALETTE MAKE FOR EASY SELECTION OF YOUR STYLE OF DÉCOR. REFRESHED KITHEN OFFERS AMPLE CABINETRY WHILE THE FULL BATH IS HIGHLIGHTED BY ITS NEW VANITY AND FIXTURES. WELL PROPORTIONED

  Roadman Etienne BHHS Hudson Valley Properties

  28 Vineyard Ave Unit 28A, Highland, NY 12528
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  /14

  $392,000 Sold Jun 27, 2025

  • 1,720 Sq Ft
  • $228/SF
  • 119 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1900

  8 Marie, Highland, NY 12528

  Don't miss out on this incredible Opportunity! A Stunning Duplex in the Heart of Highland with 2 units, one with 2 bedrooms, 1 bath and one with 1 bedroom, 1 bath. First floor unit has open floor plan and both units have many upgrades such as mini splits, new bathrooms, updated plumbing, new roof and much more. This beautifully maintained home is a rare find. This home can be easily turned into a

  Angela Paul Century 21 Alliance-NP

  8 Marie, Highland, NY 12528
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  /2

  Est $97,519 Not Listed For Sale

  • Studio

  230 Chapel Hill Rd, Highland, NY 12528

  230 Chapel Hill Rd, Highland, NY 12528
• 

  

  /41

  $850,000

  • 5 Beds
  • 4 Baths
  • 3,230 Sq Ft

  7 Elliotts Ln, Highland, NY 12528

  Welcome to 7 Elliotts Ln, where space, comfort, and flexibility all come together—right in the heart of New Paltz. Set on a full acre, this 5-bedroom, 4-bath home offers over 3,200 square feet of living space, including a legal accessory apartment that's ideal for guests, extended living, or additional rental income.Step inside and you'll find gleaming new hardwood floors that run throughout

  Donna Brooks Compass Greater New York, LLC

  7 Elliotts Ln, Highland, NY 12528
• 

  

  /19

  $2,500 per month

  • 2 Beds
  • 1 Bath
  • 946 Sq Ft
  • Condo for Rent

  561 Gregory Ct, Highland, NY 12528

  Newly renovated 2 BR/ 1bath + den condominium ideally located minutes from the Mid-Hudson Bridge available for rent August 1, 2025. Minutes from major shopping and restaurants as well as the Walkway Over the Hudson State Park, major roadways and businesses in the Highland Central School District.

  John Quinn Quinn Realty Group Inc.

  561 Gregory Ct, Highland, NY 12528
• 

  

  /18

  $165,000 Sold Jun 25, 2025

  • Land
  • 13 Acres
  • $12,881 per Acre

  • 98 Days On Market

  274 Swartekill Rd, Highland, NY 12528

  If you have been looking for that beautifully wooded and secluded parcel of land to build your home in the country, look no further. Located on Swarte Kill Road, one of the most quiet and picturesque rural roads in the Town of Esopus, you'll find 12.81 acres of pristine conifer and hardwood Forest, which is largely bounded by stunning hand laid stone walls. The property is accessed by an old

  Brian Cafferty Halter Associates Realty

  274 Swartekill Rd, Highland, NY 12528
• 

  Not Listed For Sale

  • 2 Beds
  • 14,355 Sq Ft

  265 Fosler Rd, Highland, NY 12528

  265 Fosler Rd, Highland, NY 12528
• 

  

  /36

  $769,000

  • 4 Beds
  • 2.5 Baths
  • 3,253 Sq Ft

  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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  /12

  $1,995 per month

  • 2 Beds
  • 1.5 Baths
  • 650 Sq Ft
  • Apartment for Rent

  70 New Paltz Rd, Highland, NY 12528

  Welcome home to this townhouse style 2 bedroom 1 1/2 bath luxury apartment. Be the first to rent this beautiful space complete with hardwood floors, state of the art appliances, granite, huge windows letting in all the natural light you would enjoy. There is a washer/dryer connection in each unit. Plenty of lawn space for use and located within 5 miles to New Paltz and I 87 and the Mid-Hudson

  Pamela Di Martino Curasi Realty, Inc.

  70 New Paltz Rd, Highland, NY 12528
• 

  

  /41

  $390,500 Sold Jun 24, 2025

  • 1,547 Sq Ft
  • $252/SF
  • 42 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1900

  217 Hawley's Corners Rd, Highland, NY 12528

  Move-in ready and set on 2 private acres, this charming 3-bedroom, 2-bath home is perfect for summer gatherings. The modern eat-in kitchen boasts stainless steel appliances, crisp white cabinetry, and durable laminate flooring. A breakfast bar seamlessly connects the kitchen to the inviting living room, creating an open and functional layout. The split floor plan offers a spacious primary bedroom

  Angela Paul Century 21 Alliance-NP

  217 Hawley's Corners Rd, Highland, NY 12528
• 

  Est $212,500 Not Listed For Sale

  9 Elbow Ln, Highland, NY 12528

  9 Elbow Ln, Highland, NY 12528
• 

  

  /24

  $515,000

  • 4 Beds
  • 2.5 Baths
  • 2,184 Sq Ft

  19 Oak Crest Dr, Highland, NY 12528

  Blending comfort and style, this thoughtfully refreshed home is ready to welcome you. Major upgrades bring peace of mind, including a 50-year architectural roof (installed 2023) brand new bathrooms and beautiful new flooring throughout, including warm red oak hardwood that elevates the interior. The upstairs features all new carpeting, two fully renovated bathrooms, walk in primary closet, new

  Sandi Park Coldwell Banker Realty

  19 Oak Crest Dr, Highland, NY 12528
• 

  

  /9

  $2,300 per month

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

  70 New Paltz Rd Unit 1 A, Highland, NY 12528

  Welcome home to this 2 bedroom 1 bath sophisticated apartment located in Highland which is within 5 miles to New Paltz and Poughkeepsie. This is an ideal commuter location with I87 and the Poughkeepsie Train Station only a few miles away.This apartment features an open floor plan with gorgeous hardwood floors and wide doorways and an entry ramp making this handicap accessible. The fully

  Pamela Di Martino Curasi Realty, Inc.

  70 New Paltz Rd Unit 1 A, Highland, NY 12528
• 

  $260,000 Sold Jun 24, 2025

  • 1,040 Sq Ft
  • $250/SF
  • 141 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1963

  411 Vineyard Ave, Highland, NY 12528

  Three bedroom, one bathroom ranch with easy access to the Village of Highland! Cute brick home with covered front porch great for a hammock or rocking chair. Hardwood floors on the main level. Updated mechanicals. Basement area has additional rooms not included in finished square footage. Close to shopping, schools and amenities. Sold as-is. Buyer to pay NYS and any local transfer taxes.

  Brian Smith River Realty Services, Inc.

  411 Vineyard Ave, Highland, NY 12528
• 

  

  /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
• 

  

  /46

  $545,000

  • 5 Beds
  • 3 Baths
  • 2,024 Sq Ft

  191 Bedell Ave, Highland, NY 12528

  Welcome to 191 Bedell Ave in Highland, a move-in ready gem blending classic charm with modern updates! This beautifully maintained home features cathedral ceilings, hardwood floors, abundant natural light, and spacious living areas perfect for relaxing or entertaining. This sprawling raised ranch includes 5 bedrooms, 3 baths, and tons of living space on 1.46 Acres! Sit back and relax in the fully

  Michael Cahill HomeSmart Homes & Estates

  191 Bedell Ave, Highland, NY 12528
• 

  

  /17

  $5,000 per month

  • 4 Beds
  • 2 Baths
  • 2,506 Sq Ft
  • House for Rent

  241 Chapel Hill Rd, Highland, NY 12528

  Bring your suitcases to this spacious 4-bedroom, 2-bathroom single-family home for rent in Highland, NY. This furnished property features a modern kitchen with high-end appliances, a double-sided fireplace, a game room with a fireplace, and a seasoned porch overlooking a private in-ground pool. Situated on over 5 acres, enjoy peaceful living with convenient access to major roadways, shopping, and

  Xiomara Marrero eXp Realty

  241 Chapel Hill Rd, Highland, NY 12528
• 

  $50,000 Sold Jun 19, 2025

  • Land
  • 0.53 Acre
  • $94,340 per Acre

  • 222 Days On Market

  2 Elting Place, Highland, NY 12528

  Don't miss out on this unique vacant lot in the Historic Hamlet of Highland!! It is the last piece of land in the Hamlet of Highland that is in the Commercial/Business zone! OR you can develop it as a multi family with up to 4 townhome style homes! Water, sewer & natural gas are available to you! It is minutes to the Mid Hudson Bridge, the Walkway over the Hudson, New Paltz, the Thruway/87,

  Kathy Dawson Howard Hanna Rand Realty

  2 Elting Place, Highland, NY 12528
• 

  /2

  Est $565,068 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,353 Sq Ft

  278 Baileys Gap Rd, Highland, NY 12528

  278 Baileys Gap Rd, Highland, NY 12528
• 

  

  /27

  $399,900

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

  546 South St, Highland, NY 12528

  **A/O 7/19** CONTRACTS OUT Located in the heart of the Hudson Valley, this spacious 2,500 sq ft home in Highland blends classic charm with modern upgrades—perfect for those who crave room to grow and a connection to the outdoors.The first floor features a warm and inviting living room, a large dining area ideal for gatherings, an efficient kitchen ready for your personal touch, a private

  Lindsay Stevens eXp Realty

  546 South St, Highland, NY 12528
• 

  $405,000 Sold Jun 18, 2025

  • 1,248 Sq Ft
  • $325/SF
  • 51 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1987

  618 N Chodikee Lake Rd, Highland, NY 12528

  WOW! Stunning Renovation! This beautifully updated 3-bedroom 2 bath ranch, set on 1 acre on a country road, offers modern elegance throughout. The brand-new kitchen features quartz countertops, a marble backsplash, and new appliances. Gorgeous gleaming hardwood floors, updated lighting, and NEW bathrooms with the latest designer tiles. With NEW windows, vinyl siding, a full basement, and a

  Naomi Streicher Q Home Sales

  618 N Chodikee Lake Rd, Highland, NY 12528
• 

  Est $475,001 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
• 

  

  /50

  $450,000 Pending

  • 5 Beds
  • 4 Baths
  • 1,890 Sq Ft

  155 Tuckers Corners Rd, Highland, NY 12528

  Welcome to 155 Tuckers Corners Rd – a charming 1928 Craftsman Bungalow nestled on 3.37 private acres in Highland. This spacious home offers 5 bedrooms and 1.5 bathrooms in the main residence, along with a walk-out basement featuring a full in-law suite complete with its own kitchen, living room, bedroom, and full bath. Please note: the square footage does not include the finished lower-level

  Anais O'Connor Compass Greater NY, LLC

  155 Tuckers Corners Rd, Highland, NY 12528

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