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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  /9

  $2,300 per month

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

  42 Toc Dr Unit 605, Highland, NY 12528

  Property Id: 2218474Welcome 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

  42 Toc Dr Unit 605, Highland, NY 12528
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  /42

  $470,000 Sold Oct 09, 2025

  • 2,248 Sq Ft
  • $209/SF
  • 27 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1963

  20 Lauretta Dr, Highland, NY 12528

  Tucked away on a quiet dead-end road, set high with scenic mountain views, this well-kept Raised Ranch is ready for your next chapter in the Hudson Valley. Freshly painted and move-in ready, the home offers 3 bedrooms, 2 bathrooms, a wood-burning fireplace, and a fenced-in backyard. The updated kitchen and spacious, finished lower level—with oversized windows framing the views—provide comfort and

  Peter Ilani BHHS HUDSON VALLEY PROP-R

  20 Lauretta Dr, Highland, NY 12528
• 

  Est $604,010 Not Listed For Sale

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

  25 Lauretta Dr, Highland, NY 12528

  25 Lauretta Dr, Highland, NY 12528
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  /46

  $525,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,400 Sq Ft

  123 Vineyard Ave, Highland, NY 12528

  Charming 1900s Home with Character and Versatility! Step into timeless elegance with this beautifully preserved early 20th-century residence, ideally located just a few doors from the vibrant hamlet of Highland. Surrounded by quaint restaurants and shops, this home offers both historic charm and modern convenience. Exterior highlights include a wrap-around covered porch, a classic feature that’s

  Dawn Passante Coldwell Banker Village Green

  123 Vineyard Ave, Highland, NY 12528
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  /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
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  /38

  $380,000 Sold Oct 03, 2025

  • 2,700 Sq Ft
  • $141/SF
  • 18 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1992

  399 New Paltz Rd, Highland, NY 12528

  Spacious Raised Ranch with Endless Potential in Highland! Discover this large and versatile raised ranch, perfectly situated on a country road, set back for added privacy with the scenic Illinois Mountain as your backdrop. This home offers a generous layout and solid bones, just waiting for your personal touch. The finished lower level has been upgraded and provides a flexible space—ideal for

  Dawn Passante Coldwell Banker Village GreenN

  399 New Paltz Rd, Highland, NY 12528
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  /26

  Est $623,738 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,400 Sq Ft

  21 Spring Meadow Ct, Highland, NY 12528

  21 Spring Meadow Ct, Highland, NY 12528
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  /33

  $450,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,715 Sq Ft

  334 Pancake Hollow Rd, Highland, NY 12528

  With 3 bedrooms, 2 full bathrooms, and 2,715 square feet of flexible living space, this turnkey home is ready for you to move right in and make it your own. At the heart of the home is a spacious open-concept kitchen and living room — perfect for everyday living and effortless entertaining. The generously sized primary suite offers both privacy and potential, with space to add an additional

  Leigh Wagner-Quintana Keller Williams Realty HV Nort

  334 Pancake Hollow Rd, Highland, NY 12528
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  /6

  $1,800 per month

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

  109 Grand St Unit B, Highland, NY 12528

  Property Id: 2238041Updated 2 bedroom, 1 bath upstairs unit available at 109 Grand St, Unit B, Highland, NY. This freshly renovated apartment features a modern kitchen, bright living space, and convenient access to New Paltz, Poughkeepsie, and the Mid-Hudson Bridge.

  109 Grand St Unit B, Highland, NY 12528
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  /14

  $308,500 Sold Sep 30, 2025

  • 946 Sq Ft
  • $326/SF
  • 27 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 2004

  329 Gregory Ct Unit 509, Highland, NY 12528

  Pictures have been virtually staged for inspiration.This fully renovated 2-bedroom condominium, which features a spacious home office, is both sophisticated and stylish. Located on the second floor, it includes a washer and dryer, as well as a terrace that overlooks lush wooded areas. The property boasts desirable amenities such as a pool, tennis courts, a clubhouse, a basketball court, a dog

  Nancy Senescu Bella NS Properties LLC

  329 Gregory Ct Unit 509, Highland, NY 12528
• 

  Est $488,639 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,750 Sq Ft

  799 State Route 44 55, Highland, NY 12528

  799 State Route 44 55, Highland, NY 12528
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  /49

  $419,000 Pending

  • 4 Beds
  • 2 Baths
  • 2,128 Sq Ft

  307 Vineyard Ave, Highland, NY 12528

  Classic 1900 Farmhouse with Timeless Charm - 4 Beds, 2 Baths on One Acre Nestled on residential-level farmland, you step into the charm of yesteryear with this sunlit 1900 farmhouse. Enjoy rich woodwork, a welcoming layout, hardwood floors just waiting to be refinished. Four floors offer 4 bedrooms, 2 full baths, 2 additional rooms on the second floor offer incredible expansion opportunities,

  Debra Dooley BHHS HUDSON VALLEY PROP-NP

  307 Vineyard Ave, Highland, NY 12528
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  /7

  $1,850 per month

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

  499 Ny-299 Unit 2B, Highland, NY 12528

  Property Id: 2238572Check out this beautiful and affordable apartment in a quiet part of Highland overlooking the water! Did I mention that everything is included? Explore this apartment in the beautiful Highland woods housing community! This one will not last, reach out now!

  499 Ny-299 Unit 2B, Highland, NY 12528
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  /38

  $1,295,000 Sold Sep 26, 2025

  • 2,900 Sq Ft
  • $447/SF
  • 20 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1983

  110 Bellevue Rd, Highland, NY 12528

  Paradise retreat with breathtaking panoramic water views of the Hudson River from every room. This impeccably renovated home has spared no expense, featuring Caesarstone throughout its generous floor plan and top-of-the-line Sub-Zero, Wolf, and Viking appliances in a dream kitchen. The open layout is perfect for entertaining or simply enjoying the stunning views as ships pass by. An abundance of

  Nancy Senescu Bella NS Properties LLC

  110 Bellevue Rd, Highland, NY 12528
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  /11

  Est $438,417 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,420 Sq Ft

  269 Tuckers Corners Rd, Highland, NY 12528

  269 Tuckers Corners Rd, Highland, NY 12528
• 

  

  /23

  $425,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,516 Sq Ft

  25 Mile Hill Rd, Highland, NY 12528

  Tastefully updated 4 bedroom, 2 bath raised ranch loaded with designer finishes. Spacious kitchen w/center island, quartz counters & stainless appliances flows seamlessly to living room, creating a perfect layout for entertaining. Three main level bedrooms and remodeled bathroom. Lower level includes fourth bedroom/family room, updated bathroom, laundry room, mudroom & large storage room.

  Dan Axtmann BHHS Hudson Valley Properties

  25 Mile Hill Rd, Highland, NY 12528
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  /18

  $2,500 per month

  • 2 Beds
  • 1 Bath
  • 1,377 Sq Ft
  • Townhouse for Rent

  17 Troy Ln, Highland, NY 12528

  Great townhome ready for rent immediately in a quiet neighborhood with welcoming neighbors. Very safe neighborhood for walking and riding bikes.5m from PK to NYC train station, 5m to Walk Over the Hudson and rail trail, 5m walk to grocery store and banking amongst other stores.Entire house is freshly painted with brand new flooring throughout with a new bathroom and hot water

  17 Troy Ln, Highland, NY 12528
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  $465,000 Sold Sep 25, 2025

  • 1,890 Sq Ft
  • $246/SF
  • 36 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 1928

  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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  Est $526,986 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,928 Sq Ft

  41 Jenkins Ln, Highland, NY 12528

  41 Jenkins Ln, Highland, NY 12528
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  /32

  $459,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,418 Sq Ft

  57 Mayer Dr, Highland, NY 12528

  Stunning Contemporary Split level. The perfect home for entertaining. Open concept living room, kitchen, dining area. Hardwood floors as seen. All new carpeting in bedrooms, Great room, and finished basement. Two fireplaces, one woodburning in family room, gas fireplace in Great room. Multi-level decks overlooking lush backyard with a woodburning pizza oven, concrete pad perfect for firepit. A

  CAROLYN DE MICHELE

  57 Mayer Dr, Highland, NY 12528
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  /6

  $1,800 per month

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

  1 Orchard Hills Cir, Highland, NY 12528

  For Rent – Beautiful 1BR Townhome in Highland, NY! Orchard Hill Cir, Unit 1B, Highland, NY 12528 – $1,800/monthKey Features:1 Bedrooms / ?? 1 BathroomsCat Friendly – Bring your feline friends!Heat & Hot Water INCLUDEDBright, spacious layout with plenty of natural lightWell-maintained & move-in ready

  1 Orchard Hills Cir, Highland, NY 12528
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  $537,500 Sold Sep 22, 2025

  • 2,342 Sq Ft
  • $230/SF
  • 81 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2005

  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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  Est $344,267 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,152 Sq Ft

  6 Mandia Ln, Highland, NY 12528

  6 Mandia Ln, Highland, NY 12528
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  /75

  $569,000 Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,270 Sq Ft

  93 Glen Rock Cir, Highland, NY 12528

  Move in Colonial shows pride of ownership. Set beautifully on 1.4 acres this 4 bedroom 2.5 bath stunner boasts modern kitchen with granite countertops custom cabinets and center island. It's open floorplan great room gives ample room for kitchen dining or cozying around the gas fireplace. For more formal dining there is a dining room. The entire first floor has equisite hardwood flooring From

  Terry Spiesman Weichert, REALTORS The Spiesma

  93 Glen Rock Cir, Highland, NY 12528
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  /6

  $1,800 per month

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

  109 Grand St Unit B, Highland, NY 12528

  Updated 2 bedroom, 1 bath upstairs unit available at 109 Grand St, Unit B, Highland, NY. This freshly renovated apartment features a modern kitchen, bright living space, and convenient access to New Paltz, Poughkeepsie, and the Mid-Hudson Bridge.Rent is $1,900/month.

  109 Grand St Unit B, Highland, NY 12528
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  $388,000 Sold Sep 19, 2025

  • 1,090 Sq Ft
  • $356/SF
  • 42 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1988

  16 Orchard Ln, Highland, NY 12528

  Welcome to your next home! This delightful 2-bedroom, 1-bath raised ranch is nestled in one of the area's most sought after neighborhoods, just minutes from local shops, restaurants, schools, and everything you need for convenient living.Step inside to find a bright and functional layout with plenty of natural light. The main level features two comfortable bedrooms and a cozy living

  Megan Krusen eXp Realty

  16 Orchard Ln, Highland, NY 12528
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  /28

  Est $268,055 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 895 Sq Ft

  355 Crescent Ave, Highland, NY 12528

  355 Crescent Ave, Highland, NY 12528
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  /6

  $199,900

  • Land
  • 11 Acres
  • $18,173 per Acre

  TBD Hawleys Corners Rd, Highland, NY 12528

  11 acres offering privacy and potential. The land is ideal for building a secluded estate, nature retreat located on a country road yet close to Route 299 leading to NYS Thruway. Mid Hudson Bridge 5 miles away. The parcels break down as follows:Parcel 1: 3.5 acresParcel 2: 4 acresParcel 3: 3.7 acresKey Features:Peaceful rural setting with minimal trafficSurrounded by woods

  Dawn Passante Coldwell Banker Village GreenN

  TBD Hawleys Corners Rd, Highland, NY 12528
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  $580,000 Sold Sep 18, 2025

  • 2,284 Sq Ft
  • $254/SF
  • 58 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1989

  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
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  /16

  Est $513,094 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,810 Sq Ft

  397 Crescent Ave, Highland, NY 12528

  397 Crescent Ave, Highland, NY 12528
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  /6

  $44,000

  • Land
  • 2.9 Acres
  • $15,172 per Acre

  TBD Hawleys Corners Rd, Highland, NY 12528

  This property is located in a desirable area that offers a balance of privacy and convenient access to key attractions in the Hudson Valley. Its location is situated just a few miles from the heart of downtown New Paltz and with Kingston also close by, you'll have easy access to all the vibrant shops, restaurants, and cultural scene. The site is also 6 miles from the Mid-Hudson Bridge and the

  Dominick Martorana Century 21 Alliance Rlty Group

  TBD Hawleys Corners Rd, Highland, NY 12528
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  /35

  $510,000 Sold Sep 16, 2025

  • 2,382 Sq Ft
  • $214/SF
  • 69 Days On Market

  • 5 Beds
  • 5 Baths
  • Built 1890

  20-22 Milton Ave, Highland, NY 12528

  Move-in ready and close to all the best amenities: This spacious two-unit Victorian in the heart of the village of Highland is just steps from popular restaurants and shops, and only minutes by car or bicycle to the Walkway Over the Hudson, New Paltz, and NYC-bound Metro-North service at Poughkeepsie. The first-floor unit features 2 bedrooms, 1 bath, a private deck, and 2 separate entrances,

  Hayes Clement Compass Greater New York, LLC

  20-22 Milton Ave, Highland, NY 12528
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  Est $543,348 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,872 Sq Ft

  745 State Route 44 55, Highland, NY 12528

  745 State Route 44 55, Highland, NY 12528
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  /32

  $365,000

  • 2 Beds
  • 2.5 Baths
  • 2,086 Sq Ft

  222 Sterling Place, Highland, NY 12528

  Welcome to this exceptional townhouse in a highly desirable community—spacious, thoughtfully updated, and filled with features you won’t easily find elsewhere.The first level offers a bright eat-in kitchen that opens into a combined dining and living area, creating a warm, connected space perfect for everyday living and entertaining.Upstairs, the second floor hosts a primary bedroom, a

  Dawn Passante Coldwell Banker Village Green

  222 Sterling Place, Highland, NY 12528
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  /36

  $470,000 Sold Sep 12, 2025

  • 1,449 Sq Ft
  • $324/SF
  • 25 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1930

  136 Chapel Hill Rd, Highland, NY 12528

  Beautifully blending timeless character with modern upgrades, this thoughtfully updated four-bedroom farmhouse offers the perfect balance of charm, comfort, and convenience. Original woodwork, wide-board flooring, and classic architectural details preserve the home's historic soul, while a series of recent renovations enhance everyday living. The fully updated kitchen and dining room are designed

  Sally Sprogis Four Seasons Sotheby's Int'l R

  136 Chapel Hill Rd, Highland, NY 12528
• 

  Est $405,145 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,982 Sq Ft

  683 State Route 44 55, Highland, NY 12528

  683 State Route 44 55, Highland, NY 12528
• 

  

  /17

  $245,000

  • 2 Beds
  • 2 Baths
  • 1,456 Sq Ft

  16 Trout Brook Ln, Highland, NY 12528

  Beautiful Hudson Valley location encompassed by apple orchards, farms, colleges, yet still close to trains and airports. Immaculate 2017 1456 sq. ft. manufactured home includes central air, forced hot air propane heat, stainless steel appliances, front and side porches, and large shed with electric. Upgrades include custom walk-in closet, Rapid Wall insulated skirting with side access door, vinyl

  Lisa Cozzolino Cronin & Company Real Estate

  16 Trout Brook Ln, Highland, NY 12528
• 

  $500,000 Sold Sep 12, 2025

  • 1,560 Sq Ft
  • $321/SF
  • 59 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2018

  290 Tuckers Corners Rd, Highland, NY 12528

  Discover the perfect blend of comfort, convenience, and potential in this well-maintained ranch-style home, built just eight years ago and nestled on 15 subdividable, buildable acres in Highland, NY. Whether you’re a builder, investor, or simply seeking a peaceful retreat with room to expand, this property is an exceptional find. The move-in ready home features central air, a heat pump, and a

  Virginia Corbett eXp Realty

  290 Tuckers Corners Rd, Highland, NY 12528
• 

  Est $397,894 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,128 Sq Ft

  36 Pancake Hollow Rd, Highland, NY 12528

  36 Pancake Hollow Rd, Highland, NY 12528

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