Highland, NY Homes

• 

  

  

  /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
• Selling your home? Sell it faster and for more with a Homes.com Boost.

  Learn More
• 

  

  

  /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
• 

  $315,000 Sold Aug 04, 2025

  7 Sunny Brook Cir, Highland, NY 12528

  • 3 Beds
  • 1.5 Baths
  • 1,160 Sq Ft
  • Built 1974

  Last Sold Summary

  • 15% Above List Price
  • $272/SF
  • 14 Days On Market

  Current Estimated Value $313,982

  Last Listing Agent Daniel Amone BHHS Hudson Valley Properties

  7 Sunny Brook Cir, 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
• 

  

  

  /35

  $4,600,000

  • 16 Beds
  • 10.5 Baths
  • 11,160 Sq Ft

  35 Washington Lake Rd, Highland, NY 12792

  Amazing One-of-a-kind Lakefront Home! This magnificent 11,000+ SF home features massive 2 story great room w/ stone fireplace, floating staircase & spiral staircase, commercial kitchen w/ walk in freezer & refrigerator, huge dining area/ game room/ wet bar. The home also offers 16 bedrooms, 10.5 baths, theater room, office, enclosed porch, huge patio featuring outdoor kitchen w/ wood fired pizza

  Jill Barnes Cabins & Canoes Real Estate

  35 Washington Lake Rd, Highland, NY 12792
• 

  

  /15

  $2,100 per month

  • 2 Beds
  • 1 Bath
  • 738 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

  Angel Ayala BHHS Hudson Valley Properties

  8 Marie Unit 2, Highland, NY 12528
• 

  

  /47

  $540,000 Sold Aug 27, 2025

  42 Bell Dr, Highland, NY 12528

  • 3 Beds
  • 3 Baths
  • 2,102 Sq Ft
  • Built 2001

  Last Sold Summary

  • 2% Below List Price
  • $257/SF
  • 59 Days On Market

  Current Estimated Value $539,725

  Last Listing Agent Leigh Wagner-Quintana Keller Williams Realty HV Nort

  42 Bell Dr, Highland, NY 12528
• 

  

  /9

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 728 Sq Ft

  53 Grand St, Highland, NY 12528

  53 Grand St, Highland, NY 12528
• 

  

  /19

  $138,500

  • 2 Beds
  • 1 Bath
  • 1,096 Sq Ft

  18 Hillside Place, Highland, NY 12528

  Looking for a great opportunity? Look no more! This property has tons of potential and is average in living space size for the neighborhood. It is located close to main roads with easy access to local amenities, such as shopping, banking, schools, and various eateries. Per our bpo/tax describe the property as a SFR (ranch) built in 1950. It has a GLA of approx. 1096 and has 2 bedrooms and 1bath,

  Christopher Rose Listing by REALHome Services & Solutions

  

  18 Hillside Place, Highland, NY 12528
• 

  /2

  $3,150 per month

  • 2 Beds
  • 1.5 Baths
  • 1,350 Sq Ft
  • House for Rent

  370 Red Top Rd, Highland, NY 12528

  Property Id: 2297263Beautiful 2 bedroom apartment separate dwelling with 2 entrances on a private Hudson River historical estate. Built and owned by Roosevelt cousins, the Howland Spencer family. Located on the west bank, directly across from FDR's. Spectacular views, floor to ceiling windows. We are seeking a quiet, respectful individual or couple. No smoking. No pets. Washer/dryer in

  370 Red Top Rd, Highland, NY 12528
• 

  $435,000 Sold Jun 05, 2025

  7 Dirks Terrace, Highland, NY 12528

  • 3 Beds
  • 2.5 Baths
  • 1,608 Sq Ft
  • Built 1985

  Last Sold Summary

  • 6% Above List Price
  • $271/SF
  • 19 Days On Market

  Current Estimated Value $429,574

  Last Listing Agent Nancy Senescu Bella NS Properties LLC

  7 Dirks Terrace, Highland, NY 12528
• 

  Est $506,016 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
• 

  

  /7

  $219,900

  • 2 Beds
  • 1 Bath
  • 1,096 Sq Ft

  18 Hillside Place, Highland, NY 12528

  Cozy two bedroom home within walking distance to the village shops and restaurants in Highland. Great location on a dead end street and great opportunity for the saavy buyer. Sold as-is. Buyer to pay NYS and any local transfer taxes. Offers with financing must be accompanied by pre-qual letter; cash offers with proof of funds. **Please see agent remarks for access, showing instructions and offer

  Brian Smith River Realty Services, Inc.

  18 Hillside Place, 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
• 

  

  /25

  $680,000 Sold Feb 24, 2025

  11 Palazzo Ln, Highland, NY 12528

  • 5 Beds
  • 3.5 Baths
  • 2,880 Sq Ft
  • Built 1991

  Last Sold Summary

  • 2% Below List Price
  • $236/SF
  • 11 Days On Market

  Last Listing Agent Jason Schobert eXp Realty, LLC

  11 Palazzo Ln, Highland, NY 12528
• 

  Est $225,311 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
• 

  

  /43

  $525,000 Pending

  • 4 Beds
  • 2 Baths
  • 2,368 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 GreenN

  123 Vineyard Ave, Highland, NY 12528
• 

  /2

  $3,500 per month

  • 3 Beds
  • 1.5 Baths
  • 1,600 Sq Ft
  • House for Rent

  267 Perkinsville Rd, Highland, NY 12528

  3 Br house 1 1/2 bath with 2 car garage and above ground swimming pool. Property and house is well maintained, clean. Washer and dryer included. No large dogs. sorry...#3,500 a month 1 month Security

  267 Perkinsville Rd, Highland, NY 12528
• 

  $385,000 Sold Sep 05, 2025

  21 Triangle of Clearwater Rd, Highland, NY 12528

  • 3 Beds
  • 1.5 Baths
  • 1,196 Sq Ft
  • Built 1960

  Last Sold Summary

  • 4% Above List Price
  • $322/SF
  • 10 Days On Market

  Last Listing Agent Dustin Leibowitz eXp Realty

  21 Triangle of Clearwater Rd, Highland, NY 12528
• 

  

  /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
• 

  

  /13

  $49,999 Pending

  • Land
  • 5 Acres
  • $10,000 per Acre

  0 Summit Dr Unit KEY842137, Highland, NY 12732

  Located in the exclusive gated community of Timber Lake Estates, this stunning 5-acre corner lot offers the perfect blend of privacy and natural beauty. Well-wooded and serene, the property boasts frontage on both Summit Drive and a quiet cul-de-sac on Deer Brook Drive, providing multiple access points and endless possibilities for a dream home or weekend retreat. Residents enjoy private access

  Kevin Fortuna K. Fortuna Realty, Inc.

  0 Summit Dr Unit KEY842137, Highland, NY 12732
• 

  $317,500 Sold Mar 31, 2025

  465 Plutarch Rd, Highland, NY 12528

  • 4 Beds
  • 2 Baths
  • 1,588 Sq Ft
  • Built 1950

  Last Sold Summary

  • 9% Below List Price
  • $200/SF
  • 16 Days On Market

  Current Estimated Value $360,797

  Last Listing Agent Rebecca Kaufman Q Home Sales

  465 Plutarch Rd, 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
• 

  

  /17

  $245,000 Pending

  • 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
• 

  

  /35

  $410,000 Sold Aug 08, 2025

  266 Swartekill Rd, Highland, NY 12528

  • 2 Beds
  • 2 Baths
  • 1,232 Sq Ft
  • Built 1952

  Last Sold Summary

  • 6% Above List Price
  • $333/SF
  • 32 Days On Market

  Current Estimated Value $407,466

  Last Listing Agent Danielle Carlson-murphy Start Home Smart, Inc.

  266 Swartekill Rd, Highland, NY 12528
• 

  

  /35

  Est $490,954 Not Listed For Sale

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

  27 Ose Rd, Highland, NY 12528

  27 Ose Rd, Highland, NY 12528
• 

  

  /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
• 

  $589,000 Sold Mar 14, 2025

  11 Bellevue Rd, Highland, NY 12528

  • 3 Beds
  • 3.5 Baths
  • 2,660 Sq Ft
  • Built 1978

  Last Sold Summary

  • 2% Below List Price
  • $221/SF
  • 102 Days On Market

  Current Estimated Value $604,643

  Last Listing Agent Dawn Passante Coldwell Banker Village Green

  11 Bellevue Rd, Highland, NY 12528
• 

  Est $157,000 Not Listed For Sale

  847 N Chodikee Lake Rd, Highland, NY 12528

  847 N Chodikee Lake Rd, Highland, NY 12528
• 

  

  /3

  $4,400,000

  • Land
  • 73.7 Acres
  • $59,701 per Acre

  00 Vineyard Ave, Highland, NY 12528

  Multi family property consisting of R-1/4, R-1/2 and R-1 zoning. Totaling 73 plus acres with two access points along Rte 44, Vineyard Avenue, in the Town of Lloyd, Ulster County, NY. One on the South end of the property with 150 feet of frontage along Vineyard Avenue and one on the North end of the property with 50 feet of frontage along Vineyard Avenue. Property slopes gently upward from road

  Robert Vitanza Rand Commercial

  00 Vineyard Ave, Highland, NY 12528
• 

  

  /49

  $417,865 Sold Jan 14, 2026

  307 Vineyard Ave, Highland, NY 12528

  • 4 Beds
  • 2 Baths
  • 2,128 Sq Ft
  • Built 1900

  Last Sold Summary

  • $196/SF
  • 71 Days On Market

  Last Listing Agent Debra Dooley BHHS HUDSON VALLEY PROP-NP

  307 Vineyard Ave, Highland, NY 12528
• 

  Est $749,500 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
• 

  

  /23

  $295,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft

  48 Sunny Brook Cir, Highland, NY 12528

  Welcome to 48 Sunny Brook Circle, where easy living meets effortless style. This sun-drenched, single-level end unit offers 1,056 square feet of comfort and charm, designed for those who crave simplicity without compromise. Step inside and you'll find a bright, open layout featuring a spacious eat-in kitchen, a welcoming living room, a private primary suite, and a versatile converted den (legal

  Leigh Wagner-Quintana Keller Williams Realty HV Nort

  48 Sunny Brook Cir, Highland, NY 12528
• 

  

  /19

  $325,000 Sold Jul 22, 2025

  183 Pancake Hollow Rd, Highland, NY 12528

  • 3 Beds
  • 1 Bath
  • 1,296 Sq Ft
  • Built 1958

  Last Sold Summary

  • 3% Below List Price
  • $251/SF
  • 151 Days On Market

  Current Estimated Value $339,908

  Last Listing Agent Dawn Passante Coldwell Banker Village GreenN

  183 Pancake Hollow Rd, Highland, NY 12528
• 

  Est $762,408 Not Listed For Sale

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

  326 Perkinsville Rd, Highland, NY 12528

  326 Perkinsville Rd, Highland, NY 12528
• 

  

  /13

  $500,000

  • Land
  • 11.5 Acres
  • $43,478 per Acre

  TBD Rt 9w, Highland, NY 12528

  Attention Investors! 11.5 acres located just minutes from the Mid-Hudson Bridge in desirable Highland, NY ready for developing. Ideally located on a high traffic state highway with over 1,000 feet of road frontage and tons of visibility. This lot sits directly across the highway from the future river front development named 'The Hudson Valley Wine Village' which is proposed to have 800 new

  John Quinn Quinn Realty Group Inc.

  TBD Rt 9w, Highland, NY 12528
• 

  $51,000 Sold Oct 31, 2025

  0 Summit Dr Unit KEYH6318306, Highland, NY 12732

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

  Last Sold Summary

  • 14% Below List Price
  • 361 Days On Market

  Last Listing Agent Dawn Payne Payne Team LLC

  0 Summit Dr Unit KEYH6318306, Highland, NY 12732
• 

  

  /49

  Est $614,572 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,658 Sq Ft

  30 Grand St, Highland, NY 12528

  30 Grand St, Highland, NY 12528
• 

  /2

  $29,000

  • Land
  • 0.79 Acre
  • $36,709 per Acre

  0 Hartung Rd Unit H6242040, Highland, NY 12732

  Fantastic level lot. Minutes walk to Sand Beach. Close to lots of great local restaurants, Bethel Woods performing arts center and the Delaware river.

  Dawn Payne Payne Team LLC

  0 Hartung Rd Unit H6242040, Highland, NY 12732
• 

  

  /35

  $680,000 Sold Jun 27, 2025

  14 Tina Dr, Highland, NY 12528

  • 3 Beds
  • 2 Baths
  • 1,656 Sq Ft
  • Built 1974

  Last Sold Summary

  • 1% Above List Price
  • $411/SF
  • 20 Days On Market

  Current Estimated Value $667,728

  Last Listing Agent Monica Schwerberg Compass Greater NY, LLC

  14 Tina Dr, Highland, NY 12528

Showing Results 41 - 80, Page 2 of 18