Highland, NY Homes

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  $599,900

  • 3 Beds
  • 3 Baths
  • 2,329 Sq Ft

  194 Vineyard Ave, Highland, NY 12528

  Welcome to 194 Vineyard Avenue. This beautiful 3-bedroom, 3 Baths home offers the perfect blend of comfort, space, and natural beauty. Custom built by the original owner. Featuring a bright and functional layout, the home is filled with abundant natural light and gleaming hardwood floors. Radiant heat throughout. The eat-in kitchen boasts warm cherry wood cabinets and granite countertops. The

  Angela Briante Briante Realty Group, LLC

  194 Vineyard Ave, Highland, NY 12528
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  /8

  $1,800 per month

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

  635 South St Unit 4, Highland, NY 12528

  Highland area - 2 Bedroom, 1 bathroom apartment in a peaceful, wooded setting. This apartment features a electric stove, hardwood flooring, with heat and hot water included. No pets. Excellent location, close to Route 9W and the Mid-Hudson Bridge.

  James Mitchell Exit Realty Connections

  635 South St Unit 4, 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 $310,844

  Last Listing Agent Daniel Amone BHHS Hudson Valley Properties

  7 Sunny Brook Cir, Highland, NY 12528
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  Not Listed For Sale

  0 Split Rock Dr Unit KEYH6229813, Highland, NY 12719

  0 Split Rock Dr Unit KEYH6229813, Highland, NY 12719

  Last Sold Summary

  • 656 Days On Market

  • Last Sold Price $37,500
  • Jan 15, 2025

  Last Listing Agent Cody Van Houten eXp Realty
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  $515,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,850 Sq Ft

  44 Clearwater Rd, Highland, NY 12528

  Welcome to 44 Clearwater Road, a beautifully maintained and thoughtfully updated home set on 2.8 serene acres in Highland, offering approximately 2,850 sq ft of versatile living space. The upper level features three spacious bedrooms, two full bathrooms, and a stunning, newly renovated kitchen (2023). Step into the light-filled living room with vaulted pine ceilings and a cozy fireplace, where

  Jacob Cohen eXp Realty

  44 Clearwater Rd, Highland, NY 12528
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  /11

  $2,000 per month

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

  67 Black Creek Rd, Highland, NY 12528

  Welcome to The South Hayloft at 67 Black Creek, a truly special rental nestled in a beautifully converted historic horse barn. This quintessential top-floor, two-bedroom apartment blends character and comfort in the most charming way. Flooded with natural light, the space offers a warm and inviting atmosphere, featuring a functional kitchen, comfortable living area, and a thoughtfully designed

  Leigh Wagner-Quintana Keller Williams Hudson Valley

  67 Black Creek Rd, Highland, NY 12528
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  /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 $542,062

  Last Listing Agent Leigh Wagner-Quintana Past Member

  42 Bell Dr, Highland, NY 12528
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  Not Listed For Sale

  245 Upper Rd N, Highland, NY 12528

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1960

  245 Upper Rd N, Highland, NY 12528

  Last Sold Summary

  • $293/SF
  • 27 Days On Market

  • Last Sold Price $410,000
  • Mar 04, 2025

  Last Listing Agent Dan Axtmann BHHS Hudson Valley Properties
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  $649,999

  • 4 Beds
  • 3 Baths
  • 2,241 Sq Ft

  213 Tuckers Corners Rd, Highland, NY 12528

  NEW CONSTRUCTION TO BE BUILT - This stunning new construction ranch-style home offers 2,241 square feet of refined, single-level living space featuring four spacious bedrooms, three full bathrooms, and an attached two-car garage, all set on a sprawling and private 10.20 -acre estate within the Marlboro School District. While the foundation for luxury is set, this property presents a unique

  Richard Baxter Keller Williams Realty

  213 Tuckers Corners Rd, Highland, NY 12528
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  $3,100 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

  Leigh Wagner-Quintana Keller Williams Hudson Valley

  104 North Rd, Highland, NY 12528
• 

  $300,000 Sold Apr 15, 2026

  787 Gregory Ct, Highland, NY 12528

  • 2 Beds
  • 1 Bath
  • 946 Sq Ft
  • Built 2004

  Last Sold Summary

  • 2% Above List Price
  • $317/SF
  • 18 Days On Market

  Current Estimated Value $291,854

  Last Listing Agent Eugene Valoy BHHS Hudson Valley Properties

  787 Gregory Ct, Highland, NY 12528
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  Not Listed For Sale

  73 New Paltz Rd, Highland, NY 12528

  • 2 Beds
  • 1 Bath
  • 740 Sq Ft
  • Built 1970

  73 New Paltz Rd, Highland, NY 12528

  Last Sold Summary

  • $169/SF
  • 3 Days On Market

  • Last Sold Price $125,000
  • Aug 04, 2023

  Last Listing Agent Kristen Zigouras eXp Realty
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  $585,000 Pending

  • 3 Beds
  • 2 Baths
  • 3,486 Sq Ft

  660 N Chodikee Lake Rd, Highland, NY 12528

  Spacious, secluded and close to New Paltz: This roomy ranch features key technical updates while retaining its bright 1970s vibe. Privately set at the end of a long driveway flanked on each side by stacked-bluestone walls, the house sits at the center of the historic Stonewall Farm on its own 19 wooded acres. Entered through a pergola-topped courtyard into a symmetrical blue-stoned foyer gallery,

  Hayes Clement Compass Greater New York, LLC

  660 N Chodikee Lake Rd, Highland, NY 12528
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  /7

  $2,300 per month

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

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

  Beautiful new 2-bedroom, 1 bath open concept apartment, Fully equipped with sleek stainless-steel appliances in the spacious kitchen with beautiful cabinetry. Hardwood floors throughout the modern floor plan. Big and bright windows creating an airy, sun filled living space. First level with private porch. Lot parking. Located close to New Paltz and 5 miles from Poughkeepsie for easy commute to

  Pamela Di Martino Curasi Realty, Inc.

  70 New Paltz Rd Unit 1 B, 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 $444,615

  Last Listing Agent Nancy Senescu Bella NS Properties LLC

  7 Dirks Terrace, Highland, NY 12528
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  Not Listed For Sale

  53 Grand St, Highland, NY 12528

  • 2 Beds
  • 1 Bath
  • 728 Sq Ft
  • Built 1992

  53 Grand St, Highland, NY 12528

  Last Sold Summary

  • $260/SF
  • 29 Days On Market

  • Last Sold Price $189,000
  • Dec 18, 2024

  Last Listing Agent Elizabeth Decker Hudson Dwellings Realty
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  $529,000

  • 3 Beds
  • 3 Baths
  • 2,040 Sq Ft

  4 Cusa Dr, Highland, NY 12528

  Welcome to this beautifully maintained Cape Cod located at 4 Cusa Drive in desirable Highland, offering exceptional curb appeal with an oversized driveway, elegant walkway, inviting entry, and charming covered front porch. Inside, you’ll find updated flooring throughout and a thoughtfully designed layout featuring a spacious living room and dining room with sliders that open to an expansive patio

  Sandra Spector Howard Hanna Rand Realty

  4 Cusa Dr, Highland, NY 12528
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  /23

  $278,000 Sold Jan 28, 2026

  48 Sunny Brook Cir, Highland, NY 12528

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1974

  Last Sold Summary

  • 6% Below List Price
  • $263/SF
  • 32 Days On Market

  Current Estimated Value $274,582

  Last Listing Agent Leigh Wagner-Quintana Past Member

  48 Sunny Brook Cir, Highland, NY 12528
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  Est $484,408 Not Listed For Sale

  876 South St, Highland, NY 12528

  • 3 Beds
  • 1.5 Baths
  • 1,923 Sq Ft
  • Built 1780

  876 South St, Highland, NY 12528

  Last Sold Summary

  • 8% Above List Price
  • $234/SF
  • 76 Days On Market

  • Last Sold Price $450,000
  • Jul 10, 2024

  Last Listing Agent Bethany Wager-Mckee Agnes I Wager Realty Inc.
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  $450,000 Pending

  • 4 Beds
  • 1.5 Baths
  • 3,140 Sq Ft

  668 U S 44, Highland, NY 12528

  With its over 100-year-old history, this home has only changed hands once before, a testament to its enduring appeal and the kind of place that's been lovingly maintained for generations.Set on 1.2 scenic acres, this charming three-story, 4-bedroom, 1.5-bath Colonial offers classic style and beautiful surroundings. A wraparound paved driveway with river stone posts leads to a two-car garage,

  Heather Hughes Hudson Dwellings Realty

  668 U S 44, 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
• 

  Est $277,137 Not Listed For Sale

  117 Half Moon Rd, Highland, NY 12528

  • 4 Beds
  • 1 Bath
  • 1,414 Sq Ft
  • Built 1900

  117 Half Moon Rd, Highland, NY 12528

  Last Sold Summary

  • 57% Above List Price
  • $125/SF
  • 69 Days On Market

  • Last Sold Price $177,000
  • Dec 26, 2023

  Last Listing Agent Nancy Senescu Bella NS Properties LLC
• 

  

  /23

  $449,000

  • 4 Beds
  • 2.5 Baths
  • 2,191 Sq Ft

  26 Lauretta Dr, Highland, NY 12528

  Tucked away on a quiet dead-end road and set high with scenic mountain views, this well-maintained split ranch is ready for its next chapter in the Hudson Valley. Freshly painted and move-in ready, the home features 4 bedrooms and 2.5 bathrooms, along with a wood-burning fireplace and newly finished wood floors that add warmth and character throughout. A beautiful sunroom with three walls of

  Syndi Acampora eXp Realty

  26 Lauretta Dr, Highland, NY 12528
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  $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 $415,810

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

  266 Swartekill Rd, Highland, NY 12528
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  Not Listed For Sale

  16 Washington Ave, Highland, NY 12528

  • 5 Beds
  • 3 Baths
  • 1,866 Sq Ft
  • Built 1900

  16 Washington Ave, Highland, NY 12528

  Last Sold Summary

  • $230/SF
  • 8 Days On Market

  • Last Sold Price $430,000
  • Apr 27, 2023

  Last Listing Agent Dawn Passante Coldwell Banker Village GreenN
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  $469,900 Pending

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

  38 Roxanne Blvd, Highland, NY 12528

  Set at the end of a quiet cul-de-sac on a full acre, this three-bedroom, two-bath split ranch offers space, privacy, and a flexible layout in a convenient New Paltz location. The home is surrounded by mature trees and features a large, level yard with a rear deck—ideal for outdoor enjoyment and entertaining. The main level offers hardwood floors throughout, a bright living area, an eat-in

  Amy Hawks Berardi Realty

  38 Roxanne Blvd, Highland, NY 12528
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  $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

  Current Estimated Value $427,131

  Last Listing Agent Debra Dooley BHHS HUDSON VALLEY PROP-NP

  307 Vineyard Ave, Highland, NY 12528
• 

  Not Listed For Sale

  27 Vineyard Ave, Highland, NY 12528

  • 6 Beds
  • 4 Baths
  • 2,916 Sq Ft
  • Built 1900

  27 Vineyard Ave, Highland, NY 12528

  Last Sold Summary

  • $144/SF
  • 50 Days On Market

  • Last Sold Price $420,000
  • Mar 12, 2025

  Last Listing Agent Hamar Clarke Clarke Realty & Associates LLC
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  $485,000

  • 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
• 

  

  /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 $340,727

  Last Listing Agent Dawn Passante Coldwell Banker Village GreenN

  183 Pancake Hollow Rd, Highland, NY 12528
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  Not Listed For Sale

  50 John White Rd, Highland, NY 12528

  • 9 Beds
  • 5 Baths
  • 1,000 Sq Ft
  • Built 1992

  50 John White Rd, Highland, NY 12528

  Last Sold Summary

  • $865/SF
  • 144 Days On Market

  • Last Sold Price $865,000
  • Jul 09, 2024

  Last Listing Agent Anesha Nesbitt eXp Realty
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  /26

  $524,000

  • 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 retro

  Ronnie Rebis Grist Mill Real Estate

  340 Vineyard Ave, Highland, NY 12528
• 

  $499,000 Sold Feb 03, 2026

  123 Vineyard Ave, Highland, NY 12528

  • 4 Beds
  • 3 Baths
  • 2,400 Sq Ft
  • Built 1900

  Last Sold Summary

  • 17% Below List Price
  • $208/SF
  • 68 Days On Market

  Current Estimated Value $500,173

  Last Listing Agent Dawn Passante Coldwell Banker Village Green

  123 Vineyard Ave, Highland, NY 12528
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  Est $467,271 Not Listed For Sale

  27 Ose Rd, Highland, NY 12528

  • 3 Beds
  • 2 Baths
  • 1,972 Sq Ft
  • Built 1998

  27 Ose Rd, Highland, NY 12528

  Last Sold Summary

  • 10% Above List Price
  • $216/SF
  • 5 Days On Market

  • Last Sold Price $426,000
  • May 09, 2024

  Last Listing Agent Stephanie Way eXp Realty
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  $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
• 

  $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
• 

  Est $253,000 Not Listed For Sale

  847 N Chodikee Lake Rd, Highland, NY 12528

  • Built 1998

  847 N Chodikee Lake Rd, Highland, NY 12528

  Last Sold Summary

  • 198% Above List Price
  • $36/SF
  • 75 Days On Market

  • Last Sold Price $85,000
  • Jul 05, 2023

  Last Listing Agent Dawn Passante Coldwell Banker Village Green
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  $639,000 Pending

  • 4 Beds
  • 1.5 Baths
  • 2,244 Sq Ft

  668 N Chodikee Lake Rd, Highland, NY 12528

  Welcome to Stonewall Farm, a rare 20-acre retreat featuring a charming 19th Century stone house and outbuilding less than two hours from Manhattan and minutes from the New Paltz village center. Privately set at the end of a long driveway flanked on each side by its namesake stacked-bluestone walls, the property features both meadows and woods plus its signature foursquare stone farm house built

  Hayes Clement Compass Greater NY, LLC

  668 N Chodikee Lake Rd, Highland, NY 12528
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  /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 $680,587

  Last Listing Agent Monica Schwerberg Compass Greater NY, LLC

  14 Tina Dr, Highland, NY 12528
• 

  Est $723,751 Not Listed For Sale

  131 Baileys Gap Rd, Highland, NY 12528

  • 4 Beds
  • 3.5 Baths
  • 2,713 Sq Ft
  • Built 2002

  131 Baileys Gap Rd, Highland, NY 12528

  Last Sold Summary

  • 38% Above List Price
  • $194/SF
  • 20 Days On Market

  • Last Sold Price $525,000
  • Aug 08, 2023

  Last Listing Agent William Spinelli BHHS Hudson Valley Properties

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