Highland, NY Homes

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  /49

  $439,900 Pending

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

  13 Sharon Dr, Highland, NY 12528

  Beautiful Ranch totally renovated ,new roof 2025 , siding is painted 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

  

  Drita Shala

  Howard Hanna Rand Realty

  (845) 444-3664

  13 Sharon Dr, Highland, NY 12528
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  /50

  $4,047 - $6,237 per month

  Vineyard Commons

  2 - 3 Beds

  6142 Merlot Dr, Highland, NY 12528

  Vineyard Commons offers a fresh approach to active adult living, combining comfort, convenience and style. Our spacious two and three bedroom apartments feature vaulted ceilings, abundant closet space and gourmet kitchens with granite countertops and stainless steel appliances, all on a single level for effortless living. Enjoy the freedom to do as much or as little as you like with amenities

  6142 Merlot Dr, Highland, NY 12528
• 

  $450,000 Sold Mar 23, 2026

  25 Mile Hill Rd, Highland, NY 12528

  • 4 Beds
  • 2 Baths
  • 1,516 Sq Ft
  • Built 1995

  Last Sold Summary

  • 6% Above List Price
  • $297/SF
  • 29 Days On Market

  Current Estimated Value $440,005

  Last Listing Agent Dan Axtmann BHHS Hudson Valley Properties

  25 Mile Hill Rd, Highland, NY 12528
• 

  Not Listed For Sale

  32 Timber Lake Dr, Highland, NY 12792

  • 3 Beds
  • 2 Baths
  • 1,768 Sq Ft
  • Built 2007

  32 Timber Lake Dr, Highland, NY 12792

  Last Sold Summary

  • $297/SF
  • 14 Days On Market

  • Last Sold Price $525,000
  • Jun 26, 2024

  Last Listing Agent Erik Freeland Country House Realty Inc
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  /2

  $200,000

  • Land
  • 6.2 Acres
  • $32,258 per Acre

  0 Vineyard Ave Unit 20256184, Highland, NY 12528

  Rare find. 6.2 acres with town water, sewer and gas. 1/2 zoning can have single family, multi family and multiple units.

  

  Danielle Carlson-murphy

  Start Home Smart, Inc.

  (845) 584-7833

  0 Vineyard Ave Unit 20256184, Highland, NY 12528
• 

  

  /5

  $1,650 per month

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

  276 Fosler Rd Unit 2A, Highland, NY 12528

  “Charming, cozy 2-bedroom unit in a 17-unit complex currently being renovated and available for move-in on May 1. On-site laundry. Call today to schedule a viewing.”Wallkill Schools.

  Dawn Gregg Curasi Realty, Inc.

  276 Fosler Rd Unit 2A, Highland, NY 12528
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  /29

  $344,900 Sold Jul 18, 2025

  124 Half Moon Rd, Highland, NY 12528

  • 3 Beds
  • 2 Baths
  • 1,681 Sq Ft
  • Built 1962

  Last Sold Summary

  • $205/SF
  • 56 Days On Market

  Current Estimated Value $375,060

  Last Listing Agent Paige McClintock Howard Hanna Rand Realty

  124 Half Moon Rd, Highland, NY 12528
• 

  Est $549,986 Not Listed For Sale

  274 Fosler Rd, Highland, NY 12528

  • 4 Beds
  • 3 Baths
  • 2,197 Sq Ft
  • Built 2023

  274 Fosler Rd, Highland, NY 12528

  Last Sold Summary

  • 10% Above List Price
  • $228/SF
  • 78 Days On Market

  • Last Sold Price $499,999
  • Sep 07, 2023

  Last Listing Agent Richard Baxter Keller Williams Realty
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  /8

  $195,000

  • Land
  • 22.3 Acres
  • $8,744 per Acre

  0 Crawford Rd Unit KEY821449, Highland, NY 12528

  Beautiful wooded 22.3 acre parcel along quaint Crawford Road just outside of the charming Delaware river hamlet of Barryville. Close to Eldred, Yulan, Barryville, Narrowsburg and the Delaware River.

  

  Rosemarie DeCristofaro

  Callicoon Real Estate LLC

  (845) 681-6170

  0 Crawford Rd Unit KEY821449, Highland, NY 12528
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  /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
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  /64

  $700,000 Sold Apr 03, 2026

  11 Tricia Blvd, Highland, NY 12528

  • 4 Beds
  • 2.5 Baths
  • 3,526 Sq Ft
  • Built 1999

  Last Sold Summary

  • 103,604% Above List Price
  • $199/SF
  • 23 Days On Market

  Current Estimated Value $671,264

  Last Listing Agent Dawn Passante Coldwell Banker Village GreenN

  11 Tricia Blvd, Highland, NY 12528
• 

  Est $626,965 Not Listed For Sale

  321 Perkinsville Rd, Highland, NY 12528

  • 3 Beds
  • 2.5 Baths
  • 2,214 Sq Ft
  • Built 2010

  321 Perkinsville Rd, Highland, NY 12528

  Last Sold Summary

  • 17% Above List Price
  • $242/SF
  • 32 Days On Market

  • Last Sold Price $535,000
  • Sep 20, 2023

  Last Listing Agent Pamela Kandel
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  /32

  $450,000 Pending

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

  668 State Route 44 55, 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,

  

  Stefan Bolz

  Hudson Dwellings Realty

  (845) 272-5945

  668 State Route 44 55, Highland, NY 12528
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  /7

  $1,700 per month

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

  86 Vineyard Ave Unit 2, Highland, NY 12528

  Village Apartment on second level. Bright apartment with enclosed porch off of bedroom. Rent includes heat, hot water, garbage removal, and one off street parking space. Village has many restaurants and shops.

  JoAnn Ellis Summerset Realty

  86 Vineyard Ave Unit 2, Highland, NY 12528
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  /31

  $425,000 Sold Jul 08, 2025

  831 N Chodikee Lake Rd, Highland, NY 12528

  • 3 Beds
  • 2 Baths
  • 2,524 Sq Ft
  • Built 1994

  Last Sold Summary

  • $168/SF
  • 10 Days On Market

  Current Estimated Value $460,555

  Last Listing Agent Dawn Passante Coldwell Banker Village GreenN

  831 N Chodikee Lake Rd, Highland, NY 12528
• 

  Est $586,093 Not Listed For Sale

  94 Glen Rock Cir, Highland, NY 12528

  • 3 Beds
  • 3 Baths
  • 2,100 Sq Ft
  • Built 2012

  94 Glen Rock Cir, Highland, NY 12528

  Last Sold Summary

  • 14% Above List Price
  • $245/SF
  • 21 Days On Market

  • Last Sold Price $515,000
  • Nov 29, 2023

  Last Listing Agent JOHN SCARANO Keller Williams Realty
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  /9

  $39,900

  • Land
  • 2.82 Acres
  • $14,149 per Acre

  Lot 57.1 Yulan-Barryville Rd, Highland, NY 12791

  Looking for a spot to build your dream home, look no further! This nice mostly level property is wooded with some open space. There is 288' of road frontage and the property is approximately 400' deep. Located close to the towns of Barryville and Yulan. Close to the Delaware River. Land is selling quickly, so schedule your appointment today!

  

  Dawn Curreri

  EAGLE VALLEY REALTY

  (845) 593-8478

  Lot 57.1 Yulan-Barryville Rd, Highland, NY 12791
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  /24

  $2,500 per month

  Hudson Place

  2 Beds

  1300 Hudson Place, Highland, NY 12528

  Welcome to Hudson Place, where your dream lifestyle becomes a reality. This community offers more than just a place to live - it provides a true sense of belonging and convenience featuring an onsite gym, community room and BBQ area. One of the crowning jewels of this location is its proximity to the Walkway Over the Hudson. Take leisurely strolls or invigorating jogs while relishing the scenic

  1300 Hudson Place, Highland, NY 12528
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  $185,000 Sold Jan 21, 2026

  16 Trout Brook Ln, Highland, NY 12528

  • 2 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • Built 2017

  Last Sold Summary

  • 24% Below List Price
  • $127/SF
  • 58 Days On Market

  Last Listing Agent Lisa Cozzolino Cronin & Company Real Estate

  16 Trout Brook Ln, Highland, NY 12528
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  /17

  Not Listed For Sale

  119 Tuckers Corners Rd, Highland, NY 12528

  • 2 Beds
  • 1 Bath
  • 1,080 Sq Ft
  • Built 1982

  119 Tuckers Corners Rd, Highland, NY 12528

  Last Sold Summary

  • $119/SF
  • 15 Days On Market

  • Last Sold Price $129,000
  • May 05, 2023

  Last Listing Agent Daniel Winn Halter Associates Realty
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  /18

  $59,900

  • Land
  • 6.09 Acres
  • $9,836 per Acre

  Lot 28 Summit Dr, Highland, NY 12792

  Beautiful 6+/- acres in gated community! This peaceful property is a nice corner parcel with a lot of road frontage that is mostly level and wooded. This is a great place to build your dream home with lake rights to Timber Lake Estates. Close to Eldred, Barryville and the Delaware River. Come take a look at this property before it's gone!

  

  Dawn Curreri

  Eagle Valley Realty

  (845) 412-9934

  Lot 28 Summit Dr, Highland, NY 12792
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  /15

  $2,595 per month

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

  453 Vineyard Ave Unit 2, Highland, NY 12528

  Three bedroom one bathroom free standing house for rent in desirable Highland NY. Building is new construction featuring energy efficient appliances, windows and materials. Kitchen features quartz countertops, built in hood microwave and dishwasher. Two bedrooms with walk in closet, tiled bathroom surround with shower tub combo. Central heat (propane) and air conditioning. Easy to maintain luxury

  John Quinn 360 Property Management

  453 Vineyard Ave Unit 2, Highland, NY 12528
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  $327,000 Sold Nov 20, 2025

  283 Hawleys Corners Rd, Highland, NY 12528

  • 3 Beds
  • 1 Bath
  • 1,816 Sq Ft
  • Built 1900

  Last Sold Summary

  • 9% Below List Price
  • $180/SF
  • 74 Days On Market

  Current Estimated Value $348,939

  Last Listing Agent Dawn Passante Coldwell Banker Village Green

  283 Hawleys Corners Rd, Highland, NY 12528
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  /2

  $185,000

  • Land
  • 10,454 Sq Ft
  • $770,833 per Acre

  224 Vineyard Ave, Highland, NY 12528

  Recent home demolished and removed. .24 acre lot with town water and sewer (Natural gas on the street but not to the lot). 1.5 miles to the Hamlet of Highland. Ask us about our custom home affordability program.

  

  Danielle Carlson-murphy

  Start Home Smart, Inc.

  (845) 713-8132

  224 Vineyard Ave, Highland, NY 12528
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  /15

  $1,300 - $2,250 per month

  Orchard Hills

  Studio - 2 Beds

  Orchard Hill Cir, Highland, NY 12528

  Explore 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 refuge for strolls, jogs,

  Orchard Hill Cir, Highland, NY 12528
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  $50,000 Sold Nov 17, 2025

  0 Yulan-Barryville Rd Unit KEY857000, Highland, NY 12719

  • Land
  • 7.33 Acres
  • $6,821 per Acre

  Last Sold Summary

  • 29% Below List Price
  • 154 Days On Market

  Last Listing Agent Loretta Wolff NexLvl Real Estate Inc.

  0 Yulan-Barryville Rd Unit KEY857000, Highland, NY 12719
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  Est $464,378 Not Listed For Sale

  625 Milton Turnpike, Highland, NY 12528

  • 2 Beds
  • 1.5 Baths
  • 1,672 Sq Ft
  • Built 1920

  625 Milton Turnpike, Highland, NY 12528

  Last Sold Summary

  • 30% Above List Price
  • $214/SF
  • 39 Days On Market

  • Last Sold Price $358,000
  • May 04, 2023

  Last Listing Agent Lori Rheingold
• 

  

  /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
• 

  

  /10

  $1,950 per month

  • 2 Beds
  • 1 Bath
  • 1,600 Sq Ft
  • Apartment for Rent

  228 Hawleys Corners Rd Unit 2, Highland, NY 12528

  Virtually Staged Pictures of similar Downstairs Apartment The location is unbeatable. Minutes from New Paltz, NYS Thruway, Bus, and Rail System to NYC and Mid Hudson Bridge!Serene Country Setting for this immaculate and tastefully designed. The apartment is less than 10 years old and offers a quiet, private environment. Well-insulated and exceptionally maintained. The apt is located on the

  Nancy Senescu Bella NS Properties LLC

  228 Hawleys Corners Rd Unit 2, Highland, NY 12528
• 

  $559,000 Sold Dec 09, 2025

  19 Emerson Terrace, Highland, NY 12528

  • 3 Beds
  • 3 Baths
  • 2,668 Sq Ft
  • Built 2021

  Last Sold Summary

  • $210/SF
  • 87 Days On Market

  Current Estimated Value $563,677

  Last Listing Agent Susan Todd BHHS Hudson Valley Properties

  19 Emerson Terrace, Highland, NY 12528
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  /35

  Est $593,632 Not Listed For Sale

  135 Chapel Hill Rd, Highland, NY 12528

  • 3 Beds
  • 2.5 Baths
  • 2,650 Sq Ft
  • Built 2018

  135 Chapel Hill Rd, Highland, NY 12528

  Last Sold Summary

  • 9% Above List Price
  • $206/SF
  • 31 Days On Market

  • Last Sold Price $545,000
  • Mar 28, 2024

  Last Listing Agent Lindsay Stevens eXp Realty
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  /65

  $1,250,000

  • 3 Beds
  • 3.5 Baths
  • 4,572 Sq Ft

  74 Bellevue Rd, Highland, NY 12528

  Hudson River Views! This inviting home combines comfort, character, and convenience with a dramatic two-story foyer and open floor plan. Enjoy a cozy living room with a gas fireplace, formal dining area overlooking the river, and a kitchen with custom cherry cabinets, granite counters, and Jenn Air cooktop. A flexible room with French doors makes a great office or fourth bedroom. Bathroom and

  Hollis Dukler Coldwell Banker Village GreenN

  74 Bellevue Rd, 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
• 

  $620,000 Sold Jan 05, 2026

  93 Glen Rock Cir, Highland, NY 12528

  • 4 Beds
  • 2.5 Baths
  • 2,270 Sq Ft
  • Built 2008

  Last Sold Summary

  • 9% Above List Price
  • $273/SF
  • 26 Days On Market

  Current Estimated Value $605,528

  Last Listing Agent Randy Spiesman Weichert REALTORS

  93 Glen Rock Cir, Highland, NY 12528
• 

  Est $139,158 Not Listed For Sale

  10 Sollazzo Ln, Highland, NY 12528

  10 Sollazzo Ln, Highland, NY 12528

  Last Sold Summary

  • 16% Above List Price
  • 234 Days On Market

  • Last Sold Price $120,000
  • Dec 26, 2024

  Last Listing Agent Margareta Schmoll Curasi Realty, Inc.
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  /40

  $549,000 Pending

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  56 Beaver Brook Rd, Highland, NY 12792

  PRIVATE LAKEFRONT LOG CABIN NESTLED ON 6.5+ ACRES IN THE SULLIVAN CATSKILLS in Yulan, NY - Property features over 1000' of water frontage on Toasperns Pond which is a beautiful, non-motorboat 47 acre lake. Enter the property from a privately set driveway tucked in the forest, that leads to this unique and very special home. This cabin has been loved and enjoyed by the same owners for decades.

  Caroline Akt Caroline Akt Realty LLC

  56 Beaver Brook Rd, Highland, NY 12792
• 

  

  /10

  $1,950 per month

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

  228 Hawleys Corners Rd, Highland, NY 12528

  Virtually Staged Pictures of similar downstairs apartment.The location is unbeatable. Minutes from New Paltz, NYS Thruway, Bus, and Rail System to NYC and Mid Hudson Bridge! Serene Country Setting for this immaculate and tastefully designed. The apartment is less than 10 years old and offers a quiet environment with privacy. Well insulated and exceptionally maintained. The apt is located on

  Nancy Senescu Bella NS Properties LLC

  228 Hawleys Corners Rd, Highland, NY 12528
• 

  

  /38

  $380,000 Sold Oct 03, 2025

  399 New Paltz Rd, Highland, NY 12528

  • 4 Beds
  • 3 Baths
  • 2,700 Sq Ft
  • Built 1992

  Last Sold Summary

  • 9% Above List Price
  • $141/SF
  • 18 Days On Market

  Current Estimated Value $409,838

  Last Listing Agent Dawn Passante Coldwell Banker Village GreenN

  399 New Paltz Rd, Highland, NY 12528
• 

  Est $230,500 Not Listed For Sale

  9 Elbow Ln, Highland, NY 12528

  • 4 Beds
  • Built 2024

  9 Elbow Ln, Highland, NY 12528

  Last Sold Summary

  • 10% Above List Price
  • $50/SF
  • 229 Days On Market

  • Last Sold Price $210,000
  • Jan 24, 2024

  Last Listing Agent Christopher Acuti RE/MAX

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