Highland, NY Homes

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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

  0 Crawford Rd Unit KEY821449, Highland, NY 12528
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  /23

  $2,300 Per Month

  • 3 Beds
  • 1 Bath
  • 1,388 Sq Ft
  • Apartment for Rent

  10 Washington Ave Unit 3, Highland, NY 12528

  3-bedroom, newly renovated home in a convenient location. Featuring modern updates throughout and move-in ready for its next tenants. Close to shopping, restaurants, schools, and major commuter routes.

  

  Ammar Iqbal

  eXp Realty

  10 Washington Ave Unit 3, Highland, NY 12528
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  /39

  $415,000

  Sold Jun 03, 2026

  3 Commercial Ave, Highland, NY 12528

  • 3 Beds
  • 1.5 Baths
  • 1,176 Sq Ft
  • Built 1920

  Last Sold Summary

  • 4% Above List Price
  • $353/SF
  • 32 Days On Market

  Current Estimated Value $408,154

  Last Listing Agent Savannah Miceli Century 21 Alliance-NP

  3 Commercial Ave, Highland, NY 12528
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  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

  • 14 Days On Market
• 

  

  

  /3

  $150,000

  • Land
  • 6.7 Acres
  • $22,388 per Acre

  0 Highland Lake Rd Unit KEY868497, Highland, NY 12732

  Located just outside of the charming hamlet of Eldred, this wooded parcel provides access to the spectacular Halfway Brook with rushing waters and waterfall along the rear property line. This area of the Hudson Valley provides easy access to the Delaware River for fishing, rafting & canoeing. It also provides plenty of opportunities for outdoor recreation, camping and hunting. It's a hop, skip

  Theresa Powers

  Keller Williams Realty

  0 Highland Lake Rd Unit KEY868497, Highland, NY 12732
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  /9

  Starting at $2,300 Per Month

  • 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.

  Trailview Place

  42 Toc 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 $450,609

  Last Listing Agent Dan Axtmann BHHS Hudson Valley Properties

  25 Mile Hill Rd, Highland, NY 12528
• 

  Est $589,451

  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

  • 78 Days On Market
• 

  

  /43

  $799,900

  $50K PRICE DROP

  • 6 Beds
  • 3.5 Baths
  • 2,824 Sq Ft

  142 Hawleys Corners Rd, Highland, NY 12528

  Contemporary Colonial with Legal Accessory Apartment, Owned Solar & Private Country Setting. Actual size is 3800 sqft of Country living at its finest! Welcome home to this beautifully maintained 6-bedroom, 3.5-bath Contemporary Colonial featuring owned solar panels, individual mini-split systems in every bedroom for personalized comfort, and a legal 1-bedroom accessory apartment renovated in

  

  Karen Briscoe-Reed

  KW MidHudson

  142 Hawleys Corners Rd, Highland, NY 12528
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  /24

  Starting at $2,500 Per Month

  • 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

  Hudson Place

  1300 Hudson Place, Highland, NY 12528
• 

  $550,000

  Sold May 19, 2026

  56 Beaver Brook Rd, Highland, NY 12792

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 1935

  Last Sold Summary

  • $573/SF
  • 21 Days On Market

  Current Estimated Value $539,135

  Last Listing Agent Caroline Akt Caroline Akt Realty LLC

  56 Beaver Brook Rd, Highland, NY 12792
• 

  Est $648,213

  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

  • 32 Days On Market
• 

  

  /20

  $649,999

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

  217 Tuckers Corners Rd, Highland, NY 12528

  NEW CONSTRUCTION!!! Estimated to be completed by beginning of August. 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 8.90-acre estate within the Marlboro School District. While the foundation for luxury is set,

  

  Richard Baxter

  Keller Williams Realty

  217 Tuckers Corners Rd, Highland, NY 12528
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  /25

  $1,650 - $2,300

  Total Monthly Price

  • 1 - 2 Beds
  • 1 Bath
  • 500 Sq Ft
  • Condo for Rent

  3 White St, Highland, NY 12528

  Live in the heart of Highland just steps from local shops, restaurants, cafes, parks, and the center of town while still enjoying the comfort of a quiet residential setting.This well maintained property offers a rare combination of convenience, character, and Hudson Valley charm. Located minutes from the Mid Hudson Bridge, Walkway Over the Hudson, New Paltz, the Poughkeepsie waterfront,

  3 White St, 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 $691,546

  Last Listing Agent Dawn Passante Coldwell Banker Village GreenN

  11 Tricia Blvd, Highland, NY 12528
• 

  Est $596,122

  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

  • 21 Days On Market
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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

  Lot 57.1 Yulan-Barryville Rd, Highland, NY 12791
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  /2

  Starting at $1,595 Per Month

  • 1 - 2 Beds

  210 Vineyard Ave, Highland, NY 12528

  Located minutes from the Mid-Hudson Bridge, 4 miles from Vassar Hospital. Quiet brookside location. One mile from the quaint shops in the town of Highland.

  Brookside Apartments

  

  210 Vineyard Ave, 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
• 

  Est $133,106

  Not Listed For Sale

  748 State Route 44 55, Highland, NY 12528

  748 State Route 44 55, Highland, NY 12528

  Last Sold Summary

  • 278 Days On Market
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  /32

  $650,000

  • 3 Beds
  • 2 Baths
  • 1,609 Sq Ft

  321 Orchard Rd, Highland, NY 12528

  Set back on nearly two acres, this architecturally inspired ranch captures the best of mid-century design with a dramatic wall of windows, soaring beamed ceilings, a floor-to-ceiling stone fireplace, and seamless indoor-outdoor living centered around a large in-ground pool. Natural light pours through the expansive windows, giving the main living space an open, airy feel while framing peaceful

  

  Craig Smith

  Compass Greater NY, LLC

  321 Orchard Rd, Highland, NY 12528
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  /35

  Starting at $3,899 Per Month

  • 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

  Vineyard Commons

  

  6142 Merlot Dr, Highland, NY 12528
• 

  $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 $353,012

  Last Listing Agent Dawn Passante Coldwell Banker Village Green

  283 Hawleys Corners Rd, Highland, NY 12528
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  /14

  Est $394,681

  Not Listed For Sale

  8 Marie, Highland, NY 12528

  • 3 Beds
  • 2 Baths
  • 1,720 Sq Ft
  • Built 1900

  8 Marie, Highland, NY 12528

  Last Sold Summary

  • 119 Days On Market
• 

  

  /18

  $59,900

  Pending

  • 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

  Lot 28 Summit Dr, Highland, NY 12792
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  /15

  Starting at $1,550 Per Month

  • 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

  Highland Crossing

  3501 9w Route, Highland, NY 12528
• 

  $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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  /35

  Est $629,507

  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

  • 31 Days On Market
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  /48

  $1,200,000

  $95K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,919 Sq Ft

  15 Oakes Rd, Highland, NY 12528

  Welcome to The Riverhouse, an extraordinary custom Lindal Cedar home offering front-row living on the Hudson River. A wall of glass and voluminous ceilings frame breathtaking, ever-changing water views, filling the dramatic great room and its striking fireplace with a light-filled, airy atmosphere. The stylish chef's kitchen is both sleek and functional, featuring high-end cabinetry, granite

  

  Mark McAlpine

  Compass Greater New York, LLC

  15 Oakes Rd, Highland, NY 12528
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  /15

  Starting at $1,300 Per Month

  • 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 Hills

  Orchard Hill Cir, Highland, NY 12528
• 

  $420,000

  Sold Jun 03, 2026

  616 N Elting Corners Rd, Highland, NY 12528

  • 3 Beds
  • 1 Bath
  • 1,556 Sq Ft
  • Built 1996

  Last Sold Summary

  • 5% Above List Price
  • $270/SF
  • 13 Days On Market

  Current Estimated Value $403,596

  Last Listing Agent Carla DeMarsh DeMarsh Properties Inc.

  616 N Elting Corners Rd, Highland, NY 12528
• 

  Est $138,002

  Not Listed For Sale

  10 Sollazzo Ln, Highland, NY 12528

  10 Sollazzo Ln, Highland, NY 12528

  Last Sold Summary

  • 234 Days On Market
• 

  

  /17

  $649,999

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

  213 Tuckers Corners Rd, Highland, NY 12528

  NEW CONSTRUCTION!!! Estimated to be completed the beginning of August - 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

  

  Richard Baxter

  Keller Williams Realty

  213 Tuckers Corners Rd, Highland, NY 12528
• 

  

  /11

  $1,800 Per Month

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

  1 Brinkerhoff Ave Unit 2, Highland, NY 12528

  Property Id: 2752603 Newly Renovated 1-Bedroom Apartment | Prime Hudson Valley Location Enjoy modern living in this beautifully renovated 1-bedroom apartment, tucked away in a quiet, private setting just outside the Village of Highland. Conveniently located just minutes from New Paltz, Kingston, and Poughkeepsie, you'll have easy access to shopping, dining, entertainment, and major

  1 Brinkerhoff Ave 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 $578,080

  Last Listing Agent Susan Todd BHHS Hudson Valley Properties

  19 Emerson Terrace, Highland, NY 12528
• 

  Est $1,461,346

  Not Listed For Sale

  9 Elbow Ln, Highland, NY 12528

  • 4 Beds
  • Built 2024

  9 Elbow Ln, Highland, NY 12528

  Last Sold Summary

  • 229 Days On Market
• 

  

  /18

  $165,000

  Pending

  • 3 Beds
  • 1 Bath
  • 928 Sq Ft

  41 Grand St, Highland, NY 12528

  Opportunity Knocks Bring Your Vision! This charming circa 1800 Cape style home (928 sq ft) is ready for its next chapter. Sitting on a level lot with mature trees and a classic covered front porch, this property offers solid bones and endless potential for the right buyer. Whether you're an investor looking for your next project, a first-time buyer ready to build equity, or a handy homeowner with

  

  Danielle Carlson-Murphy

  Start Home Smart, Inc.

  41 Grand St, Highland, NY 12528
• 

  

  /18

  $2,500

  Total Monthly Price

  • 3 Beds
  • 1 Bath
  • 970 Sq Ft
  • House for Rent

  518 South St, Highland, NY 12528

  3 bed/1 bath 970 sq ft house for rent in Highland with Marlboro schools - $2,500 per month, available nowQuiet neighborhood, close to Mid-Hudson Bridge, centrally located to Newburgh, Poughkeepsie, and New Paltz. Newly renovated, new floors, appliances, full basement with washer and dryer, 1/2 acre corner lot with driveway. Utilities not included, no smoking, no pets. Desirable Marlboro

  518 South St, 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 $633,803

  Last Listing Agent Randy Spiesman Weichert REALTORS

  93 Glen Rock Cir, Highland, NY 12528
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  /41

  Not Listed For Sale

  217 Hawley's Corners Rd, Highland, NY 12528

  • 3 Beds
  • 2 Baths
  • 1,547 Sq Ft
  • Built 1900

  217 Hawley's Corners Rd, Highland, NY 12528

  Last Sold Summary

  • 42 Days On Market

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