Highland, NY Homes

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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) 524-9107

  Lot 57.1 Yulan-Barryville Rd, Highland, NY 12791
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  /50

  $2,769 - $6,300 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
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  $347,000 Sold Apr 11, 2025

  122 Vineyard Ave, Highland, NY 12528

  • 4 Beds
  • 2 Baths
  • 2,110 Sq Ft
  • Built 1900

  Last Sold Summary

  • 4% Above List Price
  • $164/SF
  • 28 Days On Market

  Current Estimated Value $357,903

  Last Listing Agent Sandra Cotthaus 1st Independent Realty Grp

  122 Vineyard Ave, Highland, NY 12528
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  Est $545,357 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,478 Sq Ft

  288 Baileys Gap Rd, Highland, NY 12528

  288 Baileys Gap Rd, Highland, NY 12528
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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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  /9

  $1,500 per month

  • 0.5 Baths
  • 750 Sq Ft
  • Apartment for Rent

  199 State Route 299 Unit 103, Highland, NY 12528

  Prime Commercial Space for Rent on Highly Trafficked Route 299Unlock exceptional visibility for your business with this newly updated commercial space located directly on Route 299—one of Highland’s busiest corridors. With a parking lot that wraps around the building, you and your clients can enjoy convenient access from both Route 299 and Riverside Road, just moments from the Highland Rail

  Ashley Olson Minard eXp Realty

  199 State Route 299 Unit 103, 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 $360,160

  Last Listing Agent Paige McClintock Howard Hanna Rand Realty

  124 Half Moon Rd, Highland, NY 12528
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  Not Listed For Sale

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

  32 Timber Lake Dr, Highland, NY 12792

  32 Timber Lake Dr, Highland, NY 12792
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  /22

  $850,000 Pending

  • 5 Beds
  • 4 Baths
  • 3,230 Sq Ft

  7 Elliotts Ln, Highland, NY 12528

  Welcome to 7 Elliotts Ln, where space, comfort, and flexibility all come together—right in the heart of New Paltz. Set on a full acre, this 5-bedroom, 4-bath home offers over 3,200 square feet of living space, including a legal accessory apartment that's ideal for guests, extended living, or additional rental income. Step inside and you'll find beautifully new hardwood floors that run throughout

  

  Donna Brooks

  Compass Greater NY, LLC

  (845) 250-6194

  7 Elliotts Ln, 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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  /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 $486,511

  Last Listing Agent Dawn Passante Coldwell Banker Village GreenN

  831 N Chodikee Lake Rd, Highland, NY 12528
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  Est $566,510 Not Listed For Sale

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

  274 Fosler Rd, Highland, NY 12528

  274 Fosler Rd, Highland, NY 12528
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  /2

  $185,000

  • Land
  • 0.24 Acre
  • $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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  /7

  $1,350 per month

  • 1 Bath
  • 300 Sq Ft
  • Apartment for Rent

  200 Fosler Rd Unit 49, Highland, NY 12528

  Small studio cottage located within the Marlboro school district!Quiet area but with plenty of neighbors. All utilities included tenant pays for wifi otherwise. Full application is needed including background & credit check. These are motel like set ups, it is located on an old catering site.

  Angela Kadian Stonewall Realty Group LLC

  200 Fosler Rd Unit 49, 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

  Last Listing Agent Dawn Passante Coldwell Banker Village Green

  283 Hawleys Corners Rd, Highland, NY 12528
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  Est $611,211 Not Listed For Sale

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

  321 Perkinsville Rd, Highland, NY 12528

  321 Perkinsville Rd, Highland, NY 12528
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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
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  /2

  $1,695 - $1,850 per month

  Brookside Apartments

  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.

  210 Vineyard Ave, 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 $610,682 Not Listed For Sale

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

  94 Glen Rock Cir, Highland, NY 12528

  94 Glen Rock Cir, Highland, NY 12528
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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 and the Delaware River.

  

  Rosemarie DeCristofaro

  Callicoon Real Estate LLC

  (845) 671-5361

  0 Crawford Rd Unit KEY821449, Highland, NY 12528
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  /4

  $1,400 per month

  • 1 Bath
  • 400 Sq Ft
  • Apartment for Rent

  70 New Paltz Rd Unit 2A, Highland, NY 12528

  Very pretty and spacious studio apartment. Located 5 miles to New Paltz and 5 miles to Poughkeepsie and Metro North. Modern and beautifully renovated. Water/Sewer, lawn care, trash removal and snow removal. Call for pet approval. Off street parking in a lot. Many amenities located in this area.

  Pamela Di Martino Curasi Realty, Inc.

  70 New Paltz Rd Unit 2A, Highland, NY 12528
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  $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

  Last Listing Agent Susan Todd BHHS Hudson Valley Properties

  19 Emerson Terrace, Highland, NY 12528
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  /17

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,080 Sq Ft

  119 Tuckers Corners Rd, Highland, NY 12528

  119 Tuckers Corners Rd, Highland, NY 12528
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  /16

  $159,000

  • Land
  • 5.05 Acres
  • $31,485 per Acre

  Lot 1 Zane Grey Way, Highland, NY 12719

  Fantastic opportunity to own a prime, buildable property with access to beautiful York Lake. Located in the exclusive private community of York Lake Shores, York Lake is a pristine 103-acre, natural, non-motor boat, spring-fed lake that is only accessible to residents within the two communities that surround it. This lovely 5.05 acre lot is as close as one can be to the community’s lake access

  

  Edward Rabon

  Compass Greater NY, LLC

  (845) 448-8745

  Lot 1 Zane Grey Way, Highland, NY 12719
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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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  $365,000 Sold Mar 03, 2025

  325 Perkinsville Rd, Highland, NY 12528

  • 3 Beds
  • 2 Baths
  • 1,458 Sq Ft
  • Built 1996

  Last Sold Summary

  • 19% Below List Price
  • $250/SF
  • 88 Days On Market

  Current Estimated Value $388,460

  Last Listing Agent Geraldine Gaudioso Century 21 Alliance Rlty Group

  325 Perkinsville Rd, Highland, NY 12528
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  Est $443,928 Not Listed For Sale

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

  625 Milton Turnpike, Highland, NY 12528

  625 Milton Turnpike, Highland, NY 12528
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  /25

  $365,000

  • 2 Beds
  • 2 Baths
  • 1,300 Sq Ft

  241 Upper Rd N, Highland, NY 12528

  Welcome to 241 Upper North Road - Where Comfort Meets Convenience! This beautifully maintained modern double-wide mobile home offers the charm and functionality of a modular home, nestled on a spacious 0.78-acre lot. With an inviting open floor plan, this residence features 2 bedrooms, a versatile den with a cozy gas fireplace, and 2 full bathrooms, offering ample space for both relaxation and

  

  Isabel Alves

  RE/MAX Town & Country

  (845) 493-3607

  241 Upper Rd N, Highland, NY 12528
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  /16

  $2,000 per month

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

  698 South St Unit 2, Highland, NY 12528

  New floors are on the way, be in by the holidays! The eat in kitchen, living room & half bath start off the 1st floor of this middle unit condo, which also offers two 2nd floor bedrooms, a full bath with/tub & plenty of closet space. The washer and dryer hook ups are located in your full basement. Rental includes trash removal, lawn maintenance & snow removal~ except your porches and steps.

  Michele Spignardo Keller Williams Hudson Valley

  698 South St Unit 2, Highland, NY 12528
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  $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

  Last Listing Agent Randy Spiesman Weichert REALTORS

  93 Glen Rock Cir, Highland, NY 12528
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  /35

  Est $613,578 Not Listed For Sale

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

  135 Chapel Hill Rd, Highland, NY 12528

  135 Chapel Hill Rd, Highland, NY 12528
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  /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
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  /15

  $2,200 - $2,250 per month

  Orchard Hills

  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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  $359,900 Sold Feb 21, 2025

  721 Milton Turnpike, Highland, NY 12528

  • 4 Beds
  • 2 Baths
  • 2,535 Sq Ft
  • Built 1930

  Last Sold Summary

  • $142/SF
  • 8 Days On Market

  Current Estimated Value $377,013

  Last Listing Agent Megan Rios Berardi Realty

  721 Milton Turnpike, Highland, NY 12528
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  Est $126,207 Not Listed For Sale

  10 Sollazzo Ln, Highland, NY 12528

  10 Sollazzo Ln, Highland, NY 12528
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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
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  /12

  $2,600 per month

  • 2 Beds
  • 2.5 Baths
  • 1,200 Sq Ft
  • Apartment for Rent

  42 Maple Ave Unit 2, Highland, NY 12528

  Beautiful country setting, just up the street from the The Ridge by Mill House (previously THe Gunk House Restaurant) in Clintondale, houses this picturesque stately Victorian three family home. The available two bedroom offers a full galley kitchen, formal dining room, spacious living room both with beamed ceiling, half bath and main bedroom and full bath on the main level. The second level

  Laurie Dellavilla Miller Professional Realty Group

  42 Maple Ave Unit 2, Highland, NY 12528
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  /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 $366,564

  Last Listing Agent Dawn Passante Coldwell Banker Village GreenN

  399 New Paltz Rd, Highland, NY 12528
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  Est $222,000 Not Listed For Sale

  9 Elbow Ln, Highland, NY 12528

  9 Elbow Ln, Highland, NY 12528

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