Ulster, NY Homes

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  /7

  $195,000

  • Land
  • 22 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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  /36

  $1,350 - $1,875 per month

  Discover Peaceful Living at Black Creek Ap...

  Studio - 2 Beds

  30 Black Creek Rd, Highland, NY 12528

  Experience a new chapter in refined living at 30 Black Creek Apartments, nestled in the peaceful beauty of Esopus, New York. Now under new ownership and professional management, this reimagined community is committed to delivering exceptional service and an elevated living experience.Set against the backdrop of the Hudson Valley’s natural charm, 30 Black Creek offers charming and peaceful

  30 Black Creek Rd, Highland, NY 12528
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  /32

  $1,716,000 Sold Aug 06, 2025

  • 15,000 Sq Ft
  • $114/SF
  • 26 Days On Market

  • 24 Beds
  • 23 Baths
  • Built 1972

  420 Crescent Ave, Highland, NY 12528

  Opportunity to acquire a large, well-located multi-family compound with tremendous upside potential. Originally built as a summer bungalow resort, the property features 32 acres of beautiful grounds with 9 individual buildings housing 22 residential units. These buildings include a 3BR single-family home (occupied by the current owners), a motel-like building with 6 studio apartments, a row

  Matt Eyler New Paltz Properties

  420 Crescent Ave, Highland, NY 12528
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  /20

  Est $343,468 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,106 Sq Ft

  3 Robinson Ln, Highland, NY 12528

  3 Robinson Ln, Highland, NY 12528
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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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  /12

  $3,025 per month

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • House for Rent

  121 North Rd, Highland, NY 12528

  Nestled in the heart of Highland, NY, this recently updated three bedroom, one bath home combines timeless character with modern functionality. The sunlit living room offers generous space for both relaxation and entertaining, while the fully renovated kitchen features sleek stainless steel appliances, ample cabinetry, and expansive counter space perfect for everyday cooking or hosting. Step

  Matthew Cave Hudson Property Services, LLC

  121 North Rd, Highland, NY 12528
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  /30

  $340,000 Sold Aug 06, 2025

  • 1,368 Sq Ft
  • $249/SF
  • 321 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1995

  26 Toc Dr, Highland, NY 12528

  This comfortable 4-bedroom cape is situated in a desirable location near the hamlet of Highland, Enjoy the popular Berean Park, offering swimming, tennis courts, pickle ball courts, playground and picnic areas. Just a few blocks to the Hamlet of Highland with small shops, a yoga studio, pizzerias, delis, and restaurants. Just across the Mid-Hudson Bridge is Metro North for easy city commuting

  Dawn Passante Coldwell Banker Village GreenN

  26 Toc Dr, Highland, NY 12528
• 

  Est $582,540 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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  /29

  $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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  /35

  $1,500 - $1,795 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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  /26

  $315,000 Sold Aug 04, 2025

  • 1,160 Sq Ft
  • $272/SF
  • 25 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1974

  7 Sunnybrook Cir, Highland, NY 12528

  An amazing 3 bedroom, 1 1/2 bath Townhome in the heart of Highland awaits you. One of the best locations as you enter the complex. This complex is surrounded by nature which gives a warm & private setting. Offering a large living room, 1/2 bath and a large kitchen/ Dining area with the pantry & laundry tucked away off the kitchen. The 2nd floor offers 3 bedrooms and a full bath with great light

  Michele Rios BHHS Hudson Valley Properties

  7 Sunnybrook Cir, 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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  /21

  $290,000

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft

  19 North Rd, Highland, NY 12528

  Fully available, and completely renovated, this home is perfect! Starting with the front porch, where you can sit and relax, work, nap, chat, etc. and enjoy the peaceful surroundings. Enter the home on the ground floor. From the minute you walk in, you'll notice how light and bright things are. On this level the laundry room as well as a few additional finished spaces that can be used for a

  

  Nicole Gold

  RE/MAX Benchmark Realty Group

  (845) 683-5805

  19 North Rd, Highland, NY 12528
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  /31

  $2,350 per month

  • 2 Beds
  • 2.5 Baths
  • 1,300 Sq Ft
  • Apartment for Rent

  794 South St, Highland, NY 12528

  Welcome to 794 South Street Unit #2 — a modern townhouse-style apartment built in 2017 and thoughtfully refreshed for today’s renter. This spacious 2-bedroom, 2.5-bath home spans two floors and offers the perfect blend of comfort, convenience, and privacy. Enjoy ground-level entry, a generous parking area, and your own private back patio that opens to a peaceful yard surrounded by light woods —

  Felix Pena RE/MAX Benchmark Realty Group

  794 South St, Highland, NY 12528
• 

  $315,000 Sold Aug 04, 2025

  • 1,160 Sq Ft
  • $272/SF
  • 14 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1974

  7 Sunny Brook Cir, Highland, NY 12528

  An amazing 3 bedroom, 1 1/2 bath Townhome in the heart of Highland awaits you. One of the best locations as you enter the complex. This complex is surrounded by nature which gives a warm & private setting. Offering a large living room, 1/2 bath and a large kitchen/ Dining area with the pantry & laundry tucked away off the kitchen. The 2nd floor offers 3 bedrooms and a full bath with great light

  Daniel Amone BHHS Hudson Valley Properties

  7 Sunny Brook Cir, Highland, NY 12528
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  Est $539,621 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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  /16

  $179,000

  • Land
  • 5 Acres
  • $35,446 per Acre

  Lot 1 Zane Grey Way, Highland, NY 12719

  Fantastic opportunity to own a prime, buildable lake access property in Sullivan County’s beautiful York Lake in the exclusive, private community of York Lake Shores. York Lake is a 103-acre pristine, natural, non-motor boat, spring-fed lake that is only accessible to residents within the two communities that surround it. While not lakefront, this 5.05 acre lot is the closest one can be

  

  Edward Rabon

  Century 21 Geba Realty

  (845) 622-8776

  Lot 1 Zane Grey Way, Highland, NY 12719
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  /35

  $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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  /45

  $700,000 Sold Aug 04, 2025

  • 2,230 Sq Ft
  • $314/SF
  • 46 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1997

  354 Plutarch Rd, Highland, NY 12528

  Your Hudson Valley Oasis Awaits!Come check out this beautiful three-bedroom, two-bath home nestled on 11 picturesque acres just outside of New Paltz!Experience the best of the Hudson Valley with this exceptional rental opportunity:Spacious Living: Enjoy a comfortable and well-appointed three-bedroom home, perfect for those seeking extra space.Two Full Bathrooms: Convenience and

  Nicola Friedman Windsor Realty Services, Inc.

  354 Plutarch Rd, Highland, NY 12528
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  Est $635,123 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,000 Sq Ft

  5 Clearwater Rd, Highland, NY 12528

  5 Clearwater Rd, Highland, NY 12528
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  /15

  $225,000

  • 1 Bed
  • 1 Bath
  • 762 Sq Ft

  534 New Paltz Rd, Highland, NY 12528

  Move-in Ready Gem-Perfect for Easy Living in Highland, NYStep into this completely renovated 1-Bedroom, 1-Bath home designed for comfort and convenience. The entire house has been fully renovated featuring New Septic System, New Roof, New Electrical, New Plumbing, New Washer/Dryer hook up, New water heater, New Electrical panel 200 amp, New Sheetrock, New wall and ceiling insulation, New

  Sandra Rosario Hello Dolly Real Estate

  534 New Paltz Rd, Highland, NY 12528
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  /18

  $1,425 per month

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

  28 Vineyard Ave Unit 28A, Highland, NY 12528

  NEWLY UPDATED 1 BED, 1 BATH FIRST FLOOR RANCH STYLE END UNIT RENTAL FEATURING A COZY AND OPEN CONCEPT FLOOR PLAN. ENJOY EASY TO MAINTAIN LUXURY VINYL FLOORING THROUGHOUT AND A FRESHLY PAINTED INTERIOR IN NEUTRAL PALETTE MAKE FOR EASY SELECTION OF YOUR STYLE OF DÉCOR. REFRESHED KITHEN OFFERS AMPLE CABINETRY WHILE THE FULL BATH IS HIGHLIGHTED BY ITS NEW VANITY AND FIXTURES. WELL PROPORTIONED

  Roadman Etienne BHHS Hudson Valley Properties

  28 Vineyard Ave Unit 28A, Highland, NY 12528
• 

  $689,901 Sold Jul 28, 2025

  • 2,661 Sq Ft
  • $259/SF
  • 30 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2005

  6 Wellington Place, Highland, NY 12528

  Gorgeous, newly updated center hall colonial, adorned with a picturesque, winding stone walkway, and lush landscaping, leading to front porch with trex decking. As you open the front door, you're greeted by an open concept floor plan. This home is situated on almost 2 acres of privacy, on a cul de sac, surrounded by lush forest, and a backyard to die for! Inground "L" shaped pool with new cabana,

  Danielle Oliva RE/MAX Classic Realty

  6 Wellington Place, Highland, NY 12528
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  Est $612,693 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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  /37

  $495,000

  • 5 Beds
  • 4 Baths
  • 2,366 Sq Ft

  258 Martin Ave, Highland, NY 12528

  Major space meets major opportunity: This versatile 2-family home nestled on 2 sunny acres offers privacy plus big potential for comfortable living and extra income. Perfectly adaptable, you can rent both units, live in one while renting the other, or knock down a wall to create a spacious single-family residence. The first unit is an extra roomy, one-level home featuring three bedrooms and two

  Hayes Clement Compass Greater New York, LLC

  258 Martin Ave, Highland, NY 12528
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  /8

  $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
• 

  $335,000 Sold Jul 28, 2025

  • 1,360 Sq Ft
  • $246/SF
  • 82 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1974

  94 Sunny Brook Cir, Highland, NY 12528

  Lovely 3 bedroom townhouse nestled on a private walkway at the end of Sunny Brook Circle. The inviting front door opens into a nicely sized livingroom that looks out on trees and flowering bushes. At the back of the home are the large dining area and kitchen which is equipped with new stainless appliances including a French door refrigerator, gas range, microwave, and dishwasher. A laundry

  ROSLYN RALSTON HomeSmart Homes & Estates

  94 Sunny Brook Cir, Highland, NY 12528
• 

  Est $552,147 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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  /29

  $399,000

  • 3 Beds
  • 1.5 Baths
  • 1,670 Sq Ft

  46 Brescia Blvd, Highland, NY 12528

  Discover your upstate oasis at 46 Brescia Blvd — a beautifully renovated 3-bedroom, 1.5-bath home offering the perfect mix of comfort, style, and indoor-outdoor living in the heart of the Hudson Valley.Located just 90 minutes from NYC and minutes from the Hudson Valley Rail Trail, wineries, and local farm markets, this move-in-ready home features modern upgrades, smart home touches, and

  Heather Bragg ReAttached

  46 Brescia Blvd, Highland, NY 12528
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  /12

  $1,995 per month

  • 2 Beds
  • 1.5 Baths
  • 650 Sq Ft
  • Apartment for Rent

  70 New Paltz Rd, Highland, NY 12528

  Welcome home to this townhouse style 2 bedroom 1 1/2 bath luxury apartment. Be the first to rent this beautiful space complete with hardwood floors, state of the art appliances, granite, huge windows letting in all the natural light you would enjoy. There is a washer/dryer connection in each unit. Plenty of lawn space for use and located within 5 miles to New Paltz and I 87 and the Mid-Hudson

  Pamela Di Martino Curasi Realty, Inc.

  70 New Paltz Rd, Highland, NY 12528
• 

  $526,000 Sold Jul 24, 2025

  • 2,186 Sq Ft
  • $241/SF
  • 19 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 2017

  6 Emerson Terrace, Highland, NY 12528

  This beautiful home blends luxury and practicality throughout. The first floor features a chef-inspired kitchen with stainless steel appliances, abundant cabinetry, and a 6' island with quartz countertops. The adjoining living room boasts a two-story ceiling and a double-sided gas fireplace, creating an inviting, open atmosphere. The spacious first-floor master suite offers a luxury shower with a

  John Olivero Keller Williams Realty

  6 Emerson Terrace, Highland, NY 12528
• 

  

  /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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  /33

  $475,000

  • 3 Beds
  • 2 Baths
  • 2,715 Sq Ft

  334 Pancake Hollow Rd, Highland, NY 12528

  With 3 bedrooms, 2 full bathrooms, and 2,715 square feet of flexible living space, this turnkey home is ready for you to move right in and make it your own.At the heart of the home is a spacious open-concept kitchen and living room — perfect for everyday living and effortless entertaining. The generously sized primary suite offers both privacy and potential, with space to add an

  Leigh Wagner-Quintana Keller Williams Realty HV Nort

  334 Pancake Hollow Rd, Highland, NY 12528
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  /12

  $2,250 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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  /19

  $285,000 Sold Jul 23, 2025

  • 1,470 Sq Ft
  • $194/SF
  • 52 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1950

  460 Vineyard Ave, Highland, NY 12528

  This property in Highland is a charming two-story home that offers a blend of comfort and modern amenities. This spacious residence features a dedicated office space, perfect for remote work or study. The kitchen has been newly renovated, boasting beautiful granite countertops and elegant wood cabinetry, making it both functional and stylish. For those who appreciate organization, a large pantry

  Dawn Passante Coldwell Banker Village GreenN

  460 Vineyard Ave, Highland, NY 12528
• 

  Est $424,464 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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  /27

  $389,000

  • 2 Beds
  • 1 Bath
  • 1,050 Sq Ft

  27 Amato Ln, Highland, NY 12528

  Tucked away on a peaceful dead-end road in Highland, this inviting 2-bedroom, 1-bath home offers the perfect blend of charm, updates, and convenience. Whether you're searching for a starter home or a weekend retreat, this property checks all the boxes. The main level welcomes you with an open layout, rustic exposed beams, and a stylishly renovated kitchen featuring sleek soapstone countertops.

  Jacob Cohen eXp Realty

  27 Amato Ln, Highland, NY 12528
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  /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
• 

  

  /19

  $325,000 Sold Jul 22, 2025

  • 1,296 Sq Ft
  • $251/SF
  • 151 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1958

  183 Pancake Hollow Rd, Highland, NY 12528

  Life is easy in this sweet single level ranch style home. The covered front porch is perfect for relaxing. Inside enjoy the large living room with bay window and fireplace just off the updated kitchen. Entertain friends in the dining room which is open to additional living space. Just off the dining room is a screened in porch for comfortable summer nights. The lower level features full basement

  Dawn Passante Coldwell Banker Village GreenN

  183 Pancake Hollow Rd, Highland, NY 12528
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  /4

  Not Listed For Sale

  TBD New Paltz Rd, Highland, NY 12528

  TBD New Paltz Rd, Highland, NY 12528

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