Ulster, NY Homes

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  $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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  /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
• 

  $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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  /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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  /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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  /12

  $3,125 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
• 

  $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 $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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  /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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  /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
• 

  $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
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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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  /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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  /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
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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 $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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  $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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  /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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  /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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  Est $629,503 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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  /12

  $2,200 per month

  • 2 Beds
  • 1 Bath
  • 1,654 Sq Ft
  • Apartment for Rent

  8 Marie Unit 2, Highland, NY 12528

  Picaresque Country Charmer is set on 2 plus acres of lush greenery. Updated and fresh appeal makes this spacious 2nd floor 2 Bedrooms a great choice. if you're looking to relocate this summer, you don't want to miss this one. offers an eat in kitchen with nook, living room, pantry and updated full bath. Each apartment has its own driveway and plenty of extra parking for guests in the common

  Michelle Ayala BHHS HUDSON VALLEY PROP-L

  8 Marie Unit 2, Highland, NY 12528
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  /21

  $410,000 Sold Jul 21, 2025

  • 1,683 Sq Ft
  • $244/SF
  • 69 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1987

  15 Toc Dr, Highland, NY 12528

  This charming raised ranch offers three spacious bedrooms, one and a half bathrooms, and approximately 1,683 square feet of living space on a generous 0.36-acre lot. Located in a desirable neighborhood, this home provides comfort, convenience, and a fantastic location near Highland's best amenities. The main level features a bright and inviting living room that flows into the dining area and

  John Quinn Quinn Realty Group Inc.

  15 Toc Dr, 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
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  /29

  $344,900 Sold Jul 18, 2025

  • 1,681 Sq Ft
  • $205/SF
  • 56 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1962

  124 Half Moon Rd, Highland, NY 12528

  Discover the potential of this charming brick ranch nestled on a serene 8 acre property offering seasonal mountain views. Conveniently located, this property presents a unique opportunity for those seeking a tranquil retreat with ample room for expansion and renovation.Inside, envision creating your dream home with a thoughtful remodel. The spacious layout includes an oversized laundry

  Paige McClintock Howard Hanna Rand Realty

  124 Half Moon Rd, Highland, NY 12528
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  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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  /23

  $2,750 per month

  • 3 Beds
  • 2.5 Baths
  • 1,500 Sq Ft
  • Apartment for Rent

  140 Pancake Hollow Rd Unit A, Highland, NY 12528

  Available September 1st! Gorgeous 3 bedroom, 2.5 bathroom, 1500 sq ft rental located in Highland. Beautiful home with covered front porch and a back patio where the outdoors can be enjoyed. The first floor of the rental has an open concept living room, modern kitchen, laundry area with hook-ups, and a half bath. The second floor features three bedrooms, two full baths, including a primary suite

  Marisa Bellacicco Century 21 Alliance Rlty Group

  140 Pancake Hollow Rd Unit A, Highland, NY 12528
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  $277,000 Sold Jul 15, 2025

  • 1,272 Sq Ft
  • $218/SF
  • 102 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1985

  23 Toc Dr, Highland, NY 12528

  Chance to own a 3 bedroom 1.5 bath home in the Hamlet of Highland. Includes an enclosed porch and a fenced in yard with 2 storage units. This is a rowhouse style home and there are no HOA fees as it is an attached single family. Close to the train station in Poughkeepsie, the walkway over the Hudson and many biking and hiking trails.

  Randy Spiesman Weichert REALTORS

  23 Toc Dr, 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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  /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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  /9

  $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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  /23

  $295,000 Sold Jul 09, 2025

  • 1,220 Sq Ft
  • $242/SF
  • 110 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1974

  4 Sunnybrook Cir, Highland, NY 12528

  Welcome home to this well-maintained townhouse in Highland's Sunnybrook community. Whether buying your first home or looking to downsize, this bright 3-bedroom, 1.5 bath residence has much to offer. The open kitchen and dining area features a convenient pantry closet with washer and dryer, and flows through sliding glass doors to your private fenced deck—perfect for summer gatherings or your

  Anita Cunniff Boxwood Realty and Design

  4 Sunnybrook Cir, Highland, NY 12528
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  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 Open Sun 12PM - 2PM

  • 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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  /25

  $6,000 per month

  • 3 Beds
  • 2.5 Baths
  • 2,661 Sq Ft
  • House for Rent

  33 Maple Ave, Highland, NY 12528

  Beautiful, Hidden gem in Highland,NY. Offers complete privacy yet is minutes away from the quaint hamlet of Highland and the Walkway Over the Hudson State Park. Also nearby to New Paltz and Poughkeepsie. The stylish appointed home includes three bedrooms, two deck areas, a gas grill, and an outdoor woodturning fireplace. Comes furnished but may be negotiable.Tenant pays utilities. Lease could be

  Jonathon Romano-Chander BHHS HUDSON VALLEY PROP-NP

  33 Maple Ave, Highland, NY 12528
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  $727,000 Sold Jul 08, 2025

  • 1,600 Sq Ft
  • $454/SF
  • 43 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2025

  9 White Pine Ln, Highland, NY 12719

  A refined oasis awaits you at White Pines, just two hours from NYC in serene Barryville, NY. Tucked away on the banks of Beaver Brook, this newly constructed three bedroom, two bathroom modern cabin is the private, light-drenched retreat you’ve been looking for. An open concept living space features soaring ceilings and an abundance of oversized windows, making the most of the surrounding

  Megan Kinealy-Hill Country House Realty Inc

  9 White Pine Ln, Highland, NY 12719
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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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