Ulster, NY Homes

• 

  

  

  /47

  $799,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,709 Sq Ft

  199 Kelder Hwy, Olivebridge, NY 12461

  Nestled in the heart of the Catskills, 199 Kelder HWY is a custom-designed retreat offering unparalleled privacy, and masterful craftsmanship on just under 6.5 acres of pristine land. Built by a highly regarded local builder, this sun-drenched contemporary colonial seamlessly blends modern luxury with natural beauty. The open-concept layout is defined by cathedral ceilings, expansive windows, and

  

  Lynelle Alessi

  Keller Williams Hudson Valley

  (845) 478-7541

  199 Kelder Hwy, Olivebridge, NY 12461
• 

  Explore Olive

• 

  

  

  /22

  $1,800 per month

  • Studio
  • 1 Bath
  • 420 Sq Ft
  • House for Rent

  78 Burgher Rd, West Shokan, NY 12494

  Charming Renovated Barn on Private 4-Acre Lot – Available for Long-Term RentalNestled at the end of a quiet dead-end road on a secluded 4-acre property, this beautifully renovated barn offers a unique opportunity for long-term living in a peaceful, natural setting.The residence features a king-sized bed with a memory foam mattress, an oversized bathroom with Kohler fixtures, and a

  78 Burgher Rd, West Shokan, NY 12494
• 

  $395,000 Sold Aug 01, 2025

  • 2,500 Sq Ft
  • $158/SF
  • 247 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1972

  142 Chris Ln, Olivebridge, NY 12461

  Nestled in a serene cul-de-sac, this inviting 4-bedroom, 2.5-bathroom Ranch home offers the perfect balance of tranquility and convenience. Set on 1.5 flat acres of land, this property is a nature lover’s dream, just minutes from scenic hiking trails, kayaking, boating and the breathtaking Ashokan Reservoir and Woodstock. As you step inside, you’ll be greeted by a cozy sitting room featuring

  Juliet Lopez Keller Williams Rlty Integrity

  142 Chris Ln, Olivebridge, NY 12461
• 

  

  

  /33

  Est $861,949 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,899 Sq Ft

  8 High Point Mountain Rd, West Shokan, NY 12494

  8 High Point Mountain Rd, West Shokan, NY 12494
• 

  

  

  /25

  $349,000

  • 2 Beds
  • 2 Baths
  • 848 Sq Ft

  442 Acorn Hill Rd, Olivebridge, NY 12461

  Charming & Updated 2-Bedroom Home in a Serene Country Setting. Discover this beautifully updated 2-bedroom, 2-bathroom home nestled in a private and peaceful location. With modernized electrical and mechanical systems, this home offers both comfort and reliability. The second-floor bathroom is brand new, adding a touch of luxury to the space. Step outside onto the lovely deck overlooking the

  

  Win Morrison

  Win Morrison Realty

  (845) 377-9502

  442 Acorn Hill Rd, Olivebridge, NY 12461
• 

  

  /45

  $4,500 per month

  • 2 Beds
  • 3 Baths
  • 2,922 Sq Ft
  • House for Rent

  269 Brown Rd, Olivebridge, NY 12461

  Tucked away on over six private acres in Olivebridge, this nearly 3,000-square-foot home offers the kind of space and quiet that's hard to come by. Inside, the layout is open and bright, with oversized windows throughout and plenty of room to spread out—whether you're here for a season or something more long-term. The main level features a spacious living/dining/kitchen area that opens right out

  Briana Cermak BHHS HUDSON VALLEY PROP-WDST

  269 Brown Rd, Olivebridge, NY 12461
• 

  

  /25

  $925,000 Sold Jul 31, 2025

  • Land
  • 11 Acres
  • $87,429 per Acre

  • 38 Days On Market

  0 Lot Pitcairn Estates Rd, Glenford, NY 12433

  Did you just blink? Don't do that again before booking an appointment to see this perfectly private lot with one of the best Ashokan Reservoir views you'll ever experience. The lot is cleared, with a driveway in place, electric nearby, and a BOH-approved perk test. Plus, it's surrounded on all four sides by protected lands—you won't want to miss this one! Located within the exclusive gated

  Sean Zimmerman Halter Associates Realty

  0 Lot Pitcairn Estates Rd, Glenford, NY 12433
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  /6

  Not Listed For Sale

  TBD Aster Rd, Rochester, NY 12461

  TBD Aster Rd, Rochester, NY 12461
• 

  

  /41

  $2,400,000

  • 4 Beds
  • 3 Baths
  • 2,751 Sq Ft

  53 Freeman Avery Rd, Olivebridge, NY 12461

  Modern Marvel in Nature!! Perched atop a private 40-acre wooded sanctuary, this architecturally significant prefabricated modular home—designed by award-winning Resolution: 4 Architecture—offers a rare combination of design-forward living and immersive natural surroundings. Built in 2012 and spanning over 3,671 square feet, this four-bedroom, three-bathroom residence is a true retreat in the

  

  Michael Carr

  eXp Realty

  (845) 684-9454

  53 Freeman Avery Rd, Olivebridge, NY 12461
• 

  

  /31

  $260,000 Sold Jul 30, 2025

  • 604 Sq Ft
  • $430/SF
  • 15 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1935

  70 Watson Hollow Rd, West Shokan, NY 12494

  Charming 3-Season Cottage on the Beaver Kill CreekOffered for the first time in 22 years, this sweet, soulful and well cared for 600 sq. ft. 3-season cottage sits right on the banks of the Beaver Kill Creek in West Shokan. A rare find, this former general store-turned-hideaway invites you to step back in time and enjoy simple pleasures in a truly peaceful setting.Enjoy dining

  Ellen Osgood Coldwell Banker Village Green

  70 Watson Hollow Rd, West Shokan, NY 12494
• 

  

  /35

  Est $1,404,082 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,521 Sq Ft

  452 Krumville Rd, Olivebridge, NY 12461

  452 Krumville Rd, Olivebridge, NY 12461
• 

  

  /22

  $985,000

  • 3 Beds
  • 2 Baths
  • 1,403 Sq Ft

  52 Aster Rd, Olivebridge, NY 12461

  The ultimate upstate escape is waiting for you at 52 Aster Road, Olivebridge, NY. A sanctuary of modern elegance and natural beauty, this exquisite property offers a harmonious blend of luxury and tranquility. Spanning just under 12 acres, this secluded haven backs up onto State Land, providing unparalleled privacy and a mystical ambiance.The residence features three spacious bedrooms

  Ashley Prather Corcoran Country Living

  52 Aster Rd, Olivebridge, NY 12461
• 

  

  /31

  $499,000 Sold Jul 29, 2025

  • 1,104 Sq Ft
  • $452/SF
  • 35 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1976

  15 Desilva Rd, Boiceville, NY 12412

  Welcome to 15 Desilva, a lovely single family abode on a beautifully landscaped parcel. This home boasts an open concept living/dining area, 3 bedrooms, 2 full bathrooms, a sizable family room & office area. Large glass sliders from the dining room lead to the back deck where you can listen to the sounds of the babbling stream. Stainless steel appliances and an island kitchen make entertaining

  Kristabelle McDermott The Machree Group, LLC

  15 Desilva Rd, Boiceville, NY 12412
• 

  

  /26

  Est $527,829 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,440 Sq Ft

  219 Brown Rd, Olivebridge, NY 12461

  219 Brown Rd, Olivebridge, NY 12461
• 

  

  /32

  $649,000

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  1626 County Road 2, Olivebridge, NY 12461

  Welcome to this fully renovated country ranch nestled in the scenic Hudson Valley! This charming 3-bedroom, 2-bathroom home offers 1,400 square feet of thoughtfully designed living space that perfectly balances warm and neutral tones with modern attributes. Enter through the covered rocking chair front porch into a mudroom offering plenty of space with a coat closet, and storage for other outdoor

  Zachary Jarvis Berkshire Hathaway Homeservice

  1626 County Road 2, Olivebridge, NY 12461
• 

  $405,000 Sold Jul 18, 2025

  • 1,908 Sq Ft
  • $212/SF
  • 355 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1880

  451 Acorn Hill Rd, Olivebridge, NY 12461

  Experience the serene charm of upstate NY living in this inviting 2+ bedroom farmhouse boasting picturesque mountain views. THREE additional flex rooms to meet your personal needs. Embrace the allure of elegance with granite countertops, stainless appliances, hardwood floors, enclosed porch, and a spacious deck, perfect for enjoying the abundant sunlight and tranquil surroundings. At the end of

  Heather Martin United RE Hudson Valley Edge

  451 Acorn Hill Rd, Olivebridge, NY 12461
• 

  Est $793,121 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,376 Sq Ft

  534 Upper Samsonville Rd, Olivebridge, NY 12461

  534 Upper Samsonville Rd, Olivebridge, NY 12461
• 

  

  /31

  $645,000 Open Sun 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,924 Sq Ft

  252 Upper Boiceville Rd, Boiceville, NY 12412

  Conveniently located between Woodstock and Phoenicia, This stunning .90 acre, 3bed/2bath renovated 2-story home with both floors having an open floor plan with skylights on the 2nd floor, transom windows, and has beautiful wood accents. The second floor has high ceilings, skylights and loft-like great room that showcase picturesque sunsets and mountain views. The first floor open plan between the

  Richard Greenspan Ruth Gale Realty

  252 Upper Boiceville Rd, Boiceville, NY 12412
• 

  

  /59

  $835,000 Sold Jul 15, 2025

  • 2,640 Sq Ft
  • $316/SF
  • 31 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2006

  77 Jomar Ln, Olivebridge, NY 12461

  Fantastic Contemporary featuring Windows Galore! Exactly what you would want in this Beautiful 10.90 Acre Forested, Rambling Streamside home with Private Patio and Cooling off Oasis! Long Paved drive to this 3 Bedroom, 2.5 Bath home. Gleaming, Hardwood flooring throughout !Huge Gourmet Kitchen with Center Island, Recessed Lighting, Plenty of Cabinet Space, Great Room Features Vaulted Ceilings,

  Mary Orapello Howard Hanna Rand Realty

  77 Jomar Ln, Olivebridge, NY 12461
• 

  

  /34

  Est $925,802 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,200 Sq Ft

  85 Crispell Rd, Olivebridge, NY 12461

  85 Crispell Rd, Olivebridge, NY 12461
• 

  

  /61

  $899,000

  • 3 Beds
  • 2 Baths
  • 1,596 Sq Ft

  258 Watson Hollow Rd, West Shokan, NY 12494

  Spacious 3 bedroom home with breathtaking mountain views. Perched on a hill, this home offers panoramic mountain views and sits on 19.20 acres bordered by a serene stream. There is a front entrance to the home that brings you into the lower level foyer room with blue stone flooring.. On this level is a finished game room/ office space/TV room with plenty of finished space. You also have access to

  Siobhan Scanlan Win Morrison Realty-K

  258 Watson Hollow Rd, West Shokan, NY 12494
• 

  

  /34

  $840,000 Sold Jul 08, 2025

  • 1,512 Sq Ft
  • $556/SF
  • 19 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1973

  516 Watson Hollow Rd, West Shokan, NY 12494

  Welcome to your bright, beautifully updated retreat in the woods — a sun-drenched contemporary ranch (white-washed rough-cut pine siding) that checks all the boxes (and then some). Tucked away across from the rushing year-round Bushkill Creek, this home offers that elusive mix of modern style, peace, and privacy—all within easy reach of Woodstock, Phoenicia, and the Catskills' best trails, ski

  Diana Polack Compass Greater NY, LLC

  516 Watson Hollow Rd, West Shokan, NY 12494
• 

  

  /35

  Est $667,391 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,553 Sq Ft

  393 Acorn Hill Rd, Olivebridge, NY 12461

  393 Acorn Hill Rd, Olivebridge, NY 12461
• 

  

  /53

  $875,000

  • 3 Beds
  • 2 Baths
  • 1,485 Sq Ft

  18 Jomar Ln, Olivebridge, NY 12461

  You'll understand just how special this 41 Acre property is once you arrive. Just driving down the country road to get here is already a treat. Situated at the base of the majestic High Point Mountain you'll find a private driveway that takes you through a beautiful forest and then it opens up to acres of your own open farmlands.....the open fields are perfectly suited to horses and with an

  Edwin Maldonado Howard Hanna Rand Realty

  18 Jomar Ln, Olivebridge, NY 12461
• 

  

  /27

  $248,000 Sold Jun 24, 2025

  • 1,296 Sq Ft
  • $191/SF
  • 105 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1995

  1206 County Road 2, Olivebridge, NY 12461

  You will enjoy this delightful 3 Bedroom, 2 Bath home with very spacious rooms, most of which have spectacular views of the awesome mountains. If you are looking for privacy this is the house for you. Set well back off of County Route 2 with a circular drive, very accommodating back yard and a newer fairly large shed in very good condition. Plenty of room for entertaining, gardening, or whatever

  Sandy Potter Win Morrison Realty

  1206 County Road 2, Olivebridge, NY 12461
• 

  

  /22

  Est $378,095 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,088 Sq Ft

  625 Acorn Hill Rd, Olivebridge, NY 12461

  625 Acorn Hill Rd, Olivebridge, NY 12461
• 

  

  /30

  $1,175,000

  • 3 Beds
  • 2.5 Baths
  • 3,033 Sq Ft

  48 Hillside Dr, West Shokan, NY 12494

  Secluded Luxury Log Home with Spectacular Ashokan Reservoir Views + Additional ParcelWelcome to your dream retreat in the heart of the Catskills. Nestled on a private, serene hillside overlooking the stunning Ashokan Reservoir, this impeccably built 2006 log home combines rustic charm with modern luxury and energy efficiency.Crafted with top-of-the-line mechanicals and highly

  Mark Kanter BHHS HUDSON VALLEY PROP-WDST

  48 Hillside Dr, West Shokan, NY 12494
• 

  

  /53

  $509,250 Sold Jun 13, 2025

  • 1,624 Sq Ft
  • $314/SF
  • 181 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1996

  54 Hillside Dr, West Shokan, NY 12494

  Looking for that special location where every day feels like a vacation? This incredible hillside home is nestled between the mountains on a dead-end road with beauty out every window. The wraparound deck will be one of your favorite spots to enjoy the mountain views while relaxing or entertaining guests. The property provides serenity and a wonderful sense of privacy with plenty of trees, yet

  Edwin Maldonado Howard Hanna Rand Realty

  54 Hillside Dr, West Shokan, NY 12494
• 

  Est $551,065 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,974 Sq Ft

  673 Acorn Hill Rd, Olivebridge, NY 12461

  673 Acorn Hill Rd, Olivebridge, NY 12461
• 

  

  /38

  $599,900

  • 6 Beds
  • 3 Baths
  • 3,059 Sq Ft

  1441 County Road 2, Olivebridge, NY 12461

  Welcome to 1441 County Road 2 in Olivebridge, NY—a beautifully renovated 6-bedroom, 3-bathroom home nestled on 2.32 acres in the heart of the Catskills. This spacious 3,059 sq ft retreat features a brand-new kitchen, three cozy fireplaces, a sun-drenched great room, and a primary en suite on the main floor. With three bedrooms on each level, a full walk-out basement, and a large deck over the

  Nicholas Cuomo Keller Williams Realty

  1441 County Road 2, Olivebridge, NY 12461
• 

  

  /19

  $140,000 Sold Jun 07, 2025

  • Land
  • 2.67 Acres
  • $52,434 per Acre

  • 102 Days On Market

  TBD Wynkoop Rd, Olivebridge, NY 12461

  BUILDING LOT - 2.6 acres in a sought after nook in the Town of Olive. Easy location and shovel ready, recent survey and BOH approval. Wynkoop Rd is wooded and peaceful, close to Sahler Mill loop, Tetta's Market, Sundown State Forest and other local attractions. The land has a variety of mature trees and is dotted with bluestone features. Partially cleared for a driveway with an ideal homesite on

  Ryan Basten Berkshire Hathaway Homeservice

  TBD Wynkoop Rd, Olivebridge, NY 12461
• 

  /2

  Est $537,476 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,358 Sq Ft

  1321 County Road 2, Olivebridge, NY 12461

  1321 County Road 2, Olivebridge, NY 12461
• 

  

  /62

  $750,000 Pending

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

  1489 County Road 2, Olivebridge, NY 12461

  Step back in time and discover the timeless beauty of this lovingly maintained antique farmhouse, nestled on over a stunning landscape of over 8acres of meadows and woodlands. This rare property blends historic character with pastoral charm, offering the perfect setting for a private country retreat, charming hobby farm, or weekend getaway. The home features plank floors and period details, all

  Amy Levine BHHS HUDSON VALLEY PROP-NP

  1489 County Road 2, Olivebridge, NY 12461
• 

  

  /31

  $738,148 Sold May 21, 2025

  • 1,512 Sq Ft
  • $488/SF
  • 36 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2016

  184 Haver Rd, Olivebridge, NY 12461

  Nestled in the heart of the Catskills, 184 Haver Rd is a custom-designed retreat offering unparalleled privacy, stunning mountain views, and masterful craftsmanship on nearly 8 acres of pristine land. Built by a highly regarded local builder, this sun-splashed contemporary home seamlessly blends modern luxury with natural beauty.The open-concept layout is defined by soaring cathedral

  Julie Mazur BHHS HUDSON VALLEY PROP-NP

  184 Haver Rd, Olivebridge, NY 12461
• 

  

  /25

  Est $310,175 Not Listed For Sale

  • 1 Bed

  592 Acorn Hill Rd, Olivebridge, NY 12461

  592 Acorn Hill Rd, Olivebridge, NY 12461
• 

  

  /31

  $649,500 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft

  110 Brown Station Rd, Olivebridge, NY 12461

  Escape to this beautifully updated 3-bedroom, 2-bath Cape home located in the heart of Olive Bridge. Set on a generous lot, the residence blends modern comfort with rustic charm. Inside, you'll find beamed ceilings and elegant hardwood floors throughout, enhancing the spacious layout that's perfect for both relaxation and entertaining. The first floor features a large living/dining area, a full

  Megan Rios Berardi Realty

  110 Brown Station Rd, Olivebridge, NY 12461
• 

  

  /30

  $295,000 Sold May 16, 2025

  • 1,188 Sq Ft
  • $248/SF
  • 194 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1989

  3852 New York 28, Boiceville, NY 12412

  **Unique 8-Acre Property with Versatile Workspaces** Flexible 8-acre property, previously utilized for parking excavation equipment and hosting a sawmill. This residential-zoned property offers an array of opportunities, making it a rare find in the market. It features a spacious three-bay ''barn'' totaling 3852 square feet, complete with water and heating facilities. Perfect for a wide range of

  Ellen Osgood Coldwell Banker Village Green

  3852 New York 28, Boiceville, NY 12412
• 

  

  /31

  Est $538,979 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,246 Sq Ft

  216 Sheldon Hill Rd, Olivebridge, NY 12461

  216 Sheldon Hill Rd, Olivebridge, NY 12461
• 

  

  /49

  $550,000

  • 3 Beds
  • 2.5 Baths
  • 1,400 Sq Ft

  58 Kelder Hwy, Olivebridge, NY 12461

  Tucked in the heart of the Catskills, this meticulously maintained property is a private retreat where every detail has been thoughtfully designed for comfort, beauty, and enjoyment. Surrounded by lush, mature landscaping, the home's outdoor spaces are truly extraordinary—swim in the sparkling pool, entertain on the expansive patio with wet bar, rinse off in the outdoor shower, or simply relax

  Jeanne Boice Howard Hanna Rand Realty

  58 Kelder Hwy, Olivebridge, NY 12461
• 

  

  /11

  $75,000 Sold May 13, 2025

  • 1,200 Sq Ft
  • $62/SF
  • 206 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1990

  349 High Point Mountain Rd, West Shokan, NY 12494

  A short drive from Route 28 and easy access to the Thruway passing over the Ashokan Reservoir on a beautiful rural road sits this great investment property. This gently sloping 2.6 acres property with mountain views is adjacent to protected NYC land and bordered by a year round stream. The double wide home, plus sheds, are in an unknown condition.Therefore the property is being'Sold As

  Henry Ford Coldwell Banker Village Green

  349 High Point Mountain Rd, West Shokan, NY 12494

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