Ulster, NY Homes

• 

  

  

  /51

  $759,000

  • 3 Beds
  • 2 Baths
  • 1,532 Sq Ft

  97 John Joy Rd, Woodstock, NY 12498

  The best of both worlds!A boho cottage paradise and a modern ADU (Accessory Dwelling Unit). Peace and tranquility and 3 miles from the center of the most famous small town in the world. Five-star dining and unique shopping opportunities.The property is situated adjacent to the Thorne Preserve - 60 acres boasting the most painted views of Overlook Mountain. The preserve is a

  Benjamin Armento Coldwell Banker Village Green

  97 John Joy Rd, Woodstock, NY 12498
• 

  Explore Zena

• 

  

  

  /35

  $703,000 Sold Jul 24, 2025

  • 1,436 Sq Ft
  • $490/SF
  • 29 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1972

  23 Maurizi Ln, Woodstock, NY 12498

  Searching for the perfect blend of style, comfort, and convenience? It's here! This remarkable contemporary in one of Woodstock's most sought-after neighborhoods is ready to welcome you home. Set on a spacious and private 1.34-acre lot, this beautifully maintained four-bedroom, 2.5-bath residence offers a seamless mix of modern updates and inviting charm.The heart of the home is the

  Melissa Mayes Serhant LLC

  23 Maurizi Ln, Woodstock, NY 12498
• 

  

  

  /35

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,299 Sq Ft

  162 Van Dale Rd Unit 170, Woodstock, NY 12498

  162 Van Dale Rd Unit 170, Woodstock, NY 12498
• 

  

  

  /43

  $1,244,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,088 Sq Ft

  178 Chestnut Hill Rd, Woodstock, NY 12498

  Discover the epitome of modern luxury in this brand new build, with a sleek aesthetic that seamlessly blends style and comfort. Using ecological and state of the art building practices highlighted by exceptional craftsmanship and distinctive design. Ascend an impressive switchback floating staircase to a stunning wall of windows that flood the open concept, living, kitchen, and dining area

  Richard Vizzini Corcoran Country Living

  178 Chestnut Hill Rd, Woodstock, NY 12498
• 

  

  

  /77

  $2,000,000 Sold Jun 26, 2025

  • 2,801 Sq Ft
  • $714/SF
  • 19 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1874

  657 Zena Rd, Woodstock, NY 12498

  This historically significant 1700's Woodstock Farmstead and beautifully appointed guest house featured in Elle Decor Magazine combines classic American roots with modern country living and a touch of international elegance. Lovingly cared for both inside and out with thoughtfully designed updates and gardens, including an English-made Hartley greenhouse, abundant fruit trees and exquisite

  Amy Lonas Coldwell Banker Village Green

  657 Zena Rd, Woodstock, NY 12498
• 

  

  /32

  Est $2,326,096 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,954 Sq Ft

  34 Vandebogart Rd, Woodstock, NY 12498

  34 Vandebogart Rd, Woodstock, NY 12498
• 

  

  /38

  $795,000

  • 2 Beds
  • 1 Bath
  • 1,250 Sq Ft

  276 Chestnut Hill Rd, Woodstock, NY 12498

  Tucked back on a six acre lot just minutes to the town of Woodstock sits this fairytale two bedroom cottage. The woodland view is yours to explore, the deep forest of evergreens, ferns and moss. Inside, you're tucked into charming spaces or enjoying the expansive Great Room, with a stone fireplace at the center and vaulted ceilings with beautiful exposed beams. A wall of windows frames the view.

  Annabel Taylor Four Seasons Sotheby's Int.

  276 Chestnut Hill Rd, Woodstock, NY 12498
• 

  $440,000 Sold May 16, 2025

  • 2,480 Sq Ft
  • $177/SF
  • 12 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1960

  5 Lazy Brook Ln, Woodstock, NY 12498

  On arriving at 5 Lazy Brook Lane, you’ll love the privacy of this cul-de-sac setting, welcoming you home to nearly 2,500 square feet of beautifully updated living space. Step inside this spacious, one-level home and be greeted by brand-new flooring, fresh white cabinetry, and modern fixtures that bring a bright and contemporary feel. As you move through the home, you'll appreciate its open

  Christian Baez Keller Williams Hudson Valley

  5 Lazy Brook Ln, Woodstock, NY 12498
• 

  

  /22

  Est $598,379 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,106 Sq Ft

  6 Allen Dr, Woodstock, NY 12498

  6 Allen Dr, Woodstock, NY 12498
• 

  

  /56

  $549,000

  • 2 Beds
  • 2 Baths
  • 1,352 Sq Ft

  680 Zena Rd, Woodstock, NY 12498

  Turn key Opportunity - whether you are looking for a full time residence or second home. Often referred to as Zena Cottage by Airbnb guests, this charming home is 3 minutes to the Village of Woodstock, and a short drive to hip uptown Kingston, Rhinebeck and the NYS Thruway. 2 hrs from NYC.Set against a private wooded backdrop, this 1957 home on 1/3 of an acre has a lush lawn, spectacular

  Benjamin Armento Coldwell Banker Village Green

  680 Zena Rd, Woodstock, NY 12498
• 

  

  /47

  $530,000 Sold Apr 25, 2025

  • 1,158 Sq Ft
  • $458/SF
  • 178 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1964

  33 Whitney Dr, Woodstock, NY 12498

  Sought-After Woodstock Mid-Century Raised RanchExperience the unique character and tranquility of this Woodstock gem, where mid-century design meets modern comfort. This move-in ready, 1,820 square foot 1964 mid-century raised ranch is nestled in a peaceful, quiet neighborhood in the highly sought-after Woodstock area. This home features 4 bedrooms and 2 full bathrooms, offering ample space for

  Benjamin Armento Coldwell Banker Village Green

  33 Whitney Dr, Woodstock, NY 12498
• 

  

  /35

  Est $576,564 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,166 Sq Ft

  15 Niles Dr, Woodstock, NY 12498

  15 Niles Dr, Woodstock, NY 12498
• 

  

  /40

  $1,395,000

  • 4 Beds
  • 5 Baths
  • 3,100 Sq Ft

  5 Downer Ln, Woodstock, NY 12498

  Buckle up! 5 Downer Lane may be themost interesting property you see allyear! This 19th century hand-hewnbarn-to-house conversion has 35 footceilings, sunlight and bespoke stainglass throughout. The layout is wideopen to your own creativity and all the possibilities youcan conjure up. Permitted as asuccessful year ‘round Airbnb andcurrently configured with

  Jason Karadus Corcoran Country Living

  5 Downer Ln, Woodstock, NY 12498
• 

  

  /38

  $699,000 Sold Apr 23, 2025

  • 2,548 Sq Ft
  • $274/SF
  • 55 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1970

  31 Carey Dr, Woodstock, NY 12498

  Are you searching for the perfect blend of style, comfort, and convenience? Look no further! This stunning Colonial in one of Woodstock's most sought-after neighborhoods is now on the market, and it's ready to welcome you home. Imagine stepping into this lovingly maintained and beautifully updated four-bedroom, 2.5-bath residence, nestled on a spacious lot (1.44 acres) that offers both room to

  Michael Carr eXp Realty

  31 Carey Dr, Woodstock, NY 12498
• 

  

  /29

  Est $504,610 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,029 Sq Ft

  12 Niles Dr, Woodstock, NY 12498

  12 Niles Dr, Woodstock, NY 12498
• 

  

  /28

  $1,888,000

  • Land
  • 61 Acres
  • $30,981 per Acre

  TBD 60 Acre Zena Rd, Woodstock, NY 12498

  An incredible, rare opportunity in Woodstock.It has been very long time since a parcel of this magnitude has available for sale in Woodstock. This contiguous 60-acre property, consisting of two 30-acre lots, features rolling hills, stunning rock outcroppings, mountain views, and diverse mature trees, uniquely offering both beauty and potential. A privately built road, completed by the

  Baris Demirel Serhant LLC

  TBD 60 Acre Zena Rd, Woodstock, NY 12498
• 

  

  /31

  $978,000 Sold Apr 21, 2025

  • 3,502 Sq Ft
  • $279/SF
  • 12 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1920

  38 Vandebogart Rd, Woodstock, NY 12498

  Enchanting Woodland Retreat with Guest House & Studio: Tucked away on just over two acres of serene, wooded landscape, this one-of-a-kind property offers the perfect blend of privacy, charm, and modern convenience just minutes from the vibrant town of Woodstock. With a beautifully designed main house, a separate two-story guest house, and an inspiring studio space above a heated two-car garage,

  Alexis Li Corcoran Country Living

  38 Vandebogart Rd, Woodstock, NY 12498
• 

  

  /35

  Est $610,304 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,259 Sq Ft

  157 Van Dale Rd, Woodstock, NY 12498

  157 Van Dale Rd, Woodstock, NY 12498
• 

  

  /31

  $1,099,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,252 Sq Ft

  32 Maurizi Ln, Woodstock, NY 12498

  Blending classic country charm with modern sophistication, this newly built modern farmhouse offers over 3,000 square feet of beautifully finished living space. Designed with clean lines, a neutral palette, and layered textures, it delivers a timeless aesthetic full of warmth and character. The home features four spacious bedrooms, three and a half baths, a fully finished lower level, and

  Richard Vizzini Corcoran Country Living

  32 Maurizi Ln, Woodstock, NY 12498
• 

  

  /49

  $585,000 Sold Feb 19, 2025

  • 1,960 Sq Ft
  • $298/SF
  • 61 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1963

  70 Vandebogart Rd, Woodstock, NY 12498

  Your Hudson Valley Dream Home Awaits!Welcome to this beautifully renovated four-bedroom Colonial, located in the heart of the Hudson Valley, just minutes from Woodstock, Kingston, and Saugerties. With a prime location and countless upgrades, this home is a must-see!Step inside and discover a flowing floor plan that seamlessly connects every space, creating a warm and inviting atmosphere.

  Dominique Musialkiewicz Howard Hanna Rand Realty

  70 Vandebogart Rd, Woodstock, NY 12498
• 

  

  /27

  Est $536,662 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,012 Sq Ft

  3 Niles Dr, Woodstock, NY 12498

  3 Niles Dr, Woodstock, NY 12498
• 

  

  /38

  $585,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  3 Oriole Dr, Woodstock, NY 12498

  Set in the quiet surroundings of Woodstock, this thoughtfully renovated ranch-style home offers over 2,000 square feet of comfortable living space. With three bedrooms and hardwood floors throughout the main level, the layout is open and welcoming.At the center of the home is a bright, spacious living room with a brick fireplace—ideal for relaxing evenings. It flows into a dining area and

  Mario Geissler Four Seasons Sotheby's Int'l R

  3 Oriole Dr, Woodstock, NY 12498
• 

  $840,000 Sold Jan 13, 2025

  • 2,352 Sq Ft
  • $357/SF
  • 144 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1979

  7 Maurizi Ln, Woodstock, NY 12498

  A/O - Continue to showMOVE-IN READY!!! Only a few minutes drive from the center of Woodstock, you will find this beautiful, just renovated, modern monochromatic color scheme contemporary home nestled surrounded by trees in almost 2 acres. Offering four spacious bedrooms, two and a half bathrooms tastefully designed with carrera marble tile, oak vanities and brushed gold accents. This

  Eliana Amodio Amodio Real Estate & Prop

  7 Maurizi Ln, Woodstock, NY 12498
• 

  

  /20

  Est $770,897 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,173 Sq Ft

  162 Sherman Rd, Kingston, NY 12401

  162 Sherman Rd, Kingston, NY 12401
• 

  

  /43

  $660,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 1,564 Sq Ft

  36 Oriole Dr, Woodstock, NY 12498

  Nestled in the heart of Woodstock, this beautifully remodeled 4-bedroom, 2.5- bathroom home seamlessly blends modern comfort with timeless charms. With an open-concept layout and soaring vaulted ceilings, the home feels both spacious and inviting. Original hardwood floors run throughout, adding warmth and character. The custom-designed kitchen is a chef's dream, featuring brand new

  Eliana Amodio Amodio Real Estate & Prop

  36 Oriole Dr, Woodstock, NY 12498
• 

  $465,000 Sold Dec 23, 2024

  • 1,666 Sq Ft
  • $279/SF
  • 63 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1964

  78 van de Bogart Rd, Woodstock, NY 12498

  Updated Home on a Streamside corner lot! This 4 bedroom one and a half bath home has a sunny, spacious living room with fireplace and a balcony overlooking the 1-acre landscaped yard, perfect spot to relax and listen to the bustling stream. Large eat in kitchen with plenty of cabinets, three bedrooms and a full bath complete the main level. Lower level has a large den with second fireplace and

  Nicole Polito Berardi Realty

  78 van de Bogart Rd, Woodstock, NY 12498
• 

  /2

  Est $594,543 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,184 Sq Ft

  24 Oriole Dr, Woodstock, NY 12498

  24 Oriole Dr, Woodstock, NY 12498
• 

  

  /25

  $529,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,316 Sq Ft

  146 Sherman Rd, Kingston, NY 12401

  PRICE IMPROVEMENT!!!Woodstock Charmer on Cul-de-Sac with Guest Apartment on 1.68 Acres!Tucked away on a quiet cul-de-sac off Zena Road, 8 minutes from the Village of Woodstock, this unique property offers the perfect blend of location, space, flexibility, and opportunity. Set far back from the road on a serene 1.68-acre lot, bordered on one side by a little stream, this tree filled

  Wendy Erikson BHHS HUDSON VALLEY PROP-WDST

  146 Sherman Rd, Kingston, NY 12401
• 

  

  /41

  $575,000 Sold Dec 20, 2024

  • 1,842 Sq Ft
  • $312/SF
  • 26 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1935

  47 van de Bogart Rd, Woodstock, NY 12498

  Back on market! Now is your chance. Buyer backed out for personal reasons having nothing to do with the house. Set well back from the road and sited on 4+ acres, this wonderful 1935 farmhouse has been updated over the years yet retains its original charm and character. The grounds are lovely with established perennials, level grassy meadow and woods to the rear. The front entry leads you through

  Amy Lonas Coldwell Banker Village Green

  47 van de Bogart Rd, Woodstock, NY 12498
• 

  

  /33

  Est $674,996 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,430 Sq Ft

  4 Oriole Dr, Woodstock, NY 12498

  4 Oriole Dr, Woodstock, NY 12498
• 

  

  /17

  $399,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,181 Sq Ft

  16 Delisio Ln, Woodstock, NY 12498

  Charming Mid-Century Woodstock Artist's Retreat2 Bed | 1 Bath | 1 Acre | North-Facing Studio | FireplaceStep into a timeless mid-century haven nestled in the heart of Woodstock's artistic legacy. This lovingly maintained 2-bedroom, 1-bath home offers a rare blend of privacy, inspiration, and convenience.Ideal for creatives and nature lovers alike, the home features a

  Mark Kanter BHHS HUDSON VALLEY PROP-WDST

  16 Delisio Ln, Woodstock, NY 12498
• 

  

  /32

  $950,000 Sold Nov 12, 2024

  • 2,258 Sq Ft
  • $421/SF
  • 37 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2015

  185 John Joy Rd, Wood Stock, NY 12498

  A gorgeous three bedroom house tucked away from the road in its own cozy clearing in the woods — this property in Woodstock, New York is a must-see. With a 5 acre yard surrounded by beautiful lush green trees, this house has the perfect combination of privacy, comfort, and that special feeling of ''home.''It's just a short drive up the road from Thorn Preserve, which offers 60 acres of

  Sheena Lepez Compass Greater New York, LLC

  185 John Joy Rd, Wood Stock, NY 12498
• 

  

  /30

  Est $701,005 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,499 Sq Ft

  104 Cardinal Ct, Woodstock, NY 12498

  104 Cardinal Ct, Woodstock, NY 12498
• 

  

  /27

  $545,000 Pending

  • 4 Beds
  • 1.5 Baths
  • 1,944 Sq Ft

  41 Whitney Dr, Woodstock, NY 12498

  Peaceful 4 Bedroom Home Just Minutes From Town - Move in Ready!Welcome to this beautifully updated 4 bedroom, 1.5 bath home in a quiet Woodstock Neighborhood, just minutes to the center of town. Enjoy the best of both worlds: serenity and privacy with a spacious back and front yard and easy access to shops, dining and all the charm that Woodstock has to offer. Inside you will find freshly painted

  Kathryn Johnson William Pitt Sothebys Int Rlty

  41 Whitney Dr, Woodstock, NY 12498
• 

  

  /19

  $575,000 Sold Nov 08, 2024

  • 1,596 Sq Ft
  • $360/SF
  • 140 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1962

  87 Witchtree Rd, Woodstock, NY 12498

  Stylish, well maintained Woodstock home. Set back from the road on a corner lot, framed by mature hardwoods and evergreens. This updated three bedroom, two and a half bath home features a double sided fireplace separating the living area from the dining area, a breakfast nook, and a wall of windows to let the sunshine in. Custom tile bathroom and walk-in shower adds to the charm and efficiency.

  Ruperto Ifil Halter Associates Realty

  87 Witchtree Rd, Woodstock, NY 12498
• 

  

  /33

  Est $728,381 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,678 Sq Ft

  282 Zena Rd, Kingston, NY 12401

  282 Zena Rd, Kingston, NY 12401
• 

  

  /44

  $550,000 Sold Oct 28, 2024

  • 2,520 Sq Ft
  • $218/SF
  • 54 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1962

  1 Oriole Dr, Woodstock, NY 12498

  Extremely spacious, well-laid out Colonial with loads of flex space for various needs in one of the loveliest suburbs south of the Village of Woodstock, with beautifully maintained and well-established gardens. One enters the driveway w/ ample parking and a 2 car garage w/ electric door with an interior entry. A hallway w/ a door to the deck also leads to a separate office space OR guest

  Hilton Purvis Coldwell Banker Village GreenN

  1 Oriole Dr, Woodstock, NY 12498
• 

  Est $991,387 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,554 Sq Ft

  688 Zena Rd, Woodstock, NY 12498

  688 Zena Rd, Woodstock, NY 12498
• 

  

  /37

  $575,000 Sold Oct 18, 2024

  • 2,609 Sq Ft
  • $220/SF
  • 65 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1964

  22 Oriole Dr, Woodstock, NY 12498

  If you are looking for a home that is close to the amenities and offer you the quiet comfort once home this is one to see. This home is set back from the road, offering privacy and tranquility. The landscaped, stone-terraced backyard is perfect for entertaining, or relaxing to the sounds of the birds and brook. As you step into the spacious foyer, you'll be greeted by an inviting, open layout.

  Patty Kowatch Keller Williams Realty HV Nort

  22 Oriole Dr, Woodstock, NY 12498
• 

  

  /35

  Est $843,167 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,707 Sq Ft

  52 Meher Cir, Woodstock, NY 12498

  52 Meher Cir, Woodstock, NY 12498

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