Zena, NY homes for sale & real estate

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NEW 24 HRS AGO

ABOUT THIS HOME
Zena, NY Homes for Sale
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. Most recent upgrades within the year include a new kitchen with marble and butcherblock counters, a completely renovated main bathroom, new roof, and more. The grounds are lovely with established perennials, level grassy meadow and woods to the rear. The front entry leads you through a cozy den, which is perfect for a reading or media room, and then beyond to the heart of the home - a bright and sunny open plan kitchen/living/dining area with wood burning stove. The large screened in porch is deliciously inviting for 3 season enjoymen

$695,000

3 beds2 baths1,842 sq ft

47 Van De Bogart Rd, Woodstock, NY 12498

New kitchen • Outdoor sauna • Flex space

OPEN SUN, 3PM TO 4PM

ABOUT THIS HOME
Zena, NY Homes for Sale
A STORYBOOK WOODSTOCK RETREAT IN THE WOODS Some homes provide shelter; others provide sanctuary. 357 Chestnut Hill Road is a sanctuary in the woods--a soulful Woodstock retreat where sunlight spills through skylights, pine glows underfoot, and the forest seems to lean in and whisper, ''stay awhile. '' Set on 1.6 wooded acres with approximately 257 feet of road frontage, this enchanting red-clad hideaway has been treasured by one close family since 1970. Follow the gravel drive beneath a leafy canopy and the home gradually reveals itself among the trees, its warm wood exterior appearing almost organically from the landscape. Secluded without feeling isolated, it captures the creative,

$595,000

2 beds1 bath1,338 sq ft

357 Chestnut Hill Rd, Woodstock, NY 12498

1.7 acre lot • Garage • Built 1970

ABOUT THIS HOME
Zena, NY Homes for Sale
Set on nearly an acre in the municipality of Woodstock with a Kingston address, this 1959 Cape Cod offers a combination of classic character, generous space, and excellent access to the Hudson Valley's most sought-after destinations. The home features three bedrooms, one full bath, approximately 1,351 square feet of living space on the first floor, plus an additional approximately 1,013 square feet unfinished space on the second floor. The expansive second level provides an exciting opportunity to create additional rooms, a private bedroom suite, studio, office, or other flexible living space, with the potential to add a second bathroom, subject to required permitting and approvals. Inside,

$475,000

3 beds1 bath1,351 sq ft

120 Sherman Rd, Kingston, NY 12401

Nearly an acre • Pellet stove • Built-in shelving

Listing by Howard Hanna Rand Realty

FLOOR PLAN

ABOUT THIS HOME
Zena, NY Homes for Sale
Family Compound and/or Investment Property. There are 3 homes at 5 & 7 Parker Lane in Woodstock. The property is located only minutes from Main St in Woodstock. The 5 Parker Ln cottage has 1423 square feet with 2 bedrooms & 1 bathroom. 7 Parker Ln has 2 homes on the lot. The 2-story home has 1231 square feet with 2 bedrooms & 1.5 bathrooms. The cabin at 7 Parker Ln has 1 bedroom & 1 bathroom. For this listing, I combined both 5 & 7 Parker Ln school tax, general tax, square footage, number of bedrooms, bathrooms and acreage. I can provide the separate details. When you are at the compound, there is a wonderful sense of privacy. There is a little pond behind the

$1,200,000

5 beds3.5 baths3,060 sq ft

5 & 7 Parker Ln, Woodstock, NY 12498

Shared pond • Investment property • Minutes from main st

FLOOR PLAN

ABOUT THIS HOME
Zena, NY Homes for Sale
Rarely does a Woodstock home come along with this much soul, flexibility, and built-in opportunity. Tucked away on just over an acre off private Chipmunk Lane, this charming 2265 sq ft Cape Cod cottage style home captures the feeling people come to Woodstock hoping to find: a little privacy, a little magic, a little room to create, and a home that feels deeply personal from the moment you arrive. At the heart of the main house is a wonderfully memorable kitchen, full of color, character, and warmth. This is not a showroom kitchen trying too hard. It is the kind of kitchen where meals stretch into stories, friends gather around the island, coffee starts slowly, and the house begins to feel l

$895,000

3 beds3 baths2,265 sq ft

15 Chipmunk Ln, Woodstock, NY 12498

Garden moments • Private parking • Separate driveway

Property at 171 Van Dale Rd, Woodstock, NY 12498, 3 beds, 2 baths

$599,000

3 beds2 baths1,824 sq ft

171 Van Dale Rd, Woodstock, NY 12498

Property at 5 Downer Ln, Woodstock, NY 12498, 4 beds, 4 baths

$1,200,000

4 beds4 baths3,172 sq ft

5 Downer Ln, Woodstock, NY 12498

Listing by Serhant LLC

Property at 72 Van Dale Rd, Woodstock, NY 12498, 3 beds, 3 baths

$699,000

3 beds3 baths1,991 sq ft

72 Van Dale Rd, Woodstock, NY 12498

Property at 29 Maurizi Ln, Woodstock, NY 12498, 4 beds, 2.5 baths

$799,999

4 beds2.5 baths2,372 sq ft

29 Maurizi Ln, Woodstock, NY 12498

Property at 5 - 7 Downer Ln, Woodstock, NY 12498, 5 beds, 5 baths

$1,700,000

5 beds5 baths4,628 sq ft

5 - 7 Downer Ln, Woodstock, NY 12498

Listing by Serhant LLC

Property at 1 Stone Ridge Ct, Woodstock, NY 12498, 4 beds, 2.5 baths

$799,000

4 beds2.5 baths2,584 sq ft

1 Stone Ridge Ct, Woodstock, NY 12498

Property at 97 John Joy Rd, Woodstock, NY 12498, 3 beds, 2 baths

$825,000

3 beds2 baths1,532 sq ft

97 John Joy Rd, Woodstock, NY 12498

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ABOUT THIS HOME
Zena, NY Homes for Sale
Welcome to 60 Pleasant Ridge Drive, West Hurley. This open and spacious ranch-style home is perfectly suited for a large family, entertaining, and everyday living. Beautifully maintained and welcoming, the home offers more than 3,000 square feet of finished living space, providing plenty of room to spread out and enjoy. Enter through the inviting front foyer into a massive, light-filled living room featuring hardwood floors, numerous windows, and a new freestanding gas fireplace that adds warmth and a cozy glow throughout the year. The oversized custom kitchen offers abundant workspace, making it easy for multiple cooks to work comfortably at the same time. The kitchen is equipped with a st

$625,000

4 beds2.5 baths3,178 sq ft

60 Pleasant Ridge Dr, West Hurley, NY 12491

Oversized deck • Walk-in closet • Garden window

ABOUT THIS HOME
Zena, NY Homes for Sale
Set in one of West Hurley's most welcoming neighborhoods, this beautifully maintained home offers a seamless blend of comfort, flexibility, and location. Tucked into a peaceful residential setting, the property is just minutes from Woodstock, Kingston, the Ashokan Rail Trail, and the region's many trails, swimming holes, restaurants, and cultural destinations. Located in the lower-tax town of West Hurley and within the Onteora Central School District, it is an appealing choice for full-time living, a weekend home, or an investment property. The main level offers a comfortable and inviting layout with generous natural light and well-proportioned living spaces. A screened-in porch extends fro

$649,000

3 beds2.5 baths3,064 sq ft

19 Pine Tree Rd, West Hurley, NY 12491

Propane stove • Screened-in porch • 0.69 acre lot

FOR SALE BY OWNER

ABOUT THIS HOME
Zena, NY Homes for Sale
Highly desirable one level end unit in Maverick Knolls. With three bedrooms, two bathrooms, an attached garage, and a screened-in porch, you can enjoy carefree living in a parklike setting. This unit has all new appliances, including a washer and dryer. Maverick Knolls offers a clubhouse, swimming pool, and tennis/pickleball courts. The HOA fee covers lawn care, snow removal, water, and garbage collection. A Woodstock address with low Hurley taxes.

$760,000

2 beds1.5 baths1,466 sq ft

31 Pond Park Rd, Woodstock, NY 12498

Screened in porch • Clubhouse • Swimming pool

ABOUT THIS HOME
Zena, NY Homes for Sale
Welcome to your sun lit cape nestled just outside the village of Woodstock and less than 100 miles from NYC. This serene property offers mature fruit trees and abundant plantings, stone walls and beautiful gathering space. Invite friends/family to stay in your private separate cottage or welcome them into your 3 bed 2 bath cape complete with 3 season room. The large cozy three-season room provides a tranquil setting to savor your morning coffee or enjoy gentle evening breezes. Having had only one owner you're sure to appreciate this well-maintained interior. Boasting with lovely hardwood floors throughout. The main level features a generous bedroom and a full bath equipped with custom built

$620,000

3 beds2 baths1,323 sq ft

342 State Route 375, West Hurley, NY 12491

Three season room • Mature fruit trees • Stone walls

ABOUT THIS HOME
Zena, NY Homes for Sale
This charming craftsman is situated in the perfect location, set back from the road yet only minutes to main street Woodstock and historic uptown Kingston. Well maintained, this sturdy gem boasts pristine hardwood floors, original trim and details, spacious eat-in kitchen and central air conditioning throughout. Room sizes are ample and offer flexibility of use and space. Added bonuses are the 2-car garage, full basement, cedar attic storage and a generous back yard graced with mature shade oaks, outdoor patio and even a little hill for sleigh riding. With plenty of parking and room for guests, 216 Williams is walking distance to the Trailways bus route, convenience store and across the str

$425,000

3 beds1 bath1,106 sq ft

216 Williams Ln, Kingston, NY 12401

Full basement • Cedar attic storage • 0.68 acre lot

ABOUT THIS HOME
Zena, NY Homes for Sale
A rare opportunity to own a truly special piece of the Hudson Valley. Nestled in the heart of Woodstock, NY, this iconic property offers 11.17 breathtaking acres of open meadows and sweeping mountain views that change beautifully with every season. The well-maintained 3-bedroom, 1-bath ranch house spans 1,360 square feet and offers comfortable single-level living with a warm, classic character. A charming red 4-stall barn - a nod to the property's days as a functioning horse property - adds tremendous character and versatility, complemented by a detached garage and shed for ample storage and utility. Whether you're looking for a private personal retreat, an equestrian revival, or a savvy in

$1,325,000

3 beds1 bath1,360 sq ft

94 Chestnut Hill Rd, Woodstock, NY 12498

Open meadows • Meandering stream • 4-stall barn

Property at 393 Ny-375, West Hurley, NY 12491, 4 beds

$400,000

4 beds— baths2,532 sq ft

393 Ny-375, West Hurley, NY 12491

Property at 317 New York 375 Unit West Hurley, NY 12491, West Hurley, NY 12491, 4 beds, 2 baths

$829,500

4 beds2 baths2,380 sq ft

317 New York 375 Unit West Hurley, NY 12491, West Hurley, NY 12491

Property at 328 John Joy Rd, Woodstock, NY 12498, 2 beds, 2 baths

$569,000

2 beds2 baths1,300 sq ft

328 John Joy Rd, Woodstock, NY 12498

Listing by Daniel Gale Sothebys Intl Rlty

Property at 40 Mamoud Hills, Lot #4 Rd, Kingston, NY 12401

$449,000

Land12.16 acres (lot)

40 Mamoud Hills, Lot #4 Rd, Kingston, NY 12401

Listing by Coldwell Banker Village Green

Property at 100 Zena Rd Unit sawkill road, Woodstock, NY 12498

$184,900

Land2.31 acres (lot)

100 Zena Rd Unit sawkill road, Woodstock, NY 12498

Based on information submitted to the MLS GRID as of Fri Sep 25 2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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$749,504

+5.4% YoY | Aug 2026

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Zena, NY

$749,504

+5.4%

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