Olivebridge, NY Homes

/48
$699,000 Pending
- 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

Win Morrison

Win Morrison Realty

(845) 506-1624

258 Watson Hollow Rd, West Shokan, NY 12494
/66
$6,500 per month
- 3 Beds
- 3 Baths
- 2,561 Sq Ft
- House for Rent
114 Chase Rd, Shokan, NY 12481

What an amazing place to spend the summer! Just 15 minutes from Woodstock and Phoenicia, you are right in the middle of all the Hudson Valley has to offer! Experience the rare opportunity to lease an extraordinary 70 acre estate where breathtaking natural beauty meets timeless sophistication.This reimagined three bedroom, 3 bath farmhouse blends rustic charm with refined modern luxury, creating a

Gail Cadden Coldwell Banker Village Green

114 Chase Rd, Shokan, NY 12481
/25
$475,000 Sold Dec 04, 2025

27 Crosswell Manor Dr, Shokan, NY 12481
- 3 Beds
- 3 Baths
- 2,900 Sq Ft
- Built 1971
Last Sold Summary
- 18% Below List Price
- $164/SF
- 161 Days On Market
Current Estimated Value $479,637

Last Listing Agent Laura Prince Hudson Dwellings Realty

27 Crosswell Manor Dr, Shokan, NY 12481

/33
Est $551,258 Not Listed For Sale

676 Wittenberg Rd, Mount Tremper, NY 12457
- 2 Beds
- 1 Bath
- 935 Sq Ft
- Built 1948
676 Wittenberg Rd, Mount Tremper, NY 12457

Last Sold Summary
- 8% Above List Price
- $548/SF
- 112 Days On Market
Last Sold Price $512,650

Last Listing Agent Barbara O'Hare Berkshire Hathaway Home Services

/42
$179,900
- 2 Beds
- 1 Bath
- 576 Sq Ft
449 Spillway Rd, West Hurley, NY 12491

Tucked away on just under 8 peaceful acres, this rustic two-bedroom, one-bath cabin offers a unique opportunity to create your own private retreat. The home features a full, unfinished attic with additional potential. Surrounded by mature trees, striking rock outcroppings, and historic hand-laid stone walls, the property is rich in character. A small stream winds through the land, and there is

Gianfranco Pellegri

Howard Hanna Rand Realty

(845) 524-1581

449 Spillway Rd, West Hurley, NY 12491
/23
$6,500 per month
- 4 Beds
- 2.5 Baths
- 1,853 Sq Ft
- House for Rent
11 Shultis Farm Rd, Bearsville, NY 12409

AVAIL FROM SEPT 2025. Private & Serene Modern Farmhouse Near Woodstock - Nestled on a private road just minutes from the heart of Woodstock, this beautifully renovated 4-bedroom, 2.5-bathroom modern farmhouse offers the perfect blend of charm, space, and privacy. Surrounded by mature trees, stone walls, and tall hedges, this home feels like a secluded retreat while remaining conveniently close to

Alexis Li Corcoran Country Living

11 Shultis Farm Rd, Bearsville, NY 12409
/48
$1,055,000 Sold Nov 13, 2025

4085 New York 28a, West Shokan, NY 12494
- 4 Beds
- 2.5 Baths
- 2,500 Sq Ft
- Built 1900
Last Sold Summary
- 10% Below List Price
- $422/SF
- 32 Days On Market
Last Listing Agent Quinn Hagstrand BHHS HUDSON VALLEY PROP-WDST

4085 New York 28a, West Shokan, NY 12494

/23
Est $347,136 Not Listed For Sale

27 Brunel Dr, Boiceville, NY 12412
- 3 Beds
- 1 Bath
- 1,032 Sq Ft
- Built 1977
27 Brunel Dr, Boiceville, NY 12412

Last Sold Summary
- 5% Above List Price
- $320/SF
- 149 Days On Market
Last Sold Price $330,000

Last Listing Agent Richard Greenspan Ruth Gale Realty

/11
$749,900
- Land
- 27.9 Acres
- $26,878 per Acre
Tbd New York 28, Boiceville, NY 12412

Incredible 27.9-acre development opportunity with mixed-use zoning and dual access from Route 28 and Upper Boiceville road. The front portion is zoned Highway Business with a 0.5-acre minimum, ideal for commercial use along this high-traffic corridor. The rear is zoned residential with a 1-acre minimum and could be subdivided for housing, a strip along the middle can go either way to be added to

Teresa Falkowski

Keller Williams Realty HV Nort

(845) 671-5010

Tbd New York 28, Boiceville, NY 12412
/16
$405,000 Sold May 12, 2025

7 Pinecrest Dr, West Shokan, NY 12494
- 3 Beds
- 2.5 Baths
- 1,672 Sq Ft
- Built 2001
Last Sold Summary
- 11% Below List Price
- $242/SF
- 161 Days On Market
Current Estimated Value $450,461

Last Listing Agent Ronnie Rebis Grist Mill Real Estate

7 Pinecrest Dr, West Shokan, NY 12494

/27
Not Listed For Sale

3647 Route 28a, West Shokan, NY 12494
- 2 Beds
- 2 Baths
- 1,710 Sq Ft
- Built 1945
3647 Route 28a, West Shokan, NY 12494

Last Sold Summary
- $530/SF
- 16 Days On Market
Last Sold Price $906,000

Last Listing Agent Baris Demirel Serhant LLC

/48
$1,350,000
- 3 Beds
- 2.5 Baths
- 2,100 Sq Ft
23 Traver Hollow Rd, Boiceville, NY 12412

Custom-Built Modern Home with Dramatic Mountain Views There are homes with views - and then there are homes built for the view. Affectionately known as Mountain Thyme, the mountain is not simply a backdrop but the defining presence of the property. From the moment you arrive, it rises dramatically into view, close enough to feel immersive, yet expansive enough to inspire. Designed to showcase the

Leigh Bokser

Compass Greater NY, LLC

(845) 609-1249

23 Traver Hollow Rd, Boiceville, NY 12412
$800,000 Sold Apr 15, 2025

987 Ashokan Rd, Kingston, NY 12401
- 2 Beds
- 2 Baths
- 1,925 Sq Ft
- Built 1952
Last Sold Summary
- $416/SF
- 31 Days On Market
Current Estimated Value $844,049

Last Listing Agent Donna Brooks Compass Greater NY, LLC

987 Ashokan Rd, Kingston, NY 12401

/51
Not Listed For Sale

342-344 Watson Hollow Rd, West Shokan, NY 12494
- 5 Beds
- 2.5 Baths
- 3,075 Sq Ft
- Built 1860
342-344 Watson Hollow Rd, West Shokan, NY 12494

Last Sold Summary
- $390/SF
- 90 Days On Market
Last Sold Price $1,200,000

Last Listing Agent Joseph Satto Fresh Air Realty

/39
$299,000 Pending
- 2 Beds
- 2 Baths
- 1,916 Sq Ft
2914 New York 28, Shokan, NY 12481

Affordable Two-Family Opportunity in Shokan! Set on 2 acres with frontage along Route 28, this two-family home is ready for its next chapter. The first-floor unit features 2 bedrooms and 1 bath; the second-floor apartment includes 1 bedroom and 1 bath—ideal for extended family, rental income, or offsetting your mortgage. The property needs renovation, but the potential is real for first-time

Elizabeth 'Beth' Alfeld

Keller Williams Hudson Valley

(845) 506-1533

2914 New York 28, Shokan, NY 12481
/66
$450,000 Sold Apr 23, 2025

17 Bostock Rd, Shokan, NY 12481
- 1 Bed
- 1.5 Baths
- 1,349 Sq Ft
- Built 1946
Last Sold Summary
- 10% Below List Price
- $334/SF
- 111 Days On Market
Current Estimated Value $440,417

Last Listing Agent Darlene Griffin Halter Associates Realty

17 Bostock Rd, Shokan, NY 12481

/51
Not Listed For Sale

8 Heyden Off Chase Rd, Shokan, NY 12481
- 3 Beds
- 2 Baths
- 3,725 Sq Ft
- Built 1997
8 Heyden Off Chase Rd, Shokan, NY 12481

Last Sold Summary
- $348/SF
- 28 Days On Market
Last Sold Price $1,295,000

Last Listing Agent Carol Spirig Halter Associates Realty

/34
$1,990,000 New Construction
- 3 Beds
- 2.5 Baths
- 2,775 Sq Ft
30 Narrow Rd, Kingston, NY 12401

Welcome to Ashokan Forest Haven, a one-of-a-kind escape located between the heart of Stone Ridge and the Ashokan Reservoir. Constructed in 2024, the Haven is composed of clean lines, carefully considered finishes, and an ecological ethos creating a backdrop for adventurous, effortless living harmonized with its forest surroundings. This property can cater to a variety of lifestyles, whether

Veronica Newton

Compass Greater NY, LLC

(329) 210-1502

30 Narrow Rd, Kingston, NY 12401
/59
$407,000 Sold Dec 16, 2025

20 Beechford Dr, Boiceville, NY 12412
- 2 Beds
- 2 Baths
- 1,404 Sq Ft
- Built 1980
Last Sold Summary
- 3% Below List Price
- $290/SF
- 26 Days On Market
Current Estimated Value $416,257

Last Listing Agent Karen Gilbane Corcoran Country Living

20 Beechford Dr, Boiceville, NY 12412

Not Listed For Sale

1345 Wittenberg Rd Unit 1347, Mount Tremper, NY 12457
- 4 Beds
- 3.5 Baths
- 2,174 Sq Ft
- Built 1987
1345 Wittenberg Rd Unit 1347, Mount Tremper, NY 12457

Last Sold Summary
- $396/SF
- 15 Days On Market
Last Sold Price $860,000

Last Listing Agent Valerie Cashen Coldwell Banker Village Green

/67
$6,995,000
- 9 Beds
- 7 Baths
- 8,479 Sq Ft
1471 New York 28a, West Hurley, NY 12491

Welcome to one of the most exceptional private estates in the Hudson Valley—a rare and breathtaking 115-acre estate overlooking the shimmering waters of the Ashokan Reservoir and framed by sweeping Catskill Mountain vistas. This once-in-a-generation offering comprises three distinct residences, three separately deeded parcels, extensive manicured trails, and an unmatched suite of amenities—all

Richard Vizzini Corcoran Country Living

1471 New York 28a, West Hurley, NY 12491
/53
$509,250 Sold Jun 13, 2025

54 Hillside Dr, West Shokan, NY 12494
- 3 Beds
- 1.5 Baths
- 1,624 Sq Ft
- Built 1996
Last Sold Summary
- 7% Below List Price
- $314/SF
- 181 Days On Market
Current Estimated Value $519,844

Last Listing Agent Edwin Maldonado Howard Hanna Rand Realty

54 Hillside Dr, West Shokan, NY 12494

/35
Est $885,565 Not Listed For Sale

460 Glenford Wittenberg Rd, Bearsville, NY 12409
- 2 Beds
- 2 Baths
- 2,156 Sq Ft
- Built 1990
460 Glenford Wittenberg Rd, Bearsville, NY 12409

Last Sold Summary
- 11% Above List Price
- $371/SF
- 28 Days On Market
Last Sold Price $800,000

Last Listing Agent Lisa Cooper Serhant LLC

/34
$1,199,000 Under Contract
- 3 Beds
- 3.5 Baths
- 2,960 Sq Ft
584 Acorn Hill Rd, Olivebridge, NY 12461

Nestled on 2.9 acres on a country road in Olivebridge, this newly constructed residence offers a harmonious balance of contemporary elegance and the beauty of nature. Spanning nearly 3,000 square feet, this thoughtfully crafted home features 3 bedrooms, 3.5 baths, and a flex space ideal for an office, studio, or den. Each space has been designed with meticulous attention to detail, keeping modern

Richard Vizzini Corcoran Country Living

584 Acorn Hill Rd, Olivebridge, NY 12461
$850,000 Sold May 08, 2025

363 Cold Brook Rd, Bearsville, NY 12409
- 3 Beds
- 2 Baths
- 3,126 Sq Ft
- Built 1985
Last Sold Summary
- 23% Below List Price
- $272/SF
- 117 Days On Market
Last Listing Agent Carol Spirig Halter Associates Realty Inc

363 Cold Brook Rd, Bearsville, NY 12409

/2
Est $3,637,377 Not Listed For Sale

1073 Wittenberg Rd, Mount Tremper, NY 12457
- 5 Beds
- 4 Baths
- 3,848 Sq Ft
- Built 1926
1073 Wittenberg Rd, Mount Tremper, NY 12457

Last Sold Summary
- 4% Below List Price
- $988/SF
Last Sold Price $3,800,000

Last Listing Agent Lisa Halter Halter Associates Realty Inc

/37
$1,375,000 Under Contract
- 4 Beds
- 4 Baths
- 6,805 Sq Ft
174 Bristol Hill Rd, Glenford, NY 12433

Nestled on a quiet cul-de-sac, where forested hills meet glimpses of the shimmering Ashokan Reservoir, this contemporary residence offers an expression of scale, privacy, and refined Catskills living. Set across 2 acres and encompassing an impressive 6,805 square feet, the residence blends architectural design with the serenity of its natural surroundings. Inside, discover interiors defined by

Richard Vizzini Corcoran Country Living

174 Bristol Hill Rd, Glenford, NY 12433
/34
$840,000 Sold Jul 08, 2025

516 Watson Hollow Rd, West Shokan, NY 12494
- 4 Beds
- 2 Baths
- 2,345 Sq Ft
- Built 1973
Last Sold Summary
- 3% Above List Price
- $358/SF
- 19 Days On Market
Current Estimated Value $861,670

Last Listing Agent Diana Polack Compass Greater NY, LLC

516 Watson Hollow Rd, West Shokan, NY 12494

Est $593,339 Not Listed For Sale

403 Wittenberg Rd, Bearsville, NY 12409
- 3 Beds
- 2 Baths
- 2,071 Sq Ft
- Built 1875
403 Wittenberg Rd, Bearsville, NY 12409

Last Sold Summary
- 37% Above List Price
- $209/SF
- 362 Days On Market
Last Sold Price $432,000

Last Listing Agent MaryBeth O'Hara Ellis Sotheby's Intl Realty

/50
$2,000,000
- 4 Beds
- 3 Baths
- 3,671 Sq Ft
53 Freeman Avery Rd, Olivebridge, NY 12461

An architectural gem tucked away on 40 acres of pristine forest, this striking 3,671-square-foot residence is a stunning fusion of modern architecture and natural beauty. Crafted by the acclaimed Resolution: 4 Architecture, incorporating all of their most coveted features that converge in this divine mid century modern design. Travel down the tree lined driveway past a cascading waterfall to a

Richard Vizzini Corcoran Country Living

53 Freeman Avery Rd, Olivebridge, NY 12461
/46
$441,000 Sold Jul 22, 2025

3273 New York 28, Shokan, NY 12481
- 4 Beds
- 4 Baths
- 1,404 Sq Ft
- Built 1910
Last Sold Summary
- 4% Above List Price
- $314/SF
- 118 Days On Market
Current Estimated Value $448,943

Last Listing Agent Rodney Batista Howard Hanna Rand Realty

3273 New York 28, Shokan, NY 12481

Est $603,703 Not Listed For Sale

617 Wittenberg Rd, Mount Tremper, NY 12457
- 3 Beds
- 2 Baths
- 1,789 Sq Ft
- Built 1928
617 Wittenberg Rd, Mount Tremper, NY 12457

Last Sold Summary
- 10% Above List Price
- $307/SF
- 157 Days On Market
Last Sold Price $550,000

Last Listing Agent Danielle Marchisella Corcoran Country Living

/36
$1,100,000 Pending
- 4 Beds
- 5 Baths
- 3,522 Sq Ft
54 Tetta Ln, Olivebridge, NY 12461

New barn-style home going up on 7+ acres in Olivebridge. Lots of space spread out over 3 floors. Plenty of exterior porches as well. Quiet, private, and pretty.,AboveGrade:3522,Below Grnd Sq Feet:1269,FLOORING:Wood,FOUNDATION:Concrete,OTHERROOMS:Family Room,Formal Dining Room,Office/Computer Room,ROOF:Asphalt Shingles,Unfinished Square Feet:217

Chuck Petersheim Lazy Meadows Realty

54 Tetta Ln, Olivebridge, NY 12461
/51
$945,000 Sold Sep 30, 2025

11 Heyden Rd, Shokan, NY 12481
- 3 Beds
- 2 Baths
- 1,794 Sq Ft
- Built 1949
Last Sold Summary
- $527/SF
- 71 Days On Market
Last Listing Agent Darlene Griffin Halter Associates Realty

11 Heyden Rd, Shokan, NY 12481

Est $433,534 Not Listed For Sale

913 Wittenberg Rd, Mount Tremper, NY 12457
- 2 Beds
- 1 Bath
- 957 Sq Ft
- Built 1966
913 Wittenberg Rd, Mount Tremper, NY 12457

Last Sold Summary
- 10% Above List Price
- $413/SF
- 244 Days On Market
Last Sold Price $395,000

Last Listing Agent Dennis Bressack Keller Williams Hudson Valley

/37
$890,000 Under Contract
- 3 Beds
- 2.5 Baths
- 2,184 Sq Ft
2246 County Road 3, Olivebridge, NY 12461

Nestled at the base of the Ashokan High Point mountain, one of the Catskills' most scenic peaks, this beautifully appointed, rustic 5.7-acre retreat is set back generously from a quiet country road just minutes from the Ashokan Reservoir. Custom built in 2000, the stylish, move-in-ready home features multiple great spaces for gathering with friends and family, both inside and out, starting with

Hayes Clement Compass Greater New York, LLC

2246 County Road 3, Olivebridge, NY 12461
/47
$976,000 Sold Nov 10, 2025

3 Hanna Ln, Olivebridge, NY 12461
- 3 Beds
- 2.5 Baths
- 1,986 Sq Ft
- Built 2020
Last Sold Summary
- 6% Above List Price
- $491/SF
- 21 Days On Market
Current Estimated Value $973,682

Last Listing Agent William Golan Compass Greater NY, LLC

3 Hanna Ln, Olivebridge, NY 12461

/34
Est $582,086 Not Listed For Sale

618 Wittenberg Rd, Mount Tremper, NY 12457
- 3 Beds
- 2 Baths
- 1,329 Sq Ft
- Built 1981
618 Wittenberg Rd, Mount Tremper, NY 12457

Last Sold Summary
- 12% Above List Price
- $389/SF
- 30 Days On Market
Last Sold Price $517,625

Last Listing Agent Sharon Breslau Berkshire Hathaway Home Services

/51
$1,275,000 Pending
- 3 Beds
- 2.5 Baths
- 3,581 Sq Ft
483 Acorn Hill Rd, Olivebridge, NY 12461

Set along quiet Acorn Hill Road, this thoughtfully designed Catskills retreat delivers a rare balance of privacy, polish, and everyday convenience. Built in 2022, the home feels intentionally set apart, a place where calm and comfort take center stage, while favorite destinations remain just minutes away. Life unfolds with ease here. Mornings begin on the wide front porch with coffee in hand,

Emily Daniels BHHS Nutshell Realty

483 Acorn Hill Rd, Olivebridge, NY 12461
/11
$205,000 Sold Mar 13, 2026

3382 State Route 28, Shokan, NY 12481
- 2 Beds
- 1 Bath
- 1,077 Sq Ft
- Built 1921
Last Sold Summary
- 38% Below List Price
- $190/SF
- 292 Days On Market
Current Estimated Value $280,169

Last Listing Agent Siobhan Scanlan Win Morrison Realty-K

3382 State Route 28, Shokan, NY 12481

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