10 Great Luxury Homes in Woodstock, NY

Posted by Dylan Taft on Wednesday, December 21st, 2011 at 7:46am.

Woodstock, NY is probably the most well known town in the Hudson Valley region. Its legendary artistic streak and relative proximity to NYC make it an attractive mountain getaway for celebrities, musicians, and individuals of all kinds. But for those of you who appreciate the finer things in life along with your rugged surroundings, Taft Street Realty gives you a list of luxury Homes for Sale in Woodstock, NY!

23 Lewis Hollow Road - Woodstock, NY

A country home on over 20 acres, 23 Lewis Hollow Road epitomizes a Woodstock, NY retreat. With a private in-ground pool and a quaint guest house, this property is perfect for entertaining friends and family. Sited on over 20 acres of meadows and woodland, this home is private and secluded, yet just minutes from the thriving town of Woodstock, NY! Offered by Lisa Cooper of Westwood Metes and Bounds, Woodstock, this is a perfect country getaway or year-round estate ready for a new owner!

Address Unkown - Woodstock, NY

So amazing and mysterious that it has an unknown address in Woodstock, NY this one of a kind home has a soaring, open floor plan. Presented by Gary Heckelman of Coldwell Banker Village Green, this house first caught our attention while researching for our blog featuring the Top 10 Most Expensive Luxury Homes in Ulster, NY and we still can't stop dreaming about it! It's a mountain lodge from the future with a rustic yet contemporary design. Sited on 183 Acres(!) this is a modern-day castle fit for a king or queen!

30 Hill 99 - Woodstock, NY

The stunning mountain views, available from nearly every window, are what makes 30 Hill 99 so special. Throw in a screened in porch, small guest cottage, and sprawling 2nd floor studio and you've got a versatile and unique Woodstock, NY sanctuary! Offered by Amy Lonas of Coldwell Banker Village Green, this home has 2 master suites and 2 guest bedrooms leaving plenty of room for entertaining!

1835 Route 212 - Woodstock, NY

The past meets the present in this converted luxury 3,000 sqft(!) barn. Originally built in 1838, 1835 Route 212 still contains some of the original beams and flooring. Offered by Amy Lonas of Coldwell Banker Village Green, the centerpiece of the home is a beautiful 2-story fireplace complete with pizza oven! This is an artist's haven with a recording studio and additional apartment space in a separate, smaller, contemporary barn.

0 Cooper Lake Road - Woodstock, NY

00 Cooper Lake Road seamlessly blends state of the art sustainable design with classic aesthetics. Utilizing solar power, radiant heat, and other eco-friendly systems and materials, this home is really at one with the land around it. Fruit trees and indigenous gardens border the home completing the picture. Presented by Tecia Poulas of Prudential Nutshell Realty, this home combines state of the art sustainable living with classic appeal.

41 Falls Crossing - Woodstock, NY

"Halfway to Heaven" is the name given to 41 Falls Crossing and what a deserving name it is! Perched on top of 26 acres, this contemporary offers stunning mountain views from almost anywhere in the home. Presented by Lisa Halter of Coldwell Banker Village Green, this property features a private & secluded in ground pool, a home gym, and criss-crossing trails throughout the property. Live high atop your own mountain, yet minutes from the town of Woodstock, NY!

145 Ohayo Mountain Road - Woodstock, NY


This stone beauty offers elegant country living. 145 Ohayo Mountain Road is offered by Laurie Ylvisaker of Coldwell Banker Village Green. It features an accompanying art studio / guest house, built-in bookcases, and large windows to let in the natural light! All housed in the original stone structure. Additional 2-Car garage contains workshop for an artist's / handyman's delight!

7 Windsweep Lane - Bearsville, NY


7 Windsweep Lane overlooks a unique cluster of steep Catskill mountains that will make you feel like you're on another planet as you relax in your in-ground pool. Presented by Nina Schultz Terner of Westwood Metes & Bounds, this home was originally a small cottage with a new home basically built around it. 3 Stories and a master suite all contribute to the treetop feeling of this stunning house.

11 Grog Kill - Woodstock, NY


Surrounded by tall pines, with a waterfall view, 11 Grog Kill defines country sophistication. 10 ft ceilings, large windows and balconies all take advantage of surrounding mountain and waterfall views. Built in just 2007 with brand-new everything, this home is move-in ready and hassle free! Offered by Mitch Rapoport of Freestyle Realty

46 Raycliffe Drive - Woodstock, NY


46 Raycliffe Drive is perched on a cliff with breathtaking 180 degree views of the Hudson River, the surrounding Catskills, and even distant states on clear nights. Featuring a beautiful open floor plan with 2 master suites, the entire house offers its own unique view. Marble tiled bathrooms, gourmet kitchen, blue stone fireplace all add to the rugged luxury of this mountain retreat! Presented by Laurie Ylvisaker of Coldwell Banker Village Green.

... And That's Just Woodstock!

Woodstock, NY is a unique place to live, full of equally unique homes. But Woodstock is just one of the many interesting communities in Ulster County, NY! Though it may be the most famous of the town in the area (and with good reason) be sure to check out some of the other towns too, you never know when you'll come upon an amazing, hidden luxury home! Check back in on Taft Street Realty for the best Ulster County, NY blog!

More by this author - Luxury Woodstock NY Homes Under $750K

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