Chatham NY Real Estate & Homes for Sale

River Road, set amongst the rolling hills of picturesque Hillsdale you'll find this turn of the century farmhouse set on 20 acres of sprawling meadows and wildflower fields. The storybook approach follows River Road alongside the rushing Green River and up a private drive overlooking mountain ridges and whimsical tall pines. The c1890 farmhouse welcomes you with its wraparound porch and fieldstone front steps. Inside the rooms are large, the living room and master bedroom are both anchored by a magnificent stacked stone fireplace, recently restored and in use. The dining room opens to the wrap around porch through french doors, and when opened the sound of the rushing Green River flows through the house. Tucked around a corner you'll find an outdoor shower overlooking the water. The kitchen is recently redone with brand new appliances and herringbone countertops, and the ground floor features an office and a full bath, which could be used as a fourth bedroom. Upstairs, all three bedrooms have ensuite baths with wonderfully deep soaking tubs, each with beautiful views of forest, pond and river. Windows, siding, roof, insulation, HVAC and floors are all brand new, allowing the next owner to own a beautiful antique farmhouse with little to no maintenance. A separate studio lies up the hill, used for creative projects by the current owners but open for future possibilities. This incredibly charming property is just 10m to the village of Hillsdale, 15m to Great Barrington and 2h to NYC.

There are few homes as fine a seed as this one. Set on a quiet 6.9 acre parcel in the rolling hills of Chatham, The Seedling is a beautiful custom designed home with room to grow. The home lives large, with the centerpiece being a lofted great room, featuring a double helix staircase to an oversized loft, and a granite hearth. The soaring windows and sliding doors bring light streaming into the open plan living and dining rooms, and there is ample room to entertain. A fully equipped kitchen and powder room round out the living space. The primary suite features two sets of sliding doors for privacy, and a large and light-filled bedroom with sliding glass doors to the yard. Downstairs, you'll find a huge finished basement, ripe to be set as a guest suite, entertainment room, or a combination of uses. The basement is 502 square feet with dedicated laundry and storage rooms.

This extraordinary, newly updated 16 acre oasis offers a tranquil retreat for the weekender or if you are lucky to live here full time. Meander down the paved 1/4 mile driveway and your private world of serenity awaits. Included is a stunning kitchen with new granite counter tops, built-in appliances, custom inlaid hardwood floors, newly updated baths and trim. The open floor plan allows you to entertain guests while you're in the kitchen. After dinner you can retreat to the family area with propane fireplace or for those warm nights exit to the oversized decking. Just some of the amenities this home boasts are a lighted tennis court, in-ground pool and spa, knotty pine paneled billiard room and sauna. Updated HVAC system, well pump and roof. The oversized 3 car garage features a 50 amp RV/EV hookup. Just 30 min to Hudson.

Welcome to the Elijah Hudson homestead and farm, nestled in the hamlet of Malden Bridge, NY. Steeped in rich history dating back to the mid1700s, this property boasts a captivating past as a colonial-era inn, meeting place for traveling preachers, and farm of a co-founder of the Federal Stores mercantile (Old Chatham). The homestead, lovingly restored over decades, offers a glimpse into the region's storied past, with original features meticulously preserved alongside modern updates for comfortable living. The property encompasses 43 acres of picturesque land, including sprawling fields, pristine gardens, and tranquil woods teeming with wildlife. Two meticulously restored barns, including a stunning German horse barn and a Dutch dairy barn, stand as testaments to the property's enduring legacy. The Dutch barn, fully rebuilt in recent years, presents a blank canvas for the next owner's vision, while the German barn offers versatile finished spaces for entertainment, hobbies, and more. Experience the best of country living in this idyllic retreat, where generations have gathered to celebrate life's milestones and forge lasting memories. With its proximity to local amenities, recreational opportunities, and vibrant community life, the Elijah Hudson homestead offers an opportunity to own a piece of living history in the heart of upstate New York. Don't miss your chance to write the next chapter in this timeless legacy. Property Improvement Highlights This meticulously maintained property has seen numerous upgrades and renovations over the years, ensuring modern comfort without compromising its historic charm. Recent improvements include an upgraded bath and laundry rooms, a complete restoration of the Dutch barn, and exterior painting of both barns, among others. With a commitment to preserving its heritage while embracing modern living, the Elijah Hudson homestead is ready to welcome its next steward into a future filled with possibility.

Former Schoolhouse Completely Redone 1840s One room schoolhouse with the most amazing floors and exposed beams. Come in through the original entrance! The classroom is now a living room with a fireplace and full bath. The expansive and well appointed kitchen has all locally crafted handmade cherry cabinets. A den just off the kitchen is perfect for a post dinner chat. The french doors lead out to a stone patio, a small barn and the old outhouse! Upstairs there are two huge bedrooms with large closets. Set on over 5 acres on a gorgeous country road.

A long winding country road, a dirt driveway, a fifty acre sanctuary. This stunning post & beam barn house sits on a one acre pond amid fields & fields of wildflowers and deep pine forest. Built by a premier builder in the area, the contemporary home has 20ft ceilings, a giant expanse that feels warm and inviting. The home is longer than it is wide with a substantial kitchen at the center. A large island and dining table run side by side, and you'll find high end appliances in a sharp, polished black finish. A wood burning stove sits between the kitchen and living room, and a den sits in the northwest corner. This entire first floor looks out over the pond to the fields in the distance. Upstairs, you have a giant open loft overlooking the main living space, a bedroom with gorgeous views of the property and a full bath. Antique fixtures such as faucets, sinks and hardware are interspersed throughout the home, and the post and beam construction incorporates reclaimed hand hewn beams, making this new build feel authentic and well beyond its years (in a good way). Radiant heated concrete floors span the lower level of the home where you'll find three bedrooms. Two share a full bath, and one is ensuite with a large, walk-in closet and glass doors leading outside to a pebble patio overlooking the water. There is also a sitting room on the lower level, light and bright, with sliding glass doors that lead outside. The entire house is west facing and enjoys fabulous sunsets. A cottage is tucked back against the tree line, as charming as could possibly be with a full kitchen, a large bedroom and a full bath. 2.5h to NYC, 2.5h to Boston, 30m to Hudson and Amtrak. Dorland Farm is a little slice of Hudson Valley heaven.

The Every House has the soul of an artist and offers a little something for everyone. A pond for reflecting a pool for a cool dip. A quiet road to walk on. Proximity to Chatham for life's essentials. The mudroom is where you start, shedding boots and coats. Upstairs a country kitchen looks out over the grounds keeping things in perspective. The living room is large enough for formal and informal coexist, anchored by the fireplace. The sunroom serves as a dining room for light filled soirees. First floor bedroom with full bath and steam shower. Upstairs 3 large bedrooms. Third floor office. Amazing carriage house with 2 bedroom apartment. Fruit trees and gardens!

One of the few brick Georgians in Columbia County, the Samuel Wilbur House is a stately reminder of the past. Wilbur, a NYS Senator during the Colonial era, created a home of outstanding beauty and balance. Huge original barns, renovated Carriage House, 20 x 40 heated, saltwater pool, bluestone patios and stream give the outdoor space an instant country feel. The home consists of five separate but connected living spaces, each with their own kitchen, baths and bedrooms. A family compound in a single building, a small inn or bed and breakfast. All of the finishes are of the highest quality, with many of the original details intact. The floors have over a century of patina, the moldings are hand crafted, the fireplace mantels works of art, exposed beams and bricks lend interest to the ceilings and walls. Updated where it's needed, particularly in the main kitchen where modern aesthetics give clean thought to this antique beauty. Wonderful new windows bring in the light and amazing original windows, including the original Palladian window in the upper hall,FOUNDATION:Brick,Masonry,Block,Concrete,OTHERROOMS:Library/Study,Sun Room,In-Law,Workshop,Formal Dining Room,Great Room,Office/Computer Room,AboveGrade:5195,AMENITIES:Pool,ROOF:Asphalt Shingles,FLOORING:Tile,Ceramic Tile,Wood