Chatham, NY Houses for Sale

Welcome home! This sweet cape is sure to charm. Enjoy a cozy, well maintained home on an acre of property! Great size kitchen, open to the dining area for ease when entertaining. Bedroom and full bath on the first floor. Two more bedrooms upstairs. Enjoy the convenience of a spacious mudroom to house your shoes and outdoor gear. Great location! Less than 3 hours to NYC, 30 minutes to Albany & 30

Kevin Clancy Clancy Real Estate

Welcome to your dream retreat! This incredible compound offers 9 bedrooms, 6 bathrooms, and nearly 10 acres of pure serenity. The stunning great room is the showstopper—surrounded by windows and boasting a massive open floor plan. Enjoy a chef's kitchen with island, bar stool seating and stainless steel appliances. Enjoy beautiful stone fireplace and wood stoves to keep you and guests nice and

Kevin Clancy Clancy Real Estate

5.79 acres in beautiful location w/privacy off secondary rd w/woods on all sides. Pond stocked w/lg mouth bass, landscaping, att one car garage, separate storage shed. Low maintenance Colonial style house w/brick & vinyl siding. Second floor en-suite primary on one end & three BRs + full bath on other end. Can be a five BR if needed. Revel in the tranquility of this 2,860 sq. ft. residence by the

Frances Ingraham Heins Howard Hanna Capital Inc

Step back in time without sacrificing modern amenities in this fully renovated 1850's farmhouse, nestled on an expansive 163+ acre estate set within serene woods. This exceptional property offers a rare combination of historic charm and contemporary convenience, featuring 4 bedrooms and 4.5 modern baths - each designed during a down to the studs renovation completed within the last 10 years. The

Faith Adamec RE/MAX Capital

Own a piece of Old Chatham history with the distinguished Samuel Wilbor House. Built circa 1770 and listed on the National Register of Historic Places, the estate includes a beautifully updated main house, three stylishly renovated apartments, and a converted barn. The main house features white pine woodwork, four fireplaces, an original Palladian window, and a large kitchen with floor-to-ceiling

Anthony D'Argenzio Houlihan Lawrence

At the heart of this timeless hamlet sits The Chatham House, offering a poetic blend of early American architecture and modern ease. Thoughtfully evolved over centuries, the home preserves its soul while embracing the comforts of today.Inside, light spills through elegant original windows and into the sweeping central hall and formal sitting rooms on either side of the house. A library

Alexandra Demetrakis Upstate Down

Nestled in a serene, wooded setting, 326 Pratt Hill Road is a thoughtfully designed Cape-style home that blends rustic charm with modern comforts. Originally a quaint cabin, it has been carefully expanded over the years and now offers three bedrooms, two full bathrooms, and 8.1 private acres – perfect for a weekend escape or year-round living. The oversized living area features hardwood floors, a

Callan Bergmann Compass Greater NY, LLC

A post and beam barn on a dead end road in Old Chatham. Cathedral ceilings, walls wrapped in windows, bring in light and views from every angle. In the great room a brick fireplace with a chestnut mantle. Open floor plan makes it easy for entertaining. Shaker cabinets, soapstone counters, and hand crafted lighting. First floor primary bedroom ensuite with walk in closet. Two additional bedrooms

Emma French Gabel Real Estate

Welcome to Bezalel Gables, where history meets elegance in this Queen Anne Victorian home, built in 1873 for a State Senator and nestled on an expansive 21 acres. This home boasts an impressive layout, featuring spacious living areas perfect for both intimate gatherings and grand entertaining. Venture outside, and you'll discover your own private oasis. The lush 21 acres are adorned with mature

Tammy Molinski Coldwell Banker Advisor Realty

Elegantly poised on 56.47 acres in Chatham, NY, paved driveway leads to a private oasis surrounded by lush, mature flower gardens, fruit and flowering trees, open fields, and a vast organic vegetable garden.This exceptional estate embodies the very essence of luxury living, thoughtfully designed for those who cherish nature. Expansive windows throughout the home frame stunning views at every

Vera Cohen Vera Cohen Realty, LLC

Elegantly poised on 56.47-acres, this exceptional estate encapsulates the very essence of luxury living. A pristine pond, versatile outbuildings, organic garden & panoramic mountain views create a magnificent backdrop of natural splendor. The interior unfolds as a symphony of lavish indulgence, boasting the finest appliances, a sauna, 2 executive offices, a wet bar, outdoor kitchen. A sprawling

Vera Cohen Vera Cohen Realty, LLC

Charming two-story Home on a country road near Old Chatham. This delightful home offers 3 bedrooms and 1.5 baths, perfectly nestled on a quiet country road just minutes from Old Chatham. Being sold as-is with the interior contents included, it's a wonderful opportunity for those seeking a peaceful escape from the city or an ideal investment for an Airbnb. Bring your vision and make this home

Mary Stapleton Berkshire Hathaway HomeService

Welcome home!This thoughtfully restored 1880's village residence maintains its original integrity. The home has been meticulously renovated, featuring spacious rooms with lofty ceilings, abundant natural sunlight, and beautiful hardwood floors throughout.A beautiful front entryway opens to an elegantly curved staircase and parlor. Just beyond the French doors an inviting dining

Lenore Packet Stone House Properties, LLC

Charming and walkable 4BR home in the heart of Chatham village! Set on a spacious half-acre lot, this sun-filled home blends original character with modern updates—featuring hardwood floors, a flexible layout with home office/music room, and plumbing in place for a second bath. Enjoy golden hour on the front porch or entertain in the deep, private backyard with a stone patio. Steps to yoga,

Joseph Briggs William Pitt Sotheby's

Depot LaneNestled at the end of a quiet country lane, this charming historic home in the hamlet of Old Chatham offers the perfect blend of rural tranquility and warm community connections. Surrounded by sprawling gardens and quiet woods, the first floor of this peaceful retreat offers a spacious living room, complete with a wood-burning fireplace, an inviting eat-in kitchen perfect for family

Andrea Gabel Gabel Real Estate

Contractor Special: Office building ready for transformation to many possibilities. Common areas can accommodate open living/dining/kitchen concepts. Wideboard floors throughout. Attached shed serves as ample storage. A detached three bay garage is also on this 1.5 acre lot. Bring your vision for single-floor living to this blank slate just outside of Chatham Village.

Jennifer Wall Anderson Agency

Welcome to Dogwood Cottage! Tucked along one of the most darling streets in the Village of Chatham, Dogwood Cottage is a storybook gem framed by the blooms of its namesake tree. Set on a sweet quarter-acre lot, this 3 bedroom, 2 bath 1945 ''Victory Cottage'' offers the perfect blend of charm, privacy, and village convenience.Inside, natural light pours through every room, highlighting the warmth

Brittany Craig Houlihan Lawrence Inc.

In the heart of Old Chatham, is this rare opportunity to purchase a historic, well maintained, 3 unit property with views of breathtaking, cascading waterfalls. The Old Chatham Post Office currently occupies one unit (3 years remain on the lease) and, there are 2 updated, currently vacant apartments to rent, live in or use as office space. The two level, 2 bedroom apartment and a 1 (could be 2)

Peter Newman Beach & Bartolo Realtors

Calling all Barn Lovers and Period Home Restorers! Come reimagine a legacy. Nestled on nearly 2 rolling acres of meadow and sky, This Old East Chatham Farmhouse invites you to revive a piece of Columbia County's earliest roots. Built in 1820 and rumored to be one of the area's oldest homes, this storied brick farmhouse still holds echoes of its past—wide-plank heart pine floors (milled from

Brittany Craig Houlihan Lawrence Inc.

Step back in time with this enchanting 1820s village Colonial, a true jewel box filled with original details and timeless charm. This home exudes warmth and tranquility, featuring high ceilings, wide plank floors, and both front and back staircases leading to three generously sized bedrooms. A hidden ''secret'' nook offers the perfect space for hide-and-seek, quiet reflection, or a cozy

Jonathan Hallam The Kinderhook Group, Inc.

Was on the market before as just a shell. You have to see it now that it is redone and almost finished. Only room not yet finished is the kitchen for you to add your personal touch. New everything inside and out. New septic and well, new front landscaping, new siding, roof, furnace, hot water heater, insulation, wiring, plumbing, hardwood floors downstairs, windows and doors. Downstairs bedroom

Karen Westman BERKSHIRE HATHAWAY HOME SERVICE BLAKE

A Chatham farm property with endless possibilities. Anchoring this 7-acre parcel is a 3BR, 3-1/2 BA home surrounded by fields, paddocks and woodlands. Set off from the home is an amazing barn complex and spring-fed pond. All less than a minute to downtown Chatham and equally close to the Taconic Pkwy. The property abuts the 65-acre Borden Pond conservation land - a hiker's paradise. The barn

Jason Karadus Corcoran Country Living

Welcome to The Anson Pratt House, a masterfully restored Federal Adams-style residence located in the historic hamlet of New Concord in East Chatham, NY. Built in 1793 atop a marble clad foundation, this architectural jewel is honored in the Library of Congress as part of the Historic American Buildings Survey. Featured in numerous architectural and design publications, The Anson Pratt House is

Rachel Haley Houlihan Lawrence Inc.

Granite counter top going in this week rest of the kitchen is in.Was on the market before as just a shell. You have to see it now that it is redone and almost finished. New everything inside and out. New septic and well, new front landscaping, new siding, roof, furnace, hot water heater, insulation, wiring, plumbing, hardwood floors downstairs, windows and doors. Downstairs bedroom ensuite

Leonard Brown Berkshire Hathaway HomeService

Granite counter top going in this week rest of the kitchen is in.Was on the market before as just a shell. You have to see it now that it is redone and almost finished. New everything inside and out. New septic and well, new front landscaping, new siding, roof, furnace, hot water heater, insulation, wiring, plumbing, hardwood floors downstairs, windows and doors. Downstairs bedroom ensuite

Sharon McArdle Berkshire Hathaway Home Services Blake

The Waterfall House is a modernist masterpiece, uniquely defined by its own cascading waterfall--a view you can enjoy from every room. Wade in the serene swimming hole below or wander through the exquisitely landscaped gardens that surround the home. Cozy up by the living room fire and admire the waterfall through a dramatic wall of glass.Designed to exist in perfect harmony with its natural

Lisa Bouchard Hoe The Kinderhook Group, Inc.

Tucked into the heart of the Hudson Valley, where life slows and nature flourishes, lies Foxglove & Fern a breathtaking 101-acre sanctuary. As you follow the circular driveway, rolling meadows, ancient trees, and a shimmering private pond welcome you to a world of serenity.More than a home, this estate is a legacya place where generations gather, and every sunrise brings new adventures. The main

Heather Etzel Four Seasons Sotheby's Int.

At the end of a dead end road. Close to Chatham yet a world of privacy. 1874 gem with a post and beam barn to drool over. Historic cottage with original floors. Handcrafted features. Cherry kitchen with great storage and workspace. Dining area open to a deck overlooking the blooming bulbs, ornamental trees, flowering shrubs and picture perfect vegetable and cutting garden. Two bedrooms. Huge

Tracy Tassinari Gabel Real Estate

CEDAR HILL - A HOUSE for all SEASONSBathed in sunlight, this graceful architectural masterwork is perfectly sited on ten private acres with awe-inspiring panoramic southern mountain views stretching endlessly, offering an ever-changing magical canvas of light and landscape. A home for all seasons, this newly re-built and expanded cedar house stands as if it rose from the

Nancy Felcetto Brown Harris Stevens Hudson

Tucked in the Hudson Valley, Foxglove & Fern is a 101-acre sanctuary where rolling meadows, ancient trees, and two ponds create a peaceful retreat. The 7-bedroom main house exudes warmth, with an inviting living room, a dining room anchored by a hand-laid stone fireplace, and a kitchen designed for gathering. A detached office offers endless possibilities—an artist's studio, a private retreat, or

Heather Etzel Four Seasons Sotheby's International Realty