Chatham, NY Homes for Sale with Garage

Welcome to Chicory Hill House, a unique designer home set at the end of a long private driveway on 20 beautiful acres located in Columbia County, prime Hudson Valley. The property features pastoral views, a year-round creek, and a small waterfall woven into the landscape. Following an extensive high-end renovation and infrastructure overhaul, the original 1985 contemporary has been transformed

Anthony D'Argenzio Houlihan Lawrence

Refined and classic elegance abounds in this historic and prominent Spencertown hamlet home. Built in 1810 as a fashionable Federal Style home, it featured magnificent details and craftsmanship throughout. Step back in time in this glorious and updated property. The abundance of 19th century luxury features have been lovingly restored and enhanced from the polished original flooring, window

Peter Newman Beach & Bartolo Realtors

Located on one of Columbia County's finest roads in the town of Spencertown, this impeccably-maintained private 2922 sq ft. colonial home on 7.4 acres has all of the modern amenities! A fabulous setting with stunning distant views, the home features an open chef's kitchen and great room plan, which was expanded and redesigned in 2021, with Sub Zero refrigerator, Wolf gas oven and Miele dishwasher

Janet Kain The Kinderhook Group, Inc.

Set in the heart of Old Chatham, this classic Colonial rests on an exceptional 101-acre landscape of rolling pasture, woodland, and wide-open country views. From its elevated vantage point, the home looks out over a 2.5-acre swimmable pond, open fields, and a stretch of Hudson Valley scenery that changes beautifully with the seasons. Flooded with natural light, the seven-bedroom home offers

Nikki Carchedi STONE HOUSE PROPERTIES, LLC

Tucked away on 10 private acres in the heart of Chatham, this stunning country estate offers over 5,700+ square feet of beautifully designed living space with the perfect balance of luxury, comfort, and privacy. Set far back from the road, the property welcomes you with peaceful surroundings, a scenic pond, and room to truly spread out and enjoy country living. Inside, the home features 6

Margaret Guerra Trevett Group LLC

Nancy Felcetto BROWN HARRIS STEVENS HUDSON

A Grand Dame in Old Chatham. Discover the joy in bringing back a classic. All the bones are solid. Five bedrooms in that rambling feel that makes farmhouses so lovable. The great room fireplace combines stone and real wood panels with views of the pond out the windows. A formal dining with wainscoting leads to a kitchen that leads out back. A second living room that could be it's own apartment.

Andrea Gabel Gabel Real Estate

In the desirable Spencertown hamlet, this ''top to bottom'' quality renovated Cape is move-in ready for summer enjoyment. Everything is new....roof, heating and AC, windows, doors, hardware, fully equipped kitchen with stainless appliances and granite countertops, flooring, lighting, bathrooms, fencing, washer and dryer and more. A fantastic location, close to Chatham, Hudson, The Berkshires and

Peter Newman Beach & Bartolo Realtors

Weeping Willow Pond, a rare and awe-inspiring 1700s estate set on 78 private acres in the heart of historic Austerlitz, is a masterful blend of historic authenticity and modern luxury. Thoughtfully restored and meticulously renovated, the property unfolds across rolling lawns, bucolic fields, and curated gardens with stone patios, fire pits, indigenous plantings, and a deep, clear swim

Nancy Felcetto Brown Harris Stevens HV LLC

Where History Breathes and Beauty Dwells: WHITE BRIDGE FARM c1775 Welcome to White Bridge Farm, an exquisite historic18th century estate restored and designed honoring and preserving the history with imagination and perfection. White Bridge Farm will take your breath away at every turn from the original restored iron main gate to magical stonewalls, pathways and gardens landscaped to intrigue all

Nancy Felcetto Brown Harris Stevens Hudson

Light-filled, charming 4 Bedroom/3.5 bath 1800s farmhouse with two ensuites -- including one on the first floor that can, alternatively, serve as a home office. Also on the first floor is a great room with high ceilings, a wood burning fireplace and French doors with access to the 24' x 24' deck. The home is set for entertaining with an easy flow from the eat-in kitchen, to the dining room, or

Jennifer Wall Anderson Agency

Welcome to Bezalel Gables, a Queen Anne Victorian 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 trees, ample lawns and a serene brook that

Tammy Molinski Coldwell Banker Advisor Realty

1945 brick charmer, a cozy and meticulously kept Chatham Village retreat that feels like home the moment you arrive. The heart of the house is a big, eat-in kitchen with a handy mudroom--the perfect spot to kick off your boots after coming in through the private back door.The sunny dining area opens right up to a large screened porch, perfect for sipping coffee while overlooking the dogwoods

Tracy Tassinari Gabel Real Estate

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

Welcome to 52 Church Street, a c.1900 home set on a generously-sized quarter acre lot in the Village of Philmont. Enter through a large mudroom flanked with windows. A stylish living room flows seamlessly to a large kitchen overlooking the yard. Numerous windows and a door leading to the backyard flood the kitchen space with light. A hall leads to a second kitchen, bedroom and full bath, perfect

MATTHEW CAREY Rouse + Co Real Estate

Sophistication meets rustic charm in this custom-built country retreat, perched in the hills of Spencertown on coveted Dugway Road. Set on 8.2 picturesque acres, this estate offers a rare blend of distant views, sunny meadows, and a private stream with waterfalls. The home's soul is found in its organic details: wide-plank flooring milled from the property's own timber and a soaring

Peter Newman Beach & Bartolo Realtors

2-Story/5-Apartment/9BR/6BA building PLUS 2BR/1BA Ranch home on about a half acre. Fully occupied, leases, both structures fully up to date and move-in condition. Tenants pay all utils. Landlord provides maintenance, snow/trash removal, water/sewer, off-street parking, fridge/stove each unit. 2 SBL lot numbers - properties not sold separately. Assessment/tax figures herein reflect total due for

Natalia de Amorim Preferred Country Properties

Tucked down a quiet country road, 2318 County Route 9 is the kind of place that feels like it's been waiting for you. Set on over five acres, this three bedroom, one bath cottage is thoughtfully designed from the inside out, every corner telling a story, every detail chosen with care.Sunlight pours through every window, framing the beauty of lush gardens and the natural world just beyond the

Shaina Marron Houlihan Lawrence Inc.

1800's Hamlet icon. 1st floor retail, 2nd floor 3BR Apt. 3000sqft total incl 50x25' open retail space w/ 3/4 bath (incl shower), 2 storage rms and walkout to rear yard. 2nd flr features residential apt w/50' great rm LR/DR/Kitchen, 3 BRS, full bath. Detached 1.5-car garage plus parking on site and across the street. 8 miles to Berkshires, 5 to Chatham Village and I90/Taconic Parkway. High

Natalia de Amorim Preferred Country Properties

Don't overlook this peaceful escape, tucked away on nearly five wooded acres with sweeping hilltop views--yet just minutes from Ghent and Chatham. This spacious contemporary home offers both privacy and a strong connection to the surrounding natural beauty. Set at the end of a long driveway on 4.8 wooded acres, coming home feels like a retreat into peace and stillness. The well-maintained home

Darcey Volans The Kinderhook Group, Inc.

Experience the perfect blend of 1900s farmhouse charm and contemporary comfort in the heart of Chatham. This thoughtfully updated farmhouse features an expansive open-concept kitchen and great room designed for seamless entertaining. Filled with natural light, the great room includes a wood burning stove and cozy window seat. Relax in the light-drenched enclosed front porch or enjoy dining on the

Beth Cozzolino Gabel Real Estate

Set in the heart of Old Chatham, this classic Colonial rests on an exceptional 101-acre landscape of rolling pasture, woodland, and wide-open country views. From its elevated vantage point, the home looks out over a 2.5-acre swimmable pond, open fields, and a stretch of Hudson Valley scenery that changes beautifully with the seasons. Flooded with natural light, the seven-bedroom home offers

Nikki Carchedi Stone House Properties, LLC

A rare opportunity to own a masterfully reimagined circa-1861 post-and-beam barn, transformedinto a one-of-a-kind luxury estate set on 89 pristine acres in the heart of Columbia County. Surrounded by sweeping pastoral views, open fields, and tranquil natural beauty, this exceptional property offers privacy, scale, and timeless craftsmanship. The residence spans approximately 6,000 square feet

Philip Feiner Country Life Real Estate, LLC

Experience the perfect blend of historic settlement and pastoral tranquility, enhanced by the abounding Valatie Kill on the property in the coveted hamlet of North Chatham. This is a rare opportunity to own a home in a nationally recognized Historic District, where 18th-century charm meets the modern desire for space and serenity. This very sweet 3200 square foot 4 bedroom 2.5 bathroom home comes

Annabel Taylor Four Seasons Sotheby's Int.

OPEN HOUSE this Saturday April 25 from 1 PM- 3PMIf you are looking for a move-in ready village farmhouse in Hudson Valley's Columbia County, you have found it! This gut-renovated home in charming and desirable Old Chatham is perfect for a weekend or full-time residence. There are 3 bedrooms, 2 1⁄2 retiled, replumbed and rebuilt bathrooms, a huge dressing room with custom built shelves and

Richard Byrne Four Seasons Sotheby's Int.

Charming 5-bedroom, 2-bath country-style home on a cozy lot, featuring an oversized two-car garage with a dedicated workshop area. Inside, enjoy a spacious family room, an inviting living room, and an eat-in kitchen--plenty of room for everyone. Recent upgrades include a durable metal roof, a new split system for efficient heating and cooling, on-demand hot water, and newer carpeting upstairs.

Leonard Brown Berkshire Hathaway HomeService