Chatham NY Real Estate & Homes for Sale

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Beds:
5
Baths:
5.00
Sq.Ft.:
4,307
Status:
Active
MLS#:
202622720
Type:
Single Family
Lot size:
21.09 Acres
Year built:
1886
Courtesy: Realhome Services & Solutions, Inc Neven Spralja 949-315-3946
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ADDITIONAL INFORMATION

Amazing Victorian style investment opportunity in Chatham, NY. Local attractions in area include Ooms Conservation area at Sutherland Pond or catching a musical at the Mac-Haydn Theatre. This Victorian Style home shows it was built in 1886. Total square footage is showing on tax records at 4,307 sq. ft. An amazing large lot of 918,680 sq. ft. An opportunity as such comes across once in a lifetime. Do not wait on this opportunity. AS-IS SALE property. The Buyer's due diligence needs to be conducted prior to bidding, as the high bidder will receive an AS-IS only contract.

Beds:
4
Baths:
5.00
Sq.Ft.:
3,691
Status:
Active
MLS#:
1029665
Type:
Single Family
Lot size:
30 Acres
Year built:
2005
A broker reciprocity listing Courtesy: Brown Harris Stevens HV LLC 518-828-0181
View additional info

ADDITIONAL INFORMATION

SUNSET MEADOW - A rare place where architecture and nature exist in perfect balance... As the the private drive gently climbs through the landscape, a sense of calm settles in. Perfectly sited on over 30 private acres of rolling lawns, flowering gardens, open meadows, and woodlands, this exceptional Kate Johns-designed country residence reveals itself, embracing commanding western Catskill Mountain views, spectacular sunsets, complete privacy, and nature's ever-changing beauty. An expansive front porch welcomes you before you even step inside, hinting at the gracious living spaces beyond, where soaring ceilings, walls of glass, wide-plank floors, and abundant natural light frame breathtaking vistas. Flooded with natural light, gracious living and dining spaces unfold beneath soaring ceilings, where a grand stone fireplace, timeless architectural details, and French doors opening to the stone patio create an atmosphere that is both elegant and inviting. Nearly every room enjoys breathtaking western Catskill Mountain views. The chef's kitchen is beautifully designed for both the serious and enthusiastic cook, with a generous center island, oversized walk-in pantry, Wolf range, and abundant storage. French doors open to one of the home's most memorable spaces—an expansive bluestone three-season porch overlooking lush gardens, the pool, patio and commanding western Catskill Mountain views. From morning coffee to sunset dinners, it's a space designed to be enjoyed in every season, creating an effortless connection between indoors and out. The private primary wing is a true sanctuary, offering a spacious bedroom, luxurious bath, exceptional walk-in closet, and an adjoining library or home office that easily serves as an additional bedroom. Upstairs, a sitting area connects two private en-suite guest bedrooms, each enjoying those sweeping Western views. In its own separate area, an additional spacious room offers remarkable flexibility as a studio, home office, library, or additional guest bedroom, allowing the home to live comfortably as either a four- or five-bedroom residence with 4½ baths. The finished lower level offers yet another wonderful surprise, designed for entertaining with a recreation room, bar, full bath, and abundant storage. A welcoming mudroom, laundry room, and attached two-car garage make everyday living as effortless as weekends in the country. Outside, lush perennial and wildflower gardens embrace the pool and spa, where monarch butterflies drift from bloom to bloom throughout the summer. A spring-fed swim pond, open meadows, and mature woodlands complete this extraordinary landscape, offering endless opportunities to relax, explore, and enjoy every season. ... A rare place where architecture and nature exist in perfect balance. Sunset Meadow.

Beds:
4
Baths:
5.00
Sq.Ft.:
3,691
Status:
Active
MLS#:
20264186
Type:
Single Family
Lot size:
31 Acres
Year built:
2005
A broker reciprocity listing Courtesy: Brown Harris Stevens Hudson 518-828-0181
View additional info

ADDITIONAL INFORMATION

SUNSET MEADOW - Where Architecture and Nature Exist in Perfect Balance As the private drive gently climbs through the landscape, a sense of calm settles in. Perfectly sited on over 30 private acres of rolling lawns, flowering gardens, open meadows, and woodlands, this exceptional Kate Johns-designed country residence reveals itself, embracing commanding western Catskill Mountain views, spectacular sunsets, complete privacy, and nature's ever-changing beauty. An expansive front porch welcomes you before you even step inside, hinting at the gracious living spaces beyond, where soaring ceilings, walls of glass, wide-plank floors, and abundant natural light frame breathtaking vistas. Flooded with natural light, gracious living and dining spaces unfold beneath soaring ceilings, where a grand stone fireplace, timeless architectural details, and French doors opening to the stone patio create an atmosphere that is both elegant and inviting. Nearly every room enjoys breathtaking western Catskill Mountain views. The chef's kitchen is beautifully designed for both the serious and enthusiastic cook, with a generous center island, oversized walk-in pantry, Wolf range, and abundant storage. French doors open to one of the home's most memorable spaces--an expansive bluestone three-season porch overlooking lush gardens, the pool, patio and commanding western Catskill Mountain views. From morning coffee to sunset dinners, it's a space designed to be enjoyed in every season, creating an effortless connection between indoors and out. The private primary wing is a true sanctuary, offering a spacious bedroom, luxurious bath, exceptional walk-in closet, and an adjoining library or home office that easily serves as an additional bedroom. Upstairs, a sitting area connects two private en-suite guest bedrooms, each enjoying those sweeping Western views. In its own separate area, an additional spacious room offers remarkable flexibility as a studio, home office, library, or additional guest bedroom, allowing the home to live comfortably as either a four- or five-bedroom residence with 4½ baths. The finished lower level offers yet another wonderful surprise, designed for entertaining with a recreation room, bar, full bath, and abundant storage. A welcoming mudroom, laundry room, and attached two-car garage, EV charging and solar make everyday living as effortless as weekends in the country. Outside, lush perennial and wildflower gardens embrace the pool and spa, where monarch butterflies drift from bloom to bloom throughout the summer. A spring-fed swim pond, open meadows, and mature woodlands complete this extraordinary landscape, offering endless opportunities to relax, explore, and enjoy every season.

Beds:
7
Baths:
2.00
Sq.Ft.:
1,214
Status:
Active
MLS#:
20263416
Type:
Single Family
Lot size:
0.46 Acres
Year built:
1932
A broker reciprocity listing Courtesy: Stone House Properties, LLC 413-232-4253
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ADDITIONAL INFORMATION

Set along scenic Route 203, this four-bedroom home enjoys easy access to the vibrant Village of Chatham, where beloved restaurants, local shops, farmers markets, and cultural attractions create one of Columbia County's most sought-after communities. Inside, the home offers a practical floor plan with comfortable living spaces and abundant potential for updates and personalization. Whether you're searching for a full-time residence, a weekend retreat, or an investment opportunity, this property provides an accessible entry point into the Chatham market. The manageable lot offers room for gardening, outdoor entertaining, or simply enjoying the surrounding landscape without the maintenance demands of a larger country estate. Ideally positioned between Hudson, Albany, and the Berkshires, this home places you in the center of everything the Hudson Valley has to offer while maintaining the charm and sense of community that make Chatham so desirable.

Beds:
3
Baths:
3.00
Sq.Ft.:
3,190
Status:
Active
MLS#:
20263385
Type:
Single Family
Lot size:
10 Acres
Year built:
1978
A broker reciprocity listing Courtesy: The Kinderhook Group, Inc. 518-392-8040
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ADDITIONAL INFORMATION

A truly magical property tucked away at the end of a quiet country road, yet just minutes from the Village of Chatham. Set amid 10 lush and exceptionally private acres, the centerpiece of this enchanting retreat is a light-filled barn conversion featuring a soaring stone fireplace, wide-plank floors, a lofted primary suite, and a separate guest level with living room, two bedrooms, a full bath, and laundry. The owners built and have lived here for 52 years, giving constant care and maintenance to the place they loved. The mature gardens are simply breathtaking, with vibrant perennial beds, specimen trees, and beautifully landscaped grounds creating a storybook setting throughout the property. A detached two-car garage includes a spacious apartment above, ideal for guests, extended family, or creative use. Completing the estate is a large workshop/studio offering endless possibilities. Enjoy the peace and seclusion of your own private hideaway while remaining just five minutes from Chatham's cafés, acclaimed restaurants, shops, and movie theater.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,005
Status:
Active
MLS#:
1012896
Type:
Single Family
Lot size:
9.5 Acres
Year built:
1935
A broker reciprocity listing Courtesy: Living Structures 518-622-0840
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ADDITIONAL INFORMATION

This 9.5-acre property in Chatham, NY offers exceptional potential, with multiple structures including a huge 2 story barn in excellent condition with a private pond. for swimming. A true diamond in the rough, the 2,005-square-foot main home features 3 bedrooms and 3 full bathrooms and has solid bones, though it does need some TLC. Dual brick fireplaces in the living room and reading nook, a formal dining room, and a 3-season porch add to its historic country charm. The property also includes a small unfinished house without a well or septic, ideal for use as a studio, guest house, or ADU. A huge barn with a loft and heated spaces offers excellent potential for a workshop, studio, or agricultural use, and it even includes an older walk-in refrigerator. The loft is ready for new owners to make it their own. A second, smaller barn also features a hayloft and has been used for storage. Although the vegetation is currently overgrown, the established fruit trees, perennial flower beds, and raised vegetable beds save years of effort. The reading nook , den and 3 season room would make a great at home office area (or in-law apartment) with it's own entrance). If you are looking for a special property to restore and make your own, this could be the one( the tax estimate on Zillow is incorrect and too high).

Beds:
3
Baths:
3.00
Sq.Ft.:
1,688
Status:
Active
MLS#:
1011916
Type:
Single Family
Lot size:
5 Acres
Year built:
1800
A broker reciprocity listing Courtesy: Houlihan Lawrence Inc. 845-876-4443
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ADDITIONAL INFORMATION

Recently renovated and thoughtfully updated, the streamside cottage and separate guest studio were once part of the historic Wigton Lester Farm, with origins dating back to the early 1800s. Nestled on 5 acres along one of the most picturesque roads in Old Chatham, the property is surrounded by open meadows, historic stone walls, and a gently winding stream that, over generations, has carved its way through ancient rock formations and into the surrounding woodland. Inside the cottage, the original beamed ceilings have been carefully preserved and whitewashed, creating a bright and welcoming backdrop for the main level. The wood mantel surrounding the former fireplace is believed to be original to the structure, adding a tangible connection to the home's rich past. Antique wide-plank pine floors and distinctive 9-over-6 asymmetrical windows lend authentic colonial character. Enter through the mudroom and step into the kitchen that has been tastefully reimagined for today's home chef, blending modern convenience with timeless charm. A beautifully renovated full bath featuring a soaking tub completes the first floor. On the walk-out lower level, the spacious bedroom welcomes the morning sun and offers a peaceful retreat. A private full bath with a generous shower, large vanity, ample closet space, and additional storage complete this part of the home. The upper floor provides flexible living space, ideal for a home office, reading nook, studio, guest accommodations, or additional sleeping quarters. Overlooking the gently flowing stream, the sun deck provides a perfect vantage point to listen to the songbirds nestled in the property's mature hardwoods and evergreens, which blanket the landscape with natural beauty and privacy. The Studio is a striking antique structure offering a variety of uses. Soaring wood ceilings enhance the expansive main living area, where a modern fireplace serves as a focal point and oversized windows flood the space with natural light. The kitchen is thoughtfully designed and highly efficient, offering the functionality and style. A stone tiled shower completes the first floor bathroom. The second-floor bedroom enjoys western exposure and opens onto a private deck overlooking the grounds, offering a front-row seat to spectacular sunset views. Private and serene, this remarkable property captivates on every level, offering a rare opportunity to own something truly special. Become the next steward of its rich history while shaping its future and creating a legacy of your own.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,005
Status:
Active
MLS#:
20263202
Type:
Single Family
Lot size:
9.5 Acres
Year built:
1935
A broker reciprocity listing Courtesy: Living Structures 518-622-0840
View additional info

ADDITIONAL INFORMATION

Located only 30 minutes from the Hudson Amtrak Train Station this 9.5-acre property in Chatham, NY offers exceptional potential one of which could be an organic farm. With multiple structures there are endless possibilities. An amazing 2 story huge barn would work for an artist/actor or musician studio and wouild also work for horses. There is a private pond for swimming, kayajing and fishing. The tax estimate on Zillow is incorrect and should read 6,195 dollars, The 2,005-square-foot main home features 3 bedrooms and 3 full bathrooms and has solid bones, though it does need some TLC. There are dual brick fireplaces in the living room and reading nook, a formal dining room, and a 3-season porch which add to its historic country charm. The property also includes a small unfinished house without a well or septic, ideal for use as an ADU, additional studio, guest house, or artist studio. A smaller barn also features a hayloft and has been used for storage. Although the vegetation is currently overgrown, the established fruit trees, perennial flower beds, and raised vegetable beds save years of effort. The reading nook , den and 3 season room would make a great at home office area (or in-law apartment) with it's own entrance. Located near the Hawthorn Valley School and the Mac Hayden Summerstock Theater this is a special property to restore and make your own.

Beds:
4
Baths:
4.00
Sq.Ft.:
4,500
Status:
Active
MLS#:
20262908
Type:
Single Family
Lot size:
62 Acres
Year built:
2006
A broker reciprocity listing Courtesy: Gabel Real Estate 518-392-4975
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ADDITIONAL INFORMATION

Camp Dugway A home that evokes the great camps of the Adirondacks within 2 hours of Manhattan. Cross the bridge over a babbling brook to a setting straight out of a Cooper novel. Three cascading waterfalls frame the view. The pond sits just off the bluestone patio. Inside a blend of craftsman style and great camp ambiance in every room. The fieldstone in the fireplace came from the land as did much of the wood used in the flooring and panels. The rooms are of a grand scale, with window placement and size designed to compliment nature and splash light. The living room is anchored by the fireplace, the dining flows nicely from the kitchen. The kitchen is made to prepare a feast with room for as many cooks as necessary. The first floor main bedroom opens to the outside patio with a deep tub for long soaks of contemplation. Upstairs three more bedrooms and the game room, full of light and mischief. Downstairs its movie time in the theater with cinema seating and lighting. A home gym for weekend workouts. 62 acres of buffer to the outside world and plenty of places to hike and explore. To quote Cooper, ''for though the quiet of deep solitude reigned in that vast and nearly boundless forest, nature was speaking with her thousand tongues in the eloquent language of night''. Features include a babbling brook, private pond, fieldstone fireplace, complete privacy, home theater, gourmet kitchen

Beds:
5
Baths:
2.00
Sq.Ft.:
1,872
Status:
Active
MLS#:
1006015
Type:
Single Family
Lot size:
0.28 Acres
Year built:
1900
A broker reciprocity listing Courtesy: Rouse + Co Real Estate 845-702-4379
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ADDITIONAL INFORMATION

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 for an in-law suite or separate apartment. Upstairs four large bedrooms with generous closet spaces share a full bath. Tasteful wallpaper and decorative finishes combine with hardwood floors to provide charm throughout. Outside, an expansive deck runs the length of the exterior, giving way to a large fenced-in yard. A new hot tub and sauna offer moments of respite while the gas firepit ensures guests will be entertained well into the evening. A separate garage offers off-street parking and additional space suitable for a workshop and / or storage. Numerous updates include — but are not limited to — new appliances in each kitchen, a mini-split heating & cooling system as well as painted interiors & exteriors. Ideally located within walking distance to Philmont village amenities and High Falls Conservation Area, this home is perfectly positioned to enjoy the best of the Hudson Valley. Hudson and Amtrak are just 15 minutes away, with New York City approximately 2.5 hours by car.

Beds:
6
Baths:
5.00
Sq.Ft.:
5,738
Status:
Active
MLS#:
202617663
Type:
Single Family
Lot size:
10.07 Acres
Year built:
1989
Courtesy: Trevett Group LLC Thomas Trevett 518-885-3941
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ADDITIONAL INFORMATION

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 spacious bedrooms and 5 bathrooms, including an ideal in-law suite or private apartment setup for extended family, guests, or potential additional living space. The heart of the home is the incredible chef's kitchen--thoughtfully designed with generous work space, high-end finishes, and the kind of layout any chef or aspiring cook would absolutely love. Step outside to enjoy the wrap around deck overlooking the built-in saltwater pool and serene grounds, creating the perfect setting for entertaining or simply relaxing into total privacy. A 3-car garage plus an additional garage beneath the residence provide plenty of room for tractor, hobbies, and storage. This one-of-a-kind Chatham retreat combines elegant country living with modern convenience, all just a short drive to the charming villages, restaurants, and culture the Hudson Valley is known for.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,922
Status:
Active
MLS#:
20262537
Type:
Single Family
Lot size:
7.41 Acres
Year built:
1995
A broker reciprocity listing Courtesy: The Kinderhook Group, Inc. 518-751-4444
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ADDITIONAL INFORMATION

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 stainless steel appliances, subway tile backsplash and separate island. The home features a central hallway with an elegant living room and working fireplace, dining room, home office/den, washer/dryer units on both the first floor and basement, central AC and full-house generator. In addition, there is a second driveway entrance with RV/EV electric, which leads to a park-like meadow with walking trails. Off of the great room, walk onto the large screened-in porch which overlooks the lush garden grounds with 2 flowing ponds joined by a waterfall. Upstairs features 3 large bedrooms (originally 4) with ensuite baths and a large terrace leading to the outdoors. Spencertown is accessible to Chatham, The Berkshires, Hudson and Albany and is in the perfect location to take advantage of all that Columbia County has to offer!

Beds:
3
Baths:
2.00
Sq.Ft.:
2,908
Status:
Active
MLS#:
998937
Type:
Single Family
Lot size:
20.03 Acres
Year built:
1985
A broker reciprocity listing Courtesy: Houlihan Lawrence, Inc 518-822-0300
View additional info

ADDITIONAL INFORMATION

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 with remarkable artistry, craftsmanship, and thoughtfully integrated modern systems. Triple-paned Austrian-engineered windows and sliding doors flood the interiors with natural light while providing outstanding insulation and quiet, and looking out onto your own private field. Major upgrades include new James Hardie concrete siding, a new roof, updated electrical and plumbing systems, new water pump infrastructure, all new split-unit heating and cooling systems, and solar panels, creating a home that is both highly energy efficient and deeply considered. The main living spaces blend warmth, texture, and refined modern design. Wide plank white oak flooring runs throughout the upper levels, while the living room centers around a dramatic floor-to-ceiling fluted marble wood-burning fireplace. The adjacent dining area includes a built-in entertaining station with an ice maker and wine fridge, ideal for hosting gatherings large and small. Walls of glass open directly onto a generous new cedar deck designed for seamless indoor-outdoor living. Complete with a hot tub, outdoor shower, grilling area, and sunny lounging spaces, the private deck overlooks rolling pastoral fields, creating a private outdoor setting equally suited for entertaining, quiet mornings, or evenings spent soaking under the stars. The kitchen pairs clean contemporary lines with stone countertops, custom cabinetry, a walk-in pantry, handcrafted emerald green Zellige tile, and Fisher & Paykel appliances. Bathrooms continue the same elevated approach, featuring marble finishes, Zellige tilework, and spa-like details including heated floors and a heated towel rack. The primary en suite bedroom is a true retreat, complete with a lofted living space overlooking the main open floor plan living area, a double walk-in closet, and tranquil woodland outlooks. The walk-out on grade lower level offers substantial additional living space ready for customization, with architectural plans available for future completion. Anchored by a wood-burning stove, the space could easily accommodate additional bedrooms alongside media, guest, spa, or studio space. Outside, mature trees and wooded landscape, and the year-round creek create a peaceful and immersive setting. A garage with space for three vehicles adds practicality to the property’s thoughtful design. Only five minutes from the village of Chatham, the property offers rare privacy and natural beauty without sacrificing access to the region’s most beloved towns, restaurants, and cultural destinations. Hudson’s celebrated Warren Street, with its restaurants, galleries, boutiques, and Amtrak station, is under twenty minutes away, while the Berkshires’ cultural and outdoor destinations, including Great Barrington, Lenox, and Tanglewood, are all within easy reach. New York City is reachable in just over two hours by car or train. Chicory Hill House delivers sophisticated country living with privacy, design, and a high level of finish at every turn.

Beds:
3
Baths:
1.00
Sq.Ft.:
1,400
Status:
Active
MLS#:
999209
Type:
Single Family
Lot size:
1.71 Acres
Year built:
1958
A broker reciprocity listing Courtesy: Houlihan Lawrence, Inc 518-822-0300
View additional info

ADDITIONAL INFORMATION

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 glass. A stone fireplace anchors the living room with warmth and character, while French doors open onto a gorgeous fieldstone sitting area, the perfect place to linger on a slow afternoon. The generous eat-in kitchen, outfitted with butcher block counters and new appliances, flows effortlessly to a back patio made for easy entertaining and long summer evenings. A one car garage with a connecting mudroom adds practical charm, offering extra storage and pantry space for the way real life unfolds. From the moment you step inside, something shifts. The pace slows. The world quiets. These are the kinds of rooms that invite you to sit down and stay awhile. Follow the stone path from the house and you'll discover a beautifully maintained and restored barn, currently thriving as an artist's workshop, with endless possibilities waiting to be written by its next chapter. The current owner has lovingly done the heavy lifting: new roof, new retaining wall, fresh hardscaping and landscaping, new fencing, fresh paint and an upgraded kitchen. All that's left is for you to arrive. Just minutes from Chatham Berry Farm, the Crandell Theatre, Bimi's, Kinderhook, Hudson, and Great Barrington, this is country living with everything you love close at hand

Beds:
3
Baths:
2.00
Sq.Ft.:
2,908
Status:
Active
MLS#:
20262346
Type:
Single Family
Lot size:
20.03 Acres
Year built:
1985
A broker reciprocity listing Courtesy: Houlihan Lawrence Inc. 518-822-0300
View additional info

ADDITIONAL INFORMATION

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 with remarkable artistry, craftsmanship, and thoughtfully integrated modern systems. Triple-paned Austrian-engineered windows and sliding doors flood the interiors with natural light while providing outstanding insulation and quiet, and looking out onto your own private field. Major upgrades include new James Hardie concrete siding, a new roof, updated electrical and plumbing systems, new water pump infrastructure, all new split-unit heating and cooling systems, and solar panels, creating a home that is both highly energy efficient and deeply considered. The main living spaces blend warmth, texture, and refined modern design. Wide plank white oak flooring runs throughout the upper levels, while the living room centers around a dramatic floor-to-ceiling fluted marble wood-burning fireplace. The adjacent dining area includes a built-in entertaining station with an ice maker and wine fridge, ideal for hosting gatherings large and small. Walls of glass open directly onto a generous new cedar deck designed for seamless indoor-outdoor living. Complete with a hot tub, outdoor shower, grilling area, and sunny lounging spaces, the private deck overlooks rolling pastoral fields, creating a private outdoor setting equally suited for entertaining, quiet mornings, or evenings spent soaking under the stars. The kitchen pairs clean contemporary lines with stone countertops, custom cabinetry, a walk-in pantry, handcrafted emerald green Zellige tile, and Fisher & Paykel appliances. Bathrooms continue the same elevated approach, featuring marble finishes, Zellige tilework, and spa-like details including heated floors and a heated towel rack. The primary en suite bedroom is a true retreat, complete with a lofted living space overlooking the main open floor plan living area, a double walk-in closet, and tranquil woodland outlooks. The walk-out on grade lower level offers substantial additional living space ready for customization, with architectural plans available for future completion. Anchored by a wood-burning stove, the space could easily accommodate additional bedrooms alongside media, guest, spa, or studio space. Outside, mature trees and wooded landscape, and the year-round creek create a peaceful and immersive setting. A garage with space for three vehicles adds practicality to the property's thoughtful design. Only five minutes from the village of Chatham, the property offers rare privacy and natural beauty without sacrificing access to the region's most beloved towns, restaurants, and cultural destinations. Hudson's celebrated Warren Street, with its restaurants, galleries, boutiques, and Amtrak station, is under twenty minutes away, while the Berkshires' cultural and outdoor destinations, including Great Barrington, Lenox, and Tanglewood, are all within easy reach. New York City is reachable in just over two hours by car or train. Chicory Hill House delivers sophisticated country living with privacy, design, and a high level of finish at every turn.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,908
Status:
Active
MLS#:
202617064
Type:
Single Family
Lot size:
20.03 Acres
Year built:
1985
Courtesy: Houlihan Lawrence Inc Anthony D'Argenzio 518-821-0826
View additional info

ADDITIONAL INFORMATION

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 with remarkable craftsmanship and modern systems. The home features wide plank white oak floors, a floor-to-ceiling fluted marble wood-burning fireplace, stone countertops, handcrafted Zellige tile, and spa-like baths. An expansive cedar deck, hot tub, outdoor shower, solar panels, and a flexible lower level with a wood-burning stove and room for additional bedrooms complete the property. Just five minutes to Chatham, under twenty to Hudson's Warren Street, and a little over two hours to New York City.

Beds:
3
Baths:
3.00
Sq.Ft.:
3,100
Status:
Active
MLS#:
995720
Type:
Single Family
Lot size:
14.08 Acres
Year built:
1981
A broker reciprocity listing Courtesy: Corcoran Country Living 845-338-5832
View additional info

ADDITIONAL INFORMATION

Situated at the top of a private lane just outside the hamlet of Spencertown, sits a 14-acre sanctuary offering breathtaking views of the surrounding landscape with the majestic Catskill peaks in the distance. Wildflower meadows and lush gardens provide three seasons of color while an ecologically designed swimming pond, frame the home, complete with stone patios and porches - all to take in the beautiful Catskills. Stepping through the front door of a wide covered front porch, you'll find an open plan kitchen, dining & living room - the heart of the home, made cozy in winter by an efficient wood stove. The first floor also includes a mud room, office, powder room, laundry room and den. However, it is the 600 sq ft ''Great Room'', with windows on 3 sides that immerse you in the ever-shifting displays of nature and the Catskill range. Upstairs you'll find 3 generous sized bedrooms and 2 full baths including a primary suite with walk-in closet room. The pond, designed by famed UK pool master Anthony Archer-Wills, provides an unparalleled natural swimming experience, set among a chorus of frogs and dragonfly's dancing across the water. A variety of colorful waterlilies and other pond plantings keep the water fresh and inviting. Renovated throughout in 2024-2025, this solar powered home offers you privacy, comfort and jaw dropping sunsets. Conveniently located 10 minutes from Chatham, 30 minutes to the train in Hudson, 40 minutes to the Albany Airport and 25 minutes to Great Barrington & all the culture and fun that our neighboring Berkshires offer. Broker Owned.

Beds:
5
Baths:
4.00
Sq.Ft.:
2,982
Status:
Active
MLS#:
20262134
Type:
Single Family
Lot size:
0.6 Acres
Year built:
1900
A broker reciprocity listing Courtesy: Gabel Real Estate 518-392-4975
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ADDITIONAL INFORMATION

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 private, screened back porch constructed from spruce trees resourced from the property. Entering the new addition, you'll find a spacious mudroom with 1/2 bath just off the kitchen. The original part of the first level includes the kitchen/ great room, a full bath, dining room and office or guest space. On the second floor, a sunny reading nook, 3 more bedrooms and a full bath. The home's crowning jewel is a stunning new addition, offering a private spa-like retreat with a workout room, built-in sauna and shower on the main level and a versatile two room, one-bath suite tucked privately upstairs. Deep and spacious front lawn and large, fenced in rear yard are bordered by flowering magnolia, azaleas, hydrangeas, fragrant rose bushes, peonies and sweet scented lilacs. An added feature - the garage with a separate apartment with galley kitchen, sitting room and bedroom. Conveniently located just steps to the village restaurants, library and shops.

Beds:
3
Baths:
3.00
Sq.Ft.:
3,100
Status:
Active
MLS#:
202616466
Type:
Single Family
Lot size:
14.08 Acres
Year built:
1981
Courtesy: Corcoran Country Living Michael Stasi 732-241-1723
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ADDITIONAL INFORMATION

Situated at the top of a private lane just outside the hamlet of Spencertown, sits a 14-acre sanctuary offering breathtaking views of the surrounding landscape with the majestic Catskill peaks in the distance. Wildflower meadows and lush gardens provide three seasons of color while an ecologically designed swimming pond, frame the home, complete with stone patios and porches - all to take in the beautiful Catskills. Stepping through the front door of a wide covered front porch, you'll find an open plan kitchen, dining & living room - the heart of the home, made cozy in winter by an efficient wood stove. The first floor also includes a mud room, office, powder room, laundry room and den. However, it is the 600 sq ft ''Great Room'', with windows on 3 sides that immerse you in the ever-shifting displays of nature and the Catskill range. Upstairs you'll find 3 generous sized bedrooms and 2 full baths including a primary suite with walk-in closet room. The pond, designed by famed UK pool master Anthony Archer-Wills, provides an unparalleled natural swimming experience, set among a chorus of frogs and dragonfly's dancing across the water. A variety of colorful waterlilies and other pond plantings keep to keep the water fresh and inviting. Renovated throughout in 2024-2025, this solar powered home offers you privacy, comfort and jaw dropping sunsets. Conveniently located 10 minutes from Chatham, 30 minutes to the train in Hudson, 40 minutes to the Albany Airport and 25 minutes to Great Barrington & all the culture and fun that our neighboring Berkshires offer. Broker Owned.

Beds:
3
Baths:
3.00
Sq.Ft.:
3,100
Status:
Active
MLS#:
20262099
Type:
Single Family
Lot size:
14.08 Acres
Year built:
1981
A broker reciprocity listing Courtesy: Corcoran Country Living 518-660-7120
View additional info

ADDITIONAL INFORMATION

Situated at the top of a private lane just outside the hamlet of Spencertown, sits a 14-acre sanctuary offering breathtaking views of the surrounding landscape with the majestic Catskill peaks in the distance. Wildflower meadows and lush gardens provide three seasons of color while an ecologically designed swimming pond, frame the home, complete with stone patios and porches - all to take in the beautiful Catskills. Stepping through the front door of a wide covered front porch, you'll find an open plan kitchen, dining & living room - the heart of the home, made cozy in winter by an efficient wood stove. The first floor also includes a mud room, office, powder room, laundry room and den. However, it is the 600 sq ft ''Great Room'', with windows on 3 sides that immerse you in the ever-shifting displays of nature and the Catskill range. Upstairs you'll find 3 generous sized bedrooms and 2 full baths including a primary suite with walk-in closet room. The pond, designed by famed UK pool master Anthony Archer-Wills, provides an unparalleled natural swimming experience, set among a chorus of frogs and dragonfly's dancing across the water. A variety of colorful waterlilies and other pond plantings keep the water fresh and inviting. Renovated throughout in 2024-2025, this solar powered home offers you privacy, comfort and jaw dropping sunsets. Conveniently located 10 minutes from Chatham, 30 minutes to the train in Hudson, 40 minutes to the Albany Airport and 25 minutes to Great Barrington & all the culture and fun that our neighboring Berkshires offer. Broker Owned.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,300
Status:
Active
MLS#:
202613968
Type:
Single Family
Lot size:
0.23 Acres
Year built:
1930
Courtesy: Preferred Country Properties Natalia De Amorim 518-692-6006
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ADDITIONAL INFORMATION

Lucrative income property in the center of a New England hamlet's business district. Minutes to Taconic State Parkway/ I90/ Berkshire Spur, 15 minutes to Lenox/ Tanglewood, 30 minutes Albany/ Capital Region. 3 buildings fully occupied incl 2BR/1.5BATH center hall 1930's home w/LG foyer staircase flanked by LG common RMS incl LR w/wood fireplace opposite spacious DR. Wood flrs throughout and leased for 2,300 dollars/MTH til 8/31/26. 2nd bldg is East Chatham Wine & Spirits store w/half-bath currently 1541 dollars/MTH-to-mth. 3rd bldg currently a funeral parlor/office w/half-bath 850 dollars/MTH til 4/30/26 All photos pre-occupancy. All units occupied. No interior liquor store photos. Tenants must approve all showings and provide access. 48HR notice minimum.

Beds:
2
Baths:
2.00
Sq.Ft.:
998
Status:
Active
MLS#:
20255450
Type:
Mobile Home
Year built:
2006
A broker reciprocity listing Courtesy: Trevett Group LLC 518-885-3941
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ADDITIONAL INFORMATION

Charming 2-Bed, 2-Bath Single-Wide Mobile Home in Sought-After Chatham - No Age Restrictions! Don't miss this rare opportunity to own a beautifully maintained 2-bedroom, 2-full-bath single-wide mobile home in the highly desirable area of Chatham—and best of all, it's located in a non-55+ community! This home offers a bright, open-concept layout with a spacious living area, a functional kitchen with plenty of storage, and two full bathrooms, providing added comfort and flexibility—perfect for families, guests, or roommates. Both bedrooms are generously sized, with ample closet space and natural light. Outside, enjoy your own private yard—great for gardening, relaxing, or entertaining. The home is set on a quiet street, close to local shopping, dining, schools, lakes, and nature trails. With low lot rent and manageable utility expense, this home offers an affordable way to enjoy everything Chatham has to offer. 🏡 Whether you're a first-time homebuyer, downsizing, or looking for a Cape Cod like getaway, this home checks all the boxes. Home is sold ''AS IS'' 📞 Schedule your showing today—opportunities like this in Chatham don't come around often!

Beds:
3
Baths:
4.00
Sq.Ft.:
2,050
Status:
Active
MLS#:
157041
Type:
Single Family
Lot size:
7 Acres
Year built:
2006
Courtesy: Corcoran Country Living - Hud 518-660-7120
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ADDITIONAL INFORMATION

Opportunity at your fingertips! A Chatham farm property with endless possibilities. Anchoring this seven-acre parcel is a three bedroom, three and one-half bath 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 Parkway. Entering the long stone drive to the home and barn, the property offers a natural sense of privacy. The existing home was expanded in 2006 and includes three-bedrooms all with ensuite baths. The original home is wood paneled and connected to the open floor plan of the kitchen, living room and dining room addition. From these interior spaces and from the exterior decks, one is immersed with views of the property and spring-fed pond. Further, the property is surrounded by and abuts the 65 acre Borden Pond conservation land - a hiker's paradise.The original barn with multiple stalls has been expanded over the years to include equipment storage and electric. The incredible second floor loft of the barn adds to the studio, farming and contracting potential. Included as part of the barn structure is a roughly 1000 SF, wood paneled one bedroom cottage - ready to provide additional income or use for family or friends. Upgrades within the last year include a number of kitchen appliances, plumbing fixtures and door hardware. Come see for yourself the opportunity this property offers steps away from Chatham downtown, but within a short drive to Hudson, Kinderhook and the Berkshires.

Beds:
4
Baths:
3.00
Sq.Ft.:
1,850
Status:
Active
MLS#:
156969
Type:
Single Family
Lot size:
0.39 Acres
Year built:
1820
Courtesy: Berkshire Hathaway HomeService 518-687-2222
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ADDITIONAL INFORMATION

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 ensuite with hardwood floors and 1.5 baths on first floor. Laundry hookups upstairs with 3 other bedrooms with new carpeting and a full bath w/ceramic tile Oversized closets, one walk in. Office area upstairs,2 car garage. Right on route 295 close to everything, Berkshires for culture and skiing, Hudson, Albany, TSP, I-90.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,375
Status:
Active
MLS#:
156913
Type:
Single Family
Lot size:
0.64 Acres
Year built:
1958
Courtesy: Beach & Bartolo Realtors 518-392-2700
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ADDITIONAL INFORMATION

This updated mid-century ranch offers significant improvements, including brand new wood floors, Marmoleum, and tile. Enjoy modern comfort with a new wood-burning insert, heat pump cooling/heating system, heat pump water heater, and two additional ductless split units. The home also features new appliances, a renovated basement, enhanced attic insulation, a backyard fence, a fabulous sunroom, and a new Trex deck. A one-car garage completes the property.Conveniently located near the Village of Chatham, you'll be surrounded by nature while enjoying easy access to Chatham's coffee shops, movie theater, and restaurants. It's also near the new Shaker Museum and just across the road is Borden's Trail. The location is ideal: 2.5 hours from NYC, 20 minutes to Hudson, and close to the Taconic Parkway and the Berkshires.**OPEN HOUSE Saturday May 3rd 11AM-1PM and Sunday May 4th 12pm-2pm**Agent Owned**

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Andrea D. Conner, License 10311208085, Xome Inc., License 10991227159, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Suite 100, Lewisville, Texas 75067

© 2026 Greater Capital Association of REALTORS (CRMLSNY). All rights reserved. The data relating to real estate for sale on this website have been downloaded from CRMLS. The IDX logo indicates listings of other real estate firms that are identified in the detailed listing information. Information herein is deemed reliable but not guaranteed, representations are approximate, individual verification's recommended. Per New York legal requirement, click here for the Standard Operating Procedures.

Andrea D. Conner, License 10311208085, Xome Inc., License 10991227159, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Suite 100, Lewisville, Texas 75067

Listings courtesy of One Key MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of 11/13/2024. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS. Per New York legal requirement, click here for the Standard Operating Procedures. Copyright 2026, OneKey MLS, Inc. All Rights Reserved.
Andrea D. Conner, License 10311208085, Xome Inc., License 10991227159, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Suite 100, Lewisville, Texas 75067


The data relating to real estate on this website comes in part from the IDX of the Hudson Valley Catskill Region MLS. Real estate listings held by brokerage firms other than Xome are marked with IDX logo and the detailed information about them includes the name of the listing broker. Per New York legal requirement, click here for the Standard Operating Procedures. Copyright 2026 by the Hudson Valley Catskill Region MLS and Ulster County Board of Realtors, Inc. All Rights Reserved.

Andrea D. Conner, License 10311208085, Xome Inc., License 10991227159, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Suite 100, Lewisville, Texas 75067


The data relating to real estate for sale on this web site comes in part from the Columbia Greene Northern Dutchess MLS. Real estate listings held by brokerage firms other than Xome include the name of the listing broker. Information is deemed reliable but is not guaranteed accurate by the MLS. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Per New York legal requirement, click here for the Standard Operating Procedures. Copyright 2026 Columbia Greene Northern Dutchess MLS. All rights reserved.



Chatham Real Estate

Chatham is located in New York. Chatham, New York has a population of 4,079. Chatham is more family-centric than the surrounding county with 24.65% of the households containing married families with children. The county average for households married with children is 22.64%.

The median household income in Chatham, New York is $92,794. The median household income for the surrounding county is $73,065 compared to the national median of $69,021. The median age of people living in Chatham is 49.9 years.

Chatham Weather

The average high temperature in July is 82.7 degrees, with an average low temperature in January of 13.8 degrees. The average rainfall is approximately 42.9 inches per year, with 49.7 inches of snow per year.

Chatham Map

Chatham Real Estate Market Conditions

  • Median sales price

    $519,500
    11.9%
    change since last quarter
  • # Active listings

    59
    30-day change

Chatham Schools and Demographics

Education near Chatham, NY

City County
High School Graduates 96.78 91.22
College Degree - 2 year 10.65 12.48
College Degree - 4 year 47.43 34.88
Graduate Degree 16.73 11.92
Expenditures per Student 33,117 33,117
Students per Teacher 10.2 10.2

Elementary Schools near Chatham, NY

Grades Students P/T Ratio ZIP
Ichabod Crane Elementary School 03 - 05 265 15.3 12184
Ichabod Crane Primary School KG - 03 560 13.9 12184
Mary E Dardess Elementary School PK - 05 483 13 12037
Taconic Hills Elementary School PK - 06 770 12.6 12521
Walter B Howard Elementary School KG - 06 185 9.7 12125

Middle Schools near Chatham, NY

Grades Students P/T Ratio ZIP
Chatham Middle School 06 - 08 258 11.7 12037
Ichabod Crane Middle School 06 - 08 410 11.2 12184

High Schools near Chatham, NY

Grades Students P/T Ratio ZIP
Chatham High School 09 - 12 394 12.1 12037
Ichabod Crane Senior High School 09 - 12 648 14.8 12184
New Lebanon Junior-Senior High School 07 - 12 217 8.3 12125
Taconic Hillsjunior/Senior High School 07 - 12 657 12.4 12521

Demographics near Chatham, NY

City County
Neighborhood Type Small town
Population 4,079 61,587
Population Density 77 97
Median Age 49.9 48.9
People per Household 2.4 2.4
Median Household Income 92,794 73,065
Average Income per Capita 54,134 42,900

Real estate near Chatham