Courtesy: Beach & Bartolo Realtors
518-392-2700
A rare opportunity in the heart of the coveted hamlet of Spencertown, this 1790's completely renovated antique gem, center hall colonial AND contemporary guest house are perfection and ready to greet its next owner. One of the earliest homes in the area, this gracious center hall colonial has been brought into the 21st century while maintaining its 18th century character. The gorgeous wide board flooring, moldings and banister a.re original . The home was updated and an addition added in 2007 to create this 2500sq ft home set on 2 magnificently landscaped semi private acres. In addition, across the pond is the completely self contained guest house. The sun filled majestic home has 4 bedrooms, 2 1/2 baths. and a garage/workshop. Upon entering, the foyer, you are transported back in time, Wonder around to view the living room dining room, custom kitchen and dining area, mud room, 1/2 bath and a laundry room. Cozy up to the living room's wood burning fireplace or step out onto the veranda to enjoy the properties beauty. Beyond the pond sits the cathedral ceiling contemporary, geothermal heated and cooled guest house with a grand, sweeping deck, walls of glass, 2 bedrooms, a large living room and dining area, full bath and laundry facility. This Spencertown ''compound'' is the perfect blend for entertaining friends, extended family, a work at home retreat or a fantastic rental. For full time living or weekends, the home's location is ideal for Chatham, Hudson, The Berkshires Hawthorn Valley Market, The Berry Farm, great eateries, a quick Albany commute, and easy access to the Taconic.
Courtesy: Brown Harris Stevens HV LLC
854-871-2700
Willow Pond Retreat – 12 Acres of Serenity & Soul Welcome to Willow Pond Retreat, a 12-acre country haven where beauty and function live in perfect harmony. Surrounded by mature gardens, sweeping willows, and a tranquil pond, this property offers privacy, warmth, and endless possibility. The main residence features multiple fireplaces and a light-filled kitchen overlooking nature’s ever-changing views. Outside, a newly lined navy pool is framed by lush, established gardens — an idyllic setting for quiet mornings or summer gatherings. A separate ADU apartment provides flexibility for guests or extended family, while the spacious workshop/studio invites creativity and craft. Meandering garden paths, blooming daffodils, and even a charming chicken coop complete the picture of country living at its most soulful. A new roof, new boiler system...rest is your desired imagination. Private, romantic, and deeply functional, Willow Pond Retreat is more than a home — it’s a lifestyle. A place where life is meant to be lived, not merely observed.
Courtesy: Crystal Coleman Realty, LLC
518-229-4539
Discover this move-in ready village home set on over an acre at the end of a quiet dead-end road. Just an easy walk to shops and amenities in the heart of Chatham. The freshly painted interior showcases beautiful hardwood floors throughout, a spacious eat in kitchen, family room, and a large living room with a cozy fireplace. The home offers two generously sized bedrooms with room to easily create a third, plenty of closets, and up-to-date mechanicals including a new roof and central air. All appliances are included, making move-in even easier. It also features convenient first-floor washer and dryer hookups making laundry days a breeze, and a large basement perfect for storage. Enjoy outdoor living on a large deck, relax by the pool in the expansive yard, and take advantage of the over-sized garage with an automatic opener- an ideal blend of convenience and comfort. Just over an hour from Saratoga, thirty five minutes from June farm and just minutes away from Art Omi.
Courtesy: Trevett Group LLC
518-885-3941
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. 📞 Schedule your showing today—opportunities like this in Chatham don't come around often!
Courtesy: Gabel Real Estate
518-392-4975
Simple Aesthetic Modern lines, simple space made warm with natural materials. The kitchen, dining and living flow easily and bring in the outside thru smart use of windows, sliding glass doors and the deck. Two perfect bedrooms, a bath. Easy to live in, easy to feel right at home.
Courtesy: Beach & Bartolo Realtors
518-392-2700
A Rare Opportunity in Chatham For the first time in 37 years, this unique multi-family home is on the market. Situated on a quiet street, it's just a short stroll from Chatham's vibrant main street, offering an unbeatable combination of lifestyle and investment. This property is a dream for a first-time home buyer. Live in the spacious 2,100 square foot main residence, which features four bedrooms and two bathrooms, and let the rental income from the separate apartment help cover your mortgage. The one-bedroom apartment has its own entrance and until recently was rented for 1,050 per month, with the tenant covering their own utilities. That immediate, substantial income makes homeownership here more affordable than ever. The main home has a welcoming feel with gleaming hardwood floors and a recently updated kitchen with all-new appliances and cabinetry. You'll appreciate the convenience of municipal water and sewer services, and the heating is provided by an efficient oil hot water system with 200-amp electrical service. Outdoor living is easy with a classic front porch and a private yard space. An added plus is the oversized two-car garage with extra storage, offering even more potential for income or personal use. Another Plus to this home, is the additional unfinished space located above the rental unit. If finished, it would add an additional two bedrooms to the rental unit, and substantial additional income. This home is priced to sell and offers unbeatable value. Don't miss your chance to own a piece of Chatham with this exceptional property.
Courtesy: Howard Hanna Capital, Inc.
518-371-4500
Step into these two beautifully restored historic homes where timeless character blends seamlessly with today's modern conveniences. 30 Austerlitz Street (3Br 2Ba 1582 Sq Ft) and 2 High Street (3Br 2Ba 1572 Sq ft) are being sold together for 850,000 each home is on a separate building lot. Every detail has been thoughtfully updated, from new heating/Central air systems and high-end finishes to spacious, light-filled living areas designed for comfort and style. Enjoy two inviting porches — perfect for morning coffee, evening relaxation, or entertaining friends. Located in vibrant downtown Chatham with the new Shaker Museum coming soon just a short walk away, these homes offer the rare combination of historic charm, modern upgrades, and an exciting community atmosphere. Don't miss your chance to own a piece of history reimagined for today's lifestyle.
Step into these two beautifully restored historic homes where timeless character blends seamlessly with today's modern conveniences.2 High Street (3Br 2Ba 1572 Sq ft) and 30 Austerlitz Street (3Br 2Ba 1582 Sq Ft) are being sold together for $850,000 each home is on a separate building lot. Every detail has been thoughtfully updated, from new heating/Central air systems and high-end finishes to spacious, light-filled living areas designed for comfort and style. Enjoy two inviting porches — perfect for morning coffee, evening relaxation, or entertaining friends. Located in vibrant downtown Chatham with the new Shaker Museum coming soon just a short walk away, these homes offer the rare combination of historic charm, modern upgrades, and an exciting community atmosphere. Don't miss your chance to own a piece of history reimagined for today's lifestyle.
Courtesy: Gabel Real Estate
518-392-4975
Unique opportunity to own an 1892 Colonial in Chatham. Handcrafted cherry kitchen made by local artisans. Extensive countertops with seating perfect for cooking for holidays and dinner parties. Large dining room and living room with high ceilings, original floors, and moldings. Large windows to bring the light in. Three bedrooms on the second floor. Laundry on the second floor. Finished third level with plumbing in waiting to be finished into a bath or studio. Perfect space for home office, fourth bedroom, play or creative space. Level yard meandering back to a stream. The perfect spot for barbecues, fire pit nights or a hot summer stream walk. Lovely hardwoods and flowering bushes for color all season. Close to all Chatham has to offer. Walk to the Bartlett house, the Crandall, Chatham, restaurants, Harlem Rail Trail for biking and walking. Oversize two car garage with space four workshop or storage for all your skis and country garden gardening equipment. Level land perfect for a vegetable garden. A place that needs some paint and simple cosmetics to bring it to the next level of a forever home. Sweat equity and simple changes could make the house just smashing. Come, take a look you will be pleasantly surprised. Great investment in a historic town.
Courtesy: Houlihan Lawrence, Inc
518-822-0300
Village Charm Meets Modern Luxury: Historic Chatham Home for Sale An impeccably remodeled 3-bedroom, 2-bath home, originally built in 1863 is available now. Nestled on a semi-private lot in the heart of Chatham Village, this property offers an unparalleled blend of classic charm and contemporary living, all within walking distance of the area's vibrant amenities. Every system in the home has been completely upgraded, ensuring efficiency and peace of mind. Thoughtful renovations highlight the home's original character, with details that evoke its 19th-century charm, such as original timber framing, seamlessly integrated with modern finishes. The spacious and inviting living areas are perfect for both intimate gatherings and entertaining. A cozy woodstove adds warmth and ambiance during cooler months, creating a true hearth-and-home feel. The kitchen and bathrooms have been updated with thoughtful materials and fixtures, offering both style and functionality. The third level features a semi-finished attic space ready for studio/office room completion. Outside, the property provides a tranquil oasis, ideal for relaxation or outdoor activities. A large deck offers the perfect spot for al fresco dining, morning coffee, or simply enjoying the peaceful surroundings. One of the most appealing features of this property is its prime location in Chatham Village. Enjoy the convenience of being able to walk to all local amenities, including charming shops, restaurants, historic theater, cultural attractions such as the soon to be completed Shaker Museum, and community events. Experience the true essence of village living with everything you need just steps from your front door. Chatham is also conveniently located to many Hudson Valley and Berkshire towns and attractions; Hudson, Kinderhook, Great Barrington, Lenox, and Albany are all a short drive away. Tanglewood, Art Omi, PS21, and multiple ski resorts are easily accessible
Serene Colonial Retreat on 5.79 Wooded Acres with Private Pond Nestled off a quiet secondary road, this low-maintenance Colonial-style home offers 2,860 sq. ft. of peaceful living surrounded by woods on all sides. Enjoy the beauty of nature and ultimate privacy on 5.79 acres featuring a landscaped yard, a pond stocked with largemouth bass, and ample space for expansion—perfect for an inground pool or garden oasis. Inside, the home boasts a spacious layout with a fireplaced living room, formal dining room, dine-in kitchen, and a rear deck ideal for al fresco meals. The second floor includes a private en-suite primary bedroom on one end and three additional bedrooms plus a full bath on the other—easily convertible to five bedrooms if needed. A large bonus room connects the attached one-car garage to the main house, complemented by a separate storage shed for added convenience. The full basement includes a brick fireplace, laundry area, generous storage, and workspace. Recent upgrades include propane heating, on-demand hot water, enhanced insulation, and garage storage. Located just minutes from the Taconic Parkway and close to shopping and dining, this tranquil property blends rural charm with modern comfort.
Courtesy: Coldwell Banker Advisor Realty
518-828-7111
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 winds its way through the property, offering the perfect backdrop for nature walks, picnics, or simply enjoying a quiet moment of reflection. Imagine sipping your morning coffee on the porch, listening to the gentle sounds of the brook and savoring the tranquility that surrounds you. Catskill mountain views and awesome sunsets can be found farther back on the acreage. This property offers a rare opportunity to own a piece of history while enjoying the comforts of today. **This property is now under auction terms. All Bids must be submitted during the auction via the property's listing page. Auction Dates: 11/24/2025 - 11/26/2025 Property Detail Page (PDP): https://www.servicelinkauction.com/property-details/1896-county-route-9-chatham-12037-ny-united-states-trd This sale is subject to a 5 or 2,500 dollar minimum buyer's premium pursuant to the auction Terms & Conditions. All bids will be subject to seller approval (minimums may apply
Courtesy: Anderson Agency
518-758-6340
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.
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.
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.
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**
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 surroundings, the home is nestled among woodlands, wetlands, and wild grasses, all part of a stunning garden created by a renowned restoration gardener.The home's layout is a masterclass in thoughtful design, with multiple levels that offer both connection and seclusion. Each space flows effortlessly into the next, creating a sense of harmony and ease. The primary suite is a true retreat, perched above the serene waterfall and complete with its own private balcony, perfect for morning coffee or evening reflection.A hidden tunnel leads you to your private gym and studio, offering both inspiration and solitude. Though the setting feels completely secluded, you're just five minutes from a morning coffee in charming Chatham Village.A fair warning: your guests may never want to leave.
The prefect blend of farm house and barn built in 1900, a stunning renovation and an excellent location makes this a move-in ready home to enjoy on day one. Situated on 1 acre and surrounded by acres of open field, a rushing stream and a large fenced in growing garden (ready for the season) makes this an easy to maintain property. Coziness, charm, and sophistication is what you will experience upon first entering the home.The contemporary country kitchen is a cooks delight. A beamed ceiling, gleaming wide board wood floors and, a screened porch offers a stunning and livable hanging-out kitchen environment. The sunny living room with a WB fireplace creates an inviting room to entertain in or just relax. There is a first floor bedroom and a full bathUpstairs, there are 2 bedrooms and a full bath. The main bedroom is a delightfully open and loft-like space with the warmth of wide board pine flooring and original details. A barn-garage has room for a vehicle and a workshop. The rolling landscape views from the screened in porch and the Kline Kill' across the road gives you ample privacy in this incredibly convenient location. Minutes to shopping, Chatham Village, and The Taconic, Any easy drive to Hudson and The Berkshires.
Situated on one acre on a peaceful country road and surrounded by picturesque farmland, this charming ranch is ready for its next chapter. From the privacy of your back deck you'll enjoy the sights and sounds of nature creating a calming retreat. Located just 10 minutes from the Village of Chatham you can enjoy the rural charm at home and still be close to all the amenities. Come take a look and make it your own.
Nice three story Village home on a side street. The street level has a garage, laundry area, guest space and bathroom or finish the rest of the first level for a studio or in law apartment. The second level has a kitchen, dining area, living room, two bedrooms, full bath and an enclosed sunny front porch to enjoy your morning coffee or your afternoon cocktail. The third level has a primary bedroom and a large open space that can be made into a studio? home office or primary bathroom and walk in closet. Lots of possibilities with this home. The charming, low-maintenance side yard is perfect for a small garden, a fire pit, and a place to relax. Bring your dining space and grill outdoors on the large deck off of the kitchen. The garage has plenty of storage space and can park one car; there is also off-street parking for two additional vehicles. This home is within walking distance of Main Street, the Fairgrounds, and all that Chatham offers. Possibilities abound with this charming home!
This beautifully crafted post-and-beam house on 8.22 acres, can accommodate large gatherings but is equally suited to small family living. The main floor features a Great Room with Kitchen and Newly constructed Butler's Pantry, which are all laid out perfectly to enjoy the Views, or access the large Wraparound Deck. This floor also includes the Primary Bedroom w/ Ensuite, plus two additional bedrooms and additional full bath for single floor living. The fully finished lower floor is currently set up as a multi-functional entertainment center, with an Exercise Room, a large new Sauna, wet-bar and 4th bedroom. Mechanical Upgrades include Radiant Heat floors and new water heater, well pump and pressure tank.The quiet setting feels remote but is just a 10-minute drive to the Village of Chatham, and less than half hour to Hudson or the Berkshires, where there are many fine restaurants to choose from.Open house, Saturday, March 22nd. from 11:00 to 1:00pm
Former Schoolhouse Completely Redone1840s 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.
Discover this exceptional custom home nestled on 5.97 acres, complete with a serene ponda perfect blend of privacy and convenience. Located in Chatham, this property offers endless potential, whether you're seeking a private retreat or an investment opportunity. Currently configured as a two-unit, it can easily be transformed into a charming single-family residence. Since its purchase in 2020, the home has seen numerous upgrades, including a brand new high-efficiency furnace, new roof, new generator, new flooring, and a terrific kitchen renovation. Ideal for entertaining or family gatherings, the expansive 1,000 sq ft covered deck overlooks the pond and pool. Enjoy outdoor activities like fishing or relax in the peaceful surroundings. Just over a mile from Main Street Chatham, the location is perfect for walking or biking to local amenities like restaurants, shops, and banks. With easy access to the Taconic Parkway and I-90, you're only 2 1/2 hours from NYC and 30 minutes to downtown Albany or the Berkshires.
Charming 1850 two-family home in the heart of Chatham Village, tastefully renovated by a nationally known writer. Live on one side and rent the other, or use as a pure investment. Just a short trip to Main Street, with its classic Crandell Theatre, award-winning brewery, Bimi's Canteen, and all the small-town energy you want. Out front of the home is a deep front yard, wild berries, and a rocking chair porch. Out back? A private deck tucked into a green hillside. Inside: side-by-side two-bedroom units with separate utilities, 200 amp service, updated baths The property also features newer siding and off-street parking. Original wide board floors and fresh upgrades throughout. Both units are vacant and ready for their next steward. The keys are waiting. Come take a look!
Custom designed and built country contemporary in a very quiet setting. This light filled home offers almost 4000 sq ft of spacious, one level living. The finished living area is ADA compliant with open floor plan and wide passages. The Great room is central to the home and leads to additional gathering rooms, breakfast area, screened porch and stone terrace. There is an en suite master, with 3 additional bedrooms , 1 1/2 baths, plus laundry. The basement is substantial and dry, great for storage, or create a gym or media room. The whole house generator relieves any anxiety about power outages. This 5 acre setting is peaceful, a mixture of open and woods, with a small pony barn barn and fenced paddock. A fabulous location only 5 minutes to the Taconic State Parkway, 10 minutes into Chatham village, and 25 min to Hudson or Great Barrington.
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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.
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.
