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
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.
Open House Saturday 5/9 from 11-1 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.
CEDAR HILL - Architectural Country Living at its Finest - is the embodiment of 21st-century modern luxury. Elevated on 10 private acres with sweeping mountain views, a gracious mix of open and wooded landscape, a serene spring-fed lily pond, and an organic vegetable garden, this newly expanded and reimagined six-bedroom home is set in Old Chatham, one of the most coveted corners of New York’s historic Hudson Valley. The home engages seamlessly with its natural surroundings through walls of glass that draw in the changing seasons - from spring’s first blooms and summer’s golden light to autumn’s rich palette and the quiet beauty of snow-covered peaks. Abundant natural light and warm finishes create interiors that balance architectural precision with a sense of comfort and ease. The grounds include a 50-foot heated in-ground Gunite salt-water pool and spa, surrounded by expansive bluestone patios. Thoughtfully positioned just beyond, a cedar-clad spa pavilion - with sauna and custom sleek stainless hot tub - is connected to the house by a breezeway, creates a natural extension of the home while preserving a sense of privacy. Southern light fills this entire setting throughout the day, enhancing both the interiors and outdoor living spaces. A deco-turf night-lit tennis court built by a premier tennis contractor in the Berkshires complete the private, resort-like atmosphere, ideal for restorative retreats, entertaining, or quiet relaxation. The formal living room, with soaring 22-foot ceilings, anchored by a wood-burning fireplace flows effortlessly into a gracious dining area, an open kitchen and butler’s pantry and a secondary gathering room with its own wood-burning fireplace. A game and media room opens directly to the pool terrace, while the main level also offers a first-floor bedroom, full plus half- bath, along with a beautifully designed mudroom with breezeway access. Upstairs, the primary suite serves as a private sanctuary, with glass doors opening to a deck that captures mountain vistas with south and west exposures. Four additional bedrooms, bathroom, a flexible-use room with grand terrace, and a second laundry provide ample space for guests, work and wellness. The property, rebuilt and expanded over a multi-year renovation, was completed in 2023. Designed for year-round, sustainable modern living. Solar power, radiant heated interiors, a three-car heated garage, and multiple EV charging stations ensure comfort and efficiency in every season. Underground utilities further enhance the natural setting. Surrounded by the natural beauty of the Hudson Valley and the Berkshires, Cedar Hill offers access to hiking, skiing, farm-to-table dining, and cultural destinations - while remaining a peaceful retreat to relax and recharge.
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 pond--creating a setting that feels nothing short of magical. Original details are beautifully preserved throughout, including exposed hand-hewn beams, wide-plank floors, and antique sash windows that bathe the interiors in natural light. The main house is both elegant and inviting, centered around a sky-lit chef's kitchen with marble countertops, an 8-burner Wolf range, Sub-Zero refrigeration, and an exceptional pantry. A gracious yet relaxed layout offers multiple living and entertaining spaces, anchored by two wood-burning fireplaces and opening to both a screened porch and a classic covered porch for seamless indoor-outdoor living. Upstairs, the primary suite is a private retreat with its own fireplace and sitting room, complemented by a Waterworks bath. Three additional bedrooms and two beautifully appointed baths complete the level. The grounds are exceptional--designed for both quiet retreat and effortless entertaining. A free-form gunite pool with pool house and a tennis court are seamlessly integrated into the landscape, offering all-day and evening enjoyment. The spectacular, fully restored barn is a destination unto itself--defined by soaring two-story volumes and a dramatic dual-sided bluestone fireplace. An open kitchen, laundry, and Waterworks bath are seamlessly integrated, while walls of glass frame the pond beyond. Fieldstone and wide-plank wood floors anchor the interiors, with a separate bedroom suite and sleeping loft providing beautifully appointed guest accommodations. A rare offering where every detail--both original and newly imagined--has been executed with exceptional care and quality. Modern amenities including high-speed fiber internet and a property-wide Sonos system ensure seamless living in an extraordinary historic setting.
Turn a Landmark into Your Dream Property - Village of Chatham Opportunities like this don't come around often. Set on a .44-acre double corner lot in the heart of the Village of Chatham, this beautifully maintained former church offers 3,700+ square feet ready to be reimagined into a truly one-of-a-kind. Step inside and you're immediately struck by soaring ceilings, breathtaking stained-glass windows, and an expansive open space filled with natural light--perfect for creating an incredible great room, dramatic living area, or custom-designed space unlike anything else on the market. Beyond the main space, the layout offers incredible flexibility with a large hall, kitchen area, office space, and multiple additional rooms--ideal for bedrooms, home offices, creative studios, or guest areas. The basement provides storage and utility space, while off-street parking adds everyday convenience. Whether you're dreaming of a modern conversion, an artistic retreat, or a bold residential statement property, this building delivers the space, character, and location to make it happen. All of this just steps from Chatham's shops, dining, and village charm. A rare chance to create something unforgettable--bring your vision to life
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 floor-to-ceiling fireplace crafted from native boulders. The flowing open floor plan begins with an expansive wrap-around porch, leading into a vaulted two-story living area and a chef's kitchen featuring stainless appliances and a charming antique Glenwood cast iron stove. The main level hosts two guest bedrooms and a newly renovated full bath with laundry. Upstairs, a versatile landing/office space overlooks the great room, leading to a luxurious primary suite complete with a custom walk-in closet and a spa-like bath featuring a soaking tub and double vanity. Modern efficiency and utility are at the forefront. Recent updates include geothermal heating and cooling, a whole-house generator, a new roof, and an electric car charging station. For the hobbyist or collector, the attached two-car garage features a separate dedicated room, ideal for a professional workshop, art studio, or a temperature-controlled wine cellar. Located minutes from the Spencertown Academy, Chatham, Hawthorne Valley and the Berkshires, this turn-key sanctuary is ready for your summer enjoyment.
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 and perennial gardens. Inside, you'll find warm hardwood floors and a living room with a fireplace made for curling up on chilly nights. With a convenient first-floor bedroom and a quiet office or study, everything you need is right on the main level. Two more bedrooms are tucked away upstairs, and a one-car garage adds the final touch to this village gem.
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 The Taconic Parkway. There are 3 bedrooms, 2 large bedrooms on the upper floor and a smaller bedroom/office on the main level. The 2 full bathrooms are beautifully appointed with distinctive tiling and vanities. A large screened porch adds to the comfort of the property. The sun filled 1.3 acres, (2 lots) with a babbling brook is ready for your gardening expertise. There is a large barn/garage at the far end of the property, which needs some love to create a studio, guest space or workshop. This is a home you will want to see! Whether you seek a full time residence, weekends or a rental property, look no further. The current owner has combined this as a part-time residence and a successful Air B and B. Don't let this home pass you by. Bring your clothes, and move right in, as the home can be purchased fully furnished.
Welcome to this peaceful escape, tucked away on nearly five 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 nature. Set at the end of a long driveway on 4.8 wooded acres coming home feels like a retreat into peach and stillness. This well maintained home features 3 bedrooms and 3 full bathrooms thoughtfully designed to provide ample space for family and guests. Enjoy your coffee and take in the morning sun or the evening sunset from your light filled sunroom and eat in kitchen. Recent updates include new roof and septic system. This property is truly a respite from the pace of modern day living.
c1900's Colonial w/ detached garage located off a quiet side street in the center of coveted Chatham Village NY. 12 miles to Hudson Amtrak, 2 hours to NYC/Manhattan. House rented. Photos pre tenant occupancy. Leave your car at home as you're a short walk to Main St, schools, library, shopping and a delectable variety of eateries, from fine to relaxed dining including Yianni's Chatham House, Bimi's Canteen, Chatham Brewing, Fiesta Cafe and more. Beautifully renovated and updated, this bright Village home sits on an easily manageable and fully usable half-acre lot with circular driveway. Large enclosed porch, 3 bedrooms, 1.5 baths, LR, DR and chef-friendly kitchen w/plenty of counter space and storage. Washer/dryer on main level. Zero maintenance municipal water/sewer. By Appt Only. Minimum 48hr notice to show. No showings before 10am. No Sunday showings per Tenant. Use ShowingTime if possible. Photos pre-occupancy.
Welcome to your own 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 features three bedrooms and three full baths, thoughtfully designed to provide ample private space for family and guests. Enjoy your morning coffee and take in the sunsets from the light-filled sunroom and eat-in kitchen. Recent updates include a new roof and septic system. This property is truly a respite from the pace of modern-day living.
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.
Charming Village home off Kinderhook St. Big yard, big rooms and walking distance to the schools and Main St. A big living room, a big den kitchen and dining room downstairs. Three bedrooms and two full baths upstairs.
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. https://www.hubzu.com/property/94525949074-Chatham-NY-12037
Highest and Best Due by Monday 5/11/26@5pm. Edgehill Estate is a rare offering of period grandeur set against sweeping, unobstructed views of the Catskill Mountains. Prominently positioned and privately sequestered behind a gated entrance, this is a legacy property for those who appreciate scale, setting, and significance.Expansive, light filled rooms span 3,500 square feet of dramatic living space ideal for entertaining. Original hardwood floors and historic architectural details showcase timeless character, while 5 bedrooms and 3 baths provide generous accommodations for family and guests. Outside, more than 7 acres of rolling gardens, mature trees, and open sky create a spectacular setting. An inground pool enhances summer living, and a classic barn with apartment offers exceptional versatility--guest quarters, studio, event space, or collector's retreat. Enjoy privacy without isolation, just a stroll to Chatham Village for acclaimed eateries and the beloved farmers market. The property needs work, but the upside is undeniable. Restore, elevate, and transform this estate into a true Hudson Valley showpiece.
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!
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.
This Chatham Village, one level , 2 bedroom home, on 1.1 acres is waiting for you. Close to all the village amenities while still offering a bit of privacy. The home has been updated over the years with a newer kitchen and bath, a new roof and lighting. A charming wood burning fireplace and large above ground pool makes this a great home for all seasons. Other features of the home includes an attached 2 car garage, a den, hard wood floors, spacious rooms, a back deck, and a full basement.Water and Sewer are provided by the village
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!


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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.