Old Chatham NY Real Estate & Homes for Sale

Introducing a Prime Investment Opportunity: This well-maintained two-family home on Glenwood Blvd. offers the perfect blend of comfort and potential rental income. With three bedrooms and four baths (two full, two partial), it's designed to accommodate families or savvy investors looking to capitalize on the rental market. The property features a spacious living room in each unit, and a fireplace on the first floor, ideal for relaxation or entertaining guests. The kitchens are equipped with range, stove and ample cabinet space. Both units have access to the washer and dryer in the basement. Outside, the property boasts a well-manicured yard, offering a serene backdrop for outdoor activities. The paved driveway and detached garage provide ample parking and storage space for residents. Conveniently located midway between Hudson and Greenport, this property offers easy access to shopping, dining, and entertainment options. With downtown Warren Street just minutes away and New York City within a 2.5-hour drive, it's an attractive option for commuters or weekend getaways.

Indulge in opulent living in Columbia County, NY! This modern home offers panoramic views of the Berkshire Hills & Catamount Mountains. Enter a grand hallway leading to a dining room with floor-to-ceiling windows showcasing the pool area. The chef's kitchen opens to a spacious Great Room with a fireplace and breathtaking vistas. A loft library offers tranquility. A home office can double as a guest bedroom. The first floor features three guest bedrooms, a gym with sauna, and pool access. The upper level boasts a master suite with a fireplace and private terrace. A grand roof deck overlooks the pool, hot tub, and outdoor kitchen. The lower level features a movie room, laundry, and half-bath. Situated on 10+ acres of landscaped property with lawns and country fields, this is the ultimate country escape. Experience luxury living at its best in Columbia County!

Introducing Van Rensselaer Lower Manor. Built c1685 onward, this historical home is situated on 62 acres of green lawns, fields and wooded terrain that offer Catskill Mountain views. The main house of the estate recently renovated to preserve past details while introducing modern amenities consists of over 5,000 sq ft of living space with an additional 2,000 sq ft separate studio building and a 2,800 sq ft barn. Approach the home via a circular driveway and enter through a gracious wide hall flanked by the south and north wings of the house. The south wing features a cozy living room with a majestic hearth, leading to a dining room and summer kitchen adorned with French doors opening to a charming gravel patio offering endless nights of entertaining. A convenient powder room and an informal sitting room/office complete this wing. Meanwhile, in the North wing, one is greeted by the original kitchen hearth and bake oven. The wooden mantel has been stripped to lend a more contemporary feel. A second dining room and (winter) kitchen are found off this living space all complimented by a tastefully renovated full bathroom. Three separate stairways provide access to a sprawling second floor with a total of eight rooms, 5 currently set up as bedrooms. Three full baths, all elegantly renovated, complete the second level. Step outside to discover a c1825 post-and-beam barn at the edge of a 60-acre wooded expanse. Significant restoration has been done to maintain its integrity and provide striking views of the Catskill Mountains. Sited closer to the road stands the Flower Shop (zoned for retail), a fully renovated 1950s structure, currently utilized as an art studio. This space boasts 10'8" ceilings, a two-car garage, full bathroom, and large plate glass windows with soundproof inserts. These south facing windows create a soft glow and clean sensibility meant to inspire the pursuit of one's entrepreneurial dreams. Every element of this estate from its 17th century Manor home to the more contemporary Art Studio has been thoughtfully restored to accentuate original details without sacrificing modern comforts. A sophisticated contemporary palette blends seamlessly with the enduring charm of hand-hewn wide board floors, forged hardware, original doors and countless other details to make this property timeless yet current. Located in historic Claverack, the Lower Manor is 10 min to Hudson / Amtrak, 15 min to Hillsdale, 2 hours to NYC

Built circa 1860, Bollard Pearl House stands as a historic gem in the heart of Hudson, blending original architectural details with striking design and modern luxury. Nestled on a quiet neighborhood street, yet just a short stroll from the vibrant bustle of Warren Street's restaurants and shops, this charming residence has undergone a designer renovation. Every detail has been thoughtfully considered, from the comprehensive remodel of the kitchen and primary bathroom to the installation of new air conditioning and electric systems, and designer fixtures, to name just a few. Available fully furnished with private parking, a fenced-in yard, and wrap-around porch, the Bollard Pearl House offers idyllic neighborhood living in one of Upstate's most coveted cities.

Nicely renovated sunny two family home on a quiet street with a fenced in garden and parking in the alleyway. Both apartments have open design layout with split ac/heating units. The second story unit has a third floor loft like bonus room. This building has a strong Airbnb income history, which can be provided upon request. An easy walk to Warren Street with all of Hudson's marvelous restaurants and shops. Could easily be converted back to a single family.

This historic 1780's Dutch Colonial home sounds like a dream! From the charming details to the lush surroundings, it's truly a unique find. The Koi pond with its waterfall and the stone patio with a gorgeous archway must create a magical atmosphere. And being walking distance to local amenities while still having the tranquility of a rural setting is a rare combination. The interior is just as enchanting, with the family room exuding brightness and warmth, perfect for both indoor and outdoor gatherings. The stone flooring with radiant heat sounds luxurious, and the pellet stove adds a cozy touch. It's wonderful how the space seamlessly flows into the kitchen, making entertaining a breeze. The dining room sounds like the heart of the home, with its beamed ceiling and wide-plank floors creating an authentic antique ambiance. And who wouldn't want to gather by the fireplace for celebrations? Upstairs, the bedrooms maintain the home's charm with wide plank flooring and built-ins for storage. The front hallway's versatility for crafting, office space, or a reading nook adds to the home's appeal. The barn ensemble offering additional space is a fantastic bonus, especially with its pre-existing business potential. Overall, this home seems like a treasure waiting to be discovered by its next owner. It's clear the current owners have cherished it, and it's exciting to think about the memories and adventures awaiting the new inhabitants.

Newly constructed, 2016 townhouse with two detached studios. The luxury townhouse is the complete package offering prime location, luxurious finishes, fine craftsmanship, an ideal open floor plan spanning 2 stories. Every surface & system is to state-of-the-art standards. Features include open high-end kitchens with sitting areas, many custom design extras, 8 bedrooms, 8 bathrooms, central AC. The courtyard studios are modern design also with AC, opening onto the enclosed garden with four garage bays below. Perfect work or guest space. The fenced-in backyard is fully landscaped with stone and slate stairways, and pathways. A true masterwork of design. Maintenance free, in turn-key condition. Walking distance to Amtrak and the restaurants and amenities on Hudson's Warren Street, and a few short blocks from the Hudson River. Investment, live/work.

Newly constructed, 2016 townhouse with detached studio. The luxury townhouse is the complete package offering prime location, luxurious finishes, fine craftsmanship, an ideal open floor plan spanning 2 stories. Every surface & system is to state-of-the-art standards. Features include open high-end kitchens with sitting areas, many custom design extras, 4 bedrooms, 4 bathrooms, central AC. The courtyard studio is of modern design also with AC, opening onto the enclosed garden with two garage bays below. Perfect work or guest space. The fenced-in backyard is fully landscaped with stone and slate stairways, and pathways. A true masterwork of design. Maintenance free, in turn-key condition. Walking distance to Amtrak and the restaurants and amenities on Hudson's Warren Street, and a few short blocks from the Hudson River. Parcel #109.44-1-20.100

A Brick Federal with pedigree, this c1820 Warren Street building was built by one of Hudson's founding fathers and later owned by the Van Rensselaer family. Comprised of three units, there is a fabulous owner's duplex taking up the top two of three floors, while a retail space and a 1BR apartment make up the first. Sited on a double lot, the backyard is wide with beautiful gardens and a three bay garage with endless potential. The house is rich in periods and history having been renovated in different eras with distinct tastes, until the current owners did a full, cohesive renovation utilizing the best local craftsmen. The upstairs duplex has an open concept third floor with vaulted ceilings and exposed ductwork. The kitchen and common spaces are here to capture a fabulous view of the Catskill range. The second floor comprises two bedrooms and an office, the master is fabulously generous and takes over the entire eastern wing. The retail space is gorgeous with big street facing windows it runs the western length of the building and has views of the garden in the back. There is also a one bedroom apartment, well appointed, well sized, and recently renovated. A chance to own part of Hudson's rich history, 239 Warren offers both a great investment and lifestyle.

One of Hudson's most unique, important Warren Street multi-use buildings, strategically located in the prime 500 Warren Street block. Complete gut renovation 2022. First floor, operating retail space and an office currently rented. Second and third floors are renovated apartments. P-stone patio/parking area in back off Prison Alley,AboveGrade:5084,EQUIPMENT:Carbon Monoxide Detector,Smoke Detectors,FLOORING:Ceramic Tile,Wood,FOUNDATION:Brick,Stone,Level 1 Desc:RETAIL. OFFICE BA-1, STORAGE, FITTING ROOMS,Level 2 Desc:BR-1 BR-1 BA-2 LR DR KITCH PORCH/DECK,Level 3 Desc:BR-3 BR-4 BA-3 LR DR KITCH,OTHERROOMS:Professional Suite,ROOF:Rubber

Two bedroom plus bonus room! Beautiful quiet residential street in Sought after Claverack. Just three miles to Warren St! This is a well-loved home! It was built by the owner in 1954 and has never been sold. Tax data says 2 bedrooms but there is an additional room on main level with a closet. This home has beautiful hardwood floors, Spacious Living room with working Bluestone fireplace. Roof is 10 years old; Septic is a 1000 gallon concrete tank, Community water, new high efficiency boiler. Large basement with washer dryer and tons of storage. There is also a 1 car attached garage. Home was lovingly cared for and owner has receipts for Maintenace and upgrades.

Private country setting, contemporary design, and energy efficiency all come together in a serene landscape setting with beautiful views of Catamount Mountain. 3500 SF, stained cedar sided home, 4-bedroom, 3.5-bathroom. Home is sited to maximize long distant views. This certified passive home is industry leading, with its triple insulated floor to ceiling windows and doors, high R-value walls and ceiling and an energy recovery/ventilation system. Finished three-car garage can easily accommodate EV charging stations and an abundance of additional storage needs. The centerpiece of the home is a large open floor-plan kitchen/dining/living space with 13' + high ceilings. Oversized sliding doors from this space make the connection to the concrete paver patio, meadows and woodlands, second nature. Close to the Berkshires, Great Barrington and Stockbridge, 30 minutes to Hudson and minutes to the hamlet of Hillsdale, and Catamount. Experience true green living.

Welcome to Locust Cove, an exclusive gated over 55 condo community in the picturesque town of Oakdale. This upper unit condo boasts two spacious bedrooms, a luxurious bath, and a gourmet kitchen that will inspire your inner chef. The expansive master bedroom offers ample space for relaxation, while the beautifully appointed bathroom adds a touch of elegance to your daily routine. Entertain guests in the large living room or enjoy the amenities of the clubhouse, all conveniently located within the community. With private parking and a serene setting, this condo is the epitome of comfortable living. Please note, this sought-after condo falls under affordable housing, with specific income requirements outlined in the broker's notes. Don't miss out on this opportunity, as it's priced competitively and won't last long!

Nestled on desirable Union Street in Hudson, a short stroll from vibrant Warren Street, Olive House stands as a captivating turn-key two-family home. Recently upgraded with clean design elements, new systems, and a renovated backyard, this home retains the coveted allure of its circa 1930s charm. Offering numerous possibilities for expansion and use, Olive House presents a rare move-in ready opportunity brimming with potential. Live in one unit while generating rental income from the other, utilize as an artist live-work space, or easily convert to a grand single-family dwelling in one of Upstate New York's most sought-after locations.

Nestled on desirable Union Street in Hudson, a short stroll from vibrant Warren Street, Olive House stands as a captivating turn-key two-family home. Recently upgraded with clean design elements, new systems, and a renovated backyard, this home retains the coveted allure of its circa 1930s charm. Offering numerous possibilities for expansion and use, Olive House presents a rare move-in ready opportunity brimming with potential. Live in one unit while generating rental income from the other, utilize as an artist live-work space, or easily convert to a grand single-family dwelling in one of Upstate New York's most sought-after locations.

This beautifully updated home in Athens, NY, offers the perfect blend of comfort and charm, nestled on a generous 1.3-acre corner lot with over 500 feet of road frontage. The property is move-in ready and features wood and tile floors, modernized kitchen and bathrooms, spacious rooms, and abundant storage. The large, fully fenced yard is ideal for relaxing, playing, or entertaining, with a deck perfect for watching river fireworks. There are two comfortable apartments for hosting guests or relatives, making this home versatile and welcoming for all. Athens, NY, is a vibrant small town with a rich community spirit and plenty of activities to keep you engaged. Enjoy music by the river all summer, fresh baguettes from the Catskill Bread Company, art shows at the Athens Cultural Center, and fun trivia nights at the local brewery. Stay active with yoga at Tenth House Health and explore the local culinary scene at Seconds Restaurant or Stewart House. For outdoor enthusiasts, there are ample opportunities for adventure, including kayaking, eagle watching, and biking. You can also take the ferry to Hudson for shopping or hop on a train to NYC for a day trip. This home is ready for your personal touches, whether you choose to live in it full-time, use it as an AirBnB, or explore other options. Embrace the peace and joy this special property in Athens has to offer.

Discover the timeless elegance of this Edwardian-era gem in Hudson, NY. Built in 1908, this stately residence joins historic charm with modern comfort, offering a captivating blend of old-world grandeur and contemporary convenience. With four bedrooms, two bathrooms, an office, high ceilings, first floor parlors and fireplace this home provides for both daily living and entertaining. Ascend to the walk-up attic, spanning over 500 square feet, and let your imagination soar - whether a cozy retreat, artist's studio, or peaceful sanctuary, the possibilities are endless. Upgrades include a seamless 40 year metal roof, solar panels for energy efficiency, durable aluminum siding, new back porch room, new kitchen and new bathrooms. Adorned with gleaming hardwood floors, the interior exudes a warm and inviting ambiance. Additionally, tucked away in the detached garage behind the house up the hill, discover the charming cabin room featuring a wood stove, rear west facing balcony and own entrance. It's the perfect spot to unwind and reconnect with nature without leaving the comfort of home. Just a block from upper Warren St and mile from the Hudson Amtrak station, commuting to New York City or nearby destinations is effortless. Explore the eclectic shops, gourmet restaurants, and cultural attractions of Hudson, all within reach. Don't miss your chance to make this treasure your own - schedule a showing today and embark on a journey through the enchanting past and present of Hudson living! (Public Square Footage does not count Attic or Sunroom)

Located on a quiet cul-de-sac, this 1875 Victorian home boasts 5 bedrooms, all with ensuite bathrooms, a large living room, library, dining room and an additional guest powder room as well as a fully equipped kitchen. Modern touches were added in 2008 when the property was converted into a bed and breakfast, which operated successfully for over 12 years. Two wood burning fireplaces and two gas fireplaces create the perfect atmosphere in winter, and plenty of outdoor space are ideal for entertaining in warmer weather. Period details are found throughout the property including a sweeping front staircase, pocket doors and inlaid hardwood floors. While the home is move in ready, some TLC offers the buyer an opportunity to apply their own creative touches to make this historic house your home. (interior photographs are staged),AboveGrade:3900,Cooling:Attic Fan,EQUIPMENT:Carbon Monoxide Detector,Smoke Detectors,ExteriorFeatures:Landscaped,FLOORING:Ceramic Tile,Parquet,Wood,FOUNDATION:Stone,Heating:Gas,InteriorFeatures:French Doors,Level 1 Desc:LR, DR, KIT, LIB, BR BA,Level 2 Desc:BR, BR, BR, BR, BA BA BA BA,ROOF:Metal,Rubber

Step back in time with this 1881 2-story vintage home, filled with Old-World Charm and Character. Opportunity awaits with an interior ready for a move-in while the exterior just needs a little TLC to shine. Located in the Athens Village Historic District, near the Hudson River and a short ride to Trendy Hudson Downtown. Ideal for Nature Lovers, with Kayak launches, Hiking, and Wineries nearby. Features a front porch, exquisitely detailed entry doors, a spacious Main Level with an Open Floor plan, Large Eat-In Kitchen with a back staircase leading to the second level. Three spacious bedrooms on the second level with an updated full bath. Freshly Painted, Original Trim Work, and Newer Laminate Floors. Municipal Water & Sewer. Zoned for Residential or Special Commercial uses. Explore the Possibilities at this Prime Village location!

Nestled in the charming Historic District of Athens, NY, this magnificent Solid Brick Church built in 1832 offers endless possibilities for a visionary owner. Steeped in history, this architectural gem presents a rare opportunity to create something truly extraordinary. Whether you dream of preserving its sacred beauty as a place of worship or envision a stunning conversion into a one-of-a-kind residence, professional office, or many other options, the choice is yours. With its soaring ceilings, intricate stained glass windows, Hardwood Floors, and bell tower, this property exudes character and charm at every turn. The main level features a Sanctuary, 2 Offices, a Conference Room, and a Study. The Walk-Out Lower Level flooded with natural light offers a Large Kitchen, a Massive Recreational Area, Bathrooms, and Utility Areas. Perfect for a variety of uses and activities! The building boasts almost 6000 square feet of space, with a one-car detached garage and ample off-street parking available. Municipal Water and Sewer. Located in a PRIME Village Location near 2nd Ave with easy access to local amenities and the picturesque Hudson River, this property is a gateway to unlimited potential. Perfect for outdoor enthusiasts with a kayak launch, hiking, and exploring trails nearby. Discover trendy Hudson NY, wineries, and more just a stone's throw away. Embrace the opportunity to bring new life to this historic treasure and create a legacy that will endure for generations to come.

Discover a harmonious blend of luxury and sustainability at Lakeview Hideaway. At the end of a long private driveway, this certified green-build home features a meticulously crafted interior showcasing panoramic views and an array of superior energy-efficient features. The first-floor bedrooms provide convenience, while the second-floor open living space feels like a glass treehouse, offering breathtaking views of the Berkshire hills and a private lake. Spanning over 25 acres across two lots and primed for additional building, discover miles of walking/ATV trails and endless outdoor exploration right at your doorstep. Secluded yet accessible, Lakeview Hideaway is convenient to farmers' markets, ski mountains, Albany Airport, and all the quintessential gems that Upstate has to offer.

OLIVER WISWALL HUDSON RIVER HOUSE c1835 Indulge in the allure of mesmerizing views that will captivate your senses and imagination. Perched atop Mt. Merino, the iconic Oliver Wiswall House stands as a beacon of timeless elegance, offering commanding forever vistas of the majestic Hudson River. Originally built in 1835 by one of Hudson's esteemed mayors and founder of Greenport, this historic Greek Revival masterpiece is steeped in a rich tapestry of heritage. Set on 39 acres this residence commands not only the tranquil Hudson River but also offers sweeping panoramas that encompass the iconic Athens lighthouse and the picturesque Catskill Mountains painting the horizon. Rarely does an opportunity arise to own a piece of history so deeply entrenched in the fabric of the region. Step inside to discover a meticulous and thoughtful restoration, where every detail has been methodically preserved and enhanced. From the grandeur of the classic brick Greek Revival architecture to the intricate details of stately moldings, marble fireplaces, and most original doors and windows, the Oliver Wiswall House exudes an air of timeless sophistication. The interior layout features a gracious center hall entry leading to the formal living room, library and formal dining room all adorned with iconic moldings and meticulous craftsmanship that effortlessly blends historic charm with modern comforts all bathed in natural light pouring in countless oversized windows. A seamless transition takes you to the later postmodernism addition, where a grand great room awaits boasting curved, soaring ceilings a chef-worthy open kitchen, gracious dining round, fantasy mud room, pantry, and laundry area, all thoughtfully designed to complement the home's historic grandeur. With four bedrooms and three and a half baths, including the upstairs sumptuous primary suite, guest en-suite, and two additional bedrooms and bath, all flooded with natural light, high ceilings and offering captivating river views, this home is a sanctuary of comfort and luxury. Step outside onto multi-level decks and a patio, where you can immerse yourself in the mesmerizing expanse of the river's beauty. Whether you're a star-gazer or simply seeking a tranquil retreat, the Oliver Wiswall House offers the perfect sanctuary amidst its sprawling lawns and panoramic views. Just moments to Hudson, Amtrak and to all the Hudson Valley has to offer while just 2 hrs to NYC

Welcome to Meadow Wood. This elegant property on a secluded reach of the Green River epitomizes the concept of indoor/outdoor living. The graceful and meticulously maintained 30 acre estate features specimen trees, established gardens, a lilypond, terraces, pastoral views, and wonderful privacy. The custom home, built by one of the region's premiere builders, has been featured in design magazines, garden tours & has received a Garden Club of America award for its ethos & thoughtful use of building materials. The house was constructed using sustainable & recycled low maintenance building materials designed to last a lifetime. In addition to the light-filled main house, the property includes the gardens, fenced fields, a 2 car garage w/ potting room and a studio space. The Gunite pool is surrounded by an espaliered apple tree fence & generous stone terrace. The large screened pool house includes 1/2 bath, outdoor shower, kitchenette & massive fireplace. Further from the house is the barn complex consisting of a 2 bedroom apartment with yard & patio, separate studio apartment and 4 garage bays. A barn, cutting gardens, and a separate private drive complete this part of the estate. Hidden from the road, the main house is approached by a long drive lined with mature Scarlet Oaks & daffodils. A courtyard filled with specimen crabapple trees, stone walls & walkways creates the welcome entry to this one level home.The exterior walls are planted w/ climbing hydrangea that blur the

Welcome to this charming vintage home nestled in Berlin. Crafted by a local artisan, the kitchen exudes timeless elegance and is meticulously maintained, offering a perfect blend of nostalgia and functionality. Throughout the home, you'll find an abundance of delightful built-ins, enhancing both storage and character. Step inside to discover the allure of hardwood floors that grace the main level, providing a warm and inviting atmosphere. Ascend to the second floor where wide pine flooring adds a touch of rustic charm, seamlessly marrying tradition with modern comfort. This cozy residence boasts three bedrooms and one full bath, ideal for accommodating families or hosting guests. Outside, a detached two-car garage awaits, offering ample space for vehicles and additional storage. Situated amidst, This property offers not only a beautiful home but also a convenient lifestyle. Don't miss the opportunity to make this vintage gem your own.

Discover Trumbull Farmhouse, a classic estate on a quiet country road just minutes outside of Hudson. Circa 1860, this heritage property boasts a spacious farmhouse, a guest cottage, and an original barn alongside a family-operated lavender farm with views of bucolic rolling hills. The interior is full of original charm and the grounds feature a saltwater pool and inviting patios, perfect for country entertaining. Beyond the property lines, Trumbull Farmhouse is enveloped by acres of Columbia Land Conservancy, visually expanding its borders and ensuring protection from future development. A stroll to the renowned Churchtown Dairy or a short drive to other premier area destinations makes Trumbull Farmhouse the ideal blend of a tranquil nature retreat with convenient Upstate access.