Chatham Homes with Driveway Parking features

Welcome to the charming community of Chatham, nestled in the picturesque Columbia County of New York. Known for its rich history and vibrant small-town atmosphere, Chatham offers a delightful blend of rural charm and modern conveniences. One of the standout features of this area is its exceptional school district, which is highly regarded for its commitment to academic excellence and community involvement. The Chatham Central School District provides a nurturing environment for students of all ages, boasting dedicated educators, a variety of extracurricular activities, and a strong emphasis on preparing students for future success. Families in the area appreciate the close-knit community feel, where parents and children alike can engage in local events and activities.

In addition to its educational offerings, Chatham is home to a variety of beautiful properties, many of which feature driveway parking—a highly sought-after amenity for today’s homeowners. Imagine returning to your own charming abode after a day exploring the scenic landscapes or enjoying local dining and shopping. With driveway parking, you can enjoy the convenience and ease of coming and going without the hassle of street parking. Whether you are looking for a cozy cottage or a spacious family home, Chatham's real estate market has something for everyone.

Experience the perfect blend of community spirit, educational excellence, and comfortable living in Chatham, NY. Discover your dream home today and become a part of this vibrant and welcoming community!

Newest Chatham Homes with Driveway Parking features

$459,000

4 Beds ⋅ 3 Baths ⋅ 1028739 MLS

Beautifully Tucked Away 23 Leggett Road Is A 1.5 Acre Raised Ranch Featuring 4 Bedrooms, 2.5 Bathrooms, Large Living Room With Wood Burning Fireplace With Blower, Harwood Floors & Private Deck With Stairs Leading To The Lower Level & The Yard, Formal Dining Room With Large Bay Window & Hardwood Floors. Updated Kitchen With Granite Counter Tops, Stainless Steel Appliance, Garbage Disposal, Plenty Of Cabinets With Under Cabinet Lighting, Plenty Of Counter Space With Large Bay Window Looking Out To Your Multi Level Front Deck. Primary Suite With Private Entrance As Well As An Updated Bathroom With Large Walk In Shower & Linen Closet, 2 Additional With Double Closets, 1st Floor Laundry Room. Lower Level Features A Large Family Room With Outside Ground Level Entrance, Guest Quarters ( 4th Bedroom ) 1/2 Bathroom, Mud Room/Storage Area. 2 Mini Split Air Conditioners, Stand By Generator, 200 Amp Electric, Propane Gas Cooking, Direct Gas BBQ, All Updated Within The Last 5 Years - Windows, Siding, Kitchen, 2 Full Bathrooms, Roof 10 Years, 2 Car Large Garage, Large Circular Driveway, Enormous Front Yard. Enjoy All The Amenities This Area Has To Offer Golf, Tennis, Pickle Ball, Basketball, Baseball, Playground, 45 Minutes To Saratoga, Near Amtrak Train

23 Leggett Road, Chatham

$3,000,000

4 Beds ⋅ 5 Baths ⋅ 1025867 MLS

Welcome to Sutherland Estate, a private country compound set on more than 56 acres of rolling meadows, gardens, ponds, with Catskill Mountain views. A long paved drive leads to this elegantly designed 5,760-square-foot home, inspired by classic Greek Revival architecture and recently renovated from top to bottom with refined, high-end craftsmanship. The home features a standing-seam metal roof, radiant heated bathroom floors, energy-efficient heat pumps, a whole-home generator, and a fully integrated smart home system for lighting, temperature, and security. Recent upgrades include newly refinished white oak hardwood floors, new luxury vinyl plank basement flooring, a refreshed lighting plan with recessed fixtures and designer pieces from Arteriors and Hinkley, updated Lutron switches and outlets, new HVAC registers and vents, fresh paint, new baseboards, and updated hardware. The main level offers bright, connected gathering spaces with sweeping views of the ponds and Catskill Mountains. Living and dining rooms flow together, anchored by a beautifully appointed kitchen with a large custom island, a counter-depth panelized Sub Zero fridge, and professional-grade appliances. French doors open to a wide stone patio with an outdoor BBQ, framed by landscaped gardens and open lawns. A paneled cherry wood office/library with built-in cabinetry and a wood-burning stove sits beside a three-season sunroom overlooking the pond, while a spacious living room with a gas fireplace completes the main floor. Upstairs, the primary suite offers a private retreat with a gas fireplace, two walk-in closets, and a luxurious bathroom with soaking tub and steam shower; three additional bedrooms, a guest media room, two full bathrooms with updated quartz-top vanities and faucets, and a laundry room complete the second floor. The finished lower level adds a kitchenette, sauna, and full bath with new LVP flooring, ideal for guests or wellness use. An attached three-car heated garage offers additional space for storage. Outdoors, a footbridge crosses the aerated pond, and the grounds include raised-bed gardens, a potting shed, and a newly built, insulated 26x34-foot carriage house offering space for vehicles, a barn, or future ADU conversion. Located minutes from both Chatham and Kinderhook villages, Sutherland Estate offers refined, move-in-ready country living in beautiful Columbia County.

189 Sutherland Road, Chatham

$1,475,000

4 Beds ⋅ 3 Baths ⋅ 1022973 MLS

Days by streams are days well spent. Designed and built by a local master craftsman, this farmhouse fulfills your country dream. Lofty exquisite kitchen. Oversized windows. Deck over looking the stream. Upstairs, large bedrooms and beautifully tiled baths. A guest space over the garage gives anyone a place of their own. Incredible attention to detail. Centrally located, 15 minutes to Hudson, 5 minutes to Chatham and a stroll to Ghent.

48 Konig Road, Ghent

$649,900

3 Beds ⋅ 3 Baths ⋅ 1012896 MLS

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).

2228 State Route 203, Chatham

$989,000

4 Beds ⋅ 3 Baths ⋅ 1007980 MLS

NEW PRICE | TURNKEY HUDSON VALLEY RETREAT WITH SALTWATER POOL | $989,000 - AN EXCEPTIONAL HUDSON VALLEY OPPORTUNITY. This beautifully maintained, turnkey retreat offers 3,424 square feet, four bedrooms, two-and-a-half baths, a resort-style saltwater pool, and a peaceful private setting just minutes from Hudson. Designed for full-time living or weekend escapes, the spacious layout offers room for entertaining, remote work, and hosting family and friends. Outdoors, enjoy an in-ground fiberglass saltwater pool, an illuminated pergola with electricity and a ceiling fan, a custom fire pit, and multiple areas for dining and relaxing. Fiber-optic internet adds modern convenience, while the move-in-ready condition allows you to enjoy the Hudson Valley lifestyle immediately. The famous Bartlett House cafe and bakery is just down the road, with Hudson’s restaurants, shops, galleries, cultural attractions, and Amtrak station approximately 12–15 minutes away. Convenient to the Taconic State Parkway, Lake Taghkanic, hiking, skiing, and year-round recreation. Approximately two hours from New York City, this is a fabulous opportunity to own a spacious, private Hudson Valley retreat with exceptional amenities. "The sellers especially love the peaceful private setting, seamless indoor-outdoor living, evenings around the fire pit and pergola, and the convenience of being moments from Hudson while still feeling like a true escape." WAZE or Google Maps Address: 854 Ghent Mellenville Road, Ghent, NY 12075

854 County Route 9, Ghent

$1,585,000

3 Beds ⋅ 2 Baths ⋅ 998937 MLS

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.

41 Chicory Lane, Austerlitz

$2,285,000

3 Beds ⋅ 3 Baths ⋅ 995720 MLS

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.

53 May Lane, Chatham

$395,000

3 Beds ⋅ 1 Baths ⋅ 958438 MLS

Welcome to Queechy Lake Cottage, a vintage Hudson Valley retreat on Queechy Lake in Northern Columbia County's Canaan. Built in the 1930s on land that once served as a boys' camp, this charming 1,008-square-foot cottage offers indoor-outdoor living with three bedrooms, a full bathroom, and the kind of peaceful lake living that feels increasingly rare. Outside, the compact cottage includes a level lawn with room for a garden, parking for two vehicles, and a spacious deck for entertaining, grilling, or unwinding after a day at the lake. As a member of the Queechy Shores Association, the property includes rare access to a private beach, lake docking, and mooring rights. The beach sits a five-minute walk from the cottage, offering a place to swim, kayak, or simply enjoy the water. The interior centers on an open living area with tall, vaulted ceilings and warm wood paneling that catches beautiful light throughout the day. The original layout maximizes space without sacrificing the intimate scale that defines a true cottage. Large windows frame views of the surrounding pines, and thoughtful updates preserve the vintage atmosphere. A large screened porch with mahogany wood floors extends the living area during warmer months, while the tiled bathroom and efficient kitchen support quiet functionality. Currently configured as a three-season cottage, the property could be converted to year-round use with insulation added to the floors. The location provides a practical balance: close to Tanglewood for summer concerts, the Berkshires for hiking and cultural attractions, and Chatham or Pittsfield for groceries and essentials, yet less than 2.5 hours from New York City. The property sits on a quiet lane within the association, where the pace slows and the focus shifts to seasonal rhythms. Whether used as a weekend escape, a writer's retreat, or a summer residence, Queechy Lake Cottage delivers straightforward lake access and a nostalgic atmosphere. This is a place to settle in and discover the kind of quiet oasis that drew people to the water in the first place. With summer just months away, now is the time to secure your place on the lake.

127 Queechy Shores Beach, Canaan

$3,595,000

6 Beds ⋅ 5 Baths ⋅ 919651 MLS

A rare offering of scale, privacy, and refinement, Bellavista Country Estate is a magnificent 12,000-square-foot Georgian brick residence set on over 25 secluded acres in the foothills of the Berkshires, perfectly positioned between the Hudson River Valley and the Berkshires. Designed for elegant country living at the highest level, the estate offers six to nine beautifully appointed bedrooms, including three full suites, five bathrooms, multiple fireplaces, a fully equipped eat-in kitchen, and a gracious formal dining room—an exceptional blend of timeless architecture and modern luxury. The grounds are equally compelling, featuring a spacious in-ground pool, a tranquil pond, and direct access to miles of hiking and snowshoeing trails, including those of the Old Chatham Hunt Club. Indoors, amenities rival those of a private resort, with a full gym, game and entertainment room, home theater, and a refined library creating an environment of comfort, recreation, and retreat. A finished attic and an impressive 4,500-square-foot barn with foosball and ping pong provide additional flexible space for leisure and gathering. Fiber-optic internet and a full-house generator ensure seamless modern living, while the estate's thoughtful infrastructure and meticulous maintenance support effortless year-round ownership. Bellavista stands as a premier private estate, offering a rare combination of total privacy, exceptional amenities, and enduring quality. Just minutes from Chatham, Hudson, and Kinderhook—and a short drive to Lenox, Stockbridge, and Great Barrington—the property is surrounded by acclaimed farm-to-table dining, art galleries, organic markets, and the historic Crandell Theater. Easily accessible via the Taconic Parkway or I-87 from New York City, I-90 from Boston, Amtrak to Penn Station, and Albany International Airport, Bellavista is as convenient as it is extraordinary.

147 Rock City Road, Chatham

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