Pine Plains Homes for Sale

Pine Plains Homes for Sale

Located in Dutchess County, New York, Pine Plains is a charming town that offers a peaceful and idyllic setting for residents. With a population of just over 2,000 people, this small community provides a close-knit atmosphere that is perfect for those seeking a slower pace of life.

Pine Plains is surrounded by breathtaking natural beauty, with rolling hills, lush green landscapes, and picturesque views at every turn. Outdoor enthusiasts will find plenty to explore, from hiking and biking trails to fishing and boating opportunities in the nearby lakes and rivers.

When it comes to real estate, Pine Plains has a variety of homes for sale to suit different preferences and budgets. Whether you're looking for a cozy cottage, a spacious family home, or a sprawling estate, there are options available to meet your needs. Many of the properties in Pine Plains boast large lots, providing ample space for gardens, outdoor activities, and enjoying the scenic surroundings.

In addition to its natural beauty, Pine Plains offers a range of amenities and conveniences. The town has a charming downtown area with local shops, restaurants, and cafes, providing a sense of community and a place to gather. There are also schools, parks, and community centers, making it an ideal place for families.

If you're looking for a peaceful and close-knit community with beautiful surroundings, Pine Plains is a wonderful place to call home. With its range of homes for sale and its small-town charm, this hidden gem in Dutchess County, New York, is definitely worth considering.

Newest Pine Plains Homes for Sale

$379,000
3 Beds ⋅ 1 Baths ⋅ 1028565 MLS
Attractive 3 bedroom, 1 bath cape cod loaded with recent improvements. Attractive open floor plan includes kitchen w/stainless appliances, granite counters & breakfast bar, which flows seamlessly to living room w/fireplace. Two first floor bedrooms and tile bathroom. Second floor includes generously sized bedroom plus office/den and storage space. Three season front porch is the perfect place to relax. Recent improvements include roof, furnace, water heater, pressure tank and 200 amp electric service. One car garage plus large workshop/studio space complete with insulation & electric and dedicated driveway. All situated on park-like property just minutes from shopping, dining, Stissing Lake and Taconic State Parkway. Attractively low taxes. An opportunity not to be missed.

2795 Church Street, Pine Plains
$429,000
3 Beds ⋅ 1 Baths ⋅ 1026705 MLS
Beautiful, quiet neighborhood with park like setting. Lovely three-bedroom home with landscaped front, back and side yards. Spacious living room flows into quaint dining room with stained pine tongue & groove walls & updated country kitchen with backyard walkout access. Whether you're relaxing in front of the fireplace in the living room or entertaining friends at the backyard fire pit, you will love your new life in beautiful Pine Plains township! Updated kitchen with Farmhouse Sink & Butcher Block counters and shelving. Complete top of the line package of Samsung Wi Fi appliances including Samsung Refrigerator, Stove, Microwave & Washer/Dryer. Hardwood floors throughout. Newer roof and boiler. Brand new finished outdoor shed stays! Short walk to Stissing Pond Rec Beach, ball fields and boat launch. A nature enthusiast's dream with nearby hiking trails throughout beautiful Stissing Mountain as well as Thompson Pond & Twin Island Lake, all just a few minutes’ walk through quiet back roads. Five-minute walk to shops, restaurants, high school, post office, salons, popular Back Bar Beer Garden and world famous Stissing House! Five-minute drive to Taconic Parkway. Central to Rhinebeck, Red Hook, Millerton, Kingston and Great Barrington. Call today!

75 Birch Drive, Pine Plains
$2,475,000
7 Beds ⋅ 6 Baths ⋅ 1022023 MLS
The History: The wonderfully characterful Hammertown was established in 1774, in a small hamlet of millworkers, farmers, and blacksmiths, amidst the lush pastoral landscapes surrounding what would become the town of Pine Plains, New York. The home and its grounds were occupied by only three families across 250 years, each family slowly developing the property to include, in addition to the sprawling main house, beautiful, sweeping trees and gardens, stone walls, a two-hundred-year-old barn that has housed many an ambitious project, and a sweet guest house nestled at the entrance of the land. The Main House: The seat of the property is a traditional colonial farmhouse, tastefully renovated and beautifully envisioned for the current era - while still respecting the home's history as it passed through a quarter of a millennium. Exquisite millwork lines every wall in the home, no less than five fireplaces are peppered throughout, and we mustn’t forget the beautiful, wide-plank wood floors. On the ground floor, you’ll find a large boot room with plenty of storage, a formal dining room, a cozy living room, a wallpapered powder, and the beating heart of the home - the monumental kitchen; a light-filled and dreamy space perfect for entertaining. The second floor has two large bedroom suites with a full bath each, three additional bedrooms, and another full bath. Each bedroom has a subtle but charming color palette, more extraordinary woodwork, and two of the bedrooms have fireplaces. The proportions of the rooms and the layout are well suited to a large family or those with frequent guests, with the two en suites each occupying their own corner of the house, and the three bedrooms and last bathroom in their own wing. The Grounds: Outside, the farmhouse has two ‘faces’ and two beautiful porches. Additionally, a large dining terrace bordered by stone walls sits conveniently off the kitchen. Strolling away from the main house, you’ll find a wrought-iron greenhouse structure and a French parterre garden planted with herbs, lavender, and flowers. The Barn: The Hammertown barn, built in the early 1800s by the founding family of the property, has lived many exciting lives - from being home to elephants from the Barnum Bailey Circus in the early 1900s to its most recent iteration as the main outpost of a beloved furnishings and antiques brand. The barn’s soaring beams and incredible staircase welcome you into the structure, where multiple rooms serve various purposes - including plenty of living space (the perfect place for a home theater), open, sprawling areas with soaring ceilings ideal for hosting large groups, and an abundance of utility, office, and storage space. The barn is fully serviced with electric, air conditioning and heat, and plumbing (including a bathroom). The Guest House: The two-bedroom, two-bath guest cottage was built to elegantly blend with the property's historic character and features multiple fireplaces and detailed millwork. The double-height great room’s arched window floods the house with warm light, and French doors lead to the cottage’s sweet outdoor terrace. The Surroundings: Hammertown is just minutes from Pine Plains, less than fifteen minutes from Millerton and the Connecticut border, and two hours from New York City. The area is defined by some of the most beautiful country landscapes in the region, and is full of hiking trails, thriving local farms, and wonderful small towns and communities. As a marvelously well-serviced compound, Hammertown has incredible potential for those who also wish to explore live-work opportunities, having been home to multiple tasteful commercial ventures and events over the past several decades.

85 Hammertown Road, Pine Plains
$1,695,000
3 Beds ⋅ 3 Baths ⋅ 1010636 MLS
Privately set on 32 extraordinary acres in the heart of Shekomeko, this light-filled country retreat captures sweeping views of Stissing Mountain and the Catskills from nearly every vantage point. A long drive winds through the landscape to a thoughtfully sited three-bedroom, two and a half bath residence featuring vaulted ceilings, expansive windows, a wood stove, and exceptional southern, western, and northern exposures. The 2,250-square-foot home includes a large porch, an outdoor shower, and an attached two-car garage, offering comfortable living amid complete tranquility. Equally compelling is the land itself—an exceptional setting for recreation, privacy, and even a future build for a larger main residence while retaining the existing home as a guest residence. A rare opportunity to own one of Shekomeko's most scenic properties, where dramatic views, acreage, and endless potential converge. 1504 Route 83 is conveniently located; minutes to Mashomack, 10 minutes to Pine Plains and Millerton, and 20 minutes to Millbrook.

1504 Route 83, Pine Plains
$750,000
4 Beds ⋅ 3 Baths ⋅ 1005453 MLS
Light-filled 2006 home blends privacy with effortless convenience. An open-air front porch and a generous backyard frame inviting indoor/outdoor living. Inside, the living room centers on a charming stove, while the chef’s kitchen echoes the home’s airy feel with an island and open plan ideal for entertaining. The first-floor primary suite is a private retreat with a freestanding tub and tiled shower. A powder room and a large mudroom with built-in bench connect to the garage. Upstairs, three additional bedrooms share a full bath with double vanities and a washer/dryer hook-up. The lower level adds flexible space with a recreational room and an office/den. Country living, refined and easy. Set just minutes from the village of Pine Plains & 15-20 minute drive to Rhinebeck and Millerton

82 Maple Hill Lane, Pine Plains
$639,000
3 Beds ⋅ 3 Baths ⋅ 1006576 MLS
Your Lakeside Sanctuary Awaits at 553 Lake Rd in Pine Plains NY. Imagine a life where your mornings begin not with an alarm, but with the gentle song of birds and the sun rising over the glassy waters of Twin Island Lake. Welcome to 553 Lake Road in Pine Plains—a home that doesn’t just offer a place to live, but a feeling of profound peace, warmth, and sanctuary. A Home Infused with Warmth and Light From the moment you step inside, you are wrapped in comfort. Gleaming hardwood floors guide you through a thoughtful layout designed to soothe the soul. The Living Room: Unwind by the crackling fireplace while gazing out at beautiful lake views. The Heart of the Home: An updated, sun-lit kitchen boasts abundant countertop and cabinet space, flowing effortlessly into a lovely dining area. The Sunroom: A bright, incredibly spacious sunroom offers the ultimate spot to curl up with a good book, practice yoga, or simply watch the seasons change. Space to Grow, Create, and Breathe The second floor features two beautifully appointed full baths, ensuring ultimate convenience with 3 bedrooms. Downstairs, a full walkout basement bursts with potential, offering the ideal layout to create an accessory dwelling unit (ADU), a guest suite, or rental space. For the creator or hobbyist, the 2-car heated garage is a dream come true, complete with a workshop and a spacious loft perfect for DIY projects or studio space. Peace of mind is also guaranteed with a whole-house generator. Embrace the Great Outdoors Step outside onto your brand-new Trex porch to sip your morning coffee, breathe in the crisp Hudson Valley air, and feel the stress of the week melt away. With over 3 private acres of your own land, you can hike, explore, and connect with nature right in your backyard. Lake access on your private dock just across the street, kayak or canoe around the lake for an interesting adventure. Looking for a challenge? The breathtaking trails of Mt. Stissing are just minutes away. The Location: A Seamless Escape Located under 2 hours from NYC with a straight, scenic drive up the Taconic State Parkway, this property is incredibly versatile. Whether you dream of a permanent full-time haven, a magical summer retreat, or a lucrative short-term rental/Airbnb, this home is ready to fulfill your dreams. Best of all, you are just 15 minutes away from the historic streets, gourmet dining, and culture of Rhinebeck and Red Hook.

553 Lake Road, Pine Plains
$549,000
2 Beds ⋅ 2 Baths ⋅ 1006574 MLS
Welcome to 559 Lake Road in Pine Plains! Boasting direct views and access to Twin Island Lake, this beautiful property has a proven track record as a highly successful Airbnb. Whether you are looking for a lucrative investment, a dream summer getaway, or a year-round sanctuary, this home has it all. The entire front of the house features stunning, unobstructed lake views. Start your mornings on the covered porch sipping coffee, listening to the birds, and watching the wildlife on the water amidst beautiful perennial flowers. Inside, enjoy a bright, spacious open floor plan ideal for modern living. The layout includes a primary bedroom and bath with plenty of closets, plus a second bedroom and a flexible home office with a large closet, sleeps like a 3 bedroom. Step outside to hike up your own 4 acres of private land, or drive just 15 minutes to enjoy the top-tier restaurants and entertainment in nearby Red Hook and Rhinebeck. All this peace and quiet is located under 2 hours from NYC via the Taconic State Parkway!

559 Lake Road, Pine Plains
$409,000
3 Beds ⋅ 2 Baths ⋅ 999870 MLS
Tucked away on a quiet country road and surrounded by open fields and natural beauty, this charming ranch-style home offers the perfect blend of comfort, flexibility, and peaceful country living. Set on a manageable .25-acre lot this 3-bedroom, 2-bath home features approximately 1,860 square feet of living space with hardwood floors throughout the main level. The fully finished lower level greatly expands the home’s versatility and includes a spacious living room, dining area, full bathroom, and a “summer kitchen,” making it ideal for extended family, guests, or potential mother/daughter living arrangements. Step outside and enjoy the wonderful covered patio area, perfect for relaxing, entertaining, or summer grilling while taking in the peaceful surroundings. Whether you’re searching for a full-time residence, country retreat, or weekend getaway, this inviting Pine Plains home offers warmth, flexibility, and a tranquil setting just minutes from town amenities and outdoor recreation.

211 Sigler Road, Pine Plains
$489,000
4 Beds ⋅ 2 Baths ⋅ 999436 MLS
Step into the charm and character of a bygone era with this spacious early-1900s Colonial-style home located in the heart of the hamlet of Pine Plains. Offering over 3,000 square feet of living space, this 4-bedroom, 1.5-bath residence sits on approximately 0.47 acres and is filled with history, warmth, and timeless architectural details. Once home to both the town pharmacy and library, this unique property blends rich local history with classic Hudson Valley charm. Inside, you’ll find stunning original woodwork and trim, oversized rooms, high ceilings, and beautiful hardwood floors throughout — long protected beneath carpeting for many years and now ready to shine once again. The two-story home offers endless potential for restoration, modernization, or simply enjoying its authentic character as-is. A large barn located behind the home provides excellent storage, workshop space, studio potential, or future creative use. Perfectly situated in the center of town, the property is walkable to local restaurants, the post office, pharmacy, and other village conveniences. Outdoor enthusiasts will appreciate the nearby hiking and biking trails, while commuters and weekend travelers will love being just approximately 30 minutes from both the Amtrak station and the Metro-North Railroad station in Poughkeepsie. Conveniently located between Rhinebeck, Hudson, Millbrook, and Millerton, this home places you in the center of some of the Hudson Valley’s most desirable destinations. A rare opportunity to own a piece of Pine Plains history with space, character, and incredible potential.

7786 S Main Street, Pine Plains
$9,500,000
5 Beds ⋅ 7 Baths ⋅ 996948 MLS
A rare offering of enduring beauty and thoughtful design, this extraordinary modern farmhouse—built in 2019—stands as a true masterpiece set on 52.32 acres of rolling landscape, with sweeping views of mountains, open hills, and the Roeliff Jansen Kill. Spanning 6,875 square feet, the residence blends refined craftsmanship with a warm, livable elegance. Reclaimed 19th-century pine floors with rose head nails run throughout, grounding the home in history while soaring ceilings—including 10’7” in the kitchen and a dramatic 24’6” vaulted, beamed living room—create a sense of scale and light. Walls of windows frame the house and look out onto the established English gardens and beyond to the surrounding hills and orchards. The heart of the home is a remarkable kitchen, complete with its own fireplace, a Lacanche range, and a full wall of glass overlooking the landscape. A separate pantry is equally well-appointed with marble countertops, SubZero refrigerator, and a Miele dishwasher. Every space reflects an uncompromising attention to detail. The main living room is both grand and inviting, featuring exposed beams, a fireplace, built-in library, and French doors that open seamlessly to the outdoors. The primary suite offers a private retreat with a 17’6” vaulted, beamed ceiling, its own fireplace, and a wall of glass capturing the Berkshire Mountains. The spa-like bath includes marble double vanities, a clawfoot tub, and an open shower, complemented by custom-designed closets. A thoughtfully designed greenhouse breezeway connects the main house to a beautifully appointed guest wing. This unique space features soapstone sinks, plaster walls, and French doors leading to a charming courtyard with a fountain made from a 300 year old limestone trough. The guest wing includes a vaulted great room with kitchenette, bedroom, and bath, along with a separate studio or office with woodstove and an additional powder room—ideal for guests, extended stays, or creative pursuits. Additional features include an expansive laundry room with double washers, a dedicated yoga or fitness room, and a mudroom designed for both function and style. Outdoors, the property is equally compelling. There is a heated, saline 18’ x 50’ gunite pool and pergola for dining al fresco. The formal gardens are planted with heirloom roses, towering delphiniums and other classic cottage flowers that bloom the whole season long, and include a white garden that glows in the moonlight. This is a truly bucolic property with dry stonewalls, antique blue stone terraces and a walled vegetable garden just waiting to be planted in the spring. The land itself is rich and vibrant, with an organic orchard featuring multiple varieties of pear, apple, plum and peach, along with blackberry, blueberry, and raspberry bushes. A classic 24’ x 38’ barn with wood sided walls and a separate workspace offers further versatility and space for storing wood and tools. Bordering the property, the Roeliff Jansen Kill provides a peaceful natural edge with trout fishing, complemented by a tributary stream that meets the Roe Jan and picturesque waterfalls. Designed with sustainability in mind, the property incorporates solar energy and electric car charging while seamlessly blending efficiency with luxury living. An exceptional Hudson Valley estate where timeless materials, modern efficiency, and breathtaking natural surroundings come together in perfect harmony.

506 Silvernails Road, Pine Plains
$575,000
7 Beds ⋅ 5 Baths ⋅ 993929 MLS
Stunning renovated Colonial farmhouse set in a peaceful country setting with beautiful pastoral views, just minutes to the Village of Pine Plains. Completely updated in 2020, this spacious home offers the perfect blend of classic charm and modern finishes. The main residence features 4 large bedrooms and 3 full bathrooms, a gracious formal dining room, and a bright, open kitchen with tile flooring and an electric fireplace for a warm, inviting feel. The oversized living room is filled with natural light and highlighted by a beautiful bay window. A finished attic provides additional flexible space, ideal for a home office, studio, or a fun hang out space for teenagers. A standout feature is the separate in-law suite or legal rental, offering 3 bedrooms and 2 full bathrooms with upscale finishes and tile work throughout—perfect for extended family, guests, or income potential. Enjoy quiet country living with easy access to everything the area has to offer—just minutes to Pine Plains and a short drive to Millerton. Spend your weekends exploring local farm stands and farm-to-table dining, walking trails, and scenic hiking. Stissing Lake is nearby for kayaking, swimming, and relaxing summer days. Conveniently located just 10 minutes to Millerton and within 20 minutes to both Red Hook and Rhinebeck. A rare opportunity to own a versatile and beautifully updated property in one of the Hudson Valley’s most charming countryside settings.

80 County Route 7, Pine Plains
$540,000
3 Beds ⋅ 2 Baths ⋅ 993638 MLS
SET ON A NICELY LANDSCAPED AND PRIVATE YARD IDEAL FOR GARDENING WITH 1.37 ACRES TOTAL-(HOUSE ON .65 ACRE AND AN ADJACENT BUILDING PARCEL OF .72 ACRE). THIS INVITING WELL MAINTAINED 3-BEDROOM, 2-BATH RANCH OFFERS COMFORT AND HAS HANDICAP ACCESSIBLE INTERIOR. FEATURES INCLUDE A LIVINGROOM WITH A FIREPLACE, LOVELY WOOD FLOORS THROUGHOUT AND A LARGE BASEMENT PERFECT FOR A WORKSHOP, RECREATION ROOM OR ADDITIONAL STORAGE. THE ATTACHED GARAGE IS ACCESSED THROUGH A LARGE SUNROOM/BREEZEWAY FOR THREE SEASON USE. LOCATED WALKING DISTANCE ONLY MINUTES TO THE TOWN BEACH ON STISSING LAKE AND RECREATION AREA OFFERING SWIMMING, BOATING AND SUMMER CHILDREN'S CAMP. ALSO NEARBY IS STISSING MT. WITH HIKING TRAILS AND THOMPSON POND BIRD SANCTUARY. PINE PLAINS IS A QUAINT VILLAGE IN NORTHERN DUTCHESS COUNTY WHICH IS PRESENTLY KNOWN FOR THE STISSING CENTER FOR ARTS AND CULTURE AND THE STISSING HOUSE RESTAURANT. MOVE RIGHT IN WITH NO WORRIES WITH A NEW ROOF AND KICTCHEN APPLIANCES, AND CENTRAL A/C FOR THOSE HOT SUMMER DAYS.

60 Stissing Avenue, Pine Plains
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