Pine Plains Real Estate

Welcome to Pine Plains, New York – a hidden gem nestled in the heart of the Hudson Valley. This charming town, with a population of just over 2,000 residents, offers a serene escape from the hustle and bustle of city life while still being conveniently located just a short drive from larger urban centers like Poughkeepsie and Kingston.

Pine Plains is characterized by its picturesque landscapes, rolling hills, and lush greenery, making it a haven for nature lovers and outdoor enthusiasts. The town is surrounded by beautiful parks, hiking trails, and scenic vistas, perfect for weekend adventures or peaceful strolls. The nearby Taconic State Park offers a plethora of recreational activities, from hiking and fishing to camping, ensuring there's always something to do in this vibrant community.

The heart of Pine Plains is its charming downtown area, where you'll find an array of local shops, cozy cafes, and restaurants serving up delicious farm-to-table fare. The town hosts various community events throughout the year, fostering a strong sense of togetherness and making it easy to connect with neighbors.

Education is a priority in Pine Plains, with a well-regarded school district that serves the community's families. The town's rich history is reflected in its historic buildings and landmarks, giving residents and visitors alike a glimpse into the past.

Whether you're looking to settle down in a tranquil environment or simply seeking a weekend retreat, Pine Plains offers the perfect blend of rural charm and modern convenience. Come explore this enchanting town and discover the welcoming community that awaits you!

Newest Listings in Pine Plains

$499,000

2 Beds ⋅ 2 Baths ⋅ 1049475 MLS

Welcome to 559 Lake Road in Pine Plains! Boasting direct views and access to Twin Island Lake, this beautiful property has it all, lake and mountain views! 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

$525,000

3 Beds ⋅ 2 Baths ⋅ 1046543 MLS

Charming Cape Cod Retreat on Nearly 6 Acres in Pine Plains. Tucked away on a quiet country road just outside the village of Pine Plains, this charming three-bedroom, two-bath Cape Cod offers the perfect blend of country tranquility, comfortable living, and endless possibilities on nearly six beautiful acres. Welcoming you home with its cheerful yellow exterior, the spacious main level features a comfortable living room, dining area, kitchen, and convenient three-quarter bath. Upstairs, you’ll find three bedrooms and a second full bath, providing plenty of room for family and guests. The walkout basement offers excellent potential and could easily become a creative studio, workshop, hobby space, home gym, or additional living area. A one-car garage with storage below adds even more practicality and space. Step outside onto the generous rear deck and take in the peaceful surroundings. The home is privately set back from the road among mature trees and a shady lawn, while the wooded portion of the property offers something truly special: two streams that converge on the property, creating a picturesque natural setting. Behind the house is a large, sunny open area with plenty of room for gardening, outdoor games, entertaining, or simply enjoying the beauty and privacy of your own country retreat. The location is equally appealing. You’re close to local farms, restaurants, galleries, and music venues, with numerous hiking, biking, and outdoor recreation opportunities within an easy drive. Nearby Millerton, Rhinebeck, and other Hudson Valley destinations offer even more shopping, dining, and entertainment. Located less than a two-hour drive from Manhattan and a short 20 minute drive to the nearest Metro north train station, this property is ideally suited as a peaceful weekend getaway, vacation retreat, or full-time country home. With nearly six acres, beautiful natural features, flexible living space, and a wonderful Hudson Valley location, this is a rare opportunity to create your own private escape in Pine Plains.

404 Schultz Hill Road, Pine Plains

$450,000

1 Beds ⋅ 1 Baths ⋅ 1036155 MLS

Here is a truly exceptional opportunity to enjoy the peaceful lifestyle that comes with lakefront living. Immerse in the sounds of nature, enjoy the changing seasons, spend warm summer days kayaking on the lake, and relax in a setting that feels like a true departure from the everyday. Welcome to your sweet escape at 31 Lake Shore Drive, a charming cottage with an open floor plan and vaulted ceiling that's well suited for year-round living. The flexible layout allows you to use the home as either a one- or two-bedroom, depending on your needs. Imagine enjoying dinner every evening with the lake as your backdrop or unwinding on the rear deck while taking in the beautiful water views. From morning coffee at sunrise to relaxing evenings by the water, this home offers a peaceful place to create lasting memories with loved ones and friends. You will enjoy the benefit a spacious basement and a detached one-car garage, providing plenty of storage for outdoor equipment, seasonal items, or hobbies. Situated on nearly half an acre with mature trees for an added buffer of privacy, there's ample room for outdoor activities, entertaining, gardening, or simply enjoying the open space. Whether you're looking for a full-time residence or a weekend retreat this oasis offers the comfort, charm, and lifestyle that make lakefront living so special. It all awaits you! Make it yours today. Please do not go on the property without a confirmed appointment. Schedule a tour today.

31 Lake Shore Drive, Pine Plains

$359,000

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

$389,900

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

$140,000

1010757 MLS

Ready to build your Hudson Valley dream home? Save numerous months of engineering expense and time with this fully Board of Health Approved 3.45-acre parcel, pre-tested and permitted for a 4-bedroom residence! (Please note: the image of the home in the listing pictures is a POSSIBLE concept created by AI using the land photos.) A rough-cut driveway leads up to a secluded, elevated building site nestled at the top of the hill, offering exceptional privacy, natural breezes, and seasonal Stissing Mountain views. The heavy lifting with county health board approval is already done—making this an ideal canvas for a custom build, country getaway, or spec construction. Located just a short distance from Twin Lakes and the Thompson Pond Preserve, your days can be filled with hiking, kayaking, and taking in the iconic Hudson Valley vistas. Enjoy the local community charm of Pine Plains while staying just a short drive from the cultural hubs of Red Hook and Rhinebeck. From winter skiing to summer river excursions, this property delivers the quintessential upscale country lifestyle. Easy to show—just log and go through showing service.

66 Ryan Road, Pine Plains

$3,950,000

1018855 MLS

An intoxicating opportunity to own a 343 acre swathe of spectacular farmland, proudly eligible for the National Register of Historic Places, that encompasses several impressive barn structures, plus a fully functioning distillery and tasting room. Dutch's Spirits, on Harvest Homestead Farm, is a distillery with a legacy! Harvest Homestead Farm has endless potential. Through the years it has been a productive farm raising turkeys, chickens, pigs and cows, potatoes and corn. It's waiting for someone with vision to perhaps keep the distillery and tasting room going, revive it as a full-time farm, or open a sprawling indoor-outdoor event space. The location is superb: the property neighbors the increasingly popular Mashomack Fish & Game Preserve Club, a 1,900-acre private sporting preserve and social club. The picturesque hamlet of Pine Plains is within a thirty minute drive to the increasingly hip cultural and dining hubs of Hudson and Rhinebeck and only two short hours to Manhattan.

70-98 Ryan 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

$219,000

1009852 MLS

High on the hillside, this untouched 12.78 acre haven presents peace, privacy, and room to dream. The future home site is tucked within mature forest, creating a quiet refuge with the possibility of beautiful seasonal vistas throughout the year. Minutes from downtown Pine Plains and close to the Taconic State Parkway, it strikes the perfect balance between retreat and convenience. A deeded right of way over an existing driveway ensures easy access to this secluded private land parcel.

Mount Ross Road, Pine Plains

$799,000

1008519 MLS

Commercial property with Multi-Use potential in Pine Plains, NY. This versatile commercial property boasts a variety of uses, making it of interest to investors, entrepreneurs and businesses alike. With two apartments, two office spaces, dedicated studio areas and a spacious workshop area with 5 bays with overhead doors. This property offers the perfect blend of residential and commercial functionality with potential for showrooms. Hardwood floors throughout and a new roof. Hard to find commercial property.

2773 Church Street, 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

$975,000

1006565 MLS

The Ultimate Hudson Valley Lakefront Package: Waterfront Mainland Barn, Private Island Glamping Airbnb, Ease Side Lake Access Land & Endless Views! Welcome to a truly unprecedented real estate opportunity on the pristine waters of Twin Island Lake in beautiful Pine Plains, NY. This isn’t just a land listing; it is an extraordinary three-parcel package deal that blends rustic charm, income potential, and the kind of absolute tranquility that is rare to find. The Mainland Sanctuary (0.85 Acres) Step onto nearly an acre of gorgeous lakefront property, beautifully cleared all the way down to the water's edge. The centerpiece of the mainland is a solid, character-filled barn featuring a spacious loft that is just waiting for your vision. With electric already available, this loft could easily be transformed into a charming, creative living space, a writer's retreat, or the ultimate lakeside clubhouse. Outside, your private waterfront oasis is already set up for perfect summer days and cozy autumn nights. Launch a kayak from your floating dock, host a lakeside lunch at the picnic table, or unwind by the fire pit. The panoramic views across the water to the majestic Stissing Mountain rising in the background will quite literally take your breath away. Your Own Private Island Retreat As if the mainland weren't enough, this sale includes a literal dream feature: ownership of one of only two private islands on Twin Island Lake! Currently operating as a highly successful Airbnb, this island defines "glamping at its finest." It offers the ultimate off-grid luxury experience, fully equipped with: A cozy setup featuring a warming gas fireplace Covered kitchen area Raised Platform with Safari tent and bed An outdoor fire pit for star-gazing On-site toilet and a refreshing solar shower Whether you choose to keep running it as a lucrative short-term rental or reserve it entirely as your own secret hideaway, this island is a showstopper. Versatility & Nature at Your Doorstep To round out this incredible package, an additional 0.01-acre lake access property is included, offering even more versatility for layout and usage. This property is a haven for local wildlife. Spend your mornings sipping coffee while watching elegant swans, geese, and ducks glide across the glassy water, and spot turtles sunning themselves on the logs. It is a peaceful world entirely your own. The Location While you will feel a million miles away from the hustle and bustle, you are never isolated. This slice of paradise is located just 15 minutes from the vibrant, historic towns of Red Hook and Rhinebeck, giving you effortless access to fine dining, boutique shopping, farmers markets, and the Amtrak station. A short ride up the Taconic, this is a fast trip to escape the hectic pace of the NYC for the weekend or a summer of relaxation. Property Highlights: Total Package: 0.85-acre lakefront parcel + .25-acre Private Glamping Island + 0.01-acre lake access parcel. Structures: Barn with loft (electric available), floating dock, fire pit. Island Amenities: Turn-key Airbnb Glamping setup with gas fireplace, solar shower, and toilet. Views: Unobstructed lakefront and Stissing Mountain views. Don't miss out on one of the most unique waterfront offerings the Hudson Valley has to offer. Bring your dreams, your boat, and your sense of adventure!

71 Lake Shore Road, Pine Plains

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