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

$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

$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

$409,000

3 Beds ⋅ 2 Baths ⋅ 999870 MLS

More space and flexibility than you might expect! Set along a quiet country road in the Town of Gallatin, just outside Pine Plains, this 3-bedroom ranch offers approximately 1,860 square feet of living space with a finished lower level, providing plenty of room to spread out, work from home, entertain, or accommodate guests. The main level features hardwood floors, a full bathroom, three bedrooms, and a functional layout that’s ready to make your own. Downstairs, the finished lower level significantly expands the possibilities with additional living and dining areas, a full bathroom, and a second kitchen—known by the owners as the home’s “summer kitchen.” Whether used for recreation, guests, a home office, hobbies, or additional household space, this level gives the home versatility that’s increasingly hard to find. Outside, enjoy a covered patio perfect for relaxing, grilling, and outdoor dining, while the manageable property offers a peaceful country setting surrounded by the natural beauty of the Hudson Valley. Conveniently located near the hamlet of Pine Plains, with easy access to Millbrook, Millerton, Rhinebeck, Red Hook and surrounding communities. If you’ve been searching for a home that offers more usable space, a flexible floor plan, and country living at an approachable price point, 211 Sigler Road deserves a closer look. Come see how much this home has to offer.

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

$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

$450,000

3 Beds ⋅ 2 Baths ⋅ 993638 MLS

Set on a nicely landscaped and private yard ideal for gardening with .65 acres total (an adjacent building parcel of .72 acre can be purchased for an additional amount). This inviting, well-maintained 3-bedroom, 2-bath ranch offers comfort and has a handicap-accessible interior. Features include a living room with a fireplace, lovely wood floors throughout, and a large basement perfect for a workshop, recreation room, or additional storage. The attached garage is accessible through a large sunroom/breezeway for three-season use. Located within 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 kitchen appliances, and central A/C for those hot summer days.

60 Stissing Avenue, Pine Plains

$1,495,000

3 Beds ⋅ 3 Baths ⋅ 987176 MLS

Experience this stunning sanctuary where rustic charm meets modern luxury on over 19 meticulously manicured acres of pure magic! This elevated 3-bedroom, 3-bath masterpiece captures your heart the moment you arrive, drawing you toward an expansive wood deck and a stunning screened-in gazebo with a built-in fire-pit - the ultimate "entertainment perch" for soaking in breathtaking, panoramic valley views. Inside, the home glows with natural light, featuring soaring vaulted ceilings, a gourmet chef’s kitchen with high-end appliances, and a primary suite that serves as a true retreat with its own stone fireplace and oversized closet. A newly reconfigured second bedroom with an adjacent study provides the perfect versatile workspace. The lower level adds even more flair with a sleek kitchenette, media room, a full bath and a new third bedroom. The equestrian facilities includes a 4-stall barn, arena, hay barn, and fabulous riding trails, catering to every horse lover's dream. 3-car heated garage and a powerful 45KW generator. This impeccably maintained estate isn't just a home, it is a move-in-ready lifestyle that is utterly magical. Minutes to the villages of Millerton and Pine Plains. 2 hours to NYC.

617 BEAN RIVER Road, Pine Plains

Start Your Search

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.