$529,605Average Value$343Average Price per Sq Ft18Homes For Sale
Pine Plains: a charming, rural small town in the Hudson Valley
Pine Plains is a quintessential small town located in New York’s rural Dutchess County; one of the closest major cities, Hudson, takes around 35 minutes to drive to. Although people have lived here for centuries, the area has experienced rapid growth over the last couple of decades, thanks to the rise of local outdoor tourism and increased options for remote work. Pine Plains is also home to notable attractions, including the Stissing House restaurant and its affiliated establishments.
Housing options range from starter homes to luxury estates
You can find a wide variety of housing options and architectural styles throughout Pine Plains. “It’s very much a mix of homes here,” says Ann Stettner, an experienced Realtor with Neil Charles Real Estate who sells homes across the Hudson Valley. “You have your more modest houses—your ranches and cottages—then you have mid-tier options, the ones with more space, and then you have high-end homes that can cost up into the multi-millions. You’ve got people here buying starter homes and people buying homes that have been in their family for generations. It’s also both a second home community and a place full of full-time residents—a lot of people came to live here full-time during Covid and never left.” Most single-family homes range from $270,000 for fixer-uppers to about $850,000 for move-in-ready homes, although some rural estates on multi-acre properties have sold for as much as $8.3 million. Stettner says that the diversity in housing options is one of the main draws here and that locals frequently shut down plans for large suburban developments to preserve Pine Plains’ architectural character and small-town charm.
Outdoor activities from hiking to skiing draw residents and visitors
Pine Plains is a growing destination for outdoor recreation in the Hudson Valley—with nearby lakes, state parks and forests, residents and visitors can find plenty to do in the immediate area. “People go hiking in the summer and skiing in the winter, and biking and cycling are big year-round,” Stettner says. For unobstructed views of the town and the surrounding area, you can hike up to the Stissing Mountain Fire Tower. Fishing enthusiasts can head to the Mashomack Fish & Game Preserve, which encompasses several bodies of water, including Halcyon Lake and Stissing Pond. Pine Plains has a local youth baseball and softball program and hosts games at Stissing Lake Park.
Church Street offers a mix of eateries for every taste
Church Street in Pine Plains offers multiple dining choices for both locals and visitors, but it hasn’t always been this way: “Pine Plains used to be a sweet little country town. There wasn’t a lot there, but then some wealthy people bought some parcels of land, and they decided they wanted some restaurants, some coffee shops, etc. So now you have renowned places like Stissing House right there in a small town,” Stettner says. Dining spots in Pine Plains include:
Stissing House, a historic American tavern housed in a Colonial-era building
Spud Shack, a grab-and-go fast food joint with a retro 1950s design
Tower Pizza, a local pizzeria with outdoor seating
Storybook Café, a breakfast and lunch spot with shelves full of books for patrons to read
For fresh produce, people can stop by one of Pine Plains’ many local farm stands. Stettner also notes that larger grocery stores and supermarkets are within 10 minutes of town.
Local shops and boutiques give Pine Plains a small-town feel
Most of the shops in Pine Plains are locally owned, such as flower shops, bookstores and clothing boutiques. The Stissing Center for Arts and Culture serves as both a community hub and an arts organization, offering a variety of local events and activities, including live music performances and theatrical productions.
Pine Plains Central School District includes three schools
Pine Plains has its own school district—the Pine Plains Central School District—serving local students from kindergarten all the way through 12th grade. The district is made up of three schools, all of which receive moderate ratings: Cold Spring Early Learning Center, Seymour Smith Intermediate Learning Center and Stissing Mountain Jr./Sr. High School. The closest higher education institution is Bard College in Annandale-On-Hudson, just under 17 miles west of town.
Driving distances to Millerton, Rhinebeck and regional airports
Route 199 runs through Pine Plains and connects to other regional thoroughfares, including the Taconic State Parkway to the west and Route 44 to the east in Millerton. “The closest towns would be Millerton, about 10 minutes away, and Rhinebeck, which is probably a 10- to 15-minute drive away, so they’re kind of equidistant,” Stettner says. “Pine Plains is centrally located in a way; it’s beautifully rural, and you feel that isolation when you’re there, but civilization really isn’t far away at all.” There is no public transit system in Pine Plains. The closest airport is Hudson Valley Regional Airport outside Poughkeepsie, approximately 40 minutes away.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
View GreatSchools Rating Methodology
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Crime and Safety
1 - Low Crime, 10 - High Crime
Pine Plains
US
Homicide
1
4
Sexual Assault
1
4
Assault with Weapon
1
4
Robbery
1
4
Burglary
3
4
Motor Vehicle Theft
2
4
Larceny
1
4
Crime Score
1
4
Source: WhatIsMyCrimeRisk.com
Pine Plains Demographics and Home Trends
On average, homes in Pine Plains, Millerton sell after 76 days on the market compared to the national average of 56 days. The median sale price for homes in Pine Plains, Millerton over the last 12 months is $537,500, down 9% from the median home sale price over the previous 12 months.
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
Rarely does a property of this caliber become available. Spanning approximately 234 acres across two contiguous parcels (162 acres and 71.5 acres), this exceptional offering features productive hay and corn fields, rolling farmland, mature woodlands, and breathtaking long-range views of the Taconic Mountains and Catskills. Multiple elevated building sites provide the opportunity to create a
Sweet and solid, one level Ranch home on a bucolic setting with rolling hills and farmland framing your homestead. Walk into your open living room with built ins and lovely bay window. Through to the dining room and eat in kitchen, perfect for hosting with ease. Sliders to the back covered porch off the dining room allows for al fresco living and enjoying your coffee while watching the sunrise.
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
Perched high on 5.32 private acres with breathtaking, distant panoramic views of the Taconic Range and Berkshire Mountains, this contemporary home has been completely transformed by a top-to-bottom renovation. Seamlessly blending chic modern upgrades with dramatic architectural bones, this turn-key residence offers utmost privacy on a scenic country lane, yet still provides incredible
Looking for a property that offers an opportunity for a homestead lifestyle in the Hudson Valley? Situated in the Town of Pine Plains, this early colonial farmhouse is now offered for sale on 15+ acres. Appointed with wide-plank floors, the main level features sun-lit, well-proportioned rooms. On the second floor, there is a primary bedroom with a dressing room, 3 additional bedrooms, an office,
Secluded 2BR/2BA RANCH w/2 large decks, all wood floors, ornamented wood siding painted + detached 2 car garage on 7 acres. Parcel is subdividable in Hamlet zone. New well installed. Also available with 8 additional acres for 565000 or with 12 acres (3 building lots) for 689000.
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
Cedar Ridge Farm is a premier 246-acre equestrian estate set in the heart of Dutchess County, offering exceptional land quality, extensive infrastructure, and the rare scale required for a top tier equestrian operation or private country estate. The farm encompasses approximately 110 acres of fenced paddocks supported by thoughtfully designed facilities that ensure efficiency, functionality, and
Nestled on a country road in West Pine Plains, the Historic Hanlon Hill Farmstead offers a rare opportunity to own a piece of history. This 87-acre property, spanning five parcels, has been in the Hanlon family for six generations. The centerpiece is an 1840s eyebrow colonial home, set back from the road for ultimate privacy. As you enter the farm, you'll pass a serene pond and a charming
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
Great opportunity for 1 residence (property is in Hamlet Zone and possibly subdividable). Approved Septic design and existing shared driveway (probably 10 feed are shared). Newly renovated home on North. Adjoining 8 acre vacant lot to the South available for 199,000. Both lots for 300,000. Owner financing possible.
Discover effortless living at Stissing Farms Townhomes, where modern comfort meets small-town charm. These beautifully designed homes feature open floor plans, two spacious bedrooms, two full baths, full basements, and one-car garages—thoughtfully crafted for both style and convenience. Enjoy high ceilings, modern kitchens, in-unit laundry, central air, and a private ensuite primary bath that
A Home with a view of Stissing Mountain! Enjoy gorgeous sunsets all year long from your front door. Spacious raised ranch on a level lot is move-in ready. Main floor has an open floorplan and wood floors throughout. The light filled kitchen with a nice sized island has new granite countertops. The storage room next to the kitchen could easily become a walk-in pantry. Primary bedroom has en-suite
SUMMER RENTAL. Available July & August for 35,000 per month. Overlooking 119+ acres of rolling hills this property offers an ideal setting for the perfect country lifestyle. The spacious country house with seven en-suite bedrooms and has been fully customized with generously sized rooms, crown moldings and beautiful flooring throughout. Outdoor features include a large bluestone terrace, heated
Discover effortless living at Stissing Farms Townhomes, where modern comfort meets small-town charm. These beautifully designed homes feature open floor plans, two spacious bedrooms, two full baths, full basements, and one-car garages—thoughtfully crafted for both style and convenience. Enjoy high ceilings, modern kitchens, in-unit laundry, central air, and a private ensuite primary bath that
Discover effortless living at Stissing Farms Townhomes, where modern comfort meets small-town charm. These beautifully designed homes feature open floor plans, two spacious bedrooms, two full baths, full basements, and one-car garages—thoughtfully crafted for both style and convenience. Enjoy high ceilings, modern kitchens, in-unit laundry, central air, and a private ensuite primary bath that
Come home to the Lake !! Nicely renovated 1 Bedroom Apartment. Also has a Den/Office. All new Kitchen & Bath. Includes new dishwasher, new state-of-the-art gas range, new refrigerator & microwave. All new bathroom fixtures and tiled floor. Situated up a hill with a great view of the beautiful Twin Island Lake - some lake rights included. The fishing is excellent! Landlord pays heat, hot water,
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