$523,250Average Value$400Average Price per Sq Ft9Homes 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 122 days on the market compared to the national average of 53 days. The median sale price for homes in Pine Plains, Millerton over the last 12 months is $575,000, up 54% from the median home sale price over the previous 12 months.
Modern Minimalist Masterpiece on 19 Bucolic Acres in Dutchess County. Welcome to a rare offering in the heart of the Hudson Valley, where striking modern architecture meets timeless pastoral beauty. Completed in late 2024, this extraordinary estate sits on over 19 acres of flat, fenced farmland at the picturesque intersection of Bethel Cross and Carpenter Hill Road. Perfectly sited on a
Public Remarks: One of the most breathtaking vistas in the region, this 157-acre parcel crowns a private site at 1,250 feet, with commanding views to the Catskills. Offered for the first time in generations, this legacy property is paired with an adjacent 71.5-acre parcel, once a distinguished family farm. The panoramic vista from every knoll enjoys the unspoiled countryside extending to the
Sensational vistas of the stunning and unspoiled countryside extending to the Taconic's to the East and from a hidden knoll with an elevation of 1,250' there is a magnificent private setting with incredible Catskill views. The main parcel of 157 acres is offered for the first time in generations and that parcel adjoins a 71.5-acre parcel, this was a family owned and operated farm. Both properties
Every once in a while, an exceptional opportunity like this turns up. Located in rural Pine Plains this 5.02-acres is a pair of vacant building lots that offers privacy and serenity. These two contiguous parcels are completely wooded and accessed via a shared driveway. Your dream home is only limited by your imagination these parcels will invigorate that imagination. The Town center and the
Welcome to the Historic Town of Pine Plains! This completely renovated three bedroom home on a quiet country road will delight and intrigue you. The home dates back to the early 1900's and some of the original characteristics have been left in tact. This is most assuredly Old World Charm meets Modern Convenience. One bedroom on the first floor attached to the Sunroom, will work for a great Flex
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,
Adorable 3-bedroom ranch ready for you to move in. Ideal for First-time home buyers or anyone tired of paying rent. Bright eat in kitchen, living room with fireplace. door that leads out to large back yard. Close to schools, Village of Pine Plains and TSP. County living at its best. Additional Information: HeatingFuel:Oil Above Ground,
Enjoy nature on your own 43 scenic acres located on Hicks Hill Road and additional access from Knob Hill Road, which is across from apprx 600 acres of protected land that can not be developed offering exceptional long term privacy. A versatile existing barn provides potential for a variety of uses. With over 1,400 feet of road frontage on Hicks Hill Road and electric available on the property,
Great opportunity for 1 residence (property is in Hamlet Zone and possibly subdividable). Approved Septic design and existing shared driveway. Newly renovated home on North. Adjoining 8 acre vacant lot to the South available for 199,000. Owner financing possible.
Build your dream home in the heart of Pine Plains, surrounded by nature, history, and vibrant Hudson Valley living, on this exceptional 3.45 Acre elevated homesite, Board of Health approved for a 4-bedroom residence, with sweeping views of majestic Stissing Mountain. This remarkable parcel offers the perfect blend of tranquility, natural beauty, and convenience, presenting a rare opportunity to
Attention investors & contractors! 4 Bedroom, 2.5 Bathroom Two Family Ranch on 2.4 acres in T/Pine Plains! Sold as-is. Buyer to pay NYS and any local transfer taxes. Offers with financing must be accompanied by pre-qual letter; cash offers with proof of funds. **Please see agent remarks for access, showing instructions and offer presentation remarks.**
You wanted charm? You got it! This vintage 1903 village home in Pine Plains, NY formerly served as both the town pharmacy and library, and many of the bookshelves and all the quaint apothecary drawers remain intact. The large 3000sq foot home on a nicely landscaped yard of nearly a half an acre is filled with period details: wooden moldings, original door knobs and intricate iron hardware, a
Live the way you've always wanted without compromising style or quality. At Stissing Farm Townhomes, our apartment residences are designed with you in mind. Now you really can have it all . . . lifestyle included.Pine Plains was named One of the Best Small Towns in New York by !
Welcome to 119 Righters Corners Rd, a charming and well-maintained two-bedroom, one-bathroom home located in the scenic Town of Pine Plains, New York. This inviting residence features hardwood floors throughout, creating a warm and cohesive living space. The kitchen and bathroom have been tastefully renovated, offering modern finishes while maintaining the home’s comfortable, classic feel. The
Welcome to The Lake Cottage – A Rare Seasonal Retreat on Twin Island LakeDiscover The Lake Cottage, a one-of-a-kind, fully furnished seasonal escape on the shores of Twin Island Lake. This private lakefront compound offers a tranquil and inspiring setting, making it the perfect getaway for artists, writers, creatives, or anyone in search of rest and renewal.Nestled behind lush, mature
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