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Pine Plains NY Real Estate & Homes for Sale

34 Properties Found

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$3,995,000

476 Carpenter Hill Rd Pine Plains, NY 12567

MLS: 885787 Photos
Beds:
4
Baths:
4.00
Sq.Ft.:
4,103
Status:
NEW LISTING
MLS#:
885787
Type:
Single Family
Lot size:
19.07 Acres
Year built:
2023
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: William Raveis Lifestyles Rlty 860-868-0511
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ADDITIONAL INFORMATION

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 south-facing rise along the Shekomeko Creek, this newly constructed home is a serene, sophisticated sanctuary just two hours from New York City. A bold fusion of modern, industrial, and eclectic design, the residence offers over 4,700 square feet of light-filled, open-concept living on one level, including 3,057+/- sq ft main house, a stunning 1,046+/- sq ft attached greenhouse-conservatory that brings year-round indoor-outdoor living to life and a 1,423 sq ft +/- heated garage/studio/guest apartment. Every detail was curated with intention; from yaki sugi siding and a metal Kemper roof to polished concrete floors and walls of glass that frame unspoiled views of nature. The heart of the home features a bespoke chef's kitchen with live-edge shelving, custom cabinetry milled from trees on the property, concrete countertops, a butler's pantry, and a beverage bar. Double primary suites offer en suite wood burning stoves, spa-like baths with cast iron tubs, Italian tile, and handcrafted metal vanities. Both are complimented by airy bathrooms with natural light and industrial fixtures.A gas fireplace in the ample living room, vaulted ceilings, clerestory windows, and art lighting throughout create a harmonious blend of warmth and style. This is a home designed not just to live in, but to live fully. Outside, the entire 19-acre estate is bordered by classic white 4-board oak fencing, ensuring both privacy and visual continuity. A one-acre, 10-foot-deep pond and expansive flat pastures make this a dream property for equestrians, polo enthusiasts, hobby farmers, or anyone seeking a deep connection with the land. Zoned as a horse farm within an agricultural district, it offers rare potential for animal lovers and breeders alike. Car collectors and creatives will appreciate the oversized, fully heated garage and studio space outfitted with track lighting, storage, and the flexibility to serve as an art gallery, workshop, or one-bedroom apartment. With a 3,000 sq ft unfinished basement, covered porches, multiple patios, and estate management partners already in place, the property is as functional as it is inspiring. Additional features include an Endless Pools heated performance pool in greenhouse. The home has a sustainable, passive solar design and was constructed to allow for a future living roof/rooftop deck. New well, septic, and underground utilities. Energy-efficient systems throughout. Surrounded by horse farms and wildlife. Just minutes from the town center and Mashomack Polo Club. Whether you're an artist, gardener, equestrian, or collector, this unique Hudson Valley estate delivers a modern lifestyle without compromise. Offered for the discerning buyer seeking privacy, sophistication, and natural beauty in equal measure.

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$749,000

37 Stissing Mountain Dr Pine Plains, NY 12567

MLS: 883517 Photos
Beds:
2
Baths:
2.00
Sq.Ft.:
1,624
Status:
Active
MLS#:
883517
Type:
Single Family
Lot size:
6.91 Acres
Year built:
2024
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Compass Greater NY, LLC 838-877-8283
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ADDITIONAL INFORMATION

Welcome to 37 Stissing Mountain Drive. Perfectly nestled on 6.9 acres of peaceful woodland, this newly built 2-bedroom, 2-bath home is a modern sanctuary that beautifully balances simplicity, sustainability, and style—just minutes from the heart of Pine Plains NY. Inside you will find a sun-filled, open-concept living space with soaring 22-foot vaulted ceilings that frame sweeping views of the surrounding forest. Clean architectural lines and radiant heat throughout the polished concrete floors create a warm, minimalist backdrop that’s both inviting and efficient year-round. Complete with a first floor bedroom and bath, home office space, and a generous lofted primary you have plenty of options for you and your guests. Expertly designed and constructed for low-maintenance living without compromise, the home was constructed with longevity in mind—featuring high-performance systems and durable materials that require little upkeep. Whether you're seeking a full-time residence or a weekend escape, this home offers a seamless connection to nature and ease of everyday living. Outdoors, you’ll find a landscape that’s equal parts wild and welcoming. There’s ample room to garden, build trails, or simply wander under the trees. Cozy up around the firepit under a blanket of stars or take a peaceful walk through your own private woods. Located in one of Dutchess County’s most scenic corners, Pine Plains is known for its natural charm, rolling hills, and small-town soul. Just two hours from NYC, and close to Rhinebeck, Millerton, and the Taconic Parkway, it’s also home to beloved local gems like Stissing House, Chaseholm Farm and Dutch’s Spirits. A timeless Hudson Valley escape with all the modern comforts already in place

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$595,000

57 Myrtle Ave Pine Plains, NY 12567

MLS: 884042 Photos
Beds:
4
Baths:
2.00
Sq.Ft.:
2,605
Status:
Active
MLS#:
884042
Type:
Single Family
Lot size:
0.63 Acres
Year built:
1860
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Thomas Zengen 845-224-8005
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ADDITIONAL INFORMATION

Beautiful Two Story, 4BR/2BA corner lot home with mountain views & quick walk to post office, shops, Stissing Lake & Stissing Mountain hiking trails. Experience the wonderful life of beautiful Pine Plains living! Wonderful large front, side & back yard on quiet sought after Myrtle Ave. Lovely front porch to sit & enjoy the scenery or head into the private back yard for a BBQ. Walk to school, post office & shopping in a minutes time! Large windows throughout brings bright, sunlit rooms & atmosphere. Beautiful Hemlock hardwoods throughout. High 10 foot ceilings, Double living rooms or Living room with attached library flow into formal dining room with attached sunroom. First floor bedroom. Large bedrooms on 2nd level. Separate den/office on 2nd floor. Many new upgrades including plywood, siding, sheathing, roof, shingles, insulation, etc. Washer & dryer in basement with second washer/dryer hookups in 2nd level bedroom. Gas stove & marble countertops in kitchen. Decorative fireplace in 2nd living room/library. Detached barn garage structure with workshop. Call today for a tour & view this beautiful home in one of the Hudson Valley's most sought after townships around!

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$8,475,000

367 Prospect Hill Rd Pine Plains, NY 12567

MLS: 882588 Photos
Beds:
6
Baths:
8.00
Sq.Ft.:
12,418
Status:
Active
MLS#:
882588
Type:
Single Family
Lot size:
170 Acres
Year built:
1991
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Houlihan Lawrence Inc. 845-677-6161
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ADDITIONAL INFORMATION

First time on the market! This magnificent 170-acre Modern Adirondack-styled estate near Millbrook, designed by architect Lloyd Taft, features a main house and three elegant guest cabins. Built by a third-generation builder of camps in upstate New York and the Thousand Islands, the cabin serves as the centerpiece of the compound. Meticulously maintained and tailor-made for year-round recreation, the property offers spectacular panoramic views of the Catskills and Taconic Hills from sunrise to sunset. With hand-hewn luxury reminiscent of Ralph Lauren’s aesthetic, the log-and-stone main residence features wraparound porches, a great room with a dramatic stone fireplace, a chef’s eat-in kitchen with Sub-Zero and Wolf appliances, a media room, a billiard room, and a luxurious primary suite with a fireplace and sunset terrace. The main house can accommodate ten people. Each of the three guest cabins, connected by a breezeway, features a fireplace, stone shower, kitchenette, and porch. In total, the guest quarters can accommodate twelve. Incredible amenities include a triple-height sports barn with an indoor sport court featuring pickleball, basketball, badminton, volleyball, a full gym, and a bonus arcade area. In addition, the sports barn can easily be converted into a large-format home theater. Additional outdoor features include an elevated paddle/pickleball court, a fillable freshwater swimming hole, a stocked pond, a full football/soccer field, six heated wildlife-watching perches, hiking trails, and an orchard with apples, peaches, sweet and sour cherry trees, blueberries, raspberries, and a cutting garden with a firepit. The compound also includes a party barn, a fish and game room, a separate office, and a grassy courtyard for croquet, bocce, and picnics. Ninety acres are professionally farmed by a local farmer. Ideally located close to Metro-North, Mashomack Preserve and Polo Club, Tamarack Preserve Club, and Orvis Sandanona, as well as the towns of Millbrook, Millerton, Pine Plains, Rhinebeck, and more. Unmatched privacy and resort-style living in the heart of the Hudson Valley.

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$875,000

7668 Route 82 Pine Plains, NY 12567

MLS: 880499 Photos
Beds:
4
Baths:
2.00
Sq.Ft.:
2,709
Status:
Active
MLS#:
880499
Type:
Single Family
Lot size:
15.33 Acres
Year built:
1900
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: George T Whalen Real Estate 845-677-5076
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ADDITIONAL INFORMATION

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, and a full bathroom off the hallway. There is also a walk up attic. Off the rear of the house, there is a workshop and several period barns. The property consists of two parcels; the house and barns on 10 acres plus an additional contiguous 5 acre vacant parcel. The land is lovely, with rolling hills and views of Stissing Mountain. This farm is less than two hours from New York City, convenient to Mashomack Preserve and minutes to the Pine Plains town center where you will find shops and restaurants, including the Stissing House Restaurant as well as the Stissing Center for Arts & Culture. For outdoor adventuring, nearby Stissing Lake and Stissing Mountain Hiking Trails are sure to please. A wonderful property for a new owner to bring back to life.

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$900,000

2365 Route 83 Pine Plains, NY 12567

MLS: 883841 Photos
Beds:
5
Baths:
3.00
Sq.Ft.:
2,413
Status:
Active
MLS#:
883841
Type:
Single Family
Lot size:
160.69 Acres
Year built:
1830
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Rich Brenner Realty, LLC 914-456-4691
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ADDITIONAL INFORMATION

Rare opportunity to own 160 breathtaking acres in the heart of Pine Plains, featuring rolling fields, wooded terrain, and scenic wetlands. Anchoring the property is an antique farmhouse awaiting restoration, set within a 7 plus acre residential area offering privacy and pastoral charm. Most of the property is protected under a conservation easement, preserving the natural landscape while allowing for agricultural use, trails, and recreational enjoyment. In addition to the farmhouse site, a second designated building envelope along Route 82 provides future development potential. Ideal for conservation-minded buyers, equestrian estates, or those seeking a generational compound in a sought-after Hudson Valley location. Convenient to Pine Plains center, Stissing Mountain trails, and within easy reach of Rhinebeck, Millerton, and the Wassaic train to NYC.

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$775,000

1220 Hunns Lake Rd Pine Plains, NY 12567

MLS: 881059 Photos
Beds:
4
Baths:
2.00
Sq.Ft.:
1,344
Status:
Active
MLS#:
881059
Type:
Single Family
Lot size:
1.52 Acres
Year built:
1920
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Compass Greater NY, LLC 914-238-0676
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ADDITIONAL INFORMATION

1220 Hunns Lake Rd is perfect as a full-time family home or a weekend escape, ideally located for both tranquility and convenience. This charming early 1900's farmhouse in the serene Shekomeko Valley offers 4 bedrooms, 2 bathrooms, and 1,344 square feet on 1.52 bucolic acres. The property boasts views of the surrounding countryside and stunning sunsets. Enter the home through the light-drenched wraparound enclosed porch: on the first floor, find a large mudroom adorned with custom wallpaper, full bath, and a spacious kitchen that's wonderful for entertaining. A large dining and living room with wood burning fireplace has French doors that open onto a patio - perfect for al fresco dining. Off of the living room is a cozy family room. Upstairs, you'll find 4 bedrooms and a full bathroom. Original and reclaimed hardwood floors throughout this updated, light-filled country home, which offers Central AC and basement laundry. Outside, a vegetable garden, clawfoot tub, roses, peonies, and plenty of space to picnic with a view. Nature lovers will appreciate the short walk to Wethersfield, where you can explore some of the most beautiful walking trails in the Hudson Valley, while the property itself is landlocked by the Dutchess Land Conservancy, ensuring privacy and natural beauty. Enjoy your own private trail through the woods to a magical clearing with 360 degree Hudson Valley views. Most desirable location for anyone seeking Hudson Valley landscape with convenience to surrounding areas: 2 hours from Manhattan, 10 minutes from Stissing House, 15 minutes from Millbrook, Millerton, and Amenia, 20 minutes from Sharon, CT and Rhinebeck, and minutes from Dutchess Day School, Indian Mountain School, and the prestigious Millbrook School. Available for viewings today!

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$925,000

1388 Route 83 Pine Plains, NY 12567

MLS: 878879 Photos
Beds:
4
Baths:
5.00
Sq.Ft.:
3,000
Status:
Active
MLS#:
878879
Type:
Single Family
Lot size:
0.36 Acres
Year built:
1880
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Houlihan Lawrence Inc. 845-876-4443
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ADDITIONAL INFORMATION

This c. 1880 three-story farmhouse seamlessly blends historic charm with modern luxury, meticulously cared for and thoughtfully curated to offer both timeless elegance and contemporary comfort. Step inside and be greeted by the inviting, light-filled living room. This spacious area exudes classic sophistication, centered around a warming wood-burning fireplace and boasting large windows that open to the serene backyard. Adjacent, the open-concept kitchen and dining area — a collaboration between the homeowners and renowned designer Jean Stoffer— forms the heart of this historic home. Gorgeously renovated in 2022, it's flooded with natural light from generous windows and French doors, showcasing luxury fixtures, handmade tile, premium hardware, and built-in Sonos speakers throughout. An inviting library/office and a convenient powder room thoughtfully complete the main level. Upstairs, two bedrooms, each with an en-suite bathroom, grace the second floor. The primary suite is a luxurious retreat featuring an expansive bedroom complete with a gas fireplace, an additional sitting area, and smart lighting. Its attached bathroom boasts a handcrafted glass shower enclosure, radiant heat, and stunning nature views while maintaining privacy. The light-filled third floor presents two additional bedrooms, each with its own en-suite bathroom, plus an adaptable open living space – perfect for a playroom, home gym, or additional living area. In 2021, all new windows, hardware, and solid wood doors were installed, complemented by refinished or new hardwood floors throughout for a seamless flow between levels. All major home mechanics have been upgraded for maximum energy efficiency, and for ultimate security and comfort, a whole house generator is included. Beyond the home, a magnificent 900 sq ft bluestone patio with a pergola, gas fire pit, and a barrel sauna provide exceptional outdoor living. This exquisite property is enveloped by conservation land that provides unobstructed views across a vast natural landscape and safeguards against future development. The hamlet of Shekomeko is a beautiful slice of the Hudson Valley, where the contours of the land and layers of history create a setting rich in natural and cultural heritage. While offering the tranquility of a secluded retreat, Shekomeko remains conveniently accessible to vibrant towns like Hudson, Rhinebeck, and Great Barrington, with easy rail access to New York City. This makes it an ideal haven for discerning buyers seeking the ultimate upstate escape. OPEN HOUSE SUNDAY JUNE 29th 1-4:00 pm

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$899,000

198 Sigler Rd Pine Plains, NY 12567

MLS: 857938 Photos
Beds:
5
Baths:
4.00
Sq.Ft.:
2,714
Status:
Active
MLS#:
857938
Type:
Single Family
Lot size:
17.9 Acres
Year built:
1989
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: BHHS Hudson Valley Properties 845-876-8600
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ADDITIONAL INFORMATION

This architect designed and custom built passive solar home and guest house is sited privately on 17.90 acres with panoramic views of the of the eastern valley plains to Stissing Mountain and beyond. The tree lined driveway leads you to both houses that sit high on the land, facing south over looking the property fields & pond. Perfectly sited for the passive solar design and the solar panel system. The property is surrounded by large properties hence the views of the valley, farms and mountains from this property have not changed in 50 years! This octagon shaped home was designed to capture the views with windows on all the walls to capture the light and views. The main house has 2008 sq ft all above ground. The upper living level features open floor plan with vaulted ceilings, walls of windows, skylights and a center floor to ceiling Jotul wood burning stove fireplace. The living room, kitchen (granite counter tops, wood cabinets, stainless steel appliances, pantry), dining and a half bathroom room are all centered around the large chimney with an open spacious design to capture the spectacular views. The dining room area has sliding glass doors that lead to 336 sq ft of tiered decking with a 6 person spa hot tub, dining, siting & fire pit areas all with views. The lower level that has 4 bedrooms (including a primary suite), 2 full bathrooms, laundry & utility room. The lower level rooms have access to the patio sitting area and the spectacular views from all the rooms. The detached 706 sq ft guest house and 2 car garage also has amazing views and southern eastern exposure. The upper level of the guest house has a large living room with wood burning stove fireplace, full kitchen/dining area, 1 bedroom, a full bathroom, Oak floors and a large deck. The lower level has 2 garage bays perfect for cars, tractors or storage. There are also two large sheds, one with a finished interior currently used as a music studio. The property is located on one of the most scenic country roads only 80 miles up the Taconic State Parkway from New York City. This is a very unique, one of a kind property to enjoy a tranquil setting, nature, privacy and the panoramic views. Perfect weekend retreat or full-time home. Please see 3D tour and floor plans for more detail. An additional adjoining 8.1 mountain top acres with 360-degree views will also be available to purchase.

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$589,000

Rd Pine Plains, NY 12567

MLS: 875541 Photos
Beds:
2
Baths:
2.00
Sq.Ft.:
1,336
Status:
Active
MLS#:
875541
Type:
Single Family
Lot size:
15 Acres
Year built:
1968
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Barns and Farms Realty LLC 518-822-0226
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ADDITIONAL INFORMATION

PINE PLAINS 2-3 LOT DEVELOPMENT, 15+ acres for Family Compound or upscale development between Pine Plains Village and Millerton on quiet road off Route 199. The Development includes a 1400 SF 2BR/2BA RANCH with new well, w/2 large decks, all wood floors, wood siding + detached 2 car garage on 7+ acres subdividable into 4 acres with house and 3 acre vacant lot. Included is additional approved 8 acre building lot with approved septic design. Additional adjoining 4 acre building lot available for $139,000. The house on 7+ acres can be purchased separately for $385,000. Easy to show unoccupied.

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$575,000

143 Ryan Rd Pine Plains, NY 12567

MLS: 873185 Photos
Beds:
4
Baths:
3.00
Sq.Ft.:
2,580
Status:
Active
MLS#:
873185
Type:
Single Family
Lot size:
1.16 Acres
Year built:
2010
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: KW MidHudson 914-962-0007
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ADDITIONAL INFORMATION

Meticulously maintained 2500+ sq ft 4-bedroom 2.5 bath center hall colonial sits on a beautiful and flat corner lot with stunning mountain views just minutes to the center of the town of Pine Plains. As you enter the home you immediately notice the care and attention to detail that the original owners have shown – Tasteful updates throughout include hardwood floors, chef’s kitchen with quartz countertops and stainless-steel appliances, including gas double oven. Head upstairs and you notice the HUGE master suite with his and her closets, updated master bath with large walk-in shower and beautiful double vanity. 3 additional bedrooms and full bath finish off the upstairs. Head downstairs to the basement and you find the top of the line Owens Corning Basement finishing system installed – Large family room, home office space and gym area make this home have endless possibilities. Outside you find the great yard including an enormous back patio with built-in propane line with grill! Minutes to Taconic State Parkway, Stissing Mountain, Thompson Pond and all the Hudson Valley has to enjoy! LIKE NEW CONSTRUCTION WITHOUT THE WAIT!

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$599,000

43 Stissing Mountain Dr Pine Plains, NY 12567

MLS: 868066 Photos
Beds:
3
Baths:
2.00
Sq.Ft.:
1,862
Status:
Active
MLS#:
868066
Type:
Single Family
Lot size:
2 Acres
Year built:
1983
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Rich Brenner Realty, LLC 914-456-4691
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ADDITIONAL INFORMATION

Welcome to 43 Stissing Mountain Drive — a peaceful and private retreat set on 2 beautifully wooded acres in the heart of the Hudson Valley. This great contemporary home offers 3 bedrooms and 2 bathrooms across 1,862 square feet of comfortable living space. With an open-concept layout, cathedral ceilings, and abundant natural light, the home blends style and function. A cozy fireplace anchors the living room, while the open concept floor plan is perfect for entertaining. Enjoy the tranquil surroundings from the covered deck or attached three season room. An attached garage adds convenience. Nestled at the base of Stissing Mountain, this property is just minutes from the Stissing Mountain Fire Tower and Thompson Pond Preserve, offering immediate access to hiking, biking, birdwatching, and panoramic views of the Catskills and Berkshires. Pine Plains itself is a picturesque small town known for its scenic beauty, rural charm, and vibrant community. Just 2 miles to the quaint Pine Plains hamlet center, you’ll find local cafés, restaurants, schools, and a theater. Rhinebeck, Red Hook, and Hudson—each bustling with shops, dining, arts, and historic appeal—are all within a 20 to 30-minute drive. Ideal for weekenders or full-time residents, this home is just: • 15 minutes to the Wassaic Metro-North station (direct to Grand Central) • 2 hours to New York City • 25 minutes to Rhinebeck and Hudson • 20 minutes to Red Hook Whether you’re seeking outdoor adventure or serene seclusion, 43 Stissing Mountain Drive offers the best of Hudson Valley living. Discover why so many are falling in love with Pine Plains—a town where nature, community, and convenience come together.

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$379,000

48 Woodside St Pine Plains, NY 12567

MLS: 857691 Photos
Beds:
3
Baths:
2.00
Sq.Ft.:
1,280
Status:
Active
MLS#:
857691
Type:
Single Family
Lot size:
0.5 Acres
Year built:
2001
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: DUTCHESS COUNTRY REALTY INC. M 518-789-6185
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ADDITIONAL INFORMATION

Whether you're beginning retirement or planning a weekend escape, 48 Woodside Street is a charming, move-in-ready home. Pine Plains offers attractions like fine dining at the Stissing House and tranquil kayaking on Thompson Pond. Nearby hiking trails include the challenging Stissing Fire Tower and the peaceful Thompson Preserve, ideal for a leisurely walk. Lions Club Park features a recreation field and access to Thompson Pond with a swimming area. Woodland Street is in a walkable neighborhood and near the Pine Plains School's track and fields. The level backyard is perfect for gardens, a pool, or other outdoor activities.

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$299,000

6 Carla Ter Pine Plains, NY 12567

MLS: 156783 Photos
Beds:
4
Baths:
2.00
Sq.Ft.:
1,488
Status:
Active
MLS#:
156783
Type:
Single Family
Lot size:
0.45 Acres
Year built:
1962
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: REO Edge, LLC 914-262-3919
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ADDITIONAL INFORMATION

Welcome to 6 Carla Terrace! This 4-bedroom ranch nestled on a quiet tree lined cul-de-sac is well situated on nearly a half-acre level lot featuring a large private driveway for multiple vehicles. The dining area features sliding glass doors to the rear deck. Conveniently located just a short distance to downtown Pine Plains and its great shops, restaurants, schools, and of course, the Stissing Center for Arts and Culture. Pine Plains is within easy driving distance to the Berkshires, and all the best that Dutchess and Columbia counties have to offer. The full unfinished basement with its high ceilings offers many possibilities. While this home could benefit from TLC, it presents a tremendous opportunity. Blink... and it will be gone.

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$384,000

Rd Pine Plains, NY 12567

MLS: 156736 Photos
Beds:
2
Baths:
2.00
Sq.Ft.:
1,336
Status:
Active
MLS#:
156736
Type:
Single Family
Lot size:
7 Acres
Year built:
1968
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Barns & Farms Realty, LLC 518-822-0226
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ADDITIONAL INFORMATION

Secluded 2BR/2BA RANCH w/2 large decks, all wood floors and wood siding + detached 2 car garage on 7+acres in Hamlet zone Easy subdivision into 4 and 3 acre lots. Also available as Family Compound with adjoining 8 acre and 4 acre boha parcels for 699,000. Great location between Pine Plains Village and Millerton on quiet road off Route 199. New well installed. Easy to show unoccupied.

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$389,000

Rd Pine Plains, NY 12567

MLS: 156736 Photos
Beds:
2
Baths:
2.00
Sq.Ft.:
1,336
Status:
Active
MLS#:
156736
Type:
Single Family
Lot size:
4 Acres
Year built:
1968
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Barns & Farms Realty, LLC 518-822-0226
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ADDITIONAL INFORMATION

Secluded 2BR/2BA RANCH w/2 large decks, all wood floors and wood siding + detached 2 car garage on a7+cres in Hamlet zone. Great location between Pine Plains Village and Millerton on quiet road off Route 199. New well installed. Back on market after buyer couldn't qualify for mortgage.Easy to show unoccupied. Easy subdivision for 4acs with house and 3 acre vacant lot.

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$4,950,000

310 Carpenter Hill Rd Pine Plains, NY 12567

MLS: 842444 Photos
Beds:
5
Baths:
5.00
Sq.Ft.:
6,310
Status:
Active
MLS#:
842444
Type:
Single Family
Lot size:
24.78 Acres
Year built:
1993
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Corcoran Country Living 845-677-0505
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ADDITIONAL INFORMATION

Nestled on top of Carpenter Hill, with unparalleled views of Stissing Mountain, the Catskills and the surrounding farmland, sits this country estate on 24.78 acres. The traditional, cedar shake 6,310 square foot home exudes elegance exhibited through the well proportioned rooms with 9’4” ceiling height, exceptional craftmanship and attention to detail found throughout the home. A dramatic double height foyer leads to the gracious living room which features a wood burning fireplace, built-ins, a cozy window seat and French doors that open to a covered porch. Lots of natural light floods into the family room through the walls of windows with western views. The chef’s kitchen boasts custom finishes, top of the line appliances, an impressive river stone matte finish granite island, pantry and opens to the spacious dining area. Three sets of French doors open to two covered porches, added in 2021, seamlessly blending indoor-outdoor living. The second floor provides the primary ensuite, two bedrooms and a full bath. Connecting the main house to the guest wing is an attractive, yet functional, mudroom with bluestone floors. The guest wing was added in 2001 and includes a foyer, kitchenette, first floor ensuite bedroom, and a second floor bedroom and bath. In 2015, a two car garage with studio above was added, creating a beautiful space for working from home, the possibilities are endless. The manicured property offers perennial gardens that bloom throughout the season. There is a gunite pool that is seamlessly blended into the landscape to embrace the surrounding vistas. Truly a remarkable property offering peace and privacy with spectacular views.

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$1,650,000

460 Silvernails Rd Pine Plains, NY 12567

MLS: 156109 Photos
Beds:
5
Baths:
3.00
Sq.Ft.:
3,802
Status:
Active
MLS#:
156109
Type:
Single Family
Lot size:
10.51 Acres
Year built:
1750
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Four Seasons Sotheby's Int. 518-822-0800
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ADDITIONAL INFORMATION

On just over ten acres of rolling hillside and pasture sits this quintessential Hudson Valley farmhouse. The oldest section of the home dates back to the mid 1700's, quite early for this region, while the Federal Style facade and front rooms were added c1850. The combination is striking the back of the house is both quaint and cozy, while the front of the home has high ceilings, big six-over-six windows and light filled spaces. The kitchen was a 2017 renovation the sink perfectly placed to overlook the Roeliff Jansen Kill, which borders the property and is stocked with brown trout by the New York DEC each spring. There is also a very fine swimming hole that remains deep even when the waters run low! Rhododendrons border the front porch and bloom in early Spring, cueing the return of summer, and the hydrangeas lining the front farm fence wait just a bit longer until the weather turns. By then, the wraparound screened in porch has become the place you spend most of your time, overlooking the water and surrounding hillsides. Inside, the house lives comfortably. The large kitchen was custom built by a local carpenter with inset cabinetry, new windows, a gas range and two sinks. The large, inviting island sits five. The wideboard floors are original. The dining room and family room sit side by side, with a fireplace at the far end and two sets of french doors leading outside. There is a half bath and mud room with radiant heated floors at the very back of the house, and the back door leads out to the run-in,'' an attached barn-like structure used for storage. At the front of the house you'll find a wood-paneled office with extensive built ins and the living room light, bright and airy. There are two bedroom wings, accessed via separate staircases. The back guest wing has two lovely bedrooms and a full bath. The front wing has three bedrooms and a full bath. The house has been lovingly cared for and thoughtfully updated over the current owner's 10+ year stewardship, with many updates, most recently a brand new boiler in 2025. The land has been certified organic and was most recently grazed and hayed by a favorite local dairy farm. Silvernails Farm is both whimsical and practical, a house built with integrity and a rare eye for aesthetics and proportion. 2h to NYC, 20m to Hudson and most importantly just 5m to Stissing House.

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$320,000

4 Antler Club Rd Pine Plains, NY 12567

MLS: 823416 Photos
Beds:
2
Baths:
2.00
Sq.Ft.:
1,620
Status:
Active
MLS#:
823416
Type:
Single Family
Lot size:
0.09 Acres
Year built:
1950
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: HomeSmart Homes & Estates 845-547-0005
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ADDITIONAL INFORMATION

Located in the picturesque Antlers Club Lake Community, this 2-bedroom, 2-bath Cape Cod offers a peaceful retreat with beach access and your own dock for kayaking, fishing, or relaxing by the water. The home features a bright and inviting layout, with spacious living areas, a well-equipped kitchen, and a full bath on the main level. Upstairs, a large bedroom and another full bath provide a cozy escape. Set back just a few hundred feet from the lake, it's private yet accessible! Enjoy the beauty and tranquility of lake community living while still being close to highways and shopping. Don’t miss this unique opportunity—schedule your showing today!

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$1,575,000

Rd Pine Plains, NY 12567

MLS: 806818 Photos
Beds:
3
Baths:
3.00
Sq.Ft.:
3,833
Status:
Active
MLS#:
806818
Type:
Single Family
Lot size:
19.28 Acres
Year built:
1985
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: William Pitt Sothebys Int Rlty 203-644-1471
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ADDITIONAL INFORMATION

Major Update! Meticulously Maintained ELEVATED 3 BEDROOM/3 BATH Log Cabin-Style home and horse barns on 19+ acres with BREATHTAKING views. Set off a quiet country road, this stunning setting with impeccably manicured grounds captures one's attention upon arrival. One is immediately drawn to the expansive wood deck complete with built-in grill and impressive screened-in gazebo with fire-pit. This is unquestionably the perfect entertainment perch which captures the beautiful long views of the valley and hillsides. Fabulous open floor plan inside, with vaulted ceilings in living room with stone fireplace, large dining area, and light and bright gourmet eat-in kitchen with high-end appliances. Primary bedroom also has vaulted ceilings, stone fireplace, and large walk-in closet leading to primary bath. Study off of Primary Bedroom. Second bedroom on main level has been recently reconfigured. Another great entertaining space is located downstairs including a large area perfect for games, exercise or media room with kitchenette. A THIRD bedroom was recently created near a recently renovated full bath. 3 car heated garage with massive storage space upstairs. 45KW generator. For the horse enthusiast, the property also includes a hay barn, paddock, 4 stall horse barn & tack room, equipment sheds and arena. Great riding trails abound. This exceptional property is move-in ready and utterly magical.

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$18,750,000

461 Silvernails Rd Pine Plains, NY 12567

MLS: 805419 Photos
Beds:
11
Baths:
8.00
Sq.Ft.:
7,500
Status:
Active
MLS#:
805419
Type:
Single Family
Lot size:
127.85 Acres
Year built:
2020
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Compass Greater NY, LLC 845-677-5311
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ADDITIONAL INFORMATION

Ingadi, the Zulu word for garden, is a true legacy compound all set within 127 acres of pristine land with a total of 11 bedrooms across four distinct residential structures. A magical journey of the senses where the Roeliff Jansen Kill and the Shekomeko Creek merge, ensuring sustainability while creating one of the most spiritually powerful and visually stunning experiences in the Hudson Valley. Rich in wildlife with numerous farming components already established there is tremendous opportunity for expansion. The recently completed 7,500sf main residence features lime stucco walls and solid fieldstone masonry on the interior and exterior with a mix of hardwood and Jerusalem limestone flooring. With 4 en-suite bedrooms, the residence also includes a powder room, a private study, large laundry room, wine cellar, and a yoga studio. The living room with 26’ ceilings is bracketed by two fireplaces. While embracing traditional craftsmanship and materials, the house is equipped with every modern convenience including an infrared sauna, steam room, 3 fireplaces, motorized shades, insect screens and radiant heated floors. The terrace has a covered seating area with a fully equipped kitchen, radiant floor heating and overhead heaters. The open design kitchen features a large pantry and workspace, 3" thick limestone counters, solid 3" walnut island with AGA stove and bar cabinet, twin dishwashers and sinks, crisper drawers, fridge, freezer, and wine fridge. There is a dog wash, covered firewood storage and a climate controlled two-car garage. South of the house, with magical river views and a fieldstone patio, sits a 60ft heated pool with an auto-cover. There is also an outdoor shower. A renovated cottage delivers two separate living spaces: upstairs is a 3-bedroom cottage and downstairs is a 2-bedroom apartment. Several barns date from the 1700’s to the early 1900’s including an equestrian barn with 9 large stalls plus 6 outdoor summer stalls, heated wash stalls, tack room, office and feed room with a renovated 2 bedroom apartment above. There is an outdoor ring with show quality footing. Years of extensive effort has restored this sacred piece of land that inspires walking barefoot through the forest, basking in the river bends, and taking wild weed walks through the abundant forests that comprise a large portion of the property. Multiple outdoor living room vignettes with wooden decks inspire glamping and play in the natural beauty of this truly divine land. For sports enthusiasts; riding, hiking, biking, rafting, kayaking, and superb fly-fishing are in abundance. Located 5 minutes from Pine Plains, 25 minutes to Rhinebeck and Hudson. This rare offering epitomizes the Hudson Valley dream.

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$7,400,000

255 Mill Hill Rd Pine Plains, NY 12567

MLS: 155003 Photos
Beds:
9
Baths:
11.00
Sq.Ft.:
9,000
Status:
Active
MLS#:
155003
Type:
Other
Lot size:
206.41 Acres
Year built:
2010
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: William Pitt Sotheby's Interna 845-677-9822
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ADDITIONAL INFORMATION

A long driveway leads to this imposing Greek Revival style house set high on a hill on 200 + acres of prime land overlooking Hudson Valley's farm country. Open fields and woodland with1600' of frontage on the Roeliff Jansen Kill. The house has 9000 sq ft with 12' ceilings throughout, large areas for entertaining, surrounding balconies for summer living and a 5000 bottle wine cave. The kitchen features a wood fired oven and the bathrooms are Carrera marble. Interior walls are plaster. All fittings and materials are of the highest quality. 9 bedrooms ensuite each with a view of the surrounding countryside. Just 2 hours north of New York City.

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$509,000

7786 S Main St Pine Plains, NY 12567

MLS: H6326089 Photos
Beds:
4
Baths:
2.00
Sq.Ft.:
3,072
Status:
Active
MLS#:
H6326089
Type:
Single Family
Lot size:
0.47 Acres
Year built:
1903
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Houlihan Lawrence Inc. 845-677-6161
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ADDITIONAL INFORMATION

You wanted charm? This vintage 1903 village home in Pine Plains, NY once served as both the town pharmacy and library, and many of the bookshelves and apothecary drawers remain. The large home on a landscaped half acre is filled with period details: wood moldings, original door knobs and intricate iron hardware, a carved mantelpiece, and several built-ins. And under the carpets are beautiful wood floors. Entered from either of two covered porches, the first floor has a living room, library, dining room, laundry room, powder room and eat-in kitchen. Upstairs are four bedrooms, a study, and a full bath with a spacious walk in closet. While the house is in move-in condition, updating the kitchen and baths will make the home really shine. The fenced-in yard has gardens, a wide-open lawn and a barn with loft that serves as a garage and workshop. Steps away from popular local restaurants and the Stissing Center for the Arts, this property is right in the heart of this up-and-coming town. Additional Information: HeatingFuel:Oil Above Ground,ParkingFeatures:2 Car Attached,

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$279,000

721 County Route 7 Pine Plains, NY 12567

MLS: H6326074 Photos
Beds:
3
Baths:
1.00
Sq.Ft.:
1,400
Status:
Active
MLS#:
H6326074
Type:
Single Family
Year built:
1820
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Houlihan Lawrence Inc. 845-677-6161
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ADDITIONAL INFORMATION

A quaint antique home the hamlet ofGallatinville, NY. This 1820 home on .68 acres is loaded with quirky charm. With vintage wallpaper, lots of built-in cabinets and bookshelves, the 3-bedroom 1-bath house is as homey as they get. From the glassed-in porch, you step into a cozy entry hall, then into a large dining room. The country kitchen and comfortable living room with wood burning fireplace insert are off the dining room, and the bathroom is on the ground floor too. Upstairs are three bedrooms and a sitting area that can be converted to a bath or furnished as a library or study. In the shade of the trees surrounding the house are a patio, an old root cellar, a stone barbecue and a raised bed vegetable garden. A two-car garage is tucked into the hillside and there's ample parking for additional cars. Once lovingly landscaped, the property has been little-used for a couple of years, but a little care will bring the gardens back to life. Come check it out! Additional Information: ParkingFeatures:2 Car Detached,

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$8,950,000

25 Winchell Trl Pine Plains, NY 12567

MLS: 153621 Photos
Beds:
5
Baths:
5.00
Sq.Ft.:
5,935
Status:
Active
MLS#:
153621
Type:
Single Family
Lot size:
28.9 Acres
Year built:
2023
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Four Seasons Sotheby's Int. 845-757-5000
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ADDITIONAL INFORMATION

Stretching across the top of 29 wildflower-blanketed acres on the southern ridge of Winchell Mountain, w/commanding Catskills views, lies High View Farm. Inspired by the rolling farmland & expansive blue skies of this very special part of the Hudson Valley, the Architectural & Interior Design duo HallidayGreer collaborated with Architect Graydon Yearick & LaGuardia Design Group Landscape Architects to create a one-of-a-kind living experience. Using sustainable natural materials & state-of-the-art building technology, High View Farm is a perfect synthesis of contemporary modernism & rural barn. Working primarily with local artisans, they have created the ultimate combination of comfort & understated luxury. Relying on the endless power of the sun & the constant, cool temperature of geothermal energy they've realized a passive, architecturally-inspired EcoLux compound that will excite and endure for generations. The 5900 sf, 5 BR/5 BA main house has 3 primary suites and 2 additional ensuite guest rooms. The baths are all appointed with Waterworks fixtures & custom cabinets. The bedrooms, all with spectacular views, are generously proportioned with custom millwork closets with oak interiors. The kitchen is a chef's dream with an AGA Mercury induction stove, a Thermador fridge, an appliance pantry, 2 dishwashers, full butler's pantry with wine refrigeration, and a Miele integrated coffee system. The great room has a masonry fireplace & dining for 14 people. The ground floor has a Tonal Smart personal training machine, free weights, a yoga/stretching area, surround-sound cinema, and a cedar sauna. The piece-de-resistance is the four season indoor/outdoor room with a wood-burning fireplace-a dream for entertaining in a country home. The 50x11ft. saltwater gunite infinity pool, w/sun-shelf & tub spa, overlooks Stissing Mtn. and has a pool house with a live green roof, full kitchen & bath, & lounge/sleeping area. It's united to the pool by floor-to-ceiling sliding glass panel doors running the length of the pool. A lovely fire pit area for cooler summer & autumn evenings is just past the pool and up the ridge from the built-in BBQ. Closer to the main house, with its own wood-burning built-in BBQ, is the Maple Grove; another idyllic outdoor moment for more elaborate summer parties & alfresco dining.More marketing remarks in "directions to property" field.

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Andrea D. Conner, License 10311208085, Xome Inc., License 10991227159, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Suite 100, Lewisville, Texas 75067

Listings courtesy of One Key MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of 11/13/2024. 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. Properties displayed may be listed or sold by various participants in the MLS. Per New York legal requirement, click here for the Standard Operating Procedures. Copyright 2025, OneKey MLS, Inc. All Rights Reserved.
Andrea D. Conner, License 10311208085, Xome Inc., License 10991227159, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Suite 100, Lewisville, Texas 75067


The data relating to real estate for sale on this web site comes in part from the Columbia Greene Northern Dutchess MLS. Real estate listings held by brokerage firms other than Xome include the name of the listing broker. Information is deemed reliable but is not guaranteed accurate by the MLS. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Per New York legal requirement, click here for the Standard Operating Procedures. Copyright 2025 Columbia Greene Northern Dutchess MLS. All rights reserved.
Andrea D. Conner, License 10311208085, Xome Inc., License 10991227159, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Suite 100, Lewisville, Texas 75067


The data relating to real estate on this website comes in part from the IDX of the Hudson Valley Catskill Region MLS. Real estate listings held by brokerage firms other than Xome are marked with IDX logo and the detailed information about them includes the name of the listing broker. Per New York legal requirement, click here for the Standard Operating Procedures. Copyright 2025 by the Hudson Valley Catskill Region MLS and Ulster County Board of Realtors, Inc. All Rights Reserved.


Pine Plains 12567 Real Estate

Pine Plains is located in New York. Pine Plains, New York 12567has a population of 2,140. Pine Plains 12567 is less family-centric than the surrounding county with 17.78% of the households containing married families with children. The county average for households married with children is 29.92%.

The median household income in Pine Plains, New York 12567 is $67,212. The median household income for the surrounding county is $87,112 compared to the national median of $69,021. The median age of people living in Pine Plains 12567 is 51.4 years.

Pine Plains Weather

The average high temperature in July is 82 degrees, with an average low temperature in January of 13.7 degrees. The average rainfall is approximately 45.6 inches per year, with 51.9 inches of snow per year.

Pine Plains Map

Pine Plains Real Estate Market Conditions

  • Median sales price

    $5,150,000
    14%
    change since last quarter

  • # Active listings

    54
    30-day change

Pine Plains Schools and Demographics

Education near Pine Plains, NY

City County
High School Graduates 89.59 91.53
College Degree - 2 year 8.56 10.4
College Degree - 4 year 28.26 37.67
Graduate Degree 7.64 13.56
Expenditures per Student 28,380 28,380
Students per Teacher 12.5 12.5

Elementary Schools near Pine Plains, NY

Grades Students P/T Ratio ZIP
Chancellor Livingston Elementary School KG - 05 442 12.9 12572
Cold Spring Early Learning Center KG - 02 195 12.2 12581
Mill Road-Intermediate Grades 03 - 05 400 14.4 12571
Mill Road-Primary Grades KG - 02 378 11.8 12571
Seymour Smith Intermediate Learning Center 03 - 05 198 11.7 12567
Webutuck Elementary School PK - 03 267 14.8 12501

Middle Schools near Pine Plains, NY

Grades Students P/T Ratio ZIP
Bulkeley Middle School 06 - 08 271 14.3 12572
Eugene Brooks Middle School 04 - 08 277 19.8 12501
Linden Avenue Middle School 06 - 08 480 13.6 12571
Stissing Mountain Middle School 06 - 08 226 13.3 12567

High Schools near Pine Plains, NY

Grades Students P/T Ratio ZIP
Red Hook Senior High School 09 - 12 663 11.9 12571
Rhinebeck Senior High School 09 - 12 390 14.3 12572
Stissing Mountain High School 09 - 12 302 12.6 12567
Webutuck High School 09 - 12 223 13.8 12501

Ungraded Schools near Pine Plains, NY

Grades Students P/T Ratio ZIP
Red Hook Residential Center 07 - 10 10 12571

Demographics near Pine Plains, NY 12567

Zip Code City
Neighborhood Type Small town
Population 2,140 296,012
Population Density 70 372
Median Age 51.4 42.5
People per Household 2.4 2.5
Median Household Income 67,212 87,112
Average Income per Capita 36,378 44,800

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