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Pine Plains NY Real Estate & Homes for Sale

36 Properties Found

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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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$1,850,000

368 Skiba Rd Pine Plains, NY 12567

MLS: 420088 Photos
Beds:
4
Baths:
3.00
Sq.Ft.:
3,200
Status:
Active
MLS#:
420088
Type:
Single Family
Subdivision:
Gallatin
Lot size:
228.3 Acres
Year built:
2011
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: CORCORAN COUNTRY LIVING ML 845-677-0505
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ADDITIONAL INFORMATION

Quintessential Hudson Valley Farmhouse. Nestled at the end of a country road in Gallatin overlooking your own stocked fishing pond, is this storybook setting with 228.3 acres of privacy. The home was newly constructed in 2011 from the original c.1787 homestead keeping some of the original details in a few rooms. A modern great room with soaring 14' beamed ceilings and a stone fireplace is the focal point of the house. A screened porch off the kitchen expands the space for summer evenings to dine. There is a primary suite on the first floor plus an additional bedroom, full bath and foyer. Upstairs, are two bedrooms and a full bath with one of the bedrooms having the original pine floors, wood paneling and beams. A detached oversized 2+ car garage/barn has many possibilities. Hardie Board siding, efficient utilities, A/C, and a whole house generator add to the appeal of this property. Delight in the peace and serenity this property offers with trails throughout the woodlands. Just 15 minutes to Pine Plains, 25 minutes to Rhinebeck, 2.5 hours to NYC and easy access to the Taconic State Parkway. Subdividable. Additional land available.

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$335,000

6 Bethel Pl Pine Plains, NY 12567

MLS: 419680 Photos
Beds:
4
Baths:
2.00
Sq.Ft.:
1,008
Status:
Active
MLS#:
419680
Type:
Single Family
Subdivision:
Pine Plains
Lot size:
0.53 Acres
Year built:
1955
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: THOMAS ZENGEN LIC RE BKR PI
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ADDITIONAL INFORMATION

Enjoy one level living in this cute ranch on a nice corner, quiet lot. Beautiful landscape. Fantastic opportunity to live in the picturesque village of Pine Plains. Walk to Stissing Lake and the Thompson Nature Preserve. Near all the amenities. Excellent starter or retirement home, freshly painted throughout. Nice level yard for a garden, family, pets and entertaining! Walk to library, community center, shops, restaurants, post office, and recreational areas and trails. An outdoor enthusiast's heaven! Come enjoy the lovely landscape, mountains, lakes and neighbors of Pine Plains! You will be impressed.

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$3,495,000

182 Silvernails Rd Pine Plains, NY 12567

MLS: 419261 Photos
Beds:
5
Baths:
6.00
Sq.Ft.:
3,974
Status:
Active
MLS#:
419261
Type:
Single Family
Subdivision:
Gallatin
Lot size:
28.5 Acres
Year built:
1980
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: CORCORAN COUNTRY LIVING ML 845-677-0505
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ADDITIONAL INFORMATION

Fly into this private, hilltop country estate with its own airstrip. This five bedroom, five and one half bath home has stunning bucolic views to Stissing Mountain and provides a layout that has an airy and elegant ambiance. The cathedral living room is centered around a soaring stone fireplace and leads to a cozy library and the formal dining room. Top of the line appliances, marble countertops, and a large butcher block clad island create the perfect chef's space. French doors from the eat-in kitchen and family room lead to a terrace with fireplace and Argentinian grill for al fresco dining. Upstairs, is the primary suite with balcony overlooking Stissing Mountain. An additional four bedrooms and three full baths are also on the second floor. The lower level offers laundry, an office and a full bath. Adding to the allure of this property is a 20' x 45' heated, gunite pool with a guest/pool house and a Har-tru tennis court. The guest/pool house features an additional loft bedroom, bath, kitchen and a gym with sauna. A fully stocked pond, garden and beautiful grounds on the 28.5 acres makes this the ideal place to unwind and enjoy the solitude of this property. Located just minutes to the quaint town of Pine Plains.

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$569,900

21 Sheldon Dr Pine Plains, NY 12567

MLS: 418975 Photos
Beds:
3
Baths:
3.00
Sq.Ft.:
2,000
Status:
Active
MLS#:
418975
Type:
Single Family
Subdivision:
Pine Plains
Lot size:
3.81 Acres
Year built:
2003
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: BHHS HUDSON VALLEY PROPERTIES FK
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ADDITIONAL INFORMATION

Beautifully designed custom built 3 bedroom 2.5 bath home with pastoral views is reminiscent of a converted barn with modern amenities. This spacious home built in 2003 is full of special features and little details throughout its flowing design. A sizable custom kitchen presides in the center of the home and is any cook's dream, with large windows offering natural light and panoramic views as a backdrop and highlighting the antique beams in the cathedral ceilings throughout the home. Massive barn doors, hardwood floors, bonus loft space and built ins add to the home's unique touches. Making this even more desirable is the home's expansive first floor garage and workshop boasting room for 3+ cars and extra tall ceilings, allowing for the space to be outfitted for any enthusiast's needs and wants. With upgraded electrical capacity and radiant heating system, this property has plenty of opportunity for additional customizations. Sitting atop a lovely 3 acres parcel, this property is just minutes from the charming and historic hamlet of Pine Plains and area attractions. With so much to offer, you will not want to miss your chance to experience this property.

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$1,750,000

243 Lake Rd Pine Plains, NY 12567

MLS: 419203 Photos
Beds:
4
Baths:
4.00
Sq.Ft.:
3,280
Status:
Active
MLS#:
419203
Type:
Single Family
Subdivision:
Pine Plains
Lot size:
2.39 Acres
Year built:
2023
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: HOULIHAN LAWRENCE INC. ML
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ADDITIONAL INFORMATION

Superbly crafted contemporary farmhouse offers seasonal views of Stissing Pond and is nestled between Thompson Pond Preserve and Stissing Mountain. Built in 2023, the residence offers 3280 fin. s.f. and 2200 unfin. s.f. on 2.39 acres (2 parcels). Main level offers chef's kitchen with Subzero, Thermador double ovens, Freedom Thermador induction cooktop with handcrafted hood, Thermador DW, CaLefort wine cooler, and quartz counters and backsplash. There is also a pantry with addtl. double drawer refrigerator. Dining room has built-in custom oak server. The living room features 20' plus ceilings with propane fireplace accented by custom oak hearth and opens to private rear porch. Primary suite offers bedroom with tray ceiling and access to rear porch; bath has soaker tub, custom glassed-in walk-in shower, privacy tinted window treatments, and heated floors and towel warmer. Lastly, there is a WIC with W/D. Upper level has 3 bedrooms, 2 baths, media room, office/gym, second laundry area and bonus room over garage. Lower level is ideal for storage/mechanicals. There is a 2-car att. garage w/ EV charger. The residence is sited on one of 2 lots offered with BOHA vacant lot ideal for a studio/guest house and pool. Minutes to center of Pine Plains with its world class Stissing House restaurant and Stissing Center performing arts center, 10 minutes to the TSP and about 20 minutes to Rhinebeck and Red Hook.

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$2,750,000

570 Bean River Rd Pine Plains, NY 12567

MLS: 419101 Photos
Beds:
3
Baths:
4.00
Sq.Ft.:
3,072
Status:
Active
MLS#:
419101
Type:
Single Family
Subdivision:
Pine Plains
Lot size:
22.59 Acres
Year built:
2023
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: NEIL CHARLES REAL ESTATE. ST
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ADDITIONAL INFORMATION

The approach to this spectacular contemporary barn-style home takes you up a long, winding private driveway past open fields & woods that are part of this special 22+ acre property. At the top of the hill, sits this incredibly private, recently completed, custom, stick built, 3-bedroom, 3.5-bath, contemporary home boasting approximately 4,000 sf of total square footage. This stunning home is designed to take advantage of its exquisite surroundings and to be one with nature with lots of windows, an open floor plan, and soaring high ceilings. Features include a standing seam roof, a lovely in-ground gunite pool, 9' engineered European oak flooring, a fabulous loft office/den, custom cabinetry and vanities, bedrooms with baths en suite, beautiful tiling, a contemporary propane fireplace, high-end appliances and a full basement, the perfect place for a gym/media room/family room/ playroom. Through the trees that surround the home, you can see glimpses of the mountains and pastoral farmland, and with some clearing, the views would be truly unparalleled. Conveniently located in New York's scenic Hudson Valley, just 6 minutes to Millerton & Pine Plains, 20 minutes to Rhinebeck, Red Hook & Millbrook and under 2 hours to NYC. Additional options at additional cost include bluestone patio, decking, garage and much more. Agricultural exemption ensures ongoing tax advantages! A truly stunning and unique, must-see private property (not in a development).

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$650,000

71 Lake Shore Dr Pine Plains, NY 12581

MLS: 418690 Photos
Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
418690
Type:
Other
Subdivision:
Pine Plains
Lot size:
0.85 Acres
Year built:
2021
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: CORCORAN COUNTRY LIVING RH
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ADDITIONAL INFORMATION

'Experience Island Life in the Hudson Valley! This unique property consists of three separate parcels, offering a truly extraordinary opportunity. The centerpiece is a picturesque 0.25-acre island on Twin Island Lake, Pine Plains, NY, currently thriving as a successful Airbnb destination. The island is thoughtfully furnished with a safari-style tent and provides all the necessary amenities, including a charming gazebo, a cook grill, a firepit, and outdoor bathroom facilities. Your journey begins on the mainland, where you'll find an 0.85-acre parcel with a convenient dock, allowing easy access to the island via canoe or kayak. Additionally, this parcel boasts a 2-story, 1,152 sq ft Amish-built barn, offering immense potential for conversion into living space. BOHA is in progress. On the east side of Twin Island Lake, a small 20x20 parcel awaits your creativity. Use it for parking or consider building a dock here for added convenience. This property is a genuine one-of-a-kind gem with endless opportunities. Twin Island Lake is part of the scenic landscape at the base of Stissing Mountain, and it offers a wealth of outdoor activities. Whether you want to hike Stissing Mountain, explore the four-mile trail through Thompsons Pond, or simply relax by swimming in Stissing Lake, this is a haven for nature enthusiasts. You can continue to run your own Airbnb or make this serene and peaceful place your permanent residence. Pine Plains is conveniently located just 2 hours from New York City and 15 minutes from the Taconic State Parkway, making it centrally situated between the charming towns of Hudson to the north and Red Hook and Rhinebeck to the south. Don't miss out on the opportunity to live the tranquil lake life in the heart of the Hudson Valley.'

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$1,675,000

Bean River Rd Pine Plains, NY 12567

MLS: 418223 Photos
Beds:
2
Baths:
3.00
Sq.Ft.:
3,833
Status:
Active
MLS#:
418223
Type:
Single Family
Subdivision:
Pine Plains
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 SOTHEBY'S INT'L R CT
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ADDITIONAL INFORMATION

Meticulously Maintained ELEVATED Log Cabin-Style home and horse barns on 19+ acres with BREATHTAKING Mountain 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 expansive 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. Den/study off of primary bedroom. Another great entertaining space is found downstairs including a large area perfect for games, exercise or media room with kitchenette. Also downstairs is a large second bedroom and updated bathroom. 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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$275,000

Bean River Rd Pine Plains, NY 12567

MLS: 417442 Photos
Beds:
3
Baths:
2.00
Sq.Ft.:
1,200
Status:
Active
MLS#:
417442
Type:
Single Family
Subdivision:
Pine Plains
Lot size:
2.06 Acres
Year built:
2007
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: HOULIHAN LAWRENCE INC. ML
Request Info Save Property
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ADDITIONAL INFORMATION

Great opportunity for first time homebuyer or retirees. Great location, close to everything in Pine Plains Rhinebeck & Hudson. This won't last! One floor living, ranch style home, ready to move in.

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$1,195,000

35 Bryan Farm Ln Pine Plains, NY 12567

MLS: 413336 Photos
Beds:
2
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
413336
Type:
Single Family
Subdivision:
North East
Lot size:
17.15 Acres
Year built:
1999
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: ELYSE HARNEY REAL ESTATE CT
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ADDITIONAL INFORMATION

Welcome to your private oasis in the Hamlet of Shekomeko! This contemporary home, inspired by a mid-19th-century wagon barn, sits on 17 pristine acres with breathtaking protected views. The unique blend of rustic charm and modern amenities makes this property a rare find. Entering the home, you'll be greeted by the light-filled dining room that opens to the kitchen. Enjoy the natural beauty of the area from the terrace with stunning views, perfect for al fresco dining. The great room, with its wood-burning fireplace and high ceilings, is ideal for entertaining. The oversized screened porch with bluestone floors offers a bug-free haven to enjoy the outdoors. The well-proportioned primary suite on the second floor features vaulted ceilings and opens to a sitting room with stunning views. The primary bathroom boasts a tub and a separate shower. Conveniently located just minutes from Millerton, New York, and near the Wassaic Train Station, this property offers easy access to the culturally rich towns of Salisbury and Sharon, Connecticut. The area is perfect for outdoor enthusiasts, with ample opportunities for hiking, biking, and skiing. Don't miss your chance to own this unique contemporary home, combining the charm of a traditional barn with modern comforts. It's the perfect retreat for those seeking peace, tranquility, and a touch of history.

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26–36 of 36 properties displayed
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 for sale or lease on this web site comes in part from the MHMLS. Real estate listings held by brokerage firms other than this broker', Realtors are marked with the MHMLS logo or an abbreviated logo and detailed information about them includes the name of the listing broker. The information appearing herein has not been verified by the Mid-Hudson Multiple Listing Service, Inc. or by any individual(s) who may be affiliated with said entity, all of whom hereby collectively and severally disclaim any and all responsibility for the accuracy of the information appearing at this web site, at any time or from time to time. All such information should be independently verified by the recipient of such data. This data is not warranted for any purpose. Any use of search facilities other than by a consumer seeking to purchase or lease real estate is prohibited. Per New York legal requirement, click here for the Standard Operating Procedures. Copyright 2025 Mid-Hudson Multiple Listing Service, Inc. All Rights Reserved.


Pine Plains Real Estate

Pine Plains is located in New York. Pine Plains, New York has a population of 2,140. Pine Plains is less family-centric than the surrounding county with 19.59% 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 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 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

    59
    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

City County
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

Real estate near Pine Plains

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