Courtesy: Houlihan Lawrence Inc.
845-876-4443
Set on 16.17 acres of protected conservation land within a 660-acre viewshed, this exceptional modern farmhouse offers an extraordinary blend of sophisticated design, refined craftsmanship and the natural beauty of the Hudson Valley. Two ponds, and sweeping mountain and countryside vistas create a spectacular backdrop, best enjoyed from the expansive wraparound porch. An extensive, architecturally refined renovation completed in 2023 and featured in Elle Decor showcases soaring ceilings, clean architectural lines and carefully curated materials and finishes throughout. The main residence is designed for both comfortable living and gracious entertaining. Making a striking first impression, the foyer and soaring staircase are enveloped in a rich tambour wood wrapping, masterfully hiding flush-mount doors for a sleek, secret-room effect. The dramatic double-height great room, anchored by a towering wood-burning fireplace and featuring dramatic pendant lighting by Giopato & Coombes, offers a generous gathering space. The dining area is placed to maximize the views and can easily accommodate large gatherings. Two first-floor bedrooms and a full bath provide a private guest wing. The beautifully appointed chef's kitchen features top-of-the-line appliances including a new Wolf range, stone countertops, a breakfast nook, and walk-in pantry, a whimsical powder room and a laundry room with an oversized soapstone utility sink. Unwind on the upper level in the primary suite. Enjoy mornings on the balcony taking in the views, cozy evenings by the fireplace and a spa-like bath featuring 2 vanities, a discrete water closet and soaking tub. Two additional bedrooms and another full bath complete the 2nd floor. Premium amenities include a lower-level media room, an attached two car garage equipped with an EV charger, and a generator for peace of mind. The two-story barn pool house boasts a kitchen (no range), living area with custom built-in beds, a sauna and full bath. Upstairs, a large climate-controlled loft offers a versatile open space currently used as an artist's studio. Harmoniously integrated into the landscape, the 44' x 20' saline Gunite pool and adjoining hot tub offer the ultimate in outdoor relaxation. The outdoor kitchen features a high-performance Kalamazoo gourmet grill, pizza oven and smoker creating an ideal setting for entertaining. With its exceptional amenities, breathtaking views and thoughtfully designed living spaces, this remarkable country estate is the quintessential Upstate retreat.
Courtesy: Houlihan Lawrence Inc.
518-822-0300
Welcome to Sigler Estate, a park-like Hudson Valley compound of country houses, historic barns, and cultivated grounds on nearly sprawling 40 acres, minutes from the hamlet of Pine Plains. A new heated 50-foot saltwater pool sits among rolling meadows, mature woodland, and stone-terraced gardens. A restored vintage post & beam home with big views toward the Taconic Mountains, a charming white clapboard cottage, and a one-bedroom studio have each been given a professional designer renovation, and the circa 1930 Main House, with six fireplaces, awaits restoration. Along the drive stands the original Silvernails railroad depot, a link to the estate's past. In all, ten bedrooms and seven baths fill 6,860 square feet across the residences. In the designer Post & Beam, hand-built solid oak posts and beams rise over oak floors in the high-ceilinged great room, where a floor-to-ceiling stone hearth and chimney frame a new cast-iron wood stove. The open kitchen pairs custom cabinetry and Carrara marble with Bosch appliances, and mullioned windows and French doors bring the meadows in from every room. A main-floor bedroom sits beside a bath with a restored antique clawfoot tub, and the loft above has a second bedroom and sunny reading nook. The walkout lower level offers a primary bedroom with a statuario marble bath, plus a media room. Radiant heated floors and custom millwork carry through the house. Outside, a 24-foot Thermory ash deck with a custom cedar hot tub overlooks the fields, and a stone terrace below opens to gardens, stone walls, and a fire pit. Reached by its own private driveway, the Cottage has an easy character, with a dormered roofline, painted beams, and new Marvin windows. Its open kitchen and dining area face the grounds, with a living room, main-floor bedroom, and renovated bath on the first level and two more bedrooms upstairs. The fully renovated Studio, with clean lines, an open plan, and a full bath, suits an artist, a home office, or visiting guests. With its own address and private driveway, the Main House is wrapped in weathered gray shingles and opens to a vaulted beadboard living room with a fieldstone fireplace and a wall of windows. Its lower level has been gutted to the studs, ready to be configured to a new owner's specifications around a striking river-stone chimneypiece that rises to the ceiling like a beehive. A garden path leads to the pool, completed in 2021 with Roman steps, a hand-built stone wall, retractable cover, and mechanical shed. A Dutch barn with original dairy stalls now serves as a renovated workshop with office and loft, and a three-car barn garage, root cellars, and a chicken coop complete the outbuildings. The depot served the Rhinebeck and CT line, nicknamed the Hucklebush for trains slow enough for passengers to hop off to pick berries. The owners have invested deeply throughout, from new 800-amp combined service to a whole-house generator. Stone walls and walking trails, made for cross-country skiing in winter, wind through the acreage. In the center of Pine Plains, Stissing House, a 1782 tavern reimagined by chef Clare de Boer, was named one of the best restaurants in America by Food & Wine, and the Stissing Center hosts concerts and theater year-round. The Roeliff Jansen Kill is within walking distance, the 90-foot fire tower atop Stissing Mountain rewards a climb with sweeping views, and Thompson Pond Preserve circles a glacial pond rich with birdlife. Millerton's antique shops and the Wassaic Project are about 20 minutes away. Hudson, Rhinebeck, and the Rhinecliff Amtrak station are about 30 minutes away, and NYC is roughly two hours away. The Post & Beam has operated as a successful vacation rental when not in use by the owners, and the estate offers many possibilities: a multigenerational private country compound, a creative retreat with studio and workshop, or a country home with guest houses that earn their keep.
Courtesy: Compass Greater NY, LLC
845-677-5311
A great country house reveals itself through its relationship to the land, the proportions of its rooms, and the pleasure of spending time there. At Heron Hill, these qualities come together in a Greek Revival home set on 38 acres in Pine Plains, in the heart of Millbrook Hunt Country. The white clapboard facade, framed by rolling lawn and clipped boxwood, has a pleasing balance and quiet presence. A columned entrance establishes the house’s classical character, while the surrounding landscape opens to long views across fields and wooded hills. Within, the house offers a sequence of rooms that feel both substantial and intimate. Rich wood paneling, a coffered ceiling, and two wood-burning fireplaces lend warmth to the principal living space, where a curved staircase rises to a wood-paneled upper landing. A lacquered library provides a more secluded place to read or work, while the dining room and window-lined sunroom accommodate the sociable rhythms of country life. The kitchen is arranged around a generous island, with a breakfast area set beneath a broad arched window overlooking the grounds. Throughout the interiors, carefully selected materials complement the architecture, bringing individuality to rooms connected by consistent attention to scale and detail. Four bedrooms, a large playroom, four full bathrooms, and three half baths provide comfortable accommodation for guests. Along the rear of the house, a columned loggia creates a place to sit, dine, and take in the landscape. Beyond it, lawns give way to fenced fields, mature trees, and the hills in the distance. A freeform swimming pool, edged by a stone terrace, follows the natural character of the grounds, while a separate stable lends an unmistakable sense of country life. A two-car garage includes a one bedroom apartment above, ideal for guests or a caretaker. Heron Hill offers the enduring pleasures of a country home; welcoming rooms, thoughtful architectural detail, and a landscape that becomes part of daily life.
Courtesy: Houlihan Lawrence, Inc
518-822-0300
Welcome to Willow Vale Farmhouse, a 1790s farmhouse on just under 3 acres along a quiet country road in Pine Plains, Dutchess County, with 700 feet of frontage on the Shekomeko Creek. Over four years, the owners worked with a team of craftspeople to meticulously restore the home, preserving its historic character and bringing professional designer acumen to all the details. Inside, 3,065 square feet include 3 bedrooms, 3 full baths, and gracious rooms with new Venetian plaster and beautifully restored old growth Heart Pine wide plank floors throughout, warmed by multiple wood-burning fireplaces. Outside, a durable metal roof and new copper gutters cap the restoration in materials that will weather handsomely. A historic barn retains its hand-hewn beams to serve as a studio, collector’s garage, or party barn. The setting is quintessential Hudson Valley, a pastoral landscape of open farm fields and winding creek. In the kitchen, wide plank floors hand-painted in a harlequin pattern run beneath a beadboard ceiling, and a matte black La Cornue gas range stands against statuario marble counters and custom-built maple millwork. Mullioned windows look over the verdant backyard to nearby cornfields, and an antique butcher block island, skirted in a vintage Moroccan kilim, gathers everyone together. Beside it, a dining area sits near tall French windows. A generous living room opens toward the terrace, and a light-soaked sunroom overlooks the front lawn. The library features a working wood fireplace, made for winter afternoons or cozy evenings with a glass of wine. A dining room with its own sitting area completes the main floor, along with a full bath finished in Belgian terracotta tile. Upstairs, the primary bedroom is warmed by a fireplace and expansive stone hearth, with a second bedroom across the hall. Nearby, the largest bath combines an antique clawfoot tub, Rohl fixtures, and custom Schumacher shower curtain with a marble sink in a matching skirt. The third bedroom occupies its own private wing above the kitchen, with a private full bath. Willow Vale Farmhouse has a celebrated and historic past. Decades ago the house operated as Mon Blason, an inn remembered as the first haute cuisine French restaurant in the Hudson Valley, run by chef & author Charles Virion, who cooked for Orson Welles and the Ringling brothers. It was also the home of Theoni Aldredge, the Oscar- and Tony-winning costume designer whose work included the 1974 film The Great Gatsby starring Robert Redford. Outside, a broad bluestone terrace sets the stage for long summer dinners and conversations, and a hot tub waits for chilly nights. The park-like lawn runs down to the Shekomeko, where two artesian-fed swimming holes turn summer afternoons into small adventures. A fire pit draws everyone outdoors on autumn evenings, and the barn, the oldest structure on the property, holds possibilities all its own. Minutes away in the village of Pine Plains, Stissing House, the 1782 tavern where chef Clare de Boer’s wood-fired cooking ranked on The New York Times list of America’s most exciting restaurants, leads a small but serious dining scene that includes Champêtre, the French bistro from chef Michel Jean. Above the village, a hiking trail winds up Stissing Mountain to a historic fire tower with 360-degree views over Thompson Pond and out toward CT, MA, and VT. Culture is close too, from performances at The Stissing Center to contemporary art at the Wassaic Project and films at the century-old Moviehouse in Millerton, just 12 minutes away. Rhinebeck and Hudson are half an hour by car, and NYC about two hours. Amtrak from Hudson or Rhinecliff and Metro-North from Wassaic run straight to Manhattan. A fall weekend might mean coffee on the terrace, a home-cooked brunch with fresh produce and meats from local farm stands, a hike up Stissing Mountain, and an evening of stories and laughter by the library fireplace, with the sound of the creek just beyond the lawn.
Courtesy: Thomas Zengen
845-224-8005
2 FIREPLACES PINE PLAINS/ HUDSON VALLEY / STISSING LAKE Stunning lakeside 4BR/2.5BA beautiful home nestled under the majestic Stissing Mountain in private Antler Club co-op. An outdoor enthusiast's dream! Fully furnished and move in ready. Whether this lakeside home is your year-long residence or vacation & holiday retreat, Stissing Lake will be your new favorite spot in the beautiful Hudson Valley. Exceptional craftsmanship with beautiful decor, built in shelving, molding & hardwood & tiled floors throughout entire home. Natural light throughout entire home from large windows & skylights. Soft recessed lighting & fixtures throughout. Open kitchen, dining and living room layout with fireplace, double sliding glass doors opens to large deck offers the perfect setup for entertaining company or relaxation at its finest. First floor den / media room in addition to kitchen/living room layout with beautifully designed full bathroom. You will be impressed! Main level office makes this a perfect live / work from home opportunity. Large primary bedroom with built-in shelving, walk-in closet & cozy propane fireplace overlooks stunning lake scene. Cozy bedrooms including one guest suite with bathroom & private entry. Property sits up high above the lake for exceptional views all year long. Docks on site. Enjoy your day watching eagles, swans, ducks & cranes fly between neighboring Twin Island Lake & Thompson Pond or jump on the row boats, kayaks & paddle boards to fish or simply explore the abundant wildlife at beautiful Stissing Lake. A minute's walk to Stissing Mountain Fire Tower trailhead to view the Catskill & Berkshire Mountains like no other spot in this beautiful upstate region! Short drive to Taconic, trains, shopping & neighboring Rhinebeck, Red Hook, Millerton, Kingston, Copake and Great Barrington. Updated mechanicals including combi-boiler. Storage shed located in large parking area adjacent to home. Parking for multiple vehicles. Don't miss out on this Hudson Valley gem! Low total taxes of $3,299. Call for a tour today. Cash and Owner finance opportunity as property is part of Antler Club.
Courtesy: Corcoran Country Living
845-765-4888
NEW CONSTRUCTION. BE IN FOR THE HOLIDAYS!! Discover an extraordinary expression of modern luxury, where architectural sophistication meets the breathtaking natural beauty of the Hudson Valley. Privately situated on over eight magnificent acres, this exceptional 5,000 plus-square-foot contemporary residence offers an unparalleled sense of serenity, seclusion, and understated elegance, all framed by sweeping views of the majestic Catskill Mountains. A picturesque, winding drive welcomes you to this striking architectural retreat, where dramatic rooflines, expansive walls of glass, and thoughtfully designed living spaces create a seamless connection between refined interiors and the surrounding landscape. Designed for both sophisticated entertaining and effortless everyday living, the residence features two luxurious primary suites, thoughtfully positioned on the first and second floors to provide exceptional privacy and versatility. An expansive wraparound deck invites you to experience the beauty of the outdoors, offering an idyllic setting for morning coffee, sunset gatherings, or simply enjoying the tranquility of the mountains. A spacious three-car garage complements the home’s impressive scale and thoughtful design. Surrounded by mature woodlands and expansive open space, the property offers a rare combination of complete privacy and natural grandeur. Each season transforms the landscape into a breathtaking backdrop, from lush summer greenery to the brilliant colors of autumn and the peaceful stillness of winter. Set within the coveted Hudson Valley, this remarkable estate represents an exceptional opportunity for those seeking an elevated lifestyle defined by privacy, architectural distinction, and an extraordinary connection to nature. A sanctuary of sophistication. A setting of unparalleled beauty. A truly exceptional Hudson Valley offering. Photos of finished spaces are of recent builds and for representation of quality of craftsmanship.
Courtesy: Compass Greater NY, LLC
845-677-5311
Set on 50 acres of complete privacy, this 1930's Colonial sits alone with sweeping views to the Berkshires. The home offers country living with a Livingroom with a fireplace & French Doors, Dining room with French doors opening to a porch. There is a heated sunroom to enjoy the quiet outside. The primary suite includes its own bathroom and a balcony perfect for morning coffee or stargazing. For added space, the third floor has been made into a yoga/workout room, along with an office and a bath. There are additional two bedrooms and 1 1/2 baths. Outside, sits a charming gazebo overlooking a tranquil pond perfect for nature watching. Also, there is a two car garage and an additional barn for a workshop or studio. Some updates are needed. 18 acres have a conservation easement .
Courtesy: Keller Williams Realty
845-928-8000
SELLER INCENTIVE: Rare Pine Plains lakefront opportunity at an unbeatable price! To help you enjoy the lake lifestyle with complete financial peace of mind, the seller is offering a credit toward a 2-1 interest rate buydown (or toward closing costs) with an acceptable offer, giving you the power to significantly lower your monthly mortgage payments for the first two years. Welcome to 559 Lake Road in Pine Plains! Boasting direct views and access to Twin Island Lake, this beautiful property has it all: breathtaking lake and mountain vistas across more than 4 private acres. Whether you are seeking a lucrative investment, a dream summer getaway, or a year-round sanctuary, this home delivers. The entire front of the home features stunning water views. Start your mornings on the covered porch surrounded by perennial flowers, sipping coffee, listening to the birds, and watching the wildlife on the water. Inside, a bright, spacious open floor plan is ideal for modern living and entertaining. The thoughtful layout includes a primary bedroom and en-suite bath with generous closet space, plus a second bedroom and a flexible home office with a large closet (sleeps like a three-bedroom). Step outside to hike and explore your own private hillside acreage, or drive just 15 minutes to enjoy top-tier dining, shopping, and entertainment in nearby Red Hook and Rhinebeck. All this peace and quiet is located under two hours from NYC via the Taconic State Parkway. Reach out today for financing breakdown details and private tour availability!
Courtesy: Houlihan Lawrence, Inc
518-822-0300
Charming Cape Cod Retreat on Nearly 6 Acres in Pine Plains. Tucked away on a quiet country road just outside the village of Pine Plains, this charming three-bedroom, two-bath Cape Cod offers the perfect blend of country tranquility, comfortable living, and endless possibilities on nearly six beautiful acres. Welcoming you home with its cheerful yellow exterior, the spacious main level features a comfortable living room, dining area, kitchen, and convenient three-quarter bath. Upstairs, you’ll find three bedrooms and a second full bath, providing plenty of room for family and guests. The walkout basement offers excellent potential and could easily become a creative studio, workshop, hobby space, home gym, or additional living area. A one-car garage with storage below adds even more practicality and space. Step outside onto the generous rear deck and take in the peaceful surroundings. The home is privately set back from the road among mature trees and a shady lawn, while the wooded portion of the property offers something truly special: two streams that converge on the property, creating a picturesque natural setting. Behind the house is a large, sunny open area with plenty of room for gardening, outdoor games, entertaining, or simply enjoying the beauty and privacy of your own country retreat. The location is equally appealing. You’re close to local farms, restaurants, galleries, and music venues, with numerous hiking, biking, and outdoor recreation opportunities within an easy drive. Nearby Millerton, Rhinebeck, and other Hudson Valley destinations offer even more shopping, dining, and entertainment. Located less than a two-hour drive from Manhattan and a short 20 minute drive to the nearest Metro north train station, this property is ideally suited as a peaceful weekend getaway, vacation retreat, or full-time country home. With nearly six acres, beautiful natural features, flexible living space, and a wonderful Hudson Valley location, this is a rare opportunity to create your own private escape in Pine Plains.
Courtesy: Elyse Harney Real Estate
518-789-8800
Set on approximately .53 acres in a desirable Pine Plains neighborhood, this three-bedroom, one-bath mobile home offers an excellent opportunity for those looking to bring their vision and creativity to a property with potential. The home is in need of some TLC and is ready for renovation, updating, and thoughtful improvements to restore its appeal and make it shine once again. With a convenient location just minutes from the center of Pine Plains, this property combines a peaceful neighborhood setting with easy access to local shops, dining, services, and community amenities. Whether you are looking for a renovation project, investment opportunity, or a place to create a home tailored to your own style, this property offers an appealing opportunity in the heart of the Hudson Valley.
Courtesy: BHHS Hudson Valley Properties
845-473-1650
Here is a truly exceptional opportunity to enjoy the peaceful lifestyle that comes with lakefront living. Immerse in the sounds of nature, enjoy the changing seasons, spend warm summer days kayaking on the lake, and relax in a setting that feels like a true departure from the everyday. Welcome to your sweet escape at 31 Lake Shore Drive, a charming cottage with an open floor plan and vaulted ceiling that's well suited for year-round living. The flexible layout allows you to use the home as either a one- or two-bedroom, depending on your needs. Imagine enjoying dinner every evening with the lake as your backdrop or unwinding on the rear deck while taking in the beautiful water views. From morning coffee at sunrise to relaxing evenings by the water, this home offers a peaceful place to create lasting memories with loved ones and friends. You will enjoy the benefit a spacious basement and a detached one-car garage, providing plenty of storage for outdoor equipment, seasonal items, or hobbies. Situated on nearly half an acre with mature trees for an added buffer of privacy, there's ample room for outdoor activities, entertaining, gardening, or simply enjoying the open space. Whether you're looking for a full-time residence or a weekend retreat this oasis offers the comfort, charm, and lifestyle that make lakefront living so special. It all awaits you! Make it yours today. Please do not go on the property without a confirmed appointment. Schedule a tour today.
Courtesy: BHHS Hudson Valley Properties
845-473-1650
Attractive 3 bedroom, 1 bath cape cod loaded with recent improvements. Attractive open floor plan includes kitchen w/stainless appliances, granite counters & breakfast bar, which flows seamlessly to living room w/fireplace. Two first floor bedrooms and tile bathroom. Second floor includes generously sized bedroom plus office/den and storage space. Three season front porch is the perfect place to relax. Recent improvements include roof, furnace, water heater, pressure tank and 200 amp electric service. One car garage plus large workshop/studio space complete with insulation & electric and dedicated driveway. All situated on park-like property just minutes from shopping, dining, Stissing Lake and Taconic State Parkway. Attractively low taxes. An opportunity not to be missed.
Courtesy: Thomas Zengen
845-224-8005
Beautiful, quiet neighborhood with park like setting. Lovely three-bedroom home with landscaped front, back and side yards. Spacious living room flows into quaint dining room with stained pine tongue & groove walls & updated country kitchen with backyard walkout access. Whether you're relaxing in front of the fireplace in the living room or entertaining friends at the backyard fire pit, you will love your new life in beautiful Pine Plains township! Updated kitchen with Farmhouse Sink & Butcher Block counters and shelving. Complete top of the line package of Samsung Wi Fi appliances including Samsung Refrigerator, Stove, Microwave & Washer/Dryer. Hardwood floors throughout. Newer roof and boiler. Brand new finished outdoor shed stays! Short walk to Stissing Pond Rec Beach, ball fields and boat launch. A nature enthusiast's dream with nearby hiking trails throughout beautiful Stissing Mountain as well as Thompson Pond & Twin Island Lake, all just a few minutes’ walk through quiet back roads. Five-minute walk to shops, restaurants, high school, post office, salons, popular Back Bar Beer Garden and world famous Stissing House! Five-minute drive to Taconic Parkway. Central to Rhinebeck, Red Hook, Millerton, Kingston and Great Barrington. Call today!
Courtesy: Compass Greater NY, LLC
845-677-5311
Privately set on 32 extraordinary acres in the heart of Shekomeko, this light-filled country retreat captures sweeping views of Stissing Mountain and the Catskills from nearly every vantage point. A long drive winds through the landscape to a thoughtfully sited three-bedroom, two and a half bath residence featuring vaulted ceilings, expansive windows, a wood stove, and exceptional southern, western, and northern exposures. The 2,250-square-foot home includes a large porch, an outdoor shower, and an attached two-car garage, offering comfortable living amid complete tranquility. Equally compelling is the land itself—an exceptional setting for recreation, privacy, and even a future build for a larger main residence while retaining the existing home as a guest residence. A rare opportunity to own one of Shekomeko's most scenic properties, where dramatic views, acreage, and endless potential converge. 1504 Route 83 is conveniently located; minutes to Mashomack, 10 minutes to Pine Plains and Millerton, and 20 minutes to Millbrook.
Courtesy: Elyse Harney Real Estate
860-435-2200
Light-filled 2006 home blends privacy with effortless convenience. An open-air front porch and a generous backyard frame inviting indoor/outdoor living. Inside, the living room centers on a charming stove, while the chef’s kitchen echoes the home’s airy feel with an island and open plan ideal for entertaining. The first-floor primary suite is a private retreat with a freestanding tub and tiled shower. A powder room and a large mudroom with built-in bench connect to the garage. Upstairs, three additional bedrooms share a full bath with double vanities and a washer/dryer hook-up. The lower level adds flexible space with a recreational room and an office/den. Country living, refined and easy. Set just minutes from the village of Pine Plains & 15-20 minute drive to Rhinebeck and Millerton
Courtesy: Rich Brenner Realty, LLC
914-456-4691
More space and flexibility than you might expect! Set along a quiet country road in the Town of Gallatin, just outside Pine Plains, this 3-bedroom ranch offers approximately 1,860 square feet of living space with a finished lower level, providing plenty of room to spread out, work from home, entertain, or accommodate guests. The main level features hardwood floors, a full bathroom, three bedrooms, and a functional layout that’s ready to make your own. Downstairs, the finished lower level significantly expands the possibilities with additional living and dining areas, a full bathroom, and a second kitchen—known by the owners as the home’s “summer kitchen.” Whether used for recreation, guests, a home office, hobbies, or additional household space, this level gives the home versatility that’s increasingly hard to find. Outside, enjoy a covered patio perfect for relaxing, grilling, and outdoor dining, while the manageable property offers a peaceful country setting surrounded by the natural beauty of the Hudson Valley. Conveniently located near the hamlet of Pine Plains, with easy access to Millbrook, Millerton, Rhinebeck, Red Hook and surrounding communities. If you’ve been searching for a home that offers more usable space, a flexible floor plan, and country living at an approachable price point, 211 Sigler Road deserves a closer look. Come see how much this home has to offer.
Courtesy: Margaret Mondello Real Estate
845-519-7016
Stunning renovated Colonial farmhouse set in a peaceful country setting with beautiful pastoral views, just minutes to the Village of Pine Plains. Completely updated in 2020, this spacious home offers the perfect blend of classic charm and modern finishes. The main residence features 4 large bedrooms and 3 full bathrooms, a gracious formal dining room, and a bright, open kitchen with tile flooring and an electric fireplace for a warm, inviting feel. The oversized living room is filled with natural light and highlighted by a beautiful bay window. A finished attic provides additional flexible space, ideal for a home office, studio, or a fun hang out space for teenagers. A standout feature is the separate in-law suite or legal rental, offering 3 bedrooms and 2 full bathrooms with upscale finishes and tile work throughout—perfect for extended family, guests, or income potential. Enjoy quiet country living with easy access to everything the area has to offer—just minutes to Pine Plains and a short drive to Millerton. Spend your weekends exploring local farm stands and farm-to-table dining, walking trails, and scenic hiking. Stissing Lake is nearby for kayaking, swimming, and relaxing summer days. Conveniently located just 10 minutes to Millerton and within 20 minutes to both Red Hook and Rhinebeck. A rare opportunity to own a versatile and beautifully updated property in one of the Hudson Valley’s most charming countryside settings.
Courtesy: Houlihan Lawrence Inc.
845-677-6161
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 year-round usability. The property features a total of 33 stalls across three well-equipped barns. The Morton barn includes 12 stalls along with a wash stall, tack room, bath, and a large one-bedroom apartment. The main barn provides 15 stalls, including box stalls, and is complemented by a feed room, office, workshop, and medical room. The tractor barn offers six additional stalls, and automatic waterers are positioned throughout the fields to support daily operations. Residential accommodations include a main house and two three-bedroom cottages, offering flexible living arrangements for owners, staff, or guests. The property is supported by four wells, multiple septic systems, oil fired forced hot air heating, and generator hookups with gas generators, ensuring reliable service throughout the farm. One of the most distinguishing features of Cedar Ridge Farm is its exceptionally flat topography—an uncommon asset in this region that makes the land ideal for a variety of equestrian uses, including the potential development of regulation size polo fields. While the property is not eligible for subdivision, it does include a designated homesite for future construction. Cedar Ridge Farm presents a rare opportunity to own a fully equipped, largescale equestrian property in one of the Hudson Valley’s most established and desirable horse communities. It combines functionality, beauty, and long-term potential, making it an outstanding offering at the highest level of the market.
Courtesy: Corcoran Country Living
845-876-6676
A Home with a view of Stissing Mountain! Enjoy gorgeous sunsets all year long from your front door. Many updates - including a new roof!! 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 bath. A second hallway full bath is conveniently located for use by the other two bedrooms. First floor also has guest quarters that include a bedroom, half bath and sitting room or office. Finished basement with a gas fireplace for those chilly winter nights at home with family. An additional room that could be for gaming, office or den. Completing the lower level is a separate room for laundry. There is also a one car garage and an unfinished bonus room waiting for you to make it special to you. Plenty of yard space for outdoor activities and BBQs. Driveway has room for plenty of off-street parking. Quiet road conveniently located near the town park – beach, kayaking, playground, large pavilion, picnic area, etc. A short distance to Thompson Pond Nature Preserve, plenty of hiking trails including a trail up to the Stissing Fire Tower. Less than a mile from village center with its quaint shops and eateries – dine at The Stissing House or get pizza or burgers and don’t forget to visit the Stissing Cultural Center for a concert or a play. Come take a look!
Courtesy: George T Whalen Real Estate
845-677-5076
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.
Whether for starting out retirement or weekend use, 48 Woodside Street is an efficient, move-in-ready home. Pine Plains offers a number of attractions from fine dining at the Stissing House, or a relaxing kayak paddle on Thompson Pond. Nearby hiking trails offer options such as the Stissing Fire Tower, a challenging local favorite, and the Thompson Preserve an easy woodland stroll around a protected sanctuary. Additionally, the Lions Club Park provides a recreation field, frontage on Thompson Pond a with swimming area. Woodland Street is part of a network of streets ideal for walking and is close to the Pine Plains School's track and fields.
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!
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.
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.
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.
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.
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.
