Pine Plains Homes with Off Street Parking features

Pine Plains Homes with Off Street Parking features

Welcome to Pine Plains, New York, a charming small town that beautifully balances the tranquility of rural living with the conveniences of modern life. Nestled in the heart of Dutchess County, Pine Plains is renowned for its tight-knit community, picturesque landscapes, and, most importantly, its exceptional school district. The Pine Plains Central School District is dedicated to providing a nurturing and stimulating environment for students, fostering academic excellence and personal growth. With a focus on individualized learning, dedicated educators, and a variety of extracurricular activities, families can feel confident that their children are receiving a top-notch education.

In addition to its strong educational foundation, Pine Plains offers a range of residential options that cater to diverse lifestyles. One of the standout features of many homes in this area is off-street parking, a highly sought-after amenity that enhances convenience and safety. Imagine coming home after a long day to a peaceful neighborhood where you can park your vehicle right on your property, free from the hassle of street parking. This feature not only adds to the overall appeal of the homes but also provides peace of mind, especially for families with children or those who frequently entertain guests.

Whether you're drawn to the area's natural beauty, the quality of the local schools, or the comfort of homes with off-street parking, Pine Plains is truly a hidden gem in New York State. Discover the warmth and charm of this community, where you can build lasting memories and enjoy a fulfilling lifestyle. Your dream home awaits in Pine Plains!

Newest Pine Plains Homes with Off Street Parking features

$445,000
3 Beds ⋅ 2 Baths ⋅ 1029261 MLS
Tucked away off the main road, this property is situated on a private road near Hunns Lake. The former fishing cottage is cozy and quiet on 1.2 acres, with mature trees, lawns and meadows with western sunset views. The entryway leads to a windowed sitting room which opens up to the main pine paneled living room, lined with an oversize picture window with sliders. A stone wood burning fireplace with insert provides a great centerpiece and two cords of wood are ready for next season. Flooring is currently painted with a striping trim. Double pane thermal windows with screens are throughout the house. The open country kitchen has wide plank pine floors and countertops with plenty of cabinet storage. The dining area includes two sets of glass slider doors leading out to the spacious two level Trex redwood decking overlooking the pool. A deluxe propane grill with oven and burner is also included. There is a full bath with double sink and tub with shower in addition the laundry. A one car garage is also on this level. Upstairs is the primary bedroom with multiple window exposures. A brand new full bathroom features a beautiful soaking tub. There are two more bedrooms/office also having two window exposures. Furnace, Oil Tank, Water Heater and Pool Pump are new from 2025. The property on one side and the rear is buffered by wide open land/forest. 50 acre Hunns Lake is nearby, and is a great 2 ½ mile walk around it. This is nearby to the villages of Millbrook, Pine Plains, Rhinebeck, Millerton and more. All provide shopping, dining, and overall country recreation. The Wassaic Metro North train station is just 18 minutes away; all this just two hours from NYC. Welcome to the Hudson Valley!

26 Hunns Lake Place, Stanfordville
$1,850,000
3 Beds ⋅ 4 Baths ⋅ 1022485 MLS
A c1865 Italianate farmhouse set back from the road under mature willows and maples, with the arched dormer, bracketed eaves, and double-leaf paneled front door that mark the period. The house has been kept close to original — wide pine plank floors throughout, tall windows, a carved wood mantel with a green marble surround in the living room — while the systems underneath it have been fully updated. Main level- Double front doors open to a side stair entry hall with original pine flooring and mud room space for your jackets and shoes. The living room holds a bay window, a period mantel, and leads through to a green-walled study with a sitting area and desk. The kitchen and dining room are the result of a recent addition. The kitchen features black cabinetry, brass hardware, butcher block counters, and a zellige tile backsplash and range hood; a wall of windows over the sink looks out to the willows. A blue-walled family room and adjoining dining area spills out to the back patio for easy gathering and entertaining. A full bath with laundry and main floor bedroom complete the level. Upper levels- The second floor has 2 bedrooms, one beautifully appointed at the front of the house, with a full hall bath. The primary suite is anchored by a wall of built-in bookshelves, has a walk in closet and en suite bath. A finished third-floor room under the eaves, lit by a skylight, works as a sleeping loft or playroom and includes a full bath. Grounds A deep, tree-lined lot with mature plantings, a boxwood-edged path to an in-ground salt water pool with a stone patio, bordered by perennial beds. There is a small accessory dwelling for an office, art studio or yoga room. Location On County Route 19 in the Town of Clermont, Columbia County — between Red Hook and Hudson, with easy access to the Taconic State Parkway and the Amtrak stations in Rhinecliff and Hudson.

1788 County Route 19, Red Hook
$429,000
3 Beds ⋅ 1 Baths ⋅ 1026705 MLS
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!

75 Birch Drive, Pine Plains
$799,000
3 Beds ⋅ 3 Baths ⋅ 1011393 MLS
Beautifully reimagined 1924 home blends character with modern comfort and thoughtful design. Completely renovated in 2020 the residence offers 2,304 finished square feet with 3 bedrooms and 3 full baths. Vaulted ceilings, exposed beams abundant windows and an open-concept floor plan create a sense of beauty and spaciousness. The main level features warm wood floors, radiant heat throughout, and seamless flow between the living, dining, and kitchen areas. A dedicated office space provides flexibility for remote work or creative pursuits. The first floor primary suite serves as a private sanctuary, complete with its own deck overlooking the peaceful backyard. A second deck extends the dining and kitchen areas creating the perfect setting for outdoor dining, entertaining, or simply enjoying the tranquil surroundings. The finished walkout lower level expands the home's versatility with polished concrete floors, radiant heat, a full bath, a bedroom, a family room, and a kitchenette area. With two separate entrances on the lower level this area is ideal for entertaining, guests, extended family, or multi-generational living. Outside, a stream winds through the property, with a bridge providing access to both sides of the land. Durable hardwood siding, a 50-year shingle roof, and a new propane boiler installed in 2026 offer peace of mind and long-term value. Easy access to the Taconic State Parkway and conveniently located near the villages of Red Hook, Rhinebeck, Pine Plains, and Hudson, placing some of the Hudson Valley's most desirable destinations within easy reach.

82 Near Road, Red Hook
$799,000
3 Beds ⋅ 2 Baths ⋅ 1007119 MLS
A 1949 original, 153 Near Road was fully reimagined in 2021. The house is sited on two acres off a county lane, yet is a short distance to Hudson, Red Hook, Pine Plains with easy access to the Taconic Parkway. The first floor features an open concept, the kitchen, dining and living spaces flow together without interruption, anchored by a kitchen island and warmed by a wood stove. Flooded with natural light through picture windows the light wood floors catch and reflect the sunlight throughout the day. A first floor bedroom suite offers privacy and ease, featuring a stunning walk in shower and a laundry room tucked nearby, everything one needs on one level. Upstairs, two bedrooms feel suspended in the tree canopy. The window above the soaking tub perfectly frames it, making it an ideal spot for a moonlit soak. Enjoy the stream on a hot summer day and later relax under the stars around the firepit. The electrified outbuilding is a great space for an office or artist studio. One won't have to worry about using additional electricity, as the solar panels lighten the footprint.

153 Near Road, Red Hook
$850,000
1008519 MLS
Commercial property with Multi-Use potential in Pine Plains, NY. This versatile commercial property boasts a variety of uses, making it of interest to investors, entrepreneurs and businesses alike. With two apartments, two office spaces, dedicated studio areas and a spacious workshop area with 5 bays with overhead doors. This property offers the perfect blend of residential and commercial functionality with potential for showrooms. Hardwood floors throughout and a new roof. Hard to find commercial property.

2773 Church Street, Pine Plains
$875,000
3 Beds ⋅ 2 Baths ⋅ 1002917 MLS
Early house with charming changes. All updated. Overlooking stream and pond. On 13+ acres. Meadows and woodland walks. Charming old apple orchard. 3 bedrooms, primary bedroom on ground floor. 2 baths. Fireplace in living room. Swimming pool.

74 Willow Brook Road, Clinton Corners
$1,275,000
3 Beds ⋅ 3 Baths ⋅ 987704 MLS
A very special living and investment opportunity. Create an exceptional lifestyle in this well-preserved 1968 brick mid-century modern 3,670 sq ft one-level residence, complete with all comforts and amenities. Boasting a unique additional 2,152 sq ft attached indoor pool with floor-to-ceiling bay windows, enjoy sweeping jetliner views spanning more than 30 unencumbered miles of rolling hills to the south. Thoughtfully designed with seamless indoor-outdoor circulation and plenty of storage space, this home feels fitting for one or many. It magically transforms from a quiet writer's retreat into a vibrant family home or your private entertainment hub. Solidly built atop a hill, the easy-access bungalow-style layout features 3 bedrooms and 2 bathrooms on one side, and generous communal spaces on the other--including a living room, an open kitchen with dining area, and a large sunny room ideal for use as an office or additional living space. The island kitchen showcases custom-built original Quaker Maid maple cabinets paired with a state-of-the-art pantry. The original mid-century modern carefully preserved design contributes to the home's authentic historical charm while modern conveniences such as central air conditioning, high-speed internet, and a multi-point alarm system provide comfort. The large 1,800 sq ft heated basement includes a second kitchen area with double sink, countertops and cabinets, a full bathroom, laundry, utility room, and ample storage, ready to become a recreational space when adding a ping-pong table, a pool table and a movie screening area. An attached garage with additional workshop gives direct interior access to the house through a mudroom featuring bluestone floors and cedar walls. Swim year-round in the heated indoor kidney-shaped pool equipped with saltwater system & dedicated propane furnace; the solid brick construction includes a newer roof, massive industrial beams & renovated hardwood ceiling. Vinyl liner was recently replaced. Huge yoga deck facing the view. Property has two wells: one for the main house and a second dedicated to the pool and the garden's automatic irrigation system. The fenced vegetable garden sits just steps from the kitchen. Other practical touches include an automatic generator, outdoor spigots, & exterior outlets. The blacktop driveway makes snow removal quick and easy, while the parking area easily accommodates eight vehicles for pool parties or BBQs. Thanks to the elevated location, cell phone reception is strong. In-ground power lines enhance the elegance of the park-like setting, with its maintained lawn and mature trees offering plenty of outdoor space to roam after your daily swim. The house and grounds are easy to maintain. Use the large detached powered shed for lawn equipment storage, or convert it into a studio. Adding to the property's versatility, the 4.23 acres are already subdivided into two parcels with separate tax bills: the upper 2.23-acre parcel includes the residence while the lower 2-acre parcel is currently zoned as residential vacant land. This property has a renewable two-year Short-Term Rental (STR) permit and is currently operated successfully as an STR for half the year. The property also offers tremendous solar potential. Conveniently located less than a mile from the Taconic State Parkway (yet you cannot hear it), and only a 1hr 45mn drive from New York City, this peaceful and secluded residence makes the perfect weekend or vacation home. Pick up your guests or park at the Rhinecliff or Poughkeepsie train stations - respectively 30mn & 25mn away - or enjoy a scenic 1 hr 50 mn train ride along the Hudson River to the city. Own your own hill with million-dollar views, enjoy it as a primary luxury residence, a seasonal work-from-home getaway, or generate income with this turn-key piece of paradise. Included adjacent parcel address is 68 Ridge Rd Parcel ID 1352006569128825380000.

68-78 Ridge Road, Clinton Corners
$489,000
4 Beds ⋅ 2 Baths ⋅ 999436 MLS
Step into the charm and character of a bygone era with this spacious early-1900s Colonial-style home located in the heart of the hamlet of Pine Plains. Offering over 3,000 square feet of living space, this 4-bedroom, 1.5-bath residence sits on approximately 0.47 acres and is filled with history, warmth, and timeless architectural details. Once home to both the town pharmacy and library, this unique property blends rich local history with classic Hudson Valley charm. Inside, you’ll find stunning original woodwork and trim, oversized rooms, high ceilings, and beautiful hardwood floors throughout — long protected beneath carpeting for many years and now ready to shine once again. The two-story home offers endless potential for restoration, modernization, or simply enjoying its authentic character as-is. A large barn located behind the home provides excellent storage, workshop space, studio potential, or future creative use. Perfectly situated in the center of town, the property is walkable to local restaurants, the post office, pharmacy, and other village conveniences. Outdoor enthusiasts will appreciate the nearby hiking and biking trails, while commuters and weekend travelers will love being just approximately 30 minutes from both the Amtrak station and the Metro-North Railroad station in Poughkeepsie. Conveniently located between Rhinebeck, Hudson, Millbrook, and Millerton, this home places you in the center of some of the Hudson Valley’s most desirable destinations. A rare opportunity to own a piece of Pine Plains history with space, character, and incredible potential.

7786 S Main Street, Pine Plains
$1,250,000
5 Beds ⋅ 3 Baths ⋅ 998694 MLS
Nestled on a country road in West Pine Plains, the Historic Hanlon Hill Farmstead offers a rare opportunity to own a piece of history. This 87-acre property, spanning five parcels, has been in the Hanlon family for six generations. The centerpiece is an 1840s eyebrow colonial home, set back from the road for ultimate privacy. As you enter the farm, you'll pass a serene pond and a charming one-bedroom guest cottage featuring wood floors and a beautiful brick fireplace. Currently rented for $1,000 per month, the tenant covers all utilities. The main house is a lovely blend of historic charm and modern comfort, with 4 bedrooms, 2 bathrooms, and gorgeous wide-board wood floors throughout. Nature lovers will appreciate the meadows, abundant woodlands, and diverse wildlife that surround the property. Farm roads wind through the land, leading to the highest points, where you can take in breathtaking sunset views. This land offers incredible development potential, with standing hardwoods ready for harvest, and the barn—24’ x 36’ with a metal roof—could easily be transformed into horse stalls or used for other farming needs. Whether you're an investor or an outdoor enthusiast, this property has endless possibilities. It’s ideal for hiking, hunting, or any outdoor activity you can imagine. The historic colonial features a large, covered front porch with its original door, opening into a grand staircase. To the right, a spacious living room boasts a large stone fireplace, and a small galley kitchen sits adjacent. To the left, you'll find a formal dining room and a bedroom with an antique bath, plus the main kitchen, complete with a wood stove. Upstairs, there are 3 bedrooms and a modern, fully-tiled bathroom with both a tub and shower. A cozy office or nursery is located off the largest bedroom. A three-season porch overlooks the meadows and orchard, offering a peaceful spot to relax. The property also includes a creamery, a smokehouse, and stunning stone retaining walls that add to its rustic charm. Conveniently located just off the Taconic Parkway, this farm is an easy drive to Rhinebeck, Red Hook, and Pine Plains. Whether you're looking for a serene retreat, a development opportunity, or a place to pursue farming, this historic property offers something for everyone.

303 Hicks Hill Road, Stanfordville
$1,649,000
5 Beds ⋅ 4 Baths ⋅ 991832 MLS
A meticulously restored and turnkey farmhouse, thoughtfully reimagined for modern living while honoring its architectural character, spans the picturesque landscape of Dutchess and Columbia Counties. A stunning bluestone courtyard, framed by handcrafted stone walls sourced from the property itself, creates an unforgettable outdoor setting—equally suited for elegant entertaining, intimate al fresco dining, or quiet evenings beneath the stars. The result is a home that feels timeless, sophisticated, and effortlessly relevant for today's lifestyle. Inside, you will find five bedrooms and four full baths that unfold across a series of beautifully scaled interiors. Expansive Primary first floor ensuite with radiant floors, gas fireplace, balcony with walkout to upper deck. Wide plank floors, exposed hand hewn beams, and original millwork throughout the home speak to a level of craftsmanship seldom found today. The living spaces are both flexible, refined and inviting. Designed for a seamless balance of everyday comfort and sophisticated entertaining. The open kitchen was remodeled with new butcher block countertops, top of the line appliances, new center island and coffee bar with wine fridge. Take a step down to the sunroom with exceptional light, where French doors blur the line between indoors and courtyard living. A beautifully scaled flex room above the garage, offering endless versatility. Numerous improvements include new roof, windows, water filtration system, new front double entry doors and much more. Ideally sited for seamless access to the Taconic Parkway, the villages of Rhinebeck and Red Hook, and the Rhinecliff train station. This home is where history, architecture and landscape converge in a singular and irreplaceable offering.

1429 Jackson Corners Road, Red Hook
$600,000
3 Beds ⋅ 2 Baths ⋅ 991745 MLS
There's a quiet sense of arrival at 287 Hunns Lake Road, where the pace softens and the setting begins to shape the rhythm of the day. Tucked along nearly three acres of lawn and woodland in the heart of Dutchess County, this thoughtfully updated home offers something increasingly rare in the Hudson Valley: room to breathe, a layout that just works, and a location that puts the countryside and the region's best at your doorstep. Mornings often start out front, where the covered porch invites you to settle in with a cup of coffee and ease into the day — rocking-chair-ready and framed by mature trees, the kind of porch that turns a routine into a ritual. Inside, the home flows easily from one room to the next, anchored by a brick wood-burning fireplace that brings warmth and character to the heart of the living room. The kitchen surprises in all the right ways, with rich cherry cabinetry, granite countertops, stainless appliances, a peninsula with seating, and a large window above the sink that frames the backyard in green. Two comfortable bedrooms sit on the main level, sharing a beautifully updated full bath with a double vanity. A main-floor laundry adds everyday ease. Upstairs, the private primary suite feels tucked into the trees, with its own ensuite bath and an enormous attic just beyond — offering serious storage or future expansion potential. Out back, a wide deck extends the living space into the outdoors, made for slow afternoons, summer cookouts, and evenings that linger as the light fades through the trees. Beyond it, the lawn rolls gently toward the woods, with a fenced area ready for a garden or dog run and plenty of room to imagine a fire pit, pool, or orchard. An attached two-car garage round out the practical side. And then there's the location. Stanfordville sits in the sweet spot of Dutchess County, surrounded by working farms and some of the Hudson Valley's most celebrated destinations — Millbrook Vineyards, Milea Estate, Clinton Vineyards, and Taconic Distillery are all minutes away, alongside Thompson Pond Preserve, the Harlem Valley Rail Trail, and the village charm of Rhinebeck and Millbrook. The Taconic Parkway keeps everything well within reach. Turn-key inside, generous outside, and rooted in one of the Hudson Valley's most beautiful pockets — 287 Hunns Lake Road is ready to welcome you home.

287 Hunns Lake Road, Stanfordville
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