Pine Plains Homes with Private Parking features

Welcome to Pine Plains, New York, a charming community that seamlessly blends rural tranquility with modern conveniences. Nestled in the picturesque Hudson Valley, Pine Plains is renowned for its top-notch school district, which prides itself on fostering a nurturing environment for students of all ages. The Pine Plains Central School District is dedicated to academic excellence, offering a comprehensive curriculum that prepares students for future success. With a strong emphasis on both academics and extracurricular activities, families can rest assured that their children are receiving a well-rounded education in a supportive setting.

As you explore homes in this delightful area, you'll find a range of properties that cater to diverse lifestyles. One of the standout features of many homes in Pine Plains is the availability of private parking. Whether you have a growing family, enjoy entertaining guests, or simply appreciate the convenience of having your own dedicated space, homes with private parking make life easier. No more worrying about street parking or navigating crowded lots—your vehicle will always have a safe and secure spot right at home.

Pine Plains offers a unique blend of small-town charm and modern amenities, making it an ideal place to call home. With its friendly community, excellent schools, and beautiful homes with private parking, it’s no wonder that families and individuals alike are drawn to this enchanting corner of New York. Discover your dream home in Pine Plains today and experience the perfect balance of comfort, convenience, and community!

Newest Pine Plains Homes with Private Parking features

$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

$585,000

3 Beds ⋅ 3 Baths ⋅ 998510 MLS

Perched up high with lovely distant views of the mighty Catskill Mountains, this Classic Country Cape Cod offers room for everyone. As you pull up your meandering, private drive you'll be welcomed by the classic rocking chair porch inviting you for conversations and lemonade. Enter the foyer to find a formal sitting room ready for you to cozy up by the fireplace with your favorite novel. The Eat in Kitchen and Formal Dining boasts plenty of space for entertaining with Breakfast Bar and sliders to the deck for dining with nature. A Den/ Office space with oversized windows and Pellet Stove makes working from home so nice. A Huge Primary Bedroom with En-suite and California style closet completes the first floor. On the second floor, you'll find a sweet, little sitting area, a perfect place for your private library. An extra-large Guest Room with Dormer and Catskill Mountain view. Another large bedrooms & Office Space. All 3 rooms share a nice sized Full Bath. The Bonus Room would be a great artists studio, yoga room, or media room. The Full, Unfinished Walk Out Basement with utilities and plenty of storage has ample space for rec room or even in law suite. Potential in place for Two Car Garage. A huge deck perfect for a big party has a charming Pergola and access to an ABG pool for summer fun. Set on over almost 3 Park-Like acres of Park Like land this rare find offers so much for the money. Quick stroll to Elizaville Deli and Diner and even Roadside Rooster for ice cream. 10 minutes takes you to Red Hook, Rhinebeck and TSP and all the wonderful things that make the Hudson Valley great!

1763 County Route 19, Red Hook

$575,000

3 Beds ⋅ 4 Baths ⋅ 997897 MLS

Wake up to beautiful lake views from nearly every room, abundant natural light, and the peaceful beauty of one of the Hudson Valley's premier private lake communities. Designed by renowned architect Steve Haas, this exceptional contemporary waterfront home offers 3 bedrooms and 3.5 baths, with each bedroom featuring its own en suite bath, including a convenient first-floor bedroom suite ideal for guests or one-level living. Whether you're searching for a full-time residence or an effortless weekend retreat, this home offers the perfect balance of comfort, style, and privacy. Walls of glass frame the lake while filling the home with natural light throughout the day. The dramatic living room features soaring cathedral ceilings, a striking wood-burning fireplace, and generous space for entertaining, while the chef's kitchen with granite countertops flows seamlessly into the dining area, creating an inviting setting for everyday living or hosting friends. A screened porch overlooking the lake provides a wonderful place to enjoy morning coffee, unwind after a day on the water, or host dinner with friends while taking in the ever-changing views. Just off the kitchen, a private courtyard offers additional outdoor space for container gardening, a fire pit, or simply relaxing. Life here is about enjoying the Hudson Valley—not maintaining a home. Residents enjoy kayaking and swimming on the lake, tennis, a beautifully maintained community pool, and peaceful tree-lined roads perfect for walking or biking, all within an upscale community known for its exceptional setting and meticulously maintained grounds. The monthly association fee reflects the exceptional level of services provided and extends well beyond what is typically included in most communities. In addition to maintaining the pool, tennis courts, private roads, landscaping, snow removal, and common areas, the association also assumes responsibility for many exterior maintenance and replacement items that are traditionally the homeowner's responsibility. The result is a true lock-and-leave lifestyle, allowing you to spend more time enjoying the lake and less time managing the ongoing upkeep of a home. Offered fully furnished, this turnkey home is ready to enjoy from day one. Ideally located just 25 minutes from Hudson's Amtrak station and within easy reach of the Wassaic Metro-North station, owners enjoy two convenient rail options for traveling to and from New York City. Rhinebeck, Pine Plains, the Berkshires, Tanglewood, the Taconic State Parkway, and countless Hudson Valley destinations are all nearby, making this a rare opportunity to enjoy one of the Hudson Valley's most desirable lakefront lifestyles.

322 Arcadia Drive, Ancramdale

$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

$5,400,000

3 Beds ⋅ 4 Baths ⋅ 956925 MLS

Perched atop 40.9 private acres, this exceptional custom-built estate offers unrivaled privacy and sweeping panoramic views of the Catskill Mountains. Blending timeless craftsmanship with modern luxury, this hilltop retreat embodies refined living in a breathtaking natural setting. Inside, antique teak flooring flows throughout the home, adding warmth and character to every space. The open floor plan features a gracious living room that opens to a library with a fireplace and a full bath, creating an inviting centerpiece for both relaxation and entertaining. At the heart of the home, the eat-in kitchen is both functional and striking, featuring a scullery and a distinctive modern Rumson fireplace. The kitchen opens effortlessly onto a stone terrace and pergola, offering a breathtaking setting for alfresco dining while overlooking beautifully landscaped gardens that evolve with the changing seasons. Adjacent, the formal dining room provides a refined space for hosting memorable gatherings. The lower level includes three bedrooms and four full baths, along with a music salon featuring expansive glass doors that open to a stone terrace with breathtaking panoramic views. Additional amenities include a wet bar, laundry room, and wine cellar, offering both convenience and luxury. A detached two-car garage complements the home’s timeless architecture while adding everyday practicality. Experience the epitome of serenity, artistry, and mountain living in this extraordinary hilltop estate—where every sunset paints a masterpiece across the western sky.

1135 Duell Road, Stanfordville

$3,995,000

10 Beds ⋅ 7 Baths ⋅ 953909 MLS

Set far back from one of the Hudson Valley’s most prestigious and scenic roads, this stunningly restored 1830s colonial farmhouse is a masterclass in combining historic charm with sophisticated living. Situated in the heart of the pastoral Shekomeko Valley on just under 10 pristine acres, this property offers ultimate privacy surrounded by large, rolling farms and protected acreage. Classic white clapboard siding and a welcoming front porch set the stage for a home that seamlessly blends 19th-century soul with modern amenities. Step onto original wide-plank flooring and admire the stunning, exposed hand-hewn beams. An oversized living room features a wood-burning fireplace and panoramic views from three exposures, with French doors leading to the expansive property. The formal dining room boasts an additional fireplace and two large china closets. The professionally equipped kitchen includes dual sinks, a premium professional range, a built-in refrigerator, and a sunny, south-facing breakfast room with pastoral views. A convenient butler’s pantry and powder room are also included on this level. Head upstairs to four bedrooms (two with fireplaces) and three bathrooms. The main house includes a fully equipped 3-bedroom apartment with a separate entrance—perfect for guests or staff. The property is a true compound, designed for both entertainment and flexibility. A fully outfitted barn includes a 3-bedroom apartment, a gym with a sauna, laundry, a workshop and a very large storage room which can easily be converting into more living space. Other buildings include another barn/workshop, a yoga studio, a 2-car detached garage with a storage loft, and a 60' equipment shed. This parcel offers endless potential for hobby farming, horses/livestock, or creating a private, quiet home office. Located in the desirable Shekomeko Valley, this property offers a rare mix of secluded tranquility and easy access to nearby towns.

1515-1517 Route 83, Pine Plains

$485,000

4 Beds ⋅ 3 Baths ⋅ 924504 MLS

A Home with a view of Stissing Mountain! Enjoy gorgeous sunsets all year long from your front door. 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!

82 Lake Road, Pine Plains

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