Pine Plains Homes with Driveway Parking features

Welcome to Pine Plains, New York—a hidden gem nestled in the heart of the Hudson Valley. This charming town boasts a rich history and a vibrant community, making it an ideal place for families, retirees, and everyone in between. Surrounded by picturesque landscapes, Pine Plains offers an abundance of outdoor activities, from hiking and biking to exploring nearby parks and nature reserves. The local economy thrives on small businesses, artisanal shops, and farm-to-table restaurants, creating a warm and inviting atmosphere for residents and visitors alike.

One of the many appealing features of homes in Pine Plains is the availability of driveway parking. Imagine coming home to a beautiful residence with ample space to park your vehicles right outside your door. Driveway parking not only enhances convenience but also adds an extra layer of security for your vehicles. Whether you’re returning from a day of exploring the stunning Hudson Valley or simply commuting to work, having a dedicated parking space makes life just a little easier.

Many homes in Pine Plains come equipped with spacious driveways, allowing for multiple vehicles, recreational toys, or even a cozy outdoor seating area for weekend gatherings. This feature is especially valuable in a town where community and connection are paramount.

If you’re searching for a home that combines the charm of small-town living with modern amenities, look no further than Pine Plains. Discover your perfect sanctuary in this delightful town, where driveway parking is just one of the many reasons to call it home.

Newest Pine Plains Homes with Driveway Parking features

$1,650,000

3 Beds ⋅ 4 Baths ⋅ 1049798 MLS

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, Diningroom 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.

81 Tinker Hill Road, Pine Plains

$499,000

2 Beds ⋅ 2 Baths ⋅ 1049475 MLS

Welcome to 559 Lake Road in Pine Plains! Boasting direct views and access to Twin Island Lake, this beautiful property has it all, lake and mountain views! Whether you are looking for a lucrative investment, a dream summer getaway, or a year-round sanctuary, this home has it all. The entire front of the house features stunning, unobstructed lake views. Start your mornings on the covered porch sipping coffee, listening to the birds, and watching the wildlife on the water amidst beautiful perennial flowers. Inside, enjoy a bright, spacious open floor plan ideal for modern living. The layout includes a primary bedroom and bath with plenty of closets, plus a second bedroom and a flexible home office with a large closet, sleeps like a 3 bedroom. Step outside to hike up your own 4+ acres of private land, or drive just 15 minutes to enjoy the top-tier restaurants and entertainment in nearby Red Hook and Rhinebeck. All this peace and quiet is located under 2 hours from NYC via the Taconic State Parkway!

559 Lake Road, Pine Plains

$359,000

3 Beds ⋅ 1 Baths ⋅ 1028565 MLS

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.

2795 Church Street, Pine Plains

$799,000

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

$409,000

3 Beds ⋅ 2 Baths ⋅ 999870 MLS

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.

211 Sigler Road, Pine Plains

$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

$575,000

7 Beds ⋅ 5 Baths ⋅ 993929 MLS

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.

80 County Route 7, Pine Plains

$575,000

7 Beds ⋅ 5 Baths ⋅ 969056 MLS

This beautifully updated legal 2-family home seamlessly blends vintage charm with modern convenience, offering exceptional flexibility for multigenerational living, rental income, or guest accommodations. Located just 7 minutes from Pine Plains Village and set on a scenic lot with sweeping countryside views and a neighboring 200-acre farm, the property features meticulously maintained grounds, two storage sheds for garden tools and recreational items, and ample off-street parking. The main house offers 4 spacious bedrooms and 3 full baths, a large sunlit living room, a formal dining room, original hardwood floors, a grand staircase with the original banister, and a finished attic—perfect for a playroom, studio, or home office. The renovated kitchen features granite countertops, stainless steel appliances, an oversized island, tile flooring, and an electric fireplace, with a separate laundry room and an additional full bath located on the main level. The private second unit (or guest wing) is a legal 3 BR/2 Bth apartment and includes a first-floor primary bedroom with a walk-in shower, an open-concept living and dining area with beautiful views, two more bedrooms and a full bath upstairs, plus convenient second-floor laundry. Both units share a heated enclosed porch/mudroom for entry, while the main house also enjoys a formal front entrance with vintage appeal. Currently tenant-occupied on month to month contracts. Please contact the broker for rent roll, expenses, and additional details. A new 2000 gallon septic system was installed in 2021. Heating is provided by oil with central air in Unit 1, and mini-split systems were added to Unit 2 in 2023 for efficient year-round climate control. This is a truly unique Hudson Valley opportunity, perfectly positioned on the Ancram border and just two hours to Manhattan by car, or 20 minutes to Hudson for Amtrak access. There's so much to love! Come see for yourself! Photos have been virtually staged.

80 County Route 7, Pine Plains

$4,495,000

7 Beds ⋅ 4 Baths ⋅ 947632 MLS

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.

8032-8060 Rt-82, Pine Plains

$3,895,000

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

$149,900

932119 MLS

Attention investors & contractors! 4 Bedroom, 2.5 Bathroom Two Family Ranch on 2.4 acres in T/Pine Plains! Sold as-is. Buyer to pay NYS and any local transfer taxes. Offers with financing must be accompanied by pre-qual letter; cash offers with proof of funds. **Please see agent remarks for access, showing instructions and offer presentation remarks.**

245 Hicks Hill Road, 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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