Pleasant Valley Homes with Attached Parking features

Welcome to Pleasant Valley, New York, a hidden gem nestled in the heart of Dutchess County. This charming town is known for its picturesque landscapes, friendly community, and a serene atmosphere that makes it an ideal place to call home. With its rolling hills and lush greenery, Pleasant Valley offers residents a perfect blend of rural charm and modern convenience. Enjoy the tranquility of nature while still being just a short drive away from the vibrant cities of Poughkeepsie and Beacon, where you can explore local dining, shopping, and cultural attractions.

Pleasant Valley is not just about stunning scenery; it also boasts a variety of homes that cater to diverse lifestyles. One of the standout features of many properties in this area is the availability of attached parking. Imagine the convenience of stepping out of your front door and into your vehicle without the hassle of searching for a parking spot. This feature is particularly valuable in a community where outdoor activities abound, making it easy to enjoy everything from hiking trails to local parks.

Whether you’re a first-time homebuyer or looking to upgrade, Pleasant Valley’s real estate market offers a range of options that include cozy single-family homes, spacious townhouses, and modern condominiums. With attached parking, you can enjoy the ease of access while embracing the warmth of this welcoming community. Come discover your dream home in Pleasant Valley, where comfort and convenience meet in perfect harmony.

Newest Pleasant Valley Homes with Attached Parking features

$499,000

3 Beds ⋅ 2 Baths ⋅ 1047289 MLS

Welcome to 10 Meadow Lane, where generous living space, thoughtful updates, and inviting indoor and outdoor amenities come together on over an acre of beautifully landscaped grounds located in the heart of Pleasant Valley and within the Arlington School District. This spacious split-level home offers 3 bedrooms, 1.5 baths and almost 2200 finished SQFT of flexible living space designed for everyday comfort and effortless entertaining. A covered rocking chair front porch, attractive landscaping, and an expansive lawn create a warm first impression. Step inside to a bright and welcoming main level featuring an open, airy layout, crown molding, attractive flooring, and a beautiful bay window that fills the living room with an abundance of natural light. The spacious living and dining areas flow seamlessly together, providing plenty of room for relaxed daily living, holiday gatherings, and memorable celebrations. Renovated in 2020, the kitchen features white shaker cabinets, granite marble countertops, SS appliances, a subway tile backsplash, luxury vinyl plank flooring, ample counter space, and a convenient breakfast bar. Just beyond the main living areas, the sunroom was updated in March 2023 with luxury vinyl plank flooring, high efficient heat pump and surrounded by oversized windows, offering a peaceful and versatile space for morning coffee, reading, entertaining, exercising, or simply enjoying views of the backyard. Upstairs, three generously sized bedrooms feature oak flooring and abundant natural light. The primary bedroom includes a walk-in closet with extensive built-in cabinetry and drawers for exceptional storage and organization. The updated full bath offers a soothing neutral palette, soaking tub, tiled shower surround with decorative accents, and a rainfall-style shower head. The expansive lower-level family room was renovated in the fall of 2024 and offers an impressive amount of additional living space. A classic brick surround wood burning stove creates a warm focal point, while recessed lighting, multiple windows, and updated flooring enhance the room’s welcoming atmosphere. With plenty of room for oversized seating, a home theater, game area, playroom, gym, or home office, this level can easily adapt to your needs. A conveniently located half bath adds even more functionality. Outdoor living is one of the property’s standout features. Installed in the summer of 2023, the 36-by-18-foot above-ground pool features a 7-foot deep end and is surrounded by an expansive deck—creating the perfect setting for summer barbecues, pool days, entertaining, or relaxing in the sun. The fully fenced in backyard offers plenty of space to entertain, while mature trees provide a peaceful and private wooded backdrop. The home has tons of additional improvements include a new roof completed in 2019 with a transferable warranty, a washer and dryer added in February 2021, whole-house mini-splits for efficient heating and cooling installed in April 2023, owned solar panels installed in 2023 and new garage doors and WiFi openers installed in January 2025. Additional highlights include custom closets and storage, a full finished lower level, updated laundry room and attached oversized 2 car garage with added storage room. Excellent location, conveniently located near schools, shopping, dining, parks, and major commuter routes, this home offers the space, ample updates, and outdoor amenities you have been waiting for, private yet relative to all, come see beauty of the Hudson Valley!

10 Meadow Lane, Pleasant Valley

$675,000

4 Beds ⋅ 3 Baths ⋅ 1045390 MLS

Perfectly situated at the end of a cul-de-sac, this cared for Colonial sits on a picturesque country acre, located in the Cambridge Estates. Thoughtfully updated and beautifully cared for, this home offers the perfect blend of comfort, space, and functionality. At the heart of the home is the beautifully updated kitchen, renovated just one year ago with a fresh, modern feel and plenty of space for everyday living and gathering. New flooring throughout the main level creates a cohesive look and seamless transition from room to room. Upstairs, the spacious primary suite features a private en-suite bath and generous walk-in closet. Three additional bedrooms and a full bath complete the second level, offering plenty of space and flexibility. The finished basement provides even more living space, offering plenty of flexibility for a recreation room, guest area, playroom, or home office. Complete with a bar and additional storage, it’s a versatile extension of the home with space to suit a variety of needs. Just off the family room, find a spacious 12' x 20' screened-in porch extends the living space outdoors, with direct access to the deck, pool and backyard. Enjoy the privacy of a peaceful setting while still being just minutes from popular destinations such as Eastdale Village, shopping, dining, and other local amenities.

18 English Way, Pleasant Valley

$425,000

3 Beds ⋅ 1 Baths ⋅ 1026953 MLS

This picture perfect, recently updated, 3 bedroom ranch home is located at the end of a cul-de-sac in a beloved neighborhood. The notably updated eat-in kitchen features gleaming granite countertops, stainless steel appliances, deep pantry, newer light fixtures and an additional matching curved entryway recently added for ease of use and accessibility. Complete with beautiful tile flooring and views of the mountains and meadow beyond the treelined backyard and expansive newer deck (2022). The brightly lit, spacious living room features hardwood floors and light streaming in from two sides. Enjoy three sizable bedrooms with well appointed closet spaces, a freshly painted bathroom with shower/tub combo, a walk-up attic that offers opportunity for additional expansion, a formal dining room with a stone wood-burning fireplace, an attached oversized garage heated with a pellet stove and a full basement with refinished floors that encompasses laundry, utilities and a secondary pellet stove heating system for the whole home in addition to the oil furnace. This home is tucked away; yet close to it all! Minutes to Rte 44 (0.5mi), Eastdale Village (2.5mi), Dutchess Rail Trail (4mi), Taconic State Parkway (5.5mi), Poughkeepsie MetroNorth Train Station (7 miles) and the Mid-Hudson Bridge.

67 Gleason Boulevard, Pleasant Valley

$575,000

4 Beds ⋅ 3 Baths ⋅ 1034490 MLS

Welcome to this spacious 4-bedroom, 2-bathroom contemporary home offering 2,780 square feet of thoughtfully designed living space on 2.24 picturesque acres within the Arlington Central School District. Blending timeless architecture with an inviting layout, this home offers the perfect balance of comfort, functionality, and privacy. A long driveway leads to the home, where mature trees, expansive lawns, and peaceful views create a private retreat. Step inside to discover a dramatic foyer that opens to generous living spaces filled with natural light. The formal living room features a beautiful bay window, while the spacious dining room is ideal for hosting family gatherings and holiday celebrations. The eat-in kitchen offers granite countertops, abundant cabinetry, and a walk-through design that flows seamlessly into the breakfast area and oversized family room. Centered around a cozy fireplace, the family room opens to a screened-in porch overlooking the backyard, creating the perfect space to relax or entertain in every season. The main level also includes a dedicated home office, a convenient laundry room, and direct access to the impressive attached 3-car garage, providing exceptional storage and everyday convenience. Upstairs, the expansive primary suite serves as a peaceful retreat with oversized windows showcasing tranquil views, generous closet space, and an ensuite bath complete with a soaking tub, separate shower, and dual-sink vanity. Three additional well-sized bedrooms and a full hall bathroom provide comfortable accommodations for family and guests. The full basement offers endless possibilities for future finishing, recreation, fitness, or additional storage. Outside, enjoy over two acres of beautifully maintained property that goes back down to the Wappingers Creek with open green space, mature landscaping, a fenced play area, and room for gardening, recreation, or simply enjoying the surrounding natural beauty. Additional features include central air conditioning, oil-fired forced hot air heat, drilled well, septic system, a frame exterior, and a full unfinished basement with 9 ft ceilings. Conveniently located just minutes from shopping, restaurants, parks, and commuter routes while offering the serenity of country living, this exceptional property is ready to welcome you home.

27 Patricia Drive, Pleasant Valley

$525,000

3 Beds ⋅ 2 Baths ⋅ 1033002 MLS

Welcome to this beautifully updated move-in ready home, perfectly situated at the end of a quiet cul-de-sac, offering unmatched privacy and a peaceful, wooded backyard setting. Whether you're enjoying your morning coffee in the beautiful three-season sunroom or relaxing outdoors, this property provides the tranquility you've been searching for. Inside, you'll find numerous high-quality updates completed within the last two years, including a completely renovated kitchen, brand-new main-level windows, and a new electrical panel for added peace of mind. The home also features fully paid-off solar panels, allowing the next owner to enjoy little to no electric bill. Additional improvements include a brand-new water softener and whole-house filtration system, ensuring comfort and convenience from day one. For added accessibility, the home is equipped with an elevator, making it ideal for those with mobility needs or anyone looking for long-term convenience. Combining modern upgrades, energy efficiency, exceptional privacy, and thoughtful features throughout, this home truly is the epitome of move-in ready. Don't miss the opportunity to own this one-of-a-kind property in a highly desirable, quiet neighborhood.

12 Talbot Drive, Pleasant Valley

$649,000

4 Beds ⋅ 4 Baths ⋅ 1026844 MLS

Welcome to 21 Straub Drive in Pleasant Valley, a spacious and versatile home offering 4 bedrooms, 3.5 baths, and a flexible floor plan. Nestled on a private lot ,this property combines peaceful country living with convenient access to major commuting routes. The home features generous living spaces designed for both everyday comfort and entertaining. Multiple living and gathering areas provide flexibility for today's lifestyle, while the layout offers possibilities for multi-generational living or guest accommodations. A bright and inviting three-season sunroom with French doors provides the perfect place to enjoy morning coffee, relax with a book, or take in views of the beautifully landscaped grounds. Step outside to your own private backyard retreat featuring a custom man-made pond with a stunning waterfall feature, creating a tranquil setting to relax, entertain, or enjoy nature year-round. A charming gazebo overlooks the picturesque setting, offering an ideal spot for outdoor dining, gatherings, or simply enjoying the peaceful surroundings. The private grounds offer a rare combination of serenity and usability. Ideally located close to the Poughkeepsie Metro-North Train Station and the Taconic State Parkway, this home provides an excellent balance of privacy and accessibility for commuters and weekend travelers alike. Whether you're seeking room to grow, or a peaceful Hudson Valley setting close to amenities and transportation, 21 Straub Drive presents a unique opportunity to enjoy the best of Pleasant Valley living. A property that truly blends comfort, flexibility, and outdoor enjoyment on a private lot in a non-flood zone, all in one exceptional package.

21 Straub Drive, Pleasant Valley

$445,000

3 Beds ⋅ 2 Baths ⋅ 1024143 MLS

Beautifully updated ranch, set on a tree-lined homesite in the Town of Pleasant Valley, offering the ease of one-level living with tasteful finishes throughout. The inviting floor plan features a welcoming entry foyer, hardwood flooring, sun-filled living room with bay window, and a bright kitchen with SS Frigidaire appliances and a Samsung refrigerator. The step-down dining room is perfect for entertaining and opens to a spacious tiered deck. The fully fenced backyard enjoys abundant sunshine throughout the year and features a gravel patio, fire pit, and level yard with plenty of space for a pool, play area, pets, or vegetable and floral gardens. The finished lower level adds valuable living space with a family room, laundry area, half bath, and utility/storage rooms. Additional highlights include energy-efficient replacement windows throughout, central air conditioning, newer rear roof, recessed lighting, 200-amp electrical service, retaining walls, and front walkway. Conveniently located just 5 miles from the Taconic State Parkway, 3.5 miles to the Eastdale Village, and 8 miles from the Poughkeepsie Metro-North Station. Move right in and enjoy all this exceptional home has to offer.

63 Martin Road, Pleasant Valley

$799,000

4 Beds ⋅ 3 Baths ⋅ 1017332 MLS

TO BE BUILT – The Vanderbilt Model Colonial on Over 3 Acres! This stunning 4-bedroom, 2.5-bath colonial offers the perfect blend of elegance and functionality. The thoughtfully designed main level features a formal living room and dining room, a spacious family room that showcases a gas fireplace and a wall of windows, seamlessly opening to the kitchen with quartz counters, a center island, and access to the deck—perfect for everyday living and entertaining. Upstairs, the luxurious primary suite offers tray ceilings, walk-in closets, and a spa-like bath with double sinks, and walk-in shower. Three additional generously sized bedrooms and a full bath complete the second level. The full unfinished basement provides ample storage and future potential. Built by a reputable local builder, this home includes quality finishes such as 9’ first-floor ceilings, elegant trim work, seamless gutters, 2 car garage and energy-efficient construction. Photos shown are of a previously built model with upgrades. Additional models and customization options available. Estimated build time is 6–8 months from permit approval. Ideally located just minutes to the Village of Pleasant Valley, Millbrook, the Taconic State Parkway, shopping, dining, and more—this is an opportunity you won’t want to miss!

991 Freedom Road, Pleasant Valley

$1,195,000

3 Beds ⋅ 3 Baths ⋅ 951502 MLS

Historic Barn Conversion Meets Modern Luxury in the Hudson Valley Tucked away along a quiet country road in Pleasant Valley, this extraordinary estate offers a rare opportunity to own a meticulously restored 19th-century barn conversion that seamlessly blends historic character with modern luxury. Originally two separate barns, the property has been thoughtfully reimagined into a one-of-a-kind residence and companion pool house, creating a private retreat unlike anything else available in the Hudson Valley. From the moment you arrive, the home’s timeless architecture tells a story. Inside, soaring vaulted ceilings, original hand-hewn beams, wide-plank floors, and authentic post-and-beam construction showcase the craftsmanship of a bygone era while providing the comfort and functionality today’s buyers expect. Expansive walls of glass flood the interior with natural light and frame views of the surrounding countryside, creating a seamless connection between indoor and outdoor living. The main residence offers warm, inviting living spaces designed for both everyday living and entertaining. Rich architectural details, exposed timber framing, and carefully preserved historic elements create a sense of authenticity rarely found in modern construction. Every room balances rustic elegance with refined finishes, resulting in a home that feels both sophisticated and welcoming. Complementing the main residence is a beautifully converted barn pool house, providing exceptional flexibility for guests, entertaining, creative pursuits, or a private wellness retreat. The outdoor spaces are equally impressive, offering a peaceful setting to relax, gather, and enjoy the natural beauty of Dutchess County. Located just minutes from Millbrook, Rhinebeck, Poughkeepsie, and the region’s renowned farms, wineries, restaurants, and outdoor recreation, this property delivers the best of Hudson Valley living while remaining easily accessible to New York City. Whether you’re searching for a luxury barn conversion, a post-and-beam home, a historic country estate, or a weekend retreat in the Hudson Valley, 101 Drake Road represents a truly rare offering where history, architecture, and modern comfort come together in perfect balance.

101 Drake Road, Pleasant Valley

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