Pleasant Valley Homes with Off Street Parking features

Welcome to Pleasant Valley, NY – a hidden gem nestled in the heart of Dutchess County! This charming town offers a perfect blend of serene countryside living and convenient access to urban amenities, making it an ideal place for families, retirees, and everyone in between. With its picturesque landscapes, vibrant community spirit, and rich history, Pleasant Valley captures the essence of small-town charm while providing residents with everything they need for a fulfilling lifestyle.

One of the standout features of homes in Pleasant Valley is the abundance of properties equipped with off-street parking. This thoughtful amenity not only enhances convenience but also adds a layer of safety and security for your vehicles. Imagine coming home after a long day to find your car parked just steps away from your front door, free from the hassle of street parking or crowded driveways.

Whether you’re seeking a cozy cottage, a spacious family home, or a modern townhouse, Pleasant Valley has a diverse range of real estate options to suit your needs. Many of these homes boast well-maintained yards, perfect for outdoor gatherings or enjoying a quiet evening under the stars. The friendly community atmosphere is complemented by nearby parks, walking trails, and local shops, making it easy to engage with your neighbors and enjoy the beauty of the Hudson Valley.

Discover the allure of Pleasant Valley today, where off-street parking is just one of the many features that make this town a wonderful place to call home. Experience the perfect balance of tranquility and connectivity in this delightful corner of New York!

Newest Pleasant Valley Homes with Off Street Parking features

$650,000

3 Beds ⋅ 3 Baths ⋅ 1044510 MLS

Set beautifully near the center of almost 8 private acres, this cherished home has been owned by the same family for nearly 50 years and offers a setting that invites you to slow down and enjoy the natural beauty that surrounds you. A picturesque pond, meandering stream and waterfalls create a peaceful backdrop, while thoughtfully positioned gardens and mature landscaping offer something beautiful to enjoy in every season. Spend quiet mornings listening to the sounds of the water, relax on the screened-in porch with your morning coffee or evening cocktail, or gather with family and friends on the stone patio. Inside, warmth and character continue with hardwood floors throughout, two wood-burning stoves and distinctive wood details that give the home its inviting feel. The kitchen is appointed with quartz countertops and a custom island with seating, while the dining room provides the perfect setting for everything from intimate dinners to holiday gatherings and entertaining. Designed for the ease of one-level living, the home offers three bedrooms and two full baths on the main level, including a primary bedroom with private en-suite bath, along with additional rooms offering flexibility for a den, home office, in-law space, guest accommodations or whatever best suits your lifestyle. A conveniently located laundry area just off the kitchen leads directly to the stone patio, making indoor-outdoor living easy. The lower level provides convenient access to the two-car garage, while an additional carport is ideal for storing equipment and machinery or providing a dedicated exterior workspace. Located in the Millbrook School District and just five minutes from the Taconic State Parkway, this special property offers a rare combination of privacy, natural beauty, character and convenience. After nearly five decades with one family, this much-loved home and property are ready for their next chapter.

2800 Route 82, 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

$175,000

3 Beds ⋅ 1 Baths ⋅ 1045313 MLS

Move-in ready 3BR home in Hickory Hills Estates with modern updates and a peaceful natural setting. This beautifully updated single-wide offers comfort, convenience, and outdoor charm all in one. Step inside to find new flooring, central air, and an open layout. The kitchen features stainless steel appliances and an oversized gas stove, perfect for anyone who loves to cook. The main bedroom includes double closets, and the full bath is upgraded with a dual vanity for added space and functionality. A sunny three-season room expands your living area and makes an ideal spot for morning coffee or evening relaxation. Outside, the corner lot provides extra room for activities, gardening, or simply enjoying the outdoors. There are two sheds for storage, plus a paved driveway with parking for three vehicles. A small brook runs along the back of the property, adding a natural backdrop you won’t find just anywhere. Located in Hickory Hills Estates, this home offers a quiet community feel while still being close to everyday conveniences. A great opportunity for affordable, comfortable living with thoughtful updates throughout.

65 Water Loop, Pleasant Valley

$174,900

2 Beds ⋅ 1 Baths ⋅ 1038005 MLS

DIAMOND IN THE ROUGH! HUGE POSSIBILITIES! RANCH HOME TWO BEDROOM, OFFICE OR NURSERY, DEN, LIVINGROOM. EAT IN KITCHEN WITH SLIDERS TO HUGE DECK. SPACIOUS ROOMS. BASEMENT AND WORKSHOP. PRIVATE YARD. ENJOY BACK YARD CREEK VIEWS. MATURE LANDSCAPING. CONVENIENT TO EASTDALE VILLAGE AND ALL AMENITIES. MIN. TO TSP AND TRAIN. WAPPINGERS CREEK FOR FISHING. KAYAKING AND SUMMER FUN.

4 Wilbur Road, 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

$549,000

4 Beds ⋅ 2 Baths ⋅ 1031549 MLS

809 Traver is a stunning Dutch Colonial, maintained with uncommon discipline and enduring craftsmanship. Built in 1764 as the Peter Flagler House, it was the town’s central tavern and meeting House. Set on just over an acre of mature landscaping, enjoy your heated swimming pool - or walk steps to the lovely town of Pleasant Valley. The home’s layout is classic in its proportions. A Dutch door opens to a central hall flanked by two large rooms. To the right, the country kitchen and dining room feature rough-hewn beams, built-in cabinetry, and a wide picture window overlooking the verdant yard. To the left, a large living room centers on a grand fireplace, with exposed brick and original wide-plank flooring. Upstairs are four bright bedrooms and a full bathroom. An addition was made that preserved the character of the home while adding more space: a second full bath, laundry, and a loft. This family room wing is bathed in light from walls of windows surrounding custom millwork. A second stairway leads to the library with cathedral ceilings — a room equally suited as a guest room, or studio. From your poolside view, take in the home's exquisite exterior: a deep columned porch spans the entire width of the house, a gambrel roof of new cedar shake, and replica historic windows peeking out from the dormers. Lush perennials of hydrangea and Rudbeckia create inviting zones for entertaining on the bluestone and brick patios. The yard also includes a detached one-car garage with an adjoining workshop and soaring ceilings — a perfect space for the artist or hobbyist, with potential for professional office use under a special use permit. Ideally located between Rhinebeck, Beacon and Millbrook in the highly sought after Arlington School District. The next steward of this spectacular home can enjoy award-winning dining, hiking, and the arts just 90 minutes to NYC and 20 min to Amtrak.

809 Traver Road, Pleasant Valley

$165,000

3 Beds ⋅ 2 Baths ⋅ 1007424 MLS

Spacious and beautifully maintained mobile home featuring 3 generously sized bedrooms, each with walk-in closets, and 2 full bathrooms. This inviting home offers an open and bright layout with large windows, elegant crown molding, recessed lighting, and numerous upgrades throughout. The cozy living room is highlighted by a fully functional wood-burning fireplace capable of heating the entire home during colder months. The well-appointed kitchen includes appliances, a gas range, abundant cabinetry, and ample counter space for meal preparation. Enjoy gatherings in the spacious dining area and eat-in kitchen, perfect for everyday living and entertaining. A wonderful opportunity to own a comfortable home with plenty of space and charm!

27 SHAGBARK, Pleasant Valley

$375,000

3 Beds ⋅ 2 Baths ⋅ 1020908 MLS

New to market. Relaxed living in lovely, quiet neighborhood. Won't last long. Low traffic, cul de sac road close to everything you need. Sold as package deal 48 Gleason Blvd: 3BR w/ full basement 48 Gleason Boulevard + next door 3BR w/ full basement 46 Gleason Boulevard for $750,000 total package price. Enjoy these 2 lovely homes on the top of the hill in beautiful & central Pleasant Valley. Live in one & rent the other, or purchase as easy investment in the land of no vacancies! Both 46 &48 Gleason Blvd are vacant right now. Many upgrades & updates throughout. Updated high efficiency combi boiler units in both homes. 48 Gleason has bathroom w/ shower upstairs and 1/2 bath in basement, washer/dryer hook up ready and walk out to backyard. Beautiful hardwoods throughout both homes with multiple ceiling fans, light fixtures, recessed lighting throughout. 46 Gleason is newly painted, move in tomorrow! Large basements: 46 Gleason has Full Bath upstairs and partially finished basement with bathroom/shower and walk out to backyard. Washer & Dryer in place and come with sale. 46 Gleason has new Stainless Steel appliances. With minimal finish work, both homes could offer extended family set ups due to downstairs bathrooms and walk outs. Adjoining backyards for possible compound. Great investment property in booming area. One well between both homes with strong water flow. Quiet, central neighborhood to Pleasant Valley, Poughkeepsie, Hyde Park, etc. Excellent property due to cul-de-sac and low traffic Gleason Boulevard. Call today! Sold as package deal with MLS#1020825

48 Gleason Boulevard, Pleasant Valley

$375,000

3 Beds ⋅ 2 Baths ⋅ 1020825 MLS

New to market. Relaxed living in lovely, quiet neighborhood. Won't last long. Low traffic, cul de sac road close to everything you need. Sold as package deal: 3BR w/ full basement 46 Gleason Boulevard + next door 3BR w/ full basement 48 Gleason Boulevard for $750,000 total package price. Enjoy these 2 lovely homes on the top of the hill in beautiful & central Pleasant Valley. Live in one & rent the other, or purchase as easy investment in the land of no vacancies! Both 46 & 48 Gleason Blvd are vacant. Many upgrades & updates throughout. Updated high efficiency combi boiler units in both homes. New Stainless Steel appliances in 46 Gleason. Beautiful hardwoods throughout both homes with multiple ceiling fans, light fixtures, recessed lighting throughout. 46 is newly painted, move in tomorrow! Large basements: 46 Gleason has Full Bath upstairs and partially finished basement with bathroom/shower and walk out to backyard. Washer & Dryer in place and come with sale. 48 Gleason has bathroom w/ shower upstairs and 1/2 bath in basement, washer/dryer hook up ready and walk out to backyard. With minimal finish work, both homes could offer extended family set ups due to downstairs bathrooms and walk outs. Adjoining backyards for possible compound. Great investment property in booming area. One well between both homes with strong water flow. Quiet, central neighborhood to Pleasant Valley, Poughkeepsie, Hyde Park, etc. Excellent property due to cul-de-sac and low traffic Gleason Boulevard. Call today! Sold as package deal with MLS#1020908

46 Gleason Boulevard, 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

$395,000

3 Beds ⋅ 3 Baths ⋅ 1008740 MLS

APPROVED SHORT SALE - Custom built A southern design home with a gable European roof. Features a two-story with open loft & sunlight throughout the entire 1st floor. The open floorplan with fireplace Designed with an open kitchen with stainless steel appliances and granite countertops. First floor offers the primary bedroom suite w/windows overlooking the backyard. Upstairs loft. 2nd level offers 2 beds/1 bath with attic access for room to grow! Two attics. Dual pump septic system. New septic gold pump & system pumped, needs one more gold septic pump. Heating upgraded with many new parts, but needs replacement on many items. A must see! Needs TLC. photos do not reflect current moving state. Moving 3 generations of stuff. Please note photos may not reflect current condition now. Landscaping has not been addressed.

181 David Drive, Pleasant Valley

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