Pleasant Valley Homes for Sale

Welcome to Pleasant Valley, New York – a hidden gem nestled in the heart of Dutchess County. Known for its picturesque landscapes and charming small-town atmosphere, Pleasant Valley offers a delightful blend of rural tranquility and modern convenience. With its scenic views, lush parks, and friendly community, it’s no wonder that this area is becoming increasingly popular among homebuyers seeking a serene lifestyle without sacrificing accessibility.

Pleasant Valley is conveniently located just a short drive from the vibrant cities of Poughkeepsie and Beacon, providing residents with easy access to shopping, dining, and cultural attractions. The area is also rich in outdoor activities, boasting numerous hiking trails, parks, and the stunning Hudson River nearby, perfect for nature lovers and outdoor enthusiasts alike.

As you explore the homes for sale in Pleasant Valley, you’ll find a diverse range of properties that cater to various tastes and budgets. From charming single-family homes with lush yards to modern townhouses with community amenities, there’s something here for everyone. Many homes feature spacious layouts, updated kitchens, and beautiful outdoor spaces, ideal for entertaining or relaxing after a long day.

The strong sense of community in Pleasant Valley is evident through its local events, farmers' markets, and friendly neighbors who take pride in their town. Whether you’re a first-time homebuyer, looking to downsize, or seeking a family-friendly neighborhood, Pleasant Valley is an ideal place to call home. Come discover the magic of Pleasant Valley – your dream home awaits!

Newest Pleasant Valley Homes for Sale

$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

$975,000

4 Beds ⋅ 4 Baths ⋅ 993619 MLS

Welcome to 125 Frost Hill Road, a spectacular Colonial offering over 4,000 square feet of beautifully finished living space on more than four private acres. Perfectly positioned atop a knoll, this exceptional home captures sweeping panoramic views while providing the ideal balance of luxury, comfort, and privacy. Step into the impressive foyer and immediately appreciate the home's bright, open feel and impeccable craftsmanship. Gleaming hardwood floors flow throughout the main level, while elegant moldings and chair rails enhance the formal living and dining rooms. Just off the foyer, French doors open to a private home office, creating the perfect space for today's remote lifestyle. Designed for both everyday living and entertaining, the heart of the home is the stunning chef's kitchen featuring granite countertops, a large center island, stainless steel appliances, and a spacious pantry. The kitchen opens to a breathtaking two-story family room anchored by a dramatic floor-to-ceiling stone fireplace, creating a warm and inviting gathering space. A second family room with a tray ceiling overlooks the resort-style backyard and heated in-ground pool, offering the perfect place to relax while enjoying the views. Take the second staircase upstairs to the luxurious primary suite, which is a true retreat, complete with a private sitting room or office, an enormous walk-in closet, and a spa-inspired bathroom designed for relaxation. A princess suite with its own private bath provides exceptional accommodations for family or guests, while two additional generously sized bedrooms share a beautifully appointed full bath. The expansive unfinished walk-out basement offers endless possibilities for future living space, a home gym, media room, or recreation area. Step outside and experience your own private resort. The heated in-ground pool is surrounded by an expansive patio and complemented by a large gazebo, creating an incredible setting for summer entertaining, family gatherings, or simply unwinding in complete privacy. Located just minutes from major commuter routes, hospitals, shopping, restaurants, colleges, and the many parks, wineries, hiking trails, and attractions the Hudson Valley is famous for, this remarkable property offers the perfect combination of peaceful country living and everyday convenience. This is more than a home—it's a lifestyle.

125 Frost Hill Road, Pleasant Valley

$510,000

4 Beds ⋅ 2 Baths ⋅ 1029452 MLS

Welcome to 38 Forest Valley Road a beautifully maintained and thoughtfully updated 4-bedroom, 2-bath home set on a scenic, level one-acre lot in the Arlington Central School District. The main level features an updated kitchen with granite counter tops, wood cabinetry, and stainless steel appliances. Comfortable dining area that opens to the deck overlooking the private backyard and above-ground pool perfect for entertaining or relaxing. This level also offers three spacious bedrooms, including a primary with a large closet, and two additional bedrooms plus an updated full bathroom with a tub. The finished lower level adds exceptional living space, with a comfortable den, a fourth bedroom, and a second updated full bathroom ideal for guests or a home office. The attached two-car garage includes room for a workshop, houses the washer and dryer, and offers a walk-out door to the backyard for added convenience. Outside, enjoy the private oasis, flat one-acre property with multiple decks and an above-ground pool, this property is made for outdoor gatherings and summer fun. This home has been extensively updated for comfort and efficiency, including: New roof with leased solar panels (2018) approximately 12 years remain on the lease, transferable to the new owner under current terms; current owners have not had an electric bill since installation, Reverse osmosis water system (2026), New hot water heater (2026), New windows with transferable lifetime replacement warranty, Peerless furnace (2020),Heat pump/inverter system (2024), Dry basement system (2005), Water softener (2007), Whole-house water filtration system, Attic exhaust fan and new attic stairs. Nothing to do but move in and immediately start enjoying this beautiful home!

38 Forest Valley Road, Pleasant Valley

$599,900

4 Beds ⋅ 2 Baths ⋅ 1031424 MLS

JUST REDUCED • MOTIVATED SELLER • YOUR DREAM HOME IS READY Welcome to 15 Rock Cut Lane, where every inch was thoughtfully reimagined in 2022 to deliver the perfect combination of style, comfort, and confidence. With virtually everything replaced—from the roof, siding, windows, foundation, electrical, plumbing, heating, and septic—you can skip the projects and start enjoying your new home from day one. Step inside to an open-concept living area bathed in natural light, featuring a cozy propane fireplace that flows seamlessly into a chef-inspired kitchen boasting rich cherry cabinetry, sleek marble countertops, and stainless steel appliances. Designed with flexibility in mind, this home offers over 3,300 square feet across three finished levels. Whether you need space for entertaining, working from home, a game room, or multigenerational living, this layout adapts to your lifestyle. The primary suite is a true retreat—offering the kind of luxury typically found in high-end resorts. Relax in your spa-inspired bathroom featuring dual vanities, a soaking tub, an oversized glass shower, and a spacious walk-in closet that completes the experience. With 4 bedrooms, 2 full bathrooms, and multiple indoor and outdoor spaces to enjoy, every member of the household has room to spread out while still feeling connected. And the location? It's just as impressive. Located in the highly desirable Arlington School District, you're only minutes from Eastdale Village, the Walkway Over the Hudson, the Dutchess Rail Trail, shopping, restaurants, Marist College, Vassar College, and the Culinary Institute of America. Commuters will appreciate quick access to both the Taconic State Parkway and Metro-North, putting convenience within easy reach. Some homes simply check the boxes—this one makes you feel right at home. Between the expansive space and top-tier upgrades, opportunities like this don't last long. Schedule your private tour today!

15 Rock Cut Lane, Pleasant Valley

$1,495,000

3 Beds ⋅ 3 Baths ⋅ 1029871 MLS

Rare and extraordinary custom built private estate nestled on 43 private acres in the heart of Pleasant Valley. Surrounded by rolling woodlands and breathtaking natural beauty, this exceptional residence offers an unparalleled blend of timeless elegance, refined craftsmanship, and resort-style living. Whether you're seeking a luxurious full-time residence, an executive retreat, or a secluded country escape just a short drive from New York City, this remarkable property delivers an unmatched lifestyle. A grand two-story foyer with dual staircases sets the tone for the home's sophisticated interior. Rich architectural details, including tray ceilings, exquisite custom moldings, recessed lighting, and thoughtfully designed built-in cabinetry, create an atmosphere of understated luxury. The inviting living room is anchored by a stunning wood-burning fireplace, offering the perfect gathering space throughout the seasons, while an elegant wet bar complete with its own Sub-Zero refrigerator makes entertaining effortless. Designed for the discerning chef, the gourmet kitchen showcases custom Wood-Mode Cabinetry, Corian countertops, a generous center island with cooktop, premium Sub-Zero refrigerator and freezer, and double GE wall ovens. Every detail has been thoughtfully considered, from the central vacuum system and central air conditioning to the security alarm system and generator hookup, ensuring both comfort and peace of mind. The luxurious primary suite serves as a private sanctuary, highlighted by a spa-inspired bath featuring a Jacuzzi soaking tub, an oversized tiled walk-in shower, dual vanities, and an atmosphere designed for complete relaxation. Step outside to your own private resort. Expansive Bufftech composite decking and railings overlooks an elegant kidney-shaped in-ground pool surrounded by beautifully crafted stamped concrete patio and enclosed by a black metal fence. The pool house, complete with a sink and toilet, provides exceptional convenience for outdoor entertaining. Professionally designed landscaping showcases graceful Japanese maples, vibrant hydrangeas, ornamental grasses, an automatic irrigation system, and impressive Redi-Rock concrete retaining walls, creating a setting that is both breathtaking and effortlessly maintained. For automobile enthusiasts, collectors, entrepreneurs, or hobbyists, the property offers exceptional versatility with an attached two-car garage featuring high ceilings, along with an impressive 40' x 30' detached four-car garage providing abundant space for vehicles, equipment, or a workshop. What truly distinguishes this estate is the land itself. Spanning 43 private acres, the property offers approximately four miles of private motocross and recreational trails, winding through the picturesque landscape and providing endless opportunities for riding, hiking, ATV adventures, or simply immersing yourself in the serenity of nature. It is a rare opportunity to own an estate where luxury living and outdoor recreation exist in perfect harmony. Constructed with premium materials, including durable CertainTeed siding, and enhanced with exceptional craftsmanship throughout, this one-of-a-kind estate represents the pinnacle of Hudson Valley living. Ideally situated just minutes from the Taconic State Parkway, shopping, dining, schools, and the region's celebrated wineries, hiking trails, and cultural attractions, the home also offers convenient access to Metro-North rail service and the New York City metropolitan area. Elegant, private, and truly unforgettable, 49 Barkit Kennel Road is more than a home—it's a destination, a lifestyle, and a legacy property unlike anything else on the market.

49 Barkit Kennel Road, Pleasant Valley

$699,000

4 Beds ⋅ 3 Baths ⋅ 1027869 MLS

Roof is brand new. Perfectly positioned just two miles from the Taconic State Parkway, this exceptional home offers an easy commute north or south while being only five minutes from Overlook Elementary School and nine minutes from Arlington High School. Designed with both comfort and functionality in mind, the home features hardwood floors and elegant crown molding throughout, hydro-air heating and central air conditioning with HEPA filtration, and extensive Ethernet, coaxial, and in-ceiling speaker wiring in every bedroom, the gathering room, and the finished lower level. A double-wide driveway provides abundant parking and a spacious basketball area. Step inside to discover an inviting open floor plan with soaring 9-foot ceilings throughout the living room, dining room, family room, and kitchen. The welcoming living room is anchored by a wood-burning fireplace, while the beautifully appointed kitchen showcases custom cherry cabinetry, stainless steel appliances, and a generous granite center island that naturally becomes the heart of the home. Just off the kitchen, the tiled mudroom/laundry room and powder room offer everyday convenience. The adjoining breezeway connects the attached two-car garage to the home, providing additional storage and easy access. The gathering room is filled with natural light thanks to two Andersen wood French doors with transom windows and expansive cottage-style windows overlooking the peaceful backyard, distant woods, and raised organic garden beds, creating a seamless connection between indoor and outdoor living. The tranquil primary suite serves as a private retreat, featuring a tray ceiling, five oversized windows, in-ceiling speakers, a spacious en-suite bath, and an adjoining study—ideal for a home office, reading room, or quiet sitting area. The finished lower level offers exceptional versatility with high-quality Berber carpeting, generous closet storage, two large casement windows with custom window treatments, and wiring for a surround sound system. Currently configured as a home gym, table tennis area, and media room, this flexible space can easily accommodate a variety of lifestyles. A secondary staircase provides direct access to the garage, allowing convenient entry for service personnel without passing through the main living areas. The adjoining mechanical room also serves as a bright, impeccably maintained workshop complete with commercial-grade tile flooring and abundant storage. Outdoor living truly shines with a covered rear porch featuring skylights that open to a spectacular screened porch designed for effortless entertaining. Beautiful beadboard ceilings, custom trim work, porcelain tile and bluestone flooring, a striking colonial-style chandelier, and concealed cove lighting create an unforgettable space for dining, relaxing, and enjoying the surrounding landscape. Additional features include a Gentran transfer switch conveniently installed beside the main electrical panel, allowing for a safe and simple generator connection during power outages. Combining timeless craftsmanship, thoughtful upgrades, modern infrastructure, and exceptional indoor-outdoor living, this meticulously maintained home offers the perfect balance of elegance, comfort, and convenience.

100 Rockledge Drive, Pleasant Valley

$675,000

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

$250,000

3 Beds ⋅ 2 Baths ⋅ 1020025 MLS

WELCOME HOME TO 30 SMITH! Bring your vision to this spacious 3-bedroom, 1.5-bath Cape Cod offering over 1,300 square feet in the desirable Arlington School District. Ideally located in the heart of Pleasant Valley, this home combines privacy with convenience, just minutes from schools, shopping, parks, restaurants, and commuter routes. Full of timeless character, it features hardwood floors, a wood-burning brick fireplace, an expansive living and dining area, generously sized bedrooms, and a functional floor plan ready for your personal touch. Set on a beautiful, level lot with mature trees, the property offers a spacious backyard and large rear deck perfect for relaxing or entertaining. While in need of renovation, this home's solid bones, desirable location, generous yard, and endless potential make it a rare opportunity to restore its original charm and build instant equity. Sold AS IS. Cash or rehab loans preferred.

30 Smith Road, Pleasant Valley

$799,000

4 Beds ⋅ 3 Baths ⋅ 1024869 MLS

Welcome home to this beautifully maintained expanded Colonial, perfectly situated on 3.42 picturesque acres in the Town of LaGrange within the highly desirable Arlington Central School District. Lovingly cared for by the same owners for over 30 years, this exceptional property offers the perfect blend of timeless charm, generous living space, and outstanding outdoor amenities. Step inside to discover custom trim work, beautiful hardwood floors, and spacious rooms designed for comfortable everyday living and effortless entertaining. The inviting three-season room serves as a wonderful extension of the home—an ideal place to enjoy your morning coffee, relax with a good book, or take in the changing seasons. The oversized family room is anchored by a stunning stone fireplace, creating a warm and welcoming gathering space. A spacious living room provides ample room for holiday celebrations and family gatherings, while the formal dining room is perfect for hosting memorable dinners. Offering four generously sized bedrooms plus a dedicated home office, this home provides the flexibility today’s buyers are looking for. The lower level offers abundant storage, ensuring plenty of space to keep everything organized. Outside, you’ll fall in love with the beautifully landscaped grounds featuring mature trees, colorful gardens, and expansive open space. Enjoy endless summer days in the sparkling crystal-blue in-ground pool. A lawn irrigation system keeps the property lush and green throughout the season, while an invisible pet fence allows your four-legged family members to safely enjoy the yard. A large barn with electricity offers endless possibilities as a workshop, hobby space, vehicle storage, or additional storage. This remarkable property offers the tranquility of country living while remaining just minutes from shopping, restaurants, parks, schools, and major commuter routes. A rare opportunity to own a lovingly maintained home on over three beautiful acres in one of LaGrange’s most sought-after locations.

60 Traver Road, Pleasant Valley

$699,999

4 Beds ⋅ 3 Baths ⋅ 1021840 MLS

STOP THE SEARCH! THIS IS THE ONE! INCREDIBLE PROPERTY! ENTERTAINER'S DREAM HOME! Welcome to your own private Hudson Valley retreat, where every day feels like a vacation. Tucked away at the end of a long private driveway and nestled on just over six beautifully wooded acres in the highly sought after Arlington School District, this exceptional Colonial offers the perfect balance of privacy, comfort, and tranquility. A brand new custom paver walkway welcomes you to the inviting entry foyer, setting the tone for the quality and care found throughout. The heart of the home is the beautifully updated eat in kitchen that has views of your gorgeous back yard oasis, featuring granite countertops, custom tile backsplash, stainless steel Kitchen Aid appliances which include a counter depth refrigerator and a dual function microwave/convection oven, abundant cabinetry, and generous workspace, all opening effortlessly to the formal dining room, making entertaining a breeze. The main level also offers a spacious living room and an inviting family room centered around a cozy wood burning fireplace, creating warm and comfortable gathering spaces for every season. We also have a half bath and laundry conveniently on the main level. Upstairs, you'll find four generously sized bedrooms, including a spacious primary suite complete with dual walk in closets and a large private en suite bath. The additional bedrooms offer abundant closet space and are served by a thoughtfully designed hall bath featuring a separate powder room area, making busy mornings easy for everyone. Step outside and prepare to fall in love. The backyard is nothing short of spectacular, offering the ultimate private escape. An expansive deck overlooks the resort style setting below, where a sparkling in ground pool, multiple tiered patios, beautifully landscaped grounds, and countless spaces for relaxing or entertaining create an atmosphere that rivals a luxury vacation destination. Whether you're enjoying your morning coffee, hosting unforgettable summer gatherings, tending to the garden, or unwinding around the fire pit beneath the stars, this remarkable property offers an unmatched lifestyle surrounded by complete privacy and mature woodlands. Additional highlights include an oversized two car garage with brand new garage doors, as well as a rare lower level garage tucked in the expansive unfinished basement, offering exceptional storage or the perfect space for a workshop, hobbies, or recreational equipment. The home also features forced hot air, central air conditioning, well maintained mechanical systems, and a long private driveway with a circular turnaround that provides both everyday convenience and an elegant sense of arrival.Ideally located just minutes from award winning restaurants, wineries, breweries, shopping, hiking, parks, farmers markets, and all that the Hudson Valley has to offer, while remaining commuter friendly ( just 7 minutes to the Taconic State Parkway) , this is truly the total package. Homes offering this level of privacy, outdoor living, and turnkey condition are exceptionally rare. Schedule your private showing today and experience everything this extraordinary property has to offer.

185 Rombout Road, Pleasant Valley

$519,000

3 Beds ⋅ 3 Baths ⋅ 1022851 MLS

Welcome home to this well-maintained 3-bedroom, 2.5-bath property offering comfort, efficiency, and versatile living space. The partially finished basement features brand-new flooring, providing additional room for a home office, recreation area, fitness space, or hobby room. The kitchen is equipped with new appliances, while owned solar panels help improve energy efficiency and reduce utility costs. Enjoy relaxing or entertaining on the covered, screened patio overlooking the backyard. Additional highlights include a spacious two-car garage and a location that's approximately a 10-minute drive to Eastdale, offering convenient access to shopping, dining, and everyday amenities. This home combines thoughtful updates with practical features, making it ready for its next owner.

70 Gretna Hill Road, Pleasant Valley

$800,000

4 Beds ⋅ 3 Baths ⋅ 1014436 MLS

Welcome to this lovely Hudson Valley estate where timeless architecture and exceptional privacy come together on 13.7 breathtaking park-like acres in the heart of LaGrange, just minutes from the Village of Millbrook. A picturesque quarter-mile, partially pine-lined driveway creates a country approach, setting the stage for this remarkable property. Perfectly positioned with a coveted southwest-facing orientation, the home is bathed in natural light throughout the day while showcasing spectacular sunset views over the surrounding landscape. This beautifully maintained 4-bedroom, 2.5-bath home offers an effortless blend of elegance, warmth, and everyday comfort. The inviting living room features a dramatic stone wood-burning stove and sliding glass doors that seamlessly connect the interior to the expansive outdoor living spaces. A stunning circular sunroom wrapped in windows provides a peaceful retreat to enjoy panoramic views of the property's natural beauty in every season. The thoughtfully designed floor plan also includes a private home office with separate entrance and spacious dining room ideal for both casual living and entertaining. The luxurious primary suite is a private sanctuary, complete with soaring cathedral ceilings, skylights, a floor-to-ceiling stone fireplace, private balcony, and an en-suite bath. Three generously sized guest bedrooms and full bathroom complete the second level, offering comfort and flexibility. Perfect for entertaining. The grounds are truly exceptional, creating a private country club setting designed for recreation and relaxation. Enjoy summers around the heated saltwater in-ground pool with pool house, challenge friends on the full-sized tennis and basketball sports court, or gather around the custom stone firepit beneath the stars. Mature specimen trees, including a magnificent Japanese maple, lush lawns, and thoughtfully landscaped grounds create an atmosphere of serenity rarely found. A two-car attached garage is complemented by an oversized detached garage with utilities, offering endless possibilities for a workshop, collector vehicles, hobbies, or additional storage. Wonderfully maintained with extensive capital improvements, the home offers exceptional peace of mind with a newer roof, septic system, Andersen windows and doors, updated HVAC systems (2 condensers and 2 air handlers), whole-house generator, spray foam insulation, well pump and pressure tank, water treatment system with UV filtration, CO2 neutralizer and softener, skylights, California Closets, smart thermostats, updated flooring, and numerous exterior enhancements. A complete improvement list is available. Ideally located just minutes to the Taconic State Parkway, Metro-North, and the shops, restaurants, wineries, and equestrian estates that define the Hudson Valley lifestyle, this turnkey estate presents a rare opportunity to own an exceptional private retreat where luxury, recreation, and nature exist in perfect harmony.

32 Cole Road, Pleasant Valley

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