Pleasant Valley Real Estate

Pleasant Valley: A Charming Town in Dutchess County, NY

Nestled in the heart of Dutchess County, New York, lies the picturesque town of Pleasant Valley. With its idyllic landscapes, friendly community, and convenient location, this charming town has become a sought-after destination for both residents and visitors alike.

Pleasant Valley offers the perfect blend of small-town charm and modern amenities. Its quaint downtown area is lined with local shops, boutiques, and cozy cafes, creating a warm and inviting atmosphere. Residents can enjoy a leisurely stroll through the town, exploring the unique boutiques or grabbing a bite to eat at one of the many charming restaurants.

Nature enthusiasts will find themselves in paradise in Pleasant Valley. Surrounded by rolling hills, lush forests, and beautiful lakes, outdoor activities abound. Residents can take advantage of the numerous hiking and biking trails, go fishing in one of the nearby lakes, or simply relax and enjoy the serene beauty of the area.

Conveniently located in Dutchess County, Pleasant Valley offers easy access to major cities such as Poughkeepsie and New York City. Commuters will appreciate the proximity to major highways and public transportation options, making it an ideal place to call home for those who work in the city but prefer a quieter lifestyle.

With its rich history, natural beauty, and welcoming community, Pleasant Valley truly has something for everyone. Whether you're looking to settle down, raise a family, or simply enjoy a peaceful retreat, this charming town in Dutchess County, NY, is the perfect place to make your dreams a reality.

Newest Listings in Pleasant Valley

$899,900

5 Beds ⋅ 4 Baths ⋅ 1049263 MLS

Opportunities like this are exceptionally rare. Nestled on more than two peaceful acres along the picturesque Wappingers Creek, this one-of-a-kind property offers two beautifully finished homes on a single parcel—creating endless possibilities for multigenerational living, rental income, guest accommodations, or an owner-occupied investment. The primary residence has been thoughtfully remodeled throughout and features 4 spacious bedrooms, 2.5 bathrooms, and a bright, welcoming floor plan designed for comfortable everyday living. A large basement provides abundant storage or the opportunity to create additional finished living space. The second home is a stunning newly constructed residence that blends modern design with exceptional efficiency. Soaring vaulted ceilings and an open-concept layout create an airy, expansive feel, while the highly energy-efficient ductless HVAC system offers year-round comfort. The home also features an office/den, laundry room, loft space accessed by a charming ladder, and a striking freestanding fireplace that serves as the centerpiece of the living area. Step outside to a fenced backyard—perfect for pets, entertaining, or simply enjoying your own private outdoor retreat. The grounds are equally impressive. Set on over two acres bordering the tranquil Wappingers Creek, the property offers a peaceful natural setting with mature landscaping, a large garden ready for your green thumb, and a detached garage providing additional storage, workshop space, or parking. Whether you're looking to offset your mortgage with rental income, create the perfect setup for extended family, establish a private guest house, or capitalize on short-term rental potential (subject to local regulations), this versatile property offers flexibility that is increasingly difficult to find. All of this is conveniently located within the highly regarded Arlington Central School District while providing the privacy and serenity of country living. A truly unique offering that combines modern amenities, income potential, and an exceptional setting into one remarkable property.

13-14 Creekside Place, Pleasant Valley

$599,000

4 Beds ⋅ 3 Baths ⋅ 1048916 MLS

Rare opportunity to secure two single family homes on the same property. Main house is a 3 bedroom, 1.5 bath cape cod, which has been tastefully updated and is loaded with attractive finishes. Remodeled kitchen with quartz counters & stainless appliances flows seamlessly to living room/dining room combo. Huge sunroom with adjacent bluestone patio for outdoor living enjoyment. First floor bedroom and full bathroom. Second level includes two additional bedrooms plus office/den and half bathroom. Updated bathroom, new vinyl flooring & fresh paint throughout. Recent improvements include roof, windows, siding, gutters, deck, water softener, water heater, well pump & a/c condenser. One bedroom cottage includes kitchen, bathroom, living room, den/office and laundry room. Huge screened porch leads to expansive park-like property, which is fully fenced w/mature landscaping, fire pit area & pool with new liner & filter. Enjoy the convenience of natural gas for heat & hot water. An impeccably maintained offering creating an ideal configuration for extended family living or income potential. Centrally located with easy access to Eastdale Village, Pleasant Valley, Millbrook, Poughkeepsie train station and Taconic State Parkway. Don't miss your chance for this truly unique offering.

13-17 Clark Heights, Pleasant Valley

$289,000

3 Beds ⋅ 2 Baths ⋅ 1049009 MLS

Brand-New 2026 Living in Pleasant Valley. Welcome to 9 Odell Lane, a brand-new 2026 model offering modern finishes, generous living space, and effortless low-maintenance living. The bright, open-concept interior features a spacious kitchen with center island, contemporary cabinetry, recessed lighting, new appliances, and a clean, neutral design throughout. Outside, enjoy a generous yard framed by mature trees, providing plenty of space to relax, entertain, garden, or simply enjoy the outdoors. A spacious rear deck extends your living space outside, while the detached garage offers valuable additional parking, storage, or workspace. Located in a well-maintained community, the $838/month lot fee includes snow removal, garbage pickup, water & taxes, all while keeping you minutes from Pleasant Valley, Millbrook & LaGrange. New construction, modern comfort, and outdoor space—all without the maintenance of a traditional property. Schedule your private tour of 9 Odell Lane today!

9 Odell, Pleasant Valley

$549,900

3 Beds ⋅ 2 Baths ⋅ 1047918 MLS

Space, style, and versatility come together at 15 Rock Cut Lane. Thoughtfully arranged across three finished levels, this 3-bedroom, 2-bath home offers a flexible floor plan with plenty of room to live, work, gather, and unwind. Inside, soaring ceilings and abundant natural light create an open, airy feel throughout the main living space. The open-concept layout brings the living room, dining area, and kitchen together, with a propane fireplace adding warmth and character. The kitchen features striking red cabinetry, quartz countertops, stainless steel appliances, and plenty of space for everyday meals or entertaining. A dedicated office/flex space on the first floor provides a convenient and versatile area for working from home, hobbies, a playroom, or additional guest space. One of the home's standout features is the expansive primary suite. Generously sized and designed as a private retreat, it includes a large walk-in closet and an impressive ensuite bath with dual vanities, a soaking tub, and oversized glass-enclosed shower. Finished space on multiple levels provides plenty of flexibility for a home office, recreation room, fitness area, guest accommodations, or whatever best suits your lifestyle. Extensively renovated in 2022, the property received major improvements including the roof, siding, windows, foundation, electrical, plumbing, heating, and septic, allowing you to enjoy an updated home without taking on a lengthy renovation list. Located in the Arlington School District* the home offers convenient access to Eastdale Village, shopping and dining, the Dutchess Rail Trail, Walkway Over the Hudson, Marist College, Vassar College, the Culinary Institute of America, Metro-North, and the Taconic State Parkway. With generous room sizes, extensive updates, and a flexible floor plan, 15 Rock Cut Lane offers the space to make this home truly your own.

15 Rock Cut Lane, Pleasant Valley

$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

$304,900

3 Beds ⋅ 1 Baths ⋅ 1045430 MLS

Welcome to 37 Shady Creek Road, a beautifully renovated ranch nestled in the sought-after Shady Creek community. Blending modern upgrades with cozy character, this turnkey home offers comfortable single-level living in a peaceful setting. Inside you'll find an inviting open layout featuring three bedrooms, stylish new flooring, fresh paint, and abundant natural light. The thoughtfully updated kitchen showcases quartz countertops, subway tile accents, sleek cabinetry, and stainless-steel appliances. Recent improvements including a new roof, gutters, and energy-efficient spray foam insulation. Outside, enjoy quiet mornings in the three-season porch or entertain guests on the charming brick patio overlooking the yard. Conveniently located just minutes from Eastdale Village, shopping, restaurants, and commuter routes, this home offers the perfect balance of privacy and accessibility. Nearby Wappingers Creek provides opportunities for kayaking, fishing, and enjoying the natural beauty of the Hudson Valley. An ideal choice for first-time buyers, downsizers, or anyone seeking a move-in ready home with style, efficiency, and value.

37 Shady Creek Road, Pleasant Valley

$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

$449,900

3 Beds ⋅ 2 Baths ⋅ 1043346 MLS

PEACEFUL AND PRIVATE newly renovated 3BR home in the Town of Pleasant Valley. Brand new kitchen with granite counters and new stainless appliances. Bright, spacious sunroom overlooking the peaceful yard and woods in the rear of the property. Large, open living/dining room and an additional family room. Beautifully refinished original hardwood floors and fresh paint throughout. Large 2nd floor bedrooms with spacious closets (and one cedar closet). Huge 2-car attached garage that has an expansive area above with great possibilities. Full basement with brand new boiler and hot water heater. Large land parcel with spacious shed/barn offering plenty of additional storage. A bucolic feel but close to everything – three minutes from the downtown area of Pleasant Valley and easily accessible to both Poughkeepsie and the Taconic Parkway. Located in the Arlington Central school district. Nothing to do but move in!

1078 Salt Point Turnpike, 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

$649,000

3 Beds ⋅ 3 Baths ⋅ 1045407 MLS

Welcome to 71 O’Halloran Circle, where space, privacy, and possibility come together on 3.74 scenic acres in Pleasant Valley. This inviting raised ranch offers 4 bedrooms, 2 and a half bathrooms, and a versatile layout designed for comfortable everyday living and effortless entertaining. Inside, generous living spaces provide plenty of room to gather, unwind, work from home, or create the lifestyle you have been envisioning. The home’s flexible design allows each level to serve a distinct purpose while still feeling connected and functional. Outside, the expansive property offers a rare sense of peace and seclusion, with endless potential for outdoor entertaining, gardening, recreation, or simply enjoying the natural surroundings. A two-car garage provides additional convenience, storage, and workspace. Whether you are searching for room to grow, space to entertain, or a private Hudson Valley retreat to make your own, 71 O’Halloran Circle delivers the land, layout, and opportunity to bring that vision to life.

71 O'Halloran Circle, 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

$339,000

2 Beds ⋅ 2 Baths ⋅ 1038481 MLS

This charming 1920s home combines character with comfortable one-level living in a highly walkable location. The inviting interior features two bedrooms, a home office, an efficient kitchen, a welcoming living room, a sun-filled dining room, one-and-a-half baths, and a mudroom with laundry. While the second floor creates flexibility for additional living space, the full basement provides generous storage. Enjoy outdoor living on the rear deck, in the thoughtfully landscaped yard, or from the front porch. The oversized two-car garage affords ample space for parking, storage, or hobbies. Conveniently located just moments from Pleasant Valley’s Main Street, this home offers easy access to the grocery store, restaurants, and shops. For the commuter, the location is easily accessible to Route 44, the Taconic Parkway, and about a 15 minute drive to Poughkeepsie Metro North/Amtrak train station.

33 North Avenue, Pleasant Valley

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Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.