Charm, Space & Incredible Value in the Heart of the Village! Don’t miss your chance to own a fully renovated, move-in ready home with historic character, modern upgrades, and exceptional value — all in one of Pleasant Valley’s most desirable and accessible locations.
This spacious 3–4 bedroom, 2-bath Arts & Crafts-style home sits on a quiet stretch of Main Street and offers more than 2,000 square feet of finished living space, plus a large basement and shed for extra storage. Whether you’re a first-time buyer, growing household, or multigenerational family, this property delivers flexibility, comfort, and long-term potential—at a fraction of the price you’d expect for this kind of quality.

Inside, enjoy:
* A 3 year old roof, upgraded 200-amp electrical, and energy-efficient vinyl windows
* Central air conditioning and refinished 100+ year-old hardwoods (Maple & Douglas Fir)
* A fully updated kitchen with stainless steel appliances
* Two renovated full bathrooms—one on each floor
* A main-floor bonus room/den, perfect for guests, an office, or even a first-floor bedroom
* A large three-season sunroom that brings the outside in

The layout is ideal for mother/daughter living or anyone needing separate spaces for work or relaxation. Upstairs, you’ll find three oversized bedrooms with walk-in closets and a sleek full bath. Downstairs, the flow between the living room, dining room, kitchen, and sunroom makes entertaining effortless. Outside, the .20-acre lot is low-maintenance yet private, featuring a long driveway, parking pad, and a 5-year-old shed that’s perfect for tools, toys, or creative projects. 

Best of all? You’re just minutes from the Taconic Parkway, 15 minutes from Metro-North, and moments from shops, schools, parks, and everything Eastdale and the Village have to offer. With low taxes, modern amenities, and timeless appeal, this is one of the best values on the market in Dutchess County.

Nestled on over 3.2 serene acres, this beautifully renovated log home combines rustic charm with modern luxury. Offering 3 spacious bedrooms, 2.5 bathrooms, and 2,561 sq ft of thoughtfully designed living space this home has room to relax, entertain, and grow.

Step inside to discover a bright and inviting open floor plan, highlighted by a stunning chef’s kitchen featuring top-of-the-line stainless steel appliances, custom cabinetry, and elegant finishes. The main living area blends warmth and functionality with natural wood accents and an effortless flow between kitchen, dining, and lounge spaces.

Whether you're entertaining guests or enjoying a peaceful evening at home, the blend of rustic textures and contemporary updates creates a one-of-a-kind atmosphere. The finished basement offers even more space for a home office, gym, media room, or kids play room.  The possibilities are endless!

Surrounded by nature, yet perfectly updated for modern living, this home is a rare gem. Don’t miss your chance to own a slice of peaceful luxury.

Welcome to 6 Swain Drive, a charming Cape Cod-style home nestled in the heart of Pleasant Valley, NY. This delightful residence offers 3 bedrooms and 1.5 bathrooms across 1,680 square feet of comfortable living space
As you step inside, you're greeted by a sunlit living room featuring a beautiful bay window that bathes the space in natural light. Adjacent to the living room is a cozy family room, complete with a wood-burning fireplace—perfect for gatherings on cooler evenings. The formal dining room provides an elegant setting for meals, while the spacious kitchen offers ample room for a breakfast nook, making it ideal for casual dining.  
The home's exterior is equally inviting, boasting a picturesque yard adorned with mature landscaping. An expansive wraparound porch provides a serene spot to relax and enjoy the surrounding beauty. Situated on a generous 0.68-acre lot, this property offers both privacy and space
Additional features include central air conditioning, ensuring year-round comfort, and an attached one-car garage for convenient parking. Located within the Arlington School District, this home is also in close proximity to Metro North Trains, the Taconic State Parkway, County Route 9, the Mid-Hudson Bridge, and I-84. Nearby amenities encompass hospitals, shopping centers, malls, restaurants, colleges, and historic sites, including the renowned Walkway Over the Hudson
Experience the perfect blend of comfort and convenience at 6 Swain Drive—your ideal home awaits.

Nestled in Northern Dutchess, this picturesque Cape Cod offers serene creekside living with waterfall view. The bright and airy kitchen, featuring stylish countertops, a tasteful backsplash, and warm wood floors, opens seamlessly to a sunlit living room. A breezeway, serving as a functional mudroom with a laundry area, leads to a spacious deck overlooking the water.
The first floor includes two inviting bedrooms and a beautifully updated full bath. Upstairs, the private primary suite provides a tranquil retreat with generous space and an elegantly updated ensuite bath. Gleaming hardwood floors flow throughout the home, adding to its timeless appeal.
Ideally located in the heart of the Hudson Valley, this home is just minutes from the charming village of Millbrook, the Taconic State Parkway, excellent restaurants, and endless outdoor activities.

Looking for an affordable home that just needs some updating? Well look no further. This 2 Bedroom 1 Bath Mobile home in Hickory Hill Estates set just outside of the village of Plesant Valley is perfect for you. Come see the park like setting in Hickory Hill and make this your home.

Stunning and complete renovation in the heart of Salt Point, minutes to Taconic. Like new construction without the wait in this Old Style Barn brought to modern day Farmhouse. A covered rocking chair blue stone front porch walks you into the home featuring rustic wood flooring throughout, first floor bedroom, office, full bath with custom tile surround shower, recessed lighting, custom kitchen with granite countertops, farm sink and SS appliances. Upstairs you will find a second well sized en suite with walk-in closet, full laundry room and the breathtaking primary en suite which features beamed ceilings, beautiful oversized windows allowing ample natural light, his and hers walk-in closets, sitting area and en suite bath completed with heated floors, a claw foot soaker tub, custom tiled shower and double vanity with granite tops. Full unfinished basement with walk-out for future bonus room/flex space expansion and ample added storage space. Exterior features 2 acres of privacy, blue stone path, mature landscaping, charming cupola, vinyl board and batten siding, newly paved driveway and 250 SQ FT Trex deck overlooking your own private pond and fountain. Brand new plumbing, 200 amp electric, high efficiency dual zoned Bosch forced air heat pumps, spray foam insulation and Anderson windows to add to the list! Excellent location, a perfect weekend get-a-way or full time residence. Minutes to the Villages of Pleasant Valley, Millbrook & Rhinebeck, shopping, schools, culinary grade restaurants and more!

Discover the Potential at 1675 Main Street, Pleasant Valley!

This spacious home is full of charm and possibility, just waiting for your personal touch. Whether you're looking to create a cozy family retreat or explore the option of a mother-daughter setup, there's plenty of room to make it your own.

The property extends all the way back to a serene creek, offering a peaceful, private setting perfect for gatherings or quiet moments by the fire pit. It truly feels like your own little oasis, yet you're just a short walk from the heart of the Pleasant Valley hamlet with its local shops, cafes, and community feel.

With easy access to the Taconic Parkway and just minutes to the Poughkeepsie train station, commuting is a breeze. Don’t miss this opportunity to bring your vision to life in an ideal location with so much to offer!

Back Yard, Private, See Remarks, Waterfront

Step into this beautifully updated first-floor apartment, offering simple, comfortable living in the heart of Pleasant Valley. Featuring one spacious bedroom and a fully renovated bathroom, this charming unit is perfect for anyone seeking a low-maintenance lifestyle.

Enjoy the ease of plenty of parking right on the property and the convenience of a location that’s ideal for commuters—close to major routes, shopping, and local amenities.

Set on a large, beautifully landscaped corner lot, this stylish and fully updated one-level home offers comfort, modern upgrades, and a prime location. With many recent improvements—too many to list!—this home is truly move-in ready.

Step inside to a spacious living room anchored by a wood-burning fireplace, seamlessly flowing into the dining area. The brand-new kitchen is a chef’s dream, featuring quartz countertops, a gas range with a pot filler, custom cabinetry, vaulted ceilings, and radiant heat floors. A dedicated home office provides a quiet space to work, while the bonus family room with a wood-burning stove is perfect for relaxed gatherings.

The primary suite boasts a renovated ensuite bath and a walk-in closet, while two additional bedrooms share an updated bath, offering plenty of space for family or guests. The 2-car garage and basement provide abundant storage. Recent upgrades include a new roof, new windows, central AC, and a new hot water heater.

Outside, enjoy a partially fenced-in, private backyard with lush landscaping and room for a pool, offering endless possibilities for outdoor enjoyment.

Prime location! Just minutes from the Taconic State Parkway, Millbrook, and Rhinebeck, this home is also within walking distance of Fireside Grill, Helen Aldrich Park, Hummingbird Ranch Market, and Frances J. Mark Memorial Park with its scenic swimming pond. Plus, with Little Wappinger Creek right across the street, this home captures the best of Hudson Valley living.

Back Yard, Corner Lot, Front Yard, Level, Near Shops

Welcome to 38 Parksville Road, a charming and thoughtfully designed home in the heart of Pleasant Valley, New York. This residence beautifully combines comfort and style, offering a seamless blend of indoor and outdoor living. Step inside to discover an open walk-through kitchen that effortlessly leads to the dining area. Perfect for both everyday living and entertaining, this layout allows for easy interaction with guests and family. From the dining area, step through the sliding doors to access the back deck, where you can enjoy outdoor dining and relaxation in a serene setting. The cozy living room, complete with a fireplace, provides a warm and inviting space to unwind and create lasting memories. Down the hallway, you'll find all three bedrooms, including a spacious primary bedroom with its own ensuite bathroom for added privacy and convenience. An additional full bathroom serves the other bedrooms on this floor. The finished basement offers a versatile multi-purpose recreation room, ideal for a home office, gym, or playroom. You'll also find a laundry and utility room, along with access to the 2-car garage, providing ample storage and functionality. Situated in a desirable neighborhood, 38 Parksville Road is close to local amenities, schools, and parks, making it a perfect place to call home. Don't miss the opportunity to experience all that this lovely property has to offer. Schedule your showing today!

Back Yard, Front Yard, Hilly, Level, Near School, Near Shops, Paved

This newly constructed gem sits perched at the top of O'Halloran Circle boasting an over 7.8 acre lot, both private and tranquil with so much possibility. This cottage was over engineered at every step and saw meticulous oversight by the owner/builder during the entire process. No expenses were sparred in making this home as solid as possible with an extra 2" of concrete reinforcement used on both the slab and foundation walls. Oversized beams were used in the support for the roof framing as well; all done to ensure decades of worry free ownership. The kitchen boasts custom concrete counters, LED light fixtures both recessed and suspended, and custom Hickory hardwood flooring throughout. The primary bedroom is a full ensuite, featuring a full bath with separate soaking tub, shower, and walk in closet. The other 2 bedrooms are well sized and offer plenty of natural light. The basement is unfinished, but is a full sized walkout with tall 8' ceilings. Could make an excellent office, workout, craft/hobby area, etc. Outside you'll find over 500sqft of covered porch both front and rear making this home a nature lovers dream with many attractive features. The lot size offers the potential for massive self sufficient gardens and/or additional out buildings and amenities. There is currently a fenced-in area that houses rescued goats and previously had housed a chicken coup too. Truly a lovely and extremely well built home, just waiting for your own creative touches and style.

Back Yard, Hilly, Private, Secluded, Wooded

Set amid the rolling hills of Pleasant Valley, The Gallagher offers a harmonious blend of financial opportunity and country tranquility, boasting nearly 200K in annual rental revenue. Designed for gatherings and getaways, this 5-BR, 3.5-BA home unfolds across an open, light-filled layout. The heart of the home is the expansive chef's kitchen - outfitted with dual convection ovens, a gas range and wine fridge, it's designed to handle everything from intimate meals to festive gatherings.Cherry cabinetry provides ample storage, while the granite countertops and large island with prep sink offer abundant workspace. A separate casual dining area is the perfect spot for coffee, bathed in morning light from the large bay window and adjacent to the kitchen is a formal dining room with seating for 10. The massive 1st Fl primary suite is a serene retreat, featuring a gas fireplace, private deck with hot-tub and an ensuite bath with glass shower and dual vanities. Upstairs, two generously sized bedrooms with walk-in closets share a full bath. A cozy loft lounge overlooks the main living area, providing a serene space for reading or working from home. The finished walkout lower level is a haven of entertainment—where movie nights stretch late in the home theater and friendly competition takes center stage in the game room. Outside, the heated saltwater pool and hot tub invite guests to linger a little longer. Sitting on 5.62 private acres, the central location offers access to some of the Hudson Valley's most charming towns and attractions. Rhinebeck, with boutique shopping and farm-to-table restaurants, is just a short drive away. Millbrook, known for its equestrian culture, wineries and rolling countryside, is equally close. For outdoor enthusiasts, Taconic Hereford State Forest and Innisfree Garden provide miles of trails. The Gallagher is an income-generating retreat that balances investment savvy with the soul of a countryside escape, all just 2hr from NYC.

Step inside this stylishly finished and completely renovated spacious and sizable raised ranch style home. You will be greeted by the oversized living room that features a large front window allowing the natural light to flow through, and connects to the dining room with sliding glass doors to a rear deck with a ceiling fan and a modern glass railing overlooking an oval shaped in-ground swimming pool that you can relax in and enjoy this summer - it highlights a NEW liner, NEW surrounding patio and NEW pool fence ( cover on backorder) positioned on 0.74 acre of flat property. The kitchen showcases a stainless steel stove, refrigerator, dishwasher and microwave along with beautiful cabinetry, fixtures and quartz countertops. The main level also features the primary bedroom, two additional bedrooms and a stylish hallway bathroom with ceramic tile flooring. The main living level highlights beautiful refinished hardwood floors. The lower finish level of the home features an extra large family room, a walk-in closet and a full bathroom. An attached two car garage with a side entrance to the property and spacious driveway. The home highlights Central A/C, a NEW Roof and NEW Windows. Located off West rd, just two minutes to the quaint town of Pleasant Valley with its local shopping and restaurants to enjoy. Plus just 5 minutes to the fabulous East Dale Village Town square, a short easy commute to schools, the Taconic Parkway along with Metro North Trains. Come see what Dutchess County has to offer with its many outdoor activities to enjoy

Near Public Transit, Near School, Near Shops

Must see newly renovated second floor apartment, 2 bedrooms and one full bath. Kitchen has a back deck. There is plenty of parking. The property is a prefect spot for commuters.

This 4-bedroom SF house is located minutes away from the Taconic State PKWY. Close to school, major routes, many great restaurants and shops. This house with brand new driveway and new water line for the house. As you step inside, you will see everything is brand new, new flooring, new kitchen and appliances, brand new patio door goes to tranquil backyard. Living room equipped with a wood burning fireplace which you can cozy up during winter with friends and family. 8-foot nice and spacious basement can be used as a storage place or kids play room. Additional Information: HeatingFuel:Oil Above Ground,

Welcome to this stunning estate nestled on 1.7 acres of pristine flat land in the heart of Pleasant Valley. Surrounded by lush trees and captivating panoramic views, this home offers the perfect blend of luxury, tranquility, and modern living.
As you step through the welcoming foyer, you are immediately greeted by an abundance of natural light that flows seamlessly through the open floor plan. The home boasts exquisite chandeliers throughout, enhancing its timeless elegance. The expansive chef's kitchen is a culinary dream, featuring high-end appliances, custom cabinetry, and ample counter space, making it ideal for both everyday living and entertaining. Adjacent to the kitchen is a formal dining room, perfect for hosting intimate dinners, while the formal living room opens into an all-season room that can easily serve as a second office or serene retreat. The spacious family room, complete with soaring ceilings, leads to a grand home office – an inspiring space for remote work or creative projects. The luxurious master suite is a private sanctuary, complete with a large sit-in living area, a spa-like en-suite bathroom with heated floors, dual vanity, and an expansive custom walk-in closet. The additional bedrooms each have attached bathrooms, including a Jack and Jill suite adorned with custom tilework. Step outside to discover the breathtaking outdoor oasis. The backyard is framed by a newly constructed brick wall, perfectly outlining the picturesque inground pool and meticulously landscaped grounds an entertainer’s paradise or peaceful escape. This exceptional property is a rare find, offering both privacy and proximity to local amenities. Experience the beauty and elegance of this Pleasant Valley gem, your dream home awaits.

Serene Oasis Just Minutes from Town – Your Dream Home Awaits! 
    Welcome to your very own slice of paradise! Nestled on a sprawling 2.3 acres, this stunning 3400 sqft + living space is a true retreat, boasting everything you need for a life filled with comfort, charm, and endless adventures. Discover a home imbued with character and bright, airy spaces. The open-concept living area features expansive windows that flood the interiors with natural light, creating an inviting atmosphere that’s perfect for both relaxation and entertaining. Cozy-up with your favorite novel by one of 2 fireplaces on a cold winter's day.
    Retreat to your master suite, where tranquility reigns supreme. Unwind in the oversized jetted tub, offering a spa-like experience right in your own home. The additional bedrooms provide ample space for family or guests, ensuring everyone feels at home. The expansive semi-finished basement has room for so many forms of entertainment- games, theater, hobby and craft shops. Be creative. Step outside and be greeted by your very own private oasis! Take a dip in the sparkling swimming pool, surrounded by a beautifully designed deck perfect for sunbathing or hosting summer soires.
    All your conveniences are a short walk away. Grocery, transportation, pharmacy, a wide variety of restaurants, a library, parks and the post office, to name some of many. 
see below to view an aerial map of the community: 

https://www.google.com/maps/@41.7378516,-73.8277743,898a,35y,19.08h,44.69t/data=!3m1!1e3?entry=ttu&g_ep=EgoyMDI1MDMwNC4wIKXMDSoASAFQAw%3D%3D

Back Yard, Cleared, Front Yard, Garden, Landscaped, Level, Private, Views, Waterfront

Welcome to your new home in Hickory Hills! This charming mobile home residence offers 3 bedrooms, and 2 full bathrooms. There is a Dining room right off the kitchen—currently used as a fourth bedroom but can easily be converted back into a dining area. With just over 1,000 square feet of living space, the home has an open-concept layout where the kitchen seamlessly flows into the living area. A unique counter with barstool seating that overlooks the stove is a lovely personal touch added and updated by the current owner but could easily be changed to fit your style. Featuring a one-of-a-kind, handcrafted front door custom-designed by the owner.

The primary bedroom features a private ensuite bathroom, while the two additional bedrooms share a nice-sized guest bath with walk-in shower. Outside, a large, level lot hosts a spacious deck overlooking a generously sized backyard—ideal for summer BBQs, setting up a fire pit, or simply enjoying the outdoors. Located close to Eastdale Village and an array of shopping and dining options, this property is perfectly situated for convenient living. Plus, enjoy the added benefit of NO Taxes!

Don't miss the opportunity to make this home your own. Schedule your viewing today!

Charming Colonial Home on Over 3 Acres. Nestled on a serene cul-de-sac, this beautiful Colonial-style home offers the perfect blend of comfort and modern updates. Boasting 3 spacious bedrooms and 2.5 bathrooms, including a primary suite with its own private bath, this home is designed for both relaxation and functionality. The kitchen has been tastefully renovated, making it a dream for home chefs, and the newer roof, water heater, well tank and furnace provide peace of mind. Stay cozy by the wood-burning fireplace, or enjoy the outdoors from your expansive wrap-around porch overlooking your private, wooded lot. Energy efficiency is a plus with installed solar panels, keeping your utility costs low. Situated less than 2 miles from the Taconic State Parkway, this home is ideal for commuters seeking tranquility without sacrificing convenience. This is your opportunity to own a picturesque property in a peaceful setting – come see it today!

Back Yard, Cul-De-Sac, Part Wooded, Private, Waterfront

Welcome to this stunning contemporary masterpiece, featuring a resort-style indoor pool and exquisitely designed spaces to suit every lifestyle. Offering over 6,000 square feet of beautifully finished living space, designed for those who appreciate modern style, open spaces, and effortless entertaining. Set on a private, tranquil property, yet just minutes from the vibrant Eastdale Village, this home perfectly balances seclusion with convenience, all less than 1.5 hours from Manhattan. Thoughtfully renovated from top to bottom, every inch of this home reflects refined design and quality craftsmanship. Upon entering, you’re welcomed by the tastefully designed foyer and sun-drenched interiors, with an open-concept living room anchored by a sleek gas fireplace. The seamless connection to the outdoor space floods the room with natural light. The spacious chef’s kitchen is equally impressive, featuring stainless steel appliances, custom finishes, and ample workspace, making it the heart of the home for both casual mornings and lively gatherings. The primary suite is a retreat unto itself, offering a luxurious en suite bathroom, a private sunroom, and an outdoor porch—the perfect place to begin or end your day. The home’s additional tastefully renovated bathrooms continue the theme of modern elegance, ensuring both style and comfort throughout. At the center of this home’s lifestyle experience is its indoor pool, complete with a hot tub and custom bar, transforming everyday living into a resort-inspired escape—whether entertaining guests or enjoying quiet relaxation. A wraparound porch invites you to unwind outdoors and take in the serenity of the property’s natural setting. With central air conditioning, a two-car garage, and ample privacy, this home offers a turn-key modern living experience. Yet, it is ideally located just under five miles from Eastdale Village’s dining and shops, and moments from the Taconic State Parkway, Poughkeepsie Metro-North, and the charming towns of Millbrook and Rhinebeck. Combining sleek contemporary design with the ease of Hudson Valley living, this one-of-a-kind home is ready to welcome you—schedule your private viewing today.

Located in the heart of the Village of Pleasant Valley - Close proximity to all area Amenities and Commuting Routes - Living Room with Hardwood Floors and Stone Fireplace - Spacious Eat-In Kitchen - First Floor Bedroom and two additional Bedrooms on second floor - Enclosed Front Porch - Detached Garage - Walk up Attic for extra Storage

Contemporary 1 bedroom 1 full bath rental in the picturesque area if Pleasant Valley, NY.  The kitchen is modern and newer.  The living room and dining room areas are spacious. There a balcony to enjoy the nicer weather.  The complex sits on beautiful grounds for you to use.  Plenty of parking and located close to Poughkeepsie Train Station and the Taconic Parkway for easy commuting.  The apartment is equipped with a washer and dryer for your convenience.  Landlord pays for water/sewer, trash removal, lawn and snow care.  Utilities not included. Pets allowed with approval.  Please no large aggressive breeds. This is in the B building.

Nestled on 1.3 acres this beautiful custom built home captures your attention immediately. A southern design home with its European roof Dutch gable architecture is exquisite. Upon the entrance is a gorgeous two-story with open loft & sunlight throughout the entire 1st floor. The open floorplan with fireplace is a perfect blend of rustic comfort & chic country. Designed with an open kitchen with stainless steel appliances and granite countertops you'll just love cooking & entertaining in this space. Escape to your own private oasis in the huge backyard with stunning deck that offers two areas, including a covered patio for morning coffee or peaceful rainy days. First floor offers the primary bedroom suite w/windows overlooking the gorgeous backyard. Upstairs you will see the soaring ceilings, custom finishes & sun filled loft. 2nd level offers 2 beds/1 bath with attic access for room to grow! Two attics. Dual pump septic system. Credit at closing for floors. A must see!

This historic C. 1830 Colonial house is beautifully sited and located at the end of a long private driveway. This spectacular 9 acre plus property is tranquil and nestled in a story book setting that overlooks a pond, frontage on the Wappingers Creek and spectacular waterfalls that you can hear from inside the house. Entertain family and friends on the deck that sits above the creek. Enjoy the gorgeous pool, open lawns, and majestic mature trees. The house has been thoughtfully updated preserving many original details. Original hard wood floors run throughout the house and there is an abundance of windows which lets in glowing natural light. The entry foyer opens onto the formal dining room and living room which has a lovely wood burning fireplace. The kitchen has been tastefully updated and there is an office/den. The laundry room and half bathroom complete the first floor. The Primary bedroom with en-suite full bathroom is on the second floor, and two additional bedrooms share an updated full bathroom. This is a unique property, a rare find. Close to the Taconic Parkway, shopping and restaurants. Close to Millbrook and Rhinebeck. Arlington School District.,AboveGrade:2070,ExteriorFeatures:Outside Lighting,Heating:Zoned,Other School:DUTCHESS,Unfinished Square Feet:400,ROOF:Asphalt Shingles,Below Grnd Sq Feet:400 Additional Information: HeatingFuel:Oil Above Ground,ParkingFeatures:1 Car Detached,

Pleasant Valley

Attractions

Community

Education

Entertainment

Food & Drinks

Healthcare

Hospitality

Miscellaneous

Parks

Shopping

Transportation

ListingSearchSimplev2

Listings

Search

Find homes, condos, and leases on the market using our powerful advanced search tools.

$415,000

$575,000

$469,000

$375,000

$79,999

$795,000

$399,000

$1,700

$689,000

$475,000

$549,000

$1,295,000

$489,000

$1,900

$289,900

$995,000

$600,000

$110,000

$675,000

$1,250,000

$215,000

$1,700

$589,800

$998,000

Company

Account

Services

Explore