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Pleasant Valley, NY Homes for Sale with Acreage

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  • /46

    $584,500

    • 4 Beds
    • 3 Baths
    • 2,600 Sq Ft

    89 Birch Dr, Pleasant Valley, NY 12569

    This spacious and impeccably maintained oversized raised ranch offers comfort, flexibility, and pride of ownership in every room.With a thoughtfully designed layout, this home features two bedrooms on the lower level and a primary suite with a private bath on the main floor, along with an additional bedroom—ideal for guests, family, or a home office.The heart of the home is the

    Agent Photo

    Philip Bisesto

    HomeSmart Homes & Estates

    (845) 681-2247

    89 Birch Dr, Pleasant Valley, NY 12569
  • /32

    $227,000

    • Land
    • 25 Acres
    • $9,062 per Acre

    00WP Rossway Rd, Pleasant Valley, NY 12569

    Welcome to your idyllic escape in the beautiful Hudson Valley town of Pleasant Valley, NY! This exceptional piece of property is a hidden gem, offering unmatched privacy and an abundance of natural beauty. Spanning acres of mixed hardwood and softwood species, the land is a harmonious blend of lush greenery and scenic vistas, providing the perfect backdrop for your dream project. Whether

    Mitchell Serlin WHITETAIL PROPERTIES REAL ESTATE LLC (NY)

    00WP Rossway Rd, Pleasant Valley, NY 12569
  • /36

    $3,500,000

    • 8 Beds
    • 4.5 Baths
    • 3,010 Sq Ft

    2045 Salt Point Turnpike, Salt Point, NY 12578

    Welcome to This Hudson Farm - a distinctive 157+ acre estate spanning 2039-2105 Salt Point Turnpike, where the beauty of the Hudson Valley meets the ultimate opportunity to enjoy as much--or as little--of the farming lifestyle as you desire. Positioned between Rhinebeck and Millbrook, and just minutes from the Taconic State Parkway, this remarkable offering blends historic charm with modern

    LINDSAY ROTHMAN

    2045 Salt Point Turnpike, Salt Point, NY 12578
  • /40

    $845,000

    • 3 Beds
    • 3.5 Baths
    • 2,567 Sq Ft

    69 Brown Rd, Pleasant Valley, NY 12569

    Welcome to your private country retreat! Tucked away down a gravel driveway you will find this charming home nestled on 11+ acres of nature, mostly wooded with a pond and a fine clearing around the home. The home features a comfortable floor plan - a wonderful country kitchen opens to a dining area with French doors leading into the light-filled great room, featuring a soaring ceiling and a

    Susan Whalen George T Whalen Real Estate

    69 Brown Rd, Pleasant Valley, NY 12569
  • /50

    $815,000

    • 6 Beds
    • 4.5 Baths
    • 3,974 Sq Ft

    82 Thornhill Dr, Pleasant Valley, NY 12569

    Stunning Pleasant Valley Colonial in park-like setting: This wonderful 6 bedroom home can be your personal oasis; close enough to civilization to have convenience, yet just rural enough to also have serenity. The acre and a half property features stately, landscaped front & side yards with walkways & mature trees - and a more private, fenced & wooded backyard that is all about relaxing and/or

    Christopher Hanson Hanson Real Estate Partners

    82 Thornhill Dr, Pleasant Valley, NY 12569
  • /43

    $1,300,000

    • 5 Beds
    • 3.5 Baths
    • 4,841 Sq Ft

    498 Rossway Rd, Pleasant Valley, NY 12569

    Looking for a private getaway or country full time home with Mother and daughter unit or additional income to pay the mortgage? Enter into a long driveway that takes you to the top of the hill to a sight of a beautiful contemporary home with 18 x 36 Inground Pool, Very unique and totally secluded! Nestling on 16.05 wooded acres, this custom appointed u-shape home is one of a kind! The main

    Arlene Campbell BHHS Hudson Valley Properties

    498 Rossway Rd, Pleasant Valley, NY 12569
  • /44

    $999,000

    • 4 Beds
    • 3.5 Baths
    • 4,024 Sq Ft

    12 Wolf Ln, Pleasant Valley, NY 12569

    Tucked away on over 14 acres of total privacy and tranquility, 12 Wolf Lane is a contemporary retreat offering 4,000+ square feet of beautifully designed living space and every amenity you could ask for. From the moment you arrive, you’ll feel the calm, surrounded by nature, fieldstone walls built with stone from the land itself, and the kind of seclusion that’s increasingly hard to

    Jake Garay Serhant LLC

    12 Wolf Ln, Pleasant Valley, NY 12569
  • /26

    $1,600,000

    • 6 Beds
    • 3.5 Baths
    • 4,248 Sq Ft

    11 Brown Rd, Pleasant Valley, NY 12569

    Step back in time without sacrificing modern comforts in this rare, historic brick farmhouse estate, originally built in the 1760s by early settler Sarah Tobias Newcomb. Rich in Revolutionary War-era history, this extraordinary property tells a story few homes can: Sarah famously sent cheese from her dairy to George Washington's encampment nearby. Over the years, the home has flown both British

    Daniel Colomban Skyler Realty LLC

    11 Brown Rd, Pleasant Valley, NY 12569
  • /29

    $900,000

    • 3 Beds
    • 2 Baths
    • 1,548 Sq Ft

    104 S Quaker Ln, Hyde Park, NY 12538

    Modern Farmhouse Retreat - Discover this beautifully reimagined 1870 farmhouse, set on over 25 private secluded acres in the heart of the Hudson Valley. Fully renovated in 2025 with modern finishes throughout, this 3-bedroom, 2-bath residence is a rare blend of historic charm and today’s design sensibility—perfect as a second home or peaceful weekend retreat.Tucked away down a long drive,

    Curtis Darragh Legacy Land & Homes LLC

    104 S Quaker Ln, Hyde Park, NY 12538
  • /37

    $1,525,000

    • 3 Beds
    • 2.5 Baths
    • 2,820 Sq Ft

    101 Drake Rd, Pleasant Valley, NY 12569

    CONVERTED BARNS WITH POOL. This charming getaway offers fun lofty spaces to gather, entertain and enjoy the countryside, while conveniently located to the TSP and Millbrook Village. This 19th century converted barn was beautifully preserved and showcases the exposed beams and wide board floors. Upon entering, one is enamored by the soaring vaulted ceilings with exposed beams in the center of the

    PAULA REDMOND Corcoran Country Living

    101 Drake Rd, Pleasant Valley, NY 12569
  • /35

    $1,179,000

    • 3 Beds
    • 2 Baths
    • 2,700 Sq Ft

    129 Clinton Corners Rd, Salt Point, NY 12578

    129 Clinton Corners Road, Salt Point, NYA rare and exceptional offering—this private 18.5-acre estate blends natural beauty, architectural charm, and modern updates, all in a prime location just off the Taconic Parkway for easy commuting.This stunning post-and-beam 4,300 sq ft contemporary home features soaring 25-foot cathedral ceilings, a central stone wood-burning fireplace, and

    Ginalea Healy K. Fortuna Realty, Inc.

    129 Clinton Corners Rd, Salt Point, NY 12578
  • /45

    $1,195,000

    • 4 Beds
    • 3.5 Baths
    • 3,888 Sq Ft

    27 Gallagher Dr, Pleasant Valley, NY 12569

    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

    Angelica Ferguson Houlihan Lawrence Inc.

    27 Gallagher Dr, Pleasant Valley, NY 12569
  • /12

    $273,000

    • 3 Beds
    • 1 Bath
    • 1,520 Sq Ft

    11 Demelis Dr, Pleasant Valley, NY 12569

    This charming Cape Cod style home features classic New England architecture with traditional design elements. The property offers comfortable living spaces and timeless appeal for discerning residents. This three-bedroom, one-bathroom home presents excellent investment opportunities for those seeking to build equity through strategic improvements. The property's solid foundation provides a

    Brian Smith River Realty Services, Inc.

    11 Demelis Dr, Pleasant Valley, NY 12569
  • /40

    $699,000

    • 4 Beds
    • 4 Baths
    • 4,160 Sq Ft

    303 Freedom Rd, Pleasant Valley, NY 12569

    Custom 4 bedroom, 2 full bath, 2 half bath contemporary privately set on 5 acre parcel. Surrounded by wooded buffers for privacy, this nature lover's paradise is the perfect venue for entertaining. Attractive floor plan includes huge eat-in kitchen complete with center island & stainless appliances. Living room w/fireplace provides easy access to deck overlooking expansive yard. First floor

    Dan Axtmann BHHS Hudson Valley Properties

    303 Freedom Rd, Pleasant Valley, NY 12569
  • /45

    $750,000

    • 4 Beds
    • 2.5 Baths
    • 3,019 Sq Ft

    41 Meddaugh Rd, Pleasant Valley, NY 12569

    Why settle for basic new construction when you can enjoy more space, privacy, and luxurious finishes in this beautifully renovated 4-bedroom, 2.5-bathroom home in the Arlington Central School District? From the moment you enter, you're welcomed by wide-plank white oak hardwood floors and an abundance of natural light pouring in through oversized picture windows that seamlessly connect the indoors

    Gregory Pikor Inspire Realty

    41 Meddaugh Rd, Pleasant Valley, NY 12569
  • /23

    $260,000

    • 2 Beds
    • 1 Bath
    • 916 Sq Ft

    1253 Salt Point Turnpike, Pleasant Valley, NY 12569

    This move-in ready 1949 traditional cottage sits on 1.3 picturesque acres in the heart of the Hudson Valley. Thoughtfully preserved with original wood flooring, trim, and a charming wooden scalloped eave awning, the home offers timeless character and warm curb appeal. Inside, you'll find two bedrooms plus an additional laundry room that could flex as a home office. Exterior features include

    Susan Whalen George T Whalen Real Estate

    1253 Salt Point Turnpike, Pleasant Valley, NY 12569
  • /23

    $225,000

    • Land
    • 5 Acres
    • $44,643 per Acre

    L510455 Creek Rd, Pleasant Valley, NY 12569

    Situated on Creek Rd, along Wappinger Creek in the desirable town of Pleasant Valley, this 5.04 acres site is ready for your site improvements and building. The driveway has already been rough cut in with the location for the house accessible for further clearing and site preparation. Current BOH approved with proposed site location for house, well, and septic. Bring your contractor and architect

    Gary Martin Compass Greater NY LLC

    L510455 Creek Rd, Pleasant Valley, NY 12569
  • /18

    $225,000

    • Land
    • 5 Acres
    • $44,643 per Acre

    0 Creek Rd Unit KEY896908, Pleasant Valley, NY 12569

    Situated on Creek Rd, along Wappinger Creek in the desirable town of Pleasant Valley, this 5.04 acres site is ready for your site improvements and building. The driveway has already been rough cut in with the location for the house accessible for further clearing and site preparation. Current BOH approved with proposed site location for house, well, and septic. Bring your contractor and architect

    Gary Martin Compass Greater NY, LLC

    0 Creek Rd Unit KEY896908, Pleasant Valley, NY 12569
  • /23

    $225,000

    • Land
    • 5 Acres
    • $44,643 per Acre

    Tbd Creek Rd, Pleasant Valley, NY 12569

    Situated on Creek Rd, along Wappinger Creek in the desirable town of Pleasant Valley, this 5.04 acres site is ready for your site improvements and building. The driveway has already been rough cut in with the location for the house accessible for further clearing and site preparation. Current BOH approved with proposed site location for house, well, and septic. Bring your contractor and architect

    Gary Martin Compass Greater NY, LLC d/b/a

    Tbd Creek Rd, Pleasant Valley, NY 12569
  • /31

    $549,000

    • 3 Beds
    • 2 Baths
    • 2,300 Sq Ft

    844 Salt Point Turnpike, Poughkeepsie, NY 12601

    Accepted Offer.. No more showings please.....A MASTER CRAFTSMAN'S HOME! Obviously the one to own, The love and attention to detail is all TOP SHELF. This family has rasied their family here and now as they retire they turn over their labor of LOVE to you the next owner. Privately tucked off the road professionally Landscaped by Nolan Nurserys now the mature landscaping shields the home from any

    Brian Woolsey BHHS Hudson Valley Properties

    844 Salt Point Turnpike, Poughkeepsie, NY 12601
  • /45

    $489,000 Open Sat 11AM - 1PM

    • 2 Beds
    • 2 Baths
    • 1,518 Sq Ft

    26 Carter Rd, Pleasant Valley, NY 12569

    Welcome to 26 Carter Rd, Pleasant Valley! Nestled on 3.5 private acres, this versatile 2-bedroom home lives like a 3, offering a flexible third room perfect for an office, guest space, or hobby area. Enjoy 2 full baths and a stunning, oversized gourmet kitchen featuring quartz countertops—ideal for chefs and entertainers alike. Experience the best of country living with space, privacy, and modern

    Shawn Pitcher KFortuna All Aspects Realty

    26 Carter Rd, Pleasant Valley, NY 12569
  • /27

    $349,000

    • 3 Beds
    • 1 Bath
    • 920 Sq Ft

    387 Freedom Rd, Pleasant Valley, NY 12569

    Discover the potential at 387 Freedom Road—a 3-bed, 1-bath in the highly sought after Arlington School District. This well maintained home is set back off the road on an acre of land and offers peace, privacy, and charm. A welcoming front porch is the perfect spot to take in the natural surroundings, while enjoying your morning coffee. Inside features include luxury vinyl plank flooring

    John Gabriel Jr KW MidHudson

    387 Freedom Rd, Pleasant Valley, NY 12569
  • /4

    $79,000

    • Land
    • 1.30 Acres
    • $60,769 per Acre

    0 New York 82, Pleasant Valley, NY 12569

    UNTOUCHED and never on the market since 1968! PRICED TO SELL!1.3 beautiful acres on a scenic country road. Zoned RA3, build your dream home and bring your farming skills with you!Bucolic and private, these gems are rare and hard to find. Priced for immediate attention!

    Randy Calano Keller Williams Realty Partner

    0 New York 82, Pleasant Valley, NY 12569
  • /38

    $2,195,000

    • 4 Beds
    • 4.5 Baths
    • 6,452 Sq Ft

    189 Freedom Rd, Pleasant Valley, NY 12569

    An Enchanting Stone Manor-First Time Offered. Set amidst exquisitely landscaped grounds in the heart of the Hudson Valley, this extraordinary stone manor is a triumph of design, craftsmanship, and setting—gracefully secluded, yet just minutes from the bucolic village of Millbrook. Meticulously conceived and built to the highest standards, the estate is being offered for the very first

    Jill Rose Houlihan Lawrence Inc.

    189 Freedom Rd, Pleasant Valley, NY 12569
  • /50

    $2,995,000

    • 4 Beds
    • 7 Baths
    • 6,412 Sq Ft

    165 Drake Rd, Pleasant Valley, NY 12569

    Welcome to Timber Lake Farm, a stunning property in the heart of Dutchess County horse country. This Adirondack-style estate offers a harmonious blend of rustic elegance and modern luxury, set on 33.26-acre lot with a pristine 9-acre pond that flows over a waterfall at one end. The bespoke stone and wood home boasts 6,412 square feet of living space sited at the highest elevation point on the

    Kyle Irwin Corcoran Country Living

    165 Drake Rd, Pleasant Valley, NY 12569
  • /19

    $519,999

    • 5 Beds
    • 4 Baths

    185 Creek Rd, Pleasant Valley, NY 12569

    Welcome to your own private retreat! This two-family home offers a peaceful, park-like setting with a creek right in your backyard—perfect for fishing or simply unwinding by the water. The home is set back from the road, offering privacy and serenity, with stairs leading down to the creek and multiple decks for relaxing or entertaining.Inside, you'll find an open floor plan that features

    Anthony Melella Vision Alliance Realty Inc.

    185 Creek Rd, Pleasant Valley, NY 12569
  • /50

    $1,179,000

    • 4 Beds
    • 4.5 Baths
    • 6,085 Sq Ft

    37 Patricia Dr, Pleasant Valley, NY 12569

    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

    Jake Garay Serhant LLC

    37 Patricia Dr, Pleasant Valley, NY 12569
  • /40

    $1,815,000

    380 Freedom Rd, Pleasant Valley, NY 12569

    PRICE REDUCED!! The sellers are also willing to negotiate terms for seller financing. This is your opportunity to own a slice of history and pastoral beauty in the heart of Pleasant Valley, NY. This 138.4-acre dairy farm combines fertile land with panoramic views and endless possibilities, making it an ideal investment for farming, recreation, or development. The land has not had any in organic

    Mitchell Serlin WHITETAIL PROPERTIES REAL ESTATE LLC (NY)

    380 Freedom Rd, Pleasant Valley, NY 12569
  • /6

    $240,000

    • Land
    • 29 Acres
    • $8,219 per Acre

    0 James Way Unit ONEH6325454, Pleasant Valley, NY 12569

    Attention builders. 2 parcels totaling 29.2 acres with approximately 18 acres of level cleared land. Definitely worth taking a look at this wonderful property with subdivision possibilities. Located at the end of the road. Property includes parcel 1344006363033554200000. Assessment and taxes are the total for both parcels.

    Judy Lancia

    0 James Way Unit ONEH6325454, Pleasant Valley, NY 12569
  • /4

    $79,000

    • Land
    • 1.18 Acres
    • $66,949 per Acre

    0 Creek Rd Unit ONEH6271048, Pleasant Valley, NY 12569

    Beautiful lot, almost 2 wooded acres, board of health approved, in town of Pleasant Valley. Close to village, TSP, 15 mins to Poughkeepsie and train station.

    Graziano Tassone Tassone Realty Corp.

    0 Creek Rd Unit ONEH6271048, Pleasant Valley, NY 12569
  • /2

    $169,000

    • Land
    • 2.05 Acres
    • $82,439 per Acre

    35 Patricia Dr, Pleasant Valley, NY 12569

    Discover the perfect setting for your future home on this scenic 2+ acre lot, nestled in a well-established and desirable neighborhood. Board of Health approval is already in place, making it easier to start your build. Bring your own builder, or contact us to explore custom home options tailored to your vision.

    Jake Garay Serhant LLC

    35 Patricia Dr, Pleasant Valley, NY 12569
  • /2

    $90,000

    • Land
    • 3.58 Acres
    • $25,140 per Acre

    235 Pine Hill Rd, Pleasant Valley, NY 12569

    THIS BEAUTIFUL PROPERTY IN PLEASANT VALLEY NEW YORK OFFERS THE PERFECT OPPORTUNITY TO OWN NEAR THE SCENIC HUDSON RIVER VALLEY. LOCATED CLOSE TO POUGHKEEPSIE, THIS LAND PROVIDES EASY ACCESS TO OUTDOOR ACTIVITIES. A CHARMING COMMUNITY WITH A RICH HISTORY AND FRIENDLY ATMOSPHERE OFFERING A SERENE LIFESTYLE WHILE BEING APPROXIMATELY 2 HOUR DRIVE TO NEW YORK CITY.

    ALISON NIXON eXp Realty

    235 Pine Hill Rd, Pleasant Valley, NY 12569
  • /30

    $600,000

    • 1 Bed
    • 1 Bath
    • 960 Sq Ft

    4 Browning Rd, Salt Point, NY 12578

    This is a unique horse property with endless opportunities awaiting you. The massive barn on the property is full of character, with various additions dating back to the late 1800s up to the 1990s. With over 24 horse stalls and ample storage on the upper level, this 7500 sq ft structure can be used for a variety of purposes.In addition to the barn, there is a charming 1 bedroom cottage on

    EUGENE VALOY BHHS Hudson Valley Properties

    4 Browning Rd, Salt Point, NY 12578

Home Trends in Pleasant Valley, NY

Housing Trends

Median Sale Price
$485,000
Median Single Family Sale Price
$489,000
Median Townhouse Sale Price
$475,000
Average Price Per Sq Ft
$277
Number of Homes for Sale
23
Last 12 months Home Sales
73
Months of Supply
3.80
Median List Price
$530,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
20%
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