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Homes for Sale in 12569

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  • /46

    $700,000

    • 4 Beds
    • 3.5 Baths
    • 3,400 Sq Ft

    21 Straub Dr, Pleasant Valley, NY 12569

    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

    Agent Photo

    Peter Quartironi

    RE/MAX Town & Country

    (845) 681-6538

    21 Straub Dr, Pleasant Valley, NY 12569
  • /34

    $835,000

    $15K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 4,657 Sq Ft

    159 Rombout Rd, Poughkeepsie, NY 12603

    Experience refined living in this stunning Great Hall Colonial, offering 3,225 sq ft of thoughtfully designed luxury. A dramatic Great Hall with open-air overlook creates an impressive architectural centerpiece, seamlessly connecting both levels. This elegant home features 4 bedrooms and 3.5 baths, including a luxurious primary suite with a spa-like bath and dual walk-in closets, plus a private

    Agent Photo

    Haakim Byrd

    HomeSmart Homes & Estates

    (845) 280-6179

    159 Rombout Rd, Poughkeepsie, NY 12603
  • /15

    $1,200,000

    • Land
    • 124.19 Acres
    • $9,663 per Acre

    2010 Salt Point Turnpike, Pleasant Valley, NY 12569

    Beautiful farming land, currently 2 adjoining tax lots with creek running through one parcel. Currently enrolled in Conservation Easement with designated building envelope. 80-90% tillable.

    David Birch Barns and Farms Realty LLC

    2010 Salt Point Turnpike, Pleasant Valley, NY 12569
  • /23

    $399,000

    $21K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,200 Sq Ft

    1379 Route 44, Pleasant Valley, NY 12569

    This Pleasant Valley Colonial in the Arlington School District offers a blend of classic character and practical updates on a spacious 0.62-acre lot. With 3 bedrooms and 2 full baths across 1,584 square feet, the layout includes a large living room with hardwood floors and a wood-burning fireplace, plus a formal dining room with French doors that create a natural flow for everyday living and

    Virginia Corbett eXp Realty

    1379 Route 44, Pleasant Valley, NY 12569
  • /24

    $189,900

    • 3 Beds
    • 2 Baths
    • 880 Sq Ft

    69 View Dr, Pleasant Valley, NY 12569

    Brand new manufactured home in desirable Hickory Hills Estates! This beautiful 3-bedroom, 2-bath residence blends modern contemporary style with everyday functionality—perfectly situated in a fantastic commuter-friendly location. With nearly 1,000 sq ft of bright and airy living space, this home is designed for comfort, convenience, and style. Wide-open floor plan that effortlessly connects the

    Sandra Spector Howard Hanna Rand Realty

    69 View Dr, Pleasant Valley, NY 12569
  • /20

    $549,000

    • 2 Beds
    • 2.5 Baths
    • 1,364 Sq Ft

    17 Gretna Hill Rd, Pleasant Valley, NY 12569

    Circular driveway to an All new renovation in beautiful Gretna Hill wooded neighborhood, elegant farms beyond. Mahogany full glass door entry on to black marble foyer. Spacious living/dining room, mahogany doors and trim. Full glass exterior door to 12' x 18' Japanese cedar deck. Hardwood floors throughout. Natural wood and marble kitchen with artisanal details, huge quartz worktop, new

    Derek Greene Greene Realty Group

    17 Gretna Hill Rd, Pleasant Valley, NY 12569
  • /13

    $218,400

    $12K PRICE DROP
    • Land
    • 4.81 Acres
    • $45,405 per Acre

    0 Freedom Rd Unit KEY913491, La Grange, NY 12569

    4.81 Acre Parcel in the Heart of Lagrange Discover the perfect blend of privacy and convenience with this 4.81-acre wooded parcel in the heart of Lagrange. Nestled in a peaceful natural setting, yet just minutes to everything the Hudson Valley has to offer, this location is ideal for your dream home—or for a potential small subdivision. Commuters will appreciate the easy access to the Taconic

    Michael Tellerday Houlihan Lawrence Inc.

    0 Freedom Rd Unit KEY913491, La Grange, NY 12569
  • /38

    $975,000

    • 4 Beds
    • 2.5 Baths
    • 3,606 Sq Ft

    136 Rombout Rd, Pleasant Valley, NY 12569

    Welcome to Rombout Retreat! A spacious four bedroom, three bath home offering over 3,000 square feet of beautifully maintained living space on two private acres surrounded by protected agricultural land. This thoughtfully designed home offers multiple living spaces, each with its own warm and inviting atmosphere, with fireplaces in every sitting room as well as an additional fireplace in the

    Audrey Winslow Houlihan Lawrence Inc.

    136 Rombout Rd, Pleasant Valley, NY 12569
  • /30

    $649,900

    • 4 Beds
    • 2 Baths
    • 3,346 Sq Ft

    15 Rock Cut Ln, Pleasant Valley, NY 12569

    Welcome home to 15 Rock Cut Ln, a property that underwent a complete renovation in 2022 with both intention and functionality at the forefront. From the brand-new roof, siding, and windows to the upgraded, reinforced, and waterproofed foundation, this total overhaul presents a home designed for peace of mind and true move-in-ready living. New electrical, heating, plumbing, and septic systems

    KYLE JOHNSON SR. Clarke Realty & Associates LLC

    15 Rock Cut Ln, Pleasant Valley, NY 12569
  • /25

    $470,000

    • 3 Beds
    • 1.5 Baths
    • 1,932 Sq Ft

    15 Whiteford Dr, Pleasant Valley, NY 12569

    Welcome to this beautifully updated 4 Bedroom home in the heart of Pleasant Valley! Located in a quiet, walkable neighborhood, this property offers the perfect blend of comfort, convenience, and charm. Step inside to find refinished hardwood floors that bring warmth and character throughout the main living areas. The home features fresh paint from top to bottom, creating a bright, clean, and

    Matthew Skowronski HomeSmart Homes & Estates

    15 Whiteford Dr, Pleasant Valley, NY 12569
  • /38

    $975,000

    • 4 Beds
    • 2.5 Baths
    • 4,221 Sq Ft

    136 Rombout Rd, Poughkeepsie, NY 12603

    Welcome to Rombout Retreat! A spacious four bedroom, three bath home offering over 3,000 square feet of beautifully maintained living space on two private acres surrounded by protected agricultural land. This thoughtfully designed home offers multiple living spaces, each with its own warm and inviting atmosphere, with fireplaces in every sitting room as well as an additional fireplace in the

    Danielle Dropkin Houlihan Lawrence Inc.

    136 Rombout Rd, Poughkeepsie, NY 12603
  • /47

    $625,000

    • 2 Beds
    • 1.5 Baths
    • 1,368 Sq Ft

    145 Drake Rd, Pleasant Valley, NY 12569

    Welcome to Turtle Pond Gully, a delightful property in the Hudson Valley. Enjoy country life in this sweet colonial farmhouse located in the town of Pleasant Valley. This 1930s cottage offers immense charm and is the perfect retreat for weekenders or year-round residents. The light-filled home offers a cozy and comfortable interior with beautiful wood floors. Many original details have been

    Susan Whalen George T Whalen Real Estate

    145 Drake Rd, Pleasant Valley, NY 12569
  • /50

    $649,000

    • 3 Beds
    • 2 Baths
    • 3,000 Sq Ft

    94 Gretna Rd, Pleasant Valley, NY 12569

    Welcome to this stunningly renovated 3-bedroom, 2-bath ranch perfectly situated on a serene half-acre lot in the desirable Arlington district. Thoughtfully re-designed from top to bottom, this 1958 home offers the ideal blend of charm, sophistication, and modern convenience. The custom chef's kitchen anchors the home with style and functionality, while beautifully refinished oak floors flow

    Christina Naula BHHS Hudson Valley Properties

    94 Gretna Rd, Pleasant Valley, NY 12569
  • /36

    $699,000

    $40K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,483 Sq Ft

    76 Rockledge Dr, Pleasant Valley, NY 12569

    A rare and very desirable combination of excellent location, community, privacy and classic styling. Set on 1.3 acres on a quiet, no-outlet subdivision of approximately 30 homes, this spacious and well maintained home is being offered by the original owners. The location is superb. The Taconic Parkway, high school, middle school, primary school, town library, grocery store and more are all within

    Dan Axtmann BHHS Hudson Valley Properties

    76 Rockledge Dr, Pleasant Valley, NY 12569
  • /25

    $1,595,000

    • Land
    • 76.52 Acres
    • $20,844 per Acre

    641 North Ave, Pleasant Valley, NY 12569

    Tucked away off the well-traveled path and largely unnoticed, this remarkable 76± acre private parcel offers breathtaking distant and valley views in the heart of the Hudson Valley, just a short drive from sought-after destinations such as Rhinebeck and Millbrook. Currently operating as a successful apple orchard, the property features approximately 50 acres planted with 5 varieties of

    Carey Whalen Compass Greater NY, LLC

    641 North Ave, Pleasant Valley, NY 12569
  • /26

    $1,750,000

    $500K PRICE INCREASE
    • 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
  • /45

    $659,000

    • 4 Beds
    • 2.5 Baths
    • 2,248 Sq Ft

    125 Smith Rd, Pleasant Valley, NY 12569

    You could be living the dream! Enjoy the best of one level living. Set on 2.23 scenic acres, this beautifully maintained expanded ranch home offers a wonderful blend of comfort, thoughtful updates, and exceptional outdoor amenities. With 2,248 finished square feet, 4 bedrooms, 2.5 remodeled baths, wood burning fireplace the home provides a spacious and functional layout suited to a variety of

    Pamela Kandel

    125 Smith Rd, Pleasant Valley, NY 12569
  • /49

    $849,000

    • 4 Beds
    • 2.5 Baths
    • 2,924 Sq Ft

    32 Cole Rd, Pleasant Valley, NY 12569

    Welcome to your private Hudson Valley retreat—an estate-style residence set on 13.7 picturesque, park-like acres in the heart of LaGrange, just minutes from the charming village of Millbrook. A serene quarter-mile partially pine-lined driveway creates a memorable arrival experience, immediately setting the tone for the privacy, scale, and tranquility that define this exceptional property.

    SOPHIA NAEEM

    32 Cole Rd, Pleasant Valley, NY 12569
  • /3

    $775,000

    • Land
    • 10.52 Acres
    • $73,669 per Acre

    332 Creek Rd, Pleasant Valley, NY 12569

    Stephen Tocco TOCCO GROUP LTD

    332 Creek Rd, Pleasant Valley, NY 12569
  • /28

    $779,000

    New Construction $20K PRICE INCREASE
    • 4 Beds
    • 2.5 Baths
    • 2,434 Sq Ft

    989 Freedom Rd, Pleasant Valley, NY 12569

    TO BE BUILT: Introducing the wildly-popular Jefferson model, a colonial-style home in Arlington School District on almost 2 acres! Highlights of this 4 BR 2.5 bath include: 9' first floor ceilings, an expansive open concept kitchen, breakfast area and family room with a fireplace, home office, master bedroom suite with tray ceiling, second floor laundry and 2 car garage. Generous-sized bedrooms,

    John Gabriel Jr KW MidHudson

    989 Freedom Rd, Pleasant Valley, NY 12569
  • /12

    $499,999

    • 4 Beds
    • 2.5 Baths
    • 2,912 Sq Ft

    47 Mountain View Dr, Pleasant Valley, NY 12569

    Welcome to 47 Mountain View Drive a privately situated 4-bedroom, 2.5 bath raised ranch nestled on a quiet 1-acre lot in Pleasant Valley, NY. The heavy lifting is already done here. Major mechanical upgrades are complete including a new electrical panel, new PVC and copper plumbing lines, a new furnace, a water softener, and a newer water well pressure tank — giving you a rock-solid foundation

    Jahnny Crespo RE/MAX Town & Country

    47 Mountain View Dr, Pleasant Valley, NY 12569
  • /29

    $415,000

    $15K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,132 Sq Ft

    182 Downing Rd, Pleasant Valley, NY 12569

    Commuter's Dream Ranch with West-Facing Views & WorkshopLocation, Privacy, and Convenience! Beautiful Ranch situated on a private 2.6-acre lot in Pleasant Valley. This home offers the ultimate balance: incredibly close to the Taconic State Parkway for an easy commute, yet tucked away in a quiet area that feels far removed from the hustle. Key Features Include:Outdoor Living: Hear the

    Christine Hamilton Keller Williams Realty Partner

    182 Downing Rd, Pleasant Valley, NY 12569
  • /31

    $582,000

    • 3 Beds
    • 2 Baths
    • 1,824 Sq Ft

    176 Downing Rd, Pleasant Valley, NY 12569

    The Ultimate Hudson Valley Retreat: Private Living Meets an Enthusiast’s DreamEscape to your own private, tree-lined sanctuary in Pleasant Valley. Tucked away in the highly desirable Arlington School District, this custom-built, 1.7-story residence offers the perfect blend of country living, efficiency, and unmatched mechanical utility. From the moment you arrive, the towering trees and

    Christine Hamilton Keller Williams Realty Partner

    176 Downing Rd, Pleasant Valley, NY 12569
  • /40

    $675,000

    • 4 Beds
    • 3.5 Baths
    • 3,041 Sq Ft

    343 North Ave, Pleasant Valley, NY 12569

    Set far back from the road on 4.63 beautifully manicured acres and surrounded by protected land that will not be built on, this exceptional 3,041 SqFt front porch Colonial offers a rare combination of privacy, tranquility, and long-term peace of mind. A picturesque gently curving 650-foot driveway leads you through a serene, park-like setting, creating a true estate feel and a daily escape from

    John Durso Keller Williams Realty Partner

    343 North Ave, Pleasant Valley, NY 12569
  • /39

    $495,000

    • 4 Beds
    • 3 Baths
    • 2,169 Sq Ft

    176 Gretna Woods Rd, Pleasant Valley, NY 12569

    Nothing has been left to question for the lucky new owners of this amazing home!This generously oversized bi-level ranch will surely impress you on entry, with extra details not typically found in homes of this caliber. Walls and ceilings with natural wood andwainscotting add a warm vibe to the foyer and three season sunroom off of the kitchen, which is equipped with windows and screens, to

    Adrienne Volpe KW MidHudson

    176 Gretna Woods Rd, Pleasant Valley, NY 12569
  • /50

    $799,900

    $30K PRICE DROP
    • 6 Beds
    • 4 Baths

    949 Freedom Rd, Pleasant Valley, NY 12569

    Step into a storybook setting with this extraordinary one-of-a-kind property! Featuring TWO homes on 2 picturesque acres: a circa 1900 farmhouse (4 beds/3 full baths - 2,674 sq. ft.) originally built from Sears Roebuck and Co. kit plans and with materials that were delivered by train, AND a second home (2 beds/1bath - 1,080 sq. ft.) ideal for multi-generational living, rental income or guest

    Jennifer Amicucci

    949 Freedom Rd, Pleasant Valley, NY 12569
  • /22

    $475,000

    $25K PRICE INCREASE
    • 3 Beds
    • 3 Baths
    • 1,800 Sq Ft

    25 Mcallister Dr, Pleasant Valley, NY 12569

    Tucked away on just over an acre in a quiet Pleasant Valley neighborhood, this inviting three-bedroom home offers the kind of space and convenience that makes Hudson Valley living feel easy. With hardwood floors throughout, a finished basement. The property blends comfort, flexibility, and outdoor living in all the right ways.Inside, the layout is warm and functional, with three bedrooms, one

    Emmanuel Jimenez Compass Greater NY, LLC

    25 Mcallister Dr, Pleasant Valley, NY 12569
  • /47

    $1,195,000

    $180K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,820 Sq Ft

    101 Drake Rd, Pleasant Valley, NY 12569

    Seller says to sell now!Tucked behind a quiet country approach, two meticulously restored 19th-century barns have been reimagined into a refined luxury residence and companion pool house that feel timeless in character and elevated in execution. Inside the main residence, soaring vaulted ceilings, original hand-hewn beams, and wide-plank floors establish a sense of warmth and permanence,

    Jake Garay Serhant LLC

    101 Drake Rd, Pleasant Valley, NY 12569
  • /4

    $179,900

    • Land
    • 5.04 Acres
    • $35,694 per Acre

    0 Creek Rd Unit KEY981346, Pleasant Valley, NY 12569

    Build your dream home on this beautiful 5-acre Board of Health approved parcel in Pleasant Valley, where privacy, natural beauty, and opportunity come together. This exceptional property offers a rare chance to create a custom home or private retreat in a peaceful Hudson Valley setting.Surrounded by mature trees and scenic countryside, the land provides the perfect backdrop for your vision.

    Robert Villone RE/MAX Classic Realty

    0 Creek Rd Unit KEY981346, Pleasant Valley, NY 12569
  • /39

    $574,900

    • 4 Beds
    • 2.5 Baths
    • 2,284 Sq Ft

    316 Forest Valley Rd, Pleasant Valley, NY 12569

    Welcome to this beautifully maintained Colonial, proudly offered by its original owner and set on 1.43 private acres with an exceptional backyard retreat in the Valley Dale area. Combining timeless charm with thoughtful updates, this 4-bedroom, 2.5-bath home is designed for comfortable everyday living and effortless entertaining. The inviting living room features hardwood floors and a classic

    Bonnie Massa BHHS Hudson Valley Properties

    316 Forest Valley Rd, Pleasant Valley, NY 12569
  • /37

    $795,000

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

    41 Meddaugh Rd, Pleasant Valley, NY 12569

    41 Meddaugh Road is sited on 1.84 acres set back from the road and has been extensively renovated through a comprehensive ground-up transformation. Nearly all major systems, structural components, and finishes were replaced or upgraded during this full gut renovation, where everything from the studs inward was redone and the home’s exterior systems were completely updated, resulting in a move-in

    Kyle Irwin Corcoran Country Living

    41 Meddaugh Rd, Pleasant Valley, NY 12569
  • /35

    $549,990

    • 4 Beds
    • 1.5 Baths
    • 2,424 Sq Ft

    53 Tyrrel Rd, Pleasant Valley, NY 12569

    Nestled at the top of a meandering driveway, this charming four bedroom ranch offers privacy, and scenic views in an ideal location. Situated on six serene acres within the desirable Arlington School District, this home combines comfort, space and solitude. Cherished by the same family for over 30 years, where countless memories were created hosting large joyful gatherings and small intimate

    Janet Myer Houlihan Lawrence Inc.

    53 Tyrrel Rd, Pleasant Valley, NY 12569
  • /30

    $375,000

    • 3 Beds
    • 2 Baths
    • 2,232 Sq Ft

    1666 Main St, Pleasant Valley, NY 12569

    Welcome to 1666 Main Street, a beautifully renovated classic early-1900s home in the heart of Pleasant Valley. This move-in ready property offers 3–4 bedrooms, 2 full baths, and over 2,000 square feet of living space on a low-maintenance .20-acre lot in the Arlington School District with low taxes. Inside, you’ll find refinished 100+ year-old Maple and Douglas Fir hardwood floors, upgraded

    Kiyoshi Henson RE/MAX Town & Country

    1666 Main St, Pleasant Valley, NY 12569
  • /30

    $899,000

    New Construction $4K PRICE INCREASE
    • 4 Beds
    • 2.5 Baths
    • 3,011 Sq Ft

    991 Freedom Rd, Pleasant Valley, NY 12569

    TO BE BUILT – The Ellington Model Colonial on Over 3 Acres!This stunning 4-bedroom, 2.5-bath colonial offers the perfect blend of elegance and functionality. Highlights include a charming covered front porch, a dramatic two-story entry foyer and second-floor catwalk. The thoughtfully designed main level features a formal living room and dining room flanking the foyer. The spacious two-story

    John Gabriel Jr KW MidHudson

    991 Freedom Rd, Pleasant Valley, NY 12569
  • /33

    $399,000

    $51K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,908 Sq Ft

    106 Skidmore Rd, Lagrangeville, NY 12540

    Welcome home to this charming Cape style home at 106 Skidmore Rd, La Grangeville, NY 12540 on Spout Creek with the Arlington School District. This delightful residence boasts an expansive floor plan, offering over 1,900 square feet of versatile living space, perfectly designed for you to add your personal touches and truly make it your own. As you enter the main living level, the home offers a

    Kaye Saglibene

    106 Skidmore Rd, Lagrangeville, NY 12540
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