Wassaic, NY Homes for Sale

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  $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
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  /45

  $749,000

  • 3 Beds
  • 2 Baths
  • 1,706 Sq Ft

  22 Haight Ave, Millbrook, NY 12545

  Charming Cape Cod style home with thoughtful updates and wonderful natural light throughout. The first floor features a fully renovated kitchen with a cheerful breakfast bar, a living room with wood-burning fireplace, a sunroom overlooking the lovely backyard, a full bathroom, a bedroom, and an office. Upstairs, you will find another well-proportioned bedroom, a second full bath and a large

  Susan Whalen George T Whalen Real Estate

  22 Haight Ave, Millbrook, NY 12545
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  /40

  $149,000

  Open Sun 12PM - 2PM

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft

  17 Partridge Ln, Pleasant Valley, NY 12569

  Enjoy private, low-maintenance living in the Arlington School District! This well-maintained 2-bedroom, 2 full bath home offers a spacious and functional layout designed for comfortable everyday living. The large eat-in kitchen flows into a dedicated dining room, while the inviting living room features skylights that fill the space with natural light. An attached den provides the perfect flex

  Jessica Rosvold KW MidHudson

  17 Partridge Ln, Pleasant Valley, NY 12569
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  $479,000

  $166K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,598 Sq Ft

  121 Stanford Rd, Millbrook, NY 12545

  Here is a rare opportunity to acquire a slice of Millbrook history. The original Millbrook Toll House Circa 1890, built alongside the Wappingers Creek at the Arch Bridge is a true gem. The Toll House has been lovingly restored, preserved, and maintained, with an utmost respect for its grace, integrity and historical significance. Exposed beams/hardwood pristine, whimsical nooks and crannies

  Terese Mondello MONDELLO UPSTATE PROPERTIES LLC

  121 Stanford Rd, Millbrook, NY 12545
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  /45

  $900,000

  • 4 Beds
  • 6.5 Baths
  • 5,050 Sq Ft

  3534 Route 82, Millbrook, NY 12545

  Discover a truly unique Millbrook estate set on over 6 acres with a private pond, fruit trees, and beautiful natural surroundings. This expansive stone and brick residence offers remarkable craftsmanship and imported finishes, including marble and other materials brought in directly from Italy. Designed for both elegance and comfort, the home features multiple kitchens, two formal dining rooms,

  Christian Baez KW Hudson Valley United

  3534 Route 82, Millbrook, NY 12545
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  /31

  $495,000

  $87K PRICE DROP

  • 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
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  /49

  $4,250,000

  • 4 Beds
  • 5 Baths
  • 4,253 Sq Ft

  296-302 Stanford Rd, Millbrook, NY 12545

  Completely reimagined and renovated in 2026, this exceptional Millbrook compound offers an extraordinary blend of timeless architecture, modern luxury, and refined craftsmanship. Set on 18.92 private acres, the property encompasses a beautifully updated four or five bedroom, three full and two half bath main residence and a separate two bedroom, two and a half bath guest house. A dramatic formal

  Paula Redmond Corcoran Country Living - Mill

  296-302 Stanford Rd, Millbrook, NY 12545
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  /30

  $360,000

  • 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
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  $1,625,000

  • 3 Beds
  • 2 Baths
  • 3,035 Sq Ft

  46 Hoxie Rd, Millbrook, NY 12545

  Calling all dreamers, this unique, architect-designed contemporary residence is set on 25 private, wooded acres in Millbrook, New York. Located on a pastoral country road, and neighboring one of Millbrook's grand estate properties, this offering combines exceptional architectural integrity, quality construction, and future development potential. The light-filled home is defined by soaring 30-foot

  E. ELIZABETH PETERS Corcoran Country Living

  46 Hoxie Rd, Millbrook, NY 12545
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  /39

  $575,000

  $74K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 2,576 Sq Ft

  6 Route 343, Millbrook, NY 12545

  Owner listening to all offers. Welcome to this warm and inviting 3-bedroom, 1.5-bath home nestled in the heart of Dutchess County, just minutes from the Village of Millbrook and the Taconic State Parkway. From the moment you step into the entry foyer, you'll feel the character and comfort this home has to offer.The sun-filled living room impresses with a beamed ceiling and wood-burning

  Rebecca Marino Corcoran Country Living

  6 Route 343, Millbrook, NY 12545
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  /45

  $800,000

  • 4 Beds
  • 2.5 Baths
  • 3,263 Sq Ft

  32 Cole Rd, Pleasant Valley, NY 12569

  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

  Nicole Porter

  32 Cole Rd, Pleasant Valley, NY 12569
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  /50

  $650,000

  • 5 Beds
  • 3 Baths
  • 2,936 Sq Ft

  133 N Smith Rd, Lagrangeville, NY 12540

  RARE FIND.......Tucked away on 1.23 private acres in desirable LaGrangeville, this beautifully maintained duplex offers the perfect blend of comfort, flexibility, and opportunity. Surrounded by mature trees and peaceful countryside, the property provides a private retreat while remaining conveniently located near the Taconic State Parkway, Routes 55 and 82, Millbrook Village, parks, dining, and

  Arleen Sepulveda KW Hudson Valley North

  133 N Smith Rd, Lagrangeville, NY 12540
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  /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
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  /36

  $729,000

  • 3 Beds
  • 2 Baths
  • 2,556 Sq Ft

  580 Oak Summit Rd, Millbrook, NY 12545

  Charming country Cape Cod style home located minutes from the Village of Millbrook. This home offers an open floor plan with wood flooring, custom built kitchen cabinets, granite countertops, and stainless steel appliances. Dining room has slider to deck. Primary bedroom on first floor with full bath, including washer & dryer. Two large bedrooms are located on the second floor with a second full

  George Whalen III George T Whalen Real Estate

  580 Oak Summit Rd, Millbrook, NY 12545
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  $499,000

  $51K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,738 Sq Ft

  8 Trillium Rd, Pleasant Valley, NY 12569

  Welcome to this amazing weekend retreat or year-round sanctuary, privately set on 4.71 beautiful acres with a peaceful babbling brook. Surrounded by nature’s beauty, this special property offers the perfect blend of privacy, comfort, and tranquility. Step inside to a dramatic living room featuring a vaulted ceiling, a wall of glass with southern exposure, and an abundance of natural light. The

  Blake Michaud BHHS Hudson Valley Properties

  8 Trillium Rd, Pleasant Valley, NY 12569
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  $1,195,000

  $180K PRICE DROP

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

  101 Drake Rd, Pleasant Valley, NY 12569

  Historic Barn Conversion Meets Modern Luxury in the Hudson Valley Tucked away along a quiet country road in Pleasant Valley, this extraordinary estate offers a rare opportunity to own a meticulously restored 19th-century barn conversion that seamlessly blends historic character with modern luxury. Originally two separate barns, the property has been thoughtfully reimagined into a one-of-a-kind

  Jake Garay Serhant LLC

  101 Drake Rd, Pleasant Valley, NY 12569
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  $1,250,000

  $250K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,068 Sq Ft

  3311 Franklin Ave, Millbrook, NY 12545

  Don't miss this exceptional value in the heart of the Village of Millbrook: a beautifully maintained and thoughtfully updated 3-bedroom, 2-bath home (2,132 sq ft) complemented by a detached 1,750 sq ft two-car garage with an approximately 1,000 sq ft, 1-bedroom, 1-bath guest apartment above, currently generating rental income that pays for the taxes and maintenance for the entire property! Set on

  Ann Stettner Neil Charles Real Estate, LLC

  3311 Franklin Ave, Millbrook, NY 12545
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  /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
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  /2

  $325,000

  • Land
  • 12.8 Acres
  • $25,391 per Acre

  0 Deer Pond Rd Unit KEY958812, Union Vale, NY 12585

  Ideal 12+ acre home site, near the iconic Millbrook Village. This level fertile land features an existing pond and privacy being at the end of a cul-de-sac. This property is Board of Health approved for a four bedroom home (no filled required). Create your own country farm estate. Make an inspection visit today!

  Robert D Ferris R. Ferris Real Estate, LLC

  0 Deer Pond Rd Unit KEY958812, Union Vale, NY 12585
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  $729,000

  • 3 Beds
  • 1 Bath
  • 1,196 Sq Ft

  676-678 Oak Summit Rd, Millbrook, NY 12545

  Your dream awaits. Escape to this private retreat sited on 1.5 acres on a quiet country road minutes to the Village of Millbrook. This property offers endless possibilities. If you are a car enthusiast searching for an oversized garage with space to store 8+ cars, this is the property for you. There is even a loft-type office space with shelving to store parts and supplies. What a fantastic space

  Lori Rheingold

  676-678 Oak Summit Rd, Millbrook, NY 12545
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  /23

  $799,000

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,166 Sq Ft

  991 Freedom Rd, Pleasant Valley, NY 12569

  TO BE BUILT – The Vanderbilt Model Colonial on Over 3 Acres!This stunning 4-bedroom, 2.5-bath colonial offers the perfect blend of elegance and functionality. The thoughtfully designed main level features a formal living room and dining room, a spacious family room that showcases a gas fireplace and a wall of windows, seamlessly opening to the kitchen with quartz counters, a center island,

  John Gabriel Jr KW MidHudson

  991 Freedom Rd, Pleasant Valley, NY 12569
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  $374,900

  • 3 Beds
  • 2 Baths
  • 4,072 Sq Ft

  646 Oak Summit Rd, Millbrook, NY 12545

  Discover a unique and rare opportunity in this sprawling ranch-style 2-family home with generous space, flexible layout, and charming character— ready for your renovations and visions. Set on a picturesque 1.7-acre corner lot with an expansive yard, gazebo, shed, mature landscaping, the potential of this home welcomes a serene Hudson Valley lifestyle.The upper unit features over 2,000 sq. ft.

  LISA WOHLMUTH KW MidHudson

  646 Oak Summit Rd, Millbrook, NY 12545
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  /16

  $899,000

  • Land
  • 49.36 Acres
  • $18,213 per Acre

  0 Mallory Rd Unit KEY1016545, Union Vale, NY 12585

  Nearly 50 acres of enchanted woodland in the heart of Clove Valley, just minutes from the Village of Millbrook and within the Millbrook Central School District. Meandering trails wind through mature forest, past centuries-old stone walls and a picturesque pond, opening to sweeping countryside and distant Catskill views. A place of extraordinary beauty and complete privacy, where every season

  DOMINIQUE SHUMINOV William Pitt Sothebys Int Rlty

  0 Mallory Rd Unit KEY1016545, Union Vale, NY 12585
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  $695,000

  $100K PRICE DROP

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

  41 Meddaugh Rd, Pleasant Valley, NY 12569

  Welcome to 41 Meddaugh Road, a beautifully transformed 4 bedroom, 2.5 bathroom contemporary home with Hudson Valley historic farmhouse charm. Setback from the road, this turnkey home is sited on 1.84 acres and has undergone an extensive ground-up renovation. This property was previously under contract. The buyer was unable to close due to a contingency on their own home sale -- not any issue with

  Kyle Irwin Corcoran Country Living

  41 Meddaugh Rd, Pleasant Valley, NY 12569
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  $1,250,000

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,196 Sq Ft

  43 Maple Hill Dr, Millbrook, NY 12545

  New home under construction featuring a primary bedroom on the first level, high-end finishes, and exceptional attention to detail throughout. A two-story foyer with arched entry welcomes you to the formal living room, dining room, and the seamlessly connected kitchen and family room. Beautiful white oak flooring spans the entire first level, and the thoughtfully designed layout provides the

  TINA TOWNSEND BHHS Hudson Valley Properties

  43 Maple Hill Dr, Millbrook, NY 12545
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  $1,100,000

  $50K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 4,300 Sq Ft

  129 Clinton Corners Rd, Salt Point, NY 12578

  Set behind a sweeping driveway canopied by pear trees in bloom, this extraordinary post-and-beam contemporary is a study in what privacy truly looks like — 18.5 acres of curated landscape, forest trails, and open sky, ten minutes from the Taconic State Parkway. The architecture announces itself immediately: soaring 25-foot cathedral ceilings, a commanding central stone fireplace, and grand

  Ryan Arket Compass Greater NY, LLC

  129 Clinton Corners Rd, Salt Point, NY 12578
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  $1,495,000

  • 4 Beds
  • 3 Baths
  • 3,228 Sq Ft

  508 Woodstock Rd, Millbrook, NY 12545

  Set along a country road just beyond the Village of Millbrook, this cedar-sided traditional overlooks a serene, spring-fed pond and unfolds across 23 acres of rolling fields, mature trees, and thoughtfully kept grounds. The setting feels both expansive and private, with long views and a true sense of escape. The 3,200+ square foot home offers a spacious and flexible layout, with four bedrooms,

  OLIVER BROWN Houlihan Lawrence Inc.

  508 Woodstock Rd, Millbrook, NY 12545
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  $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
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  /35

  $599,000

  $26K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,480 Sq Ft

  50 Horseshoe Rd, Millbrook, NY 12545

  Welcome to this Contemporary Raised Ranch set on 1.52 acres in the Millbrook area, just minutes to the Village. Offering 2,480 finished square feet, the home has been thoughtfully updated to combine modern finishes with a practical, well-designed layout that flows with ease. The main level features a bright, inviting living area enhanced by a fresh coat of paint throughout, an updated kitchen

  STEVEN WROBEL JR. Serhant LLC

  50 Horseshoe Rd, Millbrook, NY 12545

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