Dutchess, NY Homes

• 

  

  

  /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

  

  Philip Bisesto

  HomeSmart Homes & Estates

  (845) 681-2247

  89 Birch Dr, Pleasant Valley, NY 12569
• 

  

  

  /31

  $1,960 - $3,095 per month

  Brookside Meadows Luxury Rental Community

  1 - 3 Beds

  10100 Brookside Rd, Pleasant Valley, NY 12569

  Welcome to Brookside Meadows, where timeless elegance meets modern convenience in the heart of Pleasant Valley, NY. This sought-after luxury gated rental community offers a serene, park-like setting with beautifully landscaped grounds, walking trails, and scenic views just minutes from the vibrant Hudson Valley lifestyle.Each residence is thoughtfully designed with upscale finishes,

  10100 Brookside Rd, Pleasant Valley, NY 12569
• 

  $390,000 Sold Aug 29, 2025

  • 2,240 Sq Ft
  • $174/SF
  • 205 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1910

  32 Halcyon Rd, Millbrook, NY 12545

  Welcome to this beautifully situated home in the heart of Millbrook, a tranquil and highly desirable location just under a mile from the village center. Offering the perfect blend of privacy and convenience, this home is within easy reach of the village’s renowned restaurants, shops, galleries, parks, and more. Set back off a quiet road, it provides a peaceful retreat while still being close to

  Jo-Ann Campagiorni

  32 Halcyon Rd, Millbrook, NY 12545
• 

  Est $620,404 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,348 Sq Ft

  664 Plass Rd, Pleasant Valley, NY 12569

  664 Plass Rd, Pleasant Valley, NY 12569
• 

  

  

  /22

  $490,000

  • 4 Beds
  • 2 Baths
  • 1,700 Sq Ft

  166 Hibernia Rd, Salt Point, NY 12578

  Nestled In The Hamlet Of Salt Point NY, In The Town Of Pleasant Valley Is This Remodeled Home Offering Four Bedrooms And Two Baths. The Front Exterior Has Dual Entry Access To Various Locations Within The Home Which Displays A Combination Of Engineered Wood And Ceramic Tiled Floors. Each Room Has Been Thoughtfully Updated. Here You Will Find The Kitchen With State Of The Arts Stainless Steel

  

  Joyce Stanton

  Century 21 Hudson Valley Rlty.

  (845) 599-8106

  166 Hibernia Rd, Salt Point, NY 12578
• 

  

  /41

  $6,000 per month

  • 3 Beds
  • 2.5 Baths
  • 1,709 Sq Ft
  • House for Rent

  272 Drake Rd, Pleasant Valley, NY 12569

  Private Hudson Valley SanctuaryTucked away on over 24 acres of wooded beauty with tranquil water views and a private pond, this one-of-a-kind 3-bedroom, 2.5-bath contemporary ranch invites you to slow down, breathe deeply, and feel at home.Step inside to an open, sun-drenched layout where maple hardwood floors glow beneath exposed wood beams and stone fireplaces warm both the living room

  Kara Winters A&K ELITE REAL ESTATE SERVICES

  272 Drake Rd, Pleasant Valley, NY 12569
• 

  $505,000 Sold Aug 28, 2025

  • 1,800 Sq Ft
  • $281/SF
  • 49 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1985

  186 Oswego Rd, Pleasant Valley, NY 12569

  Tastefully updated and impeccably maintained 3 bedroom, 2 bath ranch situated on beautiful one acre parcel. Custom kitchen w/designer cabinetry, stainless appliances, quartz counters, breakfast bar & pantry. Spacious living room flows to dining room, which provides easy access to composite rear deck complete with pergola. Master bedroom with ensuite bathroom. Two additional bedrooms, one with

  Dan Axtmann BHHS Hudson Valley Properties

  186 Oswego Rd, Pleasant Valley, NY 12569
• 

  Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 980 Sq Ft

  62 Elm Ln, Pleasant Valley, NY 12569

  62 Elm Ln, 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
• 

  /2

  Call for Price

  14 Arbor Hill Drive

  2 Beds

  12 Arbor Hill Dr, Pleasant Valley, NY 12569

  Residential

  12 Arbor Hill Dr, Pleasant Valley, NY 12569
• 

  $525,000 Sold Aug 28, 2025

  • 2,048 Sq Ft
  • $256/SF
  • 118 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1910

  53 Jameson Hill Rd, Clinton Corners, NY 12514

  Accepted Offer 6/7 Welcome to the Eagles Nest, a tranquil retreat perched on one elevated high and dry acre surrounded by flowering trees, low maintenance lawn and lush evergreens in the Millbrook School District.1.15hr to NYC, easy commute, 1 mile1 minute to the Taconic (both N&S) close to Dutchess County culinary cultural historical, recreational amenities and experiences.This

  Latanya Frazier Oxford Property Group USA

  53 Jameson Hill Rd, Clinton Corners, NY 12514
• 

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft

  65 Elm Ln, Pleasant Valley, NY 12569

  65 Elm Ln, 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
• 

  

  /23

  $7,000 per month

  • 3 Beds
  • 2 Baths
  • House for Rent

  2415 Salt Point Turnpike, Clinton Corners, NY 12514

  Enjoy the perfect Hudson Valley getaway in a historic country cottage surrounded by nature and within walking distance to a charming village cafe and wine store. This newly renovated and air conditioned 3 bedroom Salt Box home includes a spacious primary suite with king size bed, lounge area and new ensuite bathroom. 2 smaller bedrooms - one cosy double and 1 single - share a larger

  Joshua Schwadron CASABODE GROUP LLC

  2415 Salt Point Turnpike, Clinton Corners, NY 12514
• 

  $128,000 Sold Aug 26, 2025

  • 864 Sq Ft
  • $148/SF
  • 28 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1930

  25 Pine Hill Rd, Pleasant Valley, NY 12569

  Are you looking for a great summer project ? - look no further! Bring your hardhat, hammer and a few tools to get started on renovations in this ranch style home. The home is positioned on 1.1 acre of garden property and is set back off the road. The spacious front porch greets you and invites you into the living room. It highlights hardwood floors and a wood burning fireplace. The kitchen opens

  Ann Scarano Realty Center Hudson Valley

  25 Pine Hill Rd, Pleasant Valley, NY 12569
• 

  Est $487,856 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,408 Sq Ft

  1847 Route 44, Pleasant Valley, NY 12569

  1847 Route 44, Pleasant Valley, NY 12569
• 

  

  /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
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  /2

  $2,200 - $2,500 per month

  Apartment for Rent

  2 Beds

  7 Oswego Rd, Pleasant Valley, NY 12569

  Rental is a two bedroom newly remodeled cottage adjacent to the main apartment building.

  7 Oswego Rd, Pleasant Valley, NY 12569
• 

  $418,000 Sold Aug 26, 2025

  • 1,425 Sq Ft
  • $293/SF
  • 32 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1960

  3206 Sharon Turnpike, Millbrook, NY 12545

  Welcome to this inviting 2-bedroom, 1.5-bath ranch nestled on 1.70 serene and private acres just minutes from the Village of Millbrook. This home blends classic charm with thoughtful updates, offering comfort and functionality in a beautiful country setting. Step inside to discover hardwood floors and a spacious living room warmed by a cozy pellet stove—perfect for chilly Hudson Valley winters.

  Karen Volino Houlihan Lawrence Inc.

  3206 Sharon Turnpike, Millbrook, NY 12545
• 

  Not Listed For Sale

  0 Verbank Rd, Millbrook, NY 12545

  0 Verbank Rd, Millbrook, NY 12545
• 

  

  /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
• 

  

  /20

  $2,500 per month

  • 2 Beds
  • 1 Bath
  • 1,800 Sq Ft
  • Apartment for Rent

  2297 Route 44, Pleasant Valley, NY 12569

  Available for rent is this spacious, natural light filled, updated, immaculate, 2+ bedroom, townhouse style apartment located in a quiet area, yet close to all shopping, schools, transportation and all the area offers. Walk into the large open floor plan consisting of spacious living room, eat-in-kitchen, a large bedroom and bathroom complete the first floor. Charming french door leads to the

  Gina Antonucci Easy Lifestyle Real Estate

  2297 Route 44, Pleasant Valley, NY 12569
• 

  $2,375,000 Sold Aug 22, 2025

  • 9,150 Sq Ft
  • $260/SF
  • 93 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2005

  216 Barmore Rd, Lagrangeville, NY 12540

  This wonderful country retreat is a balance of modern design, a wellness mindset, and timeless craftsmanship with every attention to detail. Milling trees from the property to construct the barn using the masterful post-and-beam construction method, creating intricate joints without nails.The current owner has meticulously updated the home in Union Vale which offers notably lower school

  Marc Maclean William Pitt Sothebys Int Rlty

  216 Barmore Rd, Lagrangeville, NY 12540
• 

  Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 2,584 Sq Ft

  29 Merrit Ave, Millbrook, NY 12545

  29 Merrit Ave, Millbrook, NY 12545
• 

  

  /44

  $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
• 

  

  /20

  $1,999 - $2,404 per month

  Village Park Apartments

  1 - 2 Beds

  5 Park Dr, Pleasant Valley, NY 12569

  Enjoy all the pleasures of country living by renting at Village Park Apartments. We are located in the heart of the beautiful, historic land of Pleasant Valley, NY, only minutes away from all the conveniences of village life. With our scenic atmosphere and quick access to New York City or the beautiful Queen City of the Hudson River Poughkeepsie, you have the best of both worlds here at Village

  5 Park Dr, Pleasant Valley, NY 12569
• 

  $45,000 Sold Aug 22, 2025

  • 980 Sq Ft
  • $46/SF
  • 99 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1979

  30 Elm Ln, Pleasant Valley, NY 12569

  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.

  Steven Collier BHHS Hudson Valley Properties

  30 Elm Ln, Pleasant Valley, NY 12569
• 

  /2

  Est $1,341,203 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 450 Sq Ft

  1612 Main St, Pleasant Valley, NY 12569

  1612 Main St, Pleasant Valley, NY 12569
• 

  

  /34

  $990,000

  • 4 Beds
  • 4 Baths
  • 3,506 Sq Ft

  121 Valley Farm Rd, Millbrook, NY 12545

  This unique timberframe home is welcoming, spacious, and awaiting your personal touch! Tucked back off the road on 7 private acres, this property has so many special features, including an outdoor, covered patio with kitchen, pizza oven and fireplace, a traditional red barn, and another large outbuilding with heat and electricity - the perfect place for your special hobby - whether it be cars,

  THERESA GILL Legacy Land & Homes LLC

  121 Valley Farm Rd, Millbrook, NY 12545
• 

  

  /4

  $2,445 per month

  • 2 Beds
  • 1.5 Baths
  • 1,300 Sq Ft
  • House for Rent

  28 Alden Place, Millbrook, NY 12545

  AVAILABLE AUGUST 15TH!!!MORE PICTURES COMING SOON, NEW FLOORING IS BEING INSTALLEDCharming 2 Bedroom + Office single-family home available right in the heart of Millbrook Village!Enjoy the comfort and privacy of your own standalone home-no shared walls, no noisy neighbors above or below. Features include:Spacious layout with 2 bedrooms plus a separate office/guest

  Kirk Rotger Millennium Realty Solutions

  28 Alden Place, Millbrook, NY 12545
• 

  $855,000 Sold Aug 21, 2025

  • 3,398 Sq Ft
  • $252/SF
  • 189 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1900

  147 Verbank Village Rd, Verbank, NY 12585

  This circa 1910, handsome Hudson Valley farmhouse on 19+ acres is a wonderful country retreat, perfect for entertaining family and friends. It boasts beautiful wood flooring, attractive high ceilings, and ample windows that provide an abundance of natural light and take full advantage of picturesque views of the outdoors. A fireplace adds winter warmth and the central air adds summer comfort.

  Susan Whalen George T Whalen Real Estate

  147 Verbank Village Rd, Verbank, NY 12585
• 

  Not Listed For Sale

  0 Milewood Rd Unit KEYH6305719, Washington, NY 12545

  0 Milewood Rd Unit KEYH6305719, Washington, NY 12545
• 

  

  /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
• 

  

  /17

  $1,850 per month

  • 1 Bed
  • 1 Bath
  • Condo for Rent

  152 Church St, Millbrook, NY 12545

  Yearly Rental. Enjoy living in the heart of the Village of Millbrook with easy access to restaurants, shops and more. This second floor one bedroom, one bath apartment is located above a restaurant. It was recently refreshed with new paint, refinished floors and a new stove. The living room/dining room is light filled and spacious with 8'7" high ceilings. The galley kitchen has a pass through to

  152 Church St, Millbrook, NY 12545
• 

  $1,350,000 Sold Aug 12, 2025

  • 2,348 Sq Ft
  • $575/SF
  • 22 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1955

  3254 Route 82, Verbank, NY 12585

  Introducing the Pond Ridge Compound, a Mid-Century gem on 18 private and idyllic acres with sweeping lawns and mountain views. The property features a pool, swimming pond, guest cottage, 2-stall barn and an oversized two-story heated garage. Built in 1955, the house maintains all of its original charm and mid-century aesthetic, yet updated with modern amenities like a large, over-producing solar

  BRETT SNIDER Rouse + Co Real Estate LLC

  3254 Route 82, Verbank, NY 12585
• 

  Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,212 Sq Ft

  323 Masten Rd Unit 325, Pleasant Valley, NY 12569

  323 Masten Rd Unit 325, Pleasant Valley, NY 12569
• 

  

  /37

  $725,000

  • 3 Beds
  • 4 Baths
  • 3,633 Sq Ft

  30 Eddy Rd, Verbank, NY 12585

  Welcome to 30 Eddy Road, a stunning contemporary residence nestled on a generous 1.17-acre lot in the serene Town of Union Vale. This meticulously maintained home boasts gleaming hardwood floors throughout, creating a warm and inviting atmosphere from the moment you step inside.The open-concept living and dining areas feature soaring ceilings accented by rustic wooden beams and expansive

  Robert Chiappone Century 21 Hire Realty

  30 Eddy Rd, Verbank, NY 12585
• 

  

  /35

  $7,000 per month

  • 3 Beds
  • 3 Baths
  • 1,842 Sq Ft
  • House for Rent

  441 Oak Summit Rd, Millbrook, NY 12545

  This completely reconstructed 2022 modern farmhouse is available for rent, offering over seven acres of lush forest and rolling meadows with unmatched privacy just five minutes from the vibrant main street of Millbrook. Designed in a stylish mid-century modern farmhouse style, every space has been thoughtfully reimagined to maximize light, views, and comfort. Large windows in every room frame the

  Heidi Maloney Four Seasons Sotheby's Int'l R

  441 Oak Summit Rd, Millbrook, NY 12545
• 

  $900,000 Sold Aug 07, 2025

  • 3,770 Sq Ft
  • $239/SF
  • 161 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2004

  422 Rossway Rd, Pleasant Valley, NY 12569

  Discover the elegance and charm of this stunning residence located in the Town of LaGrange, within the esteemed Arlington School District. Nestled on nearly 11 acres of land, this enchanting stone-clad and stucco ranch home offers a perfect blend of sophistication and comfort.As you approach the property, a wooded path leads you to a scenic setting enhanced by stacked stone walls and

  Kaye Saglibene

  422 Rossway Rd, Pleasant Valley, NY 12569
• 

  Est $767,293 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,920 Sq Ft

  938 Freedom Rd Unit 965, Pleasant Valley, NY 12569

  938 Freedom Rd Unit 965, Pleasant Valley, NY 12569

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