Dutchess, NY Homes

• 

  

  

  /10

  $359,000

  • 3 Beds
  • 1.5 Baths
  • 1,628 Sq Ft

  39 Maple Ln, Dover Plains, NY 12522

  Deal Fell Through back on the MarketFor the first time this well constructed 3-bedroom, 1.5 bath home on a huge level lot is being offered to settle the Estate. there are no photos online until the home is emptied out. Each room is well proportioned, ample closets, the ceiling height is 7'6", the home is dated, the carpets are worn and need to be replaced. Under the carpet are hardwood

  

  Larry Havens

  Havens Real Estate

  (845) 506-8855

  39 Maple Ln, Dover Plains, NY 12522
• 

  

  

  /37

  $3,200 per month

  • 3 Beds
  • 2 Baths
  • 1,674 Sq Ft
  • House for Rent

  286 Cricket Hill Rd, Dover Plains, NY 12522

  Discover the perfect blend of comfort and countryside charm in this delightful home nestled in the heart of Dover Plains. Set on a beautifully maintained, expansive yard, this property offers ample space for relaxation and outdoor activities. The house features three well-appointed bedrooms and two full bathrooms, providing ample space for families or those seeking extra room. Enjoy summer

  Uzziel Abrigo eXp Realty

  286 Cricket Hill Rd, Dover Plains, NY 12522
• 

  $450,000 Sold Aug 11, 2025

  • 2,108 Sq Ft
  • $213/SF
  • 34 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1989

  25 White Farm Rd, Wingdale, NY 12594

  Beautifully Updated Raised Ranch in Country Mill EstatesThis move-in ready home offers the perfect blend of comfort, charm, and convenience. Nestled in the serene neighborhood of Country Mill Estates, the property features a spacious front and back yard with mature shade trees and well-maintained flower beds, creating a welcoming outdoor space.Inside, you'll find a bright and open

  Jonathan Scarinzi Elyse Harney Real Estate

  25 White Farm Rd, Wingdale, NY 12594
• 

  Est $467,341 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,101 Sq Ft

  25 Temby Dr, Dover Plains, NY 12522

  25 Temby Dr, Dover Plains, NY 12522
• 

  

  

  /41

  $435,000 Pending

  • 3 Beds
  • 3 Baths
  • 1,794 Sq Ft

  27 Cavelo Dr, Wingdale, NY 12594

  Tucked away at the end of a quiet cul-de-sac on 1.79 picturesque acres, this beautifully maintained 3-bedroom, 3-bath home offers the perfect blend of privacy, space, and convenience. Step inside and head upstairs to a sun-filled, open-concept living space where the hardwood floors flow through a spacious Living Room and adjoining Dining Room. Large windows bathe the space in natural light, while

  

  Shannon Tully

  McGrath Realty Inc

  (845) 328-6912

  27 Cavelo Dr, Wingdale, NY 12594
• 

  

  /7

  $2,150 per month

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft
  • Apartment for Rent

  85 Hutchinson Ave Unit c, Wingdale, NY 12594

  Come view this beautifully renovated 2 bedroom 1 bathroom apartment with plenty of storage. This rental includes a private deck and assigned parking for up to two cars; and is close to everything, including train, shops, restaurants, outdoor attractions like Thunder Ridge Mountain, and schools. Heat and hot water included in the monthly rent. -

  David Cebel Iconik Residential LLC

  85 Hutchinson Ave Unit c, Wingdale, NY 12594
• 

  $785,000 Sold Aug 11, 2025

  • 1,952 Sq Ft
  • $402/SF
  • 19 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1998

  6843 Route 55, Wingdale, NY 12594

  Serenity Hill is a hidden oasis. A long driveway winds through a broad meadow and then across a bridge over a rushing woodland stream. The homesite is elevated-a beautiful plateau that faces west towards the foothills of The Taconic Mountains. The classic farmhouse is set amid acres of rolling lawn. A rocking chair porch surrounds the house on three sides. The interior is designed as open plan

  David Turner Compass Greater NY, LLC

  6843 Route 55, Wingdale, NY 12594
• 

  Est $404,778 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft

  1512 Route 343, Dover Plains, NY 12522

  1512 Route 343, Dover Plains, NY 12522
• 

  

  /23

  $469,000

  • 3 Beds
  • 2 Baths
  • 1,523 Sq Ft

  105 S Nellie Hill Rd, Dover Plains, NY 12522

  Circa 1952 - A delightful home that has been totally transformed into a casually elegant masterpiece.The roof was replaced in 2012. The siding was replaced in 2022. The interior of the home was totally redone in 2024.The floors are exquisite, the tiled baths are luxurious, the kitchen is a dream (quartz counter and back splash), and the flow is welcoming. The sun filled deck supports

  

  Larry Havens

  Havens Real Estate

  (845) 478-1624

  105 S Nellie Hill Rd, Dover Plains, NY 12522
• 

  

  /24

  $3,800 per month

  • 3 Beds
  • 2.5 Baths
  • 2,229 Sq Ft
  • Apartment for Rent

  921 W Dover Rd, Pawling, NY 12564

  ALL INCLUSIVE RENTAL! All utilities and services are included. This 3-bedroom, 2.5 bathroom no-step main floor apartment is now available. Consisting of the whole main level of a beautiful, custom quality built ranch home and nestled on 8+ private acres, this apartment is 2200+ square feet! This modern house boasts a beautiful and open floor plan. A chef's kitchen has extensive granite counters,

  Joyce Brennan-Zolnik BHHS Hudson Valley Properties

  921 W Dover Rd, Pawling, NY 12564
• 

  $45,000 Sold Aug 08, 2025

  • Land
  • 5.00 Acres
  • $9,000 per Acre

  • 37 Days On Market

  0 Cooperstown Rd Unit KEY854621, Dover, NY 12522

  5 Acres of Serenity on Cooperstown Rd, Dover Plains, NY. Looking for the perfect escape to nature? This 5-acre wooded lot on Cooperstown Rd in Dover Plains, NY is the ideal place to build your tiny home getaway or create your own personal hunting paradise. The land features a bubbling brook at the front, providing soothing sounds and a serene atmosphere—just imagine waking up to that every

  Curtis Darragh Legacy Land & Homes LLC

  0 Cooperstown Rd Unit KEY854621, Dover, NY 12522
• 

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 924 Sq Ft

  37 Mallard Way, Dover Plains, NY 12522

  37 Mallard Way, Dover Plains, NY 12522
• 

  

  /20

  $379,900

  • 3 Beds
  • 1.5 Baths
  • 1,520 Sq Ft

  10 Raymond Ave, Dover Plains, NY 12522

  Tucked away at the end of a quiet cul-de-sac, this beautifully maintained country home is on the market for the first time since 1995. The home showcases gleaming hardwood floors throughout, with tasteful tile in the bathrooms. Each room has its own distinct charm and character.The main level features a sun-filled eat-in kitchen that flows seamlessly into a spacious great room with vaulted

  

  Larry Havens

  Havens Real Estate

  (845) 493-2818

  10 Raymond Ave, Dover Plains, NY 12522
• 

  $315,000 Sold Aug 06, 2025

  • 1,135 Sq Ft
  • $278/SF
  • 31 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1970

  30 Lake Ellis Rd, Wingdale, NY 12594

  This bright and inviting 3-bedroom, 1.5-bath ranch is the kind of home that’s becoming harder to find—a well-maintained, move-in ready property with a smart layout, modern touches, and room to grow.Set just 7 minutes from the train and town center, this peaceful retreat offers the best of both worlds: quiet country charm with quick access to shopping, dining, and transit. You’re only 15

  Alex Mashkin Keller Williams Realty Partner

  30 Lake Ellis Rd, Wingdale, NY 12594
• 

  Not Listed For Sale

  139 Sheldon Rd, Wingdale, NY 12594

  139 Sheldon Rd, Wingdale, NY 12594
• 

  

  /50

  $445,000

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

  26 Nicole Ln, Wingdale, NY 12594

  Charming and fully remodeled, this 3-bedroom, 2-bath raised ranch in the desirable Woodwinds subdivision offers modern comfort and timeless appeal. With a fully fenced yard, spacious deck, and detached oversized 2-car garage, this home is move-in ready and designed for easy living. Recent updates include a new roof (2022), new furnace (2024), new water softener system (2023), refreshed central

  Andrea Rudkowski Closer Real Estate

  26 Nicole Ln, Wingdale, NY 12594
• 

  $465,000 Sold Aug 01, 2025

  • 1,750 Sq Ft
  • $266/SF
  • 19 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2021

  268 Lime Kiln Rd, Dover Plains, NY 12522

  Welcome to this beautifully maintained, newly built raised ranch sitting on one flat acre in a quiet country setting! Enjoy an open kitchen, dining and living room area perfect for entertaining with 2 full bathrooms upstairs. Downstairs is a finished bonus room with a half bath and a Lopi pellet stove. The laundry room is kept in closed closet doors next to the 2 car garage door with beautiful

  Jacqueline Redahan Century 21 Alliance Realty Grp

  268 Lime Kiln Rd, Dover Plains, NY 12522
• 

  Est $528,193 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,943 Sq Ft

  6 Jordyn Ln, Dover Plains, NY 12522

  6 Jordyn Ln, Dover Plains, NY 12522
• 

  

  /44

  $575,000

  • 3 Beds
  • 3 Baths
  • 2,058 Sq Ft

  283 & 279 Johnson Rd, Wingdale, NY 12594

  Beautiful house, quiet setting, level park-like property with fully fenced back yard! In 2002, a huge 2nd floor addition and a full renovation of the main floor created an amazing home! The homeowners are INCLUDING 279 Johnson Rd, an adjoining lot with 2 Garages, 40x28 w/heat & 1/2 bath. 2nd garage is 24x24 - More info further down... Total acreage of lots is 1.13 acres. Let's go back to the

  Lisa Liffland McGrath Realty Inc

  283 & 279 Johnson Rd, Wingdale, NY 12594
• 

  $550,000 Sold Jul 29, 2025

  • 1,960 Sq Ft
  • $281/SF
  • 86 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2019

  46 Peaceable Way, Dover Plains, NY 12522

  Welcome to this beautiful, move-in ready one-level Ranch Home with an open floor plan! At just 6 years young and fully handicapped accessible, it’s located on a quiet cul-de-sac with breathtaking mountain views. The spacious, unfinished basement was built with "Superior Walls" and offers endless possibilities for expansion. The primary bedroom suite comfortably accommodates a king-size bed and

  Laura Fasciglione Keller Williams Realty Partner

  46 Peaceable Way, Dover Plains, NY 12522
• 

  Not Listed For Sale

  0 Drovers Ln Unit KEYM413718, Dover, NY 12522

  0 Drovers Ln Unit KEYM413718, Dover, NY 12522
• 

  

  /47

  $649,900

  • 3 Beds
  • 2 Baths
  • 2,107 Sq Ft

  28 Gobblers Knob Rd, Pawling, NY 12564

  Welcome to 28 Gobblers Knob Road – A Hudson Valley Retreat! Nestled in the heart of the rolling hills of the stunning Hudson Valley, this beautiful 3-bedroom, 2-bathroom home sits on over 20 acres, offering peace, privacy, and natural beauty in every direction. Just over 3 miles from the Metro-North line to Manhattan, you can enjoy the quiet of a country escape without sacrificing

  Mark Snyder eXp Realty

  28 Gobblers Knob Rd, Pawling, NY 12564
• 

  $380,000 Sold Jul 24, 2025

  • 1,588 Sq Ft
  • $239/SF
  • 31 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1960

  37 Rural Ave, Wingdale, NY 12594

  Located in the hamlet of Wingdale, this 3 bedroom, 2 bath home sits just minutes from the Metro-North station, nearby hiking trails and the shops and cafe's of Pawling. a spacious living room with hardwood floors opens directly into the kitchen, which boasts stone countertops, a subway-tile backsplash, a stainless-steel undermount sink and a bar-height counter for casual meals. The adjoining

  Jill Rose Houlihan Lawrence Inc.

  37 Rural Ave, Wingdale, NY 12594
• 

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft

  10 Vincent Rd, Dover Plains, NY 12522

  10 Vincent Rd, Dover Plains, NY 12522
• 

  

  /3

  $649,000

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

  149 Johnson Rd, Wingdale, NY 12594

  New construction home to be built ! This raised ranch home features 3 bedrooms and 3 full bathrooms and 2 car garage. The open floor plan connects the kitchen, dining room and living room. The primary bedroom with ensuite bathroom features a spa like walk in shower. The plans are approved and ready to build, don't miss the opportunity to customize this home

  Bliss Voutsinas

  149 Johnson Rd, Wingdale, NY 12594
• 

  $410,000 Sold Jul 24, 2025

  • 1,400 Sq Ft
  • $293/SF
  • 34 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1960

  11 Birch Terrace, Pawling, NY 12564

  Welcome to Pawling Lake Estates - a private lake community about 10 minutes outside the Village of Pawling. This adorable cozy Cape is located on a dead-end road. Has 2 bedrooms but can easily live like a 3-bedroom home. Main level has eat in kitchen with breakfast nook, cozy living room with big bay window. 2 Bedrooms and a main bath. Doors in kitchen that lead out to a nice size deck

  Teddie Leonaggeo McGrath Realty Inc

  11 Birch Terrace, Pawling, NY 12564
• 

  Est $454,853 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,770 Sq Ft

  31 White Oak Cir, Wingdale, NY 12594

  31 White Oak Cir, Wingdale, NY 12594
• 

  

  /33

  $599,000

  • 4 Beds
  • 4.5 Baths
  • 3,088 Sq Ft

  763 Old State Route 22, Dover Plains, NY 12522

  For those seeking the ultimate in charm and comfort, The Preston House, one of the accommodations at the renowned Old Drovers Inn Bed and Breakfast, is now available for sale. This beautifully renovated 3,088 SF colonial blends old-world elegance with modern conveniences, offering a truly unique living experience. Steeped in history, the home features period architectural details throughout,

  Brian McGrath McGrath Realty Inc

  763 Old State Route 22, Dover Plains, NY 12522
• 

  $105,000 Sold Jul 19, 2025

  • 980 Sq Ft
  • $107/SF
  • 106 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1978

  70 Sasso Ln, Wingdale, NY 12594

  Turn key Living in a Fully Renovated Home!Step into this beautifully renovated home, where comfort meets convenience in a move-in-ready space! Every detail has been upgraded, from the brand-new flooring to the newer appliances, ensuring modern functionality throughout.The spacious living room invites you in with a cozy wood-burning fireplace, perfect for chilly evenings, while the

  Tela Cook McGrath Realty Inc

  70 Sasso Ln, Wingdale, NY 12594
• 

  Est $499,479 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,990 Sq Ft

  97 N Farm Dr, Dover Plains, NY 12522

  97 N Farm Dr, Dover Plains, NY 12522
• 

  

  /39

  $449,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,610 Sq Ft

  22 Riverdale Dr, Wingdale, NY 12594

  Lovely raised ranch home. Large flat backyard for entertaining with a deck and an inground pool. Three bedroom, 1.5 bath. Living room has a lovely fireplace.Finished basement with pellet stove, family room and bar and laundry. Central A/C. Town water and sewer. Separate large shed for workshop/storage. NY Star savings $572.29 not included in taxes. A/O 6/18/25

  Dianna Ferrieri My Seasons Realty LLC

  22 Riverdale Dr, Wingdale, NY 12594
• 

  $430,000 Sold Jul 18, 2025

  • 1,844 Sq Ft
  • $233/SF
  • 36 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1961

  41 Hillside Ave, Wingdale, NY 12594

  LET'S GO! Welcome to 41 Hillside Ave, a lovely 3 bedroom ranch styled home located directly in the middle of the charming Villages of Dover Plains and Pawling, in the quaint hamlet of Wingdale, with the conveniency of the Metro-North Train Station only a minute or two south on Route 22, as well as Boyce Park, the Dover Library, and Wingdale Elementary School literally a stone's throw away,

  Reid McGrath McGrath Realty Inc

  41 Hillside Ave, Wingdale, NY 12594
• 

  Est $538,382 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,670 Sq Ft

  31 Lime Kiln Rd, Dover Plains, NY 12522

  31 Lime Kiln Rd, Dover Plains, NY 12522
• 

  

  /37

  $465,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,664 Sq Ft

  18 Johnson Rd, Wingdale, NY 12594

  Welcome to this beautifully maintained raised ranch nestled on a peaceful, neighborly street. This inviting home features an updated kitchen with modern cabinetry, countertops, and stainless steel appliances—perfect for cooking and entertaining. The bathrooms have been tastefully renovated with contemporary fixtures and stylish finishes, offering both comfort and functionality.Enjoy the spacious,

  Karen Gundelach Keller Williams Realty Partner

  18 Johnson Rd, Wingdale, NY 12594
• 

  $345,000 Sold Jul 09, 2025

  • 900 Sq Ft
  • $383/SF
  • 26 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1990

  88 Lakeview Dr, Pawling, NY 12564

  Charming Cottage in Private Community of Pawling Lake Estates. Adjacent to the Appalachian Trail and the Great Swamp of Putnam and Dutchess County, sitting atop the West Mountain State Park you will find our Community, a Hidden Gem. Privacy, Peace and Tranquility abound in this Natural Setting. This Home has been lovingly cared for and updated with Replacement Windows, Vinyl Siding, Gutter Guards

  Martha Woodhouse Howard Hanna Rand Realty

  88 Lakeview Dr, Pawling, NY 12564
• 

  Est $518,584 Not Listed For Sale

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

  11 Sand Hill Rd, Dover Plains, NY 12522

  11 Sand Hill Rd, Dover Plains, NY 12522
• 

  

  /25

  $475,000 Pending

  • 3 Beds
  • 3 Baths
  • 2,508 Sq Ft

  1 Craig Ln, Dover Plains, NY 12522

  Great Mother-daughter or income producing apartment in this very well maintained home in Dover. Upstairs has 3 bedrooms and 2 full bathrooms and a separate laundry room. The living room features hardwood flooring and an energy efficient heating and cooling mini split. Downstairs you’ll find a complete one bedroom, 1 bathroom apartment, perfect to offset the mortgage or produce income. New boiler

  Richard Brenner Rich Brenner Realty, LLC

  1 Craig Ln, Dover Plains, NY 12522
• 

  $519,000 Sold Jul 08, 2025

  • 1,540 Sq Ft
  • $337/SF
  • 76 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1962

  476 Chestnut Ridge Rd, Dover Plains, NY 12522

  Escape to the serenity of the countryside with this beautifully updated California-style ranch, set on a private and picturesque 2.2-acre property. Designed for both comfort and style, this 3 bedroom home features a 32x16 in-ground pool and ample space for horses, with open fields extending beyond the backyard. Inside, gleaming hardwood floors flow through most of the living space, complementing

  Emelisa Mendoza RE/MAX Town & Country

  476 Chestnut Ridge Rd, Dover Plains, NY 12522
• 

  Est $399,316 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,969 Sq Ft

  63 Lime Kiln Rd, Dover Plains, NY 12522

  63 Lime Kiln Rd, Dover Plains, NY 12522
• 

  

  /41

  $825,000

  • 4 Beds
  • 4.5 Baths
  • 2,234 Sq Ft

  360 Old State Route 22, Dover Plains, NY 12522

  A rare offering in today’s market - gorgeous River Front Home with calming water views and fishing every day right in your own back yard. Renovated and updated 3 bedroom home with a one bedroom pool house that doubles as a guest cottage. All the amenities you would expect in the best resort style property. Open concept Living and Dining area with 2 sets of French doors opening to an expansive

  Judy Albert BHHS Hudson Valley Properties

  360 Old State Route 22, Dover Plains, NY 12522

Showing Results 1 - 40, Page 1 of 18