Homes in ZIP Code 12594

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  /29

  $599,900

  • 2 Beds
  • 2.5 Baths
  • 1,820 Sq Ft

  36 Byrds Hill Rd, Pawling, NY 12564

  The Perfect Weekend Escape or Full-Time Country Home, just 90 minutes from NYC. Set on a quiet, scenic road in the prestigious Quaker Hill area, you’re a short drive to the Village of Pawling with shopping, restaurants, highways, and Metro-North access. From the outside, it’s a classic farmhouse with rolling green acreage and space to breathe. Step inside, and you’re met with modern, yet cozy

  

  Colleen McGrath

  McGrath Realty Inc

  (845) 630-1049

  36 Byrds Hill Rd, Pawling, NY 12564
• 

  

  

  /19

  $2,000 per month

  • 2 Beds
  • 2 Baths
  • 1,296 Sq Ft
  • Apartment for Rent

  1531 Route 22 Unit E, Wingdale, NY 12594

  Welcome to this comfortable and conveniently located 2 bedroom Apartment w/both front & back entrances. Bright open concept one level living has an eat in kitchen w/tile floor & recessed lighting, large living room with coat closet, and an additional spacious back room which can be used for multiple uses (back room has a door out to back). Spacious bedroom with renovated full bath & large closet,

  Diana Cirocco Coldwell Banker Realty

  1531 Route 22 Unit E, Wingdale, NY 12594
• 

  $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
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  /62

  Est $876,664 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,496 Sq Ft

  158 Lake Ellis Rd, Wingdale, NY 12594

  158 Lake Ellis Rd, Wingdale, NY 12594
• 

  

  

  /41

  $435,000

  • 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
• 

  $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
• 

  Not Listed For Sale

  139 Sheldon Rd, Wingdale, NY 12594

  139 Sheldon Rd, Wingdale, NY 12594
• 

  

  /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
• 

  

  /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
• 

  $325,000 Sold Jun 30, 2025

  • 1,362 Sq Ft
  • $239/SF
  • 43 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1997

  26 Lilac Dr, Wingdale, NY 12594

  Charming 2-Bedroom, 1-Bathroom Raised Ranch with Bonus Office, pool & large Deck!Welcome to this cozy raised ranch, where comfort and flexibility meet! With 2 bedrooms that live like 3, plus an additional office space, this home offers plenty of room to spread out. Whether you need extra sleeping space, a home office, or a playroom, this home has you covered.The living area is

  Crystal Neceda Briante Realty Group, LLC

  26 Lilac Dr, Wingdale, NY 12594
• 

  Est $460,883 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
• 

  

  /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
• 

  $815,000 Sold Jun 26, 2025

  • 3,292 Sq Ft
  • $248/SF
  • 11 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1930

  50 N Chippawalla Rd, Wingdale, NY 12594

  Have you ever thought to yourself "Someday I'm going to have my own farm or a private retreat upstate..." Well, NOW is your opportunity to own your own PRIVATE 8 ACRE RETREAT in the highly desirable Mid-Hudson Valley! This complex has boundless possibilities including TWO living quarters: A Cape Cod Style Main Home featuring 2 large bedrooms, 2 baths, and a kitchen with so much natural light

  CHRISTOPHER FILANGERI BHHS Hudson Valley Properties

  50 N Chippawalla Rd, Wingdale, NY 12594
• 

  /2

  Est $654,034 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,446 Sq Ft

  9 Blueberry Dr, Wingdale, NY 12594

  9 Blueberry Dr, Wingdale, NY 12594
• 

  

  /24

  $450,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,108 Sq Ft

  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
• 

  $1,200,000 Sold Jun 10, 2025

  • 5,532 Sq Ft
  • $217/SF
  • 37 Days On Market

  • 6 Beds
  • 5 Baths
  • Built 2009

  206-208 Dog Tail Corners Rd, Wingdale, NY 12594

  Have you dreamed of owning an incredibly special and unique property? Well, dream no more, now is your chance! A winding driveway off of a small country road, brings you to a custom-built, private, 6-bedroom, 5-bath, light-filled contemporary home with a 2- bedroom guest house, on 7.2+ acres that enjoys 550 feet of frontage on the beautiful Tenmile River, as well as a pond, perfect for swimming,

  Ann Stettner Neil Charles Real Estate, LLC

  206-208 Dog Tail Corners Rd, Wingdale, NY 12594
• 

  /2

  Est $699,777 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,248 Sq Ft

  2 Ridgecrest Dr, Wingdale, NY 12594

  2 Ridgecrest Dr, Wingdale, NY 12594
• 

  

  /23

  $429,000 Pending

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

  45 Nicole Ln, Wingdale, NY 12594

  Experience the charm of this classic raised ranch, located in the suburban town of Wingdale, NY, within Dutchess County. This home offers 3 bedrooms and 2 full baths, including a private ensuite in the primary bedroom. The spacious kitchen flows into a separate dining and living room, with a fireplace, creating a warm and inviting atmosphere. Additionally, this home has a partially finished

  Gianna Schiavone Compass Greater NY, LLC

  45 Nicole Ln, Wingdale, NY 12594
• 

  $205,000 Sold Jun 05, 2025

  • 1,048 Sq Ft
  • $196/SF
  • 68 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1992

  126 Reagans Mill Rd, Wingdale, NY 12594

  Welcome to 126 Reagan Mills Rd a well cared for home offering one level living. This home boasts an open-concept layout, allowing for seamless flow between the spacious living room, dining area, and kitchen. There are 2 spacious bedrooms along with an additional room in the back of the home. The additional room is perfect for a home office. The home has forced air oil heat and central air.

  Mark Snyder eXp Realty

  126 Reagans Mill Rd, Wingdale, NY 12594
• 

  Est $348,849 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,736 Sq Ft

  27 Dwy Ln, Wingdale, NY 12594

  27 Dwy Ln, Wingdale, NY 12594
• 

  

  /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
• 

  $315,000 Sold May 30, 2025

  • 1,080 Sq Ft
  • $292/SF
  • 76 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2005

  19 Nanas Way, Wingdale, NY 12594

  Nestled on a secluded and private cul de sac with fully developed trees, lies 19 Nanas Way, a light filled 3 bedroom, 2 full bath ranch style home. This is one level living at its best. The kitchen, dining, and living area featuring cathedral ceilings is open concept. The kitchen boasts Bosch SS appliances and a separate pantry. The kitchen door allows direct access to a large walk out deck, with

  Michael Manzino Brown Harris Stevens

  19 Nanas Way, Wingdale, NY 12594
• 

  Est $573,564 Not Listed For Sale

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

  74 Hi View Dr, Wingdale, NY 12594

  74 Hi View Dr, Wingdale, NY 12594
• 

  

  /12

  $575,000 Coming Soon

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

  283 Johnson Rd, Wingdale, NY 12594

  FANTASTIC opportunity to purchase a Beautiful Home on .65 acres - Sellers are INCLUDING an adjoining .48 lot with Two Huge Detached Garages were built in 2015, 40 X 28 and 24 X 24! Taxes include Both Properties. Combined acreage is 1.13. Let's begin with the house. Inviting tri-level home was completely renovated in 2002 and expanded with a huge second floor primary suite. LED lighting throughout

  Lisa Liffland McGrath Realty Inc

  283 Johnson Rd, Wingdale, NY 12594
• 

  $490,000 Sold May 20, 2025

  • 3,136 Sq Ft
  • $156/SF
  • 18 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1988

  7 Riverdale Dr, Wingdale, NY 12594

  Welcome to 7 Riverdale Drive in sought-after Country Mill Estates! This newly renovated spacious home features 3-bedroom, 2 full baths & finished lower level offering a perfect blend of modern elegance and comfortable living. Situated on a private 0.83 level acres with beautiful mountain views! The open floor plan provides an inviting space, ideal for both relaxing and entertaining with new

  Susan Stevens BHHS Hudson Valley Properties

  7 Riverdale Dr, Wingdale, NY 12594
• 

  Est $351,793 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,550 Sq Ft

  34 Holly Hill Dr, Wingdale, NY 12594

  34 Holly Hill Dr, Wingdale, NY 12594
• 

  

  /10

  $130,000

  • 3 Beds
  • 1 Bath
  • 1,440 Sq Ft

  23 Clearview Rd, Wingdale, NY 12594

  23 Clearview Rd, Wingdale, NY – Multi-Family OpportunityTwo homes for the price of one! This unique multi-family property sits on a .38-acre lot and includes a detached two-car garage—perfect for extra storage or workshop space. The main home features a primary bedroom with an ensuite bath, plus two additional bedrooms, a spacious kitchen, and a comfortable living room. The second home offers

  Peggy MacLeay-Generoso McGrath Realty Inc

  23 Clearview Rd, Wingdale, NY 12594
• 

  $95,000 Sold Mar 03, 2025

  • 996 Sq Ft
  • $95/SF
  • 32 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1930

  107 Hutchinson Ave, Wingdale, NY 12594

  Looking for a great opportunity? Look no more! This property has tons of potential and is average in living space size for the neighborhood. It is located close to main roads with easy access to local amenities, such as shopping, banking, schools, and various eateries. Per our TAX/BPO describe the property as a MFR (2fam) built in 1930. It has a GLA of approx. 996 and has 2 bedroom and 2Baths,

  Neven Spralja REALHome Services & Solutions

  107 Hutchinson Ave, Wingdale, NY 12594
• 

  Est $440,244 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,180 Sq Ft

  29 Holly Hill Dr, Wingdale, NY 12594

  29 Holly Hill Dr, Wingdale, NY 12594
• 

  

  /4

  $100,000

  • Land
  • 1.00 Acre
  • $100,000 per Acre

  149 Johnson Rd, Wingdale, NY 12594

  Land for sale with board of health approval- Approved plans for a 3 bedroom, 3 bathroom raised ranch home. Well is drilled, land is ready to start building your dream home today

  Bliss Voutsinas

  149 Johnson Rd, Wingdale, NY 12594
• 

  $420,000 Sold Feb 27, 2025

  • 1,554 Sq Ft
  • $270/SF
  • 47 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1988

  9 White Farm Rd, Wingdale, NY 12594

  Welcome to County Mill Estates, where this charming 3-bedroom, 2-bath raised ranch combines comfort and versatility. The country kitchen, outfitted with stainless steel appliances, opens onto a deck with lovely views of the expansive backyard. Adjacent to the kitchen, a cozy living room with a wood-burning fireplace offers the perfect retreat on chilly evenings. Down the hall, the primary

  Mark Boyland Keller Williams Realty Partner

  9 White Farm Rd, Wingdale, NY 12594
• 

  Est $429,414 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,284 Sq Ft

  6 Holly Hill Dr, Wingdale, NY 12594

  6 Holly Hill Dr, Wingdale, NY 12594
• 

  

  /24

  $339,999

  • 3 Beds
  • 2 Baths
  • 1,459 Sq Ft

  218 Johnson Rd, Wingdale, NY 12594

  Charming 3-Bedroom Home on 2.5 Acres in WingdaleWelcome to this well-maintained 3-bedroom, 2-bathroom single-family home offering 1,459 sq. ft. of comfortable living space. Nestled on 2.5 private acres in Wingdale, this home combines peace, privacy, and practicality—perfect for those seeking a forever home. Home is being sold AS-IS.Recent updates include a new sump pump, front

  Jennifer McQueen-Sealy Clarke Realty & Associates LLC

  218 Johnson Rd, Wingdale, NY 12594
• 

  $405,000 Sold Feb 07, 2025

  • 1,572 Sq Ft
  • $258/SF
  • 21 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1965

  317 Dog Tail Corners Rd, Wingdale, NY 12594

  Unique opportunity to own this charming property with a rich history as a successful Community Supported Agriculture (CSA) farm! This peaceful, country home has 3 nicely sized bedrooms, 1.5 tastefully updated baths (main bath has radiant heated flooring) and lovely hardwood flooring throughout. From the moment you step inside, you’ll notice the amazing natural sunlight this home is enveloped

  Jennifer Amicucci

  317 Dog Tail Corners Rd, Wingdale, NY 12594
• 

  Est $333,567 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,632 Sq Ft

  3677 Pleasant Ridge Rd, Wingdale, NY 12594

  3677 Pleasant Ridge Rd, Wingdale, NY 12594
• 

  

  /11

  $169,000

  • 3 Beds
  • 1 Bath
  • 1,092 Sq Ft

  14 SE Mountain Rd, Wingdale, NY 12594

  RARE FIND !! FULLY DETACTED 3 BR / 1 BTH / SPLIT LEVEL SINGLE FAMILY HOUSE W UNFIN. BSMT & FULL REAR DECK W LARGE WRAP AROUND BACK YARD LOCATED IN THE HEART OF PEACE AND TRANQILITY OF WINGDALE.. Featurning 3 BR's + WALK IN LARGE PANTRY ( 1st Floor Walk In Bedroom) Living Room, Kitchen, Basement, Large Back & Side Yard. Septic Tank for plumbing and Underground Oil Tank For Heating (SELLER NOT

  Crystal Jones Voro LLC

  14 SE Mountain Rd, Wingdale, NY 12594
• 

  $430,000 Sold Jan 31, 2025

  • 2,448 Sq Ft
  • $176/SF
  • 52 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1965

  62 Hoag Corners Rd, Wingdale, NY 12594

  First time on the market since 1965, this home was renovated & expanded in 1995. Set far back from the road on .65 acres of completely level land backing onto a beautiful open space with magnificent mature trees. There is an outdoor shed for storage, a whole house generator, garage is actually big enough for 3 cars. The windows have all been replaced, the kitchen has been updated with a sun room.

  Gillian Stewart Gillian Stewart Real Estate

  62 Hoag Corners Rd, Wingdale, NY 12594
• 

  Est $378,606 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,380 Sq Ft

  115 Reagans Mill Rd, Wingdale, NY 12594

  115 Reagans Mill Rd, Wingdale, NY 12594
• 

  

  /3

  $89,900

  • Land
  • 5 Acres
  • $17,767 per Acre

  0 Sheldon Rd Unit KEY832601, Dover, NY 12594

  Sheldon Rd is peaceful and quiet, not a through road. The road is town maintained. Residential use only, Off-the-Grid homes are acceptable. Upward sloping property is lightly wooded with a pretty seasonal view.

  Lisa Liffland McGrath Realty Inc

  0 Sheldon Rd Unit KEY832601, Dover, NY 12594

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