26

Wingdale, NY Houses for Sale

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  • /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

    Agent Photo

    Shannon Tully

    McGrath Realty Inc

    (845) 328-6912

    27 Cavelo Dr, Wingdale, NY 12594
  • /34

    $650,000

    • 3 Beds
    • 3 Baths
    • 1,450 Sq Ft

    54 Nanny Hill Rd, Pawling, NY 12564

    This stunning home is brand new from Westchester modular, built with top-of-the-line finishes and quality materials. As soon as you step inside, you'll be greeted by a bright and airy open floor plan that creates a spacious and inviting atmosphere. The chef's kitchen is a standout feature, featuring an oversized island with a prep sink and high-end appliances that are sure to appeal to the

    Kaye Saglibene

    54 Nanny Hill Rd, Pawling, NY 12564
  • /25

    $1,049,000

    • 4 Beds
    • 3.5 Baths
    • 3,350 Sq Ft

    42 Long River Rd, Sherman, CT 06784

    Spend your summer in this beautiful, gated community playing golf on the signature 18-hole course, enjoying a game of tennis or swimming in the heated in ground pool. There is full-service club house complete with a pro shop, pub and restaurant. You can enjoy dining on the patio that overlooks the greens. Inquire about membership details. The home is ready for immediate occupancy, so come up and

    Cynthia Szentkuti Ridgefield Homes Realty

    42 Long River Rd, Sherman, CT 06784
  • /50

    $865,000

    • 4 Beds
    • 6 Baths
    • 4,788 Sq Ft

    211 Cricket Hill Rd, Dover Plains, NY 12522

    This is the one—an exceptional and truly special property offering the perfect blend of refined living, natural beauty, and flexibility. Set against a breathtaking countryside backdrop, this Colonial Farmhouse-style home is nestled on just over 5 private, picturesque acres—perfectly suited for horses, weekend escapes, or year-round living. With nearly 4,800 square feet of thoughtfully crafted

    Sherri Malone Coldwell Banker Realty

    211 Cricket Hill Rd, Dover Plains, NY 12522
  • /47

    $749,900

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

    28 Gobblers Knob Rd, Pawling, NY 12564

    Welcome to 28 Gobblers Knob Road – A Hudson Valley Equestrian Retreat! Nestled in the heart of the stunning Hudson Valley, this beautiful 3-bedroom, 2-bathroom home sits on a breathtaking 20+ acre property offering peace, privacy, and natural beauty in every direction. Whether you're looking for a serene country getaway or a horse property, this one-of-a-kind home is the perfect match. The

    Mark Snyder eXp Realty

    28 Gobblers Knob Rd, Pawling, NY 12564
  • /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
  • /44

    $750,000

    • 3 Beds
    • 4.5 Baths
    • 5,500 Sq Ft

    238 Deer Hollow Rd, Poughquag, NY 12570

    This elegant contemporary colonial style home has 3 bedrooms, 4 baths, a library and is reminiscent of the Nantucket Cottage style with a New York flair. three car attached garage.Built, with septic and well installed, the home is ready for you to finish with heat and plumbing. Electrical 75% complete and interior finishes to your own taste. With a separate home office space, a work life balance

    Howard Payson RE/MAX Town & Country

    238 Deer Hollow Rd, Poughquag, NY 12570
  • /48

    $799,900 Open Sun 1PM - 3PM

    • 4 Beds
    • 2.5 Baths
    • 3,350 Sq Ft

    134 Old Pawling Rd, Pawling, NY 12564

    Beautiful Colonial home, Well Maintained level land W/Meadow view, for the first time on the market .This beautiful home offer 4 bedroom and 2 full bathroom and half Den room on the first floor, Bonus Room on the second floor, Formal living room and formal dining room, 1,25 acres .Gorgeous Oak eating kitchen with sliding door to the deck outside, family room and half bath. Second floor offer 4

    Drita Shala Howard Hanna Rand Realty

    134 Old Pawling Rd, Pawling, NY 12564
  • /38

    $938,500 New Construction

    • 3 Beds
    • 3 Baths
    • 3,500 Sq Ft

    41 Long River Rd, Sherman, CT 06784

    Fully customizable Scandinavian modern home with walkout finished lower level set on a sprawling 5.46 acre lot on Long River Rd in River Oaks Country Club, a private gated golf course community in Sherman, CT. You select exterior & interior colors, finishes, tile/stone, appliances, etc. 3 bd / 3 bath / 3,500 SF open-concept residence with main level primary, seamlessly connects kitchen (w/

    Donna Kennedy Keller Williams Realty

    41 Long River Rd, Sherman, CT 06784
  • /2

    $1,195,000 New Construction

    • 4 Beds
    • 4.5 Baths
    • 3,675 Sq Ft

    60 Long River Rd, Sherman, CT 06784

    River Oaks Golf Course New Construction!! Sherman's best value. New construction 4 bedroom 4.5 bath colonial with open floorplan and 2 primary bedrooms. (main level and upper) Propane heat and Central Air. Composite decking. 9 Ft ceilings on the main level. 3 car attached garage. Hardwood floors throughout. Center island kitchen with large pantry and granite/quartz counters. All bedrooms have

    Joe Chemero Coldwell Banker Realty

    60 Long River Rd, Sherman, CT 06784
  • /24

    $1,850,000

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

    783 N Clove Rd, Millbrook, NY 12545

    Sited far off the road, this charming Colonial Revival home sits discreetly amongst the surrounding fields, meadows, and woodlands comprising the 122 acre property. There are two parcels, the main parcel with house on 77 acres, and the adjacent parcel of 45.7 acres, both spanning North Clove Rd with well over 2000’ of road frontage. The home was built in 1986, with major renovations in 2000, but

    Dan Kessler Compass Greater NY, LLC

    783 N Clove Rd, Millbrook, NY 12545
  • /40

    $425,000

    • 3 Beds
    • 2 Baths
    • 1,397 Sq Ft

    42 Lime Kiln Rd, Dover Plains, NY 12522

    Perfectly set back on beautiful park-like property showcasing spectacular panoramic mountain views and a small babbling brook at the back of the property that flows from the Ten Mile River. Bright spacious floor plan features hardwood floors through first floor, updated granite & maple kitchen with stainless steel appliances, and a recently remodeled bath with a custom tile & seamless glass

    Susan Todd BHHS Hudson Valley Properties

    42 Lime Kiln Rd, Dover Plains, NY 12522
  • /33

    $419,000

    • 4 Beds
    • 2 Baths
    • 1,656 Sq Ft

    198 Benson Hill Rd, Dover Plains, NY 12522

    Your Private Oasis Awaits: A Raised Ranch with Panoramic Views!Discover the potential in this four-bedroom, two-bath raised ranch, perfectly situated on just over an acre of private land. Imagine waking up to breathtaking panoramic mountain views right from your own home!This property offers a fantastic layout, including a finished basement that provides versatile living space with a family room,

    LUCIANA BENNETT McGrath Realty Inc

    198 Benson Hill Rd, Dover Plains, NY 12522
  • /39

    $449,000

    • 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
  • /24

    $450,000

    • 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 floor plan. The

    Jonathan Scarinzi Elyse Harney Real Estate

    25 White Farm Rd, Wingdale, NY 12594
  • /24

    $380,000

    • 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.Recent updates include a new sump pump, front siding, and sunroom windows (2023), along

    Jennifer McQueen-Sealy Clarke Realty & Associates LLC

    218 Johnson Rd, 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
  • /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
  • /37

    $497,500

    • 3 Beds
    • 2 Baths
    • 2,168 Sq Ft

    122 Susan Dr, Poughquag, NY 12570

    Tucked away in the tranquil hills of Poughquag town of Unionvale, this spacious 3-bedroom, 2-bath home has a versatile, finished lower level with walk-out, separate laundry room & full bath has been nicely renovated! Added bonus of expansive finished lower-level w/walk-out on 1.53 private acres set back on 1.53-acre lot backed up to woods for privacy, this bright, light home features updates

    Susan Stevens BHHS Hudson Valley Properties

    122 Susan Dr, Poughquag, NY 12570
  • /33

    $449,000

    • 2 Beds
    • 2 Baths
    • 1,144 Sq Ft

    593 Old State Route 22, Dover Plains, NY 12522

    Discover a remarkable, unique country retreat featuring 2 bedrooms and 2 full bathrooms. This home was completely and impeccably renovated in 2022. Nestled on 3.1 acres of private land, this exquisite property offers peace and tranquility as well as wide open spaces just up the hill behind the home with amazing mountain views. When you enter this open concept home, you immediately feel the

    MAUREEN MCELDUFF MULLANEY BHHS Hudson Valley Properties

    593 Old State Route 22, Dover Plains, NY 12522
  • /39

    $1,795,000

    • 3 Beds
    • 4.5 Baths
    • 5,475 Sq Ft

    1 Cloverleaf Farm S, Sherman, CT 06784

    Experience the epitome of modern luxury in this expansive contemporary home with captivating long-range southerly VIEWS! This architectural masterpiece is designed with an open plan that seamlessly integrates living, dining and kitchen spaces, creating an environment perfect for sophisticated entertaining and comfortable daily living. Culinary adventures await in the state-of-the-art kitchen,

    Alan O'Doherty William Pitt Sotheby's Int'l

    1 Cloverleaf Farm S, Sherman, CT 06784
  • /30

    $1,799,999

    • 2 Beds
    • 1 Bath
    • 1,600 Sq Ft

    165 Duell Hollow Rd, Wingdale, NY 12594

    Exceptional opportunity to acquire this contemporary masterpiece designed by renowned architect Allan Shope. Tucked away in the serene woods of Wingdale, this property spans 29.7 acres and boasts a substantial pond, once part of the historic Camp Sacajawea. The residence is positioned on a secluded, wooded parcel, offering breathtaking views of mountains and the tranquil pond making it an ideal

    Bianca D'Alesandro Serhant LLC

    165 Duell Hollow Rd, Wingdale, NY 12594
  • /13

    $4,675,000

    • 4 Beds
    • 4.5 Baths
    • 4,024 Sq Ft

    114 Brush Hill Rd, Millbrook, NY 12545

    Brush Hill Contemporary is a to-be-built masterpiece in the Hudson Valley with an inviting and expansive floor plan designed to allow freedom to roam with absolute comfort and luxury. Huge southerly views of the Clove Valley, and beyond, through floor to ceiling windows in the public spaces allow for maximum light and an indoor/outdoor flow that enhances every season. The home will consist of

    Byron Anderson Compass Greater NY, LLC

    114 Brush Hill Rd, Millbrook, NY 12545
  • /36

    $1,495,000

    • 6 Beds
    • 4.5 Baths
    • 4,110 Sq Ft

    57 Cedar Berry Ln, Dover Plains, NY 12522

    Just 90 miles north of NYC, this stunning Hudson Valley property offers the ultimate live, work, play lifestyle. Nestled on 4.08 private acres, this custom-built log home captures the vibrant essence of the area, known for its booming art and music scene, farm-to-table eateries, outdoor adventures, and local wineries. Generating over $80,000 in VRBO rental income in 2022, this turnkey estate is

    Lindsay Stevens eXp Realty

    57 Cedar Berry Ln, Dover Plains, NY 12522
  • /7

    $548,000 Open Sat 1PM - 4PM

    • 2 Beds
    • 2 Baths
    • 1,425 Sq Ft

    10 Anderson Rd E, Sherman, CT 06784

    MOVE IN READY! Down sizing? Country retreat? Weekend home? First home? Artist or work from home? Looking for low taxes? This charming, ranch home set in a beautiful serene setting has your name on it. This home has great flow and allows the beautiful outside in- you can feel this the minute you walk through the front door. The living room has almost a full wall of windows showcasing the private

    Ginny Gordon-O’Neill William Raveis Real Estate

    10 Anderson Rd E, Sherman, CT 06784
  • /16

    $349,925

    • 4 Beds
    • 3 Baths
    • 3,697 Sq Ft

    45 Riverdale Dr, Wingdale, NY 12594

    SHORT SALE! SALE SUBJECT TO BANK APPROVAL! THIS IS THE PERFECT HOME FOR THE EXTENDED FAMILY. 4+ BEDROOMS 3 FULL BATHS FULLY FINISHED BASEMENT. A TOTAL OF 3 CAR GARAGE, NICELY LANDSCAPED AND WITHIN CLOSE PROXIMITY TO ALL AMENITIES. BACKYARD SLOPES DOWN TO THE TEN MILE RIVER, GREAT CUL DE SAC LOCATION AND MORE. WELL KEPT. Additional Information: ParkingFeatures:1 Car Attached,2 Car Detached.

    Patricia Cannizzaro Century 21 Alliance Rlty Group

    45 Riverdale Dr, Wingdale, NY 12594
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