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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
  • /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.

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    Patricia Cannizzaro

    Century 21 Alliance Rlty Group

    (845) 335-3774

    45 Riverdale Dr, Wingdale, NY 12594
  • /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

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    Larry Havens

    Havens Real Estate

    (845) 478-1624

    105 S Nellie Hill Rd, 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

    Agent Photo

    Larry Havens

    Havens Real Estate

    (845) 493-2818

    10 Raymond Ave, Dover Plains, NY 12522
  • /10

    $359,000

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

    39 Maple Ln, Dover Plains, NY 12522

    For 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 floors that will change the complexion

    Agent Photo

    Larry Havens

    Havens Real Estate

    (845) 506-8855

    39 Maple Ln, Dover Plains, NY 12522
  • /34

    $625,000

    • 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

    $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 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
  • /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
  • /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

    • 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
  • /31

    $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
  • /24

    $450,000

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

    6 Holly Hill Dr, Wingdale, NY 12594

    Welcome to this beautiful and spacious home offering the perfect blend of comfort and style. Enjoy mountain views from your hot tub surrounded by beautiful landscaping in this immaculate raised ranch in the sought-after Wood Winds development. Featuring 3-Bedrooms and 3-Full Bathrooms, the main level includes a thoughtfully designed layout with all 3-Bedrooms and 2-Full Baths. Indoors you will

    Sabina Rodriguez P R O Links Realty Inc

    6 Holly Hill Dr, Wingdale, NY 12594
  • /38

    $548,000

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

    10 Anderson Rd E, Sherman, CT 06784

    MOVE IN READY! Looking for a country retreat, weekend home, artist escape or a work from home space? This charming, ranch home set in a beautiful serene setting has your name on it. This home has great flow and allows the peaceful outside space 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 garden with

    Ginny Gordon-O’Neill William Raveis Real Estate

    10 Anderson Rd E, Sherman, CT 06784
  • /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

    LUCIANA BENNETT McGrath Realty Inc

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

    It's Pretty in Poughquag! 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 throughout! Step in main level, you'll

    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
  • /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
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