22

Dover Plains, NY Houses for Sale

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  • /44

    $275,000

    • 2 Beds
    • 2 Baths
    • 1,836 Sq Ft

    3465 Route 22, Dover Plains, NY 12522

    Experience serene country living at 3465 Route 22, Dover Plains, NY 12522! This spacious, well-maintained ranch-style home offers the perfect blend of comfort and style, set back from the road for privacy and boasting breathtaking panoramic views of the surrounding Hudson Valley landscape. Step inside to discover a bright and inviting living room, complete with a cozy fireplace—perfect for

    Agent Photo

    Omar Harper

    Epique Realty

    (845) 599-0147

    3465 Route 22, 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

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    Larry Havens

    Havens Real Estate

    (845) 506-8855

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

    Agent Photo

    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

    Agent Photo

    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
  • /27

    $1,150,000

    • 2 Beds
    • 1 Bath
    • 1,216 Sq Ft

    447 Butts Hollow Rd, Dover Plains, NY 12522

    It seems to be a human instinct to define utopia as a garden, and this Millbrook property on Butts Hollow Road unequivocally deserves that designation. Not only gardens—which have been lovingly created and curated—but meadows and forest glens, falling water and meandering paths. Regardless of season, there is always something unexpected and lovely to greet you—a rippling sea of red poppies,

    Candy Anderson Compass Greater NY, LLC

    447 Butts Hollow Rd, Dover Plains, NY 12522
  • /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
  • /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
  • /18

    $500,000

    • 4 Beds
    • 2.5 Baths
    • 3,016 Sq Ft

    10 May Knoll, Dover Plains, NY 12522

    SELLER FINANCING AVAILABLE>The Adirondack is YOUR Perfect Waterfront Getaway. Tranquility, endless possibilities and the warm vibes of the Hudson Valley welcome you. Situated on 1.951 acres along the majestic Ten Mile River. The home features an Old World charm with custom woodwork, built-in-cabinets, hardwood floors, a unique stone fireplace and your very own private balcony overlooking the

    Dani Dorman Real Broker NY LLC

    10 May Knoll, Dover Plains, NY 12522
  • /38

    $425,000

    • 4 Beds
    • 3 Baths
    • 1,792 Sq Ft

    263 Bog Hollow Rd, Wassaic, NY 12592

    Welcome to this beautifully renovated 4-bedroom, 3-bath Colonial style home nestled on 2.9 private acres in the charming town of Amenia, NY. The open concept living room features a pellet stove and access to the kitchen and 1st floor bathroom. The kitchen hs stainless steel appliances and butcher block counters and cute breakfast nook. The laundry room is on the first floor. Aslo on the main

    Christopher Ferraro RE/MAX Town & Country

    263 Bog Hollow Rd, Wassaic, NY 12592
  • /35

    $375,000

    • 3 Beds
    • 1 Bath
    • 1,786 Sq Ft

    53 Glen Ave, Dover Plains, NY 12522

    Charming, cozy and clean, you can move right in and live low-maintenance in this perfect home.The entire back end of the property abuts Butts Hollows Brook which runs year round and flows into Ten Mile River. Enjoy summers in the above ground pool with a beautiful brand new liner. Conveniently located 2 miles from Dover Plains train station. Shopping, schools and recreation are all nearby. This

    Diana Lenz BHHS Hudson Valley Properties

    53 Glen Ave, Dover Plains, NY 12522
  • /32

    $299,900

    • 2 Beds
    • 1.5 Baths
    • 1,416 Sq Ft

    126 Christian Hill Rd Unit 128, Dover Plains, NY 12522

    Charming Property with Potential Overview This lovely property is nestled within a robust estate area, offering the perfect blend of tranquility and opportunity. Set on 2 acres of land, the surroundings feature mature trees, a sweeping lawn, and the privacy that creates a serene oasis. Natural Light: The home benefits from ample natural light, enhancing the open feel of the kitchen and living

    Toni Soule Bain Real Estate

    126 Christian Hill Rd Unit 128, 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

    LUCIANA BENNETT McGrath Realty Inc

    198 Benson Hill Rd, Dover Plains, NY 12522
  • /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
  • /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
  • /43

    $20,000,000

    • 4 Beds
    • 8 Baths
    • 7,500 Sq Ft

    365-381 Tower Hill Rd, Wassaic, NY 12592

    A Private Architectural Masterpiece on 165 AcresNestled along the border of Amenia and Millbrook, NY, this extraordinary 165-acre estate offers unparalleled privacy and breathtaking panoramic views of the Hudson Valley. Designed by the acclaimed Resolution: 4 Architecture and completed in 2019, the 7,500-square-foot modern residence harmonizes seamlessly with its natural surroundings.At the heart

    Noble Black Douglas Elliman Real Estate

    365-381 Tower Hill Rd, Wassaic, NY 12592
  • /40

    $8,000,000

    • 6 Beds
    • 9 Baths
    • 8,933 Sq Ft

    33 Nodine Pasture Rd, Kent, CT 06757

    West Wind Hill, a bespoke country estate on 389 acres sits on the crest of a plateau overlooking panoramic protected views. Classic stone and shingle manor house with formal courtyard sited perfectly to experience spectacular sunsets and fairytale mists combined with the upmost in privacy. Access is via a private gated road that winds through trees, past old stone walls with glimpses of open

    Jill Sloane Brown Harris Stevens

    33 Nodine Pasture Rd, Kent, CT 06757
  • /25

    $12,950,000

    • 4 Beds
    • 4.5 Baths
    • 6,191 Sq Ft

    123 Butts Hollow Rd, Dover Plains, NY 12522

    Welcome to a once-in-a-lifetime opportunity to own an exceptional equestrian estate sprawling over approximately 185 unrestricted acres in the heart of Millbrook hunt country. Originally built in 1865, this property has been meticulously expanded with a lavish addition spanning over 6000 sq ft, seamlessly blending antique charm with modern opulence. Enjoy miles of fenced pastures, riding trails,

    OLIVER BROWN Houlihan Lawrence Inc.

    123 Butts Hollow Rd, Dover Plains, NY 12522
  • /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

    $8,000,000

    • 6 Beds
    • 8 Baths
    • 8,933 Sq Ft

    Unlisted Address

    Perched on the crest of a plateau overlooking panoramic, protected views, West Wind Hill, a bespoke country estate on 389± acres, straddles Kent, CT and Amenia, NY. Experience this truly magnificent classic stone and shingle manor house sited perfectly to experience lush sunsets and fairytale mists with the upmost in privacy. Only eight minutes from the center of Kent and less than two

    Joseph Lorino Brown Harris Stevens HV LLC

    Unlisted Address
  • /30

    $2,995,000

    • 6 Beds
    • 6 Baths
    • 6,118 Sq Ft

    644 Tower Hill Rd, Millbrook, NY 12545

    Experience the charm of country living in Millbrook with this 110-acre estate. As you wind your way along the quaint country road and up the circular driveway, you're greeted by manicured lawns, lush pastures, and majestic oak trees, setting the stage for the grandeur that awaits. The main residence, a masterpiece of architectural design, boasts over 6,000 sqft of traditional elegance blended

    OLIVER BROWN Houlihan Lawrence Inc.

    644 Tower Hill Rd, Millbrook, NY 12545
  • /2

    $225,000

    • 4 Beds
    • 3 Baths
    • 2,912 Sq Ft

    141 Poplar Hill Rd, Wassaic, NY 12592

    ***Note that the list price is NOT indicative of the seller's final reserve amount; it is just the starting auction bid amount*** This 2900+ SF home sits on an 8+ acre lot. This property is eligible under the Freddie Mac First Look Initiative through 7/22/2025. It is sold only to owner-occupants, non-profit organizations, and government entities during the First Look period. This property is part

    Igor Krasnoperov Rising Star Realty

    141 Poplar Hill Rd, Wassaic, NY 12592
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