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Dover Plains, NY Homes for Sale

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  • /46

    $795,000

    $20K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 2,234 Sq Ft

    360 Old State Route 22, Dover Plains, NY 12522

    Stunning Riverfront Retreat offers serene water views and the luxury of fishing and kayaking right in your own backyard. Beautifully renovated three-bedroom home is complemented by a one-bedroom pool house that works perfectly as a guest cottage - true resort-style living. Open-concept living and dining areas are filled with natural light, featuring two sets of French doors that lead to a

    Agent Photo

    Judith 'Judy' Albert

    BHHS Hudson Valley Properties

    360 Old State Route 22, Dover Plains, NY 12522
  • /2

    $100,000

    • Land
    • 36,154 Sq Ft
    • $120,482 per Acre

    9 Ter Bar Ct, Dover Plains, NY 12522

    Beautiful flat building lot, no clearing needed! Board of health approved for 4 bedroom home and you only need a small septic on this lot which makes building a home here more cost effective! This level lot is perfect to build your dream home. Bring your own builder or use ours! We can help and assist the first time homebuyer build their dream home through the whole process.

    Bliss Voutsinas Hillside Realty & Development

    9 Ter Bar Ct, Dover Plains, NY 12522
  • /12

    $314,900

    • 2 Beds
    • 1 Bath
    • 1,378 Sq Ft

    122 Weil Rd, Wingdale, NY 12594

    Two bedroom, one bath cottage on an amazing pastoral setting on a 6.16 acre lot in the town of Dover. Great place for a weekend retreat or year-round home. Bring your imagination and renovate this home to your needs. Amazing setting! Sold as-is. Buyer to pay NYS and any local transfer taxes. Offers with rehab loan financing must be accompanied by a pre-qualification letter; cash offers with proof

    Brian Smith River Realty Services, Inc.

    122 Weil Rd, Wingdale, NY 12594
  • /30

    $275,000

    • 5 Beds
    • 2 Baths
    • 2,100 Sq Ft

    14-16 Glen Hill, Dover Plains, NY 12522

    Surrounded by nature. An affordable compound in the quiet hamlet of Dover Plains—an increasingly rare opportunity to own two dwellings for the price of one. This unique property features a 3-bedroom/1-bath residence and a separate 2-bedroom/1-bath residence, both in solid condition with some TLC needed to make them your own. Set on a picturesque parcel at the end of a country road, the setting is

    Barry Malawer Coldwell Banker Realty

    14-16 Glen Hill, Dover Plains, NY 12522
  • /43

    $899,000

    • 3 Beds
    • 2 Baths
    • 1,686 Sq Ft

    73 Lake Ellis Rd, Wingdale, NY 12594

    A rare opportunity for the dedicated equestrian, this beautiful gentleman’s farm is set on nearly 9 acres of gently rolling countryside, offering the ideal balance of privacy, usability and convenience. Whether you’re an active competitor, trail rider or simply seeking a peaceful horse property, this special offering provides the setting to pursue your passion.Perfect as a full-time residence

    Lonnie Lum Coldwell Banker Realty

    73 Lake Ellis Rd, Wingdale, NY 12594
  • /26

    $16,500,000

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

    365 Tower Hill Rd, Wassaic, NY 12592

    Introducing Sky House. This 7,500-square-foot modern estate atop 165 acres of meadows, woodland, and rolling hills in Millbrook’s storied hunt country is a study in serenity and design intelligence. Conceived by the celebrated firm Resolution: 4 Architecture and completed in 2019, the residence rises from the landscape with a long, linear silhouette tempered by floor-to-ceiling glass that invites

    Ashley Whittaker Spence Compass Greater NY, LLC

    365 Tower Hill Rd, Wassaic, NY 12592
  • /23

    $175,000

    $20K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,056 Sq Ft

    110 Gina Dr, Dover Plains, NY 12522

    Beautifully maintained and absolutely gorgeous double manufactured home offering spacious open-concept living in the desirable Tally Ho 55+ community. This home features a large living room with a cozy electric fireplace and a gourmet kitchen loaded with extras, including refrigerator, dishwasher, microwave, propane stove, abundant cabinetry, and a breakfast island perfect for casual dining and

    Robert Dunlop Havens Real Estate

    110 Gina Dr, Dover Plains, NY 12522
  • /16

    $950,000

    • 4 Beds
    • 2 Baths
    • 3,005 Sq Ft

    41 Flint Rd, Millbrook, NY 12545

    Welcome to The Flint Road Retreat!! Beautifully maintained one-owner ranch situated on 3.53 private acres along a quiet country road, this property offers a peaceful and serene setting with plenty of room to enjoy the surrounding natural beauty, while remaining just minutes from local shops, restaurants and area amenities. The home features stunning hardwood floors, custom cherry cabinetry,

    AURA QUARTARARO William Pitt Sothebys Int Rlty

    41 Flint Rd, Millbrook, NY 12545
  • /43

    $425,000

    Open Sun 12PM - 2PM
    • 4 Beds
    • 2 Baths
    • 1,640 Sq Ft

    232 Old Route 22, Wassaic, NY 12592

    Step back in time without sacrificing modern comfort in this authentic 1890 Farmhouse nestled in the heart of Wassaic. From the moment you arrive, the magnificent wraparound porch welcomes you to kick back, relax, and take in the Hudson Valley surroundings.Inside, warmth and character abound with numerous built-ins and old world accents. The charming eat-in kitchen features a cozy

    Kathleen Manikowski Compass Greater NY, LLC

    232 Old Route 22, Wassaic, NY 12592
  • /40

    $3,750,000

    • 7 Beds
    • 7 Baths
    • 6,138 Sq Ft

    151 Benson Hill Rd, Dover Plains, NY 12522

    Rarely does an offering of this scale and provenance come to market. Set across more than 114 acres, Honey Lane Farm is a private estate of exceptional beauty-three distinct period residences forming a serene, self-contained retreat in the heart of the Harlem Valley. The four-bedroom mid-19th century main house is both refined and inviting, bathed in southern light and thoughtfully updated for

    Andrew Gates Houlihan Lawrence

    151 Benson Hill Rd, Dover Plains, NY 12522
  • /35

    $1,650,000

    • 4 Beds
    • 5 Baths
    • 4,604 Sq Ft

    536 Camby Rd, Verbank, NY 12585

    Privately nestled along a picturesque country road, this exceptional country retreat is set on 8.8 acres of beautifully landscaped grounds, offering an extraordinary blend of privacy, comfort, and natural beauty. Surrounded by mature trees and peaceful scenery, the property provides a tranquil escape while remaining conveniently close to the region’s most sought-after destinations. Thoughtful

    Susan Whalen George T Whalen Real Estate

    536 Camby Rd, Verbank, NY 12585
  • /22

    $599,000

    $161K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,386 Sq Ft

    80 Hunter Ln, Amenia, NY 12592

    PRICE JUST REDUCED. DUE TO LIFE EVENTS RECENTLY WILLING TO WORK WITH BUYER THAT CAN APPRECIATE THE PROPERTY. LOCATION LOCATION ONE OF A KIND PROPERTY HUNTING LAND OR A VACATION DESTINATION TO RELAX AND DESTRESS IN THE BEAUTIFUL BERKSHIRE MOUNTAINS 132.4 ACRES PLUS POND.AND 1,368 sq ft cabin.plus 462 sq ft loft. sleeps 8. three land parcels. 70 ACRES 50 ACRES and 12.4 ACRES for a total of 132.4

    John Melchior Howard Hanna Rand Realty

    80 Hunter Ln, Amenia, NY 12592
  • /36

    $475,000

    • 3 Beds
    • 1 Bath
    • 1,680 Sq Ft

    39 Johnson Rd, Kent, CT 06757

    Charming Country Cottage in the Heart of Kent Tucked away on a peaceful private road just a short walk from the vibrant village of Kent. This charming country cottage offers the perfect blend of privacy, convenience, and classic New England character. Surrounded by picturesque meadows and mountain views and located near the scenic Housatonic River, this home provides a tranquil setting while

    Rebecca Ward William Pitt Sotheby's Int'l

    39 Johnson Rd, Kent, CT 06757
  • /23

    $575,000

    $90K PRICE DROP
    • 9 Beds
    • 4 Baths
    • 3,952 Sq Ft

    276 Old Route 22, Wassaic, NY 12592

    Whether you’re seeking an investment property, multi-generational living, or the opportunity to live in one unit while generating rental income from the other two, this versatile property is ready to meet your needs.This well-designed triplex features three townhome-style apartments, each offering three bedrooms, a welcoming front porch, a private rear patio, and a one-car attached

    Stacey Cronin Houlihan Lawrence Inc.

    276 Old Route 22, Wassaic, NY 12592
  • /20

    $4,495,000

    New Construction
    • 4 Beds
    • 5 Baths
    • 5,679 Sq Ft

    101 N Tower Hill Rd, Millbrook, NY 12545

    **TO BE BUILT** Prepare to be impressed. Nestled on nearly 8 private acres in the heart of Millbrook, this exceptional custom-built estate offers nearly 6,000 square feet of thoughtfully designed living space, blending timeless craftsmanship with modern efficiency and luxury. Featuring 4 spacious bedrooms, 5 full baths and oversized 3 car garage, the home provides an ideal balance of comfort,

    Ronald Green KW MidHudson

    101 N Tower Hill Rd, Millbrook, NY 12545
  • /11

    $190,000

    • Land
    • 1.66 Acres
    • $114,458 per Acre

    0 New York 22, Dover Plains, NY 12522

    Located on Route 22 in the town of Dover Plains, this Eight-acre site consists of four lots: 1.66-acre(lot 1), 1.85-acre(lot 2),2.03-acre(lot 3), and 2.5-acre(lot 4) development sites. It is currently being re-zoned to Gateway Commercial (GC) by themunicipality. The purpose of the Gateway district is to encourage the development of a compatible mix of commercial, office,light retail,

    Adam Hade Compass Greater NY, LLC

    0 New York 22, Dover Plains, NY 12522
  • /21

    $499,000

    $30K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,900 Sq Ft

    256 Hammond Hill Rd, Dover Plains, NY 12522

    Privately nestled on 3 serene acres in the rolling hills of Dover Plains, this beautifully reimagined country retreat offers an exceptional blend of privacy, refined modern updates, and effortless indoor-outdoor living. Set far back from the road and surrounded by mature trees and picturesque natural scenery, 256 Hammond Hill Road delivers a peaceful lifestyle with extraordinary entertaining

    Anna Proctor Compass Greater NY, LLC

    256 Hammond Hill Rd, Dover Plains, NY 12522
  • /3

    $345,000

    $105K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 3,318 Sq Ft

    37 Glen Ave, Dover Plains, NY 12522

    2 homes for the price of 1. This is a multi-family property on multiple structures. Two separate electrical meters. 3318 total sq ft with a flowing stream in backyard. Main house consists of 3 bedrooms and 2 baths. Bungalow house has 2 bedrooms and 1 bath. 1 hr to NYC. INVESTORS AND CONTRACTORS SPECIAL. Needs Renovation.

    Ishwar Rameshar YourHomeSold Guaranteed Realty

    37 Glen Ave, Dover Plains, NY 12522
  • /2

    $45,000

    • Land
    • 27,878 Sq Ft
    • $70,312 per Acre

    0 Aldrich Rd, Wingdale, NY 12594

    This 0.64-acre parcel on Aldrich Road in Wingdale, NY is offered at $45,000. This property presents a unique opportunity for an investor or a visionary builder looking to create a custom residence in a quiet, rural setting.Property HighlightsAcreage: 0.64 acres of land in a serene, off-the-beaten-path location.Price: Competitive entry-point pricing at $45,000, reflecting the current

    Mark Snyder eXp Realty

    0 Aldrich Rd, Wingdale, NY 12594
  • /11

    $205,000

    • Land
    • 2.5 Acres
    • $82,000 per Acre

    0 New York 22, Dover Plains, NY 12522

    Located on Route 22 in the town of Dover Plains, this Eight-acre site consists of four lots: 1.66-acre(lot 1), 1.85-acre(lot 2),2.03-acre(lot 3), and 2.5-acre(lot 4) development sites. It is currently being re-zoned to Gateway Commercial (GC) by themunicipality. The purpose of the Gateway district is to encourage the development of a compatible mix of commercial, office,light retail,

    Adam Hade Compass Greater NY, LLC

    0 New York 22, Dover Plains, NY 12522
  • /11

    $195,000

    • Land
    • 1.85 Acres
    • $105,405 per Acre

    0 New York 22, Dover Plains, NY 12522

    Located on Route 22 in the town of Dover Plains, this Eight-acre site consists of four lots: 1.66-acre(lot 1), 1.85-acre(lot 2),2.03-acre(lot 3), and 2.5-acre(lot 4) development sites. It is currently being re-zoned to Gateway Commercial (GC) by themunicipality. The purpose of the Gateway district is to encourage the development of a compatible mix of commercial, office,light retail,

    Adam Hade Compass Greater NY, LLC

    0 New York 22, Dover Plains, NY 12522
  • /20

    $599,408

    • 4 Beds
    • 2 Baths
    • 2,148 Sq Ft

    810 New York 343, Dover Plains, NY 12522

    Set on 2.1 serene acres in the heart of Dutchess County, this thoughtfully designed 4-bedroom, 2-bath residence offers a harmonious blend of classic charm and modern functionality. Ideally positioned near the Wassaic Train, the Taconic Parkway, Millbrook, and Dover Plains, the property provides both privacy and convenience. Step inside to discover warm wood floors throughout the main level,

    Arleen Shepley Elyse Harney Real Estate

    810 New York 343, Dover Plains, NY 12522
  • /19

    $599,408

    • 4 Beds
    • 2 Baths
    • 2,148 Sq Ft

    810 Route 343, Dover Plains, NY 12522

    Sophisticated country living in the desirable Millbrook area within the highly regarded Millbrook Central School District. Ideally located close to the charming village, local amenities, and the Wassaic Station for convenient Metro-North access to New York City. Privately set on 2.06 picturesque acres, this light-filled 4-bedroom, 2-bath Cape offers the perfect blend of comfort, versatility, and

    Arleen Shepley Elyse Harney Real Estate

    810 Route 343, Dover Plains, NY 12522
  • /26

    $595,000

    $30K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,409 Sq Ft

    20 Craig Ln, Dover Plains, NY 12522

    A European Inspired Oasis in Dover Plains!This meticulously cared for custom built home is being offered by the original owners for the first time.The impressive front entrance is where the grace and style begins. This 2,409 square foot home has too many custom features to list-making it a MUST SEE!In the primary residence you will find a primary bedroom, 2 additional bedroom, 2 full

    CAROL LYNNE PENTA K. Fortuna Realty, Inc.

    20 Craig Ln, Dover Plains, NY 12522
  • /35

    $499,000

    • 4 Beds
    • 2.5 Baths
    • 2,548 Sq Ft

    35 Benton Rd, Wassaic, NY 12592

    Bring your imagination and vision to Old Benton House, this four-bedroom antique home, privately set amid mature trees, perennial gardens, and peaceful country surroundings. The home is located in the Ten Mile River Valley which is bordered by mountain ridges on both sides, with views of the Taconic Mountains. Rich in historic character, the home showcases original pine and elm hardwood floors,

    Janet Myer Houlihan Lawrence Inc.

    35 Benton Rd, Wassaic, NY 12592
  • /26

    $1,950,000

    • 3 Beds
    • 1 Bath
    • 1,482 Sq Ft

    21-23 Tinker Town Rd, Dover Plains, NY 12522

    A few minutes east of Route 22 on the Dover/Millbrook border in the municipality of Washington, sits 109+ acres of picturesque countryside. Used prior as a dairy farm, this exceptional offering presents a rare opportunity to bring your farming lifestyle dreams to life, or an equestrian property. Comprised of 4 distinct parcels totaling 109+ acres, the property blends open fields, wooded

    Brian McGrath McGrath Realty Inc

    21-23 Tinker Town Rd, Dover Plains, NY 12522
  • /15

    $62,900

    • 2 Beds
    • 2 Baths
    • 924 Sq Ft

    42 Mallard Way, Dover Plains, NY 12522

    This home is in very good move in condition with some updates. This is a 55 and over community. Rent includes taxes, streetlights, water and garbage pick up.

    Richard Rennia Richard A. Rennia

    42 Mallard Way, Dover Plains, NY 12522
  • /2

    $110,000

    • Land
    • 3 Acres
    • $36,667 per Acre

    7 Brookview Rd, Dover Plains, NY 12522

    Private country setting with abundant wildlife to enjoy. Ideally located a short driving distance from Millbrook to the West, Amenia to the North, on the East by Kent, CT, and the South by Pawling. BOHA until 2029, no fill required for a 3 or 4 bedroom home. Close to railroad for NYC commuters. Specific area is known as Ridgebrook Country Estates. Must see to appreciate!

    Robert D Ferris R. Ferris Real Estate, LLC

    7 Brookview Rd, Dover Plains, NY 12522
  • /46

    $2,475,000

    • 4 Beds
    • 4.5 Baths
    • 2,412 Sq Ft

    56 Northrup Rd, Dover Plains, NY 12522

    At the very end of a quiet country road, you'll find 56 Northrup — a stunning, architect-designed retreat blending 19th-century farmhouse charm with thoughtful, award-winning modern design. Originally built in 1870 and reimagined by NYC architects Neumann & Rudy, this 33-acre property includes a restored main house, a sleek single-story primary suite addition, and expansive grounds featuring a

    Adam Hade Compass Greater NY, LLC

    56 Northrup Rd, Dover Plains, NY 12522
  • /14

    $5,000,000

    • Land
    • 332.3 Acres
    • $15,047 per Acre

    1297 New York 343, Dover Plains, NY 12522

    Nestled in the heart of the Town of Washington’s breathtaking countryside, this extraordinary 332+ acre property offers a rare opportunity to own an expansive and remarkably diverse landscape in the scenic Harlem Valley. A stunning blend of rolling hay fields, open pastures, mature hardwood forests, three peaceful ponds, and a meandering stream, the land unfolds with incredible natural beauty in

    Brian McGrath McGrath Realty Inc

    1297 New York 343, Dover Plains, NY 12522
  • /23

    $89,999

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft

    160 Holsapple Rd Unit 52, Dover Plains, NY 12522

    Spacious 3-Bed, 2-Bath Double-Wide on Premium Corner Lot in Dover Plains Welcome to this large and bright 3-bedroom, 2-full-bath double-wide home, beautifully situated on a meticulously landscaped corner lot. Offering a wonderful blend of private outdoor space and community perks, this property boasts a lush, thick green lawn and a fantastic rear covered deck that is absolutely perfect for

    Steven Collier BHHS Hudson Valley Properties

    160 Holsapple Rd Unit 52, Dover Plains, NY 12522

Frequently Asked Questions

What are the most popular zip codes in Dover Plains, NY?
The most popular zip codes in Dover Plains, NY include 12522, 12592, 12545, 12501 and 12594.
What are the most popular neighborhoods near Dover Plains, NY?
The most popular neighborhoods near Dover Plains, NY are Stanford and North East.
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