Dover Plains, NY Homes 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

  

  Omar Harper

  Epique Realty

  (845) 599-0147

  3465 Route 22, Dover Plains, NY 12522
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  /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

  

  Larry Havens

  Havens Real Estate

  (845) 478-1624

  105 S Nellie Hill Rd, Dover Plains, NY 12522
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  /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

  

  Larry Havens

  Havens Real Estate

  (845) 493-2818

  10 Raymond Ave, Dover Plains, NY 12522
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  /10

  $359,000

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

  39 Maple Ln, Dover Plains, NY 12522

  Accepted Offer 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

  

  Larry Havens

  Havens Real Estate

  (845) 506-8855

  39 Maple Ln, Dover Plains, NY 12522
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  /15

  $215,000

  • Land
  • 9 Acres
  • $23,395 per Acre

  0 Kent Rd Unit 20252538, Amenia, NY 12592

  Welcome to 9.19 acres of rolling meadow, offering breathtaking vistas of the Eastern Dutchess County countryside. Tucked away from the road, this peaceful and private setting provides the perfect canvas for your dream home.Whether you're envisioning a simple retreat, a working farm, or a lush garden oasis, this land supports a wide range of possibilities.Enjoy easy access to Metro-North,

  

  Larry Havens

  Havens Real Estate

  (845) 442-1853

  0 Kent Rd Unit 20252538, Amenia, NY 12592
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  /11

  $215,000

  • Land
  • 9 Acres
  • $23,395 per Acre

  0 Kent Rd Unit KEY882325, Amenia, NY 12592

  9.19 versatile acres with remarkable vistas of the gorgeous Eastern Dutchess County countryside. At the moment you will have the ability to select a site for your dream home on this open rolling open meadow. Offering privacy and set well off the road the ideal homesite welcomes your vision and ingenuity.This parcel is currently being used as a hayfield; however, your horticultural and

  

  Larry Havens

  Havens Real Estate

  (845) 439-2876

  0 Kent Rd Unit KEY882325, Amenia, NY 12592
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  /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

  (845) 335-3774

  45 Riverdale Dr, Wingdale, NY 12594
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  /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
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  /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
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  /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
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  /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
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  /23

  $110,000

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft

  151 Scott Dr, Dover Plains, NY 12522

  Beautiful Home in the Tally Ho Senior Community!Nestled on a premium lot, this charming and spacious home offers comfortable living in the desirable Tally Ho 55+ community. Step into the bright and open living room, dining area, and kitchen, all featuring vaulted ceilings that enhance the sense of space and light. The large kitchen is a chef’s dream, boasting abundant cabinetry and

  Blake Michaud Serhant LLC

  151 Scott Dr, Dover Plains, NY 12522
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  /14

  $80,000

  • Land
  • 1.01 Acres
  • $79,208 per Acre

  15 Evan Rd, Dover Plains, NY 12522

  Attention builders and end users! Level, cleared and shovel ready 1 acre lot in the heart of Dover Plains! Current 4 bedroom BOHA, no fill required for the septic. Backing up to 16+ acres of farm land, come build your dream home today! Bring your own builder or ask about options. Excellent location, minutes to town, the Town of Amenia, Wassaic Train Station, culinary grade restaurants shops and

  Justin LaFalce KW MidHudson

  15 Evan Rd, Dover Plains, NY 12522
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  /29

  $389,000

  • 2 Beds
  • 2 Baths
  • 1,248 Sq Ft

  154 Bog Hollow Rd, Wassaic, NY 12592

  Discover serene country living in this beautifully maintained Ranch nestled on over 7 private acres. Enjoy the ease of single-level living with an open floor plan that seamlessly connects the kitchen and living room—perfect for entertaining. The formal dining area opens to a spacious deck, offering views of the backyard and a cozy fire pit, ideal for gatherings under the stars.This

  Stephen Pener William Pitt Sothebys Int Rlty

  154 Bog Hollow Rd, Wassaic, NY 12592
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  /9

  $275,000

  • Land
  • 15 Acres
  • $17,776 per Acre

  0 Cricket Hill Rd, Wingdale, NY 12594

  This land is ready for you to fulfill your dreams. 15.47 acres in a pastoral setting. With multiple potential hilltop building sites, choose your view from awe inspiring western sunsets to eastern mountain views overlooking the Ten Mile River. There is plenty of room up top to build your country escape and fulfill your dreams, whether it is adding a barn for a small hobby farm, avid collector,

  Brian McGrath McGrath Realty Inc

  0 Cricket Hill Rd, Wingdale, NY 12594
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  /19

  $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
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  /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
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  /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
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  /3

  $89,000

  • Land
  • 1.49 Acres
  • $59,732 per Acre

  0 Tinker Town Rd, Dover Plains, NY 12522

  Escape the NYC and envision your perfect getaway on this beautiful 1.49 acre lot in Amenia, NY. Nestled in the beautiful Dutchess County, this level plot offers endless possibilities for those looking to build a custom home or business or both. This property provides a canvas for your dreams . A Natural Haven Just Minutes from Modern Conveniences, The lots proximity to the Taconic State Parkway

  Adnane Chahi Keller Williams Realty Partner

  0 Tinker Town Rd, Dover Plains, NY 12522
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  /2

  $180,000

  • Land
  • 5.00 Acres
  • $36,000 per Acre

  591 Bog Hollow Rd, Wassaic, NY 12592

  Discover the perfect blend of peace, privacy, and potential with this beautiful 5-acre residential building lot located in the scenic hamlet of Wassaic, NY. Nestled in the heart of Dutchess County, this spacious parcel offers a rare opportunity to build your dream home or weekend retreat surrounded by nature. With ample space for a custom residence, gardens, and outdoor living areas, the

  Tiffiany West RE/MAX Distinguished Hms.&Prop

  591 Bog Hollow Rd, Wassaic, NY 12592
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  /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
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  /2

  $100,000

  • Land
  • 0.83 Acre
  • $120,482 per Acre

  9 Terbar 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

  9 Terbar Ct, Dover Plains, NY 12522
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  /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
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  /33

  $429,000

  • 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
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  /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
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  /6

  $120,000

  • Land
  • 4.53 Acres
  • $26,513 per Acre

  3733 New York 22, Wassaic, NY 12592

  Fantastic opportunity to build your dream home on the spacious on this 4.526 acre lot. Enjoy peace and privacy with a driveway. Don't miss your chance to create your ideal living space in this desirable location.

  Laurie Mainey KW MidHudson

  3733 New York 22, Wassaic, NY 12592
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  /9

  $1,075,000

  • Land
  • 86 Acres
  • $12,500 per Acre

  Northrup Northrup Rd, Dover, NY 12522

  A special property for someone seeking a quiet private location to create an estate with great view potential. The property is grown over but offers approximately 4o plus or minus acres of crop land if and when reclaimed. High elevations -highest point is 1050 feet. Excellent location, conveniently situated to Millbrook Village, Amenia Village, Kent, Ct., and only two miles to the Hamlet of

  Robert D Ferris R. Ferris Real Estate, LLC

  Northrup Northrup Rd, Dover, NY 12522
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  /19

  $165,000

  • Land
  • 5 Acres
  • $32,353 per Acre

  565 Halls Corners Rd, Dover Plains, NY 12522

  Builder's Dream... A lot was Completed on this Property, survey, well, electric, foundation started, driveway started and more. Build your DREAMHOME on this Beautiful Magnificent Property with BOHA 5.1 acre lot. Many Permits are Completed. Well/ Septic and plans are Board of HealthApproved for a 3 Bedroom home, valid thru July 2027. Completed projects include: Survey. 1+ acre building

  Helen Sclafani World Homes Realty

  565 Halls Corners Rd, Dover Plains, NY 12522
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  /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
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  /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
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  /14

  $135,000

  • 3 Beds
  • 1.5 Baths
  • 1,900 Sq Ft

  160 Holpsapple Rd Unit 52, Dover Plains, NY 12522

  Welcome to this charming 3-bedroom, 2-bathroom mobile home in Dover! Enjoy the open floor plan with a spacious living area, perfect for gatherings. The well-appointed kitchen offers ample storage, and the primary suite comes with a private bath for added comfort. With two additional bedrooms, this home is perfect for all! Located in a great community, close to local amenities and schools. Don't

  MICHAEL SANTARPIA K. Fortuna Realty, Inc.

  160 Holpsapple Rd Unit 52, Dover Plains, NY 12522
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  /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
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  /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
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  /21

  $7,900,000

  • Land
  • 442 Acres
  • $17,874 per Acre

  1297 New York 343, Dover Plains, NY 12522

  Nestled in the heart of natural beauty, this extraordinary property offers over 440 acres of pristine land in the municipality of Washington. A rare find, this expansive tract of land is a harmonious blend of rolling hay fields, lush pastures, mature hardwood forests, three tranquil ponds and meandering stream. The property rises from east to west, providing breathtaking views across the Harlem

  Brian McGrath McGrath Realty Inc

  1297 New York 343, Dover Plains, NY 12522
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  /9

  $760,000

  • Land
  • 70 Acres
  • $10,857 per Acre

  80 Hunter Ln, Amenia, NY 12592

  HUNTERS PARADISE:Hunters Incredible hunting land with large cabin spring fed water system, hot water system full bath and shower Cabin has two bedrooms and a loft sleeps 8 comfortably with wood stove and fireplace for heat. All electric is run by generator. You supply generator There are total 132.4 acres in three parcels taxes 2943.00 13200000716400008885890000 70

  Bill Flood Houlihan Lawrence Inc.

  80 Hunter Ln, Amenia, NY 12592
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  /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, and

  Adam Hade Compass Greater NY, LLC

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

  $205,000

  • Land
  • 2.50 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, and

  Adam Hade Compass Greater NY, LLC

  0 New York 22, Dover Plains, NY 12522
• 

  

  /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, and

  Adam Hade Compass Greater NY, LLC

  0 New York 22, Dover Plains, NY 12522
• 

  /2

  $119,000

  • Land
  • 13 Acres
  • $8,941 per Acre

  0 Cart Rd Unit KEY833895, Dover, NY 12522

  Nice wooded property with frontage on Cart Rd and 343. Ideal for camp or your hunting cabin. Beautiful view of the town. Priced to sell. 40+ acres also for sale, next to it.

  Graziano Tassone Tassone Realty Corp.

  0 Cart Rd Unit KEY833895, Dover, NY 12522
• 

  /2

  $119,000

  • Land
  • 13 Acres
  • $8,941 per Acre

  0 Cart Rd Unit KEYH6268558, Dover, NY 12522

  Nice wooded property with frontage on Cart Rd and 343. Ideal for camp or your hunting cabin. Beautiful view of the town. Priced to sell. 40+ acres also for sale, next to it.

  Graziano Tassone Tassone Realty Corp.

  0 Cart Rd Unit KEYH6268558, Dover, NY 12522

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