Wingdale, NY Homes for Sale

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  /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

  

  Larry Havens

  Havens Real Estate

  (845) 506-8855

  39 Maple Ln, Dover Plains, NY 12522
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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

  

  Shannon Tully

  McGrath Realty Inc

  (845) 328-6912

  27 Cavelo Dr, Wingdale, NY 12594
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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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  /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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  /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
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  /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
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  /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
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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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  /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
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  /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
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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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  /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
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  /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
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  /32

  $575,000 Coming Soon

  • 3 Beds
  • 3 Baths
  • 2,058 Sq Ft

  283 Johnson Rd, Wingdale, NY 12594

  Fabulous opportunity to purchase a Beautiful Home on .65 level ac on park-like property! Sellers are INCLUDING an adjoining .48 lot with Two Huge Detached Garages 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 home was completely renovated in 2002 and expanded with a huge second floor primary suite. On the main

  Lisa Liffland McGrath Realty Inc

  283 Johnson Rd, Wingdale, NY 12594
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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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  /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
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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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  /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

  $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
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  /4

  $100,000

  • Land
  • 1.00 Acre
  • $100,000 per Acre

  149 Johnson Rd, Wingdale, NY 12594

  Land for sale with board of health approval- Approved plans for a 3 bedroom, 3 bathroom raised ranch home. Well is drilled, land is ready to start building your dream home today

  Bliss Voutsinas

  149 Johnson Rd, Wingdale, NY 12594
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  /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
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  /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
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  /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
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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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  /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
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  /15

  $384,500

  • Land
  • 10 Acres
  • $40,010 per Acre

  4,10,12 River Oaks Ln, Sherman, CT 06784

  Exceptional opportunity to purchase a 3-lot package totaling 9.62 acres in the prestigious gated community of The Club at River Oaks in Sherman, CT. This private enclave features 66 home sites spread across 350 acres, centered around an 18-hole, par-70 golf course that flows naturally through the Berkshire foothills. The three lots-4 River Oaks Lane (3.12 acres) 10 River Oaks Lane(3.07 acres),

  David Landau RE/MAX Right Choice

  4,10,12 River Oaks Ln, Sherman, CT 06784
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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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  /3

  $89,900

  • Land
  • 5 Acres
  • $17,767 per Acre

  0 Sheldon Rd Unit KEY832601, Dover, NY 12594

  Sheldon Rd is peaceful and quiet, not a through road. The road is town maintained. Residential use only, Off-the-Grid homes are acceptable. Upward sloping property is lightly wooded with a pretty seasonal view.

  Lisa Liffland McGrath Realty Inc

  0 Sheldon Rd Unit KEY832601, Dover, NY 12594
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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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  /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
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  /2

  $97,000

  • Land
  • 3.30 Acres
  • $29,394 per Acre

  488 Pleasant Ridge Rd, Poughquag, NY 12570

  Beautiful 3+ acres wooded lot in the Town of Union Vale. Convenient to TSP, Route 55 and Hudson River. BOHA.

  Graziano Tassone Tassone Realty Corp.

  488 Pleasant Ridge Rd, Poughquag, NY 12570
• 

  

  /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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  /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
• 

  

  /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
• 

  

  /7

  $69,900

  • Land
  • 2.70 Acres
  • $25,889 per Acre

  0 Old Pawling Rd Unit ONEH6268329, Dover, NY 12564

  An expansive 2.7-acre parcel of land nestled serenely along a picturesque country road, offering a charming and tranquil setting.The land goes downhill from the road to a designated wetland and then rises quite sharply through mature woodland. This idyllic property is conveniently situated near the highly accessible and major thoroughfare, Route 22, ensuring ease of travel and connectivity to

  Michael Martell eXp Realty

  0 Old Pawling Rd Unit ONEH6268329, Dover, NY 12564
• 

  /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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