Wingdale, NY Homes for Sale

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  /43

  $825,000

  • 4 Beds
  • 4.5 Baths
  • 2,234 Sq Ft

  360 Old State Route 22, Dover Plains, NY 12522

  A rare offering in today’s market - gorgeous River Front Home with calming water views and fishing every day right in your own back yard. Renovated and updated 3 bedroom home with a one bedroom pool house that doubles as a guest cottage. All the amenities you would expect in the best resort style property. Open concept Living and Dining area with 2 sets of French doors opening to an expansive

  

  Judith 'Judy' Albert

  BHHS Hudson Valley Properties

  (845) 280-5286

  360 Old State Route 22, Dover Plains, NY 12522
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  /38

  $3,900,000

  • 3 Beds
  • 2 Baths
  • 1,933 Sq Ft

  6 Hoyt Rd, Sherman, CT 06784

  Black Dog Farm, owned by artist Elaine Voghelle, an exceptional estate offering a refined storybook ambiance. The fully restored 1803 Antique Eyebrow Colonial Farmhouse is set on 4.6 acres of prime land along the Appalachian Trail. Renovations throughout the home are executed to the highest standard. The property includes several substantial outbuildings, including a three-level cottage, a

  

  Eric Bergers

  William Raveis Real Estate

  (860) 936-9247

  6 Hoyt Rd, Sherman, CT 06784
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  /12

  $3,850,000

  • 4 Beds
  • 4.5 Baths
  • 3,542 Sq Ft

  114 Brush Hill Rd, Millbrook, NY 12545

  Perched above the Clove Valley just minutes from the Village of Millbrook, this exceptional modern residence is designed to celebrate light, landscape, and elevated living in the heart of the Hudson Valley. Set on 51.38 acres of rolling countryside, the home offers breathtaking, panoramic views and a rare sense of privacy, while remaining conveniently close to village amenities. The proposed

  Byron Anderson Compass Greater NY, LLC

  114 Brush Hill Rd, Millbrook, NY 12545
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  /13

  $399,999

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  3057 Pleasant Ridge Rd, Wingdale, NY 12594

  Home needs updating and great potential to expand. Offers walk out basement whichcould be developed for additional spaced. Two car detached garage and house recentlyhad a new roof installed. Located on a county road with easy access on 15 acres with ascenic setting. Less than two hours from New York City and very close to Metro-North.

  Richard Rennia Richard A. Rennia

  3057 Pleasant Ridge Rd, Wingdale, NY 12594
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  /22

  $449,000

  • 3 Beds
  • 2 Baths
  • 1,340 Sq Ft

  41 Holly Hill Dr, Wingdale, NY 12594

  Newly renovated single-family home located in a quiet community. This 3-bedroom, 2-bathroom residence features updated finishes throughout and a bright, functional layout ideal for everyday living. Enjoy the brand new back deck, perfect for outdoor gatherings and relaxation. A 4-car driveway offers ample off-street parking. The partial basement provides additional storage and flexible space.

  Kevin Chin KRC Elegant Homes Realty Corp.

  41 Holly Hill Dr, Wingdale, NY 12594
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  /35

  $650,000

  • 4 Beds
  • 2.5 Baths
  • 3,446 Sq Ft

  786 N Clove Rd, Millbrook, NY 12545

  Escape the hustle and bustle of city life and discover true tranquility at this charming country home, nestled on 3 acres of picturesque, private land that abuts a creek with a built in stone grill. This property offers a unique lifestyle opportunity for those seeking serenity, space, and a connection with nature.The inviting home features a cozy, functional, and light-filled interior,

  Diana Wiemer Houlihan Lawrence Inc.

  786 N Clove Rd, Millbrook, NY 12545
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  /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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  /4

  $100,000

  • Land
  • 1 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 Hillside Realty & Development

  149 Johnson Rd, Wingdale, NY 12594
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  /30

  $1,499,999

  • 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 East End LLC

  165 Duell Hollow Rd, Wingdale, NY 12594
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  /17

  $59,900

  • 2 Beds
  • 2 Baths
  • 924,924 Sq Ft

  62 Cardinal Ct, Dover Plains, NY 12522

  This home is in good condition and is located in a well maintained 55 and over community. Monthly rentincludes: taxes, water, streetlights and garbage pickup.

  Richard Rennia Richard A. Rennia

  62 Cardinal Ct, Dover Plains, NY 12522
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  /2

  $99,900

  • Land
  • 3.3 Acres
  • $30,273 per Acre

  Lot 7 Brookview Rd, Dover, NY 12522

  Located approximately 6.5 miles from the Village of Millbrook. Trains to New York City are available only 3.3 miles away at the Metro North Station in Dover Plains. Picturesque Stone Brook traverses the property. Ideal for your weekend or year-round dream home. Board of Health Approved and no fill required.

  Robert D Ferris R. Ferris Real Estate, LLC

  Lot 7 Brookview Rd, Dover, NY 12522
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  /8

  $150,000

  • Land
  • 0.46 Acre
  • $326,087 per Acre

  20 Hickory Ln, Pawling, NY 12564

  Build your dream home on this exceptional 0.46-acre parcel, offering a rare blend of privacy, nature, and convenience. The property is BOH approved (3 bedroom residential dwelling), providing a smooth path to construction, and is landlocked at the rear, creating a peaceful, secluded setting. Enjoy access to two nearby lakes for fishing or swimming, or relax at the clubhouse. Drive into Pawling

  Tela Cook McGrath Realty Inc

  20 Hickory Ln, Pawling, NY 12564
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  /24

  $950,000

  • 4 Beds
  • 3.5 Baths
  • 3,434 Sq Ft

  128 Old Pawling Rd, Pawling, NY 12564

  Welcome to 128 Old Pawling Road, a beautifully situated property in Pawling, NY. Set back from the road, the home is approached by a long private driveway and gated entrance, offering a sense of privacy while still being part of a neighborhood setting. Resting on over 5 acres, the property showcases stunning mountain views that create an impressive backdrop to everyday living year-round. Whether

  Juliska Martino Compass Greater NY, LLC

  128 Old Pawling Rd, Pawling, NY 12564
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  /9

  $197,271

  • 2 Beds
  • 2 Baths
  • 1,080 Sq Ft

  54 Celeste Dr, Dover Plains, NY 12522

  This is a 55+ Community -Ranch Style home with 2BR and 2Bath. Wonderful community with a Clubhouse and Pool. Also in the process of adding a wood deck for outdoor relaxation. Central Air, propane heating. Double-insulated to keep heating expenses low. Close to Sharon, Ct hospital, grocery shopping, etc.This community offers organized gatherings and events during the year for holidays, etc.

  DOROTA LASOTA-LOPEZ Century 21 Alliance Realty Grp

  54 Celeste Dr, Dover Plains, NY 12522
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  /40

  $999,000

  • 3 Beds
  • 3.5 Baths
  • 3,258 Sq Ft

  6 River Bend Ln, Sherman, CT 06784

  A spacious contemporary located in a resort quality setting. Located above the fairway of the 13th hole of the Club at River Oaks, an 18 hole golf course masterfully designed around the meandering contours of the Housatonic River on beautifully rolling farmland. The home site boasts mountain valley and seasonal river views and is equipped with a heated gunite, infinity edge pool with attached

  Tyler O'Hazo William Pitt Sotheby's Int'l

  6 River Bend Ln, Sherman, CT 06784
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  /2

  $599,000

  • Land
  • 8 Acres
  • $74,875 per Acre

  0 Route 22 Unit ONEH6222664, Dover, NY 12594

  Raw Land - Located on Route 22 in Wingdale/Dover Plains. Approximately 8 acres. The Town of Dover is progressing with a comprehensive rezoning initiative to allow multifamily dwellings to be built OR commercial use buildings IE shopping centers or other uses. Available is survey, and several documents limited topo, tax map, ariels etc. Proposal of a large box store drawings available but not

  Lydia Nioras Commerce Properties

  0 Route 22 Unit ONEH6222664, Dover, NY 12594
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  /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
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  /10

  $1,200,000

  • Land
  • 51.38 Acres
  • $23,355 per Acre

  0 Brush Hill Rd Unit KEY935753, Union Vale, NY 12545

  A stunning 51+ acre parcel offering complete privacy and sweeping long views of the Clove Valley, this idyllic setting is the perfect canvas for your dream retreat. A beautiful blend of open meadow and wooded landscape, the land features both level and gently sloping terrain, highlighted by a seasonal stream and ample space to create your own trail system for recreation, exploration, or nature

  Byron Anderson Compass Greater NY, LLC

  0 Brush Hill Rd Unit KEY935753, Union Vale, NY 12545
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  /2

  $60,000

  • Land
  • 0.58 Acre
  • $103,448 per Acre

  0 Cedar Ln Unit KEY971931, Dover, NY 12594

  This 0.58-acre parcel on Cedar Lane in Dover Plains, NY is Board of Health Approved for a 2 Bedroom Home, is available for $60,000. Located in a quiet, established neighborhood, this property offers a rare opportunity to build a custom home in the scenic Hudson Valley.Property HighlightsAcreage: 0.58 acres of level-to-sloping land, ideal for various residential designs.Location:

  Mark Snyder eXp Realty

  0 Cedar Ln Unit KEY971931, Dover, NY 12594
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  /2

  $45,000

  • Land
  • 0.64 Acre
  • $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
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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 Hillside Realty & Development

  9 Terbar Ct, Dover Plains, NY 12522
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  /23

  $499,000

  • 1 Bed
  • 1 Bath
  • 805 Sq Ft

  105 Sand Hill Rd, Dover Plains, NY 12522

  The Geosphere is a convergence of visionary design, tactical investment and natural sanctuary. Set on 7.18 secluded acres in the heart of Dover Plains, this fully legal, architect-designed geodesic residence and studio building give you something unmistakably distinctive: a home that feels like art, and a property that can perform like an asset. Inside, the striking residence is fully winterized,

  Sheneur Menaker Hudson Modern Co

  105 Sand Hill Rd, Dover Plains, NY 12522
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  /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
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  /6

  $349,999

  • 2 Beds
  • 2 Baths
  • 1,440 Sq Ft

  163 Old State Route 22, Dover Plains, NY 12522

  Discover the perfect blend of potential and land with this quaint cottage in Dover Plains. Nestled on 10.02 acres of expansive property, this two-bedroom, two-bathroom home is ideal for buyers looking to invest in a fixer-upper with endless possibilities. This property is a dream come true for outdoor lovers or those seeking privacy and space to roam, garden, or build. With a very affordable

  German Nielsen Newman Realty Inc

  163 Old State Route 22, Dover Plains, NY 12522
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  /17

  $595,000

  • 3 Beds
  • 1 Bath
  • 2,391 Sq Ft

  804-806 Berkshire Rd Unit 806, Wingdale, NY 12594

  Excellent investment or owner-occupied opportunity! This unique three-family property is comprised of two separate houses on one lot, offering flexibility and income. The front house features two units: a spacious upper unit with 3 bedrooms, an eat-in kitchen/family room, and 1 renovated new full bath, plus a separate 1-bedroom, 1-bath apartment on the lower level. The garage is currently rented,

  Antoinetta Carino Tag Realty & Property Mang

  804-806 Berkshire Rd Unit 806, Wingdale, NY 12594
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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,

  Adam Hade Compass Greater NY, LLC

  0 New York 22, Dover Plains, NY 12522
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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 Hillside Realty & Development

  149 Johnson Rd, Wingdale, NY 12594
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  /12

  $150,000

  • 3 Beds
  • 2 Baths
  • 980 Sq Ft

  63 Sasso Ln, Wingdale, NY 12594

  Walking Distance to Metro North Railroad, here is your chance to own a charming 3-bedroom, 2-full bathroom mobile home in tight-knit Wingdale Village. The screened in front porch leads to an open concept living room/kitchen combo - perfect for entertaining! This move-in ready home is waiting for you!!

  Michael Herman McGrath Realty Inc

  63 Sasso Ln, Wingdale, NY 12594
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  /40

  $325,000 Coming Soon

  • 3 Beds
  • 1 Bath
  • 1,057 Sq Ft

  16 Birch Hill Ln, Kent, CT 06757

  Cozy three-bedroom ranch on quiet private road. Direct frontage on the scenic Housatonic River. Sip your morning coffee on the private covered rear patio. View the fall foliage and listen to the relaxing sounds of the river. Would be a perfect setting for those who work from home. Private fenced in back yard perfect for pets to play. Just a short drive from the wonderful Kent Town Center with its

  Steve Triebe Scalzo Real Estate

  16 Birch Hill Ln, Kent, CT 06757
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  /19

  $340,000

  • 2 Beds
  • 1 Bath
  • 1,328 Sq Ft

  32 Cedar Ln, Wingdale, NY 12594

  Ranch style home on 1 acre. Mother-daughter potential. Full basement with own entrance. Large living room w/ bow window. Huge sunroom on back of home. Full bathroom was just renovated. 4 year old Heated 48x36 ft kayak pool w/ full deck, custom furniture, safety stairs & transferable warranty. New roof last year. New front porch. Newer exterior paint & water pressure tank in well. Large fenced

  Christopher Acken BHHS Hudson Valley Properties

  32 Cedar Ln, Wingdale, NY 12594
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  /35

  $1,175,000

  • 3 Beds
  • 2.5 Baths
  • 2,584 Sq Ft

  46 Spooner Hill Rd, South Kent, CT 06785

  Overlooking neighboring pastureland and set on 5+ private acres with a small pond, this three-bedroom cottage is rich in charm and character. A gracious foyer welcomes you into a sitting room with fireplace and built-ins, and an adjacent formal dining room framed by handsome casement windows. The spacious kitchen offers a center island and sunny breakfast area, opening seamlessly to an outdoor

  Steve Pener William Pitt Sotheby's Int'l

  46 Spooner Hill Rd, South Kent, CT 06785
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  /42

  $409,000

  • 3 Beds
  • 1 Bath
  • 1,012 Sq Ft

  113 Dog Tail Corners Rd, Wingdale, NY 12594

  This is an overbuilt charming brick house that can easily be expanded. Look through double windows to an amazing view across the street. In Living room and Kitchen, tongue- and- groove knotty pine from ceiling to floor, brick fireplace in living room will keep the house cozy day/night. Kitchen has knotty-pine cabinets. Park your car (electric garage door) and walk through basement to upstairs and

  Tela Cook McGrath Realty Inc

  113 Dog Tail Corners Rd, Wingdale, NY 12594
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  /25

  $279,000

  • Land
  • 5.46 Acres
  • $51,099 per Acre

  41 Long River Rd, Sherman, CT 06784

  This exceptional 5.46-acre parcel, perfectly positioned on Long River Road, is the largest homesite in the private community of River Oaks Country Club. The lightly wooded setting offers privacy and a natural backdrop for your custom residence with potential for sweeping long views that capture the beauty of the Berkshire foothills. Club River Oaks provides access to world-class amenities,

  Donna Kennedy Compass Connecticut, LLC

  41 Long River Rd, Sherman, CT 06784
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  /41

  $548,000

  • 3 Beds
  • 2 Baths
  • 1,852 Sq Ft

  503 Chestnut Ridge Rd, Dover Plains, NY 12522

  Escape to your own private sanctuary on two serene acres in the town of Unionvale. This charming oversized ranch home offers the perfect blend of comfort and nature, featuring a cleared, landscaped backyard ideal for gardening or peaceful afternoons, bordered by partly wooded grounds for ultimate privacy. Inside, the warmth of hardwood floors and a wood-burning stove in the dining area creates an

  Tamara LaBarbera Howard Hanna Rand Realty

  503 Chestnut Ridge Rd, Dover Plains, NY 12522
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  /41

  $460,000

  • 3 Beds
  • 2 Baths
  • 2,230 Sq Ft

  487 Chestnut Ridge Rd, Dover Plains, NY 12522

  Located in Dover Plains, this charming 3-bedroom, 2-bath Colonial offers 2,230 sq. ft. of living space on a 1.27-acre corner lot and includes a detached 2-car garage. Inside, you’ll find an inviting open-concept layout. The main level is perfect for entertaining or everyday living and features a spacious living room with hardwood floors, a large dining room that flows seamlessly to an eat-in

  Robert Washburn RE/MAX Ace Realty

  487 Chestnut Ridge Rd, Dover Plains, NY 12522
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  /9

  $241,581

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft

  93 Scott Dr, Dover Plains, NY 12522

  This is a 55+ Community -Ranch Style home with 3BR and 2Bath. Wonderful community with a Clubhouse and Pool. Also in the process of adding a wood deck for outdoor relaxation. Central Air, propane heating. Double-insulated to keep heating expenses low. Close to Sharon, Ct hospital, grocery shopping, etc.This community offers organized gatherings and events during the year for holidays, etc.

  DOROTA LASOTA-LOPEZ Century 21 Alliance Realty Grp

  93 Scott Dr, Dover Plains, NY 12522
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  /50

  $1,399,999

  • 6 Beds
  • 4.5 Baths
  • 4,200 Sq Ft

  57 Cedar Berry Ln, Dover Plains, NY 12522

  Just 90 miles from New York City, at the end of a winding, tree-lined drive, a world unfolds where time slows down, and life takes on a different rhythm. This is the Hudson Valley escape you’ve been waiting for. A custom-built home with detached workshop on nearly five private acres, where every detail was designed to bring comfort, inspiration, and beauty into daily living. The moment you

  Lindsay Stevens eXp Realty

  57 Cedar Berry Ln, Dover Plains, NY 12522
• 

  

  /22

  $389,000

  • 5 Beds
  • 2 Baths
  • 1,272 Sq Ft

  14 Dover Furnace Rd, Dover Plains, NY 12522

  Charming Five-Bedroom Home for Sale – 14 Dover Furnace Road, Dover Plains Welcome to this cozy five-bedroom, two-bath home featuring a spacious garage and a generously sized yard, perfect for outdoor enjoyment. The property has been thoughtfully updated with new gutters, new siding, central air conditioning, and a new propane boiler. Many repairs and improvements have already been completed,

  James Garcia Coldwell Banker Realty

  14 Dover Furnace Rd, Dover Plains, NY 12522
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  /11

  $175,000

  • 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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  /2

  $97,000

  • Land
  • 3.3 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

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