Dover, NY Homes

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  /46

  $815,000

  • 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

  

  Judith 'Judy' Albert

  BHHS Hudson Valley Properties

  (845) 412-9430

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

  

  

  /23

  $3,100 Per Month

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft
  • House for Rent

  2831 Pleasant Ridge Rd, Wingdale, NY 12594

  A-Frame style 3-bedroom, 2 full bath home upper level offering privacy and an open floor plan. Spacious kitchen with granite counters and features stainless steel appliances, abundant cabinetry, and flows into the oversized living and dining areas. Two sliding glass doors lead to a large deck overlooking the front yard, perfect for relaxing or entertaining. Main level also includes hardwood

  

  Teddie Leonaggeo

  McGrath Realty Inc

  (845) 415-4562

  2831 Pleasant Ridge Rd, Wingdale, NY 12594
• 

  $549,000

  Sold Jan 28, 2026

  105 Sheldon Rd, Wingdale, NY 12594

  • 4 Beds
  • 3 Baths
  • 2,792 Sq Ft
  • Built 1996

  Last Sold Summary

  • $197/SF
  • 48 Days On Market

  Current Estimated Value $547,394

  Last Listing Agent Barbara Negro Century 21 Alliance Realty Grp

  105 Sheldon Rd, Wingdale, NY 12594
• 

  Est $552,595

  Not Listed For Sale

  8 Benson Ln, Dover Plains, NY 12522

  • 4 Beds
  • 2.5 Baths
  • 2,420 Sq Ft
  • Built 2004

  8 Benson Ln, Dover Plains, NY 12522

  Last Sold Summary

  • 5% Above List Price
  • $217/SF
  • 65 Days On Market

  • Last Sold Price $525,000
  • Mar 18, 2025

  Last Listing Agent Jackie Calhoun Coldwell Banker Realty
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  /30

  $440,000

  • 3 Beds
  • 3 Baths
  • 1,556 Sq Ft

  978 W Dover Rd, Pawling, NY 12564

  Welcome to 978 W Dover Road in Pawling, NY—where comfort, space, and scenic beauty come together effortlessly. This inviting home features 3 generously sized bedrooms, 3 full bathrooms, and a dedicated home office, making remote work both productive and enjoyable. The open-concept main level creates a seamless flow between living spaces, perfect for hosting gatherings or simply spending quality

  Regan Andrews Coldwell Banker Realty

  978 W Dover Rd, Pawling, NY 12564
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  /8

  $1,000 Per Month

  • 1 Bed
  • 1 Bath
  • 313 Sq Ft
  • Condo for Rent

  34 Railroad St Unit 11, Dover Plains, NY 12522

  Property Id: 1266681The apartment is on the backside of the property, and has small section of grassy yard. It was freshly renovated and painted. It features tile and T and G engineered floor. There are 3 new East-facing windows and 3 electric baseboard heaters. The BDRM is ~8' x 11'. On-site Property Manager and Bldg Super.A deli is on site for your convenience. 500'

  (845) 605-7915

  34 Railroad St Unit 11, Dover Plains, NY 12522
• 

  $395,000

  Sold Apr 17, 2026

  3057 Pleasant Ridge Rd, Wingdale, NY 12594

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft
  • Built 1964

  Last Sold Summary

  • 4% Below List Price
  • $411/SF
  • 78 Days On Market

  Current Estimated Value $397,398

  Last Listing Agent Richard Rennia Richard A. Rennia

  3057 Pleasant Ridge Rd, Wingdale, NY 12594
• 

  Est $524,494

  Not Listed For Sale

  6 Jordyn Ln, Dover Plains, NY 12522

  • 3 Beds
  • 3 Baths
  • 1,943 Sq Ft
  • Built 2023

  6 Jordyn Ln, Dover Plains, NY 12522

  Last Sold Summary

  • 10% Above List Price
  • $244/SF
  • 96 Days On Market

  • Last Sold Price $475,000
  • Nov 30, 2023

  Last Listing Agent Stacey Cronin Houlihan Lawrence Inc.
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  /22

  $449,000

  Pending

  • 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
• 

  /2

  $950 - $1,150

  Total Monthly Price

  • Studio - 1 Bed
  • 1 Bath
  • 200 Sq Ft
  • Condo for Rent

  31 Wing Ave, Dover Plains, NY 12522

  One bedroom apartment. No pets. No Smoking. Background/credit check for each applicant ($20 fee). Hot water, garbage collection, snow removal included. Must have credit score of 550 or higher.

  31 Wing Ave, Dover Plains, NY 12522
• 

  $383,000

  Sold Mar 13, 2026

  105 S Nellie Hill Rd, Dover Plains, NY 12522

  • 3 Beds
  • 2 Baths
  • 1,523 Sq Ft
  • Built 1952

  Last Sold Summary

  • 18% Below List Price
  • $251/SF
  • 184 Days On Market

  Current Estimated Value $382,326

  Last Listing Agent Larry Havens Havens Real Estate

  105 S Nellie Hill Rd, Dover Plains, NY 12522
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  Not Listed For Sale

  0 Drovers Ln Unit KEYM413718, Dover, NY 12522

  0 Drovers Ln Unit KEYM413718, Dover, NY 12522

  Last Sold Summary

  • 233 Days On Market

  • Last Sold Price $75,000
  • Oct 17, 2023

  Last Listing Agent Mark Snyder eXp Realty
• 

  

  /23

  $450,000

  $49K PRICE DROP

  • 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

  105 Sand Hill Rd, Dover Plains, NY 12522
• 

  /2

  $950 - $1,150

  Total Monthly Price

  • Studio - 1 Bed
  • 1 Bath
  • 200 Sq Ft
  • Condo for Rent

  31 Wing Ave, Dover Plains, NY 12522

  One bedroom apartment. No pets. No Smoking. Background/credit check for each applicant ($20 fee). Hot water, garbage collection, snow removal included. Must have credit score of 550 or higher.

  31 Wing Ave, Dover Plains, NY 12522
• 

  $365,000

  Sold May 01, 2026

  106 Johnson Rd, Wingdale, NY 12594

  • 3 Beds
  • 1 Bath
  • 1,788 Sq Ft
  • Built 1970

  Last Sold Summary

  • 9% Below List Price
  • $204/SF
  • 24 Days On Market

  Current Estimated Value $396,024

  Last Listing Agent Teddie Leonaggeo McGrath Realty Inc

  106 Johnson Rd, Wingdale, NY 12594
• 

  

  /16

  Est $695,587

  Not Listed For Sale

  565 Poplar Hill Rd, Dover Plains, NY 12522

  565 Poplar Hill Rd, Dover Plains, NY 12522

  Last Sold Summary

  • 1% Below List Price
  • 106 Days On Market

  • Last Sold Price $700,000
  • Mar 04, 2025

  Last Listing Agent Michael Tellerday Houlihan Lawrence, Inc.
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  /38

  $400,000

  Pending

  • 2 Beds
  • 2 Baths
  • 1,410 Sq Ft

  63 Hoags Corner Rd, Wingdale, NY 12594

  The most charming Cape Cod–styled home with a flexible layout spanning three floors is set on nearly an acre of mostly cleared land, framed by a picturesque mountain backdrop and ready to welcome its next owner. A sun-drenched covered front porch greets you on arrival, enclosed by windows on all three sides to create a truly delightful sitting room. Inside, the home opens to a nicely sized living

  Claudia Jiskra McGrath Realty Inc

  63 Hoags Corner Rd, Wingdale, NY 12594
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  /10

  $15,000 Per Month

  • 3 Beds
  • 4 Baths
  • 4,043 Sq Ft
  • House for Rent

  209 Cricket Hill Rd, Dover Plains, NY 12522

  Seasonal Equestrian Facility Rental! Experience country living with a touch of luxury at 209 Cricket Hill Rd, Dover Plains,NY. This beautiful 3 bed/4 bath log home sits atop 55+ scenic acres, offering privacy, sweeping views, and the perfect retreat. The property features an 8-stall barn with tack, indoor and outdoor wash stalls/grooming stalls, hay loft, and a studio/1 bath apartment located in

  Alexandra Teetor Keller Williams NY Realty

  209 Cricket Hill Rd, Dover Plains, NY 12522
• 

  $370,000

  Sold Feb 02, 2026

  42 Lime Kiln Rd, Dover Plains, NY 12522

  • 3 Beds
  • 2 Baths
  • 1,397 Sq Ft
  • Built 1977

  Last Sold Summary

  • 13% Below List Price
  • $265/SF
  • 201 Days On Market

  Current Estimated Value $378,374

  Last Listing Agent Susan Todd BHHS Hudson Valley Properties

  42 Lime Kiln Rd, Dover Plains, NY 12522
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  Not Listed For Sale

  116 Bluebird Way, Dover Plains, NY 12522

  • 2 Beds
  • 2 Baths
  • 924 Sq Ft
  • Built 1985

  116 Bluebird Way, Dover Plains, NY 12522

  Last Sold Summary

  • $96/SF
  • 112 Days On Market

  • Last Sold Price $89,000
  • Jan 31, 2025

  Last Listing Agent Richard Rennia Richard A. Rennia
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  /26

  $398,800

  Pending

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

  840 Old State Route 22, Dover Plains, NY 12522

  Welcome to this beautifully maintained three-bedroom home nestled in the heart of Dover. Offering the perfect blend of comfort and convenience, this property is ideal for both full-time living and a peaceful retreat. Step inside to find a bright and inviting layout featuring a spacious living area, a well-appointed kitchen, and a dining space perfect for everyday living or entertaining. The three

  Michael Lund Corcoran Country Living

  840 Old State Route 22, Dover Plains, NY 12522
• 

  

  /20

  $375,000

  Sold Dec 31, 2025

  39 Maple Ln, Dover Plains, NY 12522

  • 3 Beds
  • 1.5 Baths
  • 1,628 Sq Ft
  • Built 1970

  Last Sold Summary

  • 4% Above List Price
  • $230/SF
  • 132 Days On Market

  Current Estimated Value $381,760

  Last Listing Agent Larry Havens Havens Real Estate

  39 Maple Ln, Dover Plains, NY 12522
• 

  Est $465,907

  Not Listed For Sale

  31 White Oak Cir, Wingdale, NY 12594

  • 3 Beds
  • 2 Baths
  • 1,770 Sq Ft
  • Built 2000

  31 White Oak Cir, Wingdale, NY 12594

  Last Sold Summary

  • 8% Above List Price
  • $243/SF
  • 69 Days On Market

  • Last Sold Price $430,000
  • Jan 25, 2024

  Last Listing Agent Joann Perna Guardian Realty Center, LLC
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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
• 

  $410,000

  Sold Jul 24, 2025

  11 Birch Terrace, Pawling, NY 12564

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1960

  Last Sold Summary

  • 3% Above List Price
  • $293/SF
  • 34 Days On Market

  Current Estimated Value $416,167

  Last Listing Agent Teddie Leonaggeo McGrath Realty Inc

  11 Birch Terrace, Pawling, NY 12564
• 

  Est $406,535

  Not Listed For Sale

  317 Dog Tail Corners Rd, Wingdale, NY 12594

  • 3 Beds
  • 1.5 Baths
  • 1,572 Sq Ft
  • Built 1965

  317 Dog Tail Corners Rd, Wingdale, NY 12594

  Last Sold Summary

  • $258/SF
  • 21 Days On Market

  • Last Sold Price $405,000
  • Feb 07, 2025

  Last Listing Agent Jennifer Amicucci
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  /34

  $399,000

  $26K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,012 Sq Ft

  113 Dog Tail Corners Rd, Wingdale, NY 12594

  Located on 1.54 acres of scenic land, this charming overbuilt home has a perfect blend of comfort, privacy, and natural beauty. Enjoy open field views across the street from your living room, creating a peaceful backdrop for everyday living and relaxing evenings. The home features a warm and inviting layout, in the living room and kitchen, walls are tongue and groove knotty pine from ceiling to

  Tela Cook McGrath Realty Inc

  113 Dog Tail Corners Rd, Wingdale, NY 12594
• 

  $380,000

  Sold Jan 16, 2026

  9 Nicole Ln, Wingdale, NY 12594

  • 3 Beds
  • 1.5 Baths
  • 1,036 Sq Ft
  • Built 1998

  Last Sold Summary

  • 9% Above List Price
  • $367/SF
  • 19 Days On Market

  Current Estimated Value $376,076

  Last Listing Agent Claudia Jiskra McGrath Realty Inc

  9 Nicole Ln, Wingdale, NY 12594
• 

  Est $482,169

  Not Listed For Sale

  21 Hoyt Rd, Wingdale, NY 12594

  • 3 Beds
  • 2 Baths
  • 1,127 Sq Ft
  • Built 1966

  21 Hoyt Rd, Wingdale, NY 12594

  Last Sold Summary

  • 2% Above List Price
  • $421/SF
  • 27 Days On Market

  • Last Sold Price $475,000
  • Jan 06, 2025

  Last Listing Agent Clayton Livingston McGrath Premier Real Estate
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  /36

  $715,000

  • 3 Beds
  • 3.5 Baths
  • 3,629 Sq Ft

  921 W Dover Rd, Pawling, NY 12564

  A One-of-a-Kind Custom Ranch on Nearly 4 Private Acres. Discover exceptional space, quality, and versatility in this expansive custom-built 3+ bedroom ranch, perfectly tucked away in a serene country setting. Designed for comfort and flexibility, this home is ideal for extended family living, multi-generational needs, or a spacious mother-daughter layout. The main floor offers true single-level

  Joyce Brennan-Zolnik BHHS Hudson Valley Properties

  921 W Dover Rd, Pawling, NY 12564
• 

  $465,000

  Sold Aug 01, 2025

  268 Lime Kiln Rd, Dover Plains, NY 12522

  • 3 Beds
  • 2.5 Baths
  • 1,750 Sq Ft
  • Built 2021

  Last Sold Summary

  • $266/SF
  • 19 Days On Market

  Current Estimated Value $464,129

  Last Listing Agent Jacqueline Redahan Century 21 Alliance Realty Grp

  268 Lime Kiln Rd, Dover Plains, NY 12522
• 

  

  /62

  Est $783,262

  Not Listed For Sale

  158 Lake Ellis Rd, Wingdale, NY 12594

  • 4 Beds
  • 2 Baths
  • 2,496 Sq Ft
  • Built 1820

  158 Lake Ellis Rd, Wingdale, NY 12594

  Last Sold Summary

  • 8% Below List Price
  • $343/SF
  • 25 Days On Market

  • Last Sold Price $855,825
  • Jul 19, 2024

  Last Listing Agent Anthony D'Argenzio Houlihan Lawrence Inc.
• 

  

  /22

  $130,000

  Pending

  • 3 Beds
  • 2 Baths
  • 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
• 

  $435,000

  Sold Sep 29, 2025

  27 Cavelo Dr, Wingdale, NY 12594

  • 3 Beds
  • 3 Baths
  • 1,794 Sq Ft
  • Built 1974

  Last Sold Summary

  • $242/SF
  • 31 Days On Market

  Current Estimated Value $443,930

  Last Listing Agent Shannon Tully McGrath Realty Inc

  27 Cavelo Dr, Wingdale, NY 12594
• 

  Est $370,197

  Not Listed For Sale

  152 Weil Rd, Wingdale, NY 12594

  • 2 Beds
  • 1 Bath
  • 1,237 Sq Ft
  • Built 1940

  152 Weil Rd, Wingdale, NY 12594

  Last Sold Summary

  • 1% Above List Price
  • $295/SF
  • 78 Days On Market

  • Last Sold Price $365,000
  • Jan 10, 2025

  Last Listing Agent Vicki Reinach BHHS Hudson Valley Properties
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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
• 

  $550,000

  Sold Jul 29, 2025

  46 Peaceable Way, Dover Plains, NY 12522

  • 3 Beds
  • 2 Baths
  • 1,960 Sq Ft
  • Built 2019

  Last Sold Summary

  • 6% Below List Price
  • $281/SF
  • 86 Days On Market

  Current Estimated Value $565,935

  Last Listing Agent Laura Fasciglione Keller Williams Realty Partner

  46 Peaceable Way, Dover Plains, NY 12522
• 

  Est $557,237

  Not Listed For Sale

  32 Meadow Brook Ln, Wingdale, NY 12594

  • 3 Beds
  • 2.5 Baths
  • 2,350 Sq Ft
  • Built 2003

  32 Meadow Brook Ln, Wingdale, NY 12594

  Last Sold Summary

  • 3% Above List Price
  • $230/SF
  • 29 Days On Market

  • Last Sold Price $540,000
  • Sep 05, 2024

  Last Listing Agent Shannon Tully McGrath Realty Inc
• 

  

  /30

  $1,299,999

  $500K PRICE DROP

  • 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 Compass Greater NY LLC

  165 Duell Hollow Rd, Wingdale, NY 12594
• 

  $460,000

  Sold Dec 11, 2025

  26 Nicole Ln, Wingdale, NY 12594

  • 3 Beds
  • 2 Baths
  • 2,072 Sq Ft
  • Built 1999

  Last Sold Summary

  • 3% Above List Price
  • $222/SF
  • 18 Days On Market

  Current Estimated Value $476,231

  Last Listing Agent Andrea Rudkowski Closer Real Estate

  26 Nicole Ln, Wingdale, NY 12594

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