Dutchess, NY Homes

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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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  /9

  $950 per month

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

  34 Railroad St Unit 6, Dover Plains, NY 12522

  Property Id: 1408128This small, cozy 1 bdrm apt. has been thoroughly rehabbed and freshly painted. It has direct step down access off designated parking spot.It features ceramic tile floor throughout with 1 large LR window, 1 bedroom skylight, and 3 electric baseboard heaters.The BDRM measures 9½'x 11½'. Total sq footage of apt is 368.?Gaby's Deli on site for

  34 Railroad St Unit 6, Dover Plains, NY 12522
• 

  $315,000 Sold Aug 06, 2025

  • 1,135 Sq Ft
  • $278/SF
  • 31 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1970

  30 Lake Ellis Rd, Wingdale, NY 12594

  This bright and inviting 3-bedroom, 1.5-bath ranch is the kind of home that’s becoming harder to find—a well-maintained, move-in ready property with a smart layout, modern touches, and room to grow.Set just 7 minutes from the train and town center, this peaceful retreat offers the best of both worlds: quiet country charm with quick access to shopping, dining, and transit. You’re only 15

  Alex Mashkin Keller Williams Realty Partner

  30 Lake Ellis Rd, Wingdale, NY 12594
• 

  Est $514,158 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,101 Sq Ft

  25 Temby Dr, Dover Plains, NY 12522

  25 Temby Dr, Dover Plains, NY 12522
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  /41

  $435,000 Pending

  • 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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  /11

  $2,000 per month

  • 2 Beds
  • 1 Bath
  • 936 Sq Ft
  • House for Rent

  39 Webatuck Rd, Wingdale, NY 12594

  Stunningly restored home in the charming neighborhood of Webatuck, only 90 minutes from NYC and a short drive from the local Metro North. Perfect for weekend getaways or full time residence. Situated amongst numerous activities and entertainment such as hiking nearby trails, whitewater rafting on the Housatonic River, shopping in Kent CT, cycling the HV Rail Trail, and skiing at nearby Mohawk

  Andrew Stewart Gillian Stewart Real Estate

  39 Webatuck Rd, Wingdale, NY 12594
• 

  $465,000 Sold Aug 01, 2025

  • 1,750 Sq Ft
  • $266/SF
  • 19 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2021

  268 Lime Kiln Rd, Dover Plains, NY 12522

  Welcome to this beautifully maintained, newly built raised ranch sitting on one flat acre in a quiet country setting! Enjoy an open kitchen, dining and living room area perfect for entertaining with 2 full bathrooms upstairs. Downstairs is a finished bonus room with a half bath and a Lopi pellet stove. The laundry room is kept in closed closet doors next to the 2 car garage door with beautiful

  Jacqueline Redahan Century 21 Alliance Realty Grp

  268 Lime Kiln Rd, Dover Plains, NY 12522
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  Est $378,848 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft

  1512 Route 343, Dover Plains, NY 12522

  1512 Route 343, Dover Plains, NY 12522
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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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  /20

  $1,800 per month

  • 2 Beds
  • 1 Bath
  • 1,050 Sq Ft
  • Apartment for Rent

  43 Highview Rd, Dover Plains, NY 12522

  Country living, wildlife and a big, usable back yard are just some of the benefits of this 2 bedroom apartment in Dover Plains. Feel right at home with a large Living Room that can be divided into living and dining areas with hardwood floors and a beautiful, stone fireplace to heat the whole house in winter. The Galley Kitchen provides a full-size compliment of storage cabinets, a pantry closet

  Judy Albert BHHS Hudson Valley Properties

  43 Highview Rd, Dover Plains, NY 12522
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  $1,300,000 Sold Jul 31, 2025

  • 3,544 Sq Ft
  • $367/SF
  • 156 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 2002

  175 Kent Rd, Kent, CT 06757

  Secluded Country Estate with Modern Amenities Nestled on over 11 acres in the charming town of Kent, CT, this beautifully renovated country home, built in 2002, offers the perfect blend of rustic charm and contemporary elegance. The spacious interior boasts a newly renovated country kitchen, ideal for entertaining, and extensive renovations throughout, including new floors, fresh paint inside

  John Engel Douglas Elliman of Connecticut

  175 Kent Rd, Kent, CT 06757
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  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 924 Sq Ft

  37 Mallard Way, Dover Plains, NY 12522

  37 Mallard Way, 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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  /37

  $3,200 per month

  • 3 Beds
  • 2 Baths
  • 1,674 Sq Ft
  • House for Rent

  286 Cricket Hill Rd, Dover Plains, NY 12522

  Discover the perfect blend of comfort and countryside charm in this delightful home nestled in the heart of Dover Plains. Set on a beautifully maintained, expansive yard, this property offers ample space for relaxation and outdoor activities. The house features three well-appointed bedrooms and two full bathrooms, providing ample space for families or those seeking extra room. Enjoy summer

  Uzziel Abrigo eXp Realty

  286 Cricket Hill Rd, Dover Plains, NY 12522
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  $550,000 Sold Jul 29, 2025

  • 1,960 Sq Ft
  • $281/SF
  • 86 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2019

  46 Peaceable Way, Dover Plains, NY 12522

  Welcome to this beautiful, move-in ready one-level Ranch Home with an open floor plan! At just 6 years young and fully handicapped accessible, it’s located on a quiet cul-de-sac with breathtaking mountain views. The spacious, unfinished basement was built with "Superior Walls" and offers endless possibilities for expansion. The primary bedroom suite comfortably accommodates a king-size bed and

  Laura Fasciglione Keller Williams Realty Partner

  46 Peaceable Way, Dover Plains, NY 12522
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  Not Listed For Sale

  139 Sheldon Rd, Wingdale, NY 12594

  139 Sheldon Rd, Wingdale, NY 12594
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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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  /7

  $2,150 per month

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft
  • Apartment for Rent

  85 Hutchinson Ave Unit c, Wingdale, NY 12594

  Come view this beautifully renovated 2 bedroom 1 bathroom apartment with plenty of storage. This rental includes a private deck and assigned parking for up to two cars; and is close to everything, including train, shops, restaurants, outdoor attractions like Thunder Ridge Mountain, and schools. Heat and hot water included in the monthly rent. -

  David Cebel Iconik Residential LLC

  85 Hutchinson Ave Unit c, Wingdale, NY 12594
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  $380,000 Sold Jul 24, 2025

  • 1,588 Sq Ft
  • $239/SF
  • 31 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1960

  37 Rural Ave, Wingdale, NY 12594

  Located in the hamlet of Wingdale, this 3 bedroom, 2 bath home sits just minutes from the Metro-North station, nearby hiking trails and the shops and cafe's of Pawling. a spacious living room with hardwood floors opens directly into the kitchen, which boasts stone countertops, a subway-tile backsplash, a stainless-steel undermount sink and a bar-height counter for casual meals. The adjoining

  Jill Rose Houlihan Lawrence Inc.

  37 Rural Ave, Wingdale, NY 12594
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  Est $501,803 Not Listed For Sale

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

  6 Jordyn Ln, Dover Plains, NY 12522

  6 Jordyn Ln, Dover Plains, NY 12522
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  /39

  $575,000 Open Sun 12PM - 3PM

  • 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! Total acreage is 1.13 - Sellers are INCLUDING an adjoining .48 lot with Two Huge Detached Garages built in 2015, 40 X 28 and 24 X 24! Taxes and acreage for both lots are combined. Let's begin with the house. Inviting home was completely renovated in 2002 and expanded with a huge second floor primary suite.

  Lisa Liffland McGrath Realty Inc

  283 Johnson Rd, Wingdale, NY 12594
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  /24

  $3,800 per month

  • 3 Beds
  • 2.5 Baths
  • 2,229 Sq Ft
  • Apartment for Rent

  921 W Dover Rd, Pawling, NY 12564

  ALL INCLUSIVE RENTAL! All utilities and services are included. This 3-bedroom, 2.5 bathroom no-step main floor apartment is now available. Consisting of the whole main level of a beautiful, custom quality built ranch home and nestled on 8+ private acres, this apartment is 2200+ square feet! This modern house boasts a beautiful and open floor plan. A chef's kitchen has extensive granite counters,

  Joyce Brennan-Zolnik BHHS Hudson Valley Properties

  921 W Dover Rd, Pawling, NY 12564
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  $410,000 Sold Jul 24, 2025

  • 1,400 Sq Ft
  • $293/SF
  • 34 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1960

  11 Birch Terrace, Pawling, NY 12564

  Welcome to Pawling Lake Estates - a private lake community about 10 minutes outside the Village of Pawling. This adorable cozy Cape is located on a dead-end road. Has 2 bedrooms but can easily live like a 3-bedroom home. Main level has eat in kitchen with breakfast nook, cozy living room with big bay window. 2 Bedrooms and a main bath. Doors in kitchen that lead out to a nice size deck

  Teddie Leonaggeo McGrath Realty Inc

  11 Birch Terrace, Pawling, NY 12564
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  Est $175,966 Not Listed For Sale

  • 4 Beds

  7 River Bend Ln, Sherman, CT 06784

  7 River Bend Ln, Sherman, CT 06784
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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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  $105,000 Sold Jul 19, 2025

  • 980 Sq Ft
  • $107/SF
  • 106 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1978

  70 Sasso Ln, Wingdale, NY 12594

  Turn key Living in a Fully Renovated Home!Step into this beautifully renovated home, where comfort meets convenience in a move-in-ready space! Every detail has been upgraded, from the brand-new flooring to the newer appliances, ensuring modern functionality throughout.The spacious living room invites you in with a cozy wood-burning fireplace, perfect for chilly evenings, while the

  Tela Cook McGrath Realty Inc

  70 Sasso Ln, Wingdale, NY 12594
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  Est $610,594 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,056 Sq Ft

  10 Evans Hill Rd, Sherman, CT 06784

  10 Evans Hill Rd, 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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  $430,000 Sold Jul 18, 2025

  • 1,844 Sq Ft
  • $233/SF
  • 36 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1961

  41 Hillside Ave, Wingdale, NY 12594

  LET'S GO! Welcome to 41 Hillside Ave, a lovely 3 bedroom ranch styled home located directly in the middle of the charming Villages of Dover Plains and Pawling, in the quaint hamlet of Wingdale, with the conveniency of the Metro-North Train Station only a minute or two south on Route 22, as well as Boyce Park, the Dover Library, and Wingdale Elementary School literally a stone's throw away,

  Reid McGrath McGrath Realty Inc

  41 Hillside Ave, Wingdale, NY 12594
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  Est $848,430 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,925 Sq Ft

  25 Smoke Ridge Dr, Sherman, CT 06784

  25 Smoke Ridge Dr, Sherman, CT 06784
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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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  $650,000 Sold Jul 17, 2025

  • 2,000 Sq Ft
  • $325/SF
  • 30 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1820

  80-82 Connecticut 55, Sherman, CT 06784

  Located just steps from the Appalachian Trail and the New York state line, this historic 1820 Colonial and guest cottage offer a unique blend of historic craftsmanship, character, and charm. Set on 8.38 acres in northwest Sherman, the property showcases many period details - from original stone fireplaces and custom built-ins to handsome stone walls, patios, steps, and terracing. The main

  Irit Granger William Pitt Sotheby's Int'l

  80-82 Connecticut 55, Sherman, CT 06784
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  Est $903,992 Not Listed For Sale

  • 4 Beds

  2 Anderson Rd E, Sherman, CT 06784

  2 Anderson Rd E, 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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  $345,000 Sold Jul 09, 2025

  • 900 Sq Ft
  • $383/SF
  • 26 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1990

  88 Lakeview Dr, Pawling, NY 12564

  Charming Cottage in Private Community of Pawling Lake Estates. Adjacent to the Appalachian Trail and the Great Swamp of Putnam and Dutchess County, sitting atop the West Mountain State Park you will find our Community, a Hidden Gem. Privacy, Peace and Tranquility abound in this Natural Setting. This Home has been lovingly cared for and updated with Replacement Windows, Vinyl Siding, Gutter Guards

  Martha Woodhouse Howard Hanna Rand Realty

  88 Lakeview Dr, Pawling, NY 12564
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  Est $624,506 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,556 Sq Ft

  26 Anderson Rd, Sherman, CT 06784

  26 Anderson Rd, Sherman, CT 06784
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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
• 

  $519,000 Sold Jul 08, 2025

  • 1,540 Sq Ft
  • $337/SF
  • 76 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1962

  476 Chestnut Ridge Rd, Dover Plains, NY 12522

  Escape to the serenity of the countryside with this beautifully updated California-style ranch, set on a private and picturesque 2.2-acre property. Designed for both comfort and style, this 3 bedroom home features a 32x16 in-ground pool and ample space for horses, with open fields extending beyond the backyard. Inside, gleaming hardwood floors flow through most of the living space, complementing

  Emelisa Mendoza RE/MAX Town & Country

  476 Chestnut Ridge Rd, Dover Plains, NY 12522
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  Est $592,517 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,642 Sq Ft

  28 Anderson Rd, Sherman, CT 06784

  28 Anderson Rd, Sherman, CT 06784
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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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