Wingdale, NY Homes

/20
$379,900
- 3 Beds
- 1.5 Baths
- 1,520 Sq Ft
10 Raymond Ave, Dover Plains, NY 12522

Nestled at the end of the cul de sac this charming home is being offered for the first since 1995.What a fabulous home this is. There are exquisite hard wood floors throughout except for the bathrooms that have a tile floor.This country home is in outstanding condition. Echa room presents distinct qualities. The main living level has an eat in kitchen that opens up into a great room with

Larry Havens

Havens Real Estate

(845) 493-2818

10 Raymond Ave, Dover Plains, NY 12522
/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
$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

/62
Est $876,664 Not Listed For Sale
- 4 Beds
- 2 Baths
- 2,496 Sq Ft
158 Lake Ellis Rd, Wingdale, NY 12594

158 Lake Ellis Rd, Wingdale, NY 12594

/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 complexation

Larry Havens

Havens Real Estate

(845) 506-8855

39 Maple Ln, Dover Plains, NY 12522
/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
$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

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

/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
/11
$1,700 per month
- 1 Bed
- 1 Bath
- 700 Sq Ft
- Apartment for Rent
23 Stephen Rd, Dover Plains, NY 12522

Cozy One Bedroom, one bath apartment - bottom part of home, your own entrance. Located on a Cul-de-sac. Walk into your Living Room, Kitchen combo. Kitchen has stainless steel appliances. Lots of cabinets and a pantry. Bedroom has lots of shelving and closet space with washer and dryer. Full bathroom with shower. Wi-Fi is included. Electric included and the heat is electric. Ceiling Fans.

Teddie Leonaggeo McGrath Realty Inc

23 Stephen Rd, Dover Plains, NY 12522
$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

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

/35
$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
/19
$2,000 per month
- 2 Beds
- 2 Baths
- 1,296 Sq Ft
- Apartment for Rent
1531 Route 22 Unit E, Wingdale, NY 12594

Welcome to this comfortable and conveniently located 2 bedroom Apartment w/both front & back entrances. Bright open concept one level living has an eat in kitchen w/tile floor & recessed lighting, large living room with coat closet, and an additional spacious back room which can be used for multiple uses (back room has a door out to back). Spacious bedroom with renovated full bath & large closet,

Diana Cirocco Coldwell Banker Realty

1531 Route 22 Unit E, Wingdale, NY 12594
$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

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

/34
$650,000
- 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
/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
$485,000 Sold Jul 02, 2025
- 1,976 Sq Ft
- $245/SF
- 52 Days On Market
- 3 Beds
- 3 Baths
- Built 1909
3211 Route 22, Dover Plains, NY 12522

Discover this charming colonial-style 2-family home! Live in one apartment while earning income from the second unit, or if you’re an investor, acquire a property with positive cash flow. Both apartments have been completely renovated in 2024, featuring new windows, gutters, siding, exterior stairs, hardwood floors, 1st level kitchen with granite countertops, and a new ductless A/C system on the

Luis Diaz Century 21 Alliance Realty Grp

3211 Route 22, Dover Plains, NY 12522

Not Listed For Sale
139 Sheldon Rd, Wingdale, NY 12594

139 Sheldon Rd, Wingdale, NY 12594

/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
/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
$325,000 Sold Jun 30, 2025
- 1,362 Sq Ft
- $239/SF
- 43 Days On Market
- 2 Beds
- 1 Bath
- Built 1997
26 Lilac Dr, Wingdale, NY 12594

Charming 2-Bedroom, 1-Bathroom Raised Ranch with Bonus Office, pool & large Deck!Welcome to this cozy raised ranch, where comfort and flexibility meet! With 2 bedrooms that live like 3, plus an additional office space, this home offers plenty of room to spread out. Whether you need extra sleeping space, a home office, or a playroom, this home has you covered.The living area is

Crystal Neceda Briante Realty Group, LLC

26 Lilac Dr, Wingdale, NY 12594

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

/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
$450,000 Sold Jun 27, 2025
- 1,644 Sq Ft
- $274/SF
- 42 Days On Market
- 3 Beds
- 2 Baths
- Built 1963
24 Buttonwood Rd, Dover Plains, NY 12522

Looking for the home of your dreams?This property boasts over 10 acres of expansive land with breathtaking mountain views, a serene pond, and all the privacy you could ask for—all within just 10 minutes of Metro North for easy commuting. The possibilities here are endless!While the house may need some TLC, a little love will go a long way. Recent updates include newer windows,

Melanie Boucos Coldwell Banker Realty

24 Buttonwood Rd, Dover Plains, NY 12522

Est $175,966 Not Listed For Sale
- 4 Beds
7 River Bend Ln, Sherman, CT 06784

7 River Bend Ln, Sherman, CT 06784

/47
$749,900
- 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
$815,000 Sold Jun 26, 2025
- 3,292 Sq Ft
- $248/SF
- 11 Days On Market
- 3 Beds
- 3.5 Baths
- Built 1930
50 N Chippawalla Rd, Wingdale, NY 12594

Have you ever thought to yourself "Someday I'm going to have my own farm or a private retreat upstate..." Well, NOW is your opportunity to own your own PRIVATE 8 ACRE RETREAT in the highly desirable Mid-Hudson Valley! This complex has boundless possibilities including TWO living quarters: A Cape Cod Style Main Home featuring 2 large bedrooms, 2 baths, and a kitchen with so much natural light

CHRISTOPHER FILANGERI BHHS Hudson Valley Properties

50 N Chippawalla Rd, Wingdale, NY 12594

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

/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
$805,000 Sold Jun 13, 2025
- Land
- 85 Acres
- $9,507 per Acre
- 82 Days On Market
0 Chestnut Ridge Rd Unit KEY823877, Dover, NY 12522

Located on Chestnut Ridge Road, seven miles from the Village of Millbrook, this exceptional and unique 84+ acre land property offers not only great topographic diversity but also has ready approved subdivisions. It consists of two separate tax parcels, complementing each other as a whole or separately. The first 15+ acre lot is accessible with its own long driveway up to a large hay field with

Marie-Laure Collins Compass Greater NY, LLC

0 Chestnut Ridge Rd Unit KEY823877, Dover, NY 12522

Est $850,654 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

/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
$1,200,000 Sold Jun 10, 2025
- 5,532 Sq Ft
- $217/SF
- 37 Days On Market
- 6 Beds
- 5 Baths
- Built 2009
206-208 Dog Tail Corners Rd, Wingdale, NY 12594

Have you dreamed of owning an incredibly special and unique property? Well, dream no more, now is your chance! A winding driveway off of a small country road, brings you to a custom-built, private, 6-bedroom, 5-bath, light-filled contemporary home with a 2- bedroom guest house, on 7.2+ acres that enjoys 550 feet of frontage on the beautiful Tenmile River, as well as a pond, perfect for swimming,

Ann Stettner Neil Charles Real Estate, LLC

206-208 Dog Tail Corners Rd, Wingdale, NY 12594

Est $903,992 Not Listed For Sale
- 4 Beds
2 Anderson Rd E, Sherman, CT 06784

2 Anderson Rd E, Sherman, CT 06784

/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
$205,000 Sold Jun 05, 2025
- 1,048 Sq Ft
- $196/SF
- 68 Days On Market
- 2 Beds
- 2 Baths
- Built 1992
126 Reagans Mill Rd, Wingdale, NY 12594

Welcome to 126 Reagan Mills Rd a well cared for home offering one level living. This home boasts an open-concept layout, allowing for seamless flow between the spacious living room, dining area, and kitchen. There are 2 spacious bedrooms along with an additional room in the back of the home. The additional room is perfect for a home office. The home has forced air oil heat and central air.

Mark Snyder eXp Realty

126 Reagans Mill Rd, Wingdale, NY 12594

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

/48
$799,900 Open Sun 11:30AM - 1:30PM
- 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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