Dutchess, NY Homes

/44
$275,000
- 2 Beds
- 2 Baths
- 1,836 Sq Ft
3465 Route 22, Dover Plains, NY 12522

Experience serene country living at 3465 Route 22, Dover Plains, NY 12522! This spacious, well-maintained ranch-style home offers the perfect blend of comfort and style, set back from the road for privacy and boasting breathtaking panoramic views of the surrounding Hudson Valley landscape. Step inside to discover a bright and inviting living room, complete with a cozy fireplace—perfect for

Omar Harper

Epique Realty

(845) 599-0147

3465 Route 22, Dover Plains, NY 12522
/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
$325,000 Sold Aug 04, 2025
- 1,750 Sq Ft
- $186/SF
- 247 Days On Market
- 3 Beds
- 1 Bath
- Built 1881
214 Old Route 22, Wassaic, NY 12592

Looking for a house with character and the opportunity to make a little extra money? Look no further, this charming property offers a single family home accompanied by a detached garage apartment. Take a walk through the spacious screened in porch on the way inside to your warm and cozy kitchen, perfect for cooking all of those delicious holiday meals, which you can enjoy with loved ones in the

Samantha Davis BHHS Hudson Valley Properties

214 Old Route 22, Wassaic, NY 12592

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

/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
/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
$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

Est $507,658 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,946 Sq Ft
1402 Route 343, Washington, NY 12522

1402 Route 343, Washington, NY 12522

/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
/40
$6,000 per month
- 2 Beds
- 1.5 Baths
- 1,296 Sq Ft
- House for Rent
47 Johnson Rd, Kent, CT 06757

Embrace the art of living well at Poetess Place, a haven designed for writers, birders, and nature lovers, tucked away on a private riverfront perch in the heart of picturesque Kent, CT. This lovingly remodeled 3-bedroom cottage, each room adorned with queen-sized comfort, invites you into a world of warmth and serenity. Wake up to the soothing melody of the Housatonic River and be captivated by

Inna Agujen Coldwell Banker Realty

47 Johnson Rd, Kent, CT 06757
$700,000 Sold Jul 18, 2025
- 1,500 Sq Ft
- $467/SF
- 18 Days On Market
- 2 Beds
- 1.5 Baths
- Built 1930
620 Route 343, Millbrook, NY 12545

Introducing the Millbrook Farmhouse. This beautifully updated cedar shake farmhouse blends idyllic charm with modern upgrades on a landscaped one-acre parcel just minutes from the Village of Millbrook. Fully gut-renovated in 2015, every detail of the property was thoughtfully rebuilt, from the house and garage to the expansive landscaping. Extensive yard work—including tree removal and clearing

Kyle Irwin Corcoran Country Living

620 Route 343, Millbrook, NY 12545

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

/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
$440,000 Sold Jul 11, 2025
- 1,104 Sq Ft
- $399/SF
- 70 Days On Market
- 3 Beds
- 1 Bath
- Built 1962
53B Elizabeth St, Kent, CT 06757

**Discover Your Dream Home at 53B Elizabeth!** Step into comfort with this beautifully updated ranch featuring gorgeous hardwood floors, spacious bedrooms, and a remodeled bathroom. Enjoy the convenience of a new 2-car garage, expansive front porch, and upgraded systems throughout! Located just a short stroll from Kent Center School and Kent's Village District, you'll have dining, shopping, and

Leigh Ann Lengyel Clarke RE/MAX Heritage

53B Elizabeth St, Kent, CT 06757

Est $642,284 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 3,060 Sq Ft
1046 New York 343, Dover Plains, NY 12522

1046 New York 343, Dover Plains, NY 12522

/15
$215,000
- Land
- 9 Acres
- $23,395 per Acre
0 Kent Rd Unit 20252538, Amenia, NY 12592

Welcome to 9.19 acres of rolling meadow, offering breathtaking vistas of the Eastern Dutchess County countryside. Tucked away from the road, this peaceful and private setting provides the perfect canvas for your dream home.Whether you're envisioning a simple retreat, a working farm, or a lush garden oasis, this land supports a wide range of possibilities.Enjoy easy access to Metro-North,

Larry Havens

Havens Real Estate

(845) 442-1853

0 Kent Rd Unit 20252538, Amenia, NY 12592
$6,700,000 Sold Jul 10, 2025
- 7,632 Sq Ft
- $878/SF
- 736 Days On Market
- 5 Beds
- 4.5 Baths
- Built 1827
27 Macedonia Brook Rd, Kent, CT 06757

A truly rare opportunity to own “Dragonfly Farm”, one of the most unique estates in New England which has been featured in House & Garden and many architectural books. The estate compound began in the 1700s with the construction of the mill and the millkeeper's house (which now serves as the guest house). The Federal style stone house was added to the property in the early 19th century. In the

Stacey Matthews W. Raveis Lifestyles Realty

27 Macedonia Brook Rd, Kent, CT 06757

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

/11
$215,000
- Land
- 9 Acres
- $23,395 per Acre
0 Kent Rd Unit KEY882325, Amenia, NY 12592

9.19 versatile acres with remarkable vistas of the gorgeous Eastern Dutchess County countryside. At the moment you will have the ability to select a site for your dream home on this open rolling open meadow. Offering privacy and set well off the road the ideal homesite welcomes your vision and ingenuity.This parcel is currently being used as a hayfield; however, your horticultural and

Larry Havens

Havens Real Estate

(845) 439-2876

0 Kent Rd Unit KEY882325, Amenia, NY 12592
$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

/26
Est $348,470 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 1,152 Sq Ft
60 Willow Ln, Wassaic, NY 12592

60 Willow Ln, Wassaic, NY 12592

/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
$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
- 2 Beds
- 2 Baths
- 980 Sq Ft
198 Sinpatch Rd, Wassaic, NY 12592

198 Sinpatch Rd, Wassaic, NY 12592

/27
$1,150,000
- 2 Beds
- 1 Bath
- 1,216 Sq Ft
447 Butts Hollow Rd, Dover Plains, NY 12522

It seems to be a human instinct to define utopia as a garden, and this Millbrook property on Butts Hollow Road unequivocally deserves that designation. Not only gardens—which have been lovingly created and curated—but meadows and forest glens, falling water and meandering paths. Regardless of season, there is always something unexpected and lovely to greet you—a rippling sea of red poppies,

Candy Anderson Compass Greater NY, LLC

447 Butts Hollow 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 $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
$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 $1,262,690 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,866 Sq Ft
51 Elizabeth St, Kent, CT 06757

51 Elizabeth St, Kent, CT 06757

/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
$341,000 Sold Jun 18, 2025
- 1,552 Sq Ft
- $220/SF
- 23 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1900
208 Old Route 22, Wassaic, NY 12592

Beautifully renovated 3-bedroom, 1.5-bath Colonial featuring modern updates throughout. This stunning home boasts a brand-new kitchen with stainless steel appliances, updated bathrooms, and stylish finishes. Enjoy spacious living areas, and plenty of natural light. Move right in and make it yours!

Peter Grosso RE/MAX Integrity Leaders

208 Old Route 22, Wassaic, NY 12592

Est $301,666 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 1,232 Sq Ft
16 Elizabeth St Unit 12, Kent, CT 06757

16 Elizabeth St Unit 12, Kent, CT 06757

/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
$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

Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 6,251 Sq Ft
34 Macedonia Brook Rd, Kent, CT 06757

34 Macedonia Brook Rd, Kent, CT 06757

/30
$699,000 Pending
- 3 Beds
- 2.5 Baths
- 2,014 Sq Ft
6 Lee Cir, Kent, CT 06757

Welcome to 6 Lee Circle, a fully renovated Colonial in the desirable Saddle Ridge subdivision, just minutes from downtown Kent. This 3-bedroom, 2.5-bath home offers 2,014 sq ft of thoughtfully updated living space on a quiet cul-de-sac with incredible western views. The main level features a sun-filled living room with a wood-burning fireplace and picture windows overlooking the hillside. A

Brian Hastings Serhant Connecticut, LLC

6 Lee Cir, Kent, CT 06757
$285,000 Sold Jun 06, 2025
- 1,548 Sq Ft
- $184/SF
- 37 Days On Market
- 3 Beds
- 2 Baths
- Built 1912
24 Under Mountain Rd, Wassaic, NY 12592

**Multiple Offers. Highest and best due in HomePath by 4/3/25 at noon** This beautiful 2 story in Wassaic is a must see! This home has been fully renovated from top to bottom with many great updates including a new roof, new doors, new luxury vinyl plank flooring, fresh paint, 2 new bathrooms, new kitchen, new high efficiency propane boiler, updated septic system, and more! All this nestled on

Matthew Cave Hudson Property Services, LLC

24 Under Mountain Rd, Wassaic, NY 12592

Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,951 Sq Ft
211 Kent Rd, Kent, CT 06757

211 Kent Rd, Kent, CT 06757

/23
$110,000
- 3 Beds
- 2 Baths
- 1,288 Sq Ft
151 Scott Dr, Dover Plains, NY 12522

Beautiful Home in the Tally Ho Senior Community!Nestled on a premium lot, this charming and spacious home offers comfortable living in the desirable Tally Ho 55+ community. Step into the bright and open living room, dining area, and kitchen, all featuring vaulted ceilings that enhance the sense of space and light. The large kitchen is a chef’s dream, boasting abundant cabinetry and

Blake Michaud Serhant LLC

151 Scott Dr, Dover Plains, NY 12522

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