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Windham County Waterfront Real Estate Search

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Allen Hill Rd, Brooklyn image
Allen Hill Rd, Brooklyn $5,500,000 ▼

Welcome to Pinedale Farms, a rare large-scale development opportunity in the heart of Brooklyn. This offering includes 136.38 acres of industrial-zoned land along with th...

  • 24140370 MLS
158 W Quasset Rd, Woodstock image
158 W Quasset Rd, Woodstock $2,495,000 ▼

Extraordinary Waterfront Estate. Set on an exceptional 5.5-acre private lot with 265 feet of shoreline frontage, this completely rebuilt luxury residence offers a rare op...

  • 4 Beds
  • 4 Baths
  • 24180508 MLS
317 Bebbington Rd, Ashford image
317 Bebbington Rd, Ashford $1,995,000 ▼

CROOKES ORCHARD - A LEGACY FARM OF EXTRAORDINARY BEAUTY AND OPPORTUNITY! One of Northeast Connecticut's most beloved agricultural destinations, presents an exceptionally ...

  • 24186879 MLS
155 Paine Rd, Woodstock image
155 Paine Rd, Woodstock $1,650,000

Set on a breathtaking stretch of rolling countryside in historic Woodstock, this extraordinary Federal Colonial reproduction blends timeless New England craftsmanship wit...

  • 4 Beds
  • 6 Baths
  • 24174159 MLS
1374 Rte 171, Woodstock image
1374 Rte 171, Woodstock $1,450,000

Set on 10.3 private acres in desirable Woodstock Valley, "Blue Heron Glade" offers a rare blend of privacy, natural beauty, and thoughtfully designed living spaces in Con...

  • 4 Beds
  • 6 Baths
  • 24177811 MLS
25 Kennerson Reservoir Rd, Eastford image
25 Kennerson Reservoir Rd, Eastford $1,350,000

158 ACRES W/EXPANSIVE HALLS POND FRONTAGE - 3 PARCELS, FULLY RENOVATED 2-FAMILY DWELLING, & ENDLESS POSSIBILITIES! Encompassing a remarkable combination of income-produci...

  • 3 Beds
  • 4 Baths
  • 24185378 MLS
25 Kennerson Reservoir Rd, Eastford image
25 Kennerson Reservoir Rd, Eastford $1,350,000

158 ACRES W/EXPANSIVE HALLS POND FRONTAGE - 3 PARCELS, FULLY RENOVATED 2-FAMILY DWELLING, & ENDLESS POSSIBILITIES! Encompassing a remarkable combination of income-produci...

  • 24183806 MLS
95 Pole Bridge Rd, Woodstock image
95 Pole Bridge Rd, Woodstock $1,275,000

This extraordinary waterfront estate on Chamberlain Lake offers a lifestyle rarely found in Connecticut. With 200ft of private lake frontage, this custom post-and-beam Ca...

  • 4 Beds
  • 4 Baths
  • 24185273 MLS
46 Cemetery Rd, Canterbury image
46 Cemetery Rd, Canterbury $1,200,000

Exceptional opportunity to own a private country estate featuring a well-maintained Cape-style log home set on 41.83 acres of beautiful land. This charming residence offe...

  • 3 Beds
  • 2 Baths
  • 24179809 MLS
9 Becola Rd, Thompson image
9 Becola Rd, Thompson $859,900 ▼

Rare opportunity to own 100 feet of beautiful pond frontage in Thompson, CT! From the moment you arrive, you'll fall in love with the peaceful setting, breathtaking water...

  • 3 Beds
  • 3 Baths
  • 24169232 MLS
56 River Rd, Killingly image
56 River Rd, Killingly $850,000

Welcome to your own retreat on more than 5 acres along 5 Mile River. Offering over 5,000 square feet of living space, this custom Colonial combines timeless craftsmanship...

  • 5 Beds
  • 3 Baths
  • 24176144 MLS
82 Kennerson Reservoir Road, Eastford image
82 Kennerson Reservoir Road, Eastford $850,000 ▼

Experience exceptional waterfront living overlooking the beautiful 88-acre Kennerson Reservoir in scenic Eastford. This impressive 4-bedroom, 3-bath home offers breathtak...

  • 4 Beds
  • 3 Baths
  • 73533276 MLS
82 Kennerson Reservoir Road, Eastford image
82 Kennerson Reservoir Road, Eastford $850,000 ▼

Experience exceptional waterfront living overlooking the beautiful 88-acre Kennerson Reservoir in scenic Eastford. This impressive 4-bedroom, 3-bath home offers breathtak...

  • 4 Beds
  • 3 Baths
  • 1413855 MLS
82 Kennerson Reservoir Rd, Eastford image
82 Kennerson Reservoir Rd, Eastford $850,000 ▼

Experience exceptional waterfront living overlooking the beautiful 88-acre Kennerson Reservoir in scenic Eastford. This impressive 4-bedroom, 3-bath home offers breathtak...

  • 4 Beds
  • 3 Baths
  • 24178434 MLS
175 Cranberry Bog Rd, Killingly image
175 Cranberry Bog Rd, Killingly $745,000

Wow! 14 acres and 5 bedrooms! This stunning property is secluded yet close to amenities. Sweeping gravel drive brings you to this sunny oasis in the woods. An impeccably ...

  • 5 Beds
  • 3 Baths
  • 24185535 MLS
60 Indian Spring Rd, Woodstock image
60 Indian Spring Rd, Woodstock $699,000 ▼

Perched above the shoreline of private Witches Woods Lake, this fully furnished waterfront retreat offers breathtaking water views, exceptional privacy, and a rare sense ...

  • 2 Beds
  • 2 Baths
  • 24142329 MLS
188 Laurel Point Rd, Killingly image
188 Laurel Point Rd, Killingly $690,000

Lakefront Living at Its Finest! Experience the beauty of waterfront living in this charming 3-bedroom, 2 full-bath home nestled on the shores of a Alexanders Lake. Wake ...

  • 3 Beds
  • 2 Baths
  • 24196150 MLS
592 Ference Rd, Ashford image
592 Ference Rd, Ashford $654,900 ▼

Rare opportunity to own a waterfront ranch with a legal in-law apartment set on over 3 private acres in the peaceful countryside of Ashford. Boasting over 800 feet of dir...

  • 3 Beds
  • 3 Baths
  • 24163257 MLS
23 Totem Pole Rd, Thompson image
23 Totem Pole Rd, Thompson $650,000

Do not miss out on the rare opportunity to own this waterfront property on Quaddick Lake. Colonial style ~2600 sq ft house featuring 4 bedrooms with 3 full bathrooms, new...

  • 4 Beds
  • 3 Baths
  • 24196607 MLS
511 Perrin Rd, Woodstock image
511 Perrin Rd, Woodstock $650,000

Perfect Countryside Elegance. Welcome to 511 Perrin Road, an exceptional country estate gracefully set atop a private 3.5-acre hillside in scenic Woodstock. A long paved ...

  • 2 Beds
  • 3 Baths
  • 24187780 MLS
232 Ballouville Rd, Killingly image
232 Ballouville Rd, Killingly $474,900

Side by side two family home, perfect for owner-occupants or investors. Each unit offers a functional layout. One unit features all 4 bedrooms on the second floor with th...

  • 8 Beds
  • 2 Baths
  • 24190300 MLS
Plainfield Pike, Sterling image
Plainfield Pike, Sterling $470,000 ▲

Built in 1825 in the Quaint town of Oneco this Adorable 3 Family on Oneco Pond is a great Waterfront Property!!! In the Summertime enjoy Kayaking, Canoeing, Swimming, Fis...

  • 5 Beds
  • 3 Baths
  • 24190726 MLS
760 Upper Maple, Killingly image
760 Upper Maple, Killingly $424,900 ▼

Step back in time with this beautifully preserved circa 1815 antique home, known as the Old Danielson house, set on an expansive 6.1acre lot. Rich in history and timeless...

  • 5 Beds
  • 2 Baths
  • 24170264 MLS
19 Henry Dr Unit 19, Plainfield image
19 Henry Dr Unit 19, Plainfield — Moosup River Estates $419,000

Moosup River Estates is a 55 and over community of stand alone condos along the Moosup River. This unit was thoughtfully completed, and is now ready for it next owner to ...

  • 2 Beds
  • 2 Baths
  • 24178362 MLS
  • Moosup River Estates Bldg.
222 Tower Hill Rd, Chaplin image
222 Tower Hill Rd, Chaplin $389,000 ▼

Beautifully set on 4.02 scenic acres in Chaplin, Connecticut, this charming 3-bedroom, 2-bath home offers the perfect blend of character, privacy, and versatility. Featur...

  • 3 Beds
  • 2 Baths
  • 24178626 MLS
15 Cracow Ave, Windham image
15 Cracow Ave, Windham $360,000 ▲

Welcome to 15 Cracow Ave in Windham, a beautifully updated 3-bedroom, 2-full-bath ranch offering the perfect blend of single-level living, modern finishes, and outdoor li...

  • 3 Beds
  • 2 Baths
  • 24181488 MLS
983 Riverside Dr, Thompson image
983 Riverside Dr, Thompson $325,000 ▼

Fantastic 2 family with both units recently renovated. 3 bedrooms in one unit. 2 bedrooms in other with a formal dining room Parking next to each unit and full basement....

  • 5 Beds
  • 2 Baths
  • 24095430 MLS
00 Ide Perrin Rd, Woodstock image
00 Ide Perrin Rd, Woodstock $299,900

On a private road surrounded by unspoiled natural beauty, this remarkable 79-acre property offers exceptional privacy and endless potential. Two brooks enhance the landsc...

  • 24174800 MLS
259 Church St, Putnam image
259 Church St, Putnam $275,000 ▼

Recently refreshed and priced aggressively for a fast sale, this move-in ready property is an incredible opportunity for both homeowners and investors. The home features ...

  • 3 Beds
  • 1 Baths
  • 24156434 MLS
19 Cady St, Killingly image
19 Cady St, Killingly $250,000

Excellent investment or owner-occupant opportunity in Killingly! Whether you are looking to expand your portfolio with instant cash flow or occupy one unit while letting ...

  • 3 Beds
  • 2 Baths
  • 24196295 MLS
34 Pond St Unit 7, Sterling image
34 Pond St Unit 7, Sterling — River Bend $249,900

Enjoy affordable, low-maintenance waterfront living in this charming 8-unit condominium community! Tucked away at the back of the complex, this 2-bedroom, 1.5-bath condo ...

  • 2 Beds
  • 2 Baths
  • 24194085 MLS
  • River Bend Bldg.
305 Tripp Hollow Rd, Brooklyn image
305 Tripp Hollow Rd, Brooklyn $229,900

Amazing land opportunity offers nature's bounty on 35 subdividable acres consisting of multiple parcels. The premises includes a picturesque pond, has approximately 900' ...

  • 73547677 MLS
305 Tripp Hollow Rd, Brooklyn image
305 Tripp Hollow Rd, Brooklyn $229,900

Amazing land opportunity offers nature's bounty on 35 subdividable acres consisting of multiple parcels. The premises includes a picturesque pond, has approximately 900 f...

  • 24190434 MLS
45 Main St Unit 205, Plainfield image
45 Main St Unit 205, Plainfield — Central Square $196,000

Welcome home to this charming 2-bedroom, 1.5-bath mill-style condominium, where historic character and modern updates come together beautifully. Soaring ceilings, oversiz...

  • 2 Beds
  • 2 Baths
  • 24194453 MLS
  • Central Square Bldg.
W Thompson Rd, Thompson image
W Thompson Rd, Thompson $140,000 ▼

0 Thompson Road offers a picturesque 22.8 acre mixed-use commercial land opportunity located in the BDD (Business Development District) zone, allowing for energy storage,...

  • 24146108 MLS
11 Otis St, Killingly image
11 Otis St, Killingly $99,000 ▼

Unlock the potential of this residential property located at 11 Otis Street in Killingly. Offering a unique opportunity for investors, builders, or anyone looking to crea...

  • 24160819 MLS
37 Katherine Ave, Killingly image
37 Katherine Ave, Killingly $49,900 ▼

Waterfront lot located on the Quinebaug River in an established neighborhood. City water hookup available. Conveniently situated near shopping, dining, Route 6, Route 101...

  • 24136993 MLS

IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but is not guaranteed. © 2026 State-Wide Multiple Listing Service. All rights reserved. Data Last Updated:

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

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