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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
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
158 W Quasset Rd, Woodstock image
158 W Quasset Rd, Woodstock $1,995,000 ▼

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
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 $1,395,000 ▼

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

Waterfront living at its most private and picturesque on beautiful Chamberlain Lake. Set on 200 feet of private lake frontage, this exceptional custom post-and-beam Cape ...

  • 4 Beds
  • 4 Baths
  • 24185273 MLS
25 Lakeview St, Thompson image
25 Lakeview St, Thompson $1,100,000

Lakefront luxury awaits on Little Pond in Thompson, CT. This brand-new 2,100sq. ft. custom build retreat offers effortless waterfront living with panoramic views througho...

  • 3 Beds
  • 3 Baths
  • 24202934 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
26 Beecher Rd, Brooklyn image
26 Beecher Rd, Brooklyn $825,000

This beautiful old Colonial home was built on one of the first four parcels of land when Brooklyn was first settled. The historic character is seen throughout the home bu...

  • 5 Beds
  • 3 Baths
  • 24204013 MLS
82 Kennerson Reservoir Rd, Eastford image
82 Kennerson Reservoir Rd, Eastford $795,000

A HIDDEN WATERFRONT ESCAPE MOST PEOPLE DON'T EVEN KNOW EXISTS FOR SWIMMING AND KAYAKING! Welcome to Kennerson Reservoir, a peaceful, tucked-away lake bordered by protecte...

  • 4 Beds
  • 3 Baths
  • 24203513 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
20 Loyola Rd, Woodstock image
20 Loyola Rd, Woodstock $698,900

Enjoy Lake Living in Woodstock's Quiet Corner at Quasset Lake! Welcome to this beautifully landscaped 2-3 bedroom, 2.5-bath home in the desirable Quasset Lake community,...

  • 2 Beds
  • 3 Baths
  • 24193568 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
60 Indian Spring Rd, Woodstock image
60 Indian Spring Rd, Woodstock $689,000 ▼

Perched above the shoreline of private Witches Woods Lake, this beautifully renovated waterfront retreat pairs breathtaking water views with exceptional privacy and an in...

  • 2 Beds
  • 2 Baths
  • 24142329 MLS
97 Cushman Rd, Ashford image
97 Cushman Rd, Ashford $650,000

Here's your opportunity to have the feeling of a little piece of Vermont while being in Connecticut. About 7 minutes to the highway and 10 minutes to UConn. 17.3 acres cr...

  • 5 Beds
  • 4 Baths
  • 24198311 MLS
592 Ference Rd, Ashford image
592 Ference Rd, Ashford $649,900 ▼

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
189 Butts Bridge Rd, Canterbury image
189 Butts Bridge Rd, Canterbury $615,000

A rare 16-acre country property in Canterbury's Rural District - a private residence rich with timeless New England character, set on extraordinary grounds. The home pair...

  • 5 Beds
  • 3 Baths
  • 24180596 MLS
47 Sherman Rd, Woodstock image
47 Sherman Rd, Woodstock $600,000

Modern amenities meet unmatched seclusion in this 2,000+ sq ft colonial. A mostly level lot offers abundant green space, fruiting plants, and perennials, while the side d...

  • 4 Beds
  • 3 Baths
  • 24204008 MLS
511 Perrin Rd, Woodstock image
511 Perrin Rd, Woodstock $599,000 ▼

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
813 Westford Rd, Ashford image
813 Westford Rd, Ashford $533,000

Beautifully restored 1880 Colonial farmhouse set on an impressive 18.03 acres, offering a wonderful opportunity for farming, homesteading, or simply enjoying the peace an...

  • 5 Beds
  • 2 Baths
  • 24203884 MLS
60 Ashford Lake Dr, Ashford image
60 Ashford Lake Dr, Ashford $489,999 ▼

Have you ever wanted your own private backyard beach with private dock? This turnkey, one-level, direct waterfront, year-round home has its own private beach, completed i...

  • 2 Beds
  • 1 Baths
  • 24201756 MLS
128 Holmes Rd, Pomfret image
128 Holmes Rd, Pomfret $475,000 ▼

Investors, take notice! This antique Colonial is situated on an impressive 6.6-acre private lot offering a peaceful setting and endless potential. A portion of the acreag...

  • 4 Beds
  • 3 Baths
  • 24197506 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
1147 Plainfield Pike, Sterling image
1147 Plainfield Pike, Sterling $450,000 ▼

Built in 1825 in the Quaint town of Oneco this Adorable, 3 Family Waterfront is a Rare find on Oneco Pond!!! Take the side steps down to the big back yard with a large Fi...

  • 5 Beds
  • 3 Baths
  • 24190726 MLS
25 Provost Ln, Killingly image
25 Provost Ln, Killingly $449,900 ▼

BACK ON MARKET - NO FAULT OF THE PROPERTY! Buyer's circumstances changed prior to inspections being completed, giving you a second opportunity to make this home yours. Do...

  • 3 Beds
  • 2 Baths
  • 24199253 MLS
73 Lakeview Dr, Ashford image
73 Lakeview Dr, Ashford $384,900

Lakefront living at its best on beautiful Lake Chaffee! This considerately renovated two bedroom, one full-bath cottage offers the perfect blend of charm, comfort, and mo...

  • 2 Beds
  • 1 Baths
  • 24205788 MLS
15 Cracow Ave, Windham image
15 Cracow Ave, Windham $350,000 ▼

Move-in ready, single-level living meets your own private backyard retreat at 15 Cracow Avenue. This well-maintained 3-bedroom, 2-full-bath ranch offers the convenience b...

  • 3 Beds
  • 2 Baths
  • 24181488 MLS
157 Paradise Dr, Brooklyn image
157 Paradise Dr, Brooklyn $349,000

Escape to your own private lakeside retreat at 157 Paradise Drive. Tucked away and set directly on the water, this charming one-bedroom home offers a peaceful setting tha...

  • 1 Beds
  • 1 Baths
  • 24207175 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. Each unit has a washer and a dryer. Each uni...

  • 5 Beds
  • 2 Baths
  • 24198176 MLS
111 Island Rd, Killingly image
111 Island Rd, Killingly $299,900 ▼

A rare opportunity to create your own waterfront retreat on Alexander's Lake. This 3-bedroom, 1-bath home offers 1,282 square feet of living space with direct lake fronta...

  • 3 Beds
  • 1 Baths
  • 24198542 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
19 River St, Plainfield image
19 River St, Plainfield $290,000

Charming, Cozy, and 100% Move-In Ready! Everything has been done for you! Just three short years ago, this adorable 3-bed, 1-bath home received a complete tune-up, includ...

  • 3 Beds
  • 1 Baths
  • 24203002 MLS
19 Cady St, Killingly image
19 Cady St, Killingly $290,000 ▲

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 the tenant...

  • 3 Beds
  • 2 Baths
  • 24196295 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
49 Stone Rd, Killingly image
49 Stone Rd, Killingly $164,900

LOCATION LOCATION LOCATION!! 2.3 acre building lot with over 295' of water frontage on the Five Mile River! Build your dream home on this tranquil park like setting. The ...

  • 24206785 MLS
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

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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