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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
180 & 189 Lake Rd, Killingly image
180 & 189 Lake Rd, Killingly $2,091,000

Opportunity awaits! Two parcels totaling 69.70 acres are being offered together in a desirable Killingly location. Located at 189 Lake Road (60 acres) with 930 ft of fron...

  • 24218042 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
317 Bebbington Rd, Ashford image
317 Bebbington Rd, Ashford $1,699,000

CROOKES ORCHARD - A 153-ACRE CONNECTICUT LEGACY FARM WITH HOME BUILDING LOT! One of Northeast Connecticut's most beloved agricultural destinations, presents an exceptiona...

  • 24213132 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
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
1374 Rte 171, Woodstock image
1374 Rte 171, Woodstock $1,299,000 ▼

Set on 10.3 private acres in desirable Woodstock Valley, Blue Heron Glade offers exceptional privacy, natural beauty and remarkable versatility. A long private drive cros...

  • 4 Beds
  • 6 Baths
  • 24177811 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
14 Ashford Lake Dr, Ashford image
14 Ashford Lake Dr, Ashford $1,200,000

Stunningly situated on the mouth of Ashford Lake, a project of love has culminated into a brand new dream home, with panoramic views of the lake. Quality craftsmanship is...

  • 2 Beds
  • 4 Baths
  • 24215704 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
246 Pinch St, Scotland image
246 Pinch St, Scotland $899,000

Come see the inspiration of two nature lovers who have created a private wildlife sanctuary unlike any other. This 70.75 acre parcel is comprised of two lots with conside...

  • 1 Beds
  • 2 Baths
  • 24210054 MLS
300 Starkweather Rd, Plainfield image
300 Starkweather Rd, Plainfield $699,000

Discover this distinctive country retreat on 5+ picturesque acres, featuring a custom-built home with approximately 2,264 finished square feet, 3 bedrooms, and 2.5 baths....

  • 3 Beds
  • 3 Baths
  • 24214706 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
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
97 Cushman Rd, Ashford image
97 Cushman Rd, Ashford $625,000 ▼

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
7 Amidon Dr, Ashford image
7 Amidon Dr, Ashford $599,900

LAKE LIFE AWAITS!! This stunning like-new home has been fully renovated to include 2 full beds and baths, with a 3rd loft style flex room which can be used for a bedroom ...

  • 3 Beds
  • 2 Baths
  • 24208918 MLS
47 Sherman Rd, Woodstock image
47 Sherman Rd, Woodstock $595,000 ▼

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
172 Snake Meadow Rd, Plainfield image
172 Snake Meadow Rd, Plainfield $575,000

Set on more than 3 private, peaceful acres with a brook running through the property, this farmhouse-style Colonial blends country charm, character and thoughtful updates...

  • 4 Beds
  • 3 Baths
  • 24215953 MLS
204 Pine Hollow Rd, Killingly image
204 Pine Hollow Rd, Killingly $550,000

204 Pine Hollow Road-an exceptional waterfront opportunity on beautiful Alexander's Lake. Enjoy the very best of the lake lifestyle, with a functional one-car garage offe...

  • 2 Beds
  • 1 Baths
  • 24209159 MLS
20 Amidon Dr, Ashford image
20 Amidon Dr, Ashford $525,000

Set on the shores of Lake Chaffee, this waterfront ranch offers easy one level living with peaceful views and year-round recreation right outside your door. This beautifu...

  • 2 Beds
  • 2 Baths
  • 24214312 MLS
813 Westford Rd, Ashford image
813 Westford Rd, Ashford $515,000

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...

  • 3 Beds
  • 2 Baths
  • 24217299 MLS
60 Ashford Lake Dr, Ashford image
60 Ashford Lake Dr, Ashford $477,999 ▼

LOW HOA FEES which include use of 2 private beaches & includes road maintenance. This turnkey, one-level, direct waterfront, year-round home has its own private beach, co...

  • 2 Beds
  • 1 Baths
  • 24201756 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
128 Holmes Rd, Pomfret image
128 Holmes Rd, Pomfret $449,999 ▼

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
32 Ashford Rd, Eastford image
32 Ashford Rd, Eastford $435,000

If you've been searching for true country living, privacy, and land for exploration, this 17-acre property in Eastford delivers all of it. With Bigelow Brook (a Class A t...

  • 3 Beds
  • 2 Baths
  • 24209461 MLS
1147 Plainfield Pike, Sterling image
1147 Plainfield Pike, Sterling $425,000 ▼

WATERFRONT 3 Family ON ONECO POND! LIVE IN ONE UNIT AND COLLECT RENT FROM THE OTHER TWO UNITS or Rent out All Three Units! Take the side steps down to the big back yard w...

  • 5 Beds
  • 3 Baths
  • 24190726 MLS
73 Lakeview Dr, Ashford image
73 Lakeview Dr, Ashford $369,500

Discover the charm of lakefront living on beautiful Lake Chaffee! This thoughtfully renovated and furnished 2-bedroom, 1-bath cottage offers the perfect blend of charm, c...

  • 2 Beds
  • 1 Baths
  • 24216092 MLS
6 Old Rte 12, Thompson image
6 Old Rte 12, Thompson $349,999

HISTORIC CHARM MEETS VALUE ADD POTENTIAL in Connecticut's Quiet Corner! This distinctive multi family property offers 3 residential units plus a fourth space with commerc...

  • 9 Beds
  • 4 Baths
  • 24210190 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
15 Cracow Ave, Windham image
15 Cracow Ave, Windham $324,999

Imagine summer mornings with coffee on the new Trex deck, afternoons spent by your in-ground pool, and evenings launching a kayak right into the river behind your backyar...

  • 3 Beds
  • 2 Baths
  • 24214512 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 $285,000 ▼

**MOTIVATED SELLER**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 comp...

  • 3 Beds
  • 1 Baths
  • 24203002 MLS
property image
Putnam $235,000

35.41 Acres of Beautiful, Mostly Level Land with Brook Discover the possibilities on this beautiful 35.41-acre parcel of mostly level land, offering a peaceful setting w...

  • 24208250 MLS
Ryler Ct, Thompson image
Ryler Ct, Thompson $175,000

Rare 8.34-Acre Property in a Highly Desirable Neighborhood! Discover the perfect opportunity to build your dream home on this exceptional 8.34-acre property, consisting...

  • 24217151 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
181 Paradise Dr, Brooklyn image
181 Paradise Dr, Brooklyn $160,000

Needs to be completed. Add some mini splits for your heat and air. Just under 1 acre. Located on Paradise Lake. Water front cottage.

  • 1 Beds
  • 1 Baths
  • 24214866 MLS
00 Beecher Rd, Brooklyn image
00 Beecher Rd, Brooklyn $150,000

Lovely piece of land with woodlands and open areas. The right hand boundary being the center line of Blackwell's Brook. There are some areas of Flood Plain along the broo...

  • 24215157 MLS
11 Otis St, Killingly image
11 Otis St, Killingly $69,000

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...

  • 24210414 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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