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Highland Lake Homes For Sale
Connecticut

Highland Lake Homes For Sale
Connecticut

Highland Lake, Connecticut

Highland Lake real estate is the third largest market for lake homes and land in Connecticut.

 

The closest major airport, Bradley International Airport, is only 25 miles away.

Highland Lake Real Estate

Total Listings
39
Total Value
$19,638,400
Updated as of
08-23-2019

Highland Lake, Connecticut

Highland Lake real estate is the third largest market for lake homes and land in Connecticut.

 

The closest major airport, Bradley International Airport, is only 25 miles away.

 

Highland Lake Real Estate for Sale

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210-212 West Wakefield Boulevard, Winchester, CT 06098 - Image 1
Waterfront

210-212 West Wakefield Boulevard

$1,900,000

Bedrooms: 11 |  Bathrooms: 9

Acreage: 1.17

View Details »

Highland Lake, CT

211/212 West Wakefield Boulevard, Winchester, CT 06098 - Image 1
Waterfront

211/212 West Wakefield Boulevard

$1,500,000

Bedrooms: 5 |  Bathrooms: 6

Acreage: 1.05

View Details »

Highland Lake, CT

850 East Wakefield Boulevard, Winchester, CT 06098 - Image 1
Waterfront

850 East Wakefield Boulevard

$925,000

Bedrooms: 4 |  Bathrooms: 3

Acreage: 0.43

View Details »

Highland Lake, CT

534 Wheelers Point, Winchester, CT 06098 - Image 1
Waterfront

534 Wheelers Point

$910,000

Bedrooms: 3 |  Bathrooms: 2

Acreage: 0.54

View Details »

Highland Lake, CT

504 West Wakefield Boulevard, Winchester, CT 06098 - Image 1
Waterfront

504 West Wakefield Boulevard

$849,900

Bedrooms: 3 |  Bathrooms: 3

Acreage: 0.57

View Details »

Highland Lake, CT

262 Perch Rock Trail, Winchester, CT 06098 - Image 1
Waterfront

262 Perch Rock Trail

$820,000

Bedrooms: 7 |  Bathrooms: 5

Acreage: 0.24

View Details »

Highland Lake, CT

543 West Wakefield Boulevard, Winchester, CT 06098 - Image 1: VIEW FROM WATERFRONT AREA UP TO HOUSE.
New Listing
Waterfront

543 West Wakefield Boulevard

$795,000

Bedrooms: 4 |  Bathrooms: 3

Acreage: 1

View Details »

Highland Lake, CT

51 East Lake Street, Winchester, CT 06098 - Image 1
Waterfront

51 East Lake Street

$789,000

Bedrooms: 6 |  Bathrooms: 5

Acreage: 0.7

View Details »

Highland Lake, CT

403 West Wakefield Boulevard, Winchester, CT 06098 - Image 1: Gorgeous Upscale Waterfront Home with Guest Cottage & 120 Feet of Waterfront was designed to enjoy all aspects of lake living!
Waterfront

403 West Wakefield Boulevard

$728,900

Bedrooms: 3 |  Bathrooms: 2

Acreage: 0.56

View Details »

Highland Lake, CT

422 East Wakefield Boulevard, Winchester, CT 06098 - Image 1
Waterfront

422 East Wakefield Boulevard

$699,900

Bedrooms: 4 |  Bathrooms: 3

Acreage: 0.48

View Details »

Highland Lake, CT

348 West Wakefield Boulevard, Winchester, CT 06098 - Image 1
Price Change
Waterfront

348 West Wakefield Boulevard

$675,000

Bedrooms: 3 |  Bathrooms: 2

Acreage: 0.08

View Details »

Highland Lake, CT

760 Lake Drive, Winchester, CT 06098 - Image 1
Waterfront

760 Lake Drive

$675,000

Bedrooms: 3 |  Bathrooms: 3|  SF: 2400

Acreage: 0.2

View Details »

Highland Lake, CT

210 West Wakefield Boulevard, Winchester, CT 06098 - Image 1
Waterfront

210 West Wakefield Boulevard

$674,000

Bedrooms: 4 |  Bathrooms: 2

Acreage: 0.12

View Details »

Highland Lake, CT

714 West Wakefield Boulevard, Winchester, CT 06098 - Image 1
Price Change
Waterfront

714 West Wakefield Boulevard

$630,000

Bedrooms: 3 |  Bathrooms: 4

Acreage: 0.17

View Details »

Highland Lake, CT

878 West Wakefield Boulevard, Winchester, CT 06098 - Image 1
Waterfront

878 West Wakefield Boulevard

$575,000

Bedrooms: 4 |  Bathrooms: 2

Acreage: 0.35

View Details »

Highland Lake, CT

87 East Lake Street, Winchester, CT 06098 - Image 1
Waterfront

87 East Lake Street

$575,000

Bedrooms: 3 |  Bathrooms: 2

Acreage: 0.11

View Details »

Highland Lake, CT

848 East Wakefield, Winchester, CT 06098 - Image 1: Waterfront
Waterfront

848 East Wakefield

$569,900

Bedrooms: 3 |  Bathrooms: 2

Acreage: 0.13

View Details »

Highland Lake, CT

39 East Lake Street, Winchester, CT 06098 - Image 1
Waterfront

39 East Lake Street

$519,000

Bedrooms: 4 |  Bathrooms: 2

Acreage: 0.69

View Details »

Highland Lake, CT

842 East Wakefield Boulevard, Winchester, CT 06098 - Image 1: This should be your holiday card!!!
Price Change
Waterfront

842 East Wakefield Boulevard

$489,900

Bedrooms: 3 |  Bathrooms: 3

Acreage: 0.23

View Details »

Highland Lake, CT

212 East Wakefield Boulevard, Winchester, CT 06098 - Image 1
Waterfront

212 East Wakefield Boulevard

$479,900

Bedrooms: 3 |  Bathrooms: 2

Acreage: 0.17

View Details »

Highland Lake, CT


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12

About Highland Lake

Highland Lake real estate is the third largest market for lake homes and land in Connecticut.

 

The closest major airport, Bradley International Airport, is only 25 miles away.

Sell Your Lake Home

Off Market Properties

210-212 West Wakefield Boulevard, Winchester, CT 06098 - Image 1
Waterfront

210-212 West Wakefield Boulevard

$1,900,000

Bedrooms: 11 |  Bathrooms: 9

Acreage: 1.17

View Details »Highland Lake, CT
211/212 West Wakefield Boulevard, Winchester, CT 06098 - Image 1
Waterfront

211/212 West Wakefield Boulevard

$1,500,000

Bedrooms: 5 |  Bathrooms: 6

Acreage: 1.05

View Details »Highland Lake, CT
850 East Wakefield Boulevard, Winchester, CT 06098 - Image 1
Waterfront

850 East Wakefield Boulevard

$925,000

Bedrooms: 4 |  Bathrooms: 3

Acreage: 0.43

View Details »Highland Lake, CT
534 Wheelers Point, Winchester, CT 06098 - Image 1
Waterfront

534 Wheelers Point

$910,000

Bedrooms: 3 |  Bathrooms: 2

Acreage: 0.54

View Details »Highland Lake, CT
504 West Wakefield Boulevard, Winchester, CT 06098 - Image 1
Waterfront

504 West Wakefield Boulevard

$849,900

Bedrooms: 3 |  Bathrooms: 3

Acreage: 0.57

View Details »Highland Lake, CT
262 Perch Rock Trail, Winchester, CT 06098 - Image 1
Waterfront

262 Perch Rock Trail

$820,000

Bedrooms: 7 |  Bathrooms: 5

Acreage: 0.24

View Details »Highland Lake, CT
543 West Wakefield Boulevard, Winchester, CT 06098 - Image 1: VIEW FROM WATERFRONT AREA UP TO HOUSE.
New Listing
Waterfront

543 West Wakefield Boulevard

$795,000

Bedrooms: 4 |  Bathrooms: 3

Acreage: 1

View Details »Highland Lake, CT
51 East Lake Street, Winchester, CT 06098 - Image 1
Waterfront

51 East Lake Street

$789,000

Bedrooms: 6 |  Bathrooms: 5

Acreage: 0.7

View Details »Highland Lake, CT
403 West Wakefield Boulevard, Winchester, CT 06098 - Image 1: Gorgeous Upscale Waterfront Home with Guest Cottage & 120 Feet of Waterfront was designed to enjoy all aspects of lake living!
Waterfront

403 West Wakefield Boulevard

$728,900

Bedrooms: 3 |  Bathrooms: 2

Acreage: 0.56

View Details »Highland Lake, CT
422 East Wakefield Boulevard, Winchester, CT 06098 - Image 1
Waterfront

422 East Wakefield Boulevard

$699,900

Bedrooms: 4 |  Bathrooms: 3

Acreage: 0.48

View Details »Highland Lake, CT
348 West Wakefield Boulevard, Winchester, CT 06098 - Image 1
Price Change
Waterfront

348 West Wakefield Boulevard

$675,000

Bedrooms: 3 |  Bathrooms: 2

Acreage: 0.08

View Details »Highland Lake, CT
760 Lake Drive, Winchester, CT 06098 - Image 1
Waterfront

760 Lake Drive

$675,000

Bedrooms: 3 |  Bathrooms: 3|  SF: 2400

Acreage: 0.2

View Details »Highland Lake, CT
210 West Wakefield Boulevard, Winchester, CT 06098 - Image 1
Waterfront

210 West Wakefield Boulevard

$674,000

Bedrooms: 4 |  Bathrooms: 2

Acreage: 0.12

View Details »Highland Lake, CT
714 West Wakefield Boulevard, Winchester, CT 06098 - Image 1
Price Change
Waterfront

714 West Wakefield Boulevard

$630,000

Bedrooms: 3 |  Bathrooms: 4

Acreage: 0.17

View Details »Highland Lake, CT
878 West Wakefield Boulevard, Winchester, CT 06098 - Image 1
Waterfront

878 West Wakefield Boulevard

$575,000

Bedrooms: 4 |  Bathrooms: 2

Acreage: 0.35

View Details »Highland Lake, CT
87 East Lake Street, Winchester, CT 06098 - Image 1
Waterfront

87 East Lake Street

$575,000

Bedrooms: 3 |  Bathrooms: 2

Acreage: 0.11

View Details »Highland Lake, CT
848 East Wakefield, Winchester, CT 06098 - Image 1: Waterfront
Waterfront

848 East Wakefield

$569,900

Bedrooms: 3 |  Bathrooms: 2

Acreage: 0.13

View Details »Highland Lake, CT
39 East Lake Street, Winchester, CT 06098 - Image 1
Waterfront

39 East Lake Street

$519,000

Bedrooms: 4 |  Bathrooms: 2

Acreage: 0.69

View Details »Highland Lake, CT
842 East Wakefield Boulevard, Winchester, CT 06098 - Image 1: This should be your holiday card!!!
Price Change
Waterfront

842 East Wakefield Boulevard

$489,900

Bedrooms: 3 |  Bathrooms: 3

Acreage: 0.23

View Details »Highland Lake, CT
212 East Wakefield Boulevard, Winchester, CT 06098 - Image 1
Waterfront

212 East Wakefield Boulevard

$479,900

Bedrooms: 3 |  Bathrooms: 2

Acreage: 0.17

View Details »Highland Lake, CT

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12

About Highland Lake

Highland Lake real estate is the third largest market for lake homes and land in Connecticut.

 

The closest major airport, Bradley International Airport, is only 25 miles away.