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Lakefront Homes in Winchester, CT

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431 West Wakefield Boulevard in Winchester, CT

DIRECT lakefront Single Family on Highland Pond

$2,600,000 9 bedrooms, 6 baths, 7000 sqft, 3 acres

538 Wheelers Point in Winchester, CT

DIRECT lakefront Single Family on Highland Pond

$1,699,500 4 bedrooms, 3 baths, 2496 sqft, 0.7 acres

424 East Wakefield Boulevard in Winchester, CT

DIRECT lakefront Single Family on Highland Pond

$1,595,000 5 bedrooms, 2 baths, 3693 sqft, 0.59 acres

435/434 West Wakefield Boulevard in Winchester, CT

DIRECT lakefront Single Family on Highland Pond

$1,400,000 8 bedrooms, 5 baths, 5231 sqft, 1.51 acres

722 Lake Drive in Winchester, CT

DIRECT lakefront Single Family on Highland Pond

$1,295,000 3 bedrooms, 3 baths, 2420 sqft, 0.17 acres

119 West Wakefield Boulevard in Winchester, CT

Off-the-water Single Family on Highland Pond

$849,900 4 bedrooms, 2 baths, 1781 sqft, 0.62 acres

Coming Soon - not showing yet!266 Perch Rock Trail in Winchester, CT

DIRECT lakefront Single Family on Highland Pond

$750,000 3 bedrooms, 2 baths, 1488 sqft, 0.15 acres

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Connecticut State MLS data last updated on Monday, June 30, 2025 at 3:03 AM

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