508 West Wakefield Boulevard, Winchester, CT 06098 - Photo 1

1/1

$1,575,000

Sold
Closed
Single Family
7 Beds
4 Full Baths
2,687 Sq. Ft.
3 Car Garage

1/1

Property Description

Welcome to Strong Island, a waterfront retreat on Highland Lake. The clean waters of Highland Lake in the town of Winchester in Litchfield County surround this 1.6 acres island. History abounds for this property as the original house dates back to 1890. There were significant alterations made in 1920 that added several rooms, a boat house, a barn and porch. Babe Ruth made several trips to Strong Island for his weekends and vacations away from NYC. Strong Island is one of the largest islands on Highland Lake and has the best views. The position of this island give it the longest view of the lake on a North view and also on an Easterly view. The position of the main house on the island, the various docks, piers and out buildings make this property unable to be duplicated today. Strong Island is a trophy property that needs some polishing, but incredible in so many ways.

Full Property Details

Full Property Details for 508 W Wakefield Blvd

General

Sold For: $1,575,000
Taxes: (July 2025-June 2026)
Status: Closed
Type: Single Family
Source: SMARTMLS
MLS ID: 24024787
Added to Site: 613 day(s) ago

Interior

Number of Rooms: 11
Fireplace: Yes
Number of Fireplaces: 2
Appliances: Microwave, Refrigerator, Freezer, Dishwasher

Rooms

Bathrooms

Total Bathrooms: 4
Full Bathrooms: 4

Bedrooms

Total Bedrooms: 7
Primary Bedroom: Primary Bedroom, Upper
Bedroom 1: Bedroom, Upper
Bedroom 2: Bedroom, Upper
Bedroom 3: Bedroom, Upper
Bedroom 4: Bedroom, Upper
Bedroom 5: Bedroom, Upper
Bedroom 6: Bedroom, Upper

Other Rooms

Living Room: Living Room - Palladian Window(s), Fireplace, Main
Dining Room: Dining Room - Bay/Bow Window, Main

Exterior

Exterior Features: Sidewalk, Terrace, Barn, Cabana, Gutters, Stone Wall
Color: Yellow

Parking

Garage: Yes
Garage Spaces: 3
Parking: Detached Garage

Location

County: Litchfield
Neighborhood: Sucker Brook
Driving Directions: GPS friendly

School Information

Elementary School: Per Board of Ed
High School: Per Board of Ed

Community

Community Name: Sucker Brook

Heating & Cooling

Cooling Type: None
Heating Type: Hot Air, Oil
Heating Fuel: Oil
Water Heater: Domestic

Utilities

Sewer: Public Sewer In Street
Water: Private Well

Structural Information

Architectural Style: Victorian
Construction Status: No/Resale
Exterior Const.: Clapboard
Basement Desc.: Full
Roof: Metal
Square Feet: 2,687
Above Ground: 2,687 Sq. Ft.
Year Built: 1890

Lot Features

Lot Size (Acres): 1.63
Zoning: HL
Lot Description: Non Conforming Lot, Water View

Water Features

Water Front: Yes
Water View: Yes
Water Front Desc.: Lake, Walk to Water, Dock or Mooring, Water Community, View

Financial Considerations

Assessment Amount: $1,131,130
Tax Year: July 2025-June 2026

Disclosures and Reports

Property ID: 925719

Listed by William Pitt Sotheby's Int'l, Pierre Moran
Sold by Tier 1 Real Estate, THE MEAGAN ALBERT TEAM, Meagan Albert

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Listing agent

— 508 W Wakefield Blvd —

Pierre Moran

William Pitt Sotheby's Int'l

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Schools

Schools serving 508 W Wakefield Blvd

School District:Winchester School District

Name	Grades	Distance
Pearson Middle School 2 Wetmore Avenue, Winsted, CT 06098	3-6	2.2 mi

Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 508 W Wakefield Blvd

Date

Details

Price

Change

Source

6/30/2025

Sold

$1,575,000

-4.55%

MLS

6/19/2024

Listed

$1,650,000

—

MLS

Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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3
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Total Baths
1,178
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Beds
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Total Bath
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Sq. Ft.

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Single Family
Active
Updated 2 days ago

4
Beds
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Total Baths
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Active
Updated 4 days ago

6
Beds
2
Total Baths
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Price Reduced

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Beds
3
Total Baths
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Price Reduced

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$4,200

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Sold

$1,500,000

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Single Family
Closed

4
Beds
3
Total Baths
2,496
Sq. Ft.

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Sold

$1,400,000

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Closed

5
Beds
5
Total Baths
2,852
Sq. Ft.

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Sold by William Pitt Sotheby's Int'l

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Sold

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Single Family
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3
Beds
4
Total Baths
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Sq. Ft.

Listed by William Pitt Sotheby's Int'l
Sold by William Pitt Sotheby's Int'l

508 West Wakefield Boulevard, Winchester, CT 06098 (MLS# 24024787) is a Single Family property that was sold at $1,575,000 on June 30, 2025. Want to learn more about 508 West Wakefield Boulevard? Do you have questions about finding other Single Family real estate for sale in Winchester? You can browse all Winchester real estate or contact a Coldwell Banker agent to request more information.

508 W Wakefield Blvd Winchester, CT 06098