660 East Wakefield Boulevard, Winchester, CT 06098
SOLD
JUL 10, 2026

660 East Wakefield Boulevard
Winchester, CT 06098

  • 2 Beds
  • 2 Baths
  • 1,320 sqft (on 0.27 acres)

$750,000

Last Sold: Jul 10, 2026
0% over list $750K
$568/sqft
Est. Refi. Payment $5,064/mo*
Refinance Your Home

$750,000

Last Sold: Jul 10, 2026
0% over list $750K
$568/sqft
Est. Refi. Payment $5,064/mo*
Refinance Your Home
2 Beds
2 Baths
1,320 sqft
(on 0.27 acres)

Local Information

  • Map ViewExplore the area around 660 East Wakefield Boulevard.
  • Schools1 Preschool School3 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1960
Lot Size
0.27 acres
Living Area
1,320 sqft
Price/Sqft
$568/sqft
Parking
2 Car Garage

About this House

Nestled along the coveted east side of Highland Lake, 660 East Wakefield Blvd offers a rare opportunity to create the waterfront retreat you've always imagined. Bursting with classic lake charm and timeless character, this home is ready for a new owner to make it their own and bring fresh vision to an unforgettable setting. Enjoy excellent water access for swimming, boating, kayaking, and lakeside living, including use of a semi-private boat launch that makes getting out on the water effortless. Positioned on the east shore, the property captures magnificent sunset views across the lake, where evening skies melt into the water like brushed copper and glass. Whether you're dreaming of a cozy seasonal getaway, a year-round lake home, or a stunning custom renovation, this property offers the perfect canvas to create the waterfront home of your dreams. Opportunities like this on Highland Lake don't come around often.
660 East Wakefield Boulevard, Winchester, CT 06098 is a 2 bedroom, 2 bathroom, 1,320 sqft single-family home built in 1960. It last sold for the $749,999 asking price on Jul 10, 2026. It is currently off market. The Trulia Estimate is $774,900, with a rent estimate of $2,456/month.

Home Details for 660 East Wakefield Boulevard

Interior Features

Interior Details
Basement: Full,Garage Access,Partially Finished,Walk-Out Access,Liveable SpaceNumber of Rooms: 6Types of Rooms: Master Bedroom, Bedroom, Dining Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 2Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1320 Square Feet
Appliances & Utilities
Appliances: Electric Cooktop, Refrigerator, Dishwasher, Washer, Dryer, Water HeaterDishwasherDryerRefrigeratorWasher
Heating & Cooling
Heating: Hot Water,ElectricNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Hot Water
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace
Levels, Entrance, & Accessibility
Levels: Multi/Split
View
Has a ViewView: Water

Exterior Features

Exterior Home Features
Roof: AsphaltFoundation: Concrete PerimeterNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 6Parking: Attached,Driveway,Paved,Off Street
Frontage
WaterfrontWaterfront: Waterfront, Dock or MooringOn Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 1320 Square Feet

Property Information

Year Built
Year Built: 1960
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Split Level
Building
Construction Materials: Vinyl SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 925588

Price & Status

Price
List Price: $749,999Price Per Sqft: $568/sqft
Status Change & Dates
Off Market Date: Fri May 29 2026Possession Timing: Negotiable

Active Status

MLS Status: Closed

Location

Direction & Address
City: Winchester
School Information
Elementary School: Per Board of EdJr High / Middle School: Per Board of EdHigh School: Per Board of Ed

Building

Building Area
Building Area: 1320 Square Feet

HOA

No HOA

Lot Information

Lot Area: 0.27 acres

Miscellaneous

BasementMls Number: 24174215Attic: Access Via HatchWater ViewWater View: WaterAttribution Contact: (631) 478-5094Above Grade Unfinished Area: 1320Activation Date: Thu May 21 2026
Last check for updates: about 14 hours ago
Listed by Matthew L. Smith, (631) 478-5094
Smith & DeGroat Real Estate, (516) 248-6905
Bought with: Matthew L. Smith, (631) 478-5094, Smith & DeGroat Real Estate, (516) 248-6905
Source: Smart MLS, MLS#24174215

Price History for 660 East Wakefield Boulevard

DatePriceEventSource
07/10/2026$750,000Sold
Smart MLS #24174215
06/02/2026$749,999PendingSmart MLS #24174215
05/21/2026$749,999Listed For SaleSmart MLS #24174215
11/25/1996$230,000Sold
N/A

Market trends in Winchester

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
13
2MoM
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Property Tax and Assessment

Year2025
Tax$12,251
Assessment$420,000
Home facts updated by county records

Comparable Sales for 660 East Wakefield Boulevard

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
674 East Wakefield Boulevard, Winsted, CT
0.06
Single-Family Home
$1,050,000
06/18/26
3
3
2,097
722 Lake Drive, Winsted, CT
0.09
Single-Family Home
$1,200,000
05/20/26
3
2.5
1,556
736 West Wakefield Boulevard, Winsted, CT
0.48
Single-Family Home
$525,000
07/21/26
1
1.5
1,308
621 Wynne Road, Winsted, CT
0.11
Single-Family Home
$320,000
06/26/26
2
1
975
819 East Wakefield Boulevard, Winsted, CT
0.37
Single-Family Home
$439,900
12/04/25
3
1.5
1,892
817 East Wakefield Boulevard, Winsted, CT
0.36
Single-Family Home
$231,000
02/20/26
2
1
1,051
878 West Wakefield Boulevard, Winsted, CT
0.46
Single-Family Home
$1,200,000
07/07/26
4
3
3,330

Nearby homes

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Assigned Schools

These are the assigned schools for 660 East Wakefield Boulevard.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Winchester

At least 4 Trulia users voted on each feature.

  • 100 % Say people would walk alone at night

  • 89 % Say parking is easy

  • 80 % Say car is needed

  • 78 % Say it's quiet

  • 70 % Say yards are well-kept

  • 67 % Say there's wildlife

  • 64 % Say there's holiday spirit

  • 50 % Say it's dog friendly

  • 40 % Say it's walkable to grocery stores

  • 38 % Say neighbors are friendly

  • 36 % Say kids play outside

  • 33 % Say they plan to stay for at least 5 years

  • 33 % Say streets are well-lit

  • 33 % Say there are community events

  • 29 % Say it's walkable to restaurants

  • 11 % Say there are sidewalks

Sourced by Trulia users. Learn more about our methodology.
  • Carrie P.
    "The homes have big, spacious yards, and most people are dog owners. There is not a lot of traffic on the street."
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Apartments for Rent

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Homes for sale near 660 East Wakefield Boulevard

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Off Market Homes Near 660 East Wakefield Boulevard

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IDX information is provided exclusively for 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 not guaranteed.