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

$760,400

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

660 East Wakefield Boulevard, Winchester, CT 06098

Est. Refi. Payment $5,226/mo*
Refinance Your Home
Currently Off Market - Sold Jul 10, 2026 for $750,000 (0% above list price)

Home Value

Trulia Estimate
$760K
Since last month
Increased$12K (+1.6%)
Since last year
Increased$83K (+12.1%)
Since last sale
Increased$15K (+2%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +104% in the last 10 years
MonthEstimated value
2026
August 2026$765K
August 2026$760K
July 2026$753K
June 2026$785K
May 2026$776K
April 2026$668K
March 2026$613K
February 2026$621K
January 2026$651K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
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

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
674 East Wakefield Boulevard, Winsted, CT 06098
0.06
$1,050,000
3
3
2,097
Recently Sold
659 East Wakefield Boulevard, Winsted, CT 06098
0.05
$203,500
1
1
400
Off Market
722 Lake Drive, Winsted, CT 06098
0.09
$1,200,000
3
2.5
1,556
Recently Sold
624 Wynne Road, Winsted, CT 06098
0.08
$75,000
-
-
-
Recently Sold
638 & 640 Jewel Rd, Winsted, CT 06098
0.11
-
-
-
-
Off Market
621 Wynne Road, Winsted, CT 06098
0.11
$320,000
2
1
975
Recently Sold
748 Lake Drive, Winsted, CT 06098
0.20
$1,250,000
5
4
3,584
Recently Sold
752 Lake Drive, Winsted, CT 06098
0.22
$1,600,000
4
2.5
2,129
For Sale
756 Lake Drive, Winsted, CT 06098
0.23
$615,300
3
1
816
Off Market
630 East Wakefield Boulevard, Winsted, CT 06098
0.21
$1,279,100
3
2
2,320
Off Market
600 East Wakefield Boulevard, Winsted, CT 06098
0.23
$649,900
2
1
1,361
For Sale

Local Information

  • Map ViewExplore the area around 660 East Wakefield Boulevard.
  • Schools1 Preschool School2 Elementary Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1960
0.27 acre lot
1,320 sqft
$568/sqft
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. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $760,400, with a rent estimate of $2,164/month.
Last check for updates: about 7 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

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

Price and Tax history

DateEventPrice
Jul 10, 2026
Source: Smart MLS #24174215
Sold
$750,000
Jun 2, 2026
Source: Smart MLS #24174215
Pending
$749,999
May 21, 2026
Source: Smart MLS #24174215
Listed For Sale
$749,999
Nov 25, 1996
Source: N/A
Sold
$230,000

Market trends in Winchester

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
9
1MoM

Around this home

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."
    0
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Frequently asked questions about 660 East Wakefield Boulevard

  • What is 660 East Wakefield Boulevard estimated to be worth?
    Trulia's estimated value for 660 East Wakefield Boulevard in Winchester, CT is $760,400.
  • What is the price history for 660 East Wakefield Boulevard?
    660 East Wakefield Boulevard in Winchester, CT last sold for $750,000 in July 2026.
  • Is Winchester a buyer's or seller's market?
    Winchester is currently a seller's market, based on recent for-sale activity.
  • What are the closest schools to 660 East Wakefield Boulevard?
    The closest schools to 660 East Wakefield Boulevard in Winchester, CT are Mary P. Hinsdale School (Pre-K/Elementary), Pearson Middle School (Elementary, rated 6/10).
  • Does 660 East Wakefield Boulevard have laundry facilities?
    Yes, 660 East Wakefield Boulevard in Winchester, CT has in-unit laundry.
  • How big is the lot at 660 East Wakefield Boulevard?
    The lot at 660 East Wakefield Boulevard in Winchester, CT is about 0.27 acres (11,761 sq ft).

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