406 E Wakefield Blvd, Winchester, CT 06098
Property image
Property image
OFF MARKET

$1,273,600

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 2,742 sqft (on 0.92 acres)

406 E Wakefield Blvd, Winchester, CT 06098

Est. Refi. Payment $8,702/mo*
Refinance Your Home
Currently Off Market - Sold Sep 3, 2020 for $854,700

Home Value

Trulia Estimate
$1.27M
Since last month
Decreased$7K (-0.5%)
Since last year
Decreased$17K (-1.3%)
Since last sale
Increased$416K (+48.6%)
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 +316% in the last 10 years
MonthEstimated value
2026
September 2026$1.27M
August 2026$1.27M
July 2026$1.28M
June 2026$1.31M
May 2026$1.24M
April 2026$1.25M
March 2026$1.22M
February 2026$1.22M
January 2026$1.21M
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
538 Wheelers Point, Winchester, CT
0.42
Single-Family Home
$1,500,000
10/14/25
4
3
2,496
424 East Wakefield Boulevard, Winsted, CT
0.16
Single-Family Home
$1,600,000
06/26/26
5
2
3,693
216 Perch Rock Trl, Winsted, CT
0.55
Single-Family Home
$1,000,000
01/12/26
4
2
2,557
121 West Wakefield Boulevard, Winsted, CT
0.89
Single-Family Home
$670,000
08/31/26
4
3.5
2,265
258 Perch Rock Trail, Winsted, CT
0.45
Single-Family Home
$925,000
06/04/26
4
2
1,373
351 Platt Hill Road, Winsted, CT
0.66
Single-Family Home
$370,000
04/17/26
3
2
1,715
126 Forest Avenue, Winsted, CT
0.77
Single-Family Home
$375,000
10/28/25
3
1.5
1,833
43 East Lake Street, Winsted, CT
0.93
Single-Family Home
$920,000
11/17/25
4
3
2,131
129 East Lake Street, Winsted, CT
1.02
Single-Family Home
$1,475,000
06/09/26
3
3.5
2,699
375 Platt Hill Rd, Winsted, CT
0.70
Single-Family Home
$370,000
02/11/26
3
1
2,033

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
414 East Wakefield Boulevard, Winsted, CT 06098
0.11
$850,000
-
-
-
For Sale
406 A East Wakefield Boulevard, Winsted, CT 06098
0.14
$1,320,700
4
2.5
1,282
Off Market
424 East Wakefield Boulevard, Winsted, CT 06098
0.16
$1,600,000
5
2
3,693
Recently Sold
347 West Wakefield Boulevard, Winsted, CT 06098
0.18
$289,000
2
1
596
For Sale
343 West Wakefield Boulevard, Winsted, CT 06098
0.19
$250,400
2
1
674
Off Market
339 West Wakefield Boulevard, Winsted, CT 06098
0.19
$575,500
3
2
1,322
Off Market
371 Norwood Road, Winsted, CT 06098
0.21
$193,400
1
1
592
Off Market
431 West Wakefield Boulevard, Winsted, CT 06098
0.34
$1,850,000
9
5.5
7,000
Recently Sold
435/434 West Wakefield Boulevard, Winsted, CT 06098
0.38
$1,283,200
8
4.5
5,231
Off Market
306 West Wakefield Boulevard, Winsted, CT 06098
0.36
$1,187,200
4
2.5
2,248
Off Market
421 Unity Place, Winsted, CT 06098
0.39
$306,000
3
2
1,440
Off Market
538 Wheelers Point, Winchester, CT 06098
0.42
$1,577,600
4
3
2,496
Off Market

Local Information

  • Map ViewExplore the area around 406 E Wakefield Blvd.
  • Schools1 Preschool School2 Elementary Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1940
0.92 acre lot
2,742 sqft
$464/sqft
Garage

About this House

Welcome to Eagle Point, sited on a private location on Highland Lake noted for its clean water. Pretty places to gather guests start at the deck. The nearby stone patio offers an outdoor dining area. The lawn is lush and is the perfect place for a game of corn hole. Guests and family will want to wander down to the shoreline and sit back in the shaded lounge area and take in the magnificent views of the lake. Beautiful renovation of this year round 4 bedroom, 3 full bath waterfront home began in 2015 and is situated in the heart of the Litchfield Hills at the gateway to the Berkshires in one of the most scenic sections of Connecticut. As you enter the mudroom with white washed brick floor you will fall in love with this special year round home. The kitchen is spacious and will remain unfinished so the buyer(s) can finish to their liking. The kitchen is enhanced by one wall of beautiful stone and local wide board pine floors. A walk in pantry is a bonus to the chef of the family and there is also a breakfast/dining area off the kitchen. The living room with its large windows provides peaceful and panoramic views of the lake and the mountains. Step out on the pressure treated deck and hear the sounds of nature - you are sure to spot the eagle landing in the tree as well as blue heron gliding across the lake. The family room is located off the kitchen and has a cathedral ceiling, stunning two story stone fireplace with sliders to the patio and lake views. A full bath and a separate laundry room complete the first floor. The second floor master bedroom is nicely sized and offers a cedar closet, a skylight and hardwood floors. Off the master bedroom you will find a spacious and light filled master bath with three Velux skylights and plumbed for a shower, double sink vanity and an additional walk in closet. Three additional bedrooms, one of which opens to a porch where your guests or family can take advantage of the views, a plumbed bath and plumbed laundry room complete this floor. New roof 2019, 200 amp electrical, all LED lights, two car attached garage. This spectacular property has approx 125 ft. of waterfront and sits on 0.92 acres. The attractive waterfront includes two platforms by water's edge with wonderful long range views of third bay. There is also a stone wading area for children or for your dog to cool off. Owner will install central air for buyer prior to closing. Seller is leaving the two second floor bathrooms plumbed and sheet rocked for the buyer to create their finishing touches. Plenty of parking which is a plus on the lake. Highland Lake is a 444 acre boating lake with over seven miles of shoreline and great fishing, swimming, kayaking and paddle boarding. Approx. 2 hrs. to NY, Boston, 30 minutes to Bradley International Airport. The property is easily reached from Rt. 8 & 44. Enjoy many great restaurants, shops, breweries, wineries, music halls, hiking trails and ski areas nearby. An additional 1.39 acre lot is available to be purchased at a separate price. Buyers can purchase now at this fantastic price. If Seller completes renovations in 2020 the list price will be adjusted accordingly.
406 E Wakefield Blvd, Winchester, CT 06098 is a 4 bedroom, 3 bathroom, 2,742 sqft single-family home built in 1940. It last sold for $854,700 on Sep 3, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,273,600, with a rent estimate of $3,312/month.

Home Details for 406 E Wakefield Blvd

Interior Features

Interior Details
BasementNumber of Rooms: 7Types of Rooms: Dining Room, Family Room
Heating & Cooling
Heating: BaseboardAir ConditioningHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: OtherDeckExterior: OtherGardenPatio
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1940
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 0.92 acres

Price and Tax history

DateEventPrice
Sep 3, 2020
Source: Smart MLS #170209084
Sold
$854,700
Aug 26, 2020
Source: Agent Provided
PendingToActive
$945,000
Jun 15, 2020
Source: Agent Provided
Pending
$945,000
Sep 2, 2019
Source: Agent Provided
Listed For Sale
$945,000
Sep 5, 2014
Source: Smart MLS #G668366
Sold
$55,000

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."
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Frequently asked questions about 406 E Wakefield Blvd

  • What is 406 E Wakefield Blvd estimated to be worth?
    Trulia's estimated value for 406 E Wakefield Blvd in Winchester, CT is $1,273,600.
  • What is the price history for 406 E Wakefield Blvd?
    406 E Wakefield Blvd in Winchester, CT last sold for $854,700 in September 2020.
  • 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 406 E Wakefield Blvd?
    The closest schools to 406 E Wakefield Blvd in Winchester, CT are Mary P. Hinsdale School (Pre-K/Elementary), Pearson Middle School (Elementary, rated 6/10).
  • How big is the lot at 406 E Wakefield Blvd?
    The lot at 406 E Wakefield Blvd in Winchester, CT is about 0.92 acres (40,075 sq ft).
  • Does 406 E Wakefield Blvd have a garage?
    Yes, 406 E Wakefield Blvd in Winchester, CT has a garage.

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