Would people walk alone at night in Winchester, CT?

As of early 2026, 100% of users say people would walk alone at night

Is parking easy in Winchester, CT?

As of early 2026, 89% of users say parking is easy

Is a car needed in Winchester, CT?

As of early 2026, 80% of users say car is needed

Is Winchester, CT quiet?

As of early 2026, 78% of users say it's quiet

Are yards well-kept in Winchester, CT?

As of early 2026, 70% of users say yards are well-kept

Is there wildlife in Winchester, CT?

As of early 2026, 67% of users say there's wildlife

Does Winchester, CT show holiday spirit?

As of early 2026, 64% of users say there's holiday spirit

Is Winchester, CT dog-friendly?

As of early 2026, 50% of users say it's dog friendly

Is Winchester, CT walkable to grocery stores?

As of early 2026, 40% of users say it's walkable to grocery stores

Are neighbors friendly in Winchester, CT?

As of early 2026, 38% of users say neighbors are friendly

Do kids play outside in Winchester, CT?

As of early 2026, 36% of users say kids play outside

Do residents of Winchester, CT plan to stay at least 5 years?

As of early 2026, 33% of users say they plan to stay for at least 5 years

Are the streets well-lit in Winchester, CT?

As of early 2026, 33% of users say streets are well-lit

Are there community events in Winchester, CT?

As of early 2026, 33% of users say there are community events

Is Winchester, CT walkable to restaurants?

As of early 2026, 29% of users say it's walkable to restaurants

Does Winchester, CT have sidewalks?

As of early 2026, 11% of users say there are sidewalks

SOLD

DEC 4, 2025

819 East Wakefield Boulevard
Winsted, CT 06098

3 Beds
1.5 Baths
1,892 sqft (on 0.54 acres)

$439,900

Last Sold: Dec 4, 2025

$233/sqft

Est. Refi. Payment $2,980/mo*

Refinance Your Home

$439,900

Last Sold: Dec 4, 2025

$233/sqft

Est. Refi. Payment $2,980/mo*

Refinance Your Home

3 Beds

1.5 Baths

1,892 sqft

(on 0.54 acres)

Local Information

Map ViewExplore the area around 819 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

1920

Lot Size

0.54 acres

Living Area

1,892 sqft

Price/Sqft

$233/sqft

Parking

Garage

About this House

Perched directly across the street from Highland Lake's 3rd Bay, this charming 1,900 sq. ft. Cape offers sweeping lake views and the enjoyment of a permanent right-of-way to access the water. The home features 7 rooms, including 3 bedrooms and 1.5 baths, and has been thoughtfully maintained with important updates: new propane heating and hot water systems (2022), a new roof on both the house and garage (2023) along with a new skylight, and mini-splits for efficient cooling. A reverse osmosis system provides treated water for peace of mind. Inside, spacious living areas filled with natural light create the perfect setting for gatherings or quiet relaxation after a day on the lake. With its ideal location and solid upkeep, this home is move-in ready and waiting for its next owner to make it their own. There is a "right of way" for ingress and egress to the water.

819 East Wakefield Boulevard, Winsted, CT 06098 is a 3 bedroom, 2 bathroom, 1,892 sqft single-family home built in 1920. It last sold for the $439,900 asking price on Dec 4, 2025. More recently, it was listed as a rental in May 2012 with an asking price of $1,400 per month. That rental listing was removed on January 6, 2015. It is currently off market. The Trulia Estimate is $453,100, with a rent estimate of $3,283/month.

Home Details for 819 East Wakefield Boulevard

Interior Features
Interior Details Basement: Crawl Space,Partial,UnfinishedNumber of Rooms: 7Types of Rooms: Master Bedroom, Bedroom, Family Room, Kitchen, Living Room
Beds & Baths Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 1Number of Bathrooms (half): 1
Dimensions and Layout Living Area: 1892 Square Feet
Appliances & Utilities Appliances: Oven/Range, Refrigerator, Dishwasher, Washer, Dryer, Tankless Water HeaterDishwasherDryerRefrigeratorWasher
Heating & Cooling Heating: Forced Air,PropaneHas CoolingAir Conditioning: DuctlessHas HeatingHeating Fuel: Forced Air
Fireplace & Spa Number of Fireplaces: 1Has a Fireplace
View Has a ViewView: Water

Exterior Features
Exterior Home Features Roof: AsphaltPatio / Porch: Deck, PatioFoundation: Concrete Perimeter, StoneNo Private Pool
Parking & Garage Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageNo Attached GarageParking Spaces: 5Parking: Detached,Off Street,Garage Door Opener
Frontage Waterfront: Walk to Water, AccessNot on Waterfront
Water & Sewer Sewer: Public Sewer
Finished Area Finished Area (above surface): 1892 Square Feet

Property Information
Year Built Year Built: 1920
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Cape Cod
Building Construction Materials: Vinyl SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information Parcel Number: 926172

Price & Status
Price List Price: $439,900Price Per Sqft: $233/sqft
Status Change & Dates Off Market Date: Fri Oct 17 2025Possession Timing: Negotiable

Active Status
MLS Status: Closed

Location
Direction & Address City: WinchesterCommunity: Winsted
School Information Elementary School: Per Board of EdHigh School: Gilbert

Building
Building Area Building Area: 1892 Square Feet

HOA
No HOA

Lot Information
Lot Area: 0.54 acres

Miscellaneous
BasementMls Number: 24125218Attic: NoneWater ViewWater View: WaterAttribution Contact: (860) 806-0225Above Grade Unfinished Area: 1892Activation Date: Mon Sep 22 2025

Last check for updates: about 12 hours ago

Listed by David Sartirana, (860) 806-0225

Northwest CT Realty, (860) 379-7245

Bought with: Colleen E. Block, (860) 878-7917, Barile Realty Group, (860) 627-2885

Source: Smart MLS, MLS#24125218

Price History for 819 East Wakefield Boulevard

Date	Price	Event	Source
12/04/2025	$439,900	Sold	Smart MLS #24125218
Recording Date 12/04/2025 County Transfer Tax N/A Total Transfer Tax N/A
10/13/2025	$439,900	PriceChange	Smart MLS #24125218
Price Change $10,100 (-2%)
10/06/2025	$450,000	PriceChange	Smart MLS #24125218
Price Change $24,900 (-5%)
09/30/2025	$474,900	PriceChange	Smart MLS #24125218
Price Change $24,100 (-5%)
09/22/2025	$499,000	Listed For Sale	Smart MLS #24125218

06/27/2016	$147,000	Sold	Smart MLS #G10126162
Recording Date 06/27/2016 County Transfer Tax N/A Total Transfer Tax N/A
04/27/2016	$204,900	PriceChange	Agent Provided
Price Change $19,100 (-9%)
04/05/2016	$224,000	PriceChange	Agent Provided
Price Change $102,000 (84%)
03/03/2016	$122,000	PriceChange	Agent Provided
Price Change $2,000 (-2%)
02/09/2016	$124,000	PriceChange	Agent Provided
Price Change $7,000 (-5%)
02/05/2016	$131,000	PendingToActive	Agent Provided

02/03/2016	$131,000	Pending	Agent Provided

02/01/2016	$131,000	PendingToActive	Agent Provided

01/22/2016	$131,000	Pending	Agent Provided

01/18/2016	$131,000	PendingToActive	Agent Provided

01/08/2016	$131,000	Pending	Agent Provided

12/28/2015	$131,000	Listed For Sale	Agent Provided

01/06/2015	$1,500	ListingRemoved	Agent Provided

10/16/2014	$1,500	PriceChange	Agent Provided
Price Change $258,500 (-99%)
10/10/2014	$260,000	ListingRemoved	Agent Provided

05/12/2014	$260,000	Listed For Sale	Agent Provided

05/07/2013	$269,000	ListingRemoved	Agent Provided

04/17/2013	$269,000	Listed For Sale	Agent Provided

06/15/2012	$269,000	ListingRemoved	Agent Provided

05/23/2012	$269,000	Listed For Sale	Agent Provided

05/22/2012	$1,400	Listed For Rent	Agent Provided

08/30/2010	$312,300	Sold	N/A
Recording Date 08/30/2010 County Transfer Tax N/A Total Transfer Tax N/A
07/21/2003	$141,500	Sold	N/A
Recording Date 07/21/2003 County Transfer Tax N/A Total Transfer Tax N/A
03/11/2002	$46,000	Sold	Smart MLS #L101168
Recording Date 03/11/2002 County Transfer Tax N/A Total Transfer Tax N/A

Market trends in Winchester

Last updated June 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

2MoM

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Property Tax and Assessment

Year	2025
Tax	$7,865
Assessment	$269,640

Home facts updated by county records

Comparable Sales for 819 East Wakefield Boulevard

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
817 East Wakefield Boulevard, Winsted, CT	0.02	Single-Family Home	$231,000	02/20/26	2	1	1,051
107 Peck Road, Winsted, CT	0.24	Single-Family Home	$309,250	02/06/26	3	1	960
674 East Wakefield Boulevard, Winsted, CT	0.31	Single-Family Home	$1,050,000	06/18/26	3	3	2,097
621 Wynne Road, Winsted, CT	0.48	Single-Family Home	$320,000	06/26/26	2	1	975
126 Forest Avenue, Winsted, CT	0.82	Single-Family Home	$375,000	10/28/25	3	1.5	1,833
748 Lake Drive, Winsted, CT	0.20	Single-Family Home	$1,250,000	07/09/26	5	4	3,584

Nearby homes

Get a sense of prices in the area by checking nearby homes.

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SOLD
FEB 20, 2026
$231,000
2 bd
1 ba
1,051 sqft
817 East Wakefield Boulevard,
Winsted, CT 06098
DB Associates of CT, LLC
FOR SALE
0.41 ACRES
$59,900
105,107 Mountain Road,
Winsted, CT 06098
Northwest CT Realty
OFF MARKET
Est. $454,600
3 bd
2.5 ba
1,654 sqft
138 Mountain Road,
Winsted, CT 06098
William Raveis Real Estate
FOR SALE
1.18 ACRES
$158,000
843-845 (lots - 10A,10 &1 East wakefield Boulevard,
Winsted, CT 06098
Northwest CT Realty
OFF MARKET
Est. $338,700
2 bd
1 ba
1,249 sqft
143 Mountain Road,
Winsted, CT 06098
Berkshire Hathaway NE Prop.
OFF MARKET
Est. $618,300
3 bd
1 ba
816 sqft
756 Lake Drive,
Winsted, CT 06098
William Raveis Real Estate
FOR SALE
3D VIEW
0.38 ACRES
$1,600,000
4 bd
2.5 ba
2,129 sqft
752 Lake Drive,
Winsted, CT 06098
William Raveis Real Estate
SOLD
JUL 9, 2026
$1,250,000
5 bd
4 ba
3,584 sqft
748 Lake Drive,
Winsted, CT 06098
Smith & DeGroat Real Estate
SOLD
FEB 6, 2026
$309,250
3 bd
1 ba
960 sqft
107 Peck Road,
Winsted, CT 06098
W. Raveis Lifestyles Realty
OFF MARKET
Est. $397,600
3 bd
2 ba
2,148 sqft
152 Mountain Road,
Winsted, CT 06098
Northwest CT Realty
SOLD
MAY 20, 2026
$1,200,000
3 bd
2.5 ba
1,556 sqft
722 Lake Drive,
Winsted, CT 06098
The Washington Agency

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Additional Cost

Assigned Schools

These are the assigned schools for 819 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.
Resident
7y ago
"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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LGBTQ Local Legal Protections

Apartments for Rent

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PET FRIENDLY
$1,650/mo
Total price
2 bd
1 ba
1013F Whiting St #3F,
Winsted, CT 06098
PET FRIENDLY
$1,500/mo
Total price
1 bd
1 ba
101A Whiting St #1D,
Winsted, CT 06098
APPLY INSTANTLY
$2,125/mo
Total price
5 bd
1 ba
66 Bridge St #2,
Winsted, CT 06098
APPLY INSTANTLY
PET FRIENDLY
$1,650/mo
Total price
2 bd
1 ba
25 Hillside Ave #5,
Winsted, CT 06098
APPLY INSTANTLY
PET FRIENDLY
$1,450/mo
Total price
1 bd
1 ba
25 Hillside Ave #1,
Winsted, CT 06098
APPLY INSTANTLY
PET FRIENDLY
$1,500/mo
Fees may apply
3 bd
1 ba
25 Center St #3,
Winsted, CT 06098
APPLY INSTANTLY
PET FRIENDLY
$1,345/mo
Total price
2 bd
1 ba
21 Greenwoods Ave #4,
Winsted, CT 06098
NEW - 1 DAY AGO
PET FRIENDLY
$1,000/mo
Total price
2 bd
1 ba
69 Prospect St #3,
Winsted, CT 06098
PET FRIENDLY
$1,225/mo
Total price
2 bd
1 ba
111 Rockwell St #A,
Winsted, CT 06098
PET FRIENDLY
$1,400/mo
Total price
1 bd
1 ba
101C4 Whiting St #C4,
Winsted, CT 06098
PET FRIENDLY
$1,500/mo
Total price
1 bd
1 ba
A101 Whiting St #1D,
Winsted, CT 06098
NEW - 2 DAYS AGO
$1,400/mo
Fees may apply
2 bd
1 ba
398 Main St #11,
Winsted, CT 06098
PET FRIENDLY
$1,295/mo
Fees may apply
1 bd
1 ba
106 Rockwell St #1,
Winsted, CT 06098
PET FRIENDLY
$1,595/mo
Fees may apply
4 bd
1.5 ba
112 Rockwell St #2,
Winsted, CT 06098
See more homes for rent in
Winsted
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Explore by feature - Pet Friendly

15 pet-friendly rentals in Winsted, CT

SPECIAL OFFER
PET FRIENDLY
$1,150 - $1,350/mo
Fees may apply
Studio-2 bd
1-2 ba
Gilbert Clock Apartments | 13 Wallens St,
Winsted, CT 06098
PET FRIENDLY
$1,650/mo
Total price
2 bd
1 ba
800 sqft
1013F Whiting St #3F,
Winsted, CT 06098
PET FRIENDLY
$1,500/mo
Total price
1 bd
1 ba
600 sqft
101A Whiting St #1D,
Winsted, CT 06098
APPLY INSTANTLY
PET FRIENDLY
ROOM FOR RENT
$950/mo
Total price
4 bd
1 ba
Room for rent
14 Curtice St,
Winsted, CT 06098
APPLY INSTANTLY
PET FRIENDLY
$1,450/mo
Total price
1 bd
1 ba
900 sqft
25 Hillside Ave #1,
Winsted, CT 06098
APPLY INSTANTLY
PET FRIENDLY
$1,500/mo
Fees may apply
3 bd
1 ba
1,000 sqft
25 Center St #3,
Winsted, CT 06098
APPLY INSTANTLY
PET FRIENDLY
$1,345/mo
Total price
2 bd
1 ba
21 Greenwoods Ave #4,
Winsted, CT 06098
NEW - 1 DAY AGO
PET FRIENDLY
$1,000/mo
Total price
2 bd
1 ba
69 Prospect St #3,
Winsted, CT 06098
PET FRIENDLY
$1,400/mo
Total price
1 bd
1 ba
101C4 Whiting St #C4,
Winsted, CT 06098
PET FRIENDLY
$1,500/mo
Total price
1 bd
1 ba
700 sqft
A101 Whiting St #1D,
Winsted, CT 06098

Homes for sale near 819 East Wakefield Boulevard

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$749,900
2 bd
1 ba
760 sqft
812 West Wakefield Boulevard,
Winsted, CT 06098
Smith & DeGroat Real Estate
OPEN SUN, 1-3PM
7.11 ACRES
$895,000
4 bd
2 ba
3,088 sqft
469 Platt Hill Road,
Winsted, CT 06098
Cohen Agency
OPEN SAT, 2-3PM
0.53 ACRES
$379,000
3 bd
1.5 ba
1,284 sqft
2466 Torringford West Street,
Torrington, CT 06790
Litchfield County Real Estate
3 ACRES
$1,850,000
9 bd
5.5 ba
7,000 sqft
431 West Wakefield Boulevard,
Winsted, CT 06098
Berkshire Hathaway NE Prop.
$389,900
3 bd
2 ba
1,820 sqft
132 East Lake Street,
Winsted, CT 06098
Showcase Realty, Inc.
See more homes for sale in
Winsted
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Off Market Homes Near 819 East Wakefield Boulevard

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SOLD
JUL 21, 2026
$525,000
1 bd
1.5 ba
1,308 sqft
736 West Wakefield Boulevard,
Winsted, CT 06098
Lakefront Living Realty, LLC
SOLD
JUL 20, 2026
$335,000
4 bd
2 ba
1,816 sqft
121 Wedgewood Drive,
Torrington, CT 06790
Coldwell Banker Realty
SOLD
JUL 17, 2026
$225,000
3 bd
2 ba
1,612 sqft
127 Old Farms Road #127,
Torrington, CT 06790
Lotus Realty Group, LLC.
SOLD
JUL 17, 2026
$590,000
2 bd
958 sqft
650 West Hill Road,
New Hartford, CT 06057
The Washington Agency
SOLD
JUL 17, 2026
$230,000
2 bd
1.5 ba
1,204 sqft
1229 Winsted Road #112,
Torrington, CT 06790
Dave Jones Realty, LLC
SOLD
JUL 16, 2026
$223,500
2 bd
1 ba
1,028 sqft
142 Cedar Lane,
Torrington, CT 06790
KW Legacy Partners
SOLD
JUL 16, 2026
$390,000
4 bd
2.5 ba
2,172 sqft
341 Mountain Laurel Lane,
Torrington, CT 06790
Hunter Real Estate, LLC
SOLD
JUL 15, 2026
$420,000
5 bd
3 ba
2,779 sqft
217 Walnut Street,
Winsted, CT 06098
Northwest CT Realty
SOLD
JUL 10, 2026
$475,000
4 bd
2.5 ba
3,556 sqft
5 Stadler Heights,
Winsted, CT 06098
Northwest CT Realty
SOLD
JUL 10, 2026
$335,000
3 bd
1.5 ba
1,466 sqft
405 North Main Street,
Winsted, CT 06098
Berkshire Hathaway NE Prop.
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Winsted
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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.

819 East Wakefield Boulevard
Winsted, CT 06098

$439,900

$439,900