121 West Wakefield Boulevard Winchester, CT $ 769,000
121 West Wakefield Boulevard
$ 769,000
Share Save

121 West Wakefield Boulevard

Winchester, CT, 06098
$ 769,000
Bedrooms4 Baths3.1 Sq 2,265

Monthly Estimate*

$ 4,735

121 West Wakefield Boulevard, Winchester, CT 06098 - Image 1
121 West Wakefield Boulevard, Winchester, CT 06098 - Image 2
121 West Wakefield Boulevard, Winchester, CT 06098 - Image 3
121 West Wakefield Boulevard, Winchester, CT 06098 - Image 4
121 West Wakefield Boulevard, Winchester, CT 06098 - Image 5
121 West Wakefield Boulevard, Winchester, CT 06098 - Image 6
121 West Wakefield Boulevard, Winchester, CT 06098 - Image 7
121 West Wakefield Boulevard, Winchester, CT 06098 - Image 8
121 West Wakefield Boulevard, Winchester, CT 06098 - Image 9
121 West Wakefield Boulevard, Winchester, CT 06098 - Image 10
121 West Wakefield Boulevard, Winchester, CT 06098 - Image 11
121 West Wakefield Boulevard, Winchester, CT 06098 - Image 12
121 West Wakefield Boulevard, Winchester, CT 06098 - Image 13
121 West Wakefield Boulevard, Winchester, CT 06098 - Image 14
121 West Wakefield Boulevard, Winchester, CT 06098 - Image 15
121 West Wakefield Boulevard, Winchester, CT 06098 - Image 16
121 West Wakefield Boulevard, Winchester, CT 06098 - Image 17
121 West Wakefield Boulevard, Winchester, CT 06098 - Image 18
121 West Wakefield Boulevard, Winchester, CT 06098 - Image 19
121 West Wakefield Boulevard, Winchester, CT 06098 - Image 20
121 West Wakefield Boulevard, Winchester, CT 06098 - Image 21
121 West Wakefield Boulevard, Winchester, CT 06098 - Image 22
121 West Wakefield Boulevard, Winchester, CT 06098 - Image 23
121 West Wakefield Boulevard, Winchester, CT 06098 - Image 24
121 West Wakefield Boulevard, Winchester, CT 06098 - Image 25
121 West Wakefield Boulevard, Winchester, CT 06098 - Image 26
121 West Wakefield Boulevard, Winchester, CT 06098 - Image 27
121 West Wakefield Boulevard, Winchester, CT 06098 - Image 28
121 West Wakefield Boulevard, Winchester, CT 06098 - Image 29
121 West Wakefield Boulevard, Winchester, CT 06098 - Image 30
121 West Wakefield Boulevard, Winchester, CT 06098 - Image 31
121 West Wakefield Boulevard, Winchester, CT 06098 - Image 32
121 West Wakefield Boulevard, Winchester, CT 06098 - Image 33
121 West Wakefield Boulevard, Winchester, CT 06098 - Image 34
121 West Wakefield Boulevard, Winchester, CT 06098 - Image 35
121 West Wakefield Boulevard, Winchester, CT 06098 - Image 36
121 West Wakefield Boulevard, Winchester, CT 06098 - Image 37
121 West Wakefield Boulevard, Winchester, CT 06098 - Image 38

Single Family Home for sale in Winchester, CT

for $769,000 with 4 bedrooms and 3 full baths, 1 half bath. This 2,265 square foot home was built in 1996 on a lot size of 1.

Discover unparalleled Highland Lake living with this exceptional 1.00-acre retreat, boasting 50 feet of direct lake frontage and a newly renovated dock/deck. Enjoy breathtaking water views from your sunroom, dining room, and multiple bedrooms within this versatile 4/5 bedroom home. A unique first-floor suite with a separate exterior entrance offers ideal flexibility as a main-floor master or in-law accommodation. The upper-level primary suite boasts a private balcony perfect for savoring morning coffee while overlooking the shimmering lake. Entertain effortlessly in the large private backyard space, complete with an expansive 2 tier deck and built-in fire pit. Recent major upgrades ensure worry free enjoyment, including a high-efficiency HVAC (2024), new roof (2022), new siding, exterior doors, added insulation, two remodeled baths, full interior paint, and newer carpet throughout. Extensive landscaping has been completed, including new front railings, leveling and removal of several large trees. Previously a successful Airbnb, this property offers abundant parking, a two-car garage, and dual laundry facilities. Embrace all seasons on Highland Lake - from summer boating and fishing, lake is stocked with trout and bass for fishing enthusiasts, to winter ice skating/fishing. Your lakeside dream awaits! All furniture and household items included. Ring camera is active on exterior. Additional Tax bill for private waterfront is $523 p/y

See more

Single Family Coming Soon

Price

$ 769,000

Bedrooms

4

Full Bath

3

Half Bath

1

Property Type

Single Family

Taxes

$ 10,273

Style

Lot Size

1

Year Built

1996

Town/City

Winchester

MLS | Web ID

24159801

Features
General
Zoning HLD
Neighborhood N/A
County Litchfield
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Coming Soon
Acres 1
Directions Nav friendly
High School Per Board of Ed
City Winchester
Elementary School Per Board of Ed
Sq Ft Total 2265
Year Built 1996
Style Colonial
Year Built Source Public Records
Energy Features Programmable Thermostat Storm Doors Thermopane Windows
See more
Interior
Cooling System Central Air
Total Rooms 8
Basement Description Full
See more
Exterior
Water Source Public Water Connected
Lot Description Rear Lot Lightly Wooded Sloping Lot
See more
* Excluded Features
List By
Elizabeth Stockwell

Listing Agent

Coldwell Banker Realty

Broker

liz.stockwell@cbrealty.com

Email

Affordability Calculator

$5,591
Per Month
85%
15%
0%
Monthly Principal & Interest
$4,735
Monthly Property Taxes
$856
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save

Discover how much house you can afford

Your dream home may be within reach.

Learn More about how to save

The time to sell is now
THE TIME TO SELL IS NOW! What's my home worth?
Nearby
3092524 Elementary School
1232933 Middle School
Per Board of Ed High School High School
Pricing History
DatePricePrice ChangeDescription
4/2/2026$769,000 Listed Price

Map


See all

121 West Wakefield Boulevard, Winchester, CT, 06098 is a Single Family Home for sale at $769,000 with 2,265 sqft and a lot size of 1. 121 West Wakefield Boulevard has 4 bedrooms, 3.1 baths, and was built in 1996. The property's zip code is 06098 which is in Winchester, CT