414 East Wakefield Boulevard, Winsted, CT 06098
FOR SALE
0.9 ACRES

$850,000

    414 East Wakefield Boulevard, Winsted, CT 06098

    Est. Mortgage $5,746/mo*
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    Home Highlights

    Lot/Land
    0.9 acre lot
    Garage

    Local Information

    • Map ViewExplore the area around 414 East Wakefield Boulevard.
    • Schools1 Preschool School2 Elementary Schools
    • Shop & Eat
    -- mins to
    Commute Destination

    About this House

    An exceptional opportunity to create your dream home on the shores of highly sought-after Highland Lake. This waterfront property at 414 E Wakefield Boulevard offers the perfect setting to bring your vision of lakefront living to life. Existing plans for an impressive approximately 4,000-square-foot waterfront home are available, giving you the option to move forward with an already thoughtfully designed residence-or start fresh and create a custom home uniquely your own. Imagine walls of glass framing spectacular lake views, expansive outdoor living spaces, and your own private waterfront just steps from your door. Whether you envision a sophisticated year-round residence or an unforgettable family lake retreat, this property offers the rare opportunity to design around the lifestyle you've always wanted. You have the location. You have the lake. Now create the dream.
    Last check for updates: about 9 hours ago
    Listing courtesy of Annie Simard, (860) 841-2633
    LPT Realty, (860) 841-2633
    Source: Smart MLS, MLS#24196886
    Also Listed on Smart MLS.

    Home Details for 414 East Wakefield Boulevard

    Interior Features

    Appliances & Utilities
    Utilities: Electricity Available
    Gas & Electric
    Has Electric on Property
    View
    Has a ViewView: Water

    Exterior Features

    Exterior Home Features
    Other Structures: Garage(s)
    Parking & Garage
    Has a GarageParking: Garage
    Frontage
    WaterfrontWaterfront: Waterfront, Lake, Walk to Water, Dock or Mooring, Water Community, AccessRoad Surface Type: PavedOn Waterfront
    Water & Sewer
    Sewer: Public Sewer
    Farm & Range
    Frontage Length: 160

    Days on Market

    Days on Market: 5

    Property Information

    Property Type / Style
    Property Type: LandProperty Subtype: Unimproved Land
    Property Information
    Parcel Number: 924846

    Price & Status

    Price
    List Price: $850,000
    Status Change & Dates
    Possession Timing: Negotiable

    Active Status

    MLS Status: Active

    Location

    Direction & Address
    City: Winchester
    School Information
    Elementary School: Per Board of EdHigh School: Per Board of Ed

    Agent Information

    Listing Agent
    Listing ID: 24196886

    HOA

    No HOA

    Lot Information

    Lot Area: 0.90 acres

    Miscellaneous

    Mls Number: 24196886Water ViewWater View: WaterAttribution Contact: (860) 841-2633

    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
      Flag

    Market trends in Winchester

    Last updated July 2026
    Buyer'sMarketSeller'sMarket
    Avg. sale price
    —
    Sale-to-List Price
    —
    Price per sq ft
    —
    Available listings
    10
    3    MoM

    Home Value

    Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.

    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
    130 Alpha Avenue, Winsted, CT
    0.58
    Lot/Land
    $29,000
    11/11/25
    -
    -
    624 Wynne Road, Winsted, CT
    0.93
    Lot/Land
    $75,000
    08/19/26
    -
    -
    124 Rockwell Street, Winsted, CT
    1.23
    Lot/Land
    $26,500
    07/31/26
    -
    1,882
    48 Bridge Street, Winsted, CT
    1.35
    Lot/Land
    $27,000
    04/10/26
    -
    1,428
    99 Hubbard Street, Winsted, CT
    1.62
    Lot/Land
    $40,000
    07/22/26
    -
    832
    256 Colebrook Road, Winsted, CT
    2.69
    Lot/Land
    $33,500
    03/20/26
    -
    -
    52 White Street, Winsted, CT
    2.47
    Lot/Land
    $30,000
    02/20/26
    -
    -
    Hayden Hill Road, Torrington, CT
    2.93
    Lot/Land
    $34,000
    03/24/26
    -
    -
    4 West Side Drive, Barkhamsted, CT
    2.97
    Lot/Land
    $12,000
    06/18/26
    -
    -
    12 Hilltop Road, New Hartford, CT
    3.26
    Lot/Land
    $105,000
    08/14/26
    -
    -

    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
    406 A East Wakefield Boulevard, Winsted, CT 06098
    0.04
    $1,320,700
    4
    2.5
    1,282
    Off Market
    424 East Wakefield Boulevard, Winsted, CT 06098
    0.05
    $1,600,000
    5
    2
    3,693
    Recently Sold
    371 Norwood Road, Winsted, CT 06098
    0.22
    $193,400
    1
    1
    592
    Off Market
    421 Unity Place, Winsted, CT 06098
    0.28
    $306,000
    3
    2
    1,440
    Off Market
    347 W. Wakefield Boulevard, Winsted, CT 06098
    0.26
    $289,000
    2
    1
    596
    For Sale
    343 West Wakefield Boulevard, Winsted, CT 06098
    0.28
    $250,400
    2
    1
    674
    Off Market
    538 Wheelers Point, Winchester, CT 06098
    0.32
    $1,577,600
    4
    3
    2,496
    Off Market
    339 West Wakefield Boulevard, Winsted, CT 06098
    0.29
    $575,500
    3
    2
    1,322
    Off Market
    431 West Wakefield Boulevard, Winsted, CT 06098
    0.32
    $1,850,000
    9
    5.5
    7,000
    Recently Sold
    533 Wheeler Point, Winsted, CT 06098
    0.36
    $698,400
    2
    1.5
    1,200
    Off Market
    435/434 West Wakefield Boulevard, Winsted, CT 06098
    0.36
    $1,283,200
    8
    4.5
    5,231
    Off Market

    Price and Tax history

    DateEventPrice
    Sep 3, 2026
    Source: Smart MLS #24196886
    		Listed For Sale
    $850,000
    Dec 1, 2020
    Source: Smart MLS #170343627
    		Sold
    $324,000
    Oct 19, 2020
    Source: Agent Provided
    		Pending
    $324,000
    Oct 8, 2020
    Source: Agent Provided
    		Listed For Sale
    $324,000
    Jan 14, 2020
    Source: Agent Provided
    		ListingRemoved
    $324,000

    LGBTQ Local Legal Protections

    Annie Simard, LPT Realty, (860) 841-2633
    Agent Phone: (860) 841-2633
    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.

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    Frequently asked questions about 414 East Wakefield Boulevard

    • How big is 414 East Wakefield Boulevard?
      414 East Wakefield Boulevard in Winsted, CT is about 0.90 acres (39,204 sq ft).
    • What is the price per acre for 414 East Wakefield Boulevard?
      414 East Wakefield Boulevard in Winsted, CT is listed at $850,000, or about $945K per acre.
    • What are the closest schools to 414 East Wakefield Boulevard?
      The closest schools to 414 East Wakefield Boulevard in Winsted, CT are Mary P. Hinsdale School (Pre-K/Elementary), Pearson Middle School (Elementary, rated 6/10).
    • What is the price history for 414 East Wakefield Boulevard?
      414 East Wakefield Boulevard in Winsted, CT last sold for $324,000 in December 2020.
    414 East Wakefield Boulevard, Winsted, CT 06098 is a lot/land. This property is currently available for sale and was listed by Smart MLS on Sep 3, 2026. The MLS # for this home is MLS# 24196886.