414 East Wakefield Boulevard
Winchester, Connecticut 06098
- Beds
- 0
- Baths
- 0
- SqFt
- —
- Acres
- 0.90
- Property Type
- Land
Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
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.
Key Facts
- City/Town
- Winchester
- Neighborhood
- N/A
- Property Type
- Land
- Days on Market
- 0 days
- Beds
- 0
- Baths
- 0 baths
- Lot Size
- 0.90 acres
- Property Taxes
- $7,140 / Annually
Market Snapshot
The Winchester Market
Land · trailing 12 months
Active Listings
11
6 under contract
Median List Price
$295,000
11 active listings
Median Closed Price
$33,500
9 sales
Median Days on Market
101
11 active listings
Median $ / Sq Ft
--
11 active listings
Sale-to-List Ratio
84.0%
9 sales
How this home compares
List Price
$850,000
vs $295,000 median
2.9× the median
Price / Sq Ft
--
Median unavailable
Limited comparable data
Days on Market
0 days
vs 101 days median
101 days fresher than median
Based on 11 active and 9 closed sales (trailing 12 mo) of land in Winchester. Source: SmartMLS · As of September 4, 2026.
Location
414 East Wakefield Boulevard, Winchester, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 27, 2026per month
- Principal & Interest$4,370
- Property Taxes$595
- Insurance$283
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Winchester
- Neighborhood
- N/A
- County
- Litchfield
Residence
- Property Type
- Land
- Subtype
- SingleFamilyResidence
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Exterior & Lot
- Lot Size
- 0.90 acres
- Zoning
- HLD
- Waterfront
- Direct waterfront
- Waterfront Details
- LakeWalk to WaterDock or MooringWater CommunityViewAccess
- Water Source
- Private Well
- Sewer
- Public Sewer In Street
- Lot Description
- Sloping Lot
Listing & Financials
- Property Taxes
- $7,140 / Annually
- Days on Market
- 0
- MLS #
- 24196886
- MLS Status
- Active
Similar Properties
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 9/4/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 9/4/2026 at 4:00 AM UTC.