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$799,900

Under Contract

804 Wakefield Boulevard

Winchester, Connecticut, 06098 · Litchfield County

2

Beds

1

Baths

1,044

Sq Ft

1924

Built

MLS # 24195283

Price / Sq Ft

$766

Property Type

Single Family For Sale

Lot Size

0.08

Class

Property

About This Property

Experience an everyday vacation at 804 W. Wakefield Blvd on beautiful Highland Lake! This exceptional turnkey, year-round waterfront retreat is ideal as a primary residence, weekend escape, vacation home, or income-producing rental. Perfectly positioned on the widest part of Highland Lake's coveted Third Bay, enjoy breathtaking sunrises, panoramic water views, and bald eagles soaring overhead from your expansive lakeside deck. With over $100,000 in owner upgrades, this move-in ready home offers effortless lakefront living with a newer roof, owned solar panels, updated systems, a permanent grandfathered dock, seawall, outdoor shower, firepit, and direct access to motorboating, kayaking, paddleboarding, swimming, and outstanding fishing. A rare additional 0.24-acre lot across the street provides a total of 5 parking spaces perfect for family and guests. Enjoy easy access to Route 8, a short drive to Bradley International Airport, and year-round recreation with nearby Ski Sundown, Butternut Ski Area, scenic hiking trails, wineries, breweries, restaurants, and charming New England towns. This is your opportunity to own one of Highland Lake's most desirable waterfront homes-simply unpack, relax, and make every day feel like a vacation.

Property Details

804 Wakefield Boulevard, Winchester Connecticut 06098 — Single Family For Sale listed at $799,900.

At a Glance

2

Bedrooms

1

Bathrooms

1,044

Sq Ft

0.08

Lot Size

--

Garage

1924

Year Built

The Details

Property TypeSingle Family For Sale
NeighborhoodLitchfield
Address804 Wakefield Boulevard
MLS Number24195283
Year Built1924
Square Footage1,044
Lot Size0.08
Bedrooms2
Bathrooms1
Water SourcePrivate Well

Property Details

Other Details

Appliances IncludedOven/Range,Refrigerator,Washer,Dryer
ColorLight Wood
Lockbox Locationfront door
Parcel Number925619
Parking Total Spaces5
Virtual Tourhttps://vimeo.com/1218983029/230d5c6760?fl=ip&fe=ec&share=copy
ZoningHLD

Financial

Assessed Value278040
Mil Rate Total30
Property Tax8341
Tax YearJuly 2026-June 2027

Property Features

Basement DescriptionCrawl Space,Unfinished
Cooling SystemSplit System
Driveway TypePaved
Energy FeaturesActive Solar,Extra Insulation
Exterior FeaturesDeck,Lighting,Stone Wall,Patio
Exterior SidingWood
Foundation TypeStone
Garage ParkingOff Street Parking,Driveway
Heat Fuel TypeSolar
Heat TypeSolar,Wall Unit,Other
Hot Water DescriptionElectric,Solar Assisted,Tankless Hotwater
Interior FeaturesCable - Available,Open Floor Plan
Laundry Room InfoMain Level
Roof InformationAsphalt Shingle

All Photos (37)

Contact Pamela Dostilio

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Affordability Calculator

$799,900

Down Payment$159,980
Loan Amount$639,920
Principal & Interest$4,045/mo
Property Tax$800/mo
Insurance$100/mo
Est. Monthly$4,945/mo

Listing Agent

P

Pamela Dostilio

Coldwell Banker Realty

Quick Facts

StatusUnder Contract
TypeSingle Family For Sale
ClassProperty
MLS #24195283
Last Updated2026-09-18

Virtual Tour

Walk through 804 Wakefield Boulevard