$799,900

804 W Wakefield Blvd Winsted, CT 06098

Winchester Area

Estimated payment $5,087/month

Total Views 3,472
2 Beds
1 Bath
1,044 Sq Ft
$766 Price per Sq Ft

Highlights

  • Waterfront
  • Deck
  • Patio
  • Open Floorplan
  • Ranch Style House
  • Solar Water Heater

About This Home

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. Located along the beautiful shores of Highland Lake in the foothills of the Berkshires, this exceptional location offers the best of Connecticut's four-season lifestyle. Highland Lake, one of the state's premier full-recreation lakes, stretches nearly three miles across more than 444 acres and is perfect for motorboating, kayaking, paddleboarding, swimming, and outstanding fishing, including trout. During the winter, the lake becomes a picturesque destination for ice skating, ice fishing, snowmobiling, and cross-country skiing. Just minutes away, downtown Winsted offers a variety of restaurants, cafes, shops, and everyday conveniences, while nearby Litchfield is known for its boutique shopping, acclaimed dining, and classic New England charm. Outdoor recreation abounds with Ski Sundown and Butternut Ski Area close by, along with popular destinations like Little Red Barn Brewers and Norbrook Farm Brewery. Conveniently situated near Routes 8 and 44, the property provides easy access to Hartford, Bradley International Airport, New Haven, and New York City. Whether you're looking for a full-time waterfront home, a vacation retreat, or an investment opportunity, this sought-after location combines natural beauty, year-round recreation, and everyday convenience.

Listing Agent

Pamela Dostilio

Coldwell Banker Realty Brokerage Phone: (860) 585-9381 License #RES.0812774 Listed on: 08/17/2026

Coldwell Banker Realty

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $8,341

Year Built

  • Built in 1924

Lot Details

  • 3,485 Sq Ft Lot
  • Waterfront
  • Stone Wall
  • Property is zoned HLD

Home Design

  • Ranch Style House
  • Cottage
  • Stone Foundation
  • Frame Construction
  • Asphalt Shingled Roof
  • Wood Siding

Interior Spaces

  • Open Floorplan
  • Unfinished Basement
  • Crawl Space
  • Oven or Range

Bedrooms and Bathrooms

  • 2 Bedrooms
  • 1 Full Bathroom

Laundry

  • Laundry on main level
  • Dryer
  • Washer

Parking

  • 5 Parking Spaces
  • Parking Deck
  • Driveway

Eco-Friendly Details

  • Energy-Efficient Insulation
  • Solar Water Heater
  • Solar Heating System
  • Off-Grid Solar Heating System
  • Active Solar Heating System

Outdoor Features

  • Deck
  • Patio
  • Exterior Lighting

Location

  • Property is near shops

Utilities

  • Split Air Conditioning
  • Wall Furnace
  • Heating System Mounted To A Wall or Window
  • Well
  • Tankless Water Heater
  • Cable TV Available

Listing and Financial Details

  • Assessor Parcel Number 925619

Home Details

Home Type

Single Family

Est. Annual Taxes

$8,341

Year Built

Built in 1924

Lot Details

3,485 Sq Ft Lot

Listing Details

  • Neighborhood: N/A
  • Property Type: Single Family For Sale
  • Style: Ranch, Cottage
  • Sq Ft Est Heated Above Grade: 638
  • Sq Ft Est Heated Below Grade: 406
  • Total Sq Ft: 1044
  • Year Built: 1924
  • New Construction: No/Resale
  • Nearby Amenities: Health Club, Lake, Park, Shopping/Mall
  • Remarks Public Addendum: Located along the beautiful shores of Highland Lake in the foothills of the Berkshires, this exceptional location offers the best of Connecticut's four-season lifestyle. Highland Lake, one of the state's premier full-recreation lakes, stretches nearly three miles across more than 444 acres and is perfect for motorboating, kayaking, paddleboarding, swimming, and outstanding fishing, including trout. During the winter, the lake becomes a picturesque destination for ice skating, ice fishing, snowmobiling, and cross-country skiing. Just minutes away, downtown Winsted offers a variety of restaurants, cafes, shops, and everyday conveniences, while nearby Litchfield is known for its boutique shopping, acclaimed dining, and classic New England charm. Outdoor recreation abounds with Ski Sundown and Butternut Ski Area close by, along with popular destinations like Little Red Barn Brewers and Norbrook Farm Brewery. Conveniently situated near Routes 8 and 44, the property provides easy access to Hartford, Bradley International Airport, New Haven, and New York City. Whether you're looking for a full-time waterfront home, a vacation retreat, or an investment opportunity, this sought-after location combines natural beauty, year-round recreation, and everyday convenience.
  • Direct Waterfront: Yes
  • Home Warranty Offered: No
  • Radon Mitigation Air Ynu: No
  • Radon Mitigation Water Ynu: No
  • Directions: GPS Friendly
  • In Law Apartment: No
  • Street Type: Boulevard
  • Office Attribution Contact: (203) 426-5679
  • Reserve Prospect: No
  • Special Features: None
  • Property Sub Type: Detached

Interior Features

  • Total Bedrooms: 2
  • Total Bathrooms: 1
  • Full Bathrooms: 1
  • Basement Description: Crawl Space, Unfinished
  • Interior Amenities: Cable - Available, Open Floor Plan
  • Appliances: Oven/Range, Refrigerator, Washer, Dryer
  • Laundry Room Info: Main Level
  • Attic: No

Exterior Features

  • Exterior Features: Deck, Lighting, Stone Wall, Patio
  • Exterior Siding: Wood
  • Foundation Type: Stone
  • Roof Information: Asphalt Shingle
  • Waterfront Description: Lake Beach Dock or Mooring Beach Rights View
  • Swimming Pool: No
  • Construction Description: Frame

Garage/Parking

  • Driveway Type: Paved
  • Total Parking Spaces: 5
  • Garage And Parking: Off Street Parking, Driveway

Utilities

  • Cooling System: Split System
  • Heat Type: Solar, Wall Unit, Other
  • Heat Fuel Type: Solar
  • Hot Water Description: Electric, Solar Assisted, Tankless Hotwater
  • Water Source: Private Well
  • Sewer: Public Sewer Connected

Schools

  • Intermediate School: Per Board of Ed

Green Features

  • Energy Features: Active Solar, Extra Insulation

Lot Info

  • Acres: 0.08
  • Lot Description: Level Lot Sloping Lot Professionally Landscaped Water View
  • Flood Zone: No
  • Zoning: HLD
  • Parcel #: 925619

Tax Info

  • Tax Year: July 2026-June 2027
  • Property Tax: 8341

MLS Schools

  • Elementary School: Per Board of Ed
  • Middle Jr High School: Per Board of Ed
  • High School: Per Board of Ed

Map

Range of Values:

--
Value Increase
--
Percent Increase
--
Adjusted for Inflation
Collateral Analytics

Collateral Analytics Collateral Analytics AVMs (Automated Valuation Model) employ a number of statistical approaches combined with neighborhood-specific comparable selection guarantees the most up-to-date and precise valuations.

Not Available

Collateral Analytics does not have data for the current month. Please view the chart for historical values.

ICE

ICE Mortgage Technology ICE Mortgage Technology’s AVM (Automated Valuation Model) is a state-of-the-art online residential property valuation tool that provides a quick and accurate estimate of the value of almost any home in the U.S.

Not Available

ICE Mortgage Technology does not have data for the current month. Please view the chart for historical values.

First American

First American First American Data & Analytics’ next-generation AVM combines unrivaled data assets with a blended ensemble of valuation models to produce highly accurate, reliable valuations you can trust.

Not Available

First American does not have data for the current month. Please view the chart for historical values.

Quantarium

Quantarium Quantarium’s valuation service, repeatedly proven the industry’s most accurate and comprehensive, is supercharged with a self-learning and auto-tuning AI engine that continually becomes smarter and more accurate as it processes daily inputs from the industry’s leading RE data lake.

Not Available

Quantarium does not have data for the current month. Please view the chart for historical values.

Average Value
Not Available
List Price
Sold Price
Create a Home Valuation Report for This Property
The Home Valuation Report is an in-depth analysis detailing your home's value as well as a comparison with similar homes in the area

Home Values in the Area

Source: Public Records

Average Home Value in this Area





Source: Public Records

Tax History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2025 $7,988 $273,840 $204,330 $69,510
2024 $7,459 $273,840 $204,330 $69,510
2023 $7,227 $273,840 $204,330 $69,510
2022 $5,373 $160,200 $119,740 $40,460
2021 $5,373 $160,200 $119,740 $40,460
2020 $5,305 $158,170 $119,740 $38,430
2019 $5,305 $158,170 $119,740 $38,430
2018 $5,305 $158,170 $119,740 $38,430
2017 $5,061 $150,890 $109,730 $41,160
2016 $5,061 $150,890 $109,730 $41,160
2015 $4,934 $150,890 $109,730 $41,160
2014 $4,815 $150,890 $109,730 $41,160
Source: Public Records

Property History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Event Price List to Sale Price per Sq Ft Prior Sale
08/17/2026 08/17/26 For Sale $799,900 +122.2% $766 / Sq Ft
01/31/2020 01/31/20 Sold $360,000 -10.0% $345 / Sq Ft View Prior Sale
11/19/2019 11/19/19 Pending -- -- --
10/16/2019 10/16/19 For Sale $399,900 -- $383 / Sq Ft
Source: SmartMLS

Purchase History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Type Sale Price Title Company
Warranty Deed $159,000 --
Source: Public Records

About the Listing Agent

Pamela Dostilio

Coldwell Banker Realty

(860) 772-0158

Section Image

Pamela is an award winning "Top 7% Nationally" Realtor with over 30+ years of 5 Star Client Services as well as marketing, administration and business experience. As a extremely dedicated multimillion-dollar agent, she consistently ranks at the top of her profession, thanks to both her clients and her peers. Pamela understands that buying or selling a home is a huge step in your life. You deserve a real estate agent who will focus on your needs and make your priorities her priorities. That's

Pamela's Other Listings

  • 485 Heritage Village Unit A, Southbury, CT 06488

    $229,900

    • 1 Bed
    • 1 Bath
    • 928 Sq Ft
    • 485 Heritage Village
    • Unit A
    • Southbury, CT

    Welcome to effortless living in this beautifully renovated Carriage House model in sought-after Heritage Village, Southbury's premier 55+ community. Thoughtfully updated throughout, this turnkey home offers modern style, comfort, and an exceptional lifestyle. Luxury vinyl plank flooring flows through the main living areas, while the spacious living room features a cozy fireplace, charming bay

    Pamela Dostilio Coldwell Banker Realty

    Section Image
  • 32 Pine Tree Hill Rd, Newtown, CT 06470

    $894,900

    • 4 Beds
    • 2.5 Baths
    • 3,923 Sq Ft
    • 32 Pine Tree Hill Rd
    • Newtown, CT

    Welcome to 32 Pine Tree Hill Road, an exquisite, meticulously maintained 4-bedroom, 2.5-bath center-hall Colonial offering privacy, elegance, and an ideal Newtown location. Set on over two acres surrounded by Newtown Forest Association open space, this exceptional home feels like a private retreat. A dramatic two-story foyer welcomes you with abundant natural light, rich hardwood floors, and

    Pamela Dostilio Coldwell Banker Realty

    Section Image
  • 34 Beardsley Rd, New Milford, CT 06776

    $700,000 Sold Jul 24, 2026

    • 4 Beds
    • 2.5 Baths
    • 2,624 Sq Ft
    • 34 Beardsley Rd
    • New Milford, CT

    Pristine 4 bedroom, 2.5 bath center hall Colonial located in the highly desirable Sun Pond Woods subdivision of New Milford. Set on 1.49 acres of beautifully maintained park-like property with a newer Trex deck perfect for entertaining, relaxing, and BBQs. Hardwood floors throughout with crown molding, recessed lighting, and abundant natural light. Chef's kitchen features white cabinetry, granite

    Pamela Dostilio Coldwell Banker Realty

  • 23 Rockridge Terrace, Prospect, CT 06712

    $525,000 Sold Jul 10, 2026

    • 4 Beds
    • 2.5 Baths
    • 2,314 Sq Ft
    • 23 Rockridge Terrace
    • Prospect, CT

    Welcome to 23 Rockridge Terrace, ideally located on a quiet cul-de-sac in Prospect, Connecticut known for its small-town charm. Set on a private, level 1-acre lot, this 4-bedroom, 2.5-bath Colonial offers the perfect blend of comfort and functionality. Enjoy outdoor living with a large back deck and a generous patio area ideal for entertaining or relaxing. Inside, the open kitchen features quartz

    Pamela Dostilio Coldwell Banker Realty

  • 42 Hine Hill Rd, New Milford, CT 06776

    $599,700 Sold Apr 14, 2026

    • 4 Beds
    • 2.5 Baths
    • 2,260 Sq Ft
    • 42 Hine Hill Rd
    • New Milford, CT

    Welcome to your new home! This charming 4-bedroom, 2-bathroom colonial is move-in ready, with a perfect blend of comfort and convenience in a highly sought-after New Milford location. Step inside to discover a freshly and professionally painted interior that enhances the home's warm and inviting ambiance. The beautifully refinished hardwood floors flow throughout, adding character and

    Pamela Dostilio Coldwell Banker Realty

  • 29 Heritage Village Unit B, Southbury, CT 06488

    $253,900 Sold May 28, 2026

    • 2 Beds
    • 2 Baths
    • 1,076 Sq Ft
    • 29 Heritage Village
    • Unit B
    • Southbury, CT

    Move right into this beautifully updated main-level Mark Twain model ideally located in a peaceful setting near the pond. This pristine 2-bedroom, 2-bath home offers effortless one-level living with a thoughtfully remodeled interior and timeless finishes throughout. The stunning kitchen has been beautifully renovated with white cabinetry, light colored granite countertops, stylish backsplash, and

    Pamela Dostilio Coldwell Banker Realty

  • 331 Heritage Village Unit E, Southbury, CT 06488

    $260,000 Sold May 01, 2026

    • 2 Beds
    • 1.5 Baths
    • 1,365 Sq Ft
    • 331 Heritage Village
    • Unit E
    • Southbury, CT

    LOCATION, LOCATION,LOCATION! Welcome to this beautiful end-unit Franklin model, ideally situated on a quiet cul-de-sac offering the feel of a private home rather than a condo. Enjoy two spacious levels with no foot traffic beside you, along with two private patios overlooking serene, wooded surroundings perfect for relaxing or entertaining. This home features brand new high-end luxury vinyl

    Pamela Dostilio Coldwell Banker Realty

  • 3 Josephs Ln, Brookfield, CT 06804

    $770,000 Sold Jun 26, 2026

    • 4 Beds
    • 2.5 Baths
    • 3,213 Sq Ft
    • 3 Josephs Ln
    • Brookfield, CT

    Situated on 2.88 private acres in one of Brookfield's most desirable cul-de-sac neighborhoods, this custom-built Colonial showcases exceptional craftsmanship and timeless design throughout. Built with superior 2x6 construction, this 4-bedroom, 2.5-bath home offers 3,213 sq ft of thoughtfully designed living space ideal for everyday living and entertaining. A dramatic two-story foyer welcomes you

    Pamela Dostilio Coldwell Banker Realty

  • 3 Gretl Ln, New Milford, CT 06776

    $466,000 Sold Aug 14, 2026

    • 4 Beds
    • 2 Baths
    • 1,908 Sq Ft
    • 3 Gretl Ln
    • New Milford, CT

    Highly desirable location! This 4-bedroom, 2-bath raised ranch offers 1,908 total square feet of comfortable living space set on a private 1.08-acre lot with seasonal mountain views. The bright and inviting interior features beautifully refinished hardwood floors, creating a warm and welcoming atmosphere throughout the home. The functional floor plan provides ample space for everyday living and

    Pamela Dostilio Coldwell Banker Realty

Source: SmartMLS

MLS Number: 24195283

SmartMLS

APN: WINC-000038-000111-000006

Your Personal Tour Guide

Ask me questions while you tour the home.