Nestled along the coveted east side of Highland Lake, 660 East Wakefield Blvd offers a rare opportunity to create the waterfront retreat you've always imagined. Bursting with classic lake charm and timeless character, this home is ready for a new owner to make it their own and bring fresh vision to an unforgettable setting. Enjoy excellent water access for swimming, boating, kayaking, and lakeside living, including use of a semi-private boat launch that makes getting out on the water effortless. Positioned on the east shore, the property captures magnificent sunset views across the lake, where evening skies melt into the water like brushed copper and glass. Whether you're dreaming of a cozy seasonal getaway, a year-round lake home, or a stunning custom renovation, this property offers the perfect canvas to create the waterfront home of your dreams. Opportunities like this on Highland Lake don't come around often.
Under contract
$749,999
660 East Wakefield Boulevard, Winchester, CT 06098
2beds
1,320sqft
:
Get pre-qualified$5,023/mo
Single Family Residence
Built in 1960
0.27 Acres Lot
$790,800 Zestimate®
$568/sqft
$-- HOA
What's special
- 75 days |
- 77 |
- 0 |
Likely to sell faster than
Zillow last checked:
Listing updated:
Listed by:
Matthew L. Smith (631)478-5094,
Smith & DeGroat Real Estate 516-248-6905
Source: Smart MLS,MLS#: 24174215
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 2
- Bathrooms: 2
- Full bathrooms: 2
Primary bedroom
- Level: Main
Bedroom
- Level: Main
Dining room
- Level: Lower
Kitchen
- Level: Lower
Living room
- Level: Lower
Heating
- Hot Water, Electric
Cooling
- None
Appliances
- Included: Electric Cooktop, Refrigerator, Dishwasher, Washer, Dryer, Water Heater
Features
- Basement: Full,Garage Access,Partially Finished,Walk-Out Access,Liveable Space
- Attic: Access Via Hatch
- Number of fireplaces: 1
Interior area
- Total structure area: 1,320
- Total interior livable area: 1,320 sqft
- Finished area above ground: 1,320
Property
Parking
- Total spaces: 6
- Parking features: Attached, Driveway, Paved, Off Street
- Attached garage spaces: 2
- Has uncovered spaces: Yes
Features
- Levels: Multi/Split
- Has view: Yes
- View description: Water
- Has water view: Yes
- Water view: Water
- Waterfront features: Waterfront, Dock or Mooring
Lot
- Size: 0.27 Acres
- Features: Sloped
Details
- Parcel number: 925588
- Zoning: HLD
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Split Level
- Property subtype: Single Family Residence
Materials
- Vinyl Siding
- Foundation: Concrete Perimeter
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1960
Utilities & green energy
- Sewer: Public Sewer
- Water: Well
Community & HOA
HOA
- Has HOA: No
Location
- Region: Winchester
Financial & listing details
- Price per square foot: $568/sqft
- Tax assessed value: $420,000
- Annual tax amount: $12,251
- Date on market: 5/9/2026
Estimated market value
$790,800
$751,000 - $830,000
$2,672/mo
Price history
| Date | Event | Price |
|---|---|---|
| 6/2/2026 | Pending sale | $749,999$568/sqft |
Source:  Smart MLS #24174215 Report a problem | ||
| 5/21/2026 | Listed for sale | $749,999+226.1%$568/sqft |
Source: Smart MLS #24174215 Report a problem | ||
| 11/25/1996 | Sold | $230,000$174/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $12,251 +10.5% | $420,000 |
| 2024 | $11,084 | $420,000 |
| 2023 | $11,084 +21.1% | $420,000 +53.9% |
| 2022 | $9,151 | $272,830 |
| 2021 | $9,151 | $272,830 |
| 2020 | $9,151 | $272,830 |
| 2019 | $9,151 | $272,830 |
| 2018 | $9,151 -5.1% | $272,830 -5.1% |
| 2017 | $9,644 | $287,530 |
| 2016 | $9,644 +2.6% | $287,530 |
| 2015 | $9,402 +2.5% | $287,530 |
| 2014 | $9,175 +2.3% | $287,530 |
| 2013 | $8,971 +5.5% | $287,530 -14% |
| 2012 | $8,503 | $334,360 |
| 2011 | $8,503 | $334,360 |
| 2010 | $8,503 +3.1% | $334,360 |
| 2009 | $8,249 | $334,360 |
| 2008 | $8,249 +5.8% | $334,360 +47% |
| 2007 | $7,796 +2.8% | $227,500 |
| 2006 | $7,585 +1.1% | $227,500 |
| 2005 | $7,503 +9.5% | $227,500 |
| 2003 | $6,852 +49.2% | $227,500 +36.6% |
| 1995 | $4,591 | $166,570 |
Find assessor info on the county website
Monthly payment
Est. payment
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.Climate risks
Neighborhood: 06098
Getting around
7 / 100
Car-DependentNearby schools
GreatSchools rating
- NABatcheller Early Education CenterGrades: PK-2Distance: 1.6 mi
- NAPearson AcademyGrades: Distance: 2.5 mi
- 6/10Pearson Middle SchoolGrades: 2-6Distance: 2.5 mi
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A local agent can set up tours, give advice and negotiate with sellers.
A local lender can help you make sure your offer is ready when you are.
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