Date
Details
Price
Change
Source
4/06/2026
Listed
$2,299,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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$2,299,000 Just Listed
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Property Description
Discover this beautiful home with all the space you've been looking for! Set on a private half-acre lot in a serene cul-de-sac near the Winchester/Lexington border. This residence offers unparalleled privacy & is surrounded by nature. This home includes 5 bedrooms, 3.5 bathrooms & an oversized 3 car garage! The spacious grounds feature delightful front & back yards, a generous deck, & a charming gazebo, all beside Whipple Hill & Smith Pond w/ miles of walking trails nearby! Inside you will find a thoughtfully designed floor plan for every day living & entertaining featuring a sunken living room, sunny home office, lovely formal dining room & oversized family kitchen w dining area showcasing walls of windows overlooking the stunning rear yard & an adjacent family room w/ wood burning fireplace. The oversized primary suite incudes a walk in closet & spacious bath. Just 7 miles from Boston, Winchester is known for top-rated schools & great quality of life. Don't miss this fabulous home!
Full Property Details
Full Property Details for 276 High St
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General
- Price: $2,299,000
- Taxes: $23,217 (2025)
- Status: Active
- Type: Single Family
- MLS ID: 73496396
- Updated: 4/6/2026
- Added to Site: 1 day(s) ago
Rooms
Bathrooms
- Total Bathrooms: 4
- Full Bathrooms: 3
- Half Bathrooms: 1
- Bathroom 1: 8.00 x 5.00, First
- Bathroom 2: 13.00 x 12.00, Second
- Bathroom 3: 9.00 x 9.00, Second
Bedrooms
- Total Bedrooms: 5
- Primary Bedroom: 26.00 x 23.00, Second
- Bedroom 2: 17.00 x 14.00, Second
- Bedroom 3: 15.00 x 13.00, Second
- Bedroom 4: 14.00 x 12.00, Second
Other Rooms
- Living Room: 15.00 x 14.00, First
- Family Room: 30.00 x 22.00, First
- Kitchen: 16.00 x 15.00, Main, First
- Dining Room: 15.00 x 15.00, First
- Office: 14.00 x 11.00, First
Parking
- Garage: Yes
- Garage Spaces: 3
- Parking Features: Attached, Paved Drive, Off Street
Location
- County: Middlesex
Structural Information
- Architectural Style: Colonial
- Basement: Yes
- Square Feet: 5,006
- Year Built: 1992
Lot Features
- Lot Size (Acres): 0.46
Financial Considerations
- Tax Amount: $23,217
- Tax Year: 2025
Disclosures and Reports
- Disclosures/Rstr.: Common driveway entry then splits off
- Property ID: M:025 B:0146 L:0, 900972
Listed by Compass, Kim Covino & Co. Team and Kim Covino
We Value Your Privacy
We Value Your Privacy
We Value Your Privacy
Listing agents
— 276 High St —
Kim Covino & Co. Team
Compass
Kim Covino
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 276 High St
School District:Winchester School District, Winchester, MA
| Name | Grades | Distance |
|---|---|---|
Vinson-Owen Elementary School 75 Johnson Road, Winchester, MA 01890 | K-5 | 0.5 mi |
Mccall Middle School 458 Main Street, Winchester, MA 01890 | 6-8 | 2.4 mi |
Winchester High School 80 Skillings Road, Winchester, MA 01890 | 9-12 | 2.6 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 276 High St
Tax History
Tax History for 276 High St
Year
Property Taxes
Change
Tax Assessment
Change
2025
$23,217
4%
$2,093,500
6%
2024
$22,287
12%
$1,967,100
17%
2023
$19,841
10%
$1,681,400
17%
2022
$18,052
4%
$1,443,000
6%
2021
$17,417
4%
$1,357,500
—
2020
$16,819
2%
$1,357,500
—
2019
$16,439
3%
$1,357,500
3%
2018
$16,032
6%
$1,315,200
7%
2017
$15,131
7%
$1,232,200
2%
2016
$14,112
2%
$1,208,200
7%
2015
$13,768
-1%
$1,134,100
4%
2014
$13,848
—
$1,093,800
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 276 High St
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- Single Family
- Active
- Updated 1 day ago
- 5Beds
- 4Total Baths
- 3,981Sq. Ft.
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- Single Family
- Active
- Updated 19 hours ago
- 2Beds
- 2Total Baths
- 954Sq. Ft.
- Multi-Family
- Active
- Updated 10 hours ago
- 3Units
- 6Total Beds
- 0.17Acres
- Townhouse
- Active
- Updated 19 hours ago
- 3Beds
- 3Total Baths
- 2,330Sq. Ft.
Listed by Mark Lesses Group (617) 974-9275
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- Single Family
- Active
- Updated 10 hours ago
- 4Beds
- 4Total Baths
- 3,241Sq. Ft.
- Single Family
- Active
- Updated 16 hours ago
- 2Beds
- 1Total Bath
- 1,195Sq. Ft.
- Single Family
- Active
- Updated 19 hours ago
- 4Beds
- 5Total Baths
- 3,088Sq. Ft.
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276 High Street, Winchester, MA 01890 (MLS# 73496396) is a Single Family property with 5 bedrooms, 3 full bathrooms and 1 partial bathroom. 276 High Street is currently listed for $2,299,000 and was received on April 06, 2026. Want to learn more about 276 High Street? Do you have questions about finding other Single Family real estate for sale in Winchester Highlands? You can browse all Winchester Highlands real estate or contact a Coldwell Banker agent to request more information.