Date
Details
Price
Change
Source
3/19/2026
Listed
$1,799,000
—
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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Join us at 58 Jefferson Road on:
- Open House: 11:00 AM - 12:30 PM
Sunday 3/22 11:00 AM - 12:30 PM
58 Jefferson Road,Winchester, MA 0189058 Jefferson RoadWinchesterMA01890
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Property Description
This well-maintained colonial is tucked at the end of a cul-de-sac in a very desirable neighborhood. Upon entering, the bright foyer with hardwood floors opens to a spacious front to back living room. The formal dining room leads to the eat in kitchen, perfect for entertaining and gatherings. Just off the kitchen the family room features a stone fireplace and sliding doors leading to the deck and backyard - perfect for relaxing and entertaining. A convenient half bath with laundry hookups completes the first floor. Upstairs are four generously sized bedrooms and two full baths, including a primary suite with access to an open loft overlooking the family room - ideal for a home office or bonus space. The home also offers a large, dry basement high ceilings and potential for additional living space. Many updates including newer roof, heating system, A/C, windows, siding and more! Close to the shops and restaurants of Winchester Center, commuter rail access, and the Fells Reservation.
Full Property Details
Full Property Details for 58 Jefferson Rd
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General
- Price: $1,799,000
- Taxes: $20,050 (2025)
- Status: Active
- Type: Single Family
- MLS ID: 73488901
- Updated: 3/19/2026
- Added to Site: 1 day(s) ago
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 2
- Half Bathrooms: 1
- Bathroom 1: 8.00 x 5.50, First
- Bathroom 2: 9.50 x 7.80, Second
- Bathroom 3: 7.80 x 7.40, Second
Bedrooms
- Total Bedrooms: 4
- Primary Bedroom: 17.20 x 11.30, Second
- Bedroom 2: 13.60 x 10.10, Second
- Bedroom 3: 12.10 x 11.70, Second
- Bedroom 4: 11.70 x 9.80, Second
Other Rooms
- Living Room: 25.20 x 13.60, First
- Family Room: 23.40 x 20.60, First
- Kitchen: 14.10 x 11.40, First
- Dining Room: 13.50 x 11.30, First
Parking
- Garage: Yes
- Garage Spaces: 2
- Parking Features: Attached, Under, Garage Door Opener, Storage, Paved Drive, Off Street, Paved
Location
- County: Middlesex
Structural Information
- Architectural Style: Colonial
- Basement: Yes
- Square Feet: 2,910
- Year Built: 1984
Lot Features
- Lot Size (Acres): 0.44
Financial Considerations
- Tax Amount: $20,050
- Tax Year: 2025
Disclosures and Reports
- Disclosures/Rstr.: All measurements are approximate. Bedroom and Loft photos are virtually staged. Front post light and two exterior ground lights are not working.
- Property ID: M:006 B:0449 L:0, 896196
Listed by Wilson Wolfe Real Estate, Stephanie Macfarland
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Listing agent
— 58 Jefferson Rd —
Stephanie Macfarland
Wilson Wolfe Real Estate
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 58 Jefferson Rd
School District:Winchester School District, Winchester, MA
| Name | Grades | Distance |
|---|---|---|
Lincoln Elementary School, Winchester, MA 161 Mystic Valley Parkway, Winchester, MA 01890 | K-5 | 0.8 mi |
Mccall Middle School 458 Main Street, Winchester, MA 01890 | 6-8 | 0.8 mi |
Winchester High School 80 Skillings Road, Winchester, MA 01890 | 9-12 | 1.1 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 58 Jefferson Rd
Tax History
Tax History for 58 Jefferson Rd
Year
Property Taxes
Change
Tax Assessment
Change
2025
$20,050
6%
$1,807,900
8%
2024
$18,966
1%
$1,674,000
6%
2023
$18,723
5%
$1,586,700
11%
2022
$17,839
2%
$1,426,000
5%
2021
$17,410
4%
$1,357,000
—
2020
$16,813
10%
$1,357,000
8%
2019
$15,242
3%
$1,258,600
4%
2018
$14,741
1%
$1,209,300
2%
2017
$14,533
7%
$1,183,500
2%
2016
$13,611
5%
$1,165,300
9%
2015
$12,989
5%
$1,069,900
10%
2014
$12,316
—
$972,800
—
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 58 Jefferson Rd
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- Single Family
- Active
- Updated 18 hours ago
- 4Beds
- 5Total Baths
- 3,906Sq. Ft.
- Single Family
- Active
- Updated 12 hours ago
- 4Beds
- 5Total Baths
- 3,700Sq. Ft.
- Single Family
- Active
- Updated 1 day ago
- 4Beds
- 3Total Baths
- 3,380Sq. Ft.
- Single Family
- Active
- Updated 4 days ago
- 4Beds
- 4Total Baths
- 3,000Sq. Ft.
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- Single Family
- Active
- Updated 2 days ago
- 6Beds
- 5Total Baths
- 3,880Sq. Ft.
Listed by AnnMarie Caldwell (781) 999-3430
- Single Family
- Active
- Updated 1 day ago
- 2Beds
- 2Total Baths
- 1,824Sq. Ft.
Listed by Edith Desmond (781) 820-7105
- Single Family
- Active
- Updated 11 hours ago
- 4Beds
- 2Total Baths
- 1,972Sq. Ft.
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- Single Family
- Active
- Updated 18 hours ago
- 3Beds
- 1Total Bath
- 1,403Sq. Ft.
Listed by Amie Pettengill (781) 962-0344
- Single Family
- Active
- Updated 3 days ago
- 4Beds
- 4Total Baths
- 3,829Sq. Ft.
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58 Jefferson Road, Winchester, MA 01890 (MLS# 73488901) is a Single Family property with 4 bedrooms, 2 full bathrooms and 1 partial bathroom. 58 Jefferson Road is currently listed for $1,799,000 and was received on March 19, 2026. Want to learn more about 58 Jefferson Road? 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.