58 Jefferson Rd, Winchester, MA 01890
Property image
Property image
SOLD
APR 23, 2026

$2,063,800

Trulia Estimate
  • 4 Beds
  • 2.5 Baths
  • 2,910 sqft (on 0.44 acres)

58 Jefferson Rd, Winchester, MA 01890

Est. Refi. Payment $12,819/mo*
Refinance Your Home
Currently Off Market - Sold Apr 23, 2026 for $1,850,000 (3% above list price)

Home Value

Trulia Estimate
$2.06M
Since last month
Increased$249K (+13.4%)
Since last year
Increased$230K (+12.2%)
Since last sale
Increased$261K (+14.1%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +55% in the last 10 years
MonthEstimated value
2026
September 2026$2.11M
August 2026$2.02M
July 2026$1.86M
June 2026$1.84M
May 2026$1.85M
April 2026$1.85M
March 2026$1.97M
February 2026$1.87M
January 2026$1.84M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
22 Hollywood Rd, Winchester, MA
0.08
Single-Family Home
$2,150,000
07/13/26
5
3
3,136
17 Dennett Rd, Winchester, MA
0.17
Single-Family Home
$1,500,000
10/09/25
3
2.5
2,283
35 Hollywood Rd, Winchester, MA
0.17
Single-Family Home
$1,755,000
05/01/26
4
4.5
3,906
8 Felsdale Close, Winchester, MA
0.31
Single-Family Home
$1,930,000
01/09/26
4
2.5
3,658
4 Leslie Rd, Winchester, MA
0.27
Single-Family Home
$2,120,000
04/28/26
5
3.5
2,860
30 Prospect St, Winchester, MA
0.43
Single-Family Home
$2,450,000
12/16/25
4
3
2,519
17 Cranston Rd, Winchester, MA
0.27
Single-Family Home
$1,560,000
04/30/26
4
2.5
2,578
382 S Border Rd, Winchester, MA
0.04
Single-Family Home
$2,450,000
11/17/25
6
5.5
4,563
4 Sargent Rd, Winchester, MA
0.39
Single-Family Home
$1,355,000
11/20/25
4
2.5
2,865

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
57 Jefferson Rd, Winchester, MA 01890
0.03
$2,406,600
4
3.5
3,274
Off Market
94 Lawson Rd, Winchester, MA 01890
0.05
$2,327,400
5
4
5,484
Off Market
382 S Border Rd, Winchester, MA 01890
0.04
-
6
5.5
4,563
Off Market
22 Hollywood Rd, Winchester, MA 01890
0.08
$2,150,000
5
3
3,136
Recently Sold
17 Dennett Rd, Winchester, MA 01890
0.17
$1,542,100
3
2.5
2,283
Off Market
10 Clearwater Rd, Winchester, MA 01890
0.18
$2,017,800
4
2.5
2,688
Off Market
35 Hollywood Rd, Winchester, MA 01890
0.17
$1,755,000
4
4.5
3,906
Recently Sold
350 S Border Rd, Winchester, MA 01890
0.18
$1,705,900
3
2.5
2,240
Off Market
5 Clearwater Rd, Winchester, MA 01890
0.20
$2,942,800
6
7.5
5,658
Off Market
22 Willowdale Rd, Winchester, MA 01890
0.22
$2,149,300
4
2.5
2,973
Off Market
50 Lorena Rd, Winchester, MA 01890
0.19
$3,415,100
5
4.5
7,242
Off Market

Local Information

  • Map ViewExplore the area around 58 Jefferson Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1984
0.44 acre lot
2,910 sqft
$636/sqft
2 Car Garage

About this House

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.
58 Jefferson Rd, Winchester, MA 01890 is a 4 bedroom, 3 bathroom, 2,910 sqft single-family home built in 1984. It last sold for $1,850,000 on Apr 23, 2026 (3% above the $1,799,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,063,800, with a rent estimate of $6,816/month.
Last check for updates: about 13 hours ago
Listed by Stephanie Macfarland, (617) 710-2334
Wilson Wolfe Real Estate, (978) 658-2345
Bought with: The Collective, (617) 807-0853, Compass, (617) 206-3333
Source: MLS PIN, MLS#73488901

Home Details for 58 Jefferson Rd

Interior Features

Interior Details
Basement: Full,Interior Entry,Garage Access,Concrete,UnfinishedNumber of Rooms: 9Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Master Bathroom, Bathroom 1, Bathroom 2, Bathroom 3, Dining Room, Family Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 2910 Square Feet
Appliances & Utilities
Utilities: for Electric Range, for Electric Oven, for Electric Dryer, Washer HookupAppliances: Water Heater, Range, Dishwasher, RefrigeratorDishwasherLaundry: Main Level,Electric Dryer Hookup,Washer Hookup,First FloorRefrigerator
Heating & Cooling
Heating: Forced Air,OilHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Family RoomHas a FireplaceNo Spa
Gas & Electric
Electric: 200+ Amp Service
Windows, Doors, Floors & Walls
Window: Skylight(s), Insulated WindowsDoor: Insulated DoorsFlooring: Tile, Carpet, Hardwood, Stone / Slate, Flooring - Wall to Wall Carpet, Flooring - Stone/Ceramic Tile
Levels, Entrance, & Accessibility
Floors: Tile, Carpet, Hardwood, Stone Slate, Flooring Wall To Wall Carpet, Flooring Stone Ceramic Tile
Security
Security: Security System

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Deck - WoodExterior: Deck - Wood, Sprinkler SystemFoundation: Concrete PerimeterSprinkler System
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Open Parking Spaces: 4No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 6Parking: Attached,Under,Garage Door Opener,Storage,Paved Drive,Off Street,Paved
Frontage
Road Frontage: PublicResponsible for Road Maintenance: Public Maintained RoadRoad Surface Type: PavedNot on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 2910

Property Information

Year Built
Year Built: 1984
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: FrameNot Attached PropertyDoes Not Include Home Warranty
Property Information
Parcel Number: M:006 B:0449 L:0, 896196

Price & Status

Price
List Price: $1,799,000Price Per Sqft: $636/sqft
Status Change & Dates
Off Market Date: Tue Apr 07 2026

Active Status

MLS Status: Sold

Location

Direction & Address
City: Winchester

Building

Building Area
Building Area: 2910 Square Feet

Community

Community Features: Public Transportation, Shopping, Park, Medical Facility, Highway Access, House of Worship, Public School, SidewalksNot Senior Community

HOA

No HOA

Lot Information

Lot Area: 0.44 acres

Offer

Contingencies: Pending P&SListing Terms: Contract

Energy

Energy Efficiency Features: Thermostat

Miscellaneous

BasementMls Number: 73488901Above Grade Unfinished Area: 2910

Additional Information

Public TransportationShoppingParkMedical FacilityHighway AccessHouse of WorshipPublic SchoolSidewalks

Price and Tax history

DateEventPrice
Apr 23, 2026
Source: MLS PIN #73488901
Sold
$1,850,000
Mar 25, 2026
Source: MLS PIN #73488901
Contingent
$1,799,000
Mar 19, 2026
Source: MLS PIN #73488901
Listed For Sale
$1,799,000

Market trends in Winchester

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
62
2MoM

Around this home

What Locals Say about Winchester

At least 93 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 88 % Say yards are well-kept

  • 87 % Say people would walk alone at night

  • 85 % Say parking is easy

  • 79 % Say there are sidewalks

  • 79 % Say car is needed

  • 77 % Say it's walkable to restaurants

  • 77 % Say kids play outside

  • 75 % Say streets are well-lit

  • 74 % Say there's holiday spirit

  • 67 % Say they plan to stay for at least 5 years

  • 67 % Say there's wildlife

  • 66 % Say neighbors are friendly

  • 65 % Say it's walkable to grocery stores

  • 64 % Say it's quiet

  • 54 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Diana P.
    "Winchester is the cutest town, perfect for families. There is Town Say, and Enka, and everything is very family oriented. We even have great pubs/restaurants as well as sub shops, Greek food, nail salons, anything you could want in a home town!"
    7
    Flag
  • Dominic
    "Phenomenal public school system beginning from Kindergarten and extremely welcoming to new residents transferring in."
    0
    Flag
  • Stacie
    "Very family oriented. Not a great neighborhood if you don’t have children. Great, easy commute into the city. Not enough good restaurants that aren’t overpriced though. "
    0
    Flag
  • Yjchoi7
    "Very safe neighborhood.there are often summer events on the common. Teenagers can take train into Boston area fairly easily as there are two stops within Winchester. Fells is a great place for summer walks. "
    2
    Flag
  • Luis B.
    "perfect for my family It is livable stores Closer to me Barbershop computer store Restaurants I will love to buy a house in this area "
    2
    Flag
  • Yjchoiyjchoi
    "It’s very quiet and safe generally. Yet it’s close to Boston and Cambridge city life within a few stops of the commuter from Winchester. "
    0
    Flag
  • Tara
    "I have lived in this neighborhood for 25 years. I love it. Everybody is friendly and kind. The crime is minimal and it’s very quiet. "
    2
    Flag
  • Katie41287
    "I’m not afraid to walk home at 11pm, the town is clean and has plenty of events around town, the people are friendly and it is near public transportation. "
    1
    Flag
  • Anna S.
    "Excellent school Easy commute to Boston Downtown Great parks and pond nearby"
    0
    Flag
  • tod g.
    "Lovely town with easy access to Boston and easy getaway to northern New England."
    0
    Flag
  • jfrancis6
    "Family community built around three streets that form a circle that only has traffic of residents. The area borders the Town of Winchester forest that is great for walks and snow shoeing in winter. All homes are large and attract families were children can safely play and bike in the neighborhood. Many homes have residents who grow up in the neighborhood as children and returned to raise their families. A short walk 4/10 of a mile to train station for those who work in Boston a trip that takes 12 minutes with only one stop. Schools in Winchester are among the best in Massachusetts, a primary attraction to the Town. The Town center is only one mile away and has an addition train station there as well. The Mystic lakes are just beyond the train station with a Town beach and boating opportunities. The Town also borders a 2500 acre forest known as the Fells consisting of the Town water supply and miles of hiking or mountain biking."
    0
    Flag
  • marta3467
    "Can see kids playing ball in street; people walking their dog and Horn Pond and several nice restaurants all within walking distance"
    1
    Flag

LGBTQ Local Legal Protections

The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
The MLS listing information displayed is deemed reliable, but is not guaranteed accurate by the MLS.

Frequently asked questions about 58 Jefferson Rd

  • What is 58 Jefferson Rd estimated to be worth?
    Trulia's estimated value for 58 Jefferson Rd in Winchester, MA is $2,063,800.
  • What is the price history for 58 Jefferson Rd?
    58 Jefferson Rd in Winchester, MA last sold for $1,850,000 in April 2026.
  • Is Winchester a buyer's or seller's market?
    Winchester is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Winchester?
    Residents describe Winchester, MA as dog-friendly, well-kept, and easy to park in. Most residents say you need a car. See recently sold homes in Winchester, MA.
  • Does 58 Jefferson Rd have air conditioning?
    Yes, 58 Jefferson Rd in Winchester, MA has air conditioning.
  • Does 58 Jefferson Rd have laundry facilities?
    Yes, 58 Jefferson Rd in Winchester, MA has laundry facilities.

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