Single Family Residence at 59 Oakland St, Medford MA 02155, Medford
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 2 of 41
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 3 of 41
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 4 of 41
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 5 of 41
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 6 of 41
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 7 of 41
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 8 of 41
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 9 of 41
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 10 of 41
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 11 of 41
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 12 of 41
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 13 of 41
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 14 of 41
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 15 of 41
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 16 of 41
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 17 of 41
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 18 of 41
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 19 of 41
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 20 of 41
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 21 of 41
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 22 of 41
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 23 of 41
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 24 of 41
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 25 of 41
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 26 of 41
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 27 of 41
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 28 of 41
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 29 of 41
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 30 of 41
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 31 of 41
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 32 of 41
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 33 of 41
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 34 of 41
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 35 of 41
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 36 of 41
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 37 of 41
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 38 of 41
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 39 of 41
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 40 of 41
Single Family Residence at 59 Oakland St, Medford MA 02155, Medford, photo 41 of 41
41 photos

$964,999

59 Oakland St, Medford MA 02155
Medford, MA 02155
Listed by Christopher Jean
Bedrooms
4
Bathrooms
2
Living area
2,240 sqft
Year built
1900

About this home

Welcome to 59 Oakland Street, a beautifully maintained and thoughtfully updated 4-bedroom, 1-bathroom home offering 2,240 square feet in a highly sought-after Medford location. Situated near downtown Medford, the property offers easy access to shopping, restaurants, parks, public transportation, major highways including I-93 and Route 2, and Boston. Designed with both comfort and the future in mind, this home has been equipped with thoughtfully selected upgrades and systems intended to provide long term functionality and peace of mind. Features include a state of the art HVAC system with built-in humidifier and air filtration, a whole house water filtration system, and a backup generator. Smart home functionality allows many of the property’s systems and features to be conveniently controlled and monitored from a smartphone or mobile device, creating a modern, connected home designed for comfort, efficiency, and convenience. The generous layout provides ample space for everyday living, entertaining, and working from home. A walk-up attic offers exciting potential for additional living space and could be transformed into an oversized bedroom, home office, recreation room, or other flexible-use space. The private, spacious backyard provides an inviting outdoor retreat with plenty of room to entertain, relax, or enjoy time with family and friends. Combining substantial living space, thoughtful improvements, future expansion potential, and a prime Medford location, 59 Oakland Street offers a rare opportunity to own a home designed with both today and tomorrow in mind. Don’t miss the opportunity to see everything this special property has to offer. Property is being offered and sold in its present “AS-IS” condition. Solar panels are installed on the property but are currently disconnected. The existing solar agreement must be transferred to and assumed by the new Buyer at closing. Buyer and Buyer’s Agent should conduct their own due diligence regarding the solar system and the terms and obligations of the existing agreement. Surround sound equipment, security cameras, and Wi-Fi networking equipment will remain with the property. First Open House: Saturday, October 3rd from 11:00 AM to 12:30 PM.

Highlights

Fireplace

Property details

MLS #
73584421
Property type
Single Family Residence
Subdivision
Downtown Medford
Status
Active
Days on market
1
On market date
September 30, 2026
Stories
N/A
Total bathrooms
2
Garage spaces
N/A
Parking spaces
2
Lot size
0.14 acres
Loading map…

Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card (e.g. NC Dept. of Public Instruction, SC Report Card).

Elementary
Milton Fuller Roberts
0.3 mi away · Grades -1-5
Nearest school -- attendance-zone data not available here
4.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
517
Student:teacher ratio
12.6:1
District
Medford
Middle
Madeleine Dugger Andrews
0.71 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
458
Student:teacher ratio
10.7:1
District
Medford
High
Medford High
1.21 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
1,207
Student:teacher ratio
9.7:1
District
Medford

Walkability

Blended score for Medford's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

93
Highly walkable
out of 100
EPA National Walkability Index
17.5 / 20 -- Most walkable
Google Places amenity density
100 / 100
Restaurants & cafes20
Grocery stores9
Parks20
Schools19
Transit stops20
Pharmacies6

Market position

How this listing compares to current activity in Medford, from live MLS data.

On the market 1 days -- 76 fewer days than Medford's current average of 77 days.
For reference, the median list price across 562 active listings in Medford right now is $369,450.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

$
%
%
Adjust tax / insurance estimates
% / yr
$
/mo
Est. monthly payment
$5,961/mo
$193,000 down
$771,999 loan
Principal & interest$5,007
Property tax (est.)$804
Home insurance (est.)$150

Similar homes you might like

Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated 20 hr ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.