Single Family Residence at 26 Mayflower Road, Winchester
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$1,950,000

Bedrooms
5
Bathrooms
4
Living area
3,371 sqft
Year built
1962
26 Mayflower Road
Winchester, MA 01890

Highlights

Property type
Single Family Residence
Lot size
0.38 acres
Garage
2 spaces
On market
35 days
  • Fireplace

About this home

Welcome to 26 Mayflower Road, located in one of Winchester’s sought-after neighborhoods alongside Winchester Country Club. From the beautifully landscaped grounds to the updated front door, garage doors, and recently redone front steps, this home offers wonderful curb appeal from the moment you arrive. Inside, the main level is warm, inviting, and filled with natural light, featuring a comfortable living room with wood-burning fireplace, an open kitchen and dining area, and a sun-filled family room that opens directly to a private brick patio. Whether you're enjoying your morning coffee, grilling, gathering with friends, or simply relaxing at the end of the day, the indoor-outdoor flow makes this home especially easy to enjoy. The spacious primary suite offers double closets and a beautiful bath with double vanity sinks, soaking tub, and tiled walk-in shower. An attached guest/in-law suite with its own private entrance, full bath, and kitchenette provides exceptional flexibility for guests, extended family, an au pair, or a private work-from-home space. The finished lower level adds even more room to spread out, with two additional living spaces and a full bathroom—perfect for a teen suite, home office, gym, playroom, or media space. Outside, beautiful landscaping, irrigation, and the expansive brick patio create a private setting for entertaining or simply enjoying the outdoors. Ideally located near commuter routes, the MBTA Commuter Rail, shopping, restaurants, schools, and downtown Winchester, this is a home that offers the space and flexibility to fit the way you live, all in a location that makes getting where you need to go easy.

Property details

MLS
MLS Property Information Network
MLS #
73584117
Property type
Single Family Residence
Subdivision
N/A
Status
Active
Days on market
35
On market date
September 29, 2026
Stories
N/A
Total bathrooms
4
Garage spaces
2
Parking spaces
6
Lot size
0.38 acres
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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.

Elementary
Ambrose Elementary
0.72 mi away · Grades 0-5
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
345
Student:teacher ratio
11.5:1
District
Winchester
Middle
Ottoson Middle
1.37 mi away · Grades 7-8
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
906
Student:teacher ratio
11.3:1
District
Arlington
High
Arlington High
1.59 mi away · Grades 9-12
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
1,483
Student:teacher ratio
13.0:1
District
Arlington

Walkability

Blended score for Winchester'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).

34
Car-dependent
out of 100
EPA National Walkability Index
4.8 / 20 -- Least walkable
Google Places amenity density
48 / 100
Restaurants & cafes1
Grocery stores1
Parks8
Schools7
Transit stops20
Pharmacies0

Market position

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

On the market 35 days -- 58 fewer days than Winchester's current average of 93 days.
For reference, the median list price across 176 active listings in Winchester right now is $824,500.

Mortgage calculator

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

Adjust tax / insurance estimates
Est. monthly payment
$11,893/mo
$390,000 down
$1,560,000 loan
Principal & interest$10,118
Property tax (est.)$1,625
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network. Last updated October 4, 2026.

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.