Active
4 Days on market
37 Mayflower Road Winchester — Photo 1 of 42

37 Mayflower Road Winchester — Photo 1 of 42

$3,149,000

Investment Analysis — 37 Mayflower Road

Winchester, MA 01890

Based on HUD Small Area Fair Market Rent for Boston-Cambridge-Quincy, MA-NH HUD Metro FMR Area, a 7-bedroom in 01890 carries an estimated $4,120/mo in gross rent — about a 0.25% cap rate and $7,740/yr in estimated NOI at the $3,149,000 list price. Adjust every assumption in the calculator below.

View Standard Listing

Beds

7

Baths

7.5

SqFt

8,540

Style

Single Family

Built

2009

Magnificent newer sun-filled Colonial ideally situated in a premier West Side cul-de-sac, offering over 8,000 sq ft of beautifully finished living space across four levels-A great price at only $368psf! !Designed for grand-scale entertaining and multi-generational living, this exceptional home features 7 bedrooms, 7.5 baths, four fireplaces and a 3-car direct-entry garage, all complemented by custom built-ins, fine cabinetry and beautiful millwork throughout. The newly renovated chef’s kitchen showcases quartz countertops, an oversized center island, two dishwashers and a butler’s pantry with wine fridge and ice maker, flowing seamlessly into the elegant dining room, living room and fireplaced family room overlooking the meticulously maintained grounds. A dedicated first-floor wing offers incredible flexibility for extended family, au pair or guests, while a private office with custom wet bar and additional spaces can easily accommodate two executive home offices. Upstairs, the grand primary suite is joined by four additional bedroom suites, each offering a private bath, sitting area and generous closet space. The third floor provides a completely private guest or teen suite with a full bath and two closets.The finished lower-level offers media, game and gym areas with a full bath and direct access to the inviting heated pool and lush landscaped grounds. Unmatched in scale and versatility with resort-like amenities, exceptional craftsmanship and a coveted West Side location, this remarkable home offers luxury living at its finest.

ADU Potential

Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 8,540 sq ft principal dwelling). Lot size: 20,051 sq ft.

Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.

Estimates — not financial advice

These figures are illustrative estimates for informational purposes only — not an appraisal, valuation, or guarantee of rent, income, or returns, and not financial, tax, or investment advice. Rent is either the figure reported on the MLS listing — in-place rent that may differ from market and is not verified against the actual leases — or, where the listing reports none, an estimate from HUD Small Area Fair Market Rents, a government benchmark that may differ from actual market rent. Each figure is labelled with its source. Cap rate, NOI, and returns depend on the assumptions shown, which you can change. MLS and other third-party data may be inaccurate or out of date. Verify all figures independently and consult your own financial, tax, and legal advisors before making any investment decision.

Open Houses

Property Details

Financials

Original Price$3,149,000
Annual Taxes$29,834

Parking

Garage3
Off-Street12

Interior Specifications

Total Rooms13
Fireplaces4
FlooringTile, Hardwood, Flooring - Hardwood, Flooring - Stone/Ceramic Tile
BasementFull, Finished, Walk-Out Access, Interior Entry

Climate & Utilities

HeatingForced Air, Natural Gas, Fireplace(s), Fireplace
CoolingCentral Air
WaterPublic
SewerPublic Sewer

Building & Exterior

ConstructionFrame
RoofShingle
FoundationConcrete Perimeter
ZoningRDA

Property & Lot

Acres0.46
SqFt Lot20,051
Lot FeaturesCul-De-Sac

Amenities & Appliances

Gas Water Heater • Oven • Dishwasher • Disposal • Microwave • Range • Refrigerator • Freezer • Washer • Dryer • Wine Refrigerator

Neighborhood

Shopping • Pool • Tennis Court(s) • Park • Walk/Jog Trails • Golf

Geography

Floorplan Breakdown

Structural Layout

Second
Master BedroomBedroom 2Bedroom 3Bedroom 4Bedroom 5Bathroom 2Bathroom 3
First
Living RoomDining RoomKitchenOfficeFamily RoomBathroom 1
Living Room
Lvl First

20 x 16

Flooring - Hardwood, Lighting - Sconce

Dining Room
Lvl First

20 x 15

Flooring - Hardwood, Lighting - Sconce, Lighting - Pendant

Kitchen
Lvl First

22 x 13

Flooring - Hardwood, Countertops - Upgraded, Kitchen Island, Breakfast Bar / Nook, Country Kitchen, Exterior Access, Recessed Lighting, Lighting - Pendant, Lighting - Overhead

Office
Lvl First

16 x 14

Fireplace, Flooring - Hardwood, Wet bar

Family Room
Lvl First

21 x 18

Ceiling Fan(s), Flooring - Hardwood, Recessed Lighting, Lighting - Sconce

Master Bedroom
Lvl Second

30 x 20

Bathroom - Full, Ceiling Fan(s), Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Hardwood, Double Vanity, Dressing Room, Recessed Lighting, Lighting - Sconce, Closet - Double

Bedroom 2
Lvl Second

17 x 16

Bedroom 3
Lvl Second

22 x 17

Bathroom - Full, Ceiling Fan(s), Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Hardwood, Flooring - Stone/Ceramic Tile

Bedroom 4
Lvl Second

18 x 17

Bathroom - Full, Ceiling Fan(s), Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Hardwood, Flooring - Stone/Ceramic Tile, Recessed Lighting

Bedroom 5
Lvl Second

15 x 15

Bathroom - Full, Ceiling Fan(s), Walk-In Closet(s), Flooring - Hardwood, Recessed Lighting

Bathroom 1
Lvl First

9 x 6

Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Stone/Ceramic Tile

Bathroom 2
Lvl Second

15 x 13

Bathroom - Full, Flooring - Stone/Ceramic Tile

Bathroom 3
Lvl Second

10 x 9

Bathroom - Full, Flooring - Stone/Ceramic Tile

Property History

Listed
$3,149,000

Sep 8, 2026

MLS® 73573670

Terminated
$3,179,000

Sep 3, 2026

MLS® 73502853

Listed
$3,179,000

Apr 16, 2026

MLS® 73502853

Terminated
$3,537,000

Apr 14, 2026

MLS® 73475646

Listed
$3,537,000

Feb 9, 2026

MLS® 73475646

Terminated
$1,899,999

May 2, 2011

MLS® 71012550

Listed
$1,899,999

Dec 23, 2009

MLS® 71012550

Listing Provided By

Listing Agent: Kim Covino & Co. Team

Listing Office: Compass

MLS® Number: 73573670