Active
7 beds8,540 sqft

37 Mayflower Rd, Winchester, MA 01890

Single FamilyProperty Type
0.46 acresLot Size
2009Year Built
$369/sq ftPrice per sq ft
12 carsParking Spaces

Description

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...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.
32 days on Market
Last updated: 09/12/2026 03:06 AM • Source: MLS PIN, MLS#: 73573670

Location

Listing Courtesy of: .

Add your commute
Payment Calculator

$19,297 per month

30 year fixed, 7.03% Interest

Principal and Interest

$16,811

Property Taxes

$2,486

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.
Know your buying power with a preapproval and custom rate in minutes
Rocket Mortgage1

Property Information for 37 Mayflower Road

Property Details

  • Taxes: $29,834 / year
  • MLS Type: Single Family / Detached
  • Town: Winchester
  • Area: MA-Winchester
  • Architectural Style: Colonial
  • Style: Garden, Colonial
  • Garage Spaces: 3
  • Open Parking Spaces: 9.00
  • Parking Spaces Total: 12

Building Information

  • Year Built: 2009
  • Lot Size: 0.46 AC / 20,051 SF

General Details

Property Details
  • Building Area Units: Square Feet
  • Community Features: Shopping, Swimming Pool, Tennis Court, Park, Walk/Jog Trails, Golf Course, Sidewalks
  • Living Area: 8540.0
  • Color: Beige
  • SqFt with Basement: Yes
  • Property Attached: No
  • Single Family Type: Detached
  • Waterfront: No
  • Water View: No
  • Year Built Details: Approximate,Renovated Since
  • Year Built Source: Public Records
Location/School
  • Grade School: Vinson Owen
  • High School: Winchester High
  • Middle School: Mccall Middle

Features

Interior Features
  • Appliances: Gas Water Heater, Oven, Dishwasher, Disposal, Microwave, Range, Refrigerator, Freezer, Washer, Dryer, Wine Refrigerator
  • Basement Features: Full, Finished, Walk Out, Interior Access
  • Num of Baths: 8.0
  • Num of Full Baths: 7
  • Num of Half Baths: 1
  • Bathrooms Total Decimal: 7.50
  • Bathrooms Total Integer: 8
  • FireplaceFeatures: Family Room, Living Room, Master Bedroom
  • FireplaceYN: Yes
  • Fireplaces: 4
  • Flooring: Tile, Hardwood, Flooring - Hardwood, Flooring - Stone/Ceramic Tile
  • Interior Features: Wet bar, Bathroom - Full, Walk-In Closet(s), Closet, Ceiling Fan(s), Lighting - Overhead, Recessed Lighting, Office, Bedroom, Foyer, Game Room, Exercise Room, Wired for Surround Sound
  • Interior Features: Wired for Surround Sound, Security System
  • Laundry Features: Flooring - Hardwood, Second Floor
  • Primary Bath: Yes
  • SpaYN: No
  • Window Features: Insulated Windows, Storm Window(s), Screens
Exterior Features
  • Construction: Frame
  • Exterior Features: Deck, Patio, Pool - Inground, Professional Landscaping, Sprinkler System, Decorative Lighting, Screens, Garden
  • Exterior Features: Pool - Inground, Screens, Professional Landscaping, Sprinkler System, Decorative Lighting, Garden Area, Deck, Patio
  • Fencing: Fenced/Enclosed
  • Lot Description: Cul-De-Sac
  • Patio And Porch Features: Deck, Patio
  • Pool Features: In Ground
  • Pool Private: Yes
  • Roof Material: Shingle
Parking Features
  • Attached Garage: Yes
  • Carport: No
  • Covered Spaces: 3.00
  • Garage: Yes
  • Garage Parking: Attached, Garage Door Opener, Oversized Parking, Paved Drive, Off-Street, Paved Driveway
  • Open Parking: Yes
  • Parking Features: Attached, Garage Door Opener, Oversized Parking, Paved Drive, Off-Street, Paved Driveway
  • Parking Features: Oversized Parking, Off-Street, Paved Driveway
Utilities
  • Cooling: Central Air
  • Cooling: Yes
  • Heating: Forced Air, Natural Gas, Fireplace(s), Fireplace
  • Heating: Yes
  • Sewer: City/Town Sewer
  • Utility Connections: for Gas Range
  • Water: Public

Room Information

Primary Bedroom
  • Room Primary Bedroom Area: 600.0
  • Room Primary Bedroom Features: 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
  • Room Primary Bedroom Length: 30.0
  • Primary Bedroom Level: Second Floor
  • Room Primary Bedroom Width: 20.0
Bedroom 2
  • Bedroom2 Area: 272.0
  • Bedroom2 Features: Bathroom - Full,Ceiling Fan(s),Walk-In Closet(s),Closet/Cabinets - Custom Built,Flooring - Hardwood,Flooring - Stone/Ceramic Tile
  • Bedroom2 Length: 17.0
  • Bedroom2 Level: Second
  • Bedroom2 Width: 16.0
Bedroom 3
  • Bedroom3 Area: 374.0
  • Bedroom3 Features: Bathroom - Full,Ceiling Fan(s),Walk-In Closet(s),Closet/Cabinets - Custom Built,Flooring - Hardwood,Flooring - Stone/Ceramic Tile
  • Bedroom3 Length: 22.0
  • Bedroom3 Level: Second
  • Bedroom3 Width: 17.0
Bedroom 4
  • Bedroom4 Area: 306.0
  • Bedroom4 Features: Bathroom - Full,Ceiling Fan(s),Walk-In Closet(s),Closet/Cabinets - Custom Built,Flooring - Hardwood,Flooring - Stone/Ceramic Tile,Recessed Lighting
  • Bedroom4 Length: 18.0
  • Bedroom4 Level: Second
  • Bedroom4 Width: 17.0
Bedroom 5
  • Bedroom5 Area: 225.0
  • Bedroom5 Features: Bathroom - Full,Ceiling Fan(s),Walk-In Closet(s),Flooring - Hardwood,Recessed Lighting
  • Bedroom5 Length: 15.0
  • Bedroom5 Level: Second
  • Bedroom5 Width: 15.0
Bathroom 1
  • Bathroom1 Area: 54.0
  • Bathroom1 Features: Walk-In Closet(s),Closet/Cabinets - Custom Built,Flooring - Stone/Ceramic Tile
  • Bathroom1 Length: 9.0
  • Bathroom1 Level: First
  • Bathroom1 Width: 6.0
Bathroom 2
  • Bathroom2 Area: 195.0
  • Bathroom2 Features: Bathroom - Full,Flooring - Stone/Ceramic Tile
  • Bathroom2 Length: 15.0
  • Bathroom2 Level: Second
  • Bathroom2 Width: 13.0
Bathroom 3
  • Bathroom3 Area: 90.0
  • Bathroom3 Features: Bathroom - Full,Flooring - Stone/Ceramic Tile
  • Bathroom3 Length: 10.0
  • Bathroom3 Level: Second
  • Bathroom3 Width: 9.0
Dining Room
  • Dining Room Area: 300.0
  • Dining Room Features: Flooring - Hardwood,Lighting - Sconce,Lighting - Pendant
  • Dining Room Length: 20.0
  • Dining Room Level: First
  • Dining Room Width: 15.0
Family Room
  • Family Room Area: 378.0
  • Family Room Features: Ceiling Fan(s),Flooring - Hardwood,Recessed Lighting,Lighting - Sconce
  • Family Room Length: 21.0
  • Family Room Level: First
  • Family Room Width: 18.0
Kitchen
  • Kitchen Area: 286.0
  • Kitchen Features: Flooring - Hardwood,Countertops - Upgraded,Kitchen Island,Breakfast Bar / Nook,Country Kitchen,Exterior Access,Recessed Lighting,Lighting - Pendant,Lighting - Overhead
  • Kitchen Length: 22.0
  • Kitchen Level: First
  • Kitchen Width: 13.0
Laundry
  • Laundry Dimen: 17X8
Living Room
  • Room Living Room Area: 320.0
  • Room Living Room Features: Flooring - Hardwood,Lighting - Sconce
  • Room Living Room Length: 20.0
  • Room Living Room Level: First
  • Room Living Room Width: 16.0
Other Room 1
  • Room Office Area: 224.0
  • Room Office Features: Fireplace,Flooring - Hardwood,Wet bar
  • Room Office Length: 16.0
  • Room Office Level: First
  • Room Office Width: 14.0

Property Information

Property Info
  • Year Round: Yes
  • Farm Land Area Units: Square Feet
  • WARRANTY: No
  • Lot Size Units: Acres
  • Road Frontage Type: Public, Dead End
  • Road Responsibility: Public Maintained Road
  • Road Surface Type: Paved
  • Disclosures: **1st FL IN LAW suite w fplc or Primary BR option** Pool is situated on side yard,w/plenty of additional yard space. Home has 3 dishwashers,3 disposals. Full pantry w wine cooler,ice maker & dry pantry for extra storage/ Office w/ full wet bar /easy access pool bar area *some virtual staging*
Tax Information
  • Tax ID: M:023 B:0060 L:0,900602
  • Assessments: $2,690,200
  • Book: 57602
  • Tax Year: 2025
  • Zoning: RDA

Building / Association Information

Living Characteristics
  • Beds Total: 7
Other Building Characteristics
  • Foundation: Concrete Perimeter
  • Cooling Zones: 6
  • Heat Zones: 6
Complex & Association Information
  • Association Security: Security System
  • Adult Community: No

Property History for 37 Mayflower Road

DateEvent & SourcePriceAppreciation
Sep 8, 2026

Listed (Active)

MLS PIN #73573670

$3,149,000—
Sep 3, 2026

Canceled

MLS PIN #73502853

$3,179,000—
Apr 16, 2026

Listed (Active)

MLS PIN #73502853

$3,379,000—
DateEvent & SourcePrice
09/08/2026

Listed (Active)

MLS PIN #73573670

$3,149,000
09/03/2026

Canceled

MLS PIN #73502853

$3,179,000
04/16/2026

Listed (Active)

MLS PIN #73502853

$3,379,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public records

37 Mayflower Road

Beds

7

Baths

7.5

Total Finished SqFt

7,209 SqFt

Above Grade Finished SqFt

7,209 SqFt

Unfinished Basement SqFt

1,442 SqFt

Stories

2

Schools near 37 Mayflower Road

This home is within Winchester School District.
Rating
School
Type
Grades
Distance
Public - PK to 5
Public - 6 to 8
Public - 9 to 12
Rating
School
Distance
Vinson-Owen Elementary School
PublicPK to 5

McCall Middle School
Public6 to 8

Winchester High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Similar Homes

New listings in 01890

$1,299,000 | 39 Forest Street, Winchester, MA 01890
1/38
Open: 10/10 12:00PM - 02:00PMNew

$1,299,000

3
Bedrooms
2,350
Square Feet
0.26
Acres
$1,399,000 | 15 Lloyd Street, Winchester, MA 01890
1/40
Listed By CompassOpen: 10/10 01:00PM - 02:30PM

$1,399,000

5
Bedrooms
2,071
Square Feet
0.11
Acres
$2,199,000 | 42 Everett Avenue, Winchester, MA 01890
1/40
Open: 10/10 01:00PM - 02:30PM

$2,199,000

6
Bedrooms
4,947
Square Feet
0.41
Acres
$2,049,000 | 21 Amberwood Drive, Winchester, MA 01890
1/42
Listed By CompassOpen: 10/10 11:00AM - 01:00PM

$2,049,000

5
Bedrooms
4,063
Square Feet
0.46
Acres
$329,900 | 20 Arthur Street, Unit 20, Winchester, MA 01890

$329,900

2
Bedrooms
1,084
Square Feet
$2,399,000 | 63 Wedgemere Avenue, Winchester, MA 01890
1/39
Open: 10/10 11:00AM - 12:30PMVirtual Tour

$2,399,000

4
Bedrooms
3,550
Square Feet
0.43
Acres
$899,000 | 39 Henry Street, Winchester, MA 01890
1/23
Listed By Coldwell Banker RealtyOpen: 10/10 12:00PM - 01:30PM

$899,000

3
Bedrooms
1,313
Square Feet
0.36
Acres
a view of house with a yard
1/28
Open: 10/10 01:00PM - 02:30PM

$3,299,000

7
Bedrooms
7,226
Square Feet
0.43
Acres
$18,000,000 | 15 Vinson Circle, Winchester, MA 01890
1/42

$18,000,000

6
Bedrooms
10,000
Square Feet
0.98
Acres

37 Mayflower Road is a single family home for sale in Winchester, MA 01890. This property was listed for sale on September 8, 2026 by Compass, it's currently listed at $3,149,000. It has been on the market for a total of 32 days and was last sold on October 7, 2011. This listing's school district is Winchester School District. Nearby schools include Vinson-Owen Elementary School, McCall Middle School and Winchester High School. 37 Mayflower Road is a 7-bed, 8-bath, 8,540 sqft single family home built in 2009.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.

The property listing data and information, or the images, set forth herein were provided to MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS. The property listing data and information, and the images, 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., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the images, set forth herein.