Get Natick and Metrowest Listings and Market Information

Work with Robb Enterprises real estate to buy, sell, or lease property that is right for you

  • Properties
    • For Rent
    • For Sale
    • Vacation Rental
    • Commercial
  • Specialty Properties
    • Natick New Construction
    • Natick Waterfront
    • Apartments for Rent in Natick MA 01760
    • Section 8 Advertised Properties
  • Agents
  • Compare
  • Blog
  • Contact Us

Properties

  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
  • 16 Glenwood Ave, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 18 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Glenwood Ave,73507137
Property Description

Must see! Beautifully renovated & expanded Cape offering flexibility for multigenerational living, complete w/ a legal unit over the garage ideal for in-laws, nanny, guests, or rental income. Thoughtfully designed w/ a seamless blend of private & communal spaces, the main home features an updated kitchen w/ mudroom, laundry & pantry, a spacious living room w/ gas fireplace, dining room, 1st flr bedrm & full bath, plus a flexible suite w/ kitchenette, sitting room & full bath. Upstairs offers 3 add’ bedrooms & a full bath. The finished lower level includes a family room, office, exercise space, bonus room w/ walkout, workshop, storage & cedar closet. Additional highlights include an oversized 2-car garage with EV charger, elevator lift, solar array, & direct access to the apartment featuring vaulted ceilings, gas fireplace, full kitchen, laundry & private deck. Set on an oversized level lot with mature landscaping, deck, patio & gazebo on a quiet cul-de-sac in the Lynch School district

Features
Heating System:
Natural Gas, Fireplace
Cooling System:
Central Air
Basement:
Full, Partially Finished, Walk-out Access
Fireplace:
Family Room
Parking:
Attached, Off Street, Paved, Paved Drive
Appliances:
Dishwasher, Refrigerator
Exterior Unit Features:
Professional Landscaping, Deck, Patio, Porch, Fenced Yard, Sprinkler System, Deck - Composite, Fruit Trees, Rain Gutters, Garden
Flooring:
Flooring - Hardwood, Flooring - Vinyl
Sewer:
Public Sewer
Style:
Cape
Water:
Public
Garage Parking:
2
Interior Features:
Home Office, Bathroom - Full, Countertops - Stone/granite/solid, Closet, Bathroom, Bonus Room, Walk-in Closet(s), Accessory Apt.
Lead Paint:
Unknown
Laundry Features:
First Floor
Additional Information
Grade School:
Lynch
High School:
Whs
Middle School:
Mccall
Market Time:
4
Parking Spaces:
9
Tax Year:
2025
Status:
Active
Price Per Sqft:
$319
Zoning:
RG
Orig Price:
$2,200,000
Fireplaces:
2
Waterfront:
No
MlsStatus:
Active
Address Map
City:
Winchester
State:
MA
County:
Middlesex
Postal Code:
01890
Longitude:
W72° 51' 14''
Latitude:
N42° 27' 47.4''
  • Google Map

Residential

16 Glenwood Ave, Winchester, Massachusetts

6 Bedrooms
4.5 Total Bathrooms
6,900 Sqft
$2,200,000
Listing ID #73507137
Basic Details
Property Type :
Residential
Listing Type :
For Sale
Price :
$2,200,000
Bedrooms :
6
Rooms :
18
Total Bathrooms :
4.5
Full Bathrooms :
4
Half Bathrooms :
1
Square Footage :
6,900 Sqft
Year Built :
1966
Lot Area :
0.44 Acre
Listing ID :
73507137
  • Share on Facebook
  • Share on Twitter
  • Share on Pinterest
  • PDF
  • Send to Friend
  • Request a Visit
Agent info
Robb Enterprises
  • Stephen E. Robb
  • View website
  • 617-212-0251
  • srobb@robbenterprises.com

Contact Agent

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.

Similar Properties

Residential

Residential

112 Highland Avenue, Winchester, Massachusetts

More
Residential

Residential

7 Sherman Place, Winchester, Massachusetts

More
Residential

Residential

7 Sherman Place, Winchester, Massachusetts

More
Residential

Residential

200 Swanton St, Winchester, Massachusetts

More
129 Washington St, Winchester, Massachusetts, 3 Bedrooms Bedrooms, 7 Rooms Rooms,3.5 BathroomsBathrooms,Residential,For Sale,Washington St,73513572

Residential

129 Washington St, Winchester, Massachusetts

More
8 Priscilla Ln, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 12 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Priscilla Ln,73513501

Residential

8 Priscilla Ln, Winchester, Massachusetts

More
38 Salem Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 9 Rooms Rooms,3.5 BathroomsBathrooms,Residential,For Sale,Salem Street,73513155

Residential

38 Salem Street, Winchester, Massachusetts

More
38 Salem Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 9 Rooms Rooms,3.5 BathroomsBathrooms,Residential,For Sale,Salem Street,73513154

Residential

38 Salem Street, Winchester, Massachusetts

More
Realtyna

Copyright © 2026