$2,099,000
16 & 16A Glenwood Ave
Winchester, MA, 01890
Must see! sprawling 2-3 family beautifully renovated & expanded home 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!
Property Details
Price:
$2,099,000
MLS #:
73507137
Status:
Active
Beds:
6
Baths:
4.5
Type:
Single Family
Subtype:
Single Family Residence
Listed Date:
Apr 24, 2026
Finished Sq Ft:
6,900
Total Sq Ft:
6,900
Lot Size:
19,217 sqft / 0.44 acres (approx)
Year Built:
1966
Schools
Elementary School:
Lynch
Middle School:
Mccall
High School:
Whs
Interior
Above Grade Finished Area
4796
Appliances
Dishwasher, Refrigerator
Bathrooms
4 Full Bathrooms, 1 Half Bathroom
Below Grade Finished Area
2104
Cooling
Central Air
Fireplaces Total
2
Flooring
Flooring – Hardwood, Flooring – Vinyl
Heating
Natural Gas, Fireplace
Interior Features
Bathroom – Full, Walk-In Closet(s), Closet, Countertops – Stone/Granite/Solid, Bathroom, Accessory Apt., Bonus Room, Home Office
Laundry Features
First Floor
Exterior
Accessibility Features
Accessible Entrance
Architectural Style
Cape
Attached Garage YN
1
Community Features
Public Transportation, Walk/Jog Trails, Bike Path, Public School
Covered Spaces
2
Exterior Features
Porch, Deck, Deck – Composite, Patio, Rain Gutters, Professional Landscaping, Sprinkler System, Fenced Yard, Fruit Trees, Garden
Fencing
Fenced/Enclosed, Fenced
Garage Spaces
2
Lot Features
Level
Open Parking Spaces
7
Open Parking YN
1
Parking Features
Attached, Paved Drive, Off Street, Paved
Parking Spots
9
Parking Total
9
Patio And Porch Features
Deck – Exterior, Porch, Deck, Deck – Composite, Patio
Roof
Shingle
Financial
Tax Year
2025
Taxes
$25,122
Marie Andrews is an award-winning, licensed real estate broker with licenses in Massachusetts and Florida. She has been selling real estate in the greater Boston area for over 20 years. Over the past two decades, Marie has worked for Century 21 Advanced Realty, building a reputation as a multi-million dollar producer. She has developed an extensive network of investors, lenders, and attorneys. Marie has a wide knowledge base on property management, Massachusetts real estate law, and building…
More About MarieMortgage Calculator
Map
Current real estate data for Single Family in Winchester as of Jun 10, 2026
71
Single Family Listed
56
Avg DOM
544
Avg $ / SqFt
$2,214,096
Avg List Price
Community
- Address16 & 16A Glenwood Ave Winchester MA
- CityWinchester
- CountyMiddlesex
- Zip Code01890
Subdivisions in Winchester
- Brooks / Parkhurst / Town Forest
- Cox Road / High St Extension neighborhood
- Flats
- Flats neighborhood
- Lakeview/Wedgemere~ Near downtown & Wedgemere train station
- Macdonald field neighborhood
- Middlesex / downtown
- Near town/ Pine St neighborhood
- Old Village/ West Side
- Rangeley Historical Estate
- The Flats
- Vinson-Owen School District.
- West Side
- Winning Farm
Similar Listings Nearby
Property Summary
- 16 & 16A Glenwood Ave Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $2,099,000 and features 6 beds, 5 baths, and has approximately 6,900 square feet of living space, and was originally constructed in 1966. The current price per square foot is $304. The average price per square foot for Single Family listings in Winchester is $544. The average listing price for Single Family in Winchester is $2,214,096. To schedule a showing of MLS#73507137 at 16 & 16A Glenwood Ave in Winchester, MA, contact your Pegasus Realty LLC agent at 781-858-3505.
Courtesy of Compass. 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.
16 & 16A Glenwood Ave
Winchester, MA