Expansive living and unparalleled curb appeal define this exceptional five-bedroom garrison colonial, ideally positioned near the natural beauty and extensive trails of the Fells Reservation. Set in the highly regarded Muraco Elementary School district, this spacious home offers an inviting blend of timeless architecture, thoughtful updates, and remarkable flexibility for today’s lifestyle. The sun-filled first floor features an open, seamless flow designed for both everyday living and effortless entertaining. A thoughtfully appointed eat-in kitchen with premium Sub-Zero and Fisher & Paykel appliances opens to the dining space, creating an ideal setting for gathering. A wood-burning fireplace anchors the living room where you can watch the world go by from the gorgeous picture window. A home office, mudroom, and powder room add functionality to this level. Upstairs, the generous primary suite includes a full bath and convenient laundry, with tree-top views from the Juliet balcony, complemented by four additional bedrooms and a family bath. A finished walk-up attic provides valuable storage and flexible bonus space, while the finished lower level adds a generous family room and several bonus spaces ideal for a second home office, playroom, media space, or additional recreation area, with kitchenette and full bath allowing for ADU possibilities. Outside, enjoy a truly private retreat with a fully fenced yard and pristine in-ground pool, offering exceptional space for outdoor living, entertaining, and relaxation. A two-car attached garage adds everyday convenience. With generous proportions throughout, multiple flexible spaces, an inviting open floor plan, and close proximity to the Fells Reservation, this Winchester Highlands property offers a rare opportunity to enjoy space, privacy, and sophisticated everyday living in one of Winchester’s desirable neighborhoods.
Listed by Dara Singleton · Better Homes and Gardens Real Estate - The Shanahan Group MLS PIN #73573887 · Updated 10/5/2026, 11:50:00 AM ET
Facts & features
Home overview
Property subtype
Single Family Residence
Property category
Residential
MLS status
Active
Bedrooms
5
Full bathrooms
3
Half bathrooms
1
Total bathrooms
3.5
Total rooms
12
Living area
3,722 sqft
Living area source
Measured
Above grade finished area
2,867 sqft
Below grade finished area
855 sqft
Building area
3,722
Building area units
Square Feet
Building area source
Measured
Area includes basement
Yes
Area disclosures
Unfinished room in basement and storage area in attic not included in total square footage
Interior & systems
Heating
Baseboard · Natural Gas
Heating available
Yes
Heating zones
2
Cooling
Central Air
Cooling available
Yes
Cooling zones
1
Appliances
Gas Water Heater · Water Heater · Range · Dishwasher · Trash Compactor · Microwave · Refrigerator · Washer · Dryer
Closet/Cabinets - Custom Built · Flooring - Hardwood · Open Floorplan · Lighting - Overhead
Family room
Level
Basement
Features
Flooring - Vinyl · Lighting - Overhead
Kitchen
Level
First
Features
Skylight · Flooring - Hardwood · Dining Area · Pantry · Countertops - Stone/Granite/Solid · Kitchen Island · Exterior Access · Open Floorplan · Recessed Lighting · Stainless Steel Appliances · Gas Stove · Lighting - Pendant
Office
Level
First
Features
Closet/Cabinets - Custom Built · Flooring - Hardwood
Bathroom 1
Level
First
Features
Bathroom - Half
Bathroom 2
Level
Second
Features
Bathroom - Full · Bathroom - Tiled With Shower Stall
Bathroom 3
Level
Second
Features
Bathroom - Full · Bathroom - Tiled With Tub & Shower
Construction & condition
Year built
1953
Year built source
Public Records
Year built details
Actual
Architectural style
Colonial · Garrison
Construction materials
Frame
Foundation
Block
Roof
Shingle
Attached property
No
Home warranty
No
Insulation
Fiberglass
Exterior color
Blue
Accessory dwelling unit
N
Garage & parking
Total parking spaces
5
Parking features
Attached · Garage Door Opener · Heated Garage · Garage Faces Side · Paved Drive · Paved
Garage
Yes
Garage spaces
2
Attached garage
Yes
Covered spaces
2
Carport
No
Open parking
Yes
Open parking spaces
3
Lot & outdoor features
Lot area
7,571 sqft (about 0.17 acres)
Lot size
0.17 acres
Reported lot area
0.17
Lot size units
Acres
Lot features
Corner Lot
Exterior features
Patio · Pool - Inground · Rain Gutters · Storage · Professional Landscaping · Sprinkler System · Fenced Yard · Outdoor Shower
Patio & porch
Patio
Fencing
Fenced/Enclosed · Fenced
Private pool
Yes
Pool features
In Ground
Spa
No
Waterfront
No
Beachfront
No
Utilities & infrastructure
Water source
Public
Sewer
Public Sewer
Road frontage
Public
HOA & community
Homeowners association
No
Community features
Park · Walk/Jog Trails · Medical Facility · Conservation Area · Highway Access · Public School
Senior community
No
Taxes & property records
Annual property tax
$15,088
Tax year
2026
Assessed value
$1,361,800
Parcel number
894959
Zoning
RDB
Registry book
62315
Registry page
545
Location & listed schools
City
Winchester
County
Middlesex
State
MA
ZIP code
01890
Listed elementary school
Muraco
Listed middle school
Mccall
Listed high school
Whs
Directions
Highland Ave. on the corner of Stone Ave.
Listing & disclosures
MLS number
73573887
Listing date
2026-09-09
Original entry date
2026-09-09
Status changed
2026-09-09
Listing modified
2026-10-05
Original list price
$1,650,000
Current list price
$1,650,000
List price per sqft
$443.31
Days on market
26
Property market time
26
Disclosures
Third floor finished room is not heated but is air conditioned. Please see list of Owner Updates attached to MLS. Floor plans for marketing purposes only. Some photos virtually enhanced.
Disclosure indicator
N
Lead paint
Unknown
Price & tax details
Current asking price$1,650,000
Original asking price$1,650,000
Listed on2026-09-09
Days on market26
Tax record supplied by MLS
Year
Property tax
Assessed value
2026
$15,088
$1,361,800
These records are supplied by the current listing. Assessed value is not market value; confirm taxes with the local assessor.
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SCHOOLS & EDUCATION
Schools & performance
2026 MA DESE
School names, grades and state-reported measures are listed below.
School name supplied by the listing; confirm with the district.
MLS school names do not guarantee attendance. Assignment can vary by school year, grade and admissions policy; confirm with the district before committing.What do these numbers mean?
DESE accountability percentiles (1–99) compare schools administering similar assessments, using up to two years of indicators. These are not test scores out of 100 or GreatSchools 1–10 ratings. Progress toward targets is a separate state measure. Consider programs, support services and your child’s needs as well.
School names link to available school or district websites.