Homes for Sale in Winchester

Exclusive suburb with top schools, Mystic Lakes, and refined residential streets.

Winchester is an exclusive residential suburb north of Boston with highly ranked schools, Mystic Lakes, and a mix of single-family homes. The housing market includes established properties on quieter streets. Buyers are drawn to the combination of school reputation, water access, and a refined community character.

School and lake proximity are significant premiums. Commuter rail provides transit access. Outdoor space and larger homes are common. The town’s school system is a major factor for family buyers seeking a suburban setting.

$660,000

Condo

2 bd · 1.1 ba · 1,190 sqft · Active

60 Lake St #E, Winchester

$1,110,000

Multi Family

2,186 sqft · Active

63-65 Harvard Street, Winchester

$1,999,000

Single Family

5 bd · 3.1 ba · 4,063 sqft · Active

21 Amberwood Dr, Winchester

$850,000

Single Family

3 bd · 1 ba · 1,313 sqft · Active

39 Henry Street, Winchester

$890,000

Single FamilyFixer

2 bd · 1 ba · 1,489 sqft · Active

80 Nelson St, Winchester

$2,650,000

Single Family

4 bd · 4.1 ba · 5,233 sqft · Active

18 Middlesex St, Winchester

$399,000

Condo

1 bd · 1 ba · 613 sqft · Active

200 Swanton St #727, Winchester

$700,000

Condo

2 bd · 2 ba · 1,240 sqft · Active

666 Main Street #217, Winchester

$329,900

CondoFixer

2 bd · 1 ba · 1,084 sqft · Active

20 Arthur St #20, Winchester

$1,299,000

Multi Family

2,946 sqft · Active

419-421 Washington St, Winchester

$2,195,000

Single Family

5 bd · 3.1 ba · 5,006 sqft · Active

276 High Street, Winchester

$2,750,000

Single Family

6 bd · 5.2 ba · 6,968 sqft · Active

14 Nassau Drive, Winchester

Price	Beds	Baths	Sq Ft	Address	Status
$660,000	2	1.1	1,190	60 Lake St #E, Winchester	Active
$1,110,000			2,186	63-65 Harvard Street, Winchester	Active
$1,999,000	5	3.1	4,063	21 Amberwood Dr, Winchester	Active
$850,000	3	1	1,313	39 Henry Street, Winchester	Active
$890,000	2	1	1,489	80 Nelson St, Winchester	Active
$2,650,000	4	4.1	5,233	18 Middlesex St, Winchester	Active
$399,000	1	1	613	200 Swanton St #727, Winchester	Active
$700,000	2	2	1,240	666 Main Street #217, Winchester	Active
$329,900	2	1	1,084	20 Arthur St #20, Winchester	Active
$1,299,000			2,946	419-421 Washington St, Winchester	Active
$2,195,000	5	3.1	5,006	276 High Street, Winchester	Active
$2,750,000	6	5.2	6,968	14 Nassau Drive, Winchester	Active

Overview

Winchester Profile	Snapshot
Primary Vibe	Exclusive and established suburb with highly ranked schools, Mystic Lakes, and a historic center. Popular with families seeking premium education and space.
Housing Prices	Prices are generally higher. Single-family homes near schools or the lakes command premiums. Outdoor space influences value.
Commute to Boston	Commuter rail provides access. Driving is common. Parking and outdoor space are readily available.
Schools	Served by Winchester Public Schools, which are highly regarded. Confirm assignments with the district.
Market	Strong demand supported by schools and location. Updated homes with views or outdoor space attract interest.
Housing Styles	Primarily single-family homes. Outdoor space and lake proximity are premiums.

Neighborhoods

Neighborhood / Area	Vibe / Character	Primary Property Type / Approx. Price	Market Note
Near Mystic Lakes	Scenic & Residential	Single-Family Homes Premiums for views.	Water access. Quieter setting.
Historic Center	Convenient & Established	Homes Higher price points.	Local amenities. Strong school appeal.
Residential Streets	Refined & Quiet	Homes Prices depend on condition.	More space. Settled character.