The Great "W" Towns Analysis

The W Towns Throwdown

A comprehensive analysis of all 15 "W" towns in the Boston Metro area, from ultra-luxury Weston to working-class Woburn. Plotting pretentiousness, schools, commute, and value across the entire spectrum.

Towns Analyzed
15
W towns total
Price Range
$620K - $2.15M
median home prices
School Range
5.0 - 9.9
out of 10 rating
Pretentiousness
4 - 10
index range

The Great "W" Towns Comparison Chart

TownPretentiousness IndexSchool QualityAvg Lot SizeInterior Sq FtCommuter RailDistance to BostonDominant Vibe
πŸ’°
Weston
Tier 1: The Heavyweights
10/10
9.7/102 acres5,000 sq ftβœ—15 milesPrivate estates, #2 schools
πŸ’Ž
Wellesley
Tier 1: The Heavyweights
9/10
9.9/100.75 acres4,000 sq ftβœ“12 milesAcademic, walkable, premium
πŸ›οΈ
Winchester
Tier 1: The Heavyweights
8/10
9.2/100.375 acres3,000 sq ftβœ“8 milesVillage charm, North Station
🏘️
Wayland
Tier 2: The High Achievers
7/10
9/101.5 acres3,500 sq ftβœ—18 milesPastoral value + new center
πŸš†
Westwood
Tier 2: The High Achievers
7/10
9.2/100.52 acres3,200 sq ftβœ“16 milesCommuter hub (MBTAΓ—2 + Amtrak)
🏘️
Westford
Tier 2: The High Achievers
6/10
8.5/101 acres3,000 sq ftβœ—28 milesSTEM families, strong schools
🏒
Westborough
Tier 5: The Exurban Choice
6/10
8/100.5 acres2,800 sq ftβœ“30 milesTop schools, 495 corridor
🏑
Wakefield
Tier 4: The Solid Suburbs
5/10
7.5/100.2 acres2,200 sq ftβœ“10 milesNorth Shore value
🏭
Waltham
Tier 3: The Urban-Suburban Blend
4/10
7/100.2 acres2,000 sq ftβœ“10 milesUrban-suburban tech hub
🌊
Watertown
Tier 3: The Urban-Suburban Blend
4/10
8.2/100.15 acres1,800 sq ftβœ—6 milesStreetcar suburb, Arsenal Yards
πŸš€
Wilmington
Tier 4: The Solid Suburbs
4/10
6.5/100.3 acres2,400 sq ftβœ“15 milesRoute 128 corridor value
🏒
Woburn
Tier 4: The Solid Suburbs
4/10
6.5/100.2 acres2,100 sq ftβœ“9 milesPragmatic access, Route 128
πŸ–οΈ
Weymouth
Tier 4: The Solid Suburbs
4/10
5/100.2 acres2,000 sq ftβœ“12 milesSouth Shore, MBTA Red via Quincy
Tier 1: The Heavyweights
3 towns
Avg Price:$1.8M
Avg Schools:9.6/10
Avg Pretentiousness:9.0/10
Tier 2: The High Achievers
3 towns
Avg Price:$1.2M
Avg Schools:8.9/10
Avg Pretentiousness:6.7/10
Tier 5: The Exurban Choice
1 towns
Avg Price:$0.8M
Avg Schools:8.0/10
Avg Pretentiousness:6.0/10
Tier 4: The Solid Suburbs
4 towns
Avg Price:$0.7M
Avg Schools:6.4/10
Avg Pretentiousness:4.3/10
Tier 3: The Urban-Suburban Blend
2 towns
Avg Price:$0.8M
Avg Schools:7.6/10
Avg Pretentiousness:4.0/10
πŸ’°

Weston

"Where billionaires go to hide from millionaires"

Price:$2.1M
Schools:9.7/10
Commute:35 min
Pretentiousness:
10/10

Best For:

Ultra-luxury buyers
Privacy seekers
Land lovers

Famous For:

Top schools & horse farms

πŸ’Ž

Wellesley

"Where every house has a wine cellar and every kid has a tutor"

Price:$1.9M
Schools:9.9/10
Commute:35 min
Pretentiousness:
9/10

Best For:

Ultra-luxury buyers
Education excellence
Prestige seekers

Famous For:

Wellesley College & downtown

πŸ›οΈ

Winchester

"Suburban perfection where every house has a golden retriever"

Price:$1.3M
Schools:9.2/10
Commute:27 min
Pretentiousness:
8/10

Best For:

Families with children
School district seekers
Suburban lifestyle

Famous For:

Town center & lakefront

🏘️

Wayland

"MetroWest's family favoriteβ€”Lexington schools without the price tag"

Price:$1.4M
Schools:9/10
Commute:35 min
Pretentiousness:
7/10

Best For:

Education-obsessed families
Nature lovers
Suburban perfection seekers

Famous For:

Conservation land

πŸš†

Westwood

"Top-20 schools plus elite commuter rail at 30% off Winchester prices"

Price:$1.3M
Schools:9.2/10
Commute:27 min
Pretentiousness:
7/10

Best For:

Train commuters
Families prioritizing elite schools
Value-conscious luxury buyers

Famous For:

Route 128 access

🏘️

Westford

"STEM families' dreamβ€”top schools in the 495 tech corridor"

Price:$0.8M
Schools:8.5/10
Commute:35 min
Pretentiousness:
6/10

Best For:

STEM-focused families
Tech workers
Value seekers

Famous For:

STEM education & tech corridor

🏒

Westborough

"Tech corridor hub with top schools and highway access"

Price:$0.8M
Schools:8/10
Commute:40 min
Pretentiousness:
6/10

Best For:

Tech workers
Families prioritizing schools
Those who work in MetroWest

Famous For:

Tech corridor & Route 9

🏑

Wakefield

"North of Boston value with surprisingly good schools"

Price:$0.8M
Schools:7.5/10
Commute:25 min
Pretentiousness:
5/10

Best For:

Value seekers
Families wanting good schools
Those who like lakeside living

Famous For:

Lake Quannapowitt

🏭

Waltham

"Where the Industrial Revolution started and tech bros now rule"

Price:$0.8M
Schools:7/10
Commute:25 min
Pretentiousness:
4/10

Best For:

Tech workers
First-time buyers
Food enthusiasts

Famous For:

Moody Street dining

🌊

Watertown

"Armenian food paradise that's secretly convenient to everything"

Price:$0.8M
Schools:8.2/10
Commute:20 min
Pretentiousness:
4/10

Best For:

Food enthusiasts
Young professionals
Those who want urban access

Famous For:

Armenian community & Arsenal Yards

πŸš€

Wilmington

"Route 128 value with $190M+ infrastructure upgrade"

Price:$0.8M
Schools:6.5/10
Commute:30 min
Pretentiousness:
4/10

Best For:

Highway commuters
Value seekers
Families wanting space

Famous For:

Route 128 access & infrastructure

🏒

Woburn

"Working-class north with I-93 access and honest prices"

Price:$0.7M
Schools:6.5/10
Commute:25 min
Pretentiousness:
4/10

Best For:

First-time buyers
Highway commuters
Value seekers

Famous For:

Route 128 corridor & corporate parks

πŸ–οΈ

Weymouth

"Most affordable South Shore access to Boston Harbor beaches"

Price:$0.6M
Schools:5/10
Commute:30 min
Pretentiousness:
4/10

Best For:

Beach lovers
First-time buyers
Commuter rail users

Famous For:

South Shore beaches

W-Town Throwdown

The ultimate bracket battle! 20 W-towns compete in head-to-head matchups. Vote for your favorites and see which town reigns supreme in the ultimate Massachusetts suburban showdown.

Town Vibes Voting

Cast your vote on the personality and character of each W town. Help build the community consensus on what makes each town unique and discover the most beloved characteristics.

Ready to dive deeper into the W towns?

Each town has its own unique character, advantages, and trade-offs. Explore individual profiles to find your perfect match.

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