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Southlake vs. Westport: Which Offers the Better Family Lifestyle?

  • Writer: Nitin Gupta, CRS, REALTOR
    Nitin Gupta, CRS, REALTOR
  • Jun 22
  • 3 min read

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Luxury families moving from the East Coast often compare prestigious towns like Westport, CT, to upscale Dallas suburbs like Southlake, TX.Both offer top schools, high-end homes, and an affluent lifestyle—but key differences in climate, cost of living, and space make one a better fit for your family. Here’s how Southlake and Westport stack up in 2025 for luxury-minded families prioritizing schools, community, and long-term value.

If you’re considering relocating from Connecticut’s Gold Coast to North Texas, it’s natural to compare two of the country’s top-tier family-friendly luxury markets: Southlake, TX and Westport, CT. Each offers a strong school system, prestigious real estate, and a family-oriented community. But the lifestyle and value proposition couldn’t be more different.

Let’s break it down.


Overall Lifestyle & Family Feel

Southlake, TX

  • Master-planned neighborhoods with sidewalks, parks, and trails

  • Year-round outdoor living with sunny, mild winters

  • Gated and guarded communities with resort-style amenities

  • Country club culture, sports leagues, and local boutiques

  • Very low crime rate, strong sense of community

Westport, CT

  • Coastal charm and proximity to NYC

  • Four-season climate with heavy winters

  • Historic homes, colonial and shingle-style architecture

  • Exclusive private beach clubs, yacht clubs, and art centers

  • Higher density, less land per home, but walkable downtown


Home Value, Lot Size & Property Features

Feature

Southlake, TX

Westport, CT

Typical Luxury Home Price

$1.5M – $5M

$2.5M – $6M

Lot Size

0.5 – 1+ acres

0.2 – 0.5 acres

Home Style

Modern, transitional, Mediterranean

Colonial, farmhouse, traditional

Age of Homes

Mostly built post-2000

Many built pre-1980, with renovations

Outdoor Living

Pools, kitchens, covered patios standard

Limited due to cold climate


Schools & Education

Southlake

  • Served by Carroll ISD, one of Texas’ top-rated school districts

  • Academic excellence, sports dominance, and modern facilities

  • Nationally ranked public high school with a strong college prep focus

Westport

  • Westport Public Schools consistently rank among the best in Connecticut

  • Smaller school size and rigorous academics

  • Excellent arts programs and college prep pathways

Bottom Line: Both offer A+ education. Southlake’s public schools are a major draw for families seeking private-quality education without the tuition.


Climate & Weather

Southlake

  • 232 sunny days per year

  • Mild winters, ideal for year-round outdoor living

  • Hot summers balanced by home design (covered patios, pools)

Westport

  • Four true seasons, including cold, snowy winters

  • Limited outdoor enjoyment during late fall and winter

  • Homes require snow removal, heating oil, and seasonal maintenance


Cost of Living & Tax Advantages

Southlake (Texas)

  • 0% state income tax

  • Lower property tax per dollar spent on luxury real estate

  • Greater long-term wealth preservation

Westport (Connecticut)

  • High state income tax (up to 6.99%)

  • Higher utility, heating, and maintenance costs

  • Significant costs associated with aging homes and Northeast weather


Community, Safety, and Amenities

Southlake

  • Southlake Town Square offers high-end shopping, restaurants, and civic events

  • Exclusive clubs, golf courses, and sports leagues

  • Strong family culture, low crime, high community engagement

Westport

  • Known for elite arts scene, literary culture, and NYC commuter lifestyle

  • Westport Country Playhouse, upscale dining, and historic downtown

  • Excellent amenities but at a higher cost and more limited outdoor seasons


Relocation Considerations

East Coast luxury families relocating to Southlake often cite:

  • More house and land for the money

  • Top-rated schools without paying for private tuition

  • Climate that supports an active, outdoor-oriented lifestyle

  • Less stress over snow, ice, and cold weather maintenance

  • Better long-term tax benefits and wealth preservation


Work With a Trusted Relocation Expert

Moving from Westport or another East Coast market to Southlake?Nitin Gupta, CRS, GRI, ABR®, is a luxury relocation expert who understands the nuances between the Northeast and North Texas markets. He helps high-net-worth families make smart real estate decisions and find the best communities that match their lifestyle.


➡ Read reviews from other relocating families:https://www.nitinguptadfw.com/reviews

➡ Begin your Dallas luxury relocation with expert guidance:https://www.nitinguptadfw.com/contact




FIND A LUXURY HOME IN SOUTHLAKE, TEXAS WITH NITIN GUPTA, BROKER ASSOCIATE, REALTOR®.


When purchasing a luxury home in Southlake, Texas, it’s essential to consider factors such as location, architectural style, security, and amenities to ensure the home meets both lifestyle and investment needs. By selecting a property in a prestigious neighborhood with numerous amenities and security measures, buyers can ensure they’re making a valuable and rewarding investment in the vibrant Southlake market.


For those looking to invest in luxury homes in Southlake, Texas, Nitin Gupta is an expert real estate professional ready to assist. Known for his extensive experience, market insights, and numerous awards, he is committed to finding his clients the best properties in the area.


Contact Nitin Gupta at 469-269-6541 or send a message today to explore exclusive listings and secure your ideal luxury residence in one of Southlake’s elite communities.




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