Top 10 Realtors in Westport, CT
Market Overview
Westport's luxury real estate market demands exceptional expertise, with median home prices reaching $2.1 million in 2025—a 13.5% increase year-over-year. The town's unique combination of waterfront estates, historic properties, and proximity to Manhattan creates a specialized market requiring agents with deep local knowledge, proven luxury credentials, and outstanding client service.
Key Market Statistics
- Median Home Price: $2.1 million (↑13.5% YoY)
- Luxury Segment Median: $2.9 million
- Average Days on Market: 54 days
- Cash Buyers: 47% of transactions
- NYC Buyer Percentage: 20% of purchases
The following rankings consider comprehensive performance metrics from over 278 sources including annual sales volume, years of market experience, professional designations, client satisfaction ratings, community involvement, and specialized expertise in Westport's distinctive luxury market.
- Coldwell Banker Realty- #1 Westport listing agent for 9 consecutive years (2016-2024)- Former KPMG CPA providing unique financial expertise- $550+ million career sales over 30+ years- ⭐ 280+ five-star reviews with perfect 5.0/5.0 Zillow rating- #6 real estate professional in Connecticut statewideThe undisputed market leader stands alone as Westport's premier real estate professional. Michaelis brings unmatched combination of financial expertise from her KPMG background, community deep-rootedness as a founding agent of Coldwell Banker's Westport office, and proven performance with 75 homes sold totaling over $150 million in recent years. Her "When you hire Judy, you get Judy" service philosophy and innovative marketing including Kitchen Crawls and Jazz Brunches set her apart in the luxury market.
- Coldwell Banker Global Luxury- #33 real estate team in America (Real Trends/WSJ)- $2.5+ billion career sales- $214 million single-year volume- $10 million highest 2024 residential sale in Westport
Elite team dominating luxury sales through sheer volume and national recognition. Led by Barbara Bross (25+ years experience) and Alexander Chingas, this powerhouse team maintains their position through Global Luxury Property Specialist designations and representation of ultra-luxury properties, including Westport's highest residential sale of 2024.
- Compass- #1 Compass team in Connecticut- MBA Marketing, BA Finance & Economics- 90% repeat and referral business- $15.175 million off-market transaction- ️ Founding members of Compass Westport
Pioneering luxury approach with exceptional off-market capabilities and client relationship excellence. Scott's educational background provides analytical foundation crucial for luxury market success, while their "Real Estate Partners for Life" approach reflects the long-term relationship building essential in Westport's affluent community.
- William Pitt Sotheby's International Realty- Top individual agent at William Pitt Westport- Top 3 agents across all of Westport- Fortune 500 marketing background- Investment property specialist- ⏰ 24/7 availability with data-driven approach
Individual excellence in specialized markets with sophisticated brand positioning skills from Fortune 500 experience. Her transition from Manhattan to Westport provides unique insight into buyer motivations, while her investment property specialization adds value in a market where buyers view real estate as both lifestyle and financial investments.
- William Pitt Sotheby's International Realty- 25+ years Fairfield County resident- Full-service team approach- Established network of professionals- Comprehensive transaction management- Generational market knowledge
Comprehensive team approach with extensive generational market knowledge. Walters' 25+ years as a lifelong Fairfield County resident provides invaluable insight into Westport's complex luxury landscape of waterfront estates, historic properties, and new construction developments.
- Coldwell Banker Realty- $500+ million luxury property sales- International President's Elite Circle (top 1%)- 18+ years Fairfield County luxury markets- 5-Star recognition Connecticut Magazine- Top 1% Coldwell Banker agents internationally
Proven luxury market expertise with over half a billion in luxury sales and consistent top-tier recognition. Her 18+ years specifically in Fairfield County luxury markets demonstrates both longevity and consistent excellence in the region's most demanding market segments.
- Compass- 26+ years coastal luxury market- Consistent top producer recognition- Waterfront property specialists- ️ Private beaches and sailing communities expertise- Deep understanding coastal living appeal
Coastal luxury specialists with deep understanding of Westport's unique waterfront market. Their 26+ years serving the luxury coastal market provides specialized expertise crucial for the town's distinctive private beaches and sailing community lifestyle.
- William Pitt Sotheby's International Realty- Real estate attorney assistant background- General contractor expertise- Building regulations & zoning specialist- Conservation issues expert- ️ Complex regulatory environment navigation
Legal and construction expertise providing unique value in Westport's complex regulatory environment. Her background as real estate attorney assistant and general contractor offers sophisticated understanding of building regulations, zoning requirements, and conservation issues critical for luxury properties.
- Houlihan Lawrence- $220+ million in 2024 sales- Close to $1 billion career sales- Zillow Agent Advisory Board- Proven team approach- Greenwich-based expanding to Westport
High-volume team approach bringing proven Greenwich luxury market success to Westport. Their impressive 2024 sales volume and close to $1 billion career sales, combined with Zillow Agent Advisory Board expertise, provides discerning Westport clients with top-tier service.
- Houlihan Lawrence- #1 volume producer Houlihan Lawrence New Canaan- Real Trends "America's Best" recognition- ✈️ Certified relocation specialist- ️ NYC buyer specialist (20% of market)- Lower Fairfield County expertise
Relocation and NYC buyer specialist with national recognition and volume production leadership. Her certification as relocation specialist proves particularly valuable in Westport's market where 20% of buyers come from New York City requiring sophisticated relocation services.
Market Leadership in America's Premier Luxury Market
These top 10 realtors represent the pinnacle of luxury real estate expertise in one of America's most sophisticated markets. Their success reflects not only individual achievement but also deep understanding of what makes Westport unique—from its world-class schools and cultural amenities to its coveted Long Island Sound waterfront and proximity to Manhattan's financial centers.
In a market where premium neighborhoods like Greens Farms ($4.9 million median), Compo-Owenoke Historic District ($4.2 million median), and Saugatuck ($3.9 million median) require specialized knowledge of waterfront regulations, historic preservation requirements, and community amenities, only experienced local agents with proven track records can deliver the results luxury clients demand.
With inventory at critically low levels and homes above $2 million commanding premium prices while selling quickly, these agents possess the relationships, market knowledge, and luxury credentials necessary to navigate Westport's competitive real estate landscape successfully.
