Looking for a coastal Connecticut gem with upscale charm? Westport offers a blend of luxury living and small-town appeal that continues to attract homebuyers despite market fluctuations. The town’s real estate landscape showcases stunning waterfront properties and historic homes nestled in picturesque neighborhoods.
The Westport, CT housing market is currently valued at approximately $1.7 million for the average home, with prices up 3.6% over the past year according to recent market data. While this represents a significant investment, the town delivers exceptional value through its top-rated schools, vibrant downtown, and convenient location just an hour from New York City. The market remains somewhat competitive, offering opportunities for both buyers and sellers.
Get a discount of 15% to 70% on accommodation in Connecticut! Look for deals here:
Connecticut Hotels, Apartments, B&Bs
Visitors to Westport will discover why this affluent community has long been a favorite among celebrities, executives, and families seeking an idyllic New England lifestyle. The town’s combination of cultural attractions, beautiful beaches, and luxury properties creates an irresistible appeal that continues to strengthen its real estate market, even as nearby areas experience more volatility.
Understanding Westport’s Housing Market
Westport’s real estate landscape offers a mix of competitive pricing, diverse property types, and distinct neighborhood characteristics that shape buying and selling decisions. The market continues to evolve with notable price fluctuations influenced by broader economic factors.
Current Market Conditions
Westport’s housing market is currently classified as somewhat competitive, scoring 49 out of 100 on competitiveness scales. This moderate level means buyers have reasonable negotiating power while sellers still maintain some advantages.
The inventory situation shows approximately 143 homes for sale across Fairfield County’s Westport area. This provides buyers with options but doesn’t indicate a flooded market.
Market activity has seen some interesting shifts recently. The average Westport house price was $1.58 million in early 2025, reflecting a 16.3% decrease since the previous year. This represents a cooling from the remarkable 2021 market when the median price reached $1.6 million—a 42% increase from 2019 levels.
Timing remains favorable for sellers despite recent adjustments, as demand for Westport properties continues to be stable despite price corrections.
Types of Properties Available
Westport’s property landscape features diverse housing options with single-family homes dominating the market. These range from modest three-bedroom properties to expansive luxury estates.
Property Types in Westport:
- Traditional colonial-style homes
- Modern waterfront properties
- Historic New England houses
- Luxury estates on multi-acre lots
- Contemporary new constructions
High-end properties command significant premiums, with some luxury homes like 31 Woody Lane listed at $5,495,000 featuring 6 bedrooms and over 10,000 square feet. Meanwhile, more modest homes remain available at various price points.
The housing stock includes both historic properties with character and new construction with modern amenities. This diversity appeals to a wide range of buyers, from young families to empty nesters looking to downsize.
High-Demand Neighborhoods
Westport’s most coveted areas combine excellent schools, convenience to amenities, and distinct character. The 06880 zip code remains particularly desirable, representing the town’s core area with its mix of historic charm and modern conveniences.
Neighborhoods near Compo Beach offer the appeal of coastal living with walkability to sandy shores. These waterfront and water-adjacent properties typically command premium prices but provide lifestyle benefits that many buyers prioritize.
The Greens Farms area attracts families seeking larger lots and a more suburban feel while maintaining proximity to town amenities. Its excellent school district further enhances appeal.
Old Hill and Coleytown neighborhoods feature winding roads, mature trees, and a mix of architectural styles that appeal to those seeking established communities with character.
Westport’s downtown-adjacent neighborhoods offer walkability to shops and restaurants, appealing to buyers looking for convenience without sacrificing space.
Price Trends and Predictions
Westport real estate has experienced notable price fluctuations recently. The median listing home price reached $3 million in late 2024, representing a 14.9% year-over-year increase. This contrasts with the earlier mentioned average price decrease.
Price per square foot metrics provide additional perspective, with Westport homes commanding approximately $691 per square foot. This premium reflects the town’s desirability and quality of construction.
Historical data shows Westport’s resilience through market cycles. After the explosive growth of 2021, prices stabilized rather than crashed dramatically, indicating market strength.
Analysts suggest the Westport market will remain stable through 2025, with modest appreciation expected. The median price of $1,903,033 represents a 2.2% increase year-over-year, pointing to continued but measured growth.
Factors influencing future prices include limited inventory, continued demand for suburban living, and Westport’s enduring appeal as a commuter town with exceptional schools and amenities.
Infrastructure and Accessibility
Westport offers exceptional infrastructure that blends modern convenience with small-town charm. The town’s thoughtful development provides residents with outstanding transportation options, community facilities, educational institutions, and a robust economic foundation.
Transportation Networks
Westport enjoys strategic positioning along Connecticut’s transportation corridor, making it ideal for commuters and travelers alike. The town is served by two Metro-North Railroad stations (Westport and Green’s Farms), offering frequent service to New York City with travel times averaging 70-75 minutes.
Interstate 95 runs through Westport, providing direct highway access to major Northeast cities. The Merritt Parkway (Route 15) offers a scenic alternative for north-south travel. Local bus services connect neighborhoods to the town center and train stations.
For water enthusiasts, Westport’s location on Long Island Sound provides recreational boating access, with several marinas and public boat launches available.
Westport has also invested in pedestrian and cycling infrastructure, with dedicated paths and bike lanes throughout popular areas, encouraging eco-friendly transportation options.
Community Amenities
Westport boasts exceptional public facilities that enhance residents’ quality of life. The town features multiple pristine beaches including Compo Beach and Burying Hill Beach, where residents can swim, picnic, and enjoy outdoor activities with stunning Long Island Sound views.
Longshore Club Park spans 169 acres offering an 18-hole golf course, tennis courts, swimming pools, and sailing facilities. The Westport Library, recently renovated with state-of-the-art technology, serves as a community hub with extensive programming.
Levitt Pavilion hosts free summer concerts in its outdoor amphitheater, bringing world-class entertainment to residents. The town’s vibrant downtown area features upscale shopping, dining options, and the historic Westport Country Playhouse.
Multiple parks and nature preserves, including Winslow Park and Sherwood Island State Park, provide extensive green spaces for recreation and relaxation.
Schools and Education
Westport’s public school system consistently ranks among Connecticut’s finest educational institutions. The district includes five elementary schools, two middle schools, and Staples High School—regularly rated among the top public high schools nationally for academic excellence.
The town invests heavily in educational infrastructure, with modern facilities, advanced technology integration, and robust extracurricular programs. Student-teacher ratios remain favorable, allowing for personalized attention.
Beyond public education, Westport hosts several prestigious private schools and specialized learning centers. The town’s commitment to education extends to adult learning through community programs and workshops.
Westport’s proximity to prestigious universities like Yale, Fairfield University, and Sacred Heart University provides residents with access to higher education opportunities, contributing to the town’s intellectual atmosphere and lifelong learning culture.
Economic Indicators
Westport maintains a robust economic foundation evidenced by its thriving commercial districts and strong property values. The median home price in Westport was $1.58 million as of early 2025, though prices have seen some fluctuation.
The town features a diverse economic base with sectors including finance, marketing, retail, and professional services. Main Street and surrounding areas host boutique shops, galleries, and restaurants that contribute to the local economy.
Westport’s economic stability benefits from its proximity to major corporate centers in Stamford and New York City. Many residents hold executive positions in these nearby business hubs while enjoying Westport’s residential charm.
Commercial real estate remains in high demand, with low vacancy rates in prime retail and office spaces. The town’s economic development commission actively works to maintain business-friendly policies while preserving Westport’s distinctive character.
Get a discount of 15% to 70% on accommodation in Connecticut! Look for deals here:
Connecticut Hotels, Apartments, B&Bs
Fairfield County
Hartford County
Litchfield County
Middlesex County
New Haven County
New London County
Tolland County
