Westport Waterfront Real Estate: The Ultimate Guide to Buying and Selling Coastal Homes in Westport, Connecticut

Westport Waterfront Real Estate blends classic New England charm with a luxurious coastal lifestyle on the Long Island Sound. From sunrises over Compo Beach to sunset cruises along the Saugatuck River, Westport’s shoreline delivers year-round beauty, top-tier amenities, and strong long-term value. Whether you’re dreaming of a direct waterfront estate with a private dock, a beach-area cottage you can rebuild or expand, or a riverfront condo steps from downtown, Westport offers a diverse range of options for discerning buyers and sellers.

As a local real estate advisor with Century 21 Scala Group, I, Esther Lamy, help clients navigate the nuances that make Westport Waterfront Real Estate unique: FEMA flood zones, elevation certificates, dock permitting, mooring availability, coastal construction guidelines, and pricing premiums tied to view, exposure, and access. Below is a comprehensive, practical guide to help you make the most informed decision on the water in Westport, Connecticut.

Why Westport’s Waterfront Is So Coveted

Few coastal towns balance everyday convenience with true resort-style amenities like Westport:

• Two Metro-North stations (Westport/Saugatuck and Greens Farms) for a convenient commute to New York City.
• Public and private shoreline features including Compo Beach, Burying Hill Beach, Old Mill Beach, Sherwood Island State Park, the Saugatuck River, and the Sherwood Mill Pond.
• Longshore Club Park’s 18-hole golf course on the water, town marina, tennis, paddle, pool, and the Longshore Sailing School.
• A vibrant downtown along the Saugatuck River with boutique shopping, the Westport Library, seasonal events at the Levitt Pavilion for the Performing Arts, and riverside dining.
• Strong schools, including nationally recognized Staples High School, making Westport a perennial favorite for families.

Lifestyle plus liquidity. Waterfront homes in Westport tend to hold value better over long horizons, thanks to limited supply and sustained demand from tri-state buyers who want the coastal experience without sacrificing schools, culture, or commuting options.

Westport Waterfront Real Estate at a Glance

• Property types: Direct waterfront estates with private docks, tidal marsh-view homes, beach-area cottages, riverfront condos/townhomes, and new-construction builds elevated to current coastal standards.
• Neighborhoods: Saugatuck Shores and Saugatuck Island, Compo Beach and Old Mill, Greens Farms (Burying Hill), and riverfront corridors near downtown.
• Premium drivers: Navigable deep-water docks, unobstructed Long Island Sound views, southern exposure, beach proximity, deeded beach rights, elevation above Base Flood Elevation, and modern coastal construction.
• Considerations: Flood zones (AE, VE), elevation certificates, flood insurance, coastal permitting for docks and seawalls, mooring availability via the harbormaster, and potential association bylaws in areas like Saugatuck Island.

Neighborhood Spotlights: Where to Find Your Perfect Waterfront

Saugatuck Shores and Saugatuck Island - Character: A boater’s paradise—peninsulas, canals, and open-sound frontage. You’ll find everything from mid-century ranches updated and elevated to contemporary glass-and-shingle showpieces with docks. - Access: Quick route to I-95 and the Westport train station, plus easy runs by boat to Cockenoe Island and beyond into Long Island Sound. Many streets enjoy water views in multiple directions. - Lifestyle: Walk, run, or bike with water on both sides; watch regattas and sunsets; enjoy a true maritime community. Some blocks fall under association guidelines; dock permitting varies by location and water depth.

Compo Beach and Old Mill - Character: Classic beach-town vibe with a mix of cottages, renovated homes, and standout new builds. Old Mill Beach sits at the edge of Sherwood Mill Pond, offering a unique, intimate coastal feel. - Access: Compo Beach draws residents year-round—morning walks, paddleboarding, winter sunrise photos, and summer fireworks. Old Mill offers calm-water paddling and scenic views of the Mill Pond and Sound. - Lifestyle: Salt air, sand, and simplicity. Homes close to Compo fetch premiums for walkability and beach access.

Greens Farms and Burying Hill - Character: Stately residences and estate parcels, some with water views or private paths to the sand. Burying Hill Beach is smaller and serene, a local favorite for a quiet afternoon by the water. - Access: Convenient to the Greens Farms train station, beloved for express options and lighter crowds. Certain streets offer bluff-top views and a sense of privacy. - Lifestyle: Understated elegance with proximity to shoreline parks and walking trails.

Downtown and the Saugatuck River - Character: Riverfront condos and single-family homes within steps of the library, shopping, and dining. Some communities offer terraces and decks overlooking the river—perfect for those who want water views and in-town convenience. - Access: Walk to festivals at the Levitt Pavilion, scenic river walks, and easy drives to either train station. - Lifestyle: Urban-meets-coastal, ideal for downsizers, pied-à-terre buyers, and anyone craving a low-maintenance, water-adjacent life.

The Coastal Lifestyle: Beaches, Boating, Golf, and the Arts

• Beaches: Compo Beach is the town’s social shoreline, great for swimming, volleyball, playgrounds, and sunsets. Burying Hill is quieter and more intimate; Old Mill is a charming neighborhood strand at the edge of Sherwood Mill Pond.
• Boating: Longshore Club Park’s marina and sailing school make it easy to learn or store your boat; mooring permits are managed locally. From Westport, boaters head to Cockenoe Island for sandy beaches and birding, or farther into the Sound for fishing and cruising.
• Recreation: Longshore’s waterfront golf course is a gem, with water views from the fairways. Tennis, paddle, and a seasonal pool round out the offerings. Kayakers and paddleboarders enjoy calm mornings at the Mill Pond and along the Saugatuck River.
• Culture: Westport’s arts scene thrives, anchored by the Westport Country Playhouse, the Levitt Pavilion’s free summer concerts, and community programming at the library—many events set right on the water.

Buying Smart: Permits, Flood, Docks, and Due Diligence

Coastal homes come with specialized considerations. A strategic approach protects your lifestyle, timeline, and budget.

• Flood zones and elevation: Many shoreline properties are in AE or VE zones. Ask for the elevation certificate, confirm the Base Flood Elevation, and evaluate how the home is built (elevated pilings, breakaway walls, flood vents). Higher elevation or compliant construction can mean lower flood insurance costs and greater resilience.
• Insurance: Get multiple quotes early. Premiums vary based on elevation relative to BFE, enclosure types, and mitigation features. If you plan renovations, your architect/engineer can design for compliance and cost efficiency.
• Docks and moorings: Private docks require state approvals and can be complex. Verify existing permits, maintenance history, and water depth at low tide. If you plan to add or expand a dock, consult on feasibility upfront. Alternatively, explore moorings through the local harbormaster at Longshore or Saugatuck.
• Seawalls and shoreline stabilization: Not all properties have or need a hard structure. Some sites benefit from living shorelines or hybrid solutions. Review condition reports and ask about recent storm performance and repairs.
• Utilities and systems: Many coastal pockets are on public water and sewer, but not all. Confirm whether the property has natural gas service, public sewer, or a private septic system; if septic, evaluate age, size, and location relative to coastal setbacks.
• Building and renovating: Waterfront work often requires Coastal Area Management (CAM) review and state oversight. Build timelines can lengthen without proper planning—engage coastal-savvy engineers, contractors, and permit expediters early.
• Title and associations: In Saugatuck Island and some beach-area enclaves, ask about association fees, road maintenance, beach rights, and any rules governing docks, fences, or exterior materials.

Pro tip: I connect buyers with trusted coastal engineers, marine contractors, insurance advisors, and lenders experienced with flood zones to streamline diligence and avoid surprises.

Market Snapshot: Pricing, Inventory, and What Wins Offers

Westport Waterfront Real Estate is a niche-within-a-niche. Inventory is limited and often privately shopped before hitting the open market.

• Pricing tiers: Riverfront condos and townhomes near downtown can range from the upper six figures to well into seven figures depending on size, finishes, and view corridors. Beach-area single-family homes typically start in the multimillion range, with new or fully renovated properties commanding significant premiums. Direct Sound-frontage estates with docks and panoramic views can crest much higher, especially with acreage or exceptional architecture.
• What drives price: Navigable deep-water access and protected dockage are at the top of the value pyramid. After that: unimpeded views, southern exposure, modern coastal construction above BFE, walkability to beaches, and proximity to train stations.
• Competition: Cash and strong conventional buyers are common. Flexible closing timelines, limited contingencies, and pre-offer inspections (when feasible) can make the difference.
• Off-market deals: In a tight waterfront market, relationships matter. I regularly track whisper listings and upcoming inventory so clients can position themselves ahead of the crowd.

Selling a Waterfront Home: Maximize Your Return

Showcasing a coastal property requires more than standard staging. My comprehensive approach through Century 21 Scala Group is built for the shoreline:

• Visual storytelling: Drone photography to capture setting and approach; twilight images to showcase reflections and lighting; floor plans and 3D tours to articulate flow; lifestyle vignettes emphasizing decks, docks, and beach proximity.
• Data-forward positioning: Clear disclosure of elevation certificates, flood mitigation features, and any recent coastal upgrades. Buyers pay a premium for peace of mind.
• Seasonal strategy: Listing near peak shoreline appeal can pay dividends, but serious waterfront buyers are active year-round. We’ll identify the optimal launch window for your property type.
• Pricing intelligence: We evaluate recent comparable sales by micro-location (canal vs. open Sound, beach adjacency, riverfront downtown) and adjust for view, exposure, and water access—not just bed/bath counts.
• Showing management: Tide charts matter. For homes with docks or marsh views, timing showings to highlight water levels and light conditions can materially impact perceived value.

Investment and Rental Potential

• Seasonal demand: Summer and early fall see heightened interest from relocating families and executives seeking a coastal test-drive before buying.
• Furnished options: Well-appointed, water-adjacent homes can secure premium monthly rates, especially with flexible terms for corporate or relocation tenants.
• Regulations: Westport has guidelines governing rentals and occupancy; ensure your plan aligns with town requirements and any neighborhood association rules. I advise clients on practical pathways and help coordinate the right legal and property management resources.
• Long-term value: Limited inventory on the coast, combined with Westport’s schools and amenities, has historically supported strong appreciation and resilient resale prospects.

How I Help: The Esther Lamy and Century 21 Scala Group Advantage

Choosing the right agent is critical with Westport Waterfront Real Estate. My practice is built on local insight, meticulous due diligence, and seamless execution:

• Coastal expertise: I translate flood maps, elevation data, and permit history into clear guidance. You’ll understand what matters and why before you commit.
• Powerful marketing: Century 21 Scala Group’s platform amplifies your property across targeted digital channels and qualified buyer networks, with high-impact creative tailored to waterfront homes.
• Pro network: I’ll introduce you to the area’s go-to coastal engineers, surveyors, marine contractors, insurance specialists, inspectors, and lenders familiar with flood zones and dock-related underwriting.
• Negotiation and timing: Waterfront deals can hinge on contingencies around permits, moorings, or insurance. I navigate those pain points proactively, keeping your goals front and center.
• Quiet opportunities: Through consistent outreach and relationships, I uncover upcoming listings and off-market prospects so my clients can act early and with confidence.

Next Steps: Your Path to the Water

For Buyers - Define your must-haves: dock vs. mooring, beach proximity, commute, exposure, and views. - Get financially ready: engage a lender experienced with coastal properties or prepare proof of funds for cash. - Preview with purpose: tour across neighborhoods—Saugatuck Shores, Compo/Old Mill, Greens Farms—to calibrate value and understand tradeoffs. - Plan diligence: line up insurance quotes, a coastal-savvy inspector, and any specialty evaluations for docks or seawalls before you write, when possible.

For Sellers - Gather documentation: elevation certificate, recent improvements, dock permits, and flood insurance details. - Make smart updates: simple exterior refreshes, deck maintenance, and window cleaning for crystal-clear views deliver outsized returns. - Stage for lifestyle: showcase outdoor living, easy beach access, and unique vantage points that make your home unforgettable. - Choose marketing built for the shoreline: demand drone, twilight, floor plans, and targeted audience strategies—then monitor real-time engagement to fine-tune.

Final Word: Make the Water Your Everyday

Westport Waterfront Real Estate is more than a home—it’s a way of life shaped by tides, light, and community. With the right guidance, you can navigate the complexities of coastal ownership and capture the unmatched benefits of living on the Sound.

If you’re considering buying or selling on the water in Westport, I’m here to help—from early strategy through a smooth closing. I’m Esther Lamy with Century 21 Scala Group, and I’d be honored to be your trusted advisor on the shoreline. Reach out to start a tailored plan that aligns with your timing, budget, and vision.