Westport: A Mosaic of Luxury Living

Westport isn’t one-size-fits-all. It’s a collection of distinct neighborhoods, each with its own luxury flavor. From beachside cottages with million-dollar views to historic Colonial estates, choosing the right neighborhood is as important as choosing the right house.

The good news? You’ve got options. The challenge? Making the right match. Let’s break it down.

Old Hill: Timeless Character Meets Privacy

Old Hill is one of Westport’s most historic enclaves. Here you’ll find Colonial and early-American homes on generous 1–3 acre lots, often framed by stone walls and leafy drives. Its close proximity to downtown and the Earthplace Nature Center makes it feel both connected and serene.

• Buyer Fit: Families seeking privacy, community, and architectural pedigree.

Greens Farms: Westport’s Oldest & Most Elegant

Greens Farms is steeped in history and prestige. Large estates, private roads, and Greens Farms Academy anchor the area. Commuters appreciate easy Metro-North access, while Sherwood Island State Park provides an outdoor playground.

• Buyer Fit: Those craving historic prestige, privacy, and easy highway/train access.

Compo Beach & Compo–Owenoke: Coastal Charm

If you dream of living steps from the sand, Compo Beach delivers. This district combines a beach-resort vibe with classic Westport architecture—think waterfront Colonials, summer cottages turned year-round luxury, and sweeping views of Long Island Sound.

• Buyer Fit: Buyers prioritizing lifestyle, beach access, and salty breezes.

Saugatuck & Saugatuck Shores: Waterfront Energy

Saugatuck has transformed into a buzzing hotspot with chic restaurants, arts venues, and walkable streets. Head to Saugatuck Shores, and you’ll find peninsula-style living with docks, panoramic water views, and access to kayaking and boating.

• Buyer Fit: Buyers wanting both energy and waterfront elegance.

In-Town (Westport Village): The Heartbeat

In-town living means everything is at your doorstep—shops, restaurants, theaters, and cultural venues. Homes here are quaint and walkable, while developments like Bedford Square add a cosmopolitan edge.

• Buyer Fit: Buyers craving convenience, culture, and walkable luxury.

Other Notable Areas

• Coleytown: Spacious estates, a highly sought-after address, and a blend of tradition and modern builds.

• Long Lots: Known for Staples High School and family-friendly layouts with quick access to parks and town.

• Red Coat: A commuter-friendly, quiet neighborhood with privacy and access to all major Westport amenities.

The Market Perspective

Westport’s luxury market remains robust:

• Median listing price: ~$2.9M (up ~4% year-over-year).

• Median sale price: ~$1.95M, with price per square foot up 10% YoY.

• Inventory remains tight, with homes under $2M moving quickly (average ~44 days on market).

Translation: Choosing the right neighborhood now is crucial—supply is low, demand is high, and lifestyle-driven buyers are willing to pay premiums.

Match Your Personality to the Right Neighborhood

• Heritage Collector: Old Hill or Greens Farms.

• Seaside Daydreamer: Compo Beach or Saugatuck Shores.

• Social Navigator: In-Town.

• Family First: Long Lots or Coleytown.

• Commuter-Historic Hybrid: Red Coat.

6) Call to Action

Choosing the right neighborhood in Westport isn’t just about a home—it’s about lifestyle, investment, and long-term value. At The Collection – By Dave Jones, we specialize in matching buyers with the neighborhoods that fit their goals, whether that’s coastal glamour, historic prestige, or in-town vibrancy.

The Collection – By Dave Jones
40 Center Street, Prospect, CT 06712
Phone: 203-910-2638 • Email: [email protected] • Web: TheCollectionCT.com