From a coastal retreat to a private estate with a tennis court, I compare four very different Westport homes that all landed near the same price.
Here's a question I like to ask buyers who are curious about this market: if I handed you $3 million and told you to spend it in Westport, where would it go? I didn't pick that figure at random. It's right around the average selling price in town so far in 2026, and the fascinating part is how little that number actually tells you. Four homes can sell for about the same price and still offer four completely different ways of living. $3 million doesn't buy a single answer, so let me show you what I mean.
3 Nassau Road in Saugatuck Shores
If your idea of home leans toward the water, Saugatuck Shores makes a strong case. This 2021-built home offers about 3,486 square feet, five bedrooms, and four bathrooms on a quarter-acre lot, and every part of it is built around lifestyle rather than square footage. The heated saltwater gunite pool and rooftop deck are made for long evenings and easy entertaining, and the water views are the kind you don't get tired of. What ties it together is location. You're minutes from the Metro North train, Compo Beach, Longshore, and downtown, so the coastal lifestyle here comes with real convenience, not a trade-off for it.
16 Gault Park Drive
Trade the water for land, and you land at Gault Park Drive, a modern farmhouse on just over an acre. At nearly 4,735 square feet with five bedrooms and four and a half baths, this one is about room to live rather than a showpiece backyard. There's no pool, though there's space to add one, and the interior is where it earns its price: a chef's kitchen, an elevated family room with exposed beams, a first-floor guest suite, a dedicated home office, a mudroom, and a second family room upstairs. For a family that wants a classic New England feel, flexible space, and proximity to town, the train, the beach, and award-winning schools, this home covers a lot of ground.
“Four Westport homes sold for right around the same price, and no two of them are alike.”
35 Woody Lane
Where the first two homes ask you to choose between water and space, Woody Lane just hands you the most land of the group, over 2.18 acres, and turns the backyard into the headline. The house itself is comfortable at almost 4,486 square feet with five bedrooms and three and a half baths, but people remember the outdoor space: a heated gunite pool, a full tennis court, a hot tub, a fire pit, an expansive deck, and complete privacy. It plays like a private resort you never have to leave, and you're still only minutes from top schools, Compo Beach, and the train. For a buyer whose wish list starts outside the front door, this one is tough to beat.
36 Bauer Place Extension
And if newer and bigger is the goal, the newest home of the four answers it. Built in 2024, Bauer Place Extension is also the largest at nearly 5,938 square feet, with six bedrooms and five and a half baths spread across four finished levels. There's no pool here either, but the square footage does the work: a lower level with a custom gym, sauna, and full baths, and a third floor that flexes into a guest suite, a playroom, or a home office. Add in a short hop to shopping, restaurants, Long Lots Elementary, and the Greens Farms train station, and it's the pick for a buyer who wants brand-new construction with plenty of room to spread out.
So back to my question. At roughly the same price, you can have the coastal ease of Nassau Road, the farmhouse and acreage at Gault Park Drive, the resort-style estate on Woody Lane, or the brand-new, 6,000-square-foot build on Bauer Place Extension. There's no wrong answer, only the one that fits how you actually want to live, and I'd genuinely love to hear which way you'd go and why, because that's the fun part.
If you're curious what your budget buys here in Westport, or if you're thinking about selling your home here, please reach out. I'd be happy to help. Give me a call at (203) 722-5445, email me at [email protected], or visit lindadunsmore.com. I look forward to helping you find the right fit.
