TLB | Deal or No Deal? #002 - 50 Eveningside Dr, Milford, CT

Hello and welcome to this week’s The Local Block!

Today, we’re heading to 50 Eveningside Drive, Milford, CT, a property that’s been lingering on the market for years.

With a long and messy price history, inconsistent listings, and a recent lis pendens* filing, this seller might finally be ready to make a deal.

📍 The Deal at a Glance

🏡 List Price: $2,499,000 (or is it $2,900,000? Depends where you look.)
📏 Size: 5,500 sq. ft. or is 4,500 sq. ft. (Depends where you look.)
💰 Price per Foot: $435 for 5,500 sq. ft.(in line with recent comps)
💰 Price per Foot: $555 for 4,500 sq. ft.

This home has bounced around from agent to agent and price to price since 2018, creating what I call a “bad rap sheet” on Zillow.

Buyers (and agents) tend to avoid properties like this because they scream “I don’t really want to sell.”


📊 Market Breakdown

13 homes over $1.5M have sold in Milford in the past year.

7 homes over $2M sold, mostly waterfront, unlike this one.

• Competing listings include larger, better-located homes priced similarly.

• The owner has an $868K mortgage at 6% and recently had a lis pendens filed—suggesting financial distress.

💡 What’s the Play Here?

The seller has wasted years playing the pricing game, but with foreclosure potentially looming, time is running out. Given the comps, the real sale price might get quite aggressive depending on seller motivation.


Bottom line: If you’re looking for a deal near a Connecticut beach, this one might finally be primed for negotiation.


Want my full breakdown?


Until next time,

Mike Russo

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*Lis Pendens was found on Propwire.com

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Each week, I bring you a great property with a highly motivated seller. I break down the listing, the market, and what it would take for you to close the deal.