Lakeside, Michigan Real Estate Market Analysis

Lakeside, Michigan Real Estate Market Analysis
By Carlos Pagán & Scott Popp – Team Popp | Live Lake Michigan

Why Lakeside Belongs on Your Short List

Lakeside is one of Harbor Country’s most intimate pockets on the Lake Michigan shoreline—quiet, tree-lined, and built for people who want a slower pace without giving up convenience. It’s an unincorporated community in Chikaming Township with only about 200–250 residents, known for historic summer cottages, a strong homeowner association, and community events like the Memorial Day Parade and summer ice cream social.

For our Chicago clients, this is the “exhale” zone: roughly 75 miles and about 1 hour 20 minutes from downtown via I-94, making it a true weekend (or three-day-weekend) market, not a “fly-to-get-there” destination.

This is exactly where Live Lake Michigan becomes a lifestyle, not just a slogan.

Current Market Snapshot: Lakeside & ZIP 49116

Data is limited because Lakeside is tiny and skewed toward luxury and second homes, so every sale moves the numbers. That said, a few trends are clear:

• Typical Home Value (All Property Types):
  The average Lakeside home value is about $818,590, up 3.4% over the past year as of October 31, 2025.
• Recent Sale Prices (49116):
  In October 2025, the median sale price in ZIP 49116 (which includes Lakeside) was about $1.1M, with sale prices per square foot around $699, up sharply year over year. Homes are taking a median of about 61 days to sell, and only a handful of properties trade hands each month.
• Harbor Country Outlook:
  Across Harbor Country—New Buffalo, Union Pier, Lakeside, Harbert, Sawyer—2025 is expected to remain a seller-leaning market, particularly for lakefront and vacation-heavy areas, driven by strong second-home demand and limited inventory.
• Michigan Macro Context:
  At the state level, Michigan overall is shifting toward a more balanced market in 2025, with moderate price growth and buyers adjusting to 6.5–7% mortgage rates.
  Lakeside, however, behaves differently than “average Michigan” because it’s a small, luxury-dominated, second-home submarket.

Our take (Carlos & Scott):
Lakeside is a thin-traded, high-value market with steady upward pressure on values and very limited inventory. The stats will look “jumpy” month-to-month because two or three big lakefront sales can swing the medians, but the direction over time is clear: Lake-adjacent and well-renovated properties are holding and growing their value.

Who’s Buying in Lakeside Right Now?

From what we’re seeing and what the data supports in Harbor Country:

• Chicago & Suburban Professionals:
  People who want to swap Lake Shore Drive for Lake Michigan sand on Friday evenings. Many work hybrid or remote schedules and see Lakeside as both a retreat and a “second HQ.”
• Second-Home & Investment Buyers:
  Buyers looking for vacation homes that can double as long-term lifestyle plays and, in some cases, strategic short-term or seasonal rentals (where permitted by local rules).
• Legacy & Lifestyle Buyers:
  Families who want to pass down a Lake Michigan property—something they can actually use now and future generations can inherit.

In other words: fewer buyers overall, but a high-intent, high-capacity buyer pool.

Lifestyle Advantage #1: Small-Town Harbor Country Vibe

Team Popp loves the area!  Lakeside is part of Harbor Country, eight small towns along the southwest Michigan shoreline: Michiana, Grand Beach, New Buffalo, Union Pier, Lakeside, Harbert, Sawyer, and Three Oaks.

What makes Lakeside special within that chain:

• “Slower Pace” DNA:
  The Chamber literally describes Lakeside as “a warm and inviting place to embrace a slower pace,” with many residents living in restored historic summer cottages and participating in local traditions and events.
• Historic Lodging & Architecture:
  The Lakeside Inn is a Harbor Country landmark, with a 100-foot porch facing Lake Michigan and a private beach—showing the heritage of the area as a summer destination since the early 1900s.
• Community Feel:
  An active homeowner association, annual Memorial Day Parade, and summer Ice Cream Social create a sense of “everyone knows your name,” which is rare in many second-home markets.

When we say Live Lake Michigan, in Lakeside that means: beach walks, porch time, and neighbors who actually wave back.

Lifestyle Advantage #2: Proximity to Chicago (Without the Chaos)

For Chicago-based buyers, Lakeside hits the sweet spot:

• Around 68–75 miles from Chicago, roughly 1 hour 20 minutes by car via I-94 under normal conditions.
• Time zone is Eastern, so your weekend “feels” longer even though the drive is short.
• Easy access to Chicago via driving or by leveraging the New Buffalo Amtrak connection for some trips.

From a lifestyle and investment standpoint, that proximity helps support demand and long-term value—because Lakeside is close enough to be used often, not just a once-a-year destination.

Lifestyle Advantage #3: Food & Restaurants – Small Radius, Strong Options

Lakeside itself and its immediate neighbors along Red Arrow Highway and into Union Pier/New Buffalo create a surprisingly strong food ecosystem for such a small market:

• Sonny D’s –  Ask for the Jalapeno burger! Wow
• Red Arrow Roadhouse – A Harbor Country classic: comfort food, casual drinks, and a “this-is-what-weekends-are-for” atmosphere.
• PostBoy – A newer-school, creative spot (Union Pier area) with modern vibes that feels like a Chicago neighborhood restaurant dropped into the woods.
• Flagship Specialty Foods & Fish Market – Gourmet market plus prepared foods; perfect for stocking the lake house with serious seafood and upscale provisions.
• Union Pier Social – Cocktails, small plates, and a social atmosphere, ideal for meeting friends or entertaining guests staying the weekend.
• Oaks Eatery – A go-to for breakfast/brunch and everyday comfort food within a short drive.

Stack on top of that the broader New Buffalo, Sawyer, and Three Oaks restaurant, winery, and brewery circuit, and you get a lifestyle package that feels much bigger than Lakeside’s population number.

What This Market Means for Sellers

If you own in Lakeside, here’s the reality:

• You are in a constrained-supply, high-demand niche.
  With typical home values up year over year and a median sale price over $1M in 49116, you’re sitting in one of the more premium corners of Southwest Michigan.
• The data looks “not very competitive,” but that’s misleading.
  Redfin labels 49116 as “not very competitive” because homes often sell a few percent below list and take about 61 days to go under contract.
  In a tiny luxury market, that often means the buyer pool is small but serious—and mispricing by even 5–10% can push you into a much longer days-on-market scenario.
• Positioning matters more than ever.
  With high price points and relatively few sales, buyers evaluate every detail: beach access, privacy, design, rental potential, and year-round usability.

How Team Popp approaches Lakeside listings:

• Scott brings the numbers, contracts, and risk management, making sure pricing is aligned with the micro-data, not just county-wide stats.
• Carlos drives the marketing machine—storytelling your property with photography, video, and digital campaigns tuned to where your buyers actually live (hello, Chicago and the North Shore).
• Together, under Live Lake Michigan, we position your home as one of the few tickets into a very limited club.

What This Market Means for Buyers

If you’re looking to buy in Lakeside:

• Expect low inventory and short lists.
  You might only see a handful of properties that fit your criteria each year. When the right one shows up, you need to be ready.
• Don’t over-interpret one month of data.
  With so few closings, one big lakefront sale or one smaller off-water cottage can swing the median. The real story is multi-year: consistent demand, gradually rising values, and very limited supply.
• There’s value beyond direct lakefront.
  Walkable and bikeable locations with strong beach access and renovated cottages can offer better price-to-lifestyle ratios while still delivering the Lakeside experience.

How we help buyers:

• Scott breaks down fair value based on actual local comps and micro-trends—not just automated estimates.
• Carlos stays on top of opportunities, pre-markets, and off-MLS conversations that matter in a relationship-driven market like Lakeside.

The goal? Get you into the right property at the right number, with a clear long-term strategy—personal enjoyment, future resale, and possible rental positioning.

Final Word from Team Popp – Live Lake Michigan in Lakeside

Lakeside, Michigan is not a volume market; it’s a scarcity market with:

• Strong second-home and luxury demand
• Limited inventory
• A genuine, tight-knit community
• Real lifestyle depth in dining, recreation, and proximity to Chicago

If you’re considering selling, we’ll help you time the market, price correctly, and present your home so it stands out in a small but powerful luxury segment.

If you’re considering buying, we’ll help you navigate a low-inventory environment, move quickly on the right opportunities, and build a plan so your Lakeside purchase is both a lifestyle win and a smart asset.

Carlos & Scott – Team Popp
Live Lake Michigan