Million: Three Islands, Three Lifestyles
One million dollars. It's a significant milestone in any real estate market, but on Florida's Gulf Coast, that same dollar amount can buy dramatically different experiences depending on which island you choose.
I've helped clients find their dream homes on all three of our most coveted destinations—Longboat Key, Siesta Key, and Anna Maria Island. Here's the honest breakdown of what million actually gets you in each location.
Longboat Key: The Prestige Factor
At million on Longboat Key, you're typically looking at:
- Property type: Condominium or townhouse (rarely a single-family home)
- Square footage: 1,200 to 1,800 square feet
- Location: Bay view or indirect Gulf view (direct Gulf front is typically M+)
- Bedrooms: 2-3 bedrooms
- HOA fees: ,000-,500/month (includes building maintenance, insurance, amenities)
What Makes Longboat Special
Longboat Key is the most exclusive of the three islands. It's known for world-class golf courses, prestigious country clubs, and a more subdued, sophisticated atmosphere. At the M price point, you're buying into a lifestyle—quiet mornings, manicured landscapes, and neighbors who value privacy.
The tradeoff? Less walkability. Most Longboat properties require a car to reach restaurants and shops. But if you're seeking a resort-style community with top-tier amenities, Longboat delivers.
Siesta Key: The Beach Paradise
At million on Siesta Key, buyers typically find:
- Property type: Condominium or villa (single-family homes start around .3M)
- Square footage: 1,400 to 2,000 square feet
- Location: Gulf view or beach proximity (direct beachfront condos at upper end of budget)
- Bedrooms: 2-3 bedrooms
- HOA fees: 00-,000/month
What Makes Siesta Key Special
Siesta Key is all about the beach. The iconic Siesta Beach—award-winning powder-white sand—draws visitors from around the world. At M, you can often find a condo within walking distance (or even steps from) the beach.
The village area offers excellent walkability with restaurants, shops, and entertainment. The tradeoff is that Siesta can get crowded during season (November through April), and condo complexes may have more turnover with vacation rentals.
Anna Maria Island: The Charming Underdog
At million on Anna Maria Island, buyers typically find:
- Property type: Single-family home (more common) or townhouse
- Square footage: 1,400 to 2,200 square feet
- Location: Near beach or bay access (direct beachfront at upper end)
- Bedrooms: 3-4 bedrooms
- HOA fees: /bin/bash-00/month (many single-family homes have no HOA)
What Makes AMI Special
Anna Maria Island offers the most Florida feel of the three. With its historic cottages, golf cart-friendly streets, and small-town charm, AMI appeals to buyers seeking an authentic island experience. At M, you're more likely to find a single-family home—often with a garage, private backyard, and no HOA restrictions.
The tradeoff? Homes tend to be older (1960s-1980s construction), and inventory is limited. The island's strict building codes preserve its charm but also mean newer construction is rare.
Head-to-Head Comparison
| Feature | Longboat Key | Siesta Key | Anna Maria Island |
|---|---|---|---|
| Property Type at M | Condo/Townhouse | Condo/Villa | Single-Family Home |
| Average Size | 1,200-1,800 sq ft | 1,400-2,000 sq ft | 1,400-2,200 sq ft |
| HOA Range | ,000-,500/mo | 00-,000/mo | /bin/bash-00/mo |
| Walkability | Low | High (Village) | High (entire island) |
| Beach Access | Condo complex | Beachfront or nearby | Varies widely |
| Age of Homes | 1980s-2000s | 1970s-2010s | 1950s-2000s |
| Vacation Rentals | Limited | Common | Common |
Lifestyle Considerations
Choose Longboat Key if:
- You want a prestigious, resort-style community
- Golf and country club amenities matter to you
- You prefer a more private, low-key atmosphere
- You're comfortable with higher HOA fees for maintenance-free living
Choose Siesta Key if:
- The beach is your top priority
- You want walkability to restaurants and shops
- You don't mind some seasonal crowds
- You want a condo with modern amenities
Choose Anna Maria Island if:
- You want a single-family home without HOA constraints
- Historic Florida charm appeals to you
- You want to get around by golf cart or bike
- You prefer a more authentic, less resort feel
The Hidden Costs
Beyond the purchase price, smart buyers consider ongoing costs:
- Property insurance: Florida coastal properties require windstorm insurance, which can range from ,000-0,000+ annually depending on location and construction
- Flood insurance: Required if you're in a flood zone (most waterfront properties are)—typically ,500-,000/year
- HOA fees: Can range from /bin/bash to ,500/month—always get the total cost in writing
- Property taxes: Florida has no state income tax but property taxes are based on assessed value; expect to pay roughly 1-1.5% of your home's value annually
Finding the right island is about matching your lifestyle aspirations with reality. What you prioritize—beach access, community, privacy, or walkability—will determine which million feels like the better investment for you.
Making Your Decision
Every buyer is unique, and the right choice depends on how you want to live. My advice? Spend time on each island before you buy. Visit in different seasons. Talk to locals. Experience the rhythm of each community.
Some buyers fall in love with Longboat's elegance. Others are drawn to Siesta's beach-centric lifestyle. Many find their home on AMI's charming streets. There's no wrong answer—only the answer that's right for you.
Want to explore options in your budget? Send me a message and let's find your perfect match.
I know these islands intimately—from the quiet bayside streets of Longboat to the bustling Village of Siesta to the eclectic neighborhoods of AMI. Let's discuss what matters most to you, and I'll help you discover which island feels like home.