Buying

What Should Buyers Know About Key West by the Sea Condos?

Scott Forman

October 7, 2026 · 7 min read

Key West by the Sea at 2601 South Roosevelt Boulevard, from a former Scott Forman listing

Key West by the Sea · Current MLS

4

Active

$599K–$935K

Price range

$844K

Median ask

60-day min.

Rental rule

Rental rule applies after the first year of ownership; verify current association documents. Market data refreshes periodically. Viewed Oct 7, 2026.

Key West by the Sea is one of those properties that makes more sense once you understand what it actually is. It sits directly across from Smathers Beach, has unusually substantial concrete construction, large landscaped grounds, two pools and tennis courts, and it feels far more residential than a typical vacation-oriented condo complex.

I know it well. I spent the first seven years of my real-estate career as the on-site agent at Key West by the Sea, and I have listed and sold units in the community over the years. That history matters because the differences from one building, floor and unit to another are real.

A little history

Key West by the Sea is a 206-unit gated condominium community at 2601 South Roosevelt Boulevard.

The association dates to the 1970s, while the residential buildings themselves were built in the mid-1960s. Local Key West historical accounts identify the buildings as former Navy officers' housing or barracks before their condominium use.

That background fits the way the property feels. These are not lightweight frame buildings. The complex has a heavy, institutional construction style that is very different from many smaller residential buildings around Key West.

The grounds are another part of the story. The community sits on roughly eight landscaped acres with two swimming pools, tennis courts, a clubhouse, shuffleboard and substantial open space between the buildings.

And directly across South Roosevelt Boulevard is Smathers Beach.

The construction is one of the things I like most about it

The buildings are concrete and CBS construction, and older records describe poured-concrete construction. They have an almost bunker-like solidity to them.

Many units have also been upgraded with impact-rated, sound-insulated windows and doors, including improvements made through the Key West International Airport noise-insulation program.

That combination matters in Key West.

I would never call any building hurricane-proof. But when a hurricane threatens the island, I have always considered Key West by the Sea one of the more substantial residential structures in town because of the heavy concrete construction and the impact-rated openings found in many units.

Those upgrades also make a noticeable difference day to day. The airport is nearby, and the sound-insulated windows and doors dramatically reduce outside noise in participating units.

A buyer should still verify the exact windows and doors serving the unit, review current association insurance, and read the latest engineering and inspection information. But the basic construction is a genuine strength of the property.

What is it like to live there?

The biggest advantage is the combination of beach access, open space and amenities.

You can walk across the street to Smathers Beach. The South Roosevelt promenade gives you a long stretch for walking, running or biking. Inside the gates, the community has two pools, tennis courts and large landscaped areas.

The experience changes depending on the building and floor.

Some units face the Atlantic and can have excellent ocean views. Others look over the pools, courtyards or tropical grounds. A sixth-floor ocean-facing unit is a completely different property from a first-floor garden unit, even when the square footage is similar.

That is why I would never value the complex with one blanket price-per-square-foot number.

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Current Key West by the Sea Listings

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Florida Keys MLS · Information deemed reliable but not guaranteed. Prices and availability may change.

What are the rental rules?

This is an important one.

Key West by the Sea is not a transient-rental community. The longstanding rental rule reflected in my own prior MLS listings, as well as current and recent MLS records, is:

  • A new owner cannot rent the unit during the first 12 months of ownership.
  • After that first year, rentals are permitted in 60-day minimum increments.

That rule is one reason the property has maintained a more residential feel than many vacation-oriented properties.

Because condominium rules can be amended, I would still require the current declaration and association rules before a buyer relies on the rental policy. But if your plan is weekly or nightly vacation rental income, this is not the community I would point you toward.

If your plan is personal use, seasonal use, or longer-term rentals after the first year, it can make much more sense.

What do the condo fees cover?

The amount varies by unit size and configuration.

Current and recent MLS listings show monthly fees that can include building insurance, common-area and grounds maintenance, cable or Wi-Fi, security and other association expenses.

The number by itself is not enough.

I want to know what the fee covers, how reserves are funded, whether there are current or proposed special assessments, what insurance is carried by the association, and what remains the unit owner's responsibility.

That is especially important in an older concrete condominium community. Strong construction does not eliminate maintenance. Concrete restoration, roofs, elevators, windows, mechanical systems, insurance and reserves all matter.

What should you look at before buying?

For me, the unit and the association have to be evaluated together.

On the unit itself, I would look closely at the floor, view, condition, renovation quality, windows and doors, air-conditioning system, parking, storage and any work that may have been done over the years.

Then I would review the association package, including:

  • Current budget and financial statements.
  • Regular and special assessments.
  • Reserve funding.
  • Insurance.
  • Meeting minutes.
  • Applicable inspection and reserve-study materials.
  • Rental rules.
  • Pet, parking and renovation rules.
  • Maintenance responsibilities between the association and the unit owner.

I also want to know exactly what a buyer is purchasing. Parking may be open or assigned depending on the current rules. Storage varies. Views vary dramatically. Some units have been combined or reconfigured. Those details affect both value and resale.

Is Smathers Beach part of the property?

No. Smathers Beach is a public City of Key West beach.

Key West by the Sea's advantage is its location directly across South Roosevelt Boulevard from the beach. Buyers should not confuse that proximity with private beach ownership.

Some units have direct Atlantic views. Others do not. The exact building, floor and orientation matter.

What does the market look like inside the complex?

There are usually meaningful differences in value between the one-, two- and three-bedroom layouts, and between garden, pool and ocean-facing units.

Recent sales have ranged widely depending on size, floor, condition and view. That is normal for this property.

When I value a Key West by the Sea unit, I start inside the complex before I look elsewhere. A sale in the same building with a similar floor plan and view is usually much more useful than a citywide condo average.

You can see current Key West condominium pricing in my Key West condo market guide, but for a specific Key West by the Sea unit, the internal comps are what matter most.

Frequently asked questions

How many units are at Key West by the Sea?

The association identifies Key West by the Sea as a 206-unit condominium community at 2601 South Roosevelt Boulevard.

Are rentals allowed?

Yes, with restrictions. The longstanding rule reflected in my own historical MLS listings and current/recent MLS records is no rentals during the first 12 months of ownership, followed by a 60-day minimum rental term. Buyers should confirm the current association documents before relying on it.

Does the community have pools and tennis courts?

Yes. The community has two swimming pools and tennis courts, along with a clubhouse and landscaped common areas.

Is Smathers Beach private?

No. Smathers Beach is public. The advantage is that Key West by the Sea sits directly across South Roosevelt Boulevard from it.

Are the buildings concrete?

Yes. MLS records repeatedly identify the buildings as concrete or CBS construction, with older records also describing poured-concrete construction. Many units also have impact-rated, sound-insulated windows and doors.

My take on Key West by the Sea

Key West by the Sea is not the newest condominium community in Key West, and it is not trying to be.

Its strengths are different: substantial construction, large grounds, two pools, tennis, direct proximity to Smathers Beach, and a rental structure that keeps the property more residential.

Having spent the first seven years of my career there, I know the complex well enough to say that the right unit can be a very good fit for someone who values those things.

The key is buying the right unit at the right price and understanding the association documents before you commit.

If you are considering a unit at Key West by the Sea, contact Royal Palms Realty. I can help you compare the current listings, recent sales, building positions, views and the documents that matter before you make an offer.

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