Both have year-round temperate climes, glorious beaches, and a hot luxury market. However, the coastal paradises of San Diego and the Florida Keys, nestled on opposite shores, tell different stories.
“Beyond the warm climate and sought-after beaches, both carry deep Native American histories, and both saw Spanish contact in the 1500s,” writes Realtor.com® senior economist Anthony Smith in his latest luxury report spotlighting San Diego County and the Florida Keys, including Key West and the rest of Monroe County.
“Over the years, each has drawn buyers willing to pay for permanent access to the water, and today, both sit well above the national luxury threshold,” says Smith.
This two-bedroom condo in the Coronado section of the San Diego metro area is listed for $3,850,000.Damian Diaz
A decade ago, San Diego was the pricier coastal town. Today, that has reversed. While both metros’ entry-level luxury threshold (the top 10% of sales) soars above the nationwide benchmark of $1,250,459, the Keys is significantly outpacing San Diego.
The top 10% threshold in the Keys stands at $4,525,000, roughly 262% above the national level. Meanwhile, San Diego comes in at at $2,768,201, about 121% above.
When it comes to the top 5% (high-end luxury) and top 1% (ultraluxury) of sales, the gap is even wider: The Keys’ high-end threshold is $7,119,000, while its ultraluxury is a whopping $23,572,583. Meanwhile, San Diego’s two highest-priced tiers come in at $4,404,476 and $9,999,055, respectively.
The market size carries a lot of weight here. San Diego’s 5,800 active listings puts roughly 580 homes above its 90th percentile, while the Keys’ 1,280 listings puts only about 130 above the same threshold.
“Large metros hold a deep base of moderately priced inventory that pulls the line lower,” explains Smith. “Key West micropolitan has almost none.”
More than half of the Keys’ active listings, 55.9%, are already above the $1 million price point, compared to 42.9% in San Diego and only 13.2% nationally.
Another issue is scarcity. While both places are running out of room, especially oceanfront land, the Keys’ sits within Florida’s “Area of Critical State Concern.”
According to Florida Commerce, this is a program within designated geographic areas that would protect them from uncontrolled development that would “cause substantial deterioration of [their] resources.”
This 1974-built condo complex in Coronado commands a premium due to its proximity to the ocean.Damian Diaz
New residential construction is rationed in the Keys through a permit allocation system tied to maintaining a 24-hour hurricane evacuation time, says the report. Since new builds are severely restricted, this pushes prices even higher upward.
While both metros, like much of the country, saw massive gains during the COVID-19 pandemic era, San Diego has since given back nearly 30% of those gains, which peaked in July 2023. The Keys’ peak came much later—January 2026—but the market has since given back only 14.5% of that.
“Although the Keys’ smaller size means somewhat more volatile pricing trends than in San Diego, the floor of the Keys’ threshold still sits above every monthly reading San Diego has posted in the past decade,” concludes Smith.
The San Diego luxury market
While Rancho Santa Fe, in the northeast of San Diego County, carries the highest median list price at $6,889,750, it is Coronado, a thin barrier island to the southwest, that has the highest median price per square foot at $1,721.
Both ZIP codes essentially have no listings priced below $1 million—with Rancho Santa Fe at 100% in terms of listings over that price point, and Coronado at 98%.
“I don’t think I’ve ever sold anything below $1 million,” Whitney Benzian of Douglas Elliman – San Diego, who also grew up on the island, tells Realtor.com. “Or even $2 million.”
“The main thing about Coronado is how small it is,” he says. “That scarcity drives the real estate prices.”
Sweeping views of the Pacific will never go out of style, and scarcity is driving the Coronado market, says local agent Whitney Benzian.Damian Diaz
Beyond the scarcity of properties, Benzian points to a huge advantage for the area: The flat peninsula is very walkable, something that lures in buyers from all over.
“You don’t ever have to get in your car,” he says. “You can walk everywhere or ride your bikes. Most people these days have golf carts. You can go weeks and never leave Coronado.”
Coronado’s public beach, its bay with public and private marinas, its wraparound bike path, plethora of retail, and new restaurants such as By the Sea and Night Hawk (in the Baby Grand Hotel) mean there’s really no reason to leave.
A popular attraction is the Hotel del Coronado, built in 1888 and named a National Historic Landmark. The area is also dotted with historic Victorian and Craftsman homes, many of which are snapped up and renovated, then given steep tax breaks in return.
Benzian says the peninsula has high-quality schools, and parents appreciate that kids can walk or bike around on their own.
“You don’t have to schlep your kids to the soccer or baseball fields,” he says. “It leaves you with so much more free time.”
There’s also an affordable public golf course, tennis courts, and the public Coronado Beach on the Pacific, with Point Loma to the north and Mexico to the south. Being on the beach means a constant breeze that draws those who want to flee the heat of Texas, Nevada, Arizona, and Mexico, says the agent.
“Right now, I think it’s the hottest we’ve experienced, and it’s like 80 degrees,” he says. “The breeze is constant. We have the classic Mediterranean climate.”
If you want nightlife, entertainment, or a Padres game, a trip over a 2-mile bridge (also bike-friendly) will bring you to downtown San Diego.
According to Realtor.com data, Los Angeles accounts for 29.3% of San Diego’s cross-market listing views. While the agent says he does see buyers coming in from L.A. and San Diego proper, he doesn’t view it as being a significant number.
“To the extent that one can live in Coronado, people certainly want to,” he says.
The most in-demand properties? A well-positioned lot where someone can build a dream home. An empty 10,000-square-foot lot or teardown can easily fetch $4 million or more, he says.
“The secret is out,” he says of Coronado.
But he admits prices have softened from pandemic-era peaks.
“The buyer is becoming more discerning,” he says. “There’s this battle between the buyer and seller. The seller still thinks they can have these really aspirational prices—and they can’t.
“The buyers are high net worth, but they don’t just spend for the sake of spending.”
Despite all that, the broker still thinks that Coronado is a bit undervalued.
“There’s room for continued growth,” he says.
Jenna Hoyas at Douglas Elliman in San Diego says that at the ultraluxury level, with an entry of $10 million, the buyer pool is primarily domestic, a mix of entrepreneurs, business owners, executives, tech and finance professionals.
“At this level [buyers] aren’t necessarily buying because they need to be close to an office,” she says. “They are buying for the lifestyle. They want privacy, views, space, beautiful architecture and proximity to the ocean, and they are willing to pay a premium for a property that gives them all of that.”
The Florida Keys
The famous archipelago south of Miami is 120 miles of island paradise stretching between the Atlantic Ocean and Gulf of Mexico, from mainland Florida toward Cuba, and threaded together by the Overseas Highway.
There are five distinctive regions: Key Largo, Islamorada, Marathon, Big Pine and the Lower Keys, and Key West.
Islamorada is the priciest isle in both median list price and the price per square, at $2,667,500 and $1,163, respectively. It also has the highest share of homes priced above $1 million at 71.1%.
Summerland Key follows with a median list price of $1,299,250; then Key West at $1,211,000; Key Largo at $1,200,000; and Marathon at $1,097,000. All of the islands have more homes over $1 million than not, with Marathon having the lowest share at 51.7%.
Key Largo has the lowest price per square foot ($706) and is the closest to Miami.
“The trip takes about an hour, whether driving or boating, making it very convenient for my clients who want the best of both worlds,” Angel Nicolas at Serhant tells Realtor.com.
The Nicolas Team sold an Islamorada compound to Barstool Sports President David Portnoy for $27.8 million, setting a record for the Keys.
The sale price is 12 times the price it was last sold for in 2019, according to Realtor.com property data.
The eight-bedroom, 9.5-bath, 10,228-square-foot manse at Overseas Highway on a 1.65-acre lot was originally listed for $31.2 million.
Nicolas notes the private Ocean Reef Club, located on the northern tip of the Key Largo, as a major attraction to the area.
He says most buyers are second-home purchasers or retirees—people who love to boat and fish—with the majority coming from Palm Beach or Delray, and some migrating from California.
Key Largo also offers larger dwellings than some of the other islands—it’s median square footage is 1,632, just behind Islamorada—but Nicolas says it is all about the larger lot sizes.
“The homes … can sometimes be smaller, but they are typically set on larger waterfront lots and often include a guesthouse,” he says.
Prime luxury: Islamorada
“It’s like being in the Bahamas, but you’re in the U.S.,” Michael E. Petrusha of Find Florida Keys Homes tells Realtor.com. “If you want nice weather, the world’s best fishing, the best views, best diving, you want all the things the Caribbean offers, but you don’t want the hassle of going out of the country, then you come to the Upper Keys.”
Michael and his wife, Tracey, have been selling Upper Keys properties for a quarter-century, and have raised four children there. They also represented the sellers of Little Conch Key, a tiny 5-acre private island off Marathon once owned by Walt Disney, getting $13 million.
“We call it the Hamptons of the Keys,” he says of Islamorada, which has the highest median price point in the Keys by far at $2.66 million.
Petrusha, also a local lender, notes that the Upper Keys—closer to Miami and Broward County than the Lower—is more convenient to primary homes, offices, and larger hospitals.
Islamorada offers a bit more distance from all of that than Key Largo does, combined with a more village feel, full of artists and boutiques, restaurants, and clubs like the famous Cheeca Lodge and Spa.
“It’s tough to get off the rock,” Petrusha says of any of the islands lower than Islamorada.
He and his wife currently represent a $7 million listing with a rare 225 feet of prime waterfront and access to both Florida Bay and the Atlantic Ocean. The seven-bedroom estate comes with a deep-water canal that can park a megayacht.
They also represent a 61-acre island about 7 miles off Key West currently lowered to $495,000, which is less than the typical New York City studio apartment.
Islamorada also offers a quieter, more relaxed vibe than Key West, which Petrusha calls the “New Orleans of the Keys.”
“You could step outside your house, and there’s somebody drinking a beer,” he says with a laugh. “It’s very city-ish there.”
Since Portnoy bought his $27.8 million compound in late 2025, the couple say they have noticed a shift in buyers—with more big shots circling sprawling compounds.
“Islamorada is very upscale,” says Tracey. “A lot of mom and pop shops that cater to the upscale crowd.”
Several big buyouts—including Cheeca Lodge and Spa, bought by Bass Pro Shops in June for an undisclosed sum—means major equity is pouring into the little island.
Adds Petrusha: “You definitely got corporations that are acquiring a lot and making it more difficult to live if you’re local.”
$1,395,000 : 709 Olivia Street Key West, FL 33040
| 2 bed | 4 bath | 2,200 sq ft |
NEW LISTING IN OLD TOWN WITH OFF STREET PARKING! This Old Town investment property comes fully furnished so you can move right in or start renting immediately. It is a legal duplex with two units, each having one bedroom and one and a half bathrooms but could easily be converted to a single family home.
Call me for buyer agent representation: Lawrence Herstel 
Bascom Grooms Real Estate 218 393 1550
Located on a fenced corner lot in Old Town, it’s just blocks from Duval Street, making it very convenient for dining, shopping, nightlife and enjoying the Key West sights The home has updated kitchen and baths, ductless AC units, hardwood floors, vaulted ceilings, and skylights. It’s a perfect mix of modern style and classic Keys architecture. Live in one unit and rent out the other, have a dedicated private guest space, or use both to generate income. Each unit has its own private outdoor area and laundry. There is a welcoming front porch perfect for morning coffee. Desired X Flood Zone!
See the available homes for sale in your area! Get home values, and learn about the local schools! Your Luxury waterfront Key West dream home awaits you!
I truly enjoy the experience of helping people list their Key West home or condo.
My knowledge of the real estate business and expertise in negotiating the transaction ensure that my sellers will get the most amount of money in their sale.
Communication with all parties involved in the sale is paramount. This enables me to quickly follow through and handle any issues that may arise in a real estate transaction.
Allow me the privilege of listing your home today!
Lawrence Herstel
(218) 393 1550
See the available homes for sale in your area! Get home values, and learn about the local schools! Your Luxury waterfront Key West dream home awaits you!
I truly enjoy the experience of helping people list their Key West home or condo.
My knowledge of the real estate business and expertise in negotiating the transaction ensure that my sellers will get the most amount of money in their sale.
Communication with all parties involved in the sale is paramount. This enables me to quickly follow through and handle any issues that may arise in a real estate transaction.
Allow me the privilege of listing your home today!
Lawrence Herstel
(218) 393 1550
See the available homes for sale in your area! Get home values, and learn about the local schools! Your Luxury waterfront Key West dream home awaits you!
I truly enjoy the experience of helping people list their Key West home or condo.
My knowledge of the real estate business and expertise in negotiating the transaction ensure that my sellers will get the most amount of money in their sale.
Communication with all parties involved in the sale is paramount. This enables me to quickly follow through and handle any issues that may arise in a real estate transaction.
Allow me the privilege of listing your home today!
Lawrence Herstel
(218) 393 1550
DUPLEX! Discover the breathtaking corner property at Sunrise Shores, set on an expansive lot exceeding 13,000 square feet. POOL! The main residence offers over 1,750 square feet of living space, complemented by a detached guest cottage of 640 square feet. This meticulously maintained property has been cherished by its owners.
The main home features three bedrooms and two bathrooms. It boasts a thoughtfully designed layout that includes a spacious family room and a large living room with a fireplace that opens up to the lanai. The primary bedroom provides direct access to the pool area and features an updated bathroom and a generous walk-in closet. The second bedroom also opens to the pool area, while the third bedroom is conveniently located next to the updated hall bath.
There is also a laundry room with additional storage space.
The detached guest cottage includes one bedroom and one bathroom. This property is perfect for owner-occupiers, investors, multi-generational living, and more.
Status
For Sale
Association no
Directions Flagler Ave to Venetian Drive, LEFT on Airport Dr, and LEFT on Jamaica
Waterfront yes
Waterfront Type Canal Front
WaterviewCanal View
Interior
Appliances Washer, Dryer, Dishwasher, Refrigerator, Range, Oven, Microwave, Stainless Steel Appliance(s)
Cooling Type Central Air, Ceiling Fans(s), Ductless
Flooring Tile
Furnished Furnished
Interior Features Built-in Cabinets, Granite Counter Top, Storage, Walk-in Closet(s)
Interior Features Split Bedroom, Built-in Cabinets, Granite Counter Top, Storage, Walk-in Closet(s)
Attached Garage no
Construction Materials CBS, Frame, Combo Construction
Exterior Features Chickee Hut, Rain Gutters, Hot Tub, Shed, Storage
Location – KW Neighborhood New Town
Lot Size Area 0.12
Lot Size Dimensions 56 X 100
Lot Size Square Feet 5600
Parking Features Open
Patio And Porch Features Open Porch/Balcony, Patio
Pool Features In Ground, Salt Water
Pool Info – Other Chiller
Pool Private yes
Roof Metal Roof
Utilities FKAA, Municipal Sewer
Windows Doors Impact Rstnce Doors
Financial
Association Fee IncludesNone
Tax Annual Amount 10598.59
Tax Year 2025
Vehicle Storage Open Parking
Additional
Contract Information – As is Right to Inspect Yes
Mls StatusActive
Pets Allowed Yes
Seawall Concrete
Shutters Panel
See the available homes for sale in your area! Get home values, and learn about the local schools! Your Luxury waterfront Key West dream home awaits you!
I truly enjoy the experience of helping people list their Key West home or condo.
My knowledge of the real estate business and expertise in negotiating the transaction ensure that my sellers will get the most amount of money in their sale.
Communication with all parties involved in the sale is paramount. This enables me to quickly follow through and handle any issues that may arise in a real estate transaction.
Allow me the privilege of listing your home today!
Lawrence Herstel
(218) 393 1550
$1,975,000 : 1620 Jamaica Drive Key West, FL 33040
| 4 bed | 3 bath | 2,080 sq ft |
Acres 0.12
County Monroe
Subdivision Riviera Shr Amd Plat (3.0)
Year Built 1970
Key West WATERFRONT Home with a POOL! This expansive two-story residence has everything you need, featuring a first-floor primary suite, ample off-street parking, and a canal for boating enthusiasts, along with a fantastic pool area complete with a tiki hut for shaded relaxation.
With 4 bedrooms and 3 bathrooms, this home spans 2,080 sq. ft. and is just minutes away from Old Town Key West.Nestled on a cul-de-sac, Jamaica Drive is the perfect island oasis–simply drop your paddleboard in from your backyard! The kitchen is chef-ready, offering plenty of cabinet space and a large island.
The open floor plan is designed for entertaining, seamlessly flowing to the backyard area with tiki hut, canal views, and a beautiful swimming pool. The first floor includes a primary suite with a luxurious bath, walk-in closet, and pool access. There are three spacious bedrooms located on the second floor.
Additional features include central AC, ductless units, a workshop, soundproof windows, impact-rated doors, and hurricane panels. Saltwater pool with chiller and heater. Perfect canal home with seawall without leaving KW!
Association no
Directions Flagler Ave to Venetian Drive, LEFT on Airport Dr, and LEFT on Jamaica
Waterfront yes
Waterfront Type Canal Front
WaterviewCanal View
Interior
Appliances Washer, Dryer, Dishwasher, Refrigerator, Range, Oven, Microwave, Stainless Steel Appliance(s)
Cooling Type Central Air, Ceiling Fans(s), Ductless
Flooring Tile
Furnished Furnished
Interior Features Built-in Cabinets, Granite Counter Top, Storage, Walk-in Closet(s)
Interior Features Split Bedroom, Built-in Cabinets, Granite Counter Top, Storage, Walk-in Closet(s)
Attached Garage no
Construction Materials CBS, Frame, Combo Construction
Exterior Features Chickee Hut, Rain Gutters, Hot Tub, Shed, Storage
Location – KW Neighborhood New Town
Lot Size Area 0.12
Lot Size Dimensions 56 X 100
Lot Size Square Feet 5600
Parking Features Open
Patio And Porch Features Open Porch/Balcony, Patio
Pool Features In Ground, Salt Water
Pool Info – Other Chiller
Pool Private yes
Roof Metal Roof
Utilities FKAA, Municipal Sewer
Windows Doors Impact Rstnce Doors
Financial
Association Fee IncludesNone
Tax Annual Amount 10598.59
Tax Year 2025
Vehicle Storage Open Parking
Additional
Contract Information – As is Right to Inspect Yes
Mls StatusActive
Pets Allowed Yes
Seawall Concrete
Shutters Panel
See the available homes for sale in your area! Get home values, and learn about the local schools! Your Luxury waterfront Key West dream home awaits you!
I truly enjoy the experience of helping people list their Key West home or condo.
My knowledge of the real estate business and expertise in negotiating the transaction ensure that my sellers will get the most amount of money in their sale.
Communication with all parties involved in the sale is paramount. This enables me to quickly follow through and handle any issues that may arise in a real estate transaction.
Allow me the privilege of listing your home today!
Lawrence Herstel
(218) 393 1550
$9,888,000 : 1430 Vernon Ave Key West, FL 33040
| 3 bed | 2 bath | 2,071 sq ft |
Fabulous Find on the Atlantic Side of Key West! Welcome to a truly unique opportunity in the heart of Key West. As the last and only remaining undeveloped property in the Historic Commercial Tourist District (HCT zone), this listing presents a rare and final chance to create something extraordinary. Imagine waking up to breathtaking, unobstructed ocean and beach views every day!
Seabirds passing overhead, gentle breezes arriving at your lanai–it’s an experience like nowhere else. This is island living at its finest! Permitted HCT uses include: Single-family and two-family residential dwellings, Multiple-family residential dwellings, Restaurant, Business and professional offices, Hotels, Motels, transient lodging, and more. This two-story home comes equipped with two separate electric meters.
This exceptional property is truly one of a kind, with no identical or closely similar listings anywhere in Key West. The ideal circumstances are here and now– an unparalleled combination of an oversized ocean-view lot, located just three blocks from Duval Street, the gateway to downtown. Spanning 8,700 square feet, this property offers ample space for your creative vision, whether you dream of building a luxurious residence, alongside a commercial venture boutique hotel, or restaurant, — this and more are supported by HCT zoning. This property is all about the excitement of shaping a new vision for a future in paradise.
Let your imagination run wild and transform this blank canvas into something extraordinary. Don’t miss out on this once-in-lifetime opportunity–call today for your private tour and start envisioning your future in Key West!
See the available homes for sale in your area! Get home values, and learn about the local schools! Your Luxury waterfront Key West dream home awaits you!
I truly enjoy the experience of helping people list their Key West home or condo.
My knowledge of the real estate business and expertise in negotiating the transaction ensure that my sellers will get the most amount of money in their sale.
Communication with all parties involved in the sale is paramount. This enables me to quickly follow through and handle any issues that may arise in a real estate transaction.
Allow me the privilege of listing your home today!
Lawrence Herstel
(218) 393 1550
$12,500,000 : 332 Sunset Key Dr, Key West, FL 33040
| 6 bed | 7 bath | 3.635 sq ft |
A distinguished offering on one of Key West’s most coveted private island enclaves, 32 Sunset Key Drive embodies the ease, elegance, and exclusivity of waterfront living.
One of the largest custom residences on Sunset Key, this 3,635-square-foot oceanfront estate was conceived by its original owners with an unwavering commitment to craftsmanship, comfort, and detail. Set beside its own private beach, the home features six ensuite bedrooms and seven full baths, creating a refined retreat designed for gracious hosting and effortless relaxation.
Inside, coffered wood-paneled ceilings, tumbled marble, and solid oak floors lend depth, texture, and timeless coastal sophistication. Expansive living, dining, and kitchen spaces open naturally to the outdoors, blurring the line between interior comfort and the island’s spectacular waterfront setting. Beyond, a custom rock pool with a hot tub and two-story slide evokes the atmosphere of a private resort, while a fully equipped outdoor kitchen, full bath, shower, and laundry facility elevate every gathering with ease and intention.
Hop on the five minute ferry ride to your island paradise, enjoy the fabulous spa and dine at the acclaimed restaurant Latitudes. Truly, this is a one of a kind opportunity for the discerning buyer.
See the available homes for sale in your area! Get home values, and learn about the local schools! Your Luxury waterfront Key West dream home awaits you!
I truly enjoy the experience of helping people list their Key West home or condo.
My knowledge of the real estate business and expertise in negotiating the transaction ensure that my sellers will get the most amount of money in their sale.
Communication with all parties involved in the sale is paramount. This enables me to quickly follow through and handle any issues that may arise in a real estate transaction.
Allow me the privilege of listing your home today!
Lawrence Herstel
(218) 393 1550
$3,600,000 : 119 Simonton St, Key West, FL 33040
| 4 bed | 4 bath | 2,691 sq ft |
Discover modern island luxury at 119 Simonton Street, a premier end-unit townhouse nestled within the exclusive gated community of Old Town Villas. Built in 2018 and spanning a generous 2,691 square feet, this residence seamlessly blends sophisticated contemporary design with the timeless allure of Key West.
The interior features new white oak flooring that leads you through an open-concept living space. The kitchen is a true standout, boasting elegant granite countertops and a custom kitchen island–a unique feature in the community. For the ultimate convenience, a private elevator services all four floors of the home, transporting you from the air-conditioned two-car garage to the spectacular rooftop terrace where you can view daily sunrises over the Historic Key West Marina and sunsets over Mallory Square, both a very short walk away. The top floor features a rare full bathroom and a flexible bonus room ideal for a home office or guest suite. Whether you’re mixing drinks at the custom wet bar or lounging on the terrace, this level serves as the ultimate private retreat for taking in breathtaking panoramic views.
Peace of mind is built into the architecture with full impact-rated windows and doors and a durable metal roof, ensuring the home is as secure as it is beautiful. The third floor has two primary bedrooms featuring large walk-in closets and balconies. The lifestyle offered here is unparalleled, situated just one block off the vibrant energy of Duval Street. You are steps away from the island’s best dining and boutiques, yet you can retreat instantly to the quiet security of a gated community. Spend your afternoons lounging by the large tropical community pool and cabana area, enjoying a level of comfort and convenience unsurpassed in the heart of Old Town. With a rare two-car garage and an unbeatable location, this residence captures the very best of the Florida Keys lifestyle.
