We’ve always been a real estate-obsessed town. But this year, in the midst of lockdowns and uncertainty, our homes have become more important than ever. They are havens of comfort and safety, places where our restless do-it-yourself energy is finding an outlet and smart investments in this period of rock bottom mortgage rates. Here's our guide to the perfect neighborhood for you, a look at who’s buying in this red-hot real estate market and the top sales of the year.

Are you a newcomer to Florida, eager to meet new friends and explore new places? Do you crave the peace and quiet of the great outdoors? Is walking outside your door into the hustle and bustle of city life important to you? (Relatively, of course; New York City we aren’t.) Boater? Birder? Bicycler? Whatever your passion, take it from us, we guarantee you’ll find the neighborhood to follow it in the Sarasota-Manatee area. Here are 27 great neighborhoods to get you started.

Ohana, the Polynesian-inspired compound that sold for $11.4 million in 2019.

Ohana, the Polynesian-inspired compound that sold for $11.4 million in 2019.

Image: Ryan Gamma

For Island Seekers

Longboat Key

Traditionally a winter retreat for retired Midwestern CEOs, this barrier island boomed once younger one-percenters found they could conduct business anywhere from their laptop computers. Among recent head-turning sales, fashion designer Michael Kors caused a commotion in 2014 when he snapped up two big Gulf-front lots for $6 million for his vacation retreat. Ohana, a Polynesian-inspired family compound that had been on the market for six years, sold in 2019 for $11.4 million. And this summer, the $13 million plus $1 sale of a Gulf-front estate on the north end of the key broke Sarasota County’s all-time residential MLS sale record—by that dollar. Toward year’s end, the record will be broken when “Serenissima,” listed at $19.75 million, closes. Up next: The Residences at St. Regis, a 69-condo complex on the site of the late, beloved Colony Beach and Tennis Resort, pre-construction priced at $2 million to $10 million.  

Casey Key

The lush tropical nine-mile-long island, separated from the mainland by a historic swing bridge, has long been one of the region’s most exclusive enclaves, with wealthy homeowners who fly in and out of Venice Airport on their private jets. If you want to be author Stephen King’s neighbor, this is the place. Gulf-to-bay properties of an acre or more command the highest prices; a flurry of sales this summer were in the $1.5 million to $5.7 million range. Casey Key’s biggest sale in 10 years took place last December: $8.75 million for “Villa de Paradiso,” a gated Mediterranean estate with 200 feet of Gulf frontage. 

Siesta Key

Forget that infamous MTV “reality” show of the same name. Siesta Key is relaxed and family oriented, with a permanent vacation feel thanks to its lively Village restaurant scene and world-class beaches. (Siesta Beach was twice named the No. 1 beach in the U.S.) More eclectic and more affordable than the area’s other barrier islands, Siesta Key is often the place newcomers land when they move to Sarasota. Prices are all over the place, from a one-bedroom beachfront condo in the low $400,000s in the Palm Bay Club to a waterfront mansion on Flamingo Road that sold last fall for $10.5 million, the key’s second-highest sale ever.

City of Anna Maria

This little town at the northern tip of Anna Maria Island—full-time population 1,800—is beloved for its beachy ambiance, but it isn’t stuck in time. In the last decade, investors have snapped up many humble 1960s-era concrete-block residences and built multi-story mega vacation rental homes. Now, nearly 70 percent of homeowners are rental owners. That means a constant turnover of weeklong visitors, who bicycle to scenic Pine Avenue to shop, dine and amble to the city pier. All this charm comes at a cost: In 2018, the city made Zillow’s list of 24 U.S. cities whose median price is $1 million.

Waterside at Lakewood Ranch

Waterside at Lakewood Ranch

For the Snowbird

Esplanade Siesta Key

National homebuilder Taylor Morrison hit on a winning formula with its Esplanade  communities—Esplanade at Siesta Key (it’s on the mainland, FYI, off Siesta Key’s Stickney Point Bridge), on Palmer Ranch, at Artisan Lakes in Palmetto, and two in Lakewood Ranch: Esplanade Golf & Country Club and Esplanade at Azario. Together, they offer thousands of new homes. Like the many other active adult communities springing up around the region, they have big, bright clubhouses with resort-style pools, fitness centers and other amenities, even on-site activities directors, the better to allow newcomers to make new friends.

Waterside at Lakewood Ranch

So many neighborhoods in this city-sized master-planned community appeal to second homeowners, it’s hard to narrow down the best. One reason the Ranch’s newest village, Waterside, which broke ground in 2017 and will eventually have 5,144 homes, stands out is the Waterside Place village center. When completed, it will provide a place for residents to meet and mingle, with offices, shops, restaurants and an eight-acre park on a small island accessed by a pedestrian bridge. A farmers’ market and other community-building events are promised. And The Players Centre for Performing Arts will build its new theater complex here. 

Heritage Harbour

At 2,500 acres, this established master-planned community on the south shore of the Manatee River in east Bradenton is a golfer’s mecca, with the public 18-hole Heritage Harbour Golf Club and Stoneybrook Golf and Country Club; and the private, 27-hole River Strand Golf and Country Club. The community’s Central Park offers residents baseball diamonds, walking paths, a playground and lake pier. And did we mention the region’s second Costco opened here last year?

Renaissance at Wellen Park

Wellen Park, until this summer known as the West Villages, is sprouting rapidly in south Sarasota County; this summer it was named the third best-selling multigenerational master-planned community in the country. Wellen Park is massive, planned for an eventual 60,000 residents. Nine large-scale neighborhoods are currently in development. Among them is Mattamy Homes’ Renaissance, with low-maintenance villas and single-family homes and—yes—all kinds of resort-style amenities. Baseball buffs will rejoice; it’s near the new CoolToday Park, spring training home of the Atlanta Braves.

A charming home in Southside Village

A charming home in Southside Village

Image: Jenny Acheson

For Families

Southside Village

Families flock to this long-established West of Trail neighborhood for its eclectic mix of homes on tree-lined streets, everything from bungalows to classic Florida ranches and contemporary white-box residences. Its proximity to downtown Sarasota, the bay and the beaches can’t be beat, but the real draw is Southside Elementary School, considered one of the area’s top public schools. Oh, and it doesn’t hurt that Southside Village, with its boutiques and restaurants, and its phenomenally popular Morton’s Gourmet Market, is amidst it all.

Manatee River District

Last summer’s Wall Street Journal headline, “East Coasters are Snapping Up Vacation Homes Amid Coronavirus,” hit home in this established neighborhood along oak-lined Riverview Boulevard. Agents tell us large older homes on oversized lots, too big for empty nesters, that had languished on the market are being snapped up by youngish couples from Washington, D.C., New York and Connecticut with the ability to work remotely and who want good schools and outdoor space for their children to run around. “It’s a whole new buyer pool,” one realtor told us last summer. “They’re selling in one or two days when it used to take 12 or 18 months.”

Grand Palm

We’re putting Wellen Park on the list again with this Neal Communities project that is drawing families due to its many amenities, including an adventure playground, resort pool, fitness center, biking and walking paths, tennis, bocce and volleyball courts. “I showed a home to a woman with twin 9-year-old boys,” a real estate agent told us. “They looked around at the basketball court, the doggie park, the water slide and the hiking trails, and one of them said, ‘Mommy, this is all a boy could ask for.’” A-rated Taylor Ranch Elementary is nearby, and Grand Palm is zoned for Venice Middle School. At build-out there will be 2,000 attached villas and single-family homes, which currently start at $287,000.

Mallory Park at Lakewood Ranch

The 28 “villages” that comprise the mammoth master-planned Lakewood Ranch (18,000 homes and counting) are a mecca for families, none more so perhaps than this DiVosta community of single-family homes and townhomes. Its pool and sports courts are part of the appeal, and so is its adjacency to Bob Gardner Park and A-rated Gullett Elementary and brand-new Dr. Mona Jain Middle School. It’s affordable, too; prices start at $254,000.

A charming older home in McClellan Park.

A charming older home in McClellan Park.

Image: Gigi Ortwein

For the History Lover

McClellan Park

This leafy West of Trail neighborhood off South Orange Avenue, whose streets—Mietaw, Wewa, Illehaw—are named for the Calusa Indians who originally lived here, still boasts many 1920s cottages that have been expanded and upgraded to upscale standards. Lots of newer construction, too. Prices, ranging from the $500,000s to over $3 million, reflect the wide variety. McClellan Park’s proximity to the Southside Village dining and shopping district is a big plus; a linear pocket park leads residents right to foodies’ paradise: Morton’s Gourmet Market.

Sapphire Shores

Bordered by Sarasota Bay and some of Sarasota’s most important educational and cultural institutions, Sapphire Shores attracts artists and arts administrators, a smattering of New College and Ringling College faculty, and empty nesters who have injected new vitality into the grand old neighborhood. The original 1924-1925 deed restrictions mandated Mediterranean, Moroccan or Italianate architectural styles, and all 13 of those original homes built before the 1926 real estate crash are still standing. Construction practically halted until after World War II, so the remainder of the housing stock along wide, tree-lined Bay Shore Road is from the 1950s, ’60s and into the modern era.

Lido Shores

If midcentury modern architecture floats your boat, this Gulf-front neighborhood between St. Armands and Longboat Key is filled with gems. Among them is Paul Rudolph’s 1953 Umbrella House, “one of the five most remarkable houses of the twentieth century” according to Architectural Digest, spiffed up with an award-winning restoration and open for tours by the Sarasota Architectural Foundation. No museum feel here, however; contemporary architects have been at work in Lido Shores for some time, designing homes that bring a modern-day spin on those great architects of the past.

Venezia Park Historic District on the Island of Venice

The original small town that master planner John Nolen designed in 1926 has wide, landscaped boulevards and neighborhoods built around parks and playgrounds within strolling distance of the popular Venice Avenue shopping district (ice cream, anyone?) and a bike ride to the beach. It was one of the nation’s first master-planned cities, and thanks to the city’s strict building codes, in 94 years it hasn’t lost its charm. Forty-seven structures comprise the Venezia Park Historic District, and many of the original 1920s Spanish homes have been lovingly restored.

The Mark Sarasota is among the new condo projects changing the look of downtown Sarasota.

The Mark Sarasota is among the new condo projects changing the look of downtown Sarasota.

For the Upscale Urbanite

Downtown Sarasota: The Mark

Vibrant downtown Sarasota is the city’s civic and cultural center, and new condominium projects are rapidly changing its look and feel. The newest addition is the Mark Sarasota, a big, bright white 157-unit tower that stretches for most of South Pineapple Avenue between Main Street and Lemon and started welcoming its first residents in late 2019. You can’t miss the block-long mural on its western façade, Urbana Flora, by Miami artist Danny Doya. “Urban living is in, and downtown is attracting a very lively group of people no matter what their age is,” a real estate agent recently told us.  “You’re literally in the heart of downtown here. Value, value, value.”

Downtown Sarasota: Laurel Park

For those who desire downtown ambiance but like to keep both feet on the ground, downtown’s single-family neighborhoods are appealing alternatives. Laurel Park, between South Orange and Osprey avenues, is a National Historic District, and young professional families and empty nesters have been at work for the past decade restoring its Craftsman bungalows and Mediterranean Revival cottages, 270 of which hail from the 1920s. Nearby Towles Court is an artists’ colony with brightly painted, Florida Cracker-style cottages housing galleries and coffeehouses. A monthly gallery walk attracts art-loving browsers. Popular Bayfront Park is a stroll away, with a children’s splash park and a lively tiki bar for the over-21 crowd.

Downtown Bradenton: River Dance

Built in 2007, this 118-unit condo complex on the Manatee River, just east of the scenic Green Bridge, is a short stroll from downtown Bradenton’s many charms: restaurants on Old Main Street; a Saturday morning farmer’s market; the main public library; ArtCenter Manatee; Bishop Museum of Science and Nature, with its state-of-the-art planetarium; Manatee Performing Arts Center, home of the Manatee Players; and the Riverwalk, the popular 1.5-mile linear park that meanders along the river, where residents can walk, jog, bicycle and simply enjoy the sunsets. 

A farmhouse on scenic Snead Island.

A farmhouse on scenic Snead Island.

For the Outdoor Enthusiast

Snead Island

For boaters and fishermen, it’s hard to beat this scenic spit of land in far west Palmetto, where the Manatee River meets Terra Ceia Bay. Key West-style homes and Florida ranches dot the landscape; it’s unpretentious for the most part, but newish enclaves like Amberwynd have a smattering of million-dollar properties. Redfish Cove, an enclave of six riverfront homesites, is now under development. Emerson Point Preserve is a popular outdoor destination. Kayak and canoeing trails wind through the 365-acre county-owned recreation area, and there are picnic pavilions, hiking trails and an observation tower with awesome views of the Sunshine Skyway Bridge.

Phillippi Creek

This peaceful eight-mile waterway meanders south from nearby Fruitville Road to where it spills out into Sarasota Bay at Phillippi Estate Park, and the long-established central Sarasota neighborhoods that flank it—among them River Forest and parts of  Pinecraft and South Gate—offer excellent access to kayaking, canoeing and fishing. The Phillippi Creek Levee Trail, a Sarasota County public nature preserve, offers a walking path along the creek west of Beneva Road.

Venetian Golf & River Club

There are so many golf courses, public and private, in our region. We’ve singled out the Venetian Golf & River Club in North Venice here because it offers both an 18-hole golf course suited for players of all abilities and lots of lovely walking trails along the “wild and scenic” Myakka River (that’s an official designation, by the way) via its 70-acre nature park. There are two clubhouses, one exclusively for golf, the other social, and a very active USTA league tennis program.

Prestancia at Palmer Ranch

Whether golfing, bicycling the Legacy Trail or joining a swim club at the nearby Selby Aquatic Center, there’s lots to do at Sarasota’s largest master-planned community, Palmer Ranch. The upscale gated enclave of Prestancia boasts the private TCP Prestancia golf club, with two 18-hole championship courses for its members. Developed in the 1980s by the PGA Tour, it’s hosted eight Chrysler Cup Tournaments and five American Express Invitational Champions Tour events.

The Rosemary District is now packed with big new apartment and condominium complexes—among them CitySide, above.

The Rosemary District is now packed with big new apartment and condominium complexes—among them CitySide, above.

Image: Jenny Acheson

For the Young Professional

The Rosemary District

Seemingly springing up overnight, this downtown Sarasota neighborhood just north of Fruitville Road that five years ago was somewhat gritty is now packed with big new apartment and condominium complexes—among them CitySide, Arcos and The District at Rosemary Apartments. There’s a real street scene, with yoga and kickboxing studios, an artisanal cheese shop, cool modern home furnishing stores and restaurants like Spice Station and The Overton. One of our real estate writers describes it as “the “anti-gated community—lots of cultures, all clashing yet somehow managing to co-exist in a lively and energetic neighborhood unlike anything Sarasota has ever seen before.”

Payne Park Village

For young professionals who work downtown, location is everything at this new development of townhomes and single-family homes being built by David Weekley Homes. It’s a stone’s throw from the Sarasota County courthouse complex and police headquarters, and directly across the road from 39-acre Payne Park and its walking trails, children’s playground, skate park and tennis complex. And for bicyclers and walkers, after the workday is done, the Legacy Trail extension that’s now under construction will pass just to its east. Prices start in the upper $400,000s.

South Gate

Sarasota’s quintessential 1960s neighborhood was carved out of 1,200 acres of orange groves east of the Tamiami Trail. It’s sprawling; there are 2,100 modest concrete-block homes, most of them built with terrazzo floors and Florida rooms. Some home buyers have been making smart improvements that freshen up their appeal. And young professionals can’t beat the location, a quick drive to Sarasota Memorial Hospital, downtown and Siesta Beach. Recent listings on Zillow started in the low $300,000s, but we did spot one for $199,000.

Azalea Acres

A quick commute to downtown Bradenton, this 1960s-era neighborhood a couple of miles east of Manatee Memorial Hospital bordering the Manatee River is in transition. The small concrete-block homes on decent-sized lots are being snapped up by younger buyers who are improving them with new roofs and spiffed-up landscaping. Prices are climbing, real estate agents say—four old homes right on the river have been torn down and a luxury home builder is building on one of them—but if you hurry, you can still get a deal; we spotted a 1,092-square-foot, three-bedroom home built in 1960 on Zillow late last summer for $165,000.

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