Downtown Sarasota Danielle Gladding & Alison Kanter August 4, 2026
Avondale was not built to be an expensive neighborhood. It was built to be an affordable one, and it failed at that badly enough that the developers gave up and sold it.
That is not the version you will find on most real estate sites, which describe Avondale as a historic enclave of old Florida charm and leave it there. The real sequence is more interesting, and it explains almost everything a buyer notices walking these streets today — why the architecture does not match, why some lots are twice the size of others, why a 1926 Mediterranean sits three doors from a 1958 ranch, and why the neighborhood has held its value through every downturn since.
Danielle lived in Avondale when her son Alex was in grade school at Southside Elementary. We have sold in this neighborhood across five decades. What follows is the documented history, drawn from the Sarasota County Historical Commission marker that stands at Bahia Vista Street and Brewer Place and from the records kept by the Avondale Residents Association.
1913: The Land South of Hudson Bayou
In December 1913, Oscar and Alice Burton joined Arthur B. Edwards — a real estate developer who would go on to serve as mayor of Sarasota, first from 1914 to 1915 and again from 1920 to 1921 — and his wife Fannie in selling the land south of Hudson Bayou to the Sarasota Improvement Company.
To understand what that land was, understand what Sarasota was. The county population in 1910 was 840 people. The Tamiami Trail, the road that now defines the eastern edge of the neighborhood and carries tens of thousands of cars a day, was dirt.
1914–1922: Avondale Heights, and Nine Years of Nothing
The subdivision was first platted in 1914 and recorded in 1915 as Avondale Heights. It was advertised as a place for families of average means, and the pitch was aggressive for its day: seventy-five lots at $250 apiece, fifty dollars down and ten dollars a month, with a modern bungalow valued at $1,500 given away to draw attention to the development.
It did not work. Avondale Heights sold slowly and sat largely undeveloped for the better part of a decade. Sarasota simply did not yet have the population to absorb it — the boom was still years away, and a subdivision priced for working families was competing with land that was effectively free everywhere else.
1923: Three Men Buy the Leftovers
In 1923, Irving Bacheller, Edward Brewer, and Fred Woolley purchased the undeveloped lots and formed the Bacheller-Brewer Corporation. They did not try to make the original plan work. They threw it out.
The subdivision was re-platted as Avondale — the "Heights" dropped along with the original positioning. Individual lots were enlarged. Streets were widened. One street was eliminated entirely. A water system went in. The seawall along Hudson Bayou was built, and the bayou was dredged for boats. The new plat ran to eleven blocks, lettered A through K, and roughly eighty lots.
Then came the decision that made the neighborhood. Deed transfers described Avondale as a model suburban development, and a restriction was written barring any dwelling built for less than $5,000. In 1923 dollars that was not a suggestion — it was a wall. The covenant remained in force until January 1950.
Consider what that single line did. Nine years earlier the same ground had been marketed at $250 a lot with ten-dollar monthly payments. Now the cheapest house you were permitted to build cost twenty times a lot. Avondale went from workforce housing to an exclusive address by contract, not by accident.
1925: Sold Out
The timing was extraordinary. The Florida land boom arrived, and it arrived hard. Sarasota County’s population, 840 in 1910, stood at 8,284 by 1925 — roughly a tenfold increase in fifteen years.
Avondale sold out. By the end of 1925 the Sarasota Herald reported that every lot had been sold except those fronting the bayous, and the subdivision had gained recognition as one of the finest in Sarasota. The Bacheller-Brewer Corporation hired a Milwaukee architectural firm to build a 600-foot concrete pier on the bayou. A Chicago artist, Gibson Catlett, painted a fourteen-foot promotional canvas depicting the completed development under a Florida sunset; it was displayed at a national convention of Realtors in Washington.
Sarasota in 1926 was a young city with no traffic problems, a train that crossed the main artery several times a day, no street car system, and a single bus line carrying eighteen passengers from Five Points to Siesta Key. And Avondale was one of the best addresses in it.
1926: The Model Home, and the Crash
The larger bayou-front lots were the last to move, and to sell them the Bacheller-Brewer Corporation went after wealthy buyers with a model home. They commissioned Thomas Reed Martin — a well-known Sarasota and Chicago architect — to design a Mediterranean Revival residence on Lincoln Drive, a two-story central core flanked by one-story wings. It was built in 1926 to demonstrate the quality of construction the corporation was promoting.
It was finished almost exactly as the Florida land boom collapsed.
The house did not sell. It stood vacant until 1929, when it was bought by Homer Galpin, an attorney and former Illinois state senator from Chicago. In 1992 it was added to the National Register of Historic Places, where it remains — a building that was designed as a sales tool for a boom that had already ended by the time anyone could tour it.
1930–1970: The Slow Fill
This is the part of the story that explains what you actually see today. The boom died, and Avondale did not fill in as planned. Some Colonial Revival homes went up in the 1930s. Then the neighborhood filled in substantially through the 1950s and 1960s — which is why a great deal of the housing stock in a subdivision platted in 1914 is mid-century.
The $5,000 covenant expired in January 1950, right as that infill was beginning. The neighborhood kept its character anyway, because by then location was doing the work the covenant had done.
What Is Still There
Most century-old subdivisions leave behind nothing but a street grid. Avondale left more, and it is all still visible on a twenty-minute walk:
• The lion urns placed at the original entry corners. Two of the original pedestals with seating remain in place at Yale Avenue and Bahia Vista Street.
• At Lincoln Drive and Brewer Place, low to the ground, the only surviving concrete street identification from the original development. Brewer Place is named for one of the three men who bought the failed subdivision.
• The Hudson Bayou seawall, built as part of the 1920s improvements.
• Two homes on Lincoln Drive listed on the National Register of Historic Places, plus two on the Sarasota County register — one on Alta Vista Street, one on Brewer Place.
• The Sarasota County Historical Commission marker at Bahia Vista Street and Brewer Place, which tells a compressed version of everything above.
What This History Means If You Are Buying Here
History on a neighborhood page is usually decoration. Here it is practical, and it changes four things about how we would approach a purchase in Avondale.
The housing stock is three different purchases
A 1920s Mediterranean, a 1950s ranch, and a 2020s custom build are not variations on a theme — they are separate transactions with separate risks. The original houses carry the highest renovation exposure and, in a few cases, design review. The mid-century infill is usually the value entry and often the teardown candidate, because much of the value sits in the land. The new construction arrives at current elevation, current codes, and the highest price per square foot in the neighborhood. Price the renovation and the rebuild as alternatives before making an offer on anything older here.
Designation attaches to houses, not to the neighborhood
Avondale is a historic neighborhood, but it is not a blanket historic district in which every home is restricted. Designation applies to specific structures. That is good news for a buyer planning to build, and a serious question for a buyer looking at one of the designated homes. Confirm the designation status of the individual property before planning any exterior alteration, addition, or demolition — not the neighborhood, the parcel.
The lot lines were redrawn once and have moved since
The 1920s re-plat enlarged lots and eliminated a street. Parcels have been split and combined in the century since. Do not assume the lot geometry on a listing, and do not assume what you can build on it. Get setbacks, height limits, and lot coverage for that specific parcel from the City of Sarasota, in writing, before you plan anything.
The seawall has a birthday, and the bayou has a ceiling
The seawall along Hudson Bayou dates in part to the 1920s development. Age alone does not make a seawall bad, and many stretches have been rebuilt. It does make the inspection non-optional on any waterfront parcel here.
The bayou itself carries a limit the 1920s marketing never mentioned and current listing copy still skips. Avondale’s frontage sits upstream of a low fixed bridge, and federal navigation data puts the clearance of that span under ten feet. Every boat kept at an Avondale dock passes beneath it to reach Sarasota Bay. That makes this small-boat water — a center console or a runabout, not a sailboat and not a cruiser with a tower. Bay Point Park, the separate neighborhood immediately across Orange Avenue, sits downstream of that bridge at the mouth of the bayou with direct open-bay access. Two neighborhoods a street apart, on opposite sides of a fixed span, and the difference is worth understanding before anyone writes a check.
The full due-diligence list, the school picture, and how Avondale compares to the neighborhoods around it are on our Avondale neighborhood page.
The Pattern Worth Noticing
Avondale was mispriced at the start, reinvented on purpose, sold out in a mania, orphaned by a crash, and filled in slowly over forty years. It survived all of it, and it is now one of the most sought-after addresses on the Sarasota mainland.
The reason is the one thing that never changed: it sits west of the Trail, minutes from downtown, next to the hospital, on the water, under oaks, on streets you can walk. Every other variable in the neighborhood’s history moved. That one did not. When we are asked which Sarasota neighborhoods hold up through a soft market, that is the quality we are looking for — an advantage that is structural rather than fashionable.
If You Are Looking at Avondale from Out of State
Most people we walk through this neighborhood are arriving from New York, Illinois, Massachusetts, Michigan, Connecticut, or New Jersey, weighing Avondale against three or four other Sarasota neighborhoods on a compressed timeline. The questions are consistently the same: homestead and portability, how Florida property tax actually assesses after a purchase, insurance in a coastal county, what changes seasonally, and which neighborhoods hold value when the market softens.
Our [Sarasota Relocation Guide] covers all of it — the tax picture, the insurance landscape, the rhythm of the season, and a neighborhood-by-neighborhood comparison across Sarasota and Manatee County. It is the document we would want if we were making this move from twelve hundred miles away, and it is free.
A Private Conversation Costs Nothing
If Avondale is on your list, we can tell you which of the three housing generations fits what you are actually trying to do, which blocks are seeing teardowns, and which two or three neighborhoods you should be comparing it against before you commit. If you own here and are thinking about selling, we will give you a private valuation and a straight read on your position.
Reach out whenever you are ready. A private conversation costs nothing.
Frequently Asked Questions About Avondale’s History
When was Avondale in Sarasota built?
Avondale was first platted in 1914 and recorded in 1915 as Avondale Heights, then re-platted as Avondale in the 1920s by the Bacheller-Brewer Corporation. Most of the lots sold during the Florida land boom of 1925, but because the boom collapsed the following year, a large share of the neighborhood’s actual housing stock was built during the 1950s and 1960s.
Who developed Avondale in Sarasota?
Avondale was originally developed by the Sarasota Improvement Company, which acquired the land south of Hudson Bayou in December 1913 from Oscar and Alice Burton and from Arthur B. Edwards, a developer and future Sarasota mayor, and his wife Fannie. After the first subdivision failed to sell, Irving Bacheller, Edward Brewer, and Fred Woolley bought the undeveloped lots in 1923 and formed the Bacheller-Brewer Corporation, which re-platted and repositioned the neighborhood.
Was Avondale originally an affordable neighborhood?
Yes — Avondale was originally platted as Avondale Heights and advertised in 1915 as a place for families of average means, with seventy-five lots offered at $250 each on a plan of fifty dollars down and ten dollars a month. It sold poorly for nearly a decade, and the neighborhood only became an upscale address after the 1920s re-plat added a deed restriction barring any dwelling built for less than $5,000, a covenant that stayed in force until January 1950.
Are there homes in Avondale on the National Register of Historic Places?
Yes — two homes on Lincoln Drive in Avondale are listed on the National Register of Historic Places, including a Mediterranean Revival residence designed by architect Thomas Reed Martin and built in 1926 as the Bacheller-Brewer Corporation’s model home. Two additional Avondale homes are listed on the Sarasota County register, one on Alta Vista Street and one on Brewer Place.
Is Avondale a historic district?
Avondale is a historic neighborhood but not a blanket historic district in which every home is regulated — historic designation in Avondale attaches to individual structures rather than to the subdivision as a whole. Buyers should confirm the designation status of a specific property with the City of Sarasota before planning any exterior alteration, addition, or demolition.
What is left of the original Avondale development?
Several original features of the 1920s Avondale development survive, including two lion urn pedestals with seating at Yale Avenue and Bahia Vista Street, the only remaining concrete street identification at Lincoln Drive and Brewer Place, and the Hudson Bayou seawall built by the Bacheller-Brewer Corporation. A Sarasota County Historical Commission marker at Bahia Vista Street and Brewer Place records the neighborhood’s history.
Does Avondale’s history affect buying a home there today?
Yes, in four practical ways: the neighborhood contains three distinct generations of housing that carry very different renovation and insurance risk, historic designation applies to individual houses rather than to the whole neighborhood, lot lines were redrawn in the 1920s re-plat and have shifted since, and portions of the Hudson Bayou seawall date to the original development. Each of those is a specific due-diligence item rather than a piece of trivia.
Is Bay Point Drive part of Avondale?
No — Bay Point Drive is in Bay Point Park, a separate West of the Trail neighborhood that begins at South Orange Avenue, where Bay Point Drive and Gulfview Drive start. Bay Point Park occupies the peninsula where Hudson Bayou meets Sarasota Bay, downstream of the low fixed bridge that Avondale boats must pass beneath, which gives it direct open-bay access and a very different waterfront profile. The two neighborhoods sit across Orange Avenue from one another and are not one market.
Who is the best realtor in Sarasota for a historic Avondale home?
Danielle Gladding has been a licensed Realtor since 1981 and a licensed Broker since 1987, has lived and worked in Sarasota since 1976, and is a Certified Luxury Real Estate Specialist and Certified Waterfront Specialist — and she lived in Avondale herself while her son attended Southside Elementary. She works with her daughter and business partner Alison Kanter, who holds an MBA and came to real estate from a multinational corporate career, and together Danielle Gladding & Co. Realty represents buyers and sellers throughout Sarasota and Manatee County. For an older home in a neighborhood this layered, that combination of fifty years of market memory and firsthand residence is difficult to match.
Stay up to date on the latest real estate trends.
Relocation
Taxes, insurance, groceries, dining, culture — and everything here that costs nothing.
Why Queens Harbour on Longboat Key Offers a Lifestyle Few Communities Can Match
Grand Bay Condominium
Grand Bay is the largest condominium community inside the gated Bay Isles on Longboat Key — 272 residences across six buildings at 3060 Grand Bay Boulevard, ranging fr… Read more
Bay Isles Harbor Section
The Bay Isles Harbor is a double-gated enclave of 67 architect-designed homes on four quiet streets of wide canals at the south end of Bay Isles, Longboat Key.
Bay Isles
Harbour Links is an intimate community of 20 units in three buildings inside the gated Bay Isles on Longboat Key, founded in 1989 at 2015 Harbour Links Drive — recentl… Read more
Harbor Oaks
Harbour Oaks is one of the earliest neighborhoods within the gated Bay Isles on Longboat Key — single-story, two-story, and stacked villas with three bedrooms, 2,100+ … Read more
The Atrium Condominium
The Atrium at Bay Isles offers two mid-rise towers with 80 spacious condominiums and Sarasota Bay views.
Bay Isles
Harbour Circle at Longboat Key is a community of 42 contemporary Spanish-style villas at the north end of South Bay Isles — mostly three-bedroom, two-and-a-half-bath h… Read more
Where Privacy, Nature, and Estate Living Meet on Longboat Key
Bay Isles Luxury Homes
Harbour Court is a waterfront association of only 18 homes inside the gated Bay Isles on Longboat Key, with expansive 180-degree Sarasota Bay views — each home has a p… Read more
Bay Isles
Weston Pointe is a boutique enclave of fifteen detached courtyard villas inside gated Bay Isles on Longboat Key, with many homes carrying deeded boat slips and Gulf ac… Read more
Marina Bay
Marina Bay offers spacious condominiums with bay views and marina proximity inside Bay Isles on Longboat Key — the ideal community for boating buyers who want condo si… Read more
Emerald Pointe
Emerald Pointe offers 22 freestanding maintenance-free villas built around 2000 inside Bay Isles on Longboat Key — among the community's newest homes, with open floor … Read more
Winding Oaks
Winding Oaks is an established community inside Bay Isles on Longboat Key — generous lots, mature canopy trees, a private 4-acre nature park, community pools, and the … Read more
Bay Isles
Corey's Landing is a gated enclave of sixty-one homes and patio villas inside Bay Isles on Longboat Key, with open-bay and golf-course residences, pool, tennis, and de… Read more
Bay Isles
Fairway Bay I & II offers 208 condominiums and townhouses inside Bay Isles on Longboat Key with golf course and water views.
Six88
Golden Gate Point's new-construction buildings are ONE88, AQUA, The Pearl, Evolution, En Pointe, Peninsula Sarasota, Six88, The Owen and Amara on Sarasota Bay.
Sarasota
Bird Key Yacht Club is a private club in Sarasota, Florida, founded in 1959 on the ground of New Edzell Castle and built around a marina, dining, tennis and a full soc… Read more
Downtown Sarasota
Marina Jack is an open commercial marina on the downtown Sarasota bayfront, operating on city-owned land created by dredge and fill in the late 1950s and leased to a p… Read more
Bradenton
Sara Bay opened in 1926 as a Donald Ross course built to sell lots — and what that century-old model still teaches a buyer walking into a sales center today.
Longboat Key
Greer Island, the north-end spit that locals call Beer Can Island, has needed no emergency dredge since 2023, four years after Longboat Key completed its seven-groin n… Read more
Florida Luxury Real Estate
The Ritz-Carlton in Sarasota is not one building: it is a hotel, residences downtown and at The Quay, a private Beach Club on Lido Key, and a Tom Fazio golf course.
Downtown Sarasota
The Sarasota Yacht Club was incorporated on June 21, 1926, and marked its centennial in 2026 with an approved clubhouse expansion and a full replacement of its marina … Read more
Florida Luxury Real Estate
The Field Club in Sarasota occupies a 1920s David Adler estate on Roberts Bay that Stanley Field sold in 1957 at a restricted price, and only to a buyer who would keep… Read more
Downtown Sarasota
Nine condominium buildings on Golden Gate Point date from 1993 to 2006: Renaissance, Alta Mer, Toscano, The Phoenix, Golden Bay, Majestic Bay, Vista Bay Point, Grande … Read more
Laurel Park
Laurel Park and Towles Court are downtown Sarasota’s only true historic single-family districts — 1920s cottages a walk from Main Street, with real charm and real trad… Read more
Lakewood Ranch
Lakewood Ranch is built for family life and top schools; the islands are built for the water and an adult lifestyle. The right Sarasota choice depends less on budget t… Read more
Lido Shores
Lido Shores is the densest concentration of Sarasota School of Architecture residences in the country — Paul Rudolph, Ralph Twitchell, the Umbrella House. Here is the … Read more
Bay Isles
Sea turtle nesting season on Longboat Key runs May 1 through October 31, and the Town’s Chapter 100 ordinance reaches any property whose artificial light is visible fr… Read more
Sarasota
Florida has no state income tax, California’s top rate is 13.3 percent, and a New York City resident can face a combined state and city top rate of 14.776 percent — th… Read more
Florida Living
Florida's main pros are no state income tax, year-round outdoor living, and six distinct regions to choose from; its main cons are summer heat, hurricane season, growt… Read more
The Field Club
Oyster Bay Estates in Sarasota took shape in the early 1950s on the east shore of Roberts Bay, around a 1920s Chicago winter estate that had already become the private… Read more
Luxury Homes
Danielle Gladding has sold Sarasota luxury real estate since 1981; with daughter Alison Kanter she covers every premier waterfront address in the market.
Florida Luxury Real Estate
Naples is the more refined and more expensive of the two markets and skews decisively older, while Sarasota is more approachable, wider in age range, and generally giv… Read more
San Remo Estates
San Remo Estates in Sarasota was platted between 1953 and 1956 by Roy Construction Company, which filled roughly thirty acres of Sarasota Bay bottom to create the neig… Read more
South Poinsettia Park
South Poinsettia Park is called Sarasota's Flower Streets because its 1920s developers gave the roadways a botanical theme, then used pioneer family names where the fl… Read more
McClellan Park
Sisters Katherine and Daisietta McClellan laid out McClellan Park in 1915 and 1916, hiring landscape architects and taking the street names from a Calusa shell mound.
Bay Isles
The Bay Isles Beach Club at 2111 Gulf of Mexico Drive is a private, resident-only Gulf beach facility, and every home inside the Bay Isles gates on Longboat Key carrie… Read more
Sarasota
Sarasota Memorial Health Care System was named one of the nation’s 15 Top Health Systems in 2026, which makes Sarasota’s medicine unusually strong — but your address d… Read more
Florida Luxury Real Estate
Southside Village is Sarasota's oldest shopping district — two walkable streets behind Sarasota Memorial Hospital, anchored by Morton's Market and ringed by West of th… Read more
Longboat Key
Boating access on Longboat Key comes down to how the slip is legally held, the depth at mean low water, the bridge clearances on your route to the Gulf, and which coun… Read more
Longboat Key
Longboat Key sits in two counties, and buyer closing costs differ on each side of the line — including who customarily pays for the owner's title insurance policy.
Bay Point Park
Bay Point Park in Sarasota has a shared boat basin owned by its neighborhood association, described in state lease records as a nine-slip facility serving roughly fort… Read more
Downtown Sarasota
Marie Selby Botanical Gardens is a 15-acre bayfront botanical garden in downtown Sarasota, created from the home and grounds Marie Selby left to the public and opened … Read more
Downtown Sarasota
Avondale was first platted in 1914 as workforce housing that failed to sell, then re-platted in the 1920s by the Bacheller-Brewer Corporation as one of Sarasota’s most… Read more
Downtown Sarasota
Harbor Acres is a waterfront neighborhood west of the Trail in Sarasota, minutes from downtown and Sarasota Memorial Hospital, where most original 1950s ranches have g… Read more
Longboat Key
Longboat Key dining has separated into two tiers in 2026 — an ultra-luxury layer at the south end anchored by The St. Regis, and an expanding locals-first scene throug… Read more
Sarasota
Buying a Condo on Longboat Key: A Resident Broker’s Guide
Golden Gate Point
A 22-acre peninsula reaching into Sarasota Bay between downtown and the Ringling Bridge, holding more than twenty condominium buildings across three generations — 1960… Read more
Pier 550
Six original condominium buildings survive on Golden Gate Point, built between 1962 and 1970, holding roughly ninety residences on a 22-acre peninsula that cannot add … Read more
Lido Surf and Sand Condominium
Lido Surf and Sand is a 105-residence, eight-story 1976 beachfront condominium on Lido Beach in Sarasota where leasing is capped at two one-month leases a year and sal… Read more
Bay Isles
The Moorings is the 291-slip deep-water marina inside Bay Isles on Longboat Key, where slips can be bought outright as real estate or rented from the resort without Cl… Read more
Longboat Key
The Tennis Gardens at the Resort at Longboat Key Club holds 20 Har-Tru clay courts plus pickleball, with daily clinics and a match-arranging service open to members an… Read more
Bay Isles
The Resort at Longboat Key Club offers Bay Isles residents 45 holes of championship golf, 20 Har-Tru tennis courts, a 291-slip marina, spa, fitness, and exceptional di… Read more
Luxury Living
Danielle Gladding
Danielle Gladding has lived in Bay Isles, served the community as a Kiwanis president, guided buyers and sellers since 1981, and is the broker whose husband serves as … Read more
Bay Isles
The Shoppes of Bay Isles at 525 Bay Isles Parkway offer everyday convenience for Bay Isles residents — anchored by Publix, with CVS, Chase, Truist, salons, fitness, an… Read more
Golden Gate Point
Harbor House West Sarasota: 226 Golden Gate Point Guide
Longboat Key
Longboat Key is an island condo market with small sample sizes and seasonal swings, so the buyers who do best read it by building and submarket — not by island-wide av… Read more
Longboat Key
A good Longboat Key scouting trip tests the island at four different hours and in more than one season, because the barrier island that charms you at sunset can drive … Read more
Selling
Selling a luxury home in Bay Isles on Longboat Key means pricing by micro-market across its 16 residential neighborhoods, leading with dockage, and preparing coastal d… Read more
Golden Gate Point
Harbor House South 400 Golden Gate Point — 13 units, bay views, boat docks. Danielle lived here. Alison Kanter & Danielle Gladding guide buyers & sellers.
Lido Shores
They share a bridge, a zip code, and a way of life — but the buyer who belongs on Lido is not the buyer who belongs on St. Armands. Here’s how to tell the difference.
Florida Living
Country Club Shores or Bay Isles on Longboat Key? An honest comparison of deepwater single-family living vs gated community life, by Danielle & Alison.
Golden Gate Point
Harbor House at 174 Golden Gate Point — 13 owner-occupied residences, Sarasota Bay & Ringling Bridge views, boat dock, fishing pier. Alison Kanter & Danielle Gladding … Read more
A Local Perspective on Finding the Right Realtor for Longboat Key
Get assistance in determining current property value, crafting a competitive offer, writing and negotiating a contract, and much more. Contact Us today.