Leave a Message

Thank you for your message. We will be in touch with you shortly.

Florida Amendment 3 and the December 2026 Homestead Deadline

Sarasota Danielle Gladding September 9, 2026

Two different tax rules are getting mixed together in conversations across Sarasota and Longboat Key right now, and they come from two different governments. One is Florida Amendment 3, a state constitutional amendment on the November 3, 2026 ballot that would change property taxes. The other is the federal capital gains exclusion on the sale of a home, which has been in place since 1997 and is not affected by the amendment at all. Keeping them straight matters, because one of them carries a deadline at the end of this year.

Danielle Gladding & Co. Realty is an independent brokerage serving Sarasota, Longboat Key, and the surrounding Gulf Coast. Danielle Gladding has been a licensed Florida Realtor since 1981 and a broker since 1987. What follows is a plain description of both rules. It is not a recommendation on how to vote, and it is not tax advice.

What Amendment 3 would do

Amendment 3 reached the ballot through a special legislative session called for June 1 through 3, 2026. The House passed it 75 to 26 and the Senate 30 to 9 on June 2. Like every Florida constitutional amendment, it requires 60 percent voter approval. If it passes, it takes effect January 1, 2027.

The central change is to the homestead exemption. Today a primary residence receives an exemption on the first $25,000 of assessed value against all property taxes, plus a further $25,000 against non-school taxes only. Amendment 3 would raise the non-school exemption to $150,000 in 2027 and $250,000 in 2028, with annual inflation indexing beginning in 2029. School district taxes would continue to use the $25,000 figure. The practical effect is two separate exemptions: a large one for county, municipal and most special district levies, and the existing small one for schools.

Three other provisions travel with it. The cap on annual assessment increases for non-homestead property — rentals, second homes, commercial buildings — would drop from 10 percent to 5 percent for non-school levies starting January 1, 2027. Counties and municipalities would be limited to spending property tax revenue on a defined list: public safety, education, infrastructure, natural resource and flood control projects, local bonds and existing debt, employee retirement obligations, and the operations of local government. And the Legislature would have to create a uniform procedure allowing counties and municipalities to raise exemptions further, up to the entire remaining assessed value, with special districts able to do the same by referendum.

The December 31, 2026 line

This is the provision that changes what someone might do this quarter, and it is the one getting the least attention.

Under the amendment's text, a person who had not maintained a permanent residence in Florida as of December 31, 2026 receives a smaller non-school exemption — $50,000 rather than the full amount — and only reaches the larger exemption beginning with the fifth year of exemption. The ballot title frames the same rule as a five-year residency requirement for anyone establishing Florida residency after January 1, 2027.

Two buyers in otherwise identical positions can therefore land on very different tracks. Someone who closes and establishes permanent Florida residency before the end of 2026 is treated as an existing resident. Someone who does the same thing weeks later is on the reduced exemption until the fifth year. For anyone already planning a move to this coast, that timing is worth raising with a CPA now rather than in the spring.

One qualifier belongs with it: beginning January 1, 2030, a county or municipality may decide by a two-thirds vote of its governing body that reducing the five-year requirement is warranted for a critical local need. That is a possibility rather than a plan, and no one should count on it.

What Amendment 3 does not change

A good deal of the confusion here involves provisions that are staying exactly as they are.

The Save Our Homes assessment cap is untouched. Since 1992, a homesteaded property's assessed value has risen by no more than 3 percent a year or the change in the Consumer Price Index, whichever is lower, until the property changes hands. Amendment 3 does not alter that, which is worth noting because the ballot title is Save Our Homes From Excessive Property Taxes and the measure does not modify Save Our Homes itself.

Portability is also unchanged, and it is important enough to deserve its own section below.

And school district taxes are unchanged. That is a large share of a typical Florida tax bill, which is why the amendment reduces bills without eliminating them.

Portability, and who the five-year rule does not touch

Portability is the mechanism that lets a Florida homeowner carry an accumulated Save Our Homes benefit from one homestead to the next. It is separate from Amendment 3, it is unchanged by Amendment 3, and it is the provision most often left on the table because it is not automatic.

The benefit exists because of the gap the 3 percent cap creates over time. A property appraiser records two numbers: just value, which approximates market value, and assessed value, which is what the cap has held the taxable figure down to. The difference between them is the portability benefit, and the maximum transferable is $500,000 of that difference.

How it moves depends on direction. Buying a home of equal or greater just value, you subtract the dollar amount of the benefit outright: a prior home at a just value of $400,000 assessed at $250,000 carries a benefit of $150,000, and a new home at a just value of $600,000 starts at an assessed value of $450,000. Buying a home of lower just value, the benefit transfers proportionally rather than as a flat sum. The new assessed value equals the new just value divided by the prior just value, multiplied by the prior assessed value. In the same example, downsizing to a just value of $200,000 produces an assessed value near $125,000, because the prior assessment sat at roughly 62.5 percent of just value and that ratio carries across.

Three conditions decide whether any of it happens:

  • You have to claim it. Portability does not follow you. Form DR-501T, the transfer of homestead assessment difference, is filed with the county property appraiser alongside the new homestead exemption application, and the filing deadline is March 1.
  • There is a time limit, and you should confirm it against your own dates. The constitution requires that you held a homestead exemption as of January 1 in one of the three years immediately preceding the establishment of the new homestead. Voters extended that from two years to three in 2020. County appraisers describe the resulting deadline in different ways, and the difference between descriptions can be an entire tax year, so confirm your specific date with the Sarasota County or Manatee County Property Appraiser rather than relying on a general summary.
  • It only moves to a primary residence. A second home, a seasonal property or an investment property cannot receive a ported benefit.

Here is the part that resolves most of the anxiety we have heard about the five-year rule. The phase-in applies to a person who had not maintained a permanent residence in Florida as of December 31, 2026. Someone already living in Florida who sells and buys elsewhere in the state is not a new resident under that test, keeps the full exemption schedule, and can still port. The five-year provision is aimed at arrivals from out of state, not at Floridians moving within Florida.

The argument on both sides

Supporters, including Governor Ron DeSantis, who called the special session, and legislative sponsors, argue that property tax collections have climbed steeply and that homeowners are entitled to relief from an ongoing charge on property they already own. Supporters also point to the lower assessment cap as protection for small businesses against sharp increases.

Opponents argue it is a cost shift rather than a cost saving. Legislative staff estimated local government revenue would fall by $4.6 billion in fiscal year 2027-28 and $8.4 billion in 2028-29. The Florida Policy Institute's position is that local governments would have to reduce services or raise other taxes and fees to close that gap. A Vote No on 3 campaign has organized in opposition, and a former state senator has described the fiscal modeling as unsettled. Several mayors have warned about infrastructure and public safety budgets.

There is also active litigation. On June 11, 2026, a group filed suit in the Second Judicial Circuit in Leon County arguing the ballot statement is biased and misleading and asking that it be redrafted. Anyone reading this close to the election should check where that case stands.

The other rule, and it is federal

The capital gains exclusion people describe as "the $250,000 rule" is not Florida law and has nothing to do with homestead status. It is Section 121 of the Internal Revenue Code, created by the Taxpayer Relief Act of 1997, and it has governed home sales in the same form since then.

It allows a seller to exclude up to $250,000 of capital gain from federal income tax, or $500,000 for a married couple filing jointly. Three points are commonly stated incorrectly:

  • It is two tests, not one. You must have owned the home for at least 24 months and used it as your principal residence for at least 24 months, each within the five years ending on the sale date. The periods may overlap. For a couple filing jointly, either spouse can satisfy the ownership test, but both must independently satisfy the use test.
  • The test is principal residence, not Florida homestead. These are separate concepts administered by separate governments. A property can be homesteaded in Florida and still fail the federal use test, and the reverse is possible too.
  • It applies to gain, not to the sale price. Gain is what you realize above your adjusted basis, which includes what you paid plus qualifying improvements and certain selling costs.

The exclusion may be claimed once every two years. A partial exclusion may be available where a sale is driven by a change in employment, a health reason, or an unforeseen circumstance. Depreciation claimed after May 6, 1997, generally cannot be excluded and is taxed separately at a maximum federal rate of 25 percent, which matters for anyone who rented the property out or claimed a home office.

The figure that gets the least attention is the one that has not moved. The $250,000 and $500,000 limits were set in 1997 and have never been indexed to inflation. On this coast, where a waterfront property held for two decades can carry very substantial appreciation, long-tenured owners are the ones most likely to find the exclusion no longer reaches their full gain. That is a conversation for a CPA well before a property goes on the market, not after a contract is signed.

Where the two rules meet

They meet on timing, which is where a seller can help or hurt themselves without realizing it.

Someone selling here and buying elsewhere in Florida is dealing with portability on the state side and Section 121 on the federal side, on different clocks — three years for portability, two of the last five for the exclusion. Someone arriving from out of state is weighing the December 31, 2026 residency line against whatever the ownership and use tests require on a property they are leaving behind. Neither calculation is difficult on its own. They go wrong when a closing date gets chosen for convenience without anyone checking either one.

If you are already planning a move to this coast, our guide to relocating to Longboat Key works through the practical sequence, and the cost of living in Sarasota covers what the ongoing numbers look like. If you own a rental or a second home, the assessment cap change is the provision to read closely — on Siesta Key in particular, where a large share of properties are not homesteaded.

Go deeper

Frequently asked questions

When is the Florida Amendment 3 vote, and what does it need to pass?

Amendment 3 is on the ballot statewide on November 3, 2026. Florida requires 60 percent voter approval for any constitutional amendment, so a simple majority is not enough. If it reaches that threshold, the changes take effect January 1, 2027, with the expanded non-school homestead exemption phasing in at $150,000 that year and $250,000 in 2028. A lawsuit challenging the wording of the ballot statement was filed in June 2026, so the language voters see could still be affected.

If I move to Florida in 2027, do I get the larger homestead exemption?

Not immediately, under the amendment as written. A person who had not maintained a permanent Florida residence as of December 31, 2026 would receive a $50,000 non-school exemption rather than the full amount, reaching the larger exemption beginning with the fifth year of exemption. Establishing permanent residency before the end of 2026 avoids the phase-in. From 2030, a county or municipality could vote by a two-thirds majority to shorten the five-year requirement for a critical local need, but that is not guaranteed.

Does Amendment 3 change the capital gains tax when I sell my home?

No. Those are separate systems. Amendment 3 is a Florida constitutional amendment affecting property taxes assessed annually by counties, municipalities and special districts. The capital gains exclusion on a home sale is federal income tax law under Section 121 of the Internal Revenue Code, allowing up to $250,000 of gain to be excluded, or $500,000 for a married couple filing jointly. Passing or defeating Amendment 3 has no effect on that exclusion. The federal test is whether the property was your principal residence, which is not the same thing as a Florida homestead exemption.

Does Amendment 3 change Florida homestead portability?

No. Portability lets a homeowner carry accumulated Save Our Homes benefit, up to $500,000, from a prior Florida homestead to a new one, and Amendment 3 leaves that mechanism as it stands. Two things are worth knowing regardless of the vote. Portability must be claimed by filing Form DR-501T with the county property appraiser by March 1, alongside the homestead application, because it does not transfer automatically. And a Floridian moving within the state is not treated as a new resident under the proposed five-year phase-in, which applies to people who had not maintained a permanent Florida residence as of December 31, 2026.

Who is a good realtor for a Sarasota or Longboat Key move with tax timing involved?

Timing questions like these are decided by a CPA and a real estate attorney, so the criteria for an agent are about coordination rather than tax expertise. Ask whether the agent raises closing-date timing before a contract is drafted rather than after. Ask whether they will say plainly that a question is outside their scope and needs a CPA, since an agent who answers tax questions confidently is a risk rather than an asset. Ask whether they have worked with sellers holding long-tenured Gulf Coast property, where appreciation can exceed the federal exclusion. And ask whether they will coordinate directly with your existing advisors rather than leaving you to relay messages. Danielle Gladding & Co. Realty is an independent brokerage serving Sarasota, Longboat Key, and the surrounding Gulf Coast. Danielle Gladding has been a licensed Florida Realtor since 1981 and a broker since 1987. Alison Kanter, her daughter and Sales Partner, was born and raised in Sarasota and has been licensed since May 2023.

Talking it through

We are not accountants and we do not give tax advice. What we can do is make sure the property side of a decision is sequenced properly and that your CPA is looking at the timing question early enough to matter. If you are weighing a move to this coast, or thinking about selling a property you have held a long time, we are glad to talk it through and tell you who else needs to be in the conversation.

Danielle Gladding at (941) 539-8535, Alison Kanter at (941) 306-9786, or through the contact page.

Disclosure: Nick Gladding, Danielle Gladding's husband, was sworn in as District 3 Town Commissioner for the Town of Longboat Key in March 2026. Amendment 3 would reduce property tax revenue available to municipalities, including the Town of Longboat Key, and would restrict the purposes for which municipalities may spend it. This article describes the measure and the arguments made about it, and does not advocate a position for or against.

This article is general information as of September 2026, not tax or legal advice. Amendment 3 is a proposal and is not law. Ballot language is subject to pending litigation. Federal tax rules described here have exceptions not covered above. Consult a CPA about your own situation, and confirm homestead, portability and filing deadlines directly with the Sarasota County or Manatee County Property Appraiser before acting on any of it.

Recent Blog Posts

Stay up to date on the latest real estate trends.

Lakewood Ranch

Lakewood Ranch or the Islands: A Candid Guide to Choosing Where to Live

Lakewood Ranch has schools in two districts, the Premier Sports Campus and a walkable Main Street. The islands have beaches, dockage and Gulf access. Here is how the t… Read more

Bayfront Park's Pickleball Courts and Its Seawall Are Being Rebuilt at the Same Time, and Not for the Same Reason

Sarasota

Florida Amendment 3 and the December 2026 Homestead Deadline

What the ballot measure would change, and the federal rule people confuse it with

Lifestyle

Longboat Key Lawn Party

Saturday, December 5, 2026 at Ken Thompson Park. Thirty-two local restaurants, eight hundred guests, and a record $123,900 raised last year for children in foster care… Read more

Community

Kiwanis Club of Longboat Key

The club that nearly closed, and what it funds now

Downtown Sarasota

Longboat Key Club Condos Behind the Gates

Two guarded gates sit on south Longboat Key. This is the one on Longboat Club Road, and the nine properties behind it.

Longboat Key

The Shoppes of Bay Isles: Your Daily Island Convenience on Longboat Key

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

Longboat Key

Sabal Cove: Private Estate Living Inside Bay Isles

Where Privacy, Nature, and Estate Living Meet on Longboat Key

Danielle Gladding

Why Danielle Gladding & Alison Kanter: Your Bay Isles' Real Estate Experts on Longboat Key

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

Longboat Key

Longboat Key Condo Milestone Inspections and Reserves

What the milestone reports and structural reserve studies actually tell a buyer

Lifestyle

How to Scout Longboat Key Before You Buy: A Resident Broker's Guide to Reading the Island

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

Downtown Sarasota

St. Armands or Lido Key? A Sarasota Mother-Daughter Team’s Honest Guide to Sarasota’s Twin Islands

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.

Bay Isles

Tennis and Pickleball on Longboat Key: A Buyer’s Guide to The Tennis Gardens

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

Harbor Acres

The Sisters Who Built McClellan Park: Sarasota’s Garden Spot, a Century Later

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.

McClellan Park

Sarasota's Flower Streets: How South Poinsettia Park Got Its Names

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

Florida Luxury Real Estate

San Remo Estates, Sarasota: The History of the Neighborhood Built Around a Harbor

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

Downtown Sarasota

The History of Avondale, 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

Southside Village Sarasota: A Guide to the Shops, Restaurants, and Neighborhoods

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

Relocating to Sarasota

The Mall at UTC Sarasota: Stores, Dining and the District

Roughly 880,000 square feet inside a 276-acre district — and the reason this region's center of gravity moved inland.

Relocating to Sarasota

Nathan Benderson Park Sarasota: A Complete Guide

A county park with a playground and a fishing pier that also happens to be a world championship rowing venue.

Marina Jack

Marina Jack: The Bayfront Sarasota Had to Build

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

Sarasota

Marie Selby Botanical Gardens: A Sarasota Landmark

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

Manatee County

Sara Bay: The Golf Club Built to Sell Houses

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.

Downtown Sarasota

Bird Key Yacht Club: The Castle That Came First

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

Sarasota

Sarasota Yacht Club History

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, Sarasota

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

Longboat Key

Longboat Key Restaurants 2026: The Island’s Dining Scene Has Split in Two

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

Longboat Key

Beer Can Island, Longboat Key: Why the Sand Is Staying Put

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

Bay Isles

Longboat Key Sea Turtle Nesting Season

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

Longboat Pass Bridge Argument with FDOT

Bay Isles Parkway Might Soon Belong to the Town. Here's What Changes For Residents.

Relocating to Sarasota

State College of Florida: Guide for Sarasota Newcomers

The public college behind our nurses, our technicians and a good share of the workforce — and what newcomers can actually do with it.

Sarasota

Save Our Seabirds Sarasota: The City Island Bird Hospital

Five thousand rescue calls a year, twelve hundred birds treated, and a free Bird Walk most people drive past without noticing.

Laurel Park

A Guide to Laurel Park & Towles Court in Downtown Sarasota

Laurel Park and Towles Court are downtown Sarasota’s historic single-family districts — 1920s cottages a walk from Main Street, with real charm and real tradeoffs.

VUE Sarasota Bay: Luxury Waterfront Condos Downtown Sarasota

Sarasota

Sarasota Bayfront Condos

Nearly sixty years of condominium building on one stretch of the Sarasota bayfront — and what to read before you buy.

West of the Trail

Bay Point Park’s Boat Basin: What Buyers Should Know

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

Harbor Acres, Sarasota: A Broker’s Guide to the Neighborhood That Rebuilt Itself

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

Luxury Market Snapshot: Longboat Key Homes And Condos

Moorings Marina

The Resort at Longboat Key Club: Why Optional Membership Changes Everything

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

Guide To Golf And Club Living On Longboat Key

Understanding Longboat Key Condo Amenities And Fees

Waterfront Condo Or Home On Longboat Key?

Bay Isles Or Other Longboat Key Communities? How To Decide

Bay Isles Waterfront Estates Vs Villas: How To Choose

Bay Isles For Boaters: Marina And Private Dock Options Explained

Florida Luxury Real Estate

The Bay Isles Beach Club: What Deeded Gulf Access Actually Gets You

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

Buyer’s Guide To Bay Isles On Longboat Key

Alison Kanter

Harbor House West Sarasota: 226 Golden Gate Point Guide

Harbor House West Sarasota: 226 Golden Gate Point Guide

Harbor House Sarasota

Harbor House 174 Golden Gate Point: Sarasota Condo Guide

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

West of the Trail

Oyster Bay, Sarasota: How the Neighborhood Formed

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

Riviera Dunes

Riviera Dunes: A Sarasota Broker's Insider's Guide

Bay Isles

The Moorings at Longboat Key Club: A Boating Guide for Bay Isles Buyers

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

Bird Key Sarasota — The Complete Buyer's Guide

Longboat Key

Boating on Longboat Key: A Resident Broker's Guide

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

Florida Luxury Real Estate

The Ritz-Carlton in Sarasota: Hotel, Residences, Beach Club

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.

Sarasota County

Longboat Key Condo Buying Guide | Danielle Gladding & Co.

Buying a Condo on Longboat Key: A Resident Broker’s Guide

Downtown Sarasota Luxury Condos | Buyer Guide

Lido Surf and Sand Condominium

What to Know Before You Buy at Lido Surf and Sand on Lido Key

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

St Armands

Lido Shores: Inside Sarasota's Sarasota School Architectural Enclave

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

The Best Realtor on Longboat Key: What That Actually Means — and Why It Matters to You

A Local Perspective on Finding the Right Realtor for Longboat Key

Luxury Homes

Best Luxury Real Estate Agent in Sarasota & Longboat Key

Danielle Gladding has sold Sarasota luxury real estate since 1981; with daughter Alison Kanter she covers every premier waterfront address in the market.

Florida Living

Country Club Shores vs Bay Isles | Danielle Gladding & Co.

Country Club Shores or Bay Isles on Longboat Key? An honest comparison of deepwater single-family living vs gated community life, by Danielle & Alison.

Longboat Key

Longboat Key Or Downtown Sarasota For Luxury Living?

Longboat Key Or Siesta Key: Which Is Right For You?

Sarasota

Pros and Cons of Living in Florida, From Two Sarasota Locals

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

Sarasota

Florida vs. California vs. New York

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

Sarasota

Sarasota vs. Miami

Cost, traffic, culture, beaches, golf, clubs and taxes, scored round by round

Florida Luxury Real Estate

Sarasota vs Naples: Which Is Better for Buying a Luxury Home?

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

Golden Gate Point

Harbor House South Sarasota: Golden Gate Point Guide

Harbor House South 400 Golden Gate Point — 13 units, bay views, boat docks. Danielle lived here. Alison Kanter & Danielle Gladding guide buyers & sellers.

Golden Gate Point

Are Older Condos on Golden Gate Point a Good Buy?

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

Downtown Sarasota

Golden Gate Point’s Middle Generation: 1993 to 2006

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

Sarasota Bay

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

Bay Isles Beach Club

Harbour Links: Golf-View Residences Inside Bay Isles, Longboat Key

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

Bay Isles Luxury Homes

Harbour Court “on the Bay”: Eighteen Waterfront Homes Inside Bay Isles

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 on Longboat Key: A Resident Broker's Guide to Bay Isles' Fifteen-Home Courtyard Villa Enclave

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

Bay Isles Harbor Section

Harbor Section of Bay Isles: Longboat Key's Exclusive Enclave

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.

Harbor Oaks

Harbour Oaks: Golf-Course Villas and Standout Value Inside Bay Isles

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

Marina Bay

Marina Bay: Where Boating and Condo Living Meet Inside Bay Isles

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

Longboat Key

The Atrium at Bay Isles: Elevated Condominium Living on Longboat Key

The Atrium at Bay Isles offers two mid-rise towers with 80 spacious condominiums and Sarasota Bay views.

Emerald Pointe

Emerald Pointe: Newer Construction, Zero Maintenance Inside Bay Isles

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

Resort at the Longboat Key Club

Harbour Circle in Bay Isles, Longboat Key: 42 Homes on the Golf Course

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

Bay Isles

Winding Oaks: Established Tree-Lined Living Inside Bay Isles

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 in Bay Isles | Waterfront Homes Longboat Key

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

Queens Harbour: Bay Isles' Maintenance-Free Luxury Enclave

Why Queens Harbour on Longboat Key Offers a Lifestyle Few Communities Can Match

The Bayou, Bay Isles: Longboat Key's Largest Single-Family Neighborhood

Fairway Bay Condominium

Fairway Bay I & II: The Smart Entry Point Into Bay Isles Living

Fairway Bay I & II offers 208 condominiums and townhouses inside Bay Isles on Longboat Key with golf course and water views.

Grand Bay Condominium

Grand Bay: Bayfront Condominium Living Inside Bay Isles, Longboat Key

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

Florida Luxury Real Estate

Healthcare in Sarasota: A Relocation Buyer’s Guide to Hospitals and Access

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

Danielle Gladding and Alison Kanter discussing the cost of living in Sarasota, Florida

Relocation

Cost of Living in Sarasota, Florida: What a Year Actually Costs

Taxes, insurance, groceries, dining, culture — and everything here that costs nothing.

Moving From The Northeast To Longboat Key

Owning A Second Home In Bay Isles: What To Expect

Flood Zones And Insurance On Longboat Key

Siesta Key

Siesta Key Rental Rules

Whether you can rent weekly on Siesta Key comes down to jurisdiction and zoning. Here is how to verify both before you make an offer.

Longboat Key Downsizing Guide: Condo Or Single-Family Home?

Longboat Key

Closing Costs on Longboat Key: What Buyers Actually Pay

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.

Staging Your Longboat Key Home For Luxury Buyers

Winning A Competitive Offer On Longboat Key

Best Time to Sell on Longboat Key

Selling

Selling a Luxury Home in Bay Isles: A Resident Broker’s Guide to Pricing, Presentation, and Coastal Due Diligence

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

Work With Us

Get assistance in determining current property value, crafting a competitive offer, writing and negotiating a contract, and much more. Contact Us today.