Selling a Weston Home You’ve Owned 20 Years (2026)

What should you expect selling a Weston home you’ve owned 20 years?

You likely have real equity, and more decisions than you expect. A home bought in Weston around 2006 was bought near the top of the last boom, then rode the crash and the run in prices since 2020. The decisions attached to it are where long tenure owners get caught, because the last time you sold a house the rules and the numbers were different.

Three things matter most when you sell after two decades in Weston: what you actually owe in taxes on the gain, what happens to the Save Our Homes cap that held your tax bill down all these years, and how long the home takes to sell in a market that is not the 2021 market. Take them in order.

How much have Weston home prices changed since 2021?

I pulled six years of closed single family sales for Weston from the MLS, and the trend is clear. The median single family home in Weston, Florida sold for $915,000 in the first half of 2026, up from $675,000 in 2021, based on my own MLS closed sales pull, an increase of 35.6 percent. Average single family sale price climbed even more, up 37.1 percent over the same window, per my MLS pull. If you bought in the mid 2000s, your purchase price predates this entire table, so your gain depends on what you paid then, not on these percentages.

| Year | Closed single family sales | Median sale price | Median price per sqft | Median days on market | Source |

|—|—|—|—|—|—|

| 2021 | 1,059 | $675,000 | $284.38 | 12 | my MLS pull |

| 2022 | 681 | $865,000 | $364.41 | 13 | my MLS pull |

| 2023 | 547 | $850,000 | $377.27 | 21 | my MLS pull |

| 2024 | 544 | $950,000 | $414.36 | 24 | my MLS pull |

| 2025 | 551 | $948,000 | $393.90 | 42 | my MLS pull |

| 2026 (first half) | 289 | $915,000 | $405.01 | 40 | my MLS pull |

Every figure above is Weston single family, closed sales, from my own Matrix pull dated July 29, 2026. The public portals blend condos and townhomes into their Weston number and show something lower, so do not be thrown when an online estimate looks softer than what single family homes on your street actually close for. The sales trough was 2024 in Weston, down 48.6 percent from 2021 volume, per my MLS pull, and 2025 was the first annual sales increase since 2021.

One more piece of context for a long tenure owner. If you have held onto the home partly because moving means giving up a low mortgage rate, you are not alone. The Federal Housing Finance Agency estimated the rate lock effect kept about 1.33 million homes off the national market between the second quarter of 2022 and the fourth quarter of 2023, per its Working Paper 24-03. That hesitation is understandable. It should not be the only input in a decision this large. For the side by side data on both markets, the breakdown in Davie versus Weston home prices since 2021 shows how the two towns moved.

The tax that surprises 20 year owners

Here is the number to check first. When you sell a primary residence, federal law lets you exclude up to $250,000 of gain if you file single and up to $500,000 if you are married filing jointly, as long as you owned and lived in the home for at least two of the last five years. A 20 year owner who still lives in the home clears that ownership and use test. You can read the rule straight from the IRS on the sale of your home.

The catch is what counts as gain. Your gain is the sale price minus your original cost basis, which is roughly what you paid plus the capital improvements you made over the years. Per the IRS rules above, whether your gain exceeds the $250,000 single or $500,000 married exclusion depends on your purchase price, your improvements, and your sale price. Here is what real Weston resales show. I pulled Broward County Property Appraiser sales history on October 26, 2026 for Weston detached single family homes that resold in 2025 or 2026, and found four whose previous recorded sale was in 2006.

| Bought in 2006 | Resold in 2025 | Difference | Source |

|—|—|—|—|

| $540,000 | $882,500 | $342,500 | per BCPA, pulled 10/26/2026 |

| $610,000 | $1,050,000 | $440,000 | per BCPA, pulled 10/26/2026 |

| $620,000 | $1,028,000 | $408,000 | per BCPA, pulled 10/26/2026 |

| $638,000 | $880,000 | $242,000 | per BCPA, pulled 10/26/2026 |

Source: Broward County Property Appraiser sales history, pulled October 26, 2026. Those are sale price differences before improvements and selling costs, which lower the taxable gain. All four came in under the $500,000 married exclusion, and three of the four were above the $250,000 single exclusion, so filing status mattered as much as the price.

Any gain above your exclusion is taxed at the federal long term capital gains rate of up to 20 percent depending on your income, and higher income sellers can also owe the 3.8 percent net investment income tax on the taxable part of the gain, per IRS Topic 559. Florida adds no state income tax on top, which is one reason a Florida sale is friendlier than the same sale up north.

Your exact number depends on your cost basis, the improvements you can document, and your filing status, so this is not something to estimate off a headline. This is the kind of math I build with a seller before we list, not after the closing statement surprises them. If you want to see the full picture of what actually lands in your account, start with the seller net sheet and work backward from your sale price.

What happens to your Save Our Homes cap when you sell

For 20 years, the Save Our Homes cap held your assessed value down while market values ran. That protection does not travel with the house. When you sell, the home resets to market value for the next owner, which is why a buyer’s tax bill on your street can look nothing like yours.

The good news for a long tenure owner who is buying again in Florida is portability. You can move up to $500,000 of your accumulated Save Our Homes benefit to your next Florida homestead, which can cut the tax bill on the home you buy next by a meaningful amount. The steps are specific and the deadlines are firm.

1. Buy and establish your next Florida home as your primary residence, with residency in place by January 1.

2. File Form DR-501, the homestead application, and Form DR-501T, the transfer of your assessment difference, with your county property appraiser.

3. Watch both deadlines. The new homestead must be set up within three tax years of January 1 of the year you left the old one, and Form DR-501T is due March 1 of the tax year you first claim the new homestead, under section 193.155(8), Florida Statutes. Miss the window and the benefit is gone.

Weston sits in Broward County, so filing is free through the Broward County Property Appraiser. For a full walk through of how the transfer math works when the new home is worth more or less than the old one, read the guide on Save Our Homes portability.

How long will it take to sell a Weston home in 2026

The honest answer is that Weston takes longer to sell than it did, and it carries more selection than it used to. Weston single family homes moved at a median of 12 days on market in 2021, per my MLS pull. In the first half of 2026 the median was 40 days on market, per my MLS pull, close to the 42 day median of 2025. That is about six weeks from list to contract at the median for all Weston single family sales in the first half of 2026, and Weston held roughly 4.8 months of supply as of late July 2026, per my MLS pull, more inventory than a seller faced a few years ago.

More selection means the buyer has options, so your pricing has to be right from the first day on market. The right list price comes from current closed comps in your community, not from a portal estimate or what a neighbor “heard” a house went for. Pricing a home you have owned for 20 years is its own challenge, because your sense of value is anchored to a different decade and your emotional attachment is real. This is exactly the work I do before recommending a number, and it is where the difference between a clean sale and a stale listing gets decided.

Two more costs to plan into your net. Florida charges a documentary stamp tax on the deed, which the seller customarily pays in Broward, at the rate published by Broward County. Add your agent commission and your mortgage payoff if any remains, and the difference between your sale price and your walk away number becomes clear. If you are weighing the ongoing cost of staying against a move, the comparison in Davie versus Weston property taxes and carrying costs is a useful second read.

Frequently Asked Questions

Do I pay capital gains tax when I sell a Weston home I’ve owned 20 years?

Maybe, on the portion of your gain above the exclusion. Federal law lets a married couple filing jointly exclude up to $500,000 of gain and a single filer up to $250,000, if you owned and lived in the home two of the last five years, per the IRS, and whether your gain exceeds the $250,000 single or $500,000 married exclusion depends on your purchase price, your improvements, and your sale price. Any gain above your exclusion is taxed federally at up to 20 percent, plus the 3.8 percent net investment income tax for higher incomes, per IRS Topic 559. Florida charges no state income tax on the sale.

What happens to my Save Our Homes cap when I sell in Weston?

Your Save Our Homes cap does not transfer to the buyer. The home resets to market value for the next owner. If you buy another Florida home, you can port up to $500,000 of your accumulated Save Our Homes benefit to the new homestead, as long as you set up the new homestead within three tax years of January 1 of the year you left the old one and file Form DR-501T by March 1 of the year you claim it, under section 193.155(8), Florida Statutes.

How much have Weston home prices gone up since 2021?

Weston single family homes rose from a median sale price of $675,000 in 2021 to $915,000 in the first half of 2026, an increase of 35.6 percent, based on my own MLS closed sales pull. Average single family sale price rose even more, up 37.1 percent over the same period, per my MLS pull. For a home bought in 2006 near the last peak, the gain depends on that purchase price. In four 2025 Weston resales of homes bought in 2006, the sale price difference ran from $242,000 to $440,000, per Broward County Property Appraiser records pulled October 26, 2026.

How long does a Weston home take to sell right now?

Weston single family homes had a median of 40 days on market in the first half of 2026, per my MLS pull, close to the 42 day median in 2025 and well above the 12 day pace of 2021. Weston also carries more selection now, so correct pricing from current comps matters more than it did during the 2021 peak.

How much of my sale price do I actually keep?

Your net is your sale price minus your mortgage payoff, agent commission, the Florida documentary stamp tax on the deed, and a handful of closing line items. On a long held Weston home the equity can be substantial, but the capital gains question and the payoff determine your final number. Building a net sheet before you list is the only way to know it.

Talk to a Davie Real Estate Expert

Anthony Spitaleri is a Broker Associate with Coldwell Banker and a Davie native who tracks median sale prices, days on market, and sale to list ratios at the community level across Davie and Weston. Selling a home you have owned for 20 years brings a gain, a tax question, and a Save Our Homes decision that most sellers only see once, so it is worth mapping your specific numbers before you list rather than after. Schedule a free 15-minute strategy call and walk into your sale with your equity, your tax exposure, and your net all known.

Anthony Spitaleri

Living in Davie Florida

954-235-5783

Davie, Florida

livingindavieflorida.com

Written by Anthony Spitaleri, Broker Associate with Coldwell Banker and a Davie native. More about Anthony