The Winter Park Journal

Local insight. Better real estate decisions. Your resource for Winter Park living, luxury real estate, and buying and selling with confidence. Explore local insights, market trends, and practical answers to the questions that matter most when making your next move.

A Winter Park home with a cream stucco facade and terracotta roof after an afternoon rain, moss draped live oaks and reflective puddles in the foreground

Featured essay · Buying & Selling · November 3, 2026

Citizens Flood Coverage: What Winter Park Homeowners Should Know Before January 1

If your home is insured through Citizens, flood coverage becomes a condition of your wind policy on January 1, 2027. Here is who it applies to and what to do next.

Showing 17 of 17 essays

An elegant Winter Park home with cream stucco walls and a terracotta roof on a tree-lined street in warm autumn light

Selling & Pricing · November 2, 2026

Why Is My Winter Park Home Not Selling? What Days on Market Really Means

Winter Park homes sell in about 46 days now, and nearly three in ten listings carry a price cut. Here is what the market is actually telling sellers right now.

A stately cream stucco Winter Park home with a terracotta roof beneath live oaks draped in Spanish moss in late October light

Buying & Selling · October 29, 2026

The Fed Raised Rates in September: What It Means for Winter Park Buyers and Sellers

The Federal Reserve raised rates in September 2026 for the first time since 2023, and mortgage rates now sit near 7.3 percent. Here is what it means for Winter Park home values, pricing, and timing.

A Winter Park lakefront home with cream stucco walls and a private dock over still water under a partly cloudy sky

Buying & Selling · October 27, 2026

Flood Insurance and Your Winter Park Home: What the December 11 Deadline Means

Flood insurance rules are changing and the program's authority runs out December 11, 2026. What Winter Park buyers, sellers, and lakefront homeowners need to know.

A quiet brick-paved Winter Park street at golden hour, lined with live oaks and terracotta-roofed homes

Buying & Selling · October 26, 2026

Should You Wait for Mortgage Rates to Drop Before Buying in Winter Park?

Rates sit near 7.3 percent and the major forecasts expect them to stay there through 2027. Here is what Winter Park buyers should weigh before they wait.

A Mediterranean-style mid-rise condominium building on a calm Winter Park lake at sunrise

Buying & Selling · October 22, 2026

Florida's Condo Safety Law: What Winter Park Condo Owners Should Know

Special assessments, reserve studies, and the December 31 deadline. What Florida's condo safety law means for Winter Park condo buyers and sellers in 2026.

A quiet brick street in Winter Park lined with stately homes under live oaks with Spanish moss, in warm October light

Buying & Selling · October 20, 2026

Amendment 3: What Winter Park Homeowners Should Know About Florida's Property Tax Vote

Florida's Amendment 3 would raise the homestead exemption to $150,000, then $250,000. Here is what Winter Park homeowners would actually save, and what to know before you vote.

A stately Winter Park luxury home with cream stucco walls and a terracotta roof on an oak-lined street in late-afternoon light

Selling & Pricing · October 19, 2026

Is Now a Good Time to Sell Your Winter Park Home? What the Numbers Show

Orlando homes are sitting longer and price cuts are common, yet Winter Park sellers who price against today's competition are still getting strong results. Here is what the current data shows.

A signed real estate contract with a gold pen on an oak desk, a Winter Park home visible through the window

Buying & Selling · October 15, 2026

Who Pays the Buyer's Agent Now? What Winter Park Buyers and Sellers Should Know

The NAR settlement changed how buyer agent commissions are handled. Here is what the new rules mean for Winter Park buyers and sellers, and what to ask before you sign.

A Winter Park luxury home with cream stucco walls and a terracotta roof in warm golden-hour light

Selling & Pricing · October 13, 2026

Seller Concessions and Rate Buydowns: What Winter Park Sellers Should Know Right Now

Rates near 7.5 percent have buyers waiting. Here is how Winter Park sellers are using concessions and rate buydowns to get deals done, and what the loan rules allow.

A stately Winter Park luxury home with cream stucco walls and a terracotta roof in warm late-afternoon light

Buying & Selling · October 12, 2026

How Capital Gains Work When You Sell a Winter Park Home

Winter Park home values have grown fast. Here's what Florida sellers actually owe in capital gains tax, and what the federal exclusion covers.

A stately Winter Park home with cream stucco walls and a terracotta roof in warm late-afternoon light

Buying & Selling · October 12, 2026

Florida Homeowners Insurance: What Winter Park Homeowners Should Know Right Now

Citizens sent tens of thousands of non-renewal notices in September 2026. Here is what it means for Winter Park homeowners, how hurricane deductibles work, and what to do next.

A bright Florida entry hall with moving boxes and a potted plant beside an open door to a sunlit garden

Relocation · September 17, 2026

Moving to Winter Park from another state: what to know

Relocation is a bigger decision than a housing decision, which is why I treat it that way. Here is what out of state buyers should understand before they land.

A grand Spanish colonial revival home with cream stucco walls and a terracotta roof in early morning light

Selling & Pricing · September 17, 2026

How to price a luxury home when there are no good comparables

At the top of the Winter Park market, data runs out and judgment begins. Here is how I think about pricing a home with almost nothing to compare it to.

A calm Florida lake at sunrise with a wooden dock, a classic boat, and Spanish style homes across the water

Luxury Real Estate · September 17, 2026

What to know before buying a lakefront home in Winter Park

Lakefront is the most sought after address in Winter Park, and for good reason. Here is how to buy one well, from the view to the seawall.

Two wicker rocking chairs on a screened Florida porch with a lake glinting in the distance

Next Chapter · September 17, 2026

Right sizing: what comes after the kids leave?

The family home has a way of holding two generations at once. Letting go is an emotional decision first and a financial one second, and it deserves a guide who understands both.

A bright renovated Florida living room with white oak floors, linen curtains and warm neutral furniture in morning light

Strategy · September 17, 2026

Should I renovate my house or sell it?

The most common question I hear. The honest answer starts with what you are trying to accomplish over the next five to ten years, not with the kitchen.

A brick paved avenue in Winter Park lined with live oaks and boutique storefronts in soft morning light

Winter Park Living · September 17, 2026

What is it really like to live in Winter Park?

A small town with a world class cultural life, built around a chain of six lakes. Here is what living here actually feels like, from someone who has called it home for more than 35 years.

Not sure where to begin?

Start with the numbers

The market report

What the latest data says, and what to watch before you make a move.

Start with the streets

The neighborhood guides

Eight areas of Winter Park, from The Vias to Winter Park Pines.

Start with the question

Talk it through

Fifteen minutes with a local guide beats an hour of tabs.

Reading is useful. A conversation is better.