Winter Park, FL — Momentum Score, Home Values & Best-For

All states·Florida·Winter Park

Orange County · Orlando-Kissimmee-Sanford · population 30,835

Renter-friendly
Winter Park, FL
Image: Wikipedia · Winter Park, Florida
OverviewCost of livingMoving guide
View watchlist →
60
Stable
Momentum score · 0–100

Where Winter Park stands

Steady, no major recent move.

Median home $465,527
1-year -1.5%
5-yr CAGR +5.7%
vs 5-yr peak -3.0%
Population +0.9%/yr

Home value trajectory · last 10 years

Zillow ZHVI · monthly
peak 2024-05$466k$218k$312k$405k$499k201620182020202220242026

Lifestyle scores

🚶
Walkability
32/100
Very car-dependent
Estimated from population density. Higher = denser, more amenities within walking distance.
🚉
Public transit
22/100
Transit limited
Curated list of major US transit systems + population-based estimate. Higher = real subway/rail/bus options.
💻
Remote work fit
92/100
Excellent for remote work
Composite of city size, housing cost, state tax structure, and region's remote-work track record.

Scores are heuristic estimates from population density, state, and known transit/walkable cities. Not based on a paid Walk Score / Transit Score API — see methodology for the formula.

Rent trajectory · last 5 years

Zillow ZORI · monthly
$1,845/mo$1,335$1,654$1,974202220242026

Home value vs rent · indexed to 100

Both rebased at first month of ZORI data (~2015)
Home valueRent132130100120140202220242026

Rent vs buy

Price-to-rent ratio: 21.0
Lean rent

At a 21.0 price-to-rent ratio, the math is starting to lean toward renting in Winter Park. Owner-occupier ROI requires longer holds and the assumption that prices keep appreciating roughly at the rate of rent.

How the momentum score breaks down

methodology →
Home YoY
42 · w22%
Home 5-yr CAGR
68 · w22%
Distance from peak
72 · w18%
Population growth
62 · w16%
Rent YoY
41 · w12%
Home 10-yr CAGR
75 · w10%
Long thesis

Winter Park has held up across the cycle: home values at $465,527 with +5.7% 5-year CAGR. The bull case is structural — population, location, employer base — and holds even if next year's print is soft.

Short thesis

Winter Park is in a state where home insurance costs have doubled, climate risk repricing is still in progress, and the buyer pool is constrained by both. The bear case writes itself and is currently winning.

About Winter Park

Winter Park is a city in Orange County, Florida, with an estimated population of 30,835. It anchors the Orlando-Kissimmee-Sanford metro area. The population grew 0.9% annually from 2020 to 2024, a moderate gain. The median home value in Winter Park is $465,527 as of 2026-04, down 1.5% over the last 12 months. Over the last five years, home values have averaged +5.7% annual growth (-3.0% from the 5-year peak). Rents in Winter Park average $1,845 per month, roughly flat year-over-year (-0.8%). The composite momentum score is 60 of 100 (Stable). Conditions are neither hot nor cold, so the local fit matters more than market timing.

▲ Bull case

●Healthy 5-year run: +5.7% annualized over 5 years, outpacing US inflation.
●Held the highs: currently -3.0% from the 5-year peak — this market refused to give back gains.

▼ Bear case

○Local nuance: city-level data smooths over neighborhood differences. School zones, HOA rules, and street-level character matter — visit before deciding.

About Winter Park (Wikipedia)

Winter Park is a city in Orange County, Florida, United States. The population was 29,795 at the 2020 census. It is part of the Orlando metropolitan area.

Source: Wikipedia · this summary is contributed and licensed under CC-BY-SA.

Playbook

Buyer

Lifestyle fit matters more than market timing in a Stable market. Take your time on the home and neighborhood; the macro trend isn't urgent. Negotiate normally.

Seller

Price competitively from day one or risk a 60+ day listing. Staging, photography, and presentation matter more in Stable markets than in Hot ones.

Investor

Stable cap rates, no big appreciation story to lean on. Underwrite this as a pure cash-flow play — the math has to work on rent alone.

Local safety & alerts

No active National Weather Service alerts for Orange County right now.

NWS active alerts (FL)Florida Emergency ManagementHow to prepare (NWS)

Public-safety links are official .gov sources, not curated by us. Orange County routes NWS alerts; check the state EM portal for non-weather emergencies.

Neighborhoods of Winter Park

1 tracked · ranked by median home value
1Goldenrod$379,298-3.6%

Cities like Winter Park

Oviedo, FL62 · RisingDeBary, FL62 · RisingCocoa, FL62 · RisingMaitland, FL59 · Stable

Run the numbers for Winter Park

ToolCan I afford Winter Park?Income → city shortlistToolROI on a Winter Park rentalCap rate, cash-on-cash, DSCRToolCompare Winter Park to anywhereSide-by-side up to 3 citiesToolWinter Park cost-of-livingEquivalent income elsewhere

Sources: Zillow ZHVI (home values), Zillow ZORI (rents), US Census ACS + place population. Updated when source agencies publish revisions.

Climate & natural-disaster risk

Winter (Jan)
70° / 51°
avg high / low
Summer (Jul)
90° / 73°
avg high / low
Sunny days/yr
233
~64% of year
Annual precip
54″ rain
0″ snow
Disaster risk (1=very low, 5=very high)
Hurricane
Very high
Tornado
Moderate
Wildfire
Low
Earthquake
Very low
Flood
Very high

State-level averages from NOAA Climate Normals (1991-2020) and FEMA National Risk Index. City-level conditions can vary significantly within a state.

Local sports teams

Major professional teams the Orlando-Kissimmee-Sanford area cheers for. Detailed stats, schedules, and player pages on intherafters.com.

Current weather

Loading current conditions…

7-day forecast on weather.gov →

Find rentals & listings

Open current Winter Park listings on the major real-estate sites.

Links open the live search on the destination site — results are always current.

Local news & community

Updated 2026-05-21 from Google News + Reddit RSS. Headlines link to original sources.

Local economy & environment

Humidity
76%
Very humid climate
Median household income
$67,900
Florida state median
Top industries (state-level)
TourismHealthcareConstruction

Humidity is annual average relative humidity (NOAA). Income is Census ACS 5-year estimate. Industries are largest employment sectors statewide (BLS); the local mix in a given city may vary.

Cities similar to Winter Park

Explore other places with comparable momentum or affordability.

See all Florida cities →    Browse best-of lists →