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Winter Park, FL Real Estate Guide

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Winter Park Market Snapshot

Every figure below is computed from closed MLS transactions in Winter Park over the trailing twelve months — what buyers and tenants actually paid, not asking prices — and refreshes continuously.

928
Homes sold, last 12 months
$493K
Median sale price
$298
Median price per sqft
27 days
Median time on market
464
Leases signed, last 12 months
$2,398/mo
Median rent achieved
$2
Median rent per sqft
34 days
Median time to lease
Homes Sold per Month
85Sep88Oct64Nov78Dec56Jan66Feb85Mar67Apr86May116Jun102Jul14Aug
Median Sale Price per Month
$567K$440KSepOctNovDecJanFebMarAprMayJunJulAug
Median Sale Price by Bedrooms
BedroomsSalesMedian price
1 bd47$158,000
2 bd172$255,000
3 bd375$459,000
4 bd234$757,500
5+ bd100$1,850,000
Sales by Property Type
TypeSalesMedian price
Single Family Residence662$625,000
Condominium179$194,995
Townhouse76$340,000
1/2 Duplex9$300,000
Villa2$288,950
12-Month Sales Trend
MonthHomes soldMedian price
Sep 202585$510,000
Oct 202588$506,000
Nov 202564$524,000
Dec 202578$474,500
Jan 202656$480,000
Feb 202666$455,000
Mar 202685$468,000
Apr 202667$490,000
May 202686$500,000
Jun 2026116$511,750
Jul 2026102$566,500
Aug 202614$439,500
Median Rent by Bedrooms
BedroomsLeasesMedian rent
Studio5$1,100/mo
1 bd30$1,350/mo
2 bd139$1,725/mo
3 bd200$2,600/mo
4 bd78$3,900/mo
5+ bd12$6,250/mo

Buying a Home in Winter Park

A smart Winter Park purchase begins with knowing what moves its market. Use the bedroom and property-type tables above to benchmark the segment you're shopping, then open the live map search to see what's on the market right now — every listing links through to full photos, details and a direct line to a licensed Florida broker.

In Florida, a financed purchase generally closes in 30 to 45 days, while an all-cash deal can wrap in as little as two weeks. A condo adds a board-approval step, and anything near the water carries insurance questions worth pricing before you write an offer — both are routine parts of a Winter Park transaction when you plan for them early.

Renting in Winter Park

Rentals turn over faster than sales — a well-priced Winter Park unit is often under lease within weeks, and most annual leases ask for first month, last month and a security deposit up front. The rent tables above show what tenants actually committed to by bedroom count over the past year, and the live rental search lists every home and condo on offer today.

Featured Listings in Winter Park

See every home for sale →
1120 PRESERVE POINT DRIVE, WINTER PARK, FL 32789
$8,950,000
7 bd · 11 ba · 11,255 sqft
1120 PRESERVE POINT DRIVE, WINTER PARK, FL 32789
40 PALMER AVENUE, WINTER PARK, FL 32789
$7,250,000
5 bd · 6 ba · 5,905 sqft
40 PALMER AVENUE, WINTER PARK, FL 32789
1260 ALABAMA DRIVE, WINTER PARK, FL 32789
$6,900,000
6 bd · 7 ba · 6,396 sqft
1260 ALABAMA DRIVE, WINTER PARK, FL 32789
1571 WOODLAND AVENUE, WINTER PARK, FL 32789
$6,000,000
5 bd · 8 ba · 7,397 sqft
1571 WOODLAND AVENUE, WINTER PARK, FL 32789
2228 AZALEA PLACE, WINTER PARK, FL 32789
$5,600,000
5 bd · 6 ba · 5,152 sqft
2228 AZALEA PLACE, WINTER PARK, FL 32789
313 SYLVAN DRIVE, WINTER PARK, FL 32789
$5,500,000
4 bd · 5 ba · 4,775 sqft
313 SYLVAN DRIVE, WINTER PARK, FL 32789

Winter Park Real Estate FAQ

Is Winter Park a good place to buy a home?

Let the figures on this page make the case for Winter Park — real closed sales, the median sale price, and how long homes sat before selling over the trailing twelve months.

What is the median home price in Winter Park?

The snapshot above reports the current 12-month median sale price for Winter Park, together with price per square foot and medians split out by bedroom count and property type. Every figure is calculated from closed MLS sales and refreshed continuously — not lifted from a report that's already months old.

Condo or house in Winter Park — which should I buy?

The property-type table above breaks Winter Park sales into condos, single-family homes and townhomes, and shows where each segment's median landed over the past year. A condo brings monthly association dues and a board-approval step; a house carries its own insurance and upkeep. Each property type has its own live search page linked below.

Where can I see every home for sale in Winter Park?

Open the Winter Park map search — it shows every active MLS listing in the city, updated continuously, with the city boundary traced on the map and filters for property type, bedrooms and price.

Discover Your Perfect Home

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Bedroom Size Homes in Winter Park
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Lifestyle & New in Winter Park
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