Luxury homes in Winter Park, Florida

Sell Your Winter Park Home.

One of Florida's highest price-per-square-foot markets. Getting it right requires knowing which streets carry the premium - and which ones don't.

Get Your Home ValueCall Us

Selling in Winter Park Requires Knowing Winter Park.

Winter Park trades on lifestyle as much as location. The Chain of Lakes, Park Avenue, the Morse Museum, brick streets, mature oak canopy, A-rated schools - buyers arrive with a specific picture in mind and pay significantly for homes that match it. The gap between the right presentation and a missed one is wider here than in any other Central Florida market.

Winter Park consistently achieves Central Florida's highest residential price-per-square-foot outside of Isleworth. The market is transparent and efficient - buyers and their agents are well-informed, which means overpricing is noticed immediately and punished with extended days on market.

NO LOCKBOXES! Sean or Barb Attends Every Single Showing

Most agents hand a buyer agent a lockbox code and hope for the best. Sean and Barb do not. Every showing of your home is attended in person by one of them. Not an assistant. Not a team member you have never met.

That means the person answering questions about your home is the person who priced it, marketed it, and will negotiate it. Buyer feedback reaches you the same day, not filtered through a third party a week later.

100%

Of showings attended in person. Always.

Estimate Your Net Proceeds.

Commission, title and closing costs, and loan payoffs, worked backward from your expected sale price so you can see what actually lands in your account.

Commission Rate
5.75% Average

Estimated Net
Proceeds

$788,375

Gross Sale$850,000
Fees & Costs$61,625
Loan Payoffs$0
Questions? Ask Sean and Barb

Estimate only. Commission assumed at 5.75%. Assumes 1.5% for title, closing, and prorations. It does not include repairs, concessions, HOA estoppel fees, or payoff interest. Sean or Barb will prepare a line-by-line seller net sheet for your address.

What Is Your Home Worth?

For the real number, request a complimentary valuation. Sean or Barb prepares a pricing analysis from your home, recent nearby sales, and current demand in your submarket, usually within one business day.

Thank you. Sean or Barb will be in touch shortly.

Central Florida Housing Stats

Median sold price, price per square foot, market pace, and months of supply for the 10 Central Florida markets we serve, updated monthly from Stellar MLS closed sales. Data through August 2026.

Winter Park Single Family Housing StatsAugust 2026 Stats

Choose a market

Median Sold Price, August 2026

$624,900
Jun-Aug Avg-
vs Jun-Aug 2025-

Median Price Per Sq Ft

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Closed in August

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Median Days on Market

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List Price vs. Sold Price %

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Half of August sales closed at or above this share of the final asking price

Months of Supply

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Active Listing Inventory vs Homes ClosedNov 2025 to Aug 2026
This Month's Listing ActivityAugust 2026
New Listings
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Competition that arrived this month
Pending
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Under contract now, closing in 30 to 45 days

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Source: Stellar MLS InfoSparks, single-family homes, August 2026. Based on information from the Stellar Multiple Listing Service. This information may or may not include all listed expired, withdrawn, pending or sold properties of one or more members of the Stellar Multiple Listing Service.

In August 2026 the median sold price for a single-family home in Winter Park was $624,900, with 63 homes closed, 16 median days on market and 98.2% of last list price. Data from Stellar MLS InfoSparks.

Reaching the Right Buyer Starts Here.

CaliforniaIllinoisNew YorkNew JerseyCentral Florida

Premier Sotheby's International Realty reaches qualified buyers through 1,100+ offices in 82 countries.

Winter Park attracts a mix of local move-up buyers, physicians from AdventHealth and Orlando Health systems, professionals relocating from major metros, and buyers specifically seeking the Park Avenue lifestyle. Many have researched the market extensively before their first showing.

Through Premier Sotheby's International Realty - 1,100+ offices, 82 countries - and targeted digital campaigns in the markets where Winter Park's buyer pool is relocating from, Sean & Barb ensure your home reaches the people most likely to buy it at the right price.

What the marketing plan includes

  • 01Professional photography and twilight sets
  • 02Cinematic drone fly-through
  • 03Sothebysrealty.com global syndication
  • 04Targeted paid social to relocating buyers
  • 05Print placement in Sotheby's channels
  • 06Broker and agent network outreach

Sean & Barb

With 60+ combined years in Central Florida, Sean & Barb work with luxury buyers and sellers, physicians relocating to the region, and the attorneys who refer estate and divorce property.

Sean Spencer, Global Real Estate Advisor

Sean Spencer

Licensed Locally 20+ Years

I've had the honor of working with physicians and executives relocating to Central Florida, helping them land quickly and confidently in communities that fit their lives. Honesty, discretion, and a genuine investment in your outcome - every time.

Barbara Vance, Global Real Estate Advisor

Barb Vance

Licensed Locally 40+ Years

With four decades of relationships across Central Florida's luxury communities, Barbara brings a depth of local knowledge that simply cannot be replicated. Her clients trust her not just for her expertise, but for her unwavering integrity.

60+

Combined Years

Hundreds of Happy Families

& counting

10

City Markets

What Winter Park Sellers Ask.

Winter Park seller questions
01

What makes Winter Park pricing different from other Central Florida markets?

Street-level variation is extreme. A home on a brick street with chain-of-lakes access trades at a fundamentally different multiple than a comparable on a standard interior street. Virginia Heights and the lake estates command significant premiums over market averages. Getting the comparable set right is critical - a general Winter Park median will often mislead in both directions.

Buying in Winter Park too? Browse Winter Park homes for sale and Winter Park waterfront homes. See every city on our selling your home page, or read our luxury home marketing plan.

Ready to List Your Winter Park Home?

Sean and Barb have closed transactions across Winter Park's most competitive streets. A listing consultation is a conversation - not a commitment.

Thank you. Sean or Barb will be in touch shortly.

Seba

Sean & Barb AI · Available 24/7

S
Hi! I'm Seba, the Sean & Barb AI assistant. I can answer questions about Central Florida luxury neighborhoods, market stats, physician relocation, and more. What's on your mind?

Calculate Your Mortgage

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%
%

Freddie Mac avg

Estimated Monthly

$0

P&I$0
Taxes$0
Insurance$0
Questions? Ask Sean and Barb

State Income Tax Calculator

What you keep by relocating to Florida

Estimated Annual Savings

$0

Florida has no state income tax

State income tax there$0
State income tax in Florida$0
Effective rate there0%
Kept over 10 years$0

Estimate of state income tax using current-year brackets at the income and filing status you enter. Where a city or locality is selected, its local income tax is included using physician-level approximate rates. Not tax advice. Florida levies no state or local income tax.

Explore Relocation InfoTalk to Sean & Barb

Seller Net Sheet

What you walk away with

Estimated Net Proceeds

$0

$850,000

Commission calculated at an average rate of 5.75%, including estimated closing costs.

After commission & closing costs$0
Less loan payoff- $0
Estimated net proceeds$0

Estimate only. Accuracy generally within a few hundred dollars. Does not factor in prorations or currently due HOA fees.

Request a ValuationTalk to Sean & Barb