MLS data updated Jun 29, 2026
Four Seasons Condo
Established 1970 condo enclave off St. Andrews Blvd in Winter Park
Winter Park, FL
Four Seasons is an established 1970-built, low-rise condominium community set on roughly 20 landscaped acres off St. Andrews Boulevard in Winter Park, near the Cady Way Trail and Ward Park, with three pools, a tennis court, shuffleboard, and a clubhouse.
Median sold: $415K · Median days on market: 27 · Sold-to-list: 97.2% · Source: Stellar MLS
About 0 months of inventory — homes are selling faster than new ones come on the market, so sellers hold the leverage (under 4 months = seller's market).
Aggregate statistics from recent Stellar MLS closed sales and live MLS inventory. A market read, not an appraisal of any home or a listing of individual sales.
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Ryan's Take on Four Seasons Condo
Four Seasons Condominiums punches well above its size in the Winter Park market — it delivers one of Orange County's most sought-after school districts (Brookshire Elementary, Glenridge Middle, Winter Park High) wrapped inside a low-maintenance, walkable lifestyle that very few communities at this price point can match. The buyers I see here are typically right-sizing retirees, young professionals landing their first Winter Park address, and investors who understand that a 1970-built condo on 20 landscaped acres within the Winter Park city limits carries a different kind of staying power than newer product further out.
The commute anchor is real: Park Avenue is about five minutes away, Downtown Orlando is fifteen to twenty, and the Cady Way Trail runs right alongside the community for anyone who bikes or walks to work or play. That trail connectivity — plus the immediate walkability to Publix, Ward Park, and the YMCA — gives residents a quality of daily life that typically costs far more in this part of Central Florida.
What makes the housing stock distinctive is the low-rise, four-plex architecture, covered carport parking, and an HOA structure that bundles water, sewer, trash, pest control, and building insurance into the monthly fee. Buyers who cross-shop typically look at winter-park-pines condos further east or Dommerich Estates for single-family alternatives, but those options trade the all-inclusive HOA convenience and trail access that define the Four Seasons experience.
— Ryan Solberg, Broker/Owner, MaxLife Realty
Under Contract
2 homes pending in Four Seasons Condo · Avg. $200K
Four Seasons Condo · 2nd Quarter 2026
500 sales · Stellar MLS · last 12 mo
$415K
Median Sale Price
27 days
Median Days on Market
97.2%
Sold-to-List
$248
Median $/sqft
Recent Sales Map
60 recent individual sales in and around Four Seasons Condo · FL public records · no addresses published
Approximate sale locations — dots are offset ±1 home for privacy
| Beds | Baths | Sq Ft | Listed | Sold ▼ | List Price | Sold Price | $/Sq Ft | DOM |
|---|---|---|---|---|---|---|---|---|
| — | — | 3,858 | — | 12/1/25 | — | $935,000 | $242 | — |
| — | — | 2,059 | — | 12/1/25 | — | $770,000 | $374 | — |
| — | — | 1,419 | — | 12/1/25 | — | $675,000 | $476 | — |
| — | — | 2,256 | — | 12/1/25 | — | $605,000 | $268 | — |
| — | — | 1,370 | — | 12/1/25 | — | $530,000 | $387 | — |
| — | — | 2,225 | — | 12/1/25 | — | $479,000 | $215 | — |
| — | — | 1,125 | — | 12/1/25 | — | $470,000 | $418 | — |
| — | — | 1,738 | — | 12/1/25 | — | $455,000 | $262 | — |
| — | — | 1,677 | — | 12/1/25 | — | $450,000 | $268 | — |
| — | — | 1,364 | — | 12/1/25 | — | $450,000 | $330 | — |
| — | — | 1,829 | — | 12/1/25 | — | $450,000 | $246 | — |
| — | — | 1,785 | — | 12/1/25 | — | $440,000 | $246 | — |
| — | — | 1,578 | — | 12/1/25 | — | $420,000 | $266 | — |
| — | — | 1,050 | — | 12/1/25 | — | $418,000 | $398 | — |
| — | — | 1,382 | — | 12/1/25 | — | $415,000 | $300 | — |
| — | — | 1,200 | — | 12/1/25 | — | $395,000 | $329 | — |
| — | — | 1,200 | — | 12/1/25 | — | $375,000 | $313 | — |
| — | — | 1,530 | — | 12/1/25 | — | $365,000 | $239 | — |
| — | — | 1,214 | — | 12/1/25 | — | $350,000 | $288 | — |
| — | — | 1,821 | — | 12/1/25 | — | $343,000 | $188 | — |
| — | — | 1,676 | — | 12/1/25 | — | $340,000 | $203 | — |
| — | — | 1,221 | — | 12/1/25 | — | $315,000 | $258 | — |
| — | — | 1,415 | — | 12/1/25 | — | $245,000 | $173 | — |
| — | — | 1,281 | — | 12/1/25 | — | $205,000 | $160 | — |
| — | — | 1,219 | — | 12/1/25 | — | $205,000 | $168 | — |
| — | — | 987 | — | 12/1/25 | — | $200,000 | $203 | — |
| — | — | 1,151 | — | 12/1/25 | — | $199,000 | $173 | — |
| — | — | 1,120 | — | 12/1/25 | — | $195,000 | $174 | — |
| — | — | 1,049 | — | 12/1/25 | — | $138,000 | $132 | — |
| — | — | 796 | — | 12/1/25 | — | $127,000 | $160 | — |
| — | — | 1,605 | — | 12/1/25 | — | $110,000 | $69 | — |
| — | — | 4,560 | — | 11/1/25 | — | $1,500,000 | $329 | — |
| — | — | 2,455 | — | 11/1/25 | — | $899,000 | $366 | — |
| — | — | 2,498 | — | 11/1/25 | — | $764,000 | $306 | — |
| — | — | 2,111 | — | 11/1/25 | — | $750,000 | $355 | — |
| — | — | 1,829 | — | 11/1/25 | — | $699,500 | $382 | — |
| — | — | 2,256 | — | 11/1/25 | — | $660,000 | $293 | — |
| — | — | 1,772 | — | 11/1/25 | — | $545,000 | $308 | — |
| — | — | 2,124 | — | 11/1/25 | — | $528,000 | $249 | — |
| — | — | 1,277 | — | 11/1/25 | — | $500,000 | $392 | — |
| — | — | 2,427 | — | 11/1/25 | — | $469,500 | $193 | — |
| — | — | 1,978 | — | 11/1/25 | — | $460,000 | $233 | — |
| — | — | 1,929 | — | 11/1/25 | — | $350,000 | $181 | — |
| — | — | 1,320 | — | 11/1/25 | — | $330,000 | $250 | — |
| — | — | 1,004 | — | 11/1/25 | — | $290,000 | $289 | — |
| — | — | 1,018 | — | 11/1/25 | — | $180,000 | $177 | — |
| — | — | 1,393 | — | 11/1/25 | — | $177,000 | $127 | — |
| — | — | 763 | — | 11/1/25 | — | $140,000 | $183 | — |
| — | — | 727 | — | 11/1/25 | — | $130,000 | $179 | — |
| — | — | 1,085 | — | 11/1/25 | — | $100,000 | $92 | — |
| — | — | 4,644 | — | 10/1/25 | — | $1,422,800 | $306 | — |
| — | — | 2,759 | — | 10/1/25 | — | $850,000 | $308 | — |
| — | — | 2,372 | — | 10/1/25 | — | $700,000 | $295 | — |
| — | — | 1,456 | — | 10/1/25 | — | $515,000 | $354 | — |
| — | — | 1,508 | — | 10/1/25 | — | $490,000 | $325 | — |
| — | — | 1,564 | — | 10/1/25 | — | $480,000 | $307 | — |
| — | — | 2,015 | — | 10/1/25 | — | $455,500 | $226 | — |
| — | — | 1,623 | — | 10/1/25 | — | $450,000 | $277 | — |
| — | — | 1,469 | — | 10/1/25 | — | $425,000 | $289 | — |
| — | — | 818 | — | 10/1/25 | — | $401,000 | $490 | — |
Currently For Sale
2 active listings in Four Seasons Condo
$189/sqft
View details
$208/sqft
View details
| Beds | Baths | Sq Ft | List Price | $/Sq Ft | DOM |
|---|---|---|---|---|---|
| 2 | 2 | 1,219 | $229,900 | $189 | 1 |
| 1 | 1 | 793 | $164,999 | $208 | 1 |
Four Seasons Condo Market — Common Questions
Is Four Seasons Condo a buyer's or seller's market in 2026?+
Four Seasons Condo is currently a seller's market with about 0 months of inventory. About 0 months of inventory — homes are selling faster than new ones come on the market, so sellers hold the leverage (under 4 months = seller's market).
What is the median home sale price in Four Seasons Condo?+
Based on Florida Department of Revenue public records over the last 6 months, the median sale price in Four Seasons Condo is approximately $415K.
How many homes are for sale in Four Seasons Condo?+
There are currently 2 active listings in Four Seasons Condo, with homes selling at roughly 41.7 per month. That works out to about 0 months of inventory.
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Ryan Solberg
MaxLife Realty
321.373.3536
Report generated June 30, 2026 at 10:45 AM ET· Powered by Stellar MLS
MLS Data:Active and pending listing data is sourced from the Stellar MLS as distributed by MLS GRID. Listings courtesy of Stellar MLS as distributed by MLS GRID. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The MLS GRID does not guarantee the accuracy of this data, which may not reflect all real estate activity in the area.
Sold Data: Sales analysis is derived from Florida Department of Revenue public property records(arm's-length transactions). Ryan Solberg and MaxLife Realty LLC are not affiliated with Four Seasons Condoor its HOA. This report is not intended to solicit properties already listed for sale nor to cause a breach of an existing agency relationship. Data should be independently verified. E&OE.
Based on information submitted to the MLS GRID as of June 29, 2026 at 8:41 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of June 29, 2026 at 8:41 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
All or a portion of the multiple listing information is provided by Stellar MLS, from a copyrighted compilation of listings. The compilation of listings and each individual listing are © 2026 Stellar MLS. All rights reserved.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA