MLS data updated Jun 29, 2026
Winter Park Pines
Established 1960s ranch homes near Cady Way Trail and Winter Pines Golf
Winter Park, FL
Winter Park Pines is an established single-family community in Winter Park, FL, off Aloma Avenue near Ward Park, featuring 1960s-era Florida ranch homes on larger lots with mature trees, steps from the Cady Way Trail and the adjacent Winter Pines Golf Club.
Median sold: $456K · Median days on market: 23 · Sold-to-list: 97.7% · Source: Stellar MLS
About 0.5 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 Winter Park Pines
Winter Park Pines draws buyers who have done the research: families prioritizing Winter Park High School's IB program, dual-income professionals wanting a genuine Winter Park address, and move-up buyers from east Orlando who want real lot sizes and mature trees rather than master-planned sameness.
The commute anchor here is genuine versatility. Residents reach AdventHealth Winter Park in roughly 7 minutes, the UCF Research Park corridor in 20-25 via Aloma Avenue, and downtown Orlando in under 30 — without the daily I-4 commitment that other Winter Park-adjacent neighborhoods require. That geographic crossroads is what keeps demand steady across market cycles.
What makes the housing stock distinctive is what's absent: no mandatory HOA, no covenant micromanagement, and no builder-imposed uniformity. The concrete-block ranch homes from the 1960s through the 1980s sit on larger-than-typical lots, most with screened pools and established landscaping. The Cady Way Trail runs through the area connecting to schools and parks, and the Winter Park Pines Golf Club sits on the community's southern boundary — an unusually complete lifestyle package for an in-town address.
Buyers cross-shopping here typically compare Kenilworth Shores for a similar established-ranch feel, or look west toward Winter Garden when square footage per dollar becomes the deciding factor.
— Ryan Solberg, Broker/Owner, MaxLife Realty
Under Contract
7 homes pending in Winter Park Pines · Avg. $623K
Winter Park Pines · 2nd Quarter 2026
405 sales · Stellar MLS · last 12 mo
$456K
Median Sale Price
23 days
Median Days on Market
97.7%
Sold-to-List
$266
Median $/sqft
Recent Sales Map
60 recent individual sales in and around Winter Park Pines · 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 | — |
| — | — | 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 | — |
| — | — | 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 | — |
| — | — | 1,458 | — | 10/1/25 | — | $370,000 | $254 | — |
| — | — | 1,526 | — | 10/1/25 | — | $345,000 | $226 | — |
| — | — | 1,765 | — | 9/1/25 | — | $750,000 | $425 | — |
| — | — | 2,347 | — | 9/1/25 | — | $715,000 | $305 | — |
| — | — | 1,634 | — | 9/1/25 | — | $655,000 | $401 | — |
| — | — | 2,003 | — | 9/1/25 | — | $610,000 | $305 | — |
| — | — | 1,151 | — | 9/1/25 | — | $570,000 | $495 | — |
| — | — | 1,384 | — | 9/1/25 | — | $570,000 | $412 | — |
| — | — | 1,699 | — | 9/1/25 | — | $545,000 | $321 | — |
| — | — | 1,656 | — | 9/1/25 | — | $510,000 | $308 | — |
| — | — | 1,906 | — | 9/1/25 | — | $475,000 | $249 | — |
| — | — | 1,631 | — | 9/1/25 | — | $465,000 | $285 | — |
| — | — | 1,182 | — | 9/1/25 | — | $399,900 | $338 | — |
| — | — | 1,558 | — | 9/1/25 | — | $385,000 | $247 | — |
| — | — | 1,570 | — | 9/1/25 | — | $379,000 | $241 | — |
Currently For Sale
16 active listings in Winter Park Pines
$389/sqft
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$343/sqft
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$413/sqft
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$397/sqft
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$323/sqft
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$319/sqft
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$347/sqft
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$297/sqft
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$267/sqft
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$346/sqft
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$346/sqft
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$423/sqft
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| Beds | Baths | Sq Ft | List Price | $/Sq Ft | DOM | Pool |
|---|---|---|---|---|---|---|
| 3 | 3 | 1,539 | $598,000 | $389 | 295 | ✓ |
| 4 | 2 | 1,968 | $675,000 | $343 | 229 | — |
| 3 | 2 | 1,560 | $645,000 | $413 | 3 | — |
| 4 | 3 | 1,950 | $775,000 | $397 | 5 | ✓ |
| 3 | 2 | 1,656 | $535,000 | $323 | 14 | — |
| 3 | 2 | 1,565 | $498,900 | $319 | 18 | — |
| 3 | 2 | 1,570 | $544,900 | $347 | 134 | — |
| 4 | 2 | 1,596 | $474,000 | $297 | 28 | — |
| 3 | 2 | 1,196 | $319,900 | $267 | 0 | — |
| 4 | 2 | 1,876 | $649,000 | $346 | 7 | — |
| 3 | 2 | 1,785 | $617,500 | $346 | 103 | ✓ |
| 3 | 3 | 1,680 | $710,000 | $423 | 74 | — |
| 4 | 3 | 2,312 | $695,000 | $301 | 2 | ✓ |
| 4 | 2 | 1,651 | $450,000 | $273 | 1 | — |
| 3 | 2 | 1,592 | $475,000 | $298 | 245 | — |
| 5 | 3 | 2,194 | $800,000 | $365 | 12 | ✓ |
Winter Park Pines Market — Common Questions
Is Winter Park Pines a buyer's or seller's market in 2026?+
Winter Park Pines is currently a seller's market with about 0.5 months of inventory. About 0.5 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 Winter Park Pines?+
Based on Florida Department of Revenue public records over the last 6 months, the median sale price in Winter Park Pines is approximately $456K, down about 5.1% from a year earlier.
How many homes are for sale in Winter Park Pines?+
There are currently 16 active listings in Winter Park Pines, with homes selling at roughly 33.8 per month. That works out to about 0.5 months of inventory.
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Ryan Solberg
MaxLife Realty
321.373.3536
Report generated June 29, 2026 at 7:24 PM 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 Winter Park Pinesor 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 4:27 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 4:27 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