Bainbridge Winter Park
Morgan Stanley Ave, near the Winter Park SunRail/Amtrak station · $1,605-$2,999
✓ Modern mid-rise construction (5 stories) with elevator access and a resident parking garage
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Apartments With Pools in Winter Park, FL
11 matching communities · Winter Park, FL · Compare listed amenities and confirm current details with each property.
Compare communities whose checked public amenity lists include a pool in Winter Park. Open a profile to see the property information available in our records and any retained source links.
As of mid-2026 public listings, 1BR rents run roughly $1,650-$2,500+ near downtown/Winter Park Village and the Fairview area close to Park Avenue, while 1BR units along the Goldenrod Road/University Boulevard corridor and Seminole County-line neighborhoods typically start around $1,200-$1,700. Apartments.com lists the citywide average 1BR rent near $1,490/month, up roughly 2% year-over-year.
Calibre Bend Apartments
East Winter Park, Calibre Bend Ln near University Square · $1,499-$2,018
✓ Above-average review volume (20 reviews) with a solidly 'Good' blended rating
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Central Place At Winter Park
East Winter Park, University Blvd near Goldenrod Rd · $1,215-$1,815
✓ Among the most affordable options in the Winter Park zip codes, with 1BR rents starting near $1,200
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Cranes Landing Apartments
East Winter Park, N Goldenrod Rd near Full Sail University · $1,160-$2,026
✓ Large, established community (250+ units) with frequent move-in specials
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Elon Winter Park
Fairview, Nicolet Ave near Park Avenue · $1,674-$1,708
✓ Boutique scale (under 100 units) in a walkable Fairview location close to Park Avenue's shops and galleries
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Liv at Winter Park Apartment Homes
East Winter Park, N Goldenrod Rd, lakeside · $1,281-$3,452
✓ Lakeside setting with a private beach area, hammocks, and free kayak/paddleboard rental — a distinctive amenity for the price tier
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Oak Reserve at Winter Park
East Winter Park, Oak Reserve Ln off University Blvd · $1,425-$2,025
✓ Competitive pricing relative to newer Winter Park communities
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Paseo at Winter Park Village
Winter Park Village, W Canton Ave · $2,026-$3,498
✓ Walking distance to Winter Park Village's shops, restaurants, and movie theater
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Sapphire Winter Park
Lake Howell area, near the Winter Park/Seminole County line · $1,199-$1,699
✓ Spans a spacious, wooded 26-acre property with a resident pool and outdoor grill area
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Seven41 Winter Park
Fairview, Clay St near downtown Winter Park · $1,585-$2,295
✓ One of the newest properties in the market (built 2021)
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Vintage Winter Park Apartments
East Winter Park, off N Goldenrod Rd near University Blvd · $1,919-$2,830
✓ Consistently rated among the highest-reviewed properties in this roundup, with hundreds of resident reviews trending strongly positive
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How this apartment research is made
How we build these pages: we examine publicly available resident feedback from sources such as Google, ApartmentRatings, Yelp and Reddit, then summarize recurring themes in our own words. We don't copy review text or display third-party star ratings. Paid partner modules are labeled and do not alter the editorial summary. Trade-offs reflect what residents report — experiences vary. Rent ranges come from public listings and change often; always confirm current pricing, fees and policies with the property directly.