Winter Park Homes for Sale with a Pool
Homes with a private pool on the lot, from the MLS private-pool field. Community pools are not counted.
- For sale now
- 115
- Median list price
- $1.7M
- Median $ / sq ft
- $547
- Median days listed
- 65
Newest 24 of 115 pool homes in Winter Park
$6,900,000
1260 Alabama Dr
Winter Park, FL 32789
6 bd · 7 ba · 6,396 sqft
J Kronenberger Sub
MLS ID #O6387200, KELLY PRICE & COMPANY LLC.
Listing provided by Stellar MLS
$5,480,000
470 W Comstock Ave
Winter Park, FL 32789
6 bd · 7 ba · 6,134 sqft
Town Of Winter Park
MLS ID #W7890730, EQUITY PARTNERS REAL EST LLC.
Listing provided by Stellar MLS
$395,000
5409 Albert Dr
Winter Park, FL 32792
3 bd · 2 ba · 1,483 sqft
Howell Branch Woods
MLS ID #C7528794, SOVEREIGN REAL ESTATE GROUP.
Listing provided by Stellar MLS
$5,600,000
2228 Azalea Pl
Winter Park, FL 32789
5 bd · 6 ba · 5,152 sqft
Maitland Shores First Add
MLS ID #O6416342, COMPASS FLORIDA LLC.
Listing provided by Stellar MLS
$1,850,000
2507 Lafayette Ave
Winter Park, FL 32789
4 bd · 6 ba · 2,675 sqft
Winter Park Village
MLS ID #O6450302, ONE LUXURY INTERNATIONAL LLC.
Listing provided by Stellar MLS
$1,425,000
641 Northwood Circle
Winter Park, FL 32789
3 bd · 5 ba · 2,756 sqft
Winter Park Oasis
MLS ID #O6412554, PREMIER SOTHEBY'S INTL. REALTY.
Listing provided by Stellar MLS
$860,000
120 Longbranch Rd
Winter Park, FL 32792
5 bd · 4 ba · 3,284 sqft
Lake Ann Estates Unit 3
MLS ID #O6434232, OPENDOOR BROKERAGE LLC.
Listing provided by Stellar MLS
$1,699,999
647 Randy Ln
Winter Park, FL 32789
4 bd · 4 ba · 2,923 sqft
Timberlane
MLS ID #O6456258, SHAWFIELD REALTY GROUP.
Listing provided by Stellar MLS
$1,399,900
1737 Indiana Ave
Winter Park, FL 32789
4 bd · 4 ba · 2,984 sqft
Lawndale
MLS ID #S5158760, LOKATION.
Listing provided by Stellar MLS
$480,000
1735 Meadowgold Ln
Winter Park, FL 32792
3 bd · 2 ba · 1,768 sqft
Autumn Glen Ph 1
MLS ID #O6454832, RE/MAX TOWN & COUNTRY REALTY.
Listing provided by Stellar MLS
$599,000
4026 Tenita Dr
Winter Park, FL 32792
3 bd · 2 ba · 2,031 sqft
Lake Waunatta Wods
MLS ID #O6430278, RUBY DAVIS, BROKER.
Listing provided by Stellar MLS
$2,100,000
Winter Park, FL 32789
4 bd · 5 ba · 2,830 sqft
Lake Killarney Shores
MLS ID #O6456614, PLATINUM REALTY GROUP FLORIDA INC.
Listing provided by Stellar MLS
$875,000
618 Blairshire Cir
Winter Park, FL 32792
4 bd · 3 ba · 1,876 sqft
Brookshire Heights 4th Add
MLS ID #O6439298, REAL BROKER, LLC.
Listing provided by Stellar MLS
$629,500
640 N Park Ave #26
Winter Park, FL 32790
2 bd · 2 ba · 858 sqft
Park Aire Condo
MLS ID #O6456509, MICHAEL O'SHAUGHNESSY, INC..
Listing provided by Stellar MLS
$849,000
1507 Golfside Dr
Winter Park, FL 32792
3 bd · 2 ba · 2,003 sqft
Greenview At Winter Pines
MLS ID #S5160711, LPT REALTY, LLC.
Listing provided by Stellar MLS
$2,450,000
2718 Eastern Pkwy
Winter Park, FL 32789
4 bd · 5 ba · 3,308 sqft
Parklando
MLS ID #O6453504, KELLER WILLIAMS WINTER PARK.
Listing provided by Stellar MLS
$699,900
1884 Jessica Ct
Winter Park, FL 32789
3 bd · 2 ba · 1,666 sqft
Waterbridge
MLS ID #O6450978, RE/MAX 200 REALTY.
Listing provided by Stellar MLS
$6,795,000
901 Golfview Ter
Winter Park, FL 32789
5 bd · 6 ba · 5,479 sqft
Golfview Terrace
MLS ID #O6437917, PREMIER SOTHEBY'S INTL. REALTY.
Listing provided by Stellar MLS
$1,675,000
2343 Versailles Ave
Winter Park, FL 32789
4 bd · 4 ba · 3,307 sqft
Fontainebleau
MLS ID #O6432029, FANNIE HILLMAN & ASSOCIATES.
Listing provided by Stellar MLS
$1,800,000
281 Brewer Ave
Winter Park, FL 32789
5 bd · 5 ba · 4,029 sqft
Osceola Shores Sec 02
MLS ID #O6424364, HENTHORN REAL ESTATE.
Listing provided by Stellar MLS
$695,000
715 S Ranger Blvd
Winter Park, FL 32792
4 bd · 3 ba · 2,312 sqft
Winter Park Pines
MLS ID #O6410899, DAHLIA REALTY GROUP.
Listing provided by Stellar MLS
$5,995,000
698 N New York Ave
Winter Park, FL 32789
5 bd · 6 ba · 5,096 sqft
Greens/Pk
MLS ID #O6439388, PREMIER SOTHEBY'S INTL. REALTY.
Listing provided by Stellar MLS
$3,195,000
1825 Whitehall Dr
Winter Park, FL 32789
4 bd · 6 ba · 4,311 sqft
Kenilworth Shores Sec 06
MLS ID #O6450811, COMPASS FLORIDA LLC.
Listing provided by Stellar MLS
$520,000
1905 Bonanza Ct
Winter Park, FL 32792
4 bd · 2 ba · 1,774 sqft
Eastbrook Sub Unit 13
MLS ID #O6433122, ORCHARD BROKERAGE, LLC.
Listing provided by Stellar MLS
Search all Winter Park listings on the map →
Winter Park pool homes by price
- Under $300K5
- $300K–$500K14
- $500K–$750K16
- $750K–$1M8
- $1M+72
Neighborhoods with the most pool homes for sale
- Kenilworth Shores6 listed
- Eastbrook Sub4 listed
- Winter Park Estates4 listed
- The Enclave Winter Park4 listed
- J Kronenberger Sub3 listed
- Lawndale3 listed
- Winter Park Pines3 listed
- Comstock Park3 listed
- Lake Knowles Terrace3 listed
- Forest Hills3 listed
Winter Park pool homes: quick answers
How many pool homes are for sale in Winter Park?+
115 pool homes are listed for sale in Winter Park, FL right now, 7 of them new in the last 7 days. Homes with a private pool on the lot, from the MLS private-pool field. Community pools are not counted.
What do pool homes cost in Winter Park?+
The median list price is $1.7M (about $547 per square foot), with listings from $183K to $6.9M.
How long do pool homes in Winter Park stay on the market?+
The listings for sale now have been on the market a median of 65 days.
Which Winter Park neighborhoods have the most pool homes for sale?+
Kenilworth Shores (6), Eastbrook Sub (4), Winter Park Estates (4), The Enclave Winter Park (4), J Kronenberger Sub (3).
More Winter Park homes for sale
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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 November 13, 2026 at 12:15 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