Call us at (888) 625-4885 to learn more about active adult communities near Winter Park
Winter Park, FL 55+ active adult communities & homes for sale
90 communities near Winter Park
2,487 homes near Winter Park
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4 rating (17 reviews)
![The Villages®]()
<$100k
- $1Ms
The Villages®, The Villages, FL
New and Resale
|
55+ age-restricted
|
Built 1978 - present
|
70,000 homes
4.7 rating (18 reviews)
![Solivita]()
$100Ks
- $600Ks
Solivita, Kissimmee, FL
New and Resale
|
55+ age-restricted
|
Built 2000 - present
|
5,900 homes
3.6 rating (48 reviews)
![Latitude Margaritaville]()
$300Ks
- $900Ks
Latitude Margaritaville, Daytona Beach, FL
Resale Only
|
55+ age-restricted
|
Built 2017 - 2025
|
3,900 homes
5 rating (1 reviews)
![Plantation Bay Golf &...]()
$200Ks
- $4Ms
Plantation Bay Golf &..., Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1988 - present
|
3,500 homes
4.5 rating (11 reviews)
![Spruce Creek Country Club]()
$200Ks
- $500Ks
Spruce Creek Country Club, Summerfield, FL
Resale Only
|
55+ age-restricted
|
Built 1996 - 2007
|
3,250 homes
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5 rating (2 reviews)
![Plantation at Leesburg]()
$100Ks
- $500Ks
Plantation at Leesburg, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1987 - 2008
|
2,820 homes
5 rating (3 reviews)
![Stonecrest]()
$200Ks
- $500Ks
Stonecrest, Summerfield, FL
New and Resale
|
55+ age-restricted
|
Built 1990 - present
|
2,200 homes
5 rating (7 reviews)
![Kings Ridge]()
$200Ks
- $400Ks
Kings Ridge, Clermont, FL
Resale Only
|
55+ age-restricted
|
Built 1995 - 2000
|
2,088 homes
5 rating (3 reviews)
![Twin Lakes]()
$200Ks
- $600Ks
Twin Lakes, St. Cloud, FL
New and Resale
|
55+ age-restricted
|
Built 2016 - present
|
2,000 homes
$300Ks
- $1Ms
Grand Haven, Palm Coast, FL
New and Resale
|
Age-targeted
|
Built 1997 - present
|
1,901 homes
Download the Ultimate 55+ Homebuying Guide
Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
$100Ks
- $500Ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only
|
Age-targeted
|
Built 1980 - 2006
|
1,806 homes
4.7 rating (3 reviews)
![Spruce Creek South]()
$100Ks
- $300Ks
Spruce Creek South, Summerfield, FL
Resale Only
|
55+ age-restricted
|
Built 1989 - 1995
|
1,650 homes
5 rating (1 reviews)
![Cypress Lakes]()
$100Ks
- $200Ks
Cypress Lakes, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1987 - 2016
|
1,604 homes
5 rating (3 reviews)
![Lake Ashton]()
$200Ks
- $800Ks
Lake Ashton, Lake Wales, FL
Resale Only
|
55+ age-restricted
|
Built 2002 - present
|
1,600 homes
$200Ks
- $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale
|
Age-targeted
|
Built 2004 - present
|
1,561 homes
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5 rating (2 reviews)
![Heritage Isle]()
$200Ks
- $500Ks
Heritage Isle, Viera, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2017
|
1,500 homes
3.8 rating (6 reviews)
![Trilogy® Orlando]()
$200Ks
- $500Ks
Trilogy® Orlando, Groveland, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2022
|
1,500 homes
5 rating (8 reviews)
![Royal Highlands]()
$200Ks
- $500Ks
Royal Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2006
|
1,500 homes
5 rating (1 reviews)
![Del Webb Sunbridge]()
$300Ks
- $1Ms
Del Webb Sunbridge, St. Cloud, FL
New and Resale
|
55+ age-restricted
|
Built 2019 - present
|
1,300 homes
5 rating (1 reviews)
![VillageWalk at Lake Nona]()
$300Ks
- $1Ms
VillageWalk at Lake Nona, Orlando, FL
Resale Only
|
Age-targeted
|
Built 2006 - 2016
|
1,300 homes
Download the Ultimate 55+ Homebuying Guide
Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
$300Ks
- $800Ks
Del Webb at Viera, Melbourne, FL
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
1,300 homes
5 rating (8 reviews)
![Pennbrooke Fairways]()
<$100k
- $300Ks
Pennbrooke Fairways, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1980 - 2004
|
1,200 homes
5 rating (1 reviews)
![Sandpiper Golf & Coun...]()
$200Ks
- $400Ks
Sandpiper Golf & Coun..., Lakeland, FL
New and Resale
|
55+ age-restricted
|
Built 1985 - present
|
1,193 homes
3.6 rating (5 reviews)
![Heritage Hills]()
$200Ks
- $500Ks
Heritage Hills, Clermont, FL
New and Resale
|
55+ age-restricted
|
Built 2006 - present
|
1,154 homes
5 rating (1 reviews)
![Cresswind at Victoria Gar...]()
$300Ks
- $600Ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only
|
55+ age-restricted
|
Built 2001 - 2022
|
1,070 homes
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$200Ks
- $700Ks
Halifax Plantation, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1980 - present
|
1,000 homes
5 rating (1 reviews)
![Legacy of Leesburg]()
$200Ks
- $400Ks
Legacy of Leesburg, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2017
|
1,000 homes
$400Ks
- $700Ks
Breakaway Trails, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1985 - present
|
976 homes
4 rating (4 reviews)
![Lakes of Mount Dora]()
$400Ks
- $900Ks
Lakes of Mount Dora, Mount Dora, FL
New and Resale
|
55+ age-restricted
|
Built 2006 - present
|
950 homes
4 rating (2 reviews)
![Harbor Hills Country Club]()
$200Ks
- $1Ms
Harbor Hills Country Club, Lady Lake, FL
New and Resale
|
Age-targeted
|
Built 1989 - present
|
940 homes
Download the Ultimate 55+ Homebuying Guide
Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
4.8 rating (6 reviews)
![Highland Lakes]()
$100Ks
- $300Ks
Highland Lakes, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1990 - 1999
|
938 homes
4.4 rating (16 reviews)
![Del Webb Orlando]()
$300Ks
- $400Ks
Del Webb Orlando, Davenport, FL
Resale Only
|
55+ age-restricted
|
Built 2007 - 2021
|
937 homes
5 rating (2 reviews)
![Bridgewater at Viera]()
$300Ks
- $600Ks
Bridgewater at Viera, Melbourne, FL
Resale Only
|
55+ age-restricted
|
Built 2017 - 2023
|
870 homes
$200Ks
- $1Ms
The Country Club of Mount..., Mount Dora, FL
Resale Only
|
Age-targeted
|
Built 1991 - 2005
|
827 homes
4.1 rating (9 reviews)
![Indian River Colony Club]()
$200Ks
- $400Ks
Indian River Colony Club, Melbourne, FL
New and Resale
|
55+ age-restricted
|
Built 1986 - present
|
777 homes
Want to learn more about 55+ communities in Winter Park?
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3.9 rating (7 reviews)
![Summit Greens]()
$300Ks
- $400Ks
Summit Greens, Clermont, FL
Resale Only
|
55+ age-restricted
|
Built 2001 - 2019
|
769 homes
5 rating (1 reviews)
![Royal Harbor]()
$200Ks
- $400Ks
Royal Harbor, Tavares, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2008
|
755 homes
$200Ks
- $500Ks
Lakeside Landings, Oxford, FL
New and Resale
|
Age-targeted
|
Built 2005 - present
|
700 homes
1 rating (1 reviews)
![Sullivan Ranch]()
$300Ks
- $600Ks
Sullivan Ranch, Mount Dora, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2020
|
692 homes
The Villages®
![523 BONITA DR, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,332 sq ft
|Manufactured Home
523 BONITA DR, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5099329 • KELLER WILLIAMS CORNERSTONE RE, Ka...
The Villages®
![825 ULELAH ST, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|2,096 sq ft
|House
825 ULELAH ST, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5102591 • REALTY EXECUTIVES IN THE VILLAGES,...
The Villages®
![1605 CHAVEZ CT, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,638 sq ft
|House
1605 CHAVEZ CT, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5099171 • BROKER ASSOCIATES REALTY, Kim Asch...
The Villages®
![1722 BUGLE TER, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,667 sq ft
|House
1722 BUGLE TER, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5098901 • COLDWELL BANKER VANGUARD LIFESTYLE...
The Villages®
![917 RAMOS DR, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
3 beds
|2 baths
|2,082 sq ft
|House
917 RAMOS DR, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5098937 • BROKER ASSOCIATES REALTY, Kim Asch...
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(888) 625-4885
The Villages®
![4878 CHITTY CHATTY RUN, THE VILLAGES, FL..., The Villages, FL 32163]()
4 beds
|3 baths
|2,296 sq ft
|House
4878 CHITTY CHATTY RUN, THE VILLAGES, FL...
Community: The Villages®
MLS G5097795 • REALTY EXECUTIVES IN THE VILLAGES,...
The Villages®
![5868 WOOD STORK WAY, THE VILLAGES, FL, 3..., The Villages, FL 32163]()
3 beds
|2 baths
|2,016 sq ft
|House
5868 WOOD STORK WAY, THE VILLAGES, FL, 3...
Community: The Villages®
MLS G5097909 • EXP REALTY LLC, Lili Whittington
New
Stonecrest
![16896 SE 110TH COURT RD, SUMMERFIELD, FL..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,951 sq ft
|House
16896 SE 110TH COURT RD, SUMMERFIELD, FL...
Community: Stonecrest
MLS G5103513 • RE/MAX PREMIER REALTY LADY LK, Cin...
The Villages®
![1562 HANCOCK ST, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,123 sq ft
|House
1562 HANCOCK ST, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5104264 • KELLER WILLIAMS CORNERSTONE RE, Wi...
New
Del Webb Minneola
![1393 ZESTY CITRUS LN, MINNEOLA, FL, 3471..., Minneola, FL 34715]()
4 beds
|4 baths
|3,108 sq ft
|House
1393 ZESTY CITRUS LN, MINNEOLA, FL, 3471...
Community: Del Webb Minneola
MLS O6362906 • PULTE REALTY OF NORTH FLORIDA LLC,...
Download the Ultimate 55+ Homebuying Guide
Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Highland Fairways
![3650 WILDCAT RUN, LAKELAND, FL, 33810, Lakeland, FL 33810]()
3 beds
|3 baths
|1,879 sq ft
|House
3650 WILDCAT RUN, LAKELAND, FL, 33810
Community: Highland Fairways
MLS L4957098 • LPT REALTY, LLC, Carri McLure
The Villages®
![5967 FREITAG AVE, THE VILLAGES, FL, 3216..., The Villages, FL 32163]()
3 beds
|2 baths
|1,633 sq ft
|Villa
5967 FREITAG AVE, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS OM713538 • SALLY LOVE REAL ESTATE, Star Amado...
New
The Villages®
![1016 PICKERING PATH, THE VILLAGES, FL, 3..., The Villages, FL 32163]()
3 beds
|2 baths
|2,230 sq ft
|House
1016 PICKERING PATH, THE VILLAGES, FL, 3...
Community: The Villages®
MLS G5104870 • REALTY EXECUTIVES IN THE VILLAGES,...
Del Webb Orlando
![208 ALMERIA WAY, DAVENPORT, FL, 33837, Davenport, FL 33837]()
2 beds
|2 baths
|1,927 sq ft
|House
208 ALMERIA WAY, DAVENPORT, FL, 33837
Community: Del Webb Orlando
MLS S5120376 • RIDGE REALTY GROUP LLC, Stephen Ne...
New
Venetian Bay
![3328 MARSILI AVE, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
3 beds
|2 baths
|1,423 sq ft
|House
3328 MARSILI AVE, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS FC314384 • KELLER WILLIAMS RLTY FL. PARTN, BJ...
Want to learn more about 55+ communities in Winter Park?
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Questions? Call us:
(888) 625-4885
The Villages®
![5562 LANSING DR, WILDWOOD, FL, 34785, Wildwood, FL 34785]()
2 beds
|2 baths
|784 sq ft
|Mobile Home
5562 LANSING DR, WILDWOOD, FL, 34785
Community: The Villages®
MLS S5135339 • ONE TEAM REALTY, Jesus Villegas Ne...
New
Solivita
![779 VIA COMO ST, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5139075 • PELLEGO, LLC, Stan Wilson
The Villages®
![17773 SE 91ST FREEDOM CT, THE VILLAGES, ..., The Villages, FL 32162]()
2 beds
|2 baths
|1,165 sq ft
|Villa
17773 SE 91ST FREEDOM CT, THE VILLAGES, ...
Community: The Villages®
MLS G5103545 • REALTY EXECUTIVES IN THE VILLAGES,...
The Villages®
![1822 ATHENS LN, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,322 sq ft
|Villa
1822 ATHENS LN, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5103523 • REALTY EXECUTIVES IN THE VILLAGES,...
The Villages®
![859 KLINE ST, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,861 sq ft
|House
859 KLINE ST, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5099717 • WORTH CLARK REALTY, Chris Day
Download the Ultimate 55+ Homebuying Guide
Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
The Villages®
![2498 YALAHA AVE, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,210 sq ft
|Villa
2498 YALAHA AVE, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5102322 • LPT REALTY, LLC, Dave Monty
Stonecrest
![11584 SE 175TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,702 sq ft
|House
11584 SE 175TH ST, SUMMERFIELD, FL, 3449...
Community: Stonecrest
MLS G5101060 • REALTY EXECUTIVES IN THE VILLAGES,...
The Villages®
![5446 ALFREDSON TER, THE VILLAGES, FL, 32..., The Villages, FL 32163]()
3 beds
|2 baths
|1,918 sq ft
|House
5446 ALFREDSON TER, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5100282 • WORTH CLARK REALTY, Eddie Sutton
The Villages®
![9231 SE 171ST COOPER LOOP, THE VILLAGES,..., The Villages, FL 32162]()
3 beds
|2 baths
|1,850 sq ft
|House
9231 SE 171ST COOPER LOOP, THE VILLAGES,...
Community: The Villages®
MLS G5102413 • REALTY EXECUTIVES IN THE VILLAGES,...
Vienna Square
![2470 SALZBURG LOOP, WINTER HAVEN, FL, 33..., Winter Haven, FL 33884]()
3 beds
|2 baths
|1,935 sq ft
|House
2470 SALZBURG LOOP, WINTER HAVEN, FL, 33...
Community: Vienna Square
MLS O6344501 • PREMIUM REAL ESTATE SERVICES, Nere...
Want to learn more about 55+ communities in Winter Park?
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(888) 625-4885
The Villages®
![1712 MORELOS RD, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,193 sq ft
|House
1712 MORELOS RD, THE VILLAGES, FL, 32159
Community: The Villages®
MLS W7879135 • LISTWITHFREEDOM.COM, Ralph Harvey
VillageWalk at Lake Nona
![11944 ISELLE DR, ORLANDO, FL, 32827, Orlando, FL 32827]()
3 beds
|2 baths
|1,542 sq ft
|Villa
11944 ISELLE DR, ORLANDO, FL, 32827
Community: VillageWalk at Lake Nona
MLS O6348466 • PINELOCH INVESTMENTS, INC, Bertran...
The Villages®
![1003 MATTHEW AVE, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|1,191 sq ft
|Manufactured Home
1003 MATTHEW AVE, LADY LAKE, FL, 32159
Community: The Villages®
MLS OM710517 • CENTRAL CITY REALTY, Issa Nesheiwa...
Pennbrooke Fairways
![734 GRAND VISTA TRL, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,595 sq ft
|House
734 GRAND VISTA TRL, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS G5102817 • CENTURY 21 ALTON CLARK, Regina Rod...
High Vista at Ridgewood Lakes
![105 RIDGE VIEW DR, DAVENPORT, FL, 33837, Davenport, FL 33837]()
2 beds
|2 baths
|1,542 sq ft
|House
105 RIDGE VIEW DR, DAVENPORT, FL, 33837
Community: High Vista at Ridgewood Lakes
MLS S5133718 • KELLER WILLIAMS REALTY AT THE LAKE...
Download the Ultimate 55+ Homebuying Guide
Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
The Villages®
![1707 LILLY LN, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,290 sq ft
|Manufactured Home
1707 LILLY LN, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5102081 • COLDWELL BANKER VANGUARD LIFESTYLE...
The Villages®
![2737 PRIVADA DR, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,527 sq ft
|House
2737 PRIVADA DR, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5103630 • COLDWELL BANKER VANGUARD LIFESTYLE...
Cresswind at Victoria Gardens
![504 GARDEN CLUB DR, DELAND, FL, 32724, Deland, FL 32724]()
3 beds
|2 baths
|2,220 sq ft
|House
504 GARDEN CLUB DR, DELAND, FL, 32724
Community: Cresswind at Victoria Gardens
MLS O6353033 • EXP REALTY LLC, Aida Rico-Arango
Foxwood Lake Estates
![1530 LONGBOW DR, LAKELAND, FL, 33810, Lakeland, FL 33810]()
2 beds
|2 baths
|1,430 sq ft
|Manufactured Home
1530 LONGBOW DR, LAKELAND, FL, 33810
Community: Foxwood Lake Estates
MLS S5135663 • WATSON REALTY CORP, Lois Ann Cox
The Villages®
![725 CAMELIA CT, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|1,202 sq ft
|Manufactured Home
725 CAMELIA CT, LADY LAKE, FL, 32159
Community: The Villages®
MLS G5104716 • REALTY EXECUTIVES IN THE VILLAGES,...
Want to learn more about 55+ communities in Winter Park?
55places can help!
Questions? Call us:
(888) 625-4885
Grand Haven
![21 BLUE OAK LN, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
MLS FC313330 • KOKOMO REALTY LLC, Tyler Capps
New
The Villages®
![9179 SE 167TH FORD ST, THE VILLAGES, FL,..., The Villages, FL 32162]()
2 beds
|2 baths
|1,152 sq ft
|Villa
9179 SE 167TH FORD ST, THE VILLAGES, FL,...
Community: The Villages®
MLS G5104986 • REALTY EXECUTIVES IN THE VILLAGES,...
The Villages®
![1258 WEATON CT, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,477 sq ft
|House
1258 WEATON CT, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5102656 • REALTY EXECUTIVES IN THE VILLAGES,...
Lake Ashton
![4249 BERWICK DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859]()
2 beds
|2 baths
|1,847 sq ft
|House
4249 BERWICK DR, LAKE WALES, FL, 33859
Community: Lake Ashton
MLS L4957196 • ROOST REALTY GROUP LLC, Barb Wiech...
Spruce Creek South
![17830 SE 95TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,734 sq ft
|House
17830 SE 95TH CIR, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
MLS G5101267 • RE/MAX PREMIER REALTY LADY LK, Ger...
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Want to learn more about 55+ communities in Winter Park?
2,487
homes
near Winter Park
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REIN updates its listings on a daily basis. Data last updated: Nov 30, 2025.
This application does not include information on all of the properties available for sale at this time.
