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Winter Park, FL 55+ active adult communities & homes for sale - Page 43
93 communities near Winter Park
2,414 homes near Winter Park
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4 rating (17 reviews)
![The Villages®]()
$100ks
- $1Ms
The Villages®, The Villages, FL
New and Resale
|
55+ age-restricted
|
Built 1978 - present
|
70,000 homes
4.7 rating (18 reviews)
![Solivita]()
$300ks
- $700ks
Solivita, Kissimmee, FL
New and Resale
|
55+ age-restricted
|
Built 2000 - present
|
5,900 homes
4.5 rating (11 reviews)
![Spruce Creek Country Club]()
$100ks
- $400ks
Spruce Creek Country Club, Summerfield, FL
Resale Only
|
55+ age-restricted
|
Built 1996 - 2007
|
3,250 homes
5 rating (2 reviews)
![Plantation at Leesburg]()
$100ks
- $300ks
Plantation at Leesburg, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1987 - 2008
|
2,820 homes
3.6 rating (48 reviews)
![Latitude Margaritaville]()
$300ks
- $800ks
Latitude Margaritaville, Daytona Beach, FL
Resale Only
|
55+ age-restricted
|
Built 2017 - 2025
|
3,900 homes
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5 rating (1 reviews)
![Plantation Bay Golf &...]()
$400ks
- $2Ms
Plantation Bay Golf &..., Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1988 - present
|
3,500 homes
$300ks
- $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale
|
Age-targeted
|
Built 2004 - present
|
1,561 homes
5 rating (3 reviews)
![Lake Ashton]()
$200ks
- $500ks
Lake Ashton, Lake Wales, FL
Resale Only
|
55+ age-restricted
|
Built 2002 - present
|
1,600 homes
5 rating (3 reviews)
![Stonecrest]()
$200ks
- $500ks
Stonecrest, Summerfield, FL
Resale Only
|
55+ age-restricted
|
Built 1990 - 2024
|
2,224 homes
$200ks
- $800ks
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.
2.8 rating (6 reviews)
![Arlington Ridge]()
$200ks
- $500ks
Arlington Ridge, Leesburg, FL
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
629 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 (3 reviews)
![Twin Lakes]()
$200ks
- $600ks
Twin Lakes, St. Cloud, FL
New and Resale
|
55+ age-restricted
|
Built 2016 - present
|
2,000 homes
5 rating (8 reviews)
![Royal Highlands]()
$200ks
- $400ks
Royal Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2006
|
1,500 homes
5 rating (7 reviews)
![Kings Ridge]()
$200ks
- $400ks
Kings Ridge, Clermont, FL
Resale Only
|
55+ age-restricted
|
Built 1995 - 2000
|
2,088 homes
3.8 rating (4 reviews)
![Spruce Creek South]()
$100ks
- $200ks
Spruce Creek South, Summerfield, FL
Resale Only
|
55+ age-restricted
|
Built 1989 - 1995
|
1,650 homes
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$100ks
- $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only
|
Age-targeted
|
Built 1980 - 2006
|
1,806 homes
$300ks
- $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1980 - present
|
1,000 homes
5 rating (1 reviews)
![Sandpiper Golf & Coun...]()
$100ks
- $300ks
Sandpiper Golf & Coun..., Lakeland, FL
New and Resale
|
55+ age-restricted
|
Built 1985 - present
|
1,193 homes
4 rating (4 reviews)
![Lakes of Mount Dora]()
$300ks
- $1Ms
Lakes of Mount Dora, Mount Dora, FL
New and Resale
|
55+ age-restricted
|
Built 2006 - present
|
950 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 rating (2 reviews)
![Harbor Hills Country Club]()
$300ks
- $900ks
Harbor Hills Country Club, Lady Lake, FL
New and Resale
|
Age-targeted
|
Built 1989 - present
|
940 homes
3.6 rating (5 reviews)
![Heritage Hills]()
$200ks
- $400ks
Heritage Hills, Clermont, FL
New and Resale
|
55+ age-restricted
|
Built 2006 - present
|
1,154 homes
5 rating (1 reviews)
![Del Webb Sunbridge]()
$400ks
- $800ks
Del Webb Sunbridge, St. Cloud, FL
New and Resale
|
55+ age-restricted
|
Built 2019 - present
|
1,300 homes
5 rating (1 reviews)
![Cresswind at Victoria Gar...]()
$200ks
- $500ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only
|
55+ age-restricted
|
Built 2001 - 2022
|
1,070 homes
$200ks
- $400ks
Summer Trees, Port Orange, FL
Resale Only
|
55+ age-restricted
|
Built 1976 - 2005
|
500 homes
$200ks
- $400ks
The Lakes at Harmony, Harmony, FL
New and Resale
|
55+ age-restricted
|
Built 2016 - present
|
400 homes
5 rating (1 reviews)
![Royal Harbor]()
$200ks
- $800ks
Royal Harbor, Tavares, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2008
|
755 homes
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5 rating (2 reviews)
![Heritage Isle]()
$300ks
- $500ks
Heritage Isle, Viera, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2017
|
1,500 homes
5 rating (8 reviews)
![Pennbrooke Fairways]()
<$100k
- $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1980 - 2004
|
1,200 homes
$400ks
- $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1985 - present
|
976 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
- $600ks
Four Seasons at Orlando, Kissimmee, FL
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
557 homes
$100ks
- $200ks
Scottish Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1983 - 1992
|
653 homes
4.8 rating (6 reviews)
![Highland Lakes]()
$100ks
- $200ks
Highland Lakes, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1990 - 1999
|
938 homes
1 rating (1 reviews)
![Sullivan Ranch]()
$200ks
- $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2020
|
692 homes
$200ks
- $1Ms
The Country Club of Mount..., Mount Dora, FL
Resale Only
|
Age-targeted
|
Built 1991 - 2005
|
827 homes
5 rating (1 reviews)
![VillageWalk at Lake Nona]()
$300ks
- $700ks
VillageWalk at Lake Nona, Orlando, FL
Resale Only
|
Age-targeted
|
Built 2006 - 2016
|
1,300 homes
$100ks
- $200ks
Foxwood Lake Estates, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1982 - 1987
|
545 homes
Want to learn more about 55+ communities in Winter Park?
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Questions? Call us:
(888) 625-4885
4.4 rating (16 reviews)
![Del Webb Orlando]()
$200ks
- $500ks
Del Webb Orlando, Davenport, FL
Resale Only
|
55+ age-restricted
|
Built 2007 - 2021
|
937 homes
5 rating (2 reviews)
![Bridgewater at Viera]()
$300ks
- $800ks
Bridgewater at Viera, Melbourne, FL
Resale Only
|
55+ age-restricted
|
Built 2017 - 2023
|
870 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.
The Villages®
![3073 RIVERDALE RD, THE VILLAGES, FL, 321..., The Villages, FL 32162]()
3 beds
|2 baths
|1,700 sq ft
|House
3073 RIVERDALE RD, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5106971 • FONTANA REALTY INC., Tina Teraskie...
Alamanda Key
![543 HEMING WAY, MELBOURNE, FL, 32901, Melbourne, FL 32901]()
MLS 1067582 • RE/MAX Elite, Todd Ostrander
Venetian Bay
![3470 TESORO CIR, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|2,852 sq ft
|House
3470 TESORO CIR, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
MLS 1222144 • EXP Realty LLC, Dolores Leza
Solivita
![790 CARMEL LN, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5142276 • BORCHINI REALTY, Charles Borchini
The Villages®
![12392 NE 48TH LOOP, OXFORD, FL, 34484, Oxford, FL 34484]()
4 beds
|4 baths
|2,002 sq ft
|House
12392 NE 48TH LOOP, OXFORD, FL, 34484
Community: The Villages®
MLS G5107252 • ERA GRIZZARD REAL ESTATE, Julie To...
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(888) 625-4885
The Villages®
![4913 NE 122ND AVE, OXFORD, FL, 34484, Oxford, FL 34484]()
4 beds
|3 baths
|2,629 sq ft
|House
4913 NE 122ND AVE, OXFORD, FL, 34484
Community: The Villages®
MLS OM717368 • GLOBALWIDE REALTY LLC, Alexis Gayn...
Del Webb Orlando
![516 PAMPLONA PL, DAVENPORT, FL, 33837, Davenport, FL 33837]()
2 beds
|2 baths
|1,445 sq ft
|House
516 PAMPLONA PL, DAVENPORT, FL, 33837
Community: Del Webb Orlando
MLS S5142468 • RIDGE REALTY GROUP LLC, Linda Spen...
The Villages®
![8241 SE 176TH LAWSON LOOP, THE VILLAGES,..., The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
8241 SE 176TH LAWSON LOOP, THE VILLAGES,...
Community: The Villages®
MLS V4946954 • WATSON REALTY CORP, Guy Kinsman
Kings Ridge
![3656 EVERSHOLT ST, CLERMONT, FL, 34711, Clermont, FL 34711]()
3 beds
|2 baths
|1,498 sq ft
|House
3656 EVERSHOLT ST, CLERMONT, FL, 34711
Community: Kings Ridge
MLS O6376288 • NETWORTH REALTY OF ORLANDO, LLC, W...
Legacy of Leesburg
![27601 COUNTRY STONE CT, LEESBURG, FL, 34..., Leesburg, FL 34748]()
3 beds
|2 baths
|2,066 sq ft
|House
27601 COUNTRY STONE CT, LEESBURG, FL, 34...
Community: Legacy of Leesburg
MLS G5107236 • KELLER WILLIAMS CLASSIC, Scott Coh...
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.
Solivita
![305 ROCK SPRINGS DR, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759]()
3 beds
|3 baths
|2,454 sq ft
|House
305 ROCK SPRINGS DR, KISSIMMEE, FL, 3475...
Community: Solivita
MLS S5142040 • PELLEGO, LLC, Stan Wilson
The Villages®
![3435 INVERARY AVE, THE VILLAGES, FL, 321..., The Villages, FL 32163]()
3 beds
|2 baths
|1,635 sq ft
|House
3435 INVERARY AVE, THE VILLAGES, FL, 321...
Community: The Villages®
MLS OM717367 • FRANK KIRSCHNER REAL ESTATE, Frank...
Breakaway Trails
![71 CARRIAGE CREEK WAY, ORMOND BEACH, FL,..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,295 sq ft
|House
71 CARRIAGE CREEK WAY, ORMOND BEACH, FL,...
Community: Breakaway Trails
MLS NS1087091 • THE KEYES COMPANY, Debra Head
The Villages®
![1967 FLOWERSVILLE PL, THE VILLAGES, FL, ..., The Villages, FL 32163]()
3 beds
|3 baths
|2,016 sq ft
|House
1967 FLOWERSVILLE PL, THE VILLAGES, FL, ...
Community: The Villages®
MLS OM717258 • RE/MAX PREMIER REALTY LADY LK, Don...
Scottish Highlands
![1 DURNESS CT 1, LEESBURG, FL, 34788, Leesburg, FL 34788]()
2 beds
|2 baths
|1,200 sq ft
|Condo
1 DURNESS CT 1, LEESBURG, FL, 34788
Community: Scottish Highlands
MLS OM717358 • GREAT EXPECTATIONS REALTY, LLC, Lo...
Scottish Highlands
![510 GALLOWAY CT, LEESBURG, FL, 34788, Leesburg, FL 34788]()
2 beds
|2 baths
|1,171 sq ft
|House
510 GALLOWAY CT, LEESBURG, FL, 34788
Community: Scottish Highlands
MLS G5107211 • COLDWELL BANKER VANGUARD LIFESTYLE...
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Kings Ridge
![4207 KINGSLEY ST, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS G5107108 • RE/MAX TITANIUM GROUP, Kimberly Jo...
The Villages®
![1115 SALIDO AVE, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
3 beds
|2 baths
|1,728 sq ft
|House
1115 SALIDO AVE, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5107206 • RE/MAX FOXFIRE - SUMMERFIELD, Kell...
Pennbrooke Fairways
![32747 TIMBERWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,504 sq ft
|House
32747 TIMBERWOOD DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS G5107140 • MAXREV LLC, Jayne Marvin
Lake Ashton
![4632 TURNBERRY LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859]()
3 beds
|2 baths
|2,354 sq ft
|House
4632 TURNBERRY LN, LAKE WALES, FL, 33859
Community: Lake Ashton
MLS L4958817 • 54 REALTY LLC, Jordan Prais
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.
Halifax Plantation
![2892 MONAGHAN DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
3 beds
|3 baths
|2,040 sq ft
|House
2892 MONAGHAN DR, ORMOND BEACH, FL, 3217...
Community: Halifax Plantation
MLS O6376491 • BETTER HOMES AND GARDENS REAL ESTA...
Solivita
![308 BEACON AVE, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5141183 • PELLEGO, LLC, Diane Cisek
Spruce Creek Country Club
![13667 SE 91ST AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|2,270 sq ft
|House
13667 SE 91ST AVE, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS OM717197 • RE/MAX FOXFIRE - SUMMERFIELD, Ed D...
Lake Ashton
![4189 STONE CREEK LOOP, LAKE WALES, FL, 3..., Lake Wales, FL 33859]()
3 beds
|2 baths
|2,478 sq ft
|House
4189 STONE CREEK LOOP, LAKE WALES, FL, 3...
Community: Lake Ashton
MLS O6376126 • PREMIER SOTHEBYS INT'L REALTY, Ale...
Royal Harbor
![5008 ADRIATIC AVE, TAVARES, FL, 32778, Tavares, FL 32778]()
3 beds
|2 baths
|2,101 sq ft
|House
5008 ADRIATIC AVE, TAVARES, FL, 32778
Community: Royal Harbor
MLS O6375281 • EXP REALTY LLC, Amanda McDade
Lake Ashton
![4360 ASHTON CLUB DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859]()
3 beds
|2 baths
|2,265 sq ft
|House
4360 ASHTON CLUB DR, LAKE WALES, FL, 338...
Community: Lake Ashton
MLS P4937593 • A+ REALTY LLC, Michael Krigelski
The Timbers at Everlands
![2322 ANTARUS DR, PALM BAY, FL, 32907, Palm Bay, FL 32907]()
3 beds
|3 baths
|2,070 sq ft
|House
2322 ANTARUS DR, PALM BAY, FL, 32907
Community: The Timbers at Everlands
MLS 1067327 • CENTURY 21 Circle, Jeffrey B. Chapm...
Want to learn more about 55+ communities in Winter Park?
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(888) 625-4885
Venetian Bay
![3621 CASELLO DR, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|1,827 sq ft
|Townhouse
3621 CASELLO DR, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
MLS NS1087141 • LOCAL LIVING REALTY GROUP, Paul O...
The Villages®
![1653 HOMER AVE, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,887 sq ft
|House
1653 HOMER AVE, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5107110 • REALTY EXECUTIVES IN THE VILLAGES,...
Solivita
![3810 VIA MAZZINI CT, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759]()
3 beds
|3 baths
|3,064 sq ft
|House
3810 VIA MAZZINI CT, KISSIMMEE, FL, 3475...
Community: Solivita
MLS O6374733 • REAL ESTATE HOUSE FL INC, Michele ...
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.
Lake Henry Estates
![422 HARBOURVIEW DR, HAINES CITY, FL, 338..., Haines City, FL 33844]()
3 beds
|2 baths
|1,793 sq ft
|House
422 HARBOURVIEW DR, HAINES CITY, FL, 338...
Community: Lake Henry Estates
MLS P4937616 • KELLER WILLIAMS REALTY SMART 1, Tr...
Fountain View
![1477 FOUNTAIN VIEW ST, ORMOND BEACH, FL,..., Ormond Beach, FL 32174]()
4 beds
|2 baths
|1,836 sq ft
|House
1477 FOUNTAIN VIEW ST, ORMOND BEACH, FL,...
Community: Fountain View
MLS 1222078 • Fiv Realty Co Florida LLC, Kirsten ...
The Villages®
![1819 CAPTIVA CT, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
1819 CAPTIVA CT, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5106889 • SELLSTATE SUPERIOR REALTY, Heather...
Spruce Creek Country Club
![13589 SE 87TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,719 sq ft
|House
13589 SE 87TH CIR, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS OM716952 • SELLSTATE NGR- SUMMERFIELD, Virgil...
Indian River Colony Club
![1372 INDEPENDENCE AVE, MELBOURNE, FL, 32..., Melbourne, FL 32940]()
2 beds
|2 baths
|1,616 sq ft
|House
1372 INDEPENDENCE AVE, MELBOURNE, FL, 32...
Community: Indian River Colony Club
MLS 1067274 • Four Star Real Estate LLC, Shellie ...
The Timbers at Everlands
![845 ANTIBES CT, PALM BAY, FL, 32907, Palm Bay, FL 32907]()
3 beds
|3 baths
|2,006 sq ft
|House
845 ANTIBES CT, PALM BAY, FL, 32907
Community: The Timbers at Everlands
MLS 1067253 • Blue Marlin Real Estate, Jason Bist...
The Timbers at Everlands
![2213 ANTARUS DR, PALM BAY, FL, 32907, Palm Bay, FL 32907]()
2 beds
|3 baths
|1,670 sq ft
|House
2213 ANTARUS DR, PALM BAY, FL, 32907
Community: The Timbers at Everlands
MLS 1067251 • Blue Marlin Real Estate, Jason Bist...
Scottish Highlands
![55 ABERDEEN CIR, LEESBURG, FL, 34788, Leesburg, FL 34788]()
2 beds
|2 baths
|1,056 sq ft
|House
55 ABERDEEN CIR, LEESBURG, FL, 34788
Community: Scottish Highlands
MLS G5106911 • COLDWELL BANKER VANGUARD EDGE, Lor...
Want to learn more about 55+ communities in Winter Park?
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Stonecrest
![17424 SE 111TH AVE, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,446 sq ft
|House
17424 SE 111TH AVE, SUMMERFIELD, FL, 344...
Community: Stonecrest
MLS GC536807 • GARRETT REALTY, Sarah Connol Pegg
Indian River Colony Club
![1680 OLD GLORY BLVD, MELBOURNE, FL, 3294..., Melbourne, FL 32940]()
2 beds
|2 baths
|1,033 sq ft
|House
1680 OLD GLORY BLVD, MELBOURNE, FL, 3294...
Community: Indian River Colony Club
MLS 1067208 • Four Star Real Estate LLC, Shellie ...
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.
Frequently Asked Questions
In Winter Park, there is 1 small community with less than 500 homes.
The smallest 55+ community in Winter Park has 178 homes, the largest has 178 homes, and the average community consists of 178 homes.
Yes, there is new 55+ home available in Winter Park. The most recent community started in Winter Park include Rosalia Winter Park. There is also 1 community in Winter Park that offers new construction homes, including Rosalia Winter Park.
Yes, there is gated 55+ community in Winter Park. The only 55+ community in Winter Park is gated. For instance, Rosalia Winter Park is a gated community with 178 homes.
Want more information about active adult communities around Winter Park?
Want to learn more about 55+ communities in Winter Park?
2,414
homes
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REIN updates its listings on a daily basis. Data last updated: May 25, 2026.
This application does not include information on all of the properties available for sale at this time.
