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Winter Park, FL 55+ active adult communities & homes for sale - Page 36
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:
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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.
Latitude Margaritaville
![485 MARGARITAVILLE AVE, DAYTONA BEACH, F..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,308 sq ft
|Villa
485 MARGARITAVILLE AVE, DAYTONA BEACH, F...
Community: Latitude Margaritaville
MLS TB8476795 • KELLER WILLIAMS REALTY- PALM H, M...
The Villages®
![640 SAN MARINO DR, THE VILLAGES, FL, 321..., The Villages, FL 32159]()
3 beds
|2 baths
|1,494 sq ft
|House
640 SAN MARINO DR, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5108546 • SALLY LOVE REAL ESTATE, Lee Harper
The Villages®
![3559 WYNGATE PL, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|1,559 sq ft
|House
3559 WYNGATE PL, THE VILLAGES, FL, 32163
Community: The Villages®
MLS A4683827 • EXP REALTY LLC, Kathy Dowd
Plantation at Leesburg
![25113 RIVERWALK DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|2,084 sq ft
|House
25113 RIVERWALK DR, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5108788 • ERA GRIZZARD REAL ESTATE, Jim Rich...
Spruce Creek South
![17945 SE 104TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,134 sq ft
|House
17945 SE 104TH TER, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
MLS G5108782 • ERA GRIZZARD REAL ESTATE, Lori Dav...
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Tohoqua Reserve
![1994 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744]()
3 beds
|2 baths
|2,056 sq ft
|House
1994 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
MLS S5144463 • EXP REALTY LLC, Carlos Nolte
Vienna Square
![2452 SALZBURG LOOP, WINTER HAVEN, FL, 33..., Winter Haven, FL 33884]()
2 beds
|2 baths
|1,729 sq ft
|House
2452 SALZBURG LOOP, WINTER HAVEN, FL, 33...
Community: Vienna Square
MLS O6376391 • REAL BROKER, LLC, Mark Colvin
The Villages®
![1301 FONTANA CT, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
3 beds
|2 baths
|2,106 sq ft
|House
1301 FONTANA CT, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5108697 • PREMIER SOTHEBYS INT'L REALTY, Kei...
The Villages®
![1137 SANTA CRUZ DR, THE VILLAGES, FL, 32..., The Villages, FL 32162]()
2 beds
|2 baths
|1,214 sq ft
|Villa
1137 SANTA CRUZ DR, THE VILLAGES, FL, 32...
Community: The Villages®
MLS OM719628 • LPT REALTY, LLC, Brian Williams
Traditions at Lake Ruby
![3363 LIVINGSTON WAY, WINTER HAVEN, FL, 3..., Winter Haven, FL 33884]()
2 beds
|2 baths
|1,118 sq ft
|Villa
3363 LIVINGSTON WAY, WINTER HAVEN, FL, 3...
Community: Traditions at Lake Ruby
MLS TB8478803 • AGILE GROUP REALTY, Beena Kokeram
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.
Breakaway Trails
![3 FOREST VIEW WAY, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|2,737 sq ft
|House
3 FOREST VIEW WAY, ORMOND BEACH, FL, 321...
Community: Breakaway Trails
MLS 1223398 • Realty Pros Assured, Thomas Caffrey
Plantation at Leesburg
![4532 RIVER RIDGE DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,882 sq ft
|House
4532 RIVER RIDGE DR, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5108460 • FLORIDA PLUS REALTY, LLC, Claire B...
Spruce Creek Country Club
![12747 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,575 sq ft
|House
12747 SE 97TH TERRACE RD, SUMMERFIELD, F...
Community: Spruce Creek Country Club
MLS OM719520 • REALTY ONE GROUP DAVALLS, David St...
The Villages®
![3024 PAYNES PL, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|2,222 sq ft
|House
3024 PAYNES PL, THE VILLAGES, FL, 32162
Community: The Villages®
MLS TB8479992 • TOM TUCKER REALTY, Dave Doherty
Solivita
![396 GRAND CANAL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS O6385413 • MARK SPAIN REAL ESTATE, Jeff Jones
The Villages®
![5288 HURTT ST, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|1,642 sq ft
|Villa
5288 HURTT ST, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5108670 • WORTH CLARK REALTY, Talia Franchi
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Huntington at Hunter's Ridge
![35 FAWN HAVEN TRL, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,850 sq ft
|House
35 FAWN HAVEN TRL, ORMOND BEACH, FL, 321...
Community: Huntington at Hunter's Ridge
MLS FC316410 • VENTURE DEVELOPMENT REALTY,INC, El...
Solivita
![899 BELLA VIANA RD, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5144392 • BORCHINI REALTY, Dale Pautz
Four Seasons at Orlando
![7789 FOUR SEASONS BLVD, KISSIMMEE, FL, 3..., Kissimmee, FL 34747]()
3 beds
|3 baths
|2,360 sq ft
|House
7789 FOUR SEASONS BLVD, KISSIMMEE, FL, 3...
Community: Four Seasons at Orlando
MLS O6383852 • KRESSLER REAL ESTATE, Andre Kressl...
Pelican Bay Daytona Beach
![136 SEA DUCK CIR, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32119]()
3 beds
|3 baths
|2,365 sq ft
|House
136 SEA DUCK CIR, DAYTONA BEACH, FL, 321...
Community: Pelican Bay Daytona Beach
MLS V4947502 • LIFE REAL ESTATE, Mark Straka
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.
Plantation Bay Golf & Country Club
![1274 ROYAL POINTE LN, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|2,032 sq ft
|House
1274 ROYAL POINTE LN, ORMOND BEACH, FL, ...
Community: Plantation Bay Golf & Country Club
MLS 1223321 • Realty Pros Assured, Alex Bittner
Heritage Hills
![3550 FAIRWATERS CT D, CLERMONT, FL, 3471..., Clermont, FL 34711]()
2 beds
|2 baths
|1,503 sq ft
|Villa
3550 FAIRWATERS CT D, CLERMONT, FL, 3471...
Community: Heritage Hills
MLS G5107861 • OPTIMA ONE REALTY, INC., Heather W...
Four Seasons at Orlando
![7956 HANSON BAY PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747]()
3 beds
|3 baths
|2,360 sq ft
|House
7956 HANSON BAY PL, KISSIMMEE, FL, 34747
Community: Four Seasons at Orlando
MLS O6384720 • VIVA ORLANDO REALTY INC., Susan Ri...
Solivita
![819 SAN RAPHAEL ST, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5144376 • BELLA VERDE REALTY LLC, Miguel Elv...
Kings Ridge
![3673 ROLLINGBROOK ST, CLERMONT, FL, 3471..., Clermont, FL 34711]()
2 beds
|2 baths
|1,334 sq ft
|House
3673 ROLLINGBROOK ST, CLERMONT, FL, 3471...
Community: Kings Ridge
MLS G5108368 • OLYMPUS EXECUTIVE REALTY INC, Mars...
Summit Greens
![2390 CALEDONIAN ST, CLERMONT, FL, 34711, Clermont, FL 34711]()
3 beds
|2 baths
|1,961 sq ft
|House
2390 CALEDONIAN ST, CLERMONT, FL, 34711
Community: Summit Greens
MLS O6384621 • EXP REALTY LLC, Phil Mariani
The Villages®
![8761 SE 168TH KITTREDGE LOOP, THE VILLAG..., The Villages, FL 32162]()
3 beds
|2 baths
|1,916 sq ft
|House
8761 SE 168TH KITTREDGE LOOP, THE VILLAG...
Community: The Villages®
MLS G5108499 • REALTY EXECUTIVES IN THE VILLAGES,...
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Royal Harbor
![5732 FREEPORT DR, TAVARES, FL, 32778, Tavares, FL 32778]()
MLS G5108407 • BHHS FLORIDA REALTY, Doug Piazza
Cresswind at Lake Harris
![1599 BELLAGIO LOOP, TAVARES, FL, 32778, Tavares, FL 32778]()
2 beds
|2 baths
|1,968 sq ft
|House
1599 BELLAGIO LOOP, TAVARES, FL, 32778
Community: Cresswind at Lake Harris
MLS G5108358 • KELLER WILLIAMS CORNERSTONE RE, Di...
Plantation at Leesburg
![5062 EL DESTINO DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,021 sq ft
|House
5062 EL DESTINO DR, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS O6384006 • ORANGE SLICE PROPERTIES, Yessenia ...
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.
Scottish Highlands
![1625 NEW ABBEY AVE, LEESBURG, FL, 34788, Leesburg, FL 34788]()
2 beds
|2 baths
|1,040 sq ft
|House
1625 NEW ABBEY AVE, LEESBURG, FL, 34788
Community: Scottish Highlands
MLS OM719126 • COLDWELL BANKER VANGUARD EDGE, Val...
The Villages®
![2569 ERROL TER, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,156 sq ft
|Villa
2569 ERROL TER, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5108526 • REALTY EXECUTIVES IN THE VILLAGES,...
Lakeside Landings
![5427 COMPASS PT 1, OXFORD, FL, 34484, Oxford, FL 34484]()
2 beds
|2 baths
|1,281 sq ft
|Condo
5427 COMPASS PT 1, OXFORD, FL, 34484
Community: Lakeside Landings
MLS G5108257 • EXP REALTY LLC, Brenda Bell
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 G5107614 • REALTY EXECUTIVES IN THE VILLAGES,...
Sullivan Ranch
![20913 SULLIVAN RANCH BLVD, MOUNT DORA, F..., Mount Dora, FL 32757]()
3 beds
|2 baths
|1,990 sq ft
|House
20913 SULLIVAN RANCH BLVD, MOUNT DORA, F...
Community: Sullivan Ranch
MLS G5108576 • KELLIE & CO REAL ESTATE, Kellie Wh...
Venetian Bay
![3004 BORASSUS DR, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
4 beds
|3 baths
|2,115 sq ft
|House
3004 BORASSUS DR, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS NS1087419 • ENGEL & VOLKERS NEW SMYRNA, Chris...
The Villages®
![8338 SE 178TH DEVEAUX LN, THE VILLAGES, ..., The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
8338 SE 178TH DEVEAUX LN, THE VILLAGES, ...
Community: The Villages®
MLS G5108100 • REALTY EXECUTIVES IN THE VILLAGES,...
Harbor Hills Country Club
![39644 HARBOR HILLS BLVD, LADY LAKE, FL, ..., Lady Lake, FL 32159]()
3 beds
|2 baths
|2,009 sq ft
|House
39644 HARBOR HILLS BLVD, LADY LAKE, FL, ...
Community: Harbor Hills Country Club
MLS OM719222 • FLORIDA ADVANTAGE REALTY GROUP, Aa...
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The Villages®
![210 PALERMO PL, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
3 beds
|3 baths
|2,118 sq ft
|House
210 PALERMO PL, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5108098 • REALTY EXECUTIVES IN THE VILLAGES,...
Solivita
![812 SAN RAPHAEL ST, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS G5108502 • FLORIDA PLUS REALTY, LLC, Christin...
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.
