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Winter Park, FL 55+ active adult communities & homes for sale - Page 44
98 communities near Winter Park
2,702 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
$300ks
- $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale
|
Age-targeted
|
Built 2004 - present
|
1,561 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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4.7 rating (18 reviews)
![Solivita]()
$300ks
- $700ks
Solivita, Kissimmee, FL
New and Resale
|
55+ age-restricted
|
Built 2000 - present
|
5,900 homes
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
5 rating (3 reviews)
![Stonecrest]()
$200ks
- $500ks
Stonecrest, Summerfield, FL
Resale Only
|
55+ age-restricted
|
Built 1990 - 2024
|
2,224 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
$100ks
- $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only
|
Age-targeted
|
Built 1980 - 2006
|
1,806 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.
$200ks
- $800ks
Grand Haven, Palm Coast, FL
New and Resale
|
Age-targeted
|
Built 1997 - present
|
1,901 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 (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
- $400ks
Royal Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2006
|
1,500 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
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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4 rating (4 reviews)
![Lakes of Mount Dora]()
$300ks
- $900ks
Lakes of Mount Dora, Mount Dora, FL
New and Resale
|
55+ age-restricted
|
Built 2006 - present
|
950 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
2.8 rating (6 reviews)
![Arlington Ridge]()
$200ks
- $500ks
Arlington Ridge, Leesburg, FL
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
629 homes
$300ks
- $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1980 - present
|
1,000 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)
![Cresswind at Victoria Gar...]()
$300ks
- $500ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only
|
55+ age-restricted
|
Built 2001 - 2022
|
1,070 homes
$200ks
- $1Ms
The Country Club of Mount..., Mount Dora, FL
Resale Only
|
Age-targeted
|
Built 1991 - 2005
|
827 homes
$100ks
- $300ks
Highland Fairways, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1983 - 1998
|
660 homes
$400ks
- $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1985 - present
|
976 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 (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)
![Del Webb Sunbridge]()
$400ks
- $800ks
Del Webb Sunbridge, St. Cloud, FL
New and Resale
|
55+ age-restricted
|
Built 2019 - present
|
1,300 homes
$300ks
Heritage - The Cottages o..., Okahumpka, FL
New Construction
|
55+ age-restricted
|
Built 2022 - present
|
179 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
- $400ks
Gatherings of Lake Nona, Orlando, FL
New and Resale
|
55+ age-restricted
|
Built 2017 - present
|
216 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
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
$100ks
- $200ks
Foxwood Lake Estates, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1982 - 1987
|
545 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
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
$200ks
- $500ks
The Timbers at Everlands, Palm Bay, FL
New Construction
|
55+ age-restricted
|
Built 2023 - present
|
450 homes
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Questions? Call us:
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$200ks
- $400ks
The Lakes at Harmony, Harmony, FL
New and Resale
|
55+ age-restricted
|
Built 2016 - present
|
400 homes
$100ks
- $200ks
Colonnades, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1985 - 1994
|
360 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.
Cindy Certified
The Villages®
![1420 FAIRWAY ST, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,156 sq ft
|Villa
1420 FAIRWAY ST, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5112282 • MICKI BLACKBURN REALTY, Myra Paxto... • MICKI BLACKBURN REALTY
Trilogy® Orlando
![508 NARROW VIEW LN, GROVELAND, FL, 34736, Groveland, FL 34736]()
2 beds
|2 baths
|1,835 sq ft
|House
508 NARROW VIEW LN, GROVELAND, FL, 34736
Community: Trilogy® Orlando
MLS O6406226 • REDFIN CORPORATION, David Lambert • REDFIN CORPORATION
Cindy Certified
The Villages®
![2140 ESTEVEZ DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|1,143 sq ft
|House
2140 ESTEVEZ DR, LADY LAKE, FL, 32159
Community: The Villages®
MLS G5112270 • SELLSTATE SUPERIOR REALTY, Heather... • SELLSTATE SUPERIOR REALTY
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Cindy Certified
Esplanade at McKinnon Groves
![11235 CARDING MILL LN, WINTER GARDEN, FL..., Winter Garden, FL 34787]()
3 beds
|3 baths
|2,085 sq ft
|House
11235 CARDING MILL LN, WINTER GARDEN, FL...
Community: Esplanade at McKinnon Groves
MLS O6407112 • TAYLOR MORRISON REALTY OF FLORIDA ... • TAYLOR MORRISON REALTY OF FLORIDA INC
Twin Lakes
![4912 CATALPA DR, ST CLOUD, FL, 34772, St Cloud, FL 34772]()
MLS O6405805 • COLDWELL BANKER REALTY, Michelle B... • COLDWELL BANKER REALTY
Royal Harbor
![6274 SAILBOAT AVE, TAVARES, FL, 32778, Tavares, FL 32778]()
4 beds
|3 baths
|3,323 sq ft
|House
6274 SAILBOAT AVE, TAVARES, FL, 32778
Community: Royal Harbor
MLS G5112173 • MORRIS REALTY AND INVESTMENTS, Jo ... • MORRIS REALTY AND INVESTMENTS
Grand Haven
![34 N WATERVIEW DR, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
4 beds
|4 baths
|3,006 sq ft
|House
34 N WATERVIEW DR, PALM COAST, FL, 32137
Community: Grand Haven
MLS FC318412 • REALTY EXCHANGE, LLC, Brittany Lic... • REALTY EXCHANGE, 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.
The Country Club of Mount Dora
![1641 EDGEWATER DR, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
4 beds
|3 baths
|3,813 sq ft
|House
1641 EDGEWATER DR, MOUNT DORA, FL, 32757
Community: The Country Club of Mount Dora
MLS G5112267 • MORRIS REALTY AND INVESTMENTS, Cra... • MORRIS REALTY AND INVESTMENTS
Sandpiper Golf & Country Club
![6380 EGRET DR 6, LAKELAND, FL, 33809, Lakeland, FL 33809]()
2 beds
|2 baths
|1,326 sq ft
|Villa
6380 EGRET DR 6, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS L4961815 • COLDWELL BANKER REALTY, Jack Mille... • COLDWELL BANKER REALTY
Lake Ashton
![4465 STRATHMORE DR, LAKE WALES, FL, 3385..., Lake Wales, FL 33859]()
3 beds
|2 baths
|1,898 sq ft
|House
4465 STRATHMORE DR, LAKE WALES, FL, 3385...
Community: Lake Ashton
MLS TB8502329 • KELLER WILLIAMS TAMPA PROPERTIES,... • KELLER WILLIAMS TAMPA PROPERTIES
Plantation at Leesburg
![24947 CRANES ROOST CIR, LEESBURG, FL, 34..., Leesburg, FL 34748]()
3 beds
|2 baths
|1,653 sq ft
|House
24947 CRANES ROOST CIR, LEESBURG, FL, 34...
Community: Plantation at Leesburg
MLS G5112244 • VANTAGE POINT REALTY CO., Tracie R... • VANTAGE POINT REALTY CO.
Cindy Certified
VillageWalk at Lake Nona
![11844 ASTILBE DR, ORLANDO, FL, 32827, Orlando, FL 32827]()
2 beds
|2 baths
|1,706 sq ft
|Halfplex
11844 ASTILBE DR, ORLANDO, FL, 32827
Community: VillageWalk at Lake Nona
MLS O6404157 • KELLER WILLIAMS ADVANTAGE 2 REALTY... • KELLER WILLIAMS ADVANTAGE 2 REALTY
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Grand Haven
![5 SANDPIPER CT, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
MLS FC318187 • GRAND LIVING REALTY, David Boettge... • GRAND LIVING REALTY
Latitude Margaritaville
![221 SAND BAR LN, DAYTONA BEACH, FL, 3212..., Daytona Beach, FL 32124]()
3 beds
|2 baths
|1,922 sq ft
|House
221 SAND BAR LN, DAYTONA BEACH, FL, 3212...
Community: Latitude Margaritaville
MLS 1226266 • Ponce Inlet Realty, Inc, Terri Spru... • Ponce Inlet Realty, Inc
The Villages®
![9304 SE 170TH HUMPHREYS LOOP, THE VILLAG..., The Villages, FL 32162]()
3 beds
|2 baths
|1,678 sq ft
|House
9304 SE 170TH HUMPHREYS LOOP, THE VILLAG...
Community: The Villages®
MLS OM724476 • KELLER WILLIAMS CORNERSTONE RE, Cr... • KELLER WILLIAMS CORNERSTONE RE
The Villages®
![1222 ZAPATA PL, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|1 baths
|936 sq ft
|Manufactured Home
1222 ZAPATA PL, LADY LAKE, FL, 32159
Community: The Villages®
MLS G5112166 • OLYMPUS EXECUTIVE REALTY INC, Jorg... • OLYMPUS EXECUTIVE REALTY INC
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 Timbers at Everlands
![1424 BLESSED ISLES DR, PALM BAY, FL, 329..., Palm Bay, FL 32907]()
3 beds
|3 baths
|2,470 sq ft
|House
1424 BLESSED ISLES DR, PALM BAY, FL, 329...
Community: The Timbers at Everlands
MLS 1076961 • CENTURY 21 Baytree Realty, Louis Ro... • CENTURY 21 Baytree Realty
Cindy Certified
Colonnades
![4828 SQUIRE HOLLOW DR, LAKELAND, FL, 338..., Lakeland, FL 33811]()
2 beds
|2 baths
|1,330 sq ft
|House
4828 SQUIRE HOLLOW DR, LAKELAND, FL, 338...
Community: Colonnades
MLS L4960713 • COLDWELL BANKER REALTY, Lisa Broch... • COLDWELL BANKER REALTY
Kings Ridge
![4127 KINGSLEY ST, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS G5111723 • REAL BROKER, LLC, Diane Rogers • REAL BROKER, LLC
Cindy Certified
Kings Ridge
![3445 CAPLAND AVE, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS G5112125 • RE/MAX TITANIUM GROUP, Kimberly Jo... • RE/MAX TITANIUM GROUP
Kings Ridge
![3716 KINGSWOOD CT, CLERMONT, FL, 34711, Clermont, FL 34711]()
2 beds
|2 baths
|1,572 sq ft
|House
3716 KINGSWOOD CT, CLERMONT, FL, 34711
Community: Kings Ridge
MLS G5111683 • REAL BROKER, LLC, Diane Rogers • REAL BROKER, LLC
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Pelican Bay Daytona Beach
![108 GREBE CT, DAYTONA BEACH, FL, 32119, Daytona Beach, FL 32119]()
4 beds
|3 baths
|2,079 sq ft
|House
108 GREBE CT, DAYTONA BEACH, FL, 32119
Community: Pelican Bay Daytona Beach
MLS O6406359 • COLLADO REAL ESTATE, Jan Can McDer... • COLLADO REAL ESTATE
Sullivan Ranch
![20831 SULLIVAN RANCH BLVD, MOUNT DORA, F..., Mount Dora, FL 32757]()
3 beds
|2 baths
|1,440 sq ft
|House
20831 SULLIVAN RANCH BLVD, MOUNT DORA, F...
Community: Sullivan Ranch
MLS G5112069 • HANSON REAL ESTATE GROUP, INC., Ma... • HANSON REAL ESTATE GROUP, INC.
The Country Club of Mount Dora
![8011 PINE HOLLOW DR, MOUNT DORA, FL, 327..., Mount Dora, FL 32757]()
3 beds
|2 baths
|2,016 sq ft
|House
8011 PINE HOLLOW DR, MOUNT DORA, FL, 327...
Community: The Country Club of Mount Dora
MLS G5111928 • DAVE LOWE REALTY, INC., Ronald Mus... • DAVE LOWE REALTY, INC.
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
![708 WOODBRIDGE CT, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|2,434 sq ft
|House
708 WOODBRIDGE CT, ORMOND BEACH, FL, 321...
Community: Plantation Bay Golf & Country Club
MLS 1226194 • Realty Pros Assured, Bill Navarra • Realty Pros Assured
Kings Ridge
![2160 ADDISON AVE, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS O6406218 • SENIOR TRANSITIONS REALTY, LLC, Pe... • SENIOR TRANSITIONS REALTY, LLC
Plantation Bay Golf & Country Club
![30 LANDINGS LN 30, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
2 beds
|2 baths
|1,173 sq ft
|Townhouse
30 LANDINGS LN 30, ORMOND BEACH, FL, 321...
Community: Plantation Bay Golf & Country Club
MLS V4948989 • CALNAN REAL ESTATE, Colleen Calnan • CALNAN REAL ESTATE
The Villages®
![7631 SE 170TH LONGVIEW LN, THE VILLAGES,..., The Villages, FL 32162]()
2 beds
|2 baths
|1,186 sq ft
|Villa
7631 SE 170TH LONGVIEW LN, THE VILLAGES,...
Community: The Villages®
MLS G5112104 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
Plantation Bay Golf & Country Club
![30 LANDINGS LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
2 beds
|2 baths
|1,173 sq ft
|Townhouse
30 LANDINGS LN, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS 1226184 • Calnan Real Estate, Colleen Calnan • Calnan Real Estate
Grand Haven
![19 RIVER LANDING DR, PALM COAST, FL, 321..., Palm Coast, FL 32137]()
2 beds
|3 baths
|2,201 sq ft
|Townhouse
19 RIVER LANDING DR, PALM COAST, FL, 321...
Community: Grand Haven
MLS FC318374 • COASTAL GATEWAY REAL ESTATE GR, Su... • COASTAL GATEWAY REAL ESTATE GR
The Villages®
![2306 NACKMAN PL, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,397 sq ft
|Villa
2306 NACKMAN PL, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5110942 • FLAMINGO REAL ESTATE & MNGMT, Apri... • FLAMINGO REAL ESTATE & MNGMT
The Villages®
![1936 NEEDLEWOOD LN, THE VILLAGES, FL, 32..., The Villages, FL 32162]()
3 beds
|2 baths
|1,602 sq ft
|Villa
1936 NEEDLEWOOD LN, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5111971 • KELLER WILLIAMS CORNERSTONE RE, Ka... • KELLER WILLIAMS CORNERSTONE RE
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Halifax Plantation
![3513 KILGALLEN CT, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
4 beds
|5 baths
|5,040 sq ft
|House
3513 KILGALLEN CT, ORMOND BEACH, FL, 321...
Community: Halifax Plantation
MLS FC318331 • ADAMS, CAMERON & CO., REALTORS, Ma... • ADAMS, CAMERON & CO., REALTORS
The Villages®
![17705 SE 93RD HAWTHORNE AVE, THE VILLAGE..., The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
17705 SE 93RD HAWTHORNE AVE, THE VILLAGE...
Community: The Villages®
MLS G5111828 • KELLER WILLIAMS CORNERSTONE RE, Pa... • KELLER WILLIAMS CORNERSTONE RE
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?
2,702
homes
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REIN updates its listings on a daily basis. Data last updated: Aug 25, 2026.
This application does not include information on all of the properties available for sale at this time.
