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Winter Park, FL 55+ active adult communities & homes for sale - Page 24
98 communities near Winter Park
2,698 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
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
$300ks
- $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)
![Plantation at Leesburg]()
$100ks
- $300ks
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
Resale Only
|
55+ age-restricted
|
Built 1990 - 2024
|
2,224 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)
![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.
5 rating (8 reviews)
![Royal Highlands]()
$200ks
- $400ks
Royal Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2006
|
1,500 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
5 rating (3 reviews)
![Lake Ashton]()
$200ks
- $500ks
Lake Ashton, Lake Wales, FL
Resale Only
|
55+ age-restricted
|
Built 2002 - present
|
1,600 homes
$200ks
- $800ks
Grand Haven, Palm Coast, FL
New and Resale
|
Age-targeted
|
Built 1997 - present
|
1,901 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)
![Kings Ridge]()
$200ks
- $400ks
Kings Ridge, Clermont, FL
Resale Only
|
55+ age-restricted
|
Built 1995 - 2000
|
2,088 homes
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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
$300ks
- $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1980 - present
|
1,000 homes
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
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
5 rating (1 reviews)
![Royal Harbor]()
$200ks
- $800ks
Royal Harbor, Tavares, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2008
|
755 homes
5 rating (8 reviews)
![Pennbrooke Fairways]()
<$100k
- $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1980 - 2004
|
1,200 homes
$200ks
- $1Ms
The Country Club of Mount..., Mount Dora, FL
Resale Only
|
Age-targeted
|
Built 1991 - 2005
|
827 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
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
$100ks
- $200ks
Scottish Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1983 - 1992
|
653 homes
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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
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
- $600ks
Four Seasons at Orlando, Kissimmee, FL
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
557 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
Heritage - The Cottages o..., Okahumpka, FL
New Construction
|
55+ age-restricted
|
Built 2022 - present
|
179 homes
$400ks
- $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1985 - present
|
976 homes
4.8 rating (6 reviews)
![Highland Lakes]()
$100ks
- $200ks
Highland Lakes, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1990 - 1999
|
938 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
$300ks
- $400ks
Gatherings of Lake Nona, Orlando, FL
New and Resale
|
55+ age-restricted
|
Built 2017 - present
|
216 homes
$400ks
- $1Ms
Del Webb at Viera, Melbourne, FL
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
1,300 homes
$100ks
- $300ks
Highland Fairways, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1983 - 1998
|
660 homes
$100ks
- $300ks
Lakeside Landings, Oxford, FL
New and Resale
|
Age-targeted
|
Built 2005 - present
|
700 homes
Want to learn more about 55+ communities in Winter Park?
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Questions? Call us:
(888) 625-4885
$200ks
- $400ks
The Lakes at Harmony, Harmony, FL
New and Resale
|
55+ age-restricted
|
Built 2016 - present
|
400 homes
1 rating (1 reviews)
![Sullivan Ranch]()
$200ks
- $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2020
|
692 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®
![6305 DANIELSON LOOP, THE VILLAGES, FL, 3..., The Villages, FL 32163]()
3 beds
|2 baths
|1,419 sq ft
|House
6305 DANIELSON LOOP, THE VILLAGES, FL, 3...
Community: The Villages®
MLS G5115564 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
Cindy Certified
The Villages®
![1842 PUERTO BELLO DR, THE VILLAGES, FL, ..., The Villages, FL 32159]()
2 beds
|2 baths
|1,397 sq ft
|Villa
1842 PUERTO BELLO DR, THE VILLAGES, FL, ...
Community: The Villages®
MLS G5117106 • EXP REALTY LLC, Michelle Hose • EXP REALTY LLC
Halifax Plantation
![1337 CORK DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,510 sq ft
|House
1337 CORK DR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
MLS FC321086 • COASTAL GATEWAY REAL ESTATE GR, M.... • COASTAL GATEWAY REAL ESTATE GR
American Village
![59 GREEN CIR, PALM COAST, FL, 32164, Palm Coast, FL 32164]()
3 beds
|2 baths
|1,740 sq ft
|House
59 GREEN CIR, PALM COAST, FL, 32164
Community: American Village
MLS FC320981 • COLDWELL BANKER PREMIER PROPERTIES... • COLDWELL BANKER PREMIER PROPERTIES
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Questions? Call us:
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Compass Pointe
![788 DANVILLE CIR, WEST MELBOURNE, FL, 32..., West Melbourne, FL 32904]()
3 beds
|2 baths
|1,874 sq ft
|House
788 DANVILLE CIR, WEST MELBOURNE, FL, 32...
Community: Compass Pointe
MLS 1086374 • Home and Family Real Estate, Elliot... • Home and Family Real Estate
Cindy Certified
Four Seasons at Orlando
![1908 FLORA PASS PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747]()
2 beds
|2 baths
|1,437 sq ft
|Villa
1908 FLORA PASS PL, KISSIMMEE, FL, 34747
Community: Four Seasons at Orlando
MLS O6437912 • PROPERTY MARKETERS LLC, Heith Mohl... • PROPERTY MARKETERS LLC
Solivita
![1090 HARBOR RIDGE DR, POINCIANA, FL, 347..., Poinciana, FL 34759]()
2 beds
|2 baths
|1,703 sq ft
|House
1090 HARBOR RIDGE DR, POINCIANA, FL, 347...
Community: Solivita
MLS G5117095 • ERA GRIZZARD REAL ESTATE, Brian Sm... • ERA GRIZZARD REAL ESTATE
Four Seasons at Orlando
![2160 ANTILLES CLUB DR, KISSIMMEE, FL, 34..., Kissimmee, FL 34747]()
2 beds
|2 baths
|1,778 sq ft
|House
2160 ANTILLES CLUB DR, KISSIMMEE, FL, 34...
Community: Four Seasons at Orlando
MLS O6437814 • GOLFPARK PROPERTIES, Robert Guidic... • GOLFPARK PROPERTIES
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.
Pelican Bay Daytona Beach
![136 MUSCOVY CT, DAYTONA BEACH, FL, 32119, Daytona Beach, FL 32119]()
3 beds
|2 baths
|1,561 sq ft
|House
136 MUSCOVY CT, DAYTONA BEACH, FL, 32119
Community: Pelican Bay Daytona Beach
MLS 1230255 • Beycome of Florida LLC, Steven Kole... • Beycome of Florida LLC
Cindy Certified
Royal Harbor
![4958 PORTSMOUTH ST, TAVARES, FL, 32778, Tavares, FL 32778]()
3 beds
|2 baths
|1,819 sq ft
|House
4958 PORTSMOUTH ST, TAVARES, FL, 32778
Community: Royal Harbor
MLS V4950996 • ROUND TABLE REALTY, Roxanne Logan • ROUND TABLE REALTY
The Country Club of Mount Dora
![6022 FALCONBRIDGE PL, MOUNT DORA, FL, 32..., Mount Dora, FL 32757]()
3 beds
|2 baths
|2,023 sq ft
|House
6022 FALCONBRIDGE PL, MOUNT DORA, FL, 32...
Community: The Country Club of Mount Dora
MLS G5117049 • DAVE LOWE REALTY, INC., Andrew Nol... • DAVE LOWE REALTY, INC.
Pelican Bay Daytona Beach
![101 BOB WHITE CT 101J, DAYTONA BEACH, FL..., Daytona Beach, FL 32119]()
2 beds
|2 baths
|1,165 sq ft
|House
101 BOB WHITE CT 101J, DAYTONA BEACH, FL...
Community: Pelican Bay Daytona Beach
MLS 1230240 • Beach City Realty Group, Inc., Pamm... • Beach City Realty Group, Inc.
Grand Haven
![7 RIVER LANDING DR, PALM COAST, FL, 3213..., Palm Coast, FL 32137]()
2 beds
|3 baths
|1,919 sq ft
|Townhouse
7 RIVER LANDING DR, PALM COAST, FL, 3213...
Community: Grand Haven
MLS FC320967 • GRAND LIVING REALTY, Frank Sockman • GRAND LIVING REALTY
Want to learn more about 55+ communities in Winter Park?
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The Villages®
![2018 CASTANO PL, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,213 sq ft
|House
2018 CASTANO PL, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5116434 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
Cindy Certified
The Villages®
![1016 MATTHEW AVE, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
3 beds
|2 baths
|1,511 sq ft
|House
1016 MATTHEW AVE, LADY LAKE, FL, 32159
Community: The Villages®
MLS OM731342 • KELLER WILLIAMS CORNERSTONE RE, Cr... • KELLER WILLIAMS CORNERSTONE RE
Cresswind at Victoria Gardens
![1309 HAYTON AVE, DELAND, FL, 32724, Deland, FL 32724]()
2 beds
|2 baths
|1,651 sq ft
|House
1309 HAYTON AVE, DELAND, FL, 32724
Community: Cresswind at Victoria Gardens
MLS O6437225 • REAL BROKER, LLC, Scott Nance LLC • REAL BROKER, 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.
Heritage Hills
![3505 BELLAND CIR F, CLERMONT, FL, 34711, Clermont, FL 34711]()
2 beds
|2 baths
|1,503 sq ft
|Townhouse
3505 BELLAND CIR F, CLERMONT, FL, 34711
Community: Heritage Hills
MLS 2162569 • BOLD CITY REALTY GROUP INC, JERIKA ... • BOLD CITY REALTY GROUP INC
The Villages®
![6088 KECKONEN DR, THE VILLAGES, FL, 3216..., The Villages, FL 32163]()
3 beds
|2 baths
|1,960 sq ft
|House
6088 KECKONEN DR, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS OM731141 • SOUTHERN REALTY ASSOCIATES, Christ... • SOUTHERN REALTY ASSOCIATES
The Villages®
![17663 SE 92ND GRANTHAM TER, THE VILLAGES..., The Villages, FL 32162]()
3 beds
|2 baths
|1,265 sq ft
|House
17663 SE 92ND GRANTHAM TER, THE VILLAGES...
Community: The Villages®
MLS G5117093 • LPT REALTY, LLC, Bob Woodsford • LPT REALTY, LLC
Twin Lakes
![2541 YELLOW BRICK RD, ST CLOUD, FL, 3477..., St Cloud, FL 34771]()
2 beds
|2 baths
|1,346 sq ft
|Villa
2541 YELLOW BRICK RD, ST CLOUD, FL, 3477...
Community: Twin Lakes
MLS O6437442 • HOME & HIVE REALTY, Stephanie Barb... • HOME & HIVE REALTY
Cindy Certified
The Villages®
![17362 SE 78TH HARMONY CIR, THE VILLAGES,..., The Villages, FL 32162]()
2 beds
|2 baths
|1,198 sq ft
|Villa
17362 SE 78TH HARMONY CIR, THE VILLAGES,...
Community: The Villages®
MLS G5116993 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
High Vista at Ridgewood Lakes
![238 FLEMING LN, DAVENPORT, FL, 33837, Davenport, FL 33837]()
2 beds
|2 baths
|1,877 sq ft
|House
238 FLEMING LN, DAVENPORT, FL, 33837
Community: High Vista at Ridgewood Lakes
MLS S5156329 • KELLER WILLIAMS REALTY AT THE LAKE... • KELLER WILLIAMS REALTY AT THE LAKES
Want to learn more about 55+ communities in Winter Park?
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(888) 625-4885
Gatherings of Lake Nona
![7545 LAUREATE BLVD 7301, ORLANDO, FL, 32..., Orlando, FL 32827]()
2 beds
|2 baths
|1,445 sq ft
|Condo
7545 LAUREATE BLVD 7301, ORLANDO, FL, 32...
Community: Gatherings of Lake Nona
MLS S5156452 • LA ROSA REALTY LLC, Kim Beers • LA ROSA REALTY LLC
Gatherings of Lake Nona
![7545 LAUREATE BLVD 7208, ORLANDO, FL, 32..., Orlando, FL 32827]()
2 beds
|2 baths
|1,368 sq ft
|Condo
7545 LAUREATE BLVD 7208, ORLANDO, FL, 32...
Community: Gatherings of Lake Nona
MLS S5156457 • LA ROSA REALTY LLC, Kim Beers • LA ROSA REALTY LLC
The Villages®
![3147 MANSFIELD ST, THE VILLAGES, FL, 321..., The Villages, FL 32162]()
3 beds
|2 baths
|2,022 sq ft
|House
3147 MANSFIELD ST, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5117024 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
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®
![1452 OLUSTEE PL, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|1,584 sq ft
|House
1452 OLUSTEE PL, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5116550 • LPT REALTY, LLC, Dedee Messina • LPT REALTY, LLC
The Villages®
![8368 SE 176TH LAWSON LOOP, THE VILLAGES,..., The Villages, FL 32162]()
3 beds
|2 baths
|1,785 sq ft
|House
8368 SE 176TH LAWSON LOOP, THE VILLAGES,...
Community: The Villages®
MLS OM731337 • RE/MAX PREMIER REALTY LADY LK, Don... • RE/MAX PREMIER REALTY LADY LK
Highland Lakes
![26245 NEWCOMBE CIR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|3 baths
|2,377 sq ft
|House
26245 NEWCOMBE CIR, LEESBURG, FL, 34748
Community: Highland Lakes
MLS S5156558 • GLOVEN REALTY, J. Cesar Perez • GLOVEN REALTY
Cindy Certified
Plantation Bay Golf & Country Club
![1031 KILKENNY LN, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
2 beds
|3 baths
|1,375 sq ft
|House
1031 KILKENNY LN, ORMOND BEACH, FL, 3217...
Community: Plantation Bay Golf & Country Club
MLS V4950995 • LPT REALTY, LLC, Matthew Buckley • LPT REALTY, LLC
The Villages®
![622 MAYBANK LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
4 beds
|2 baths
|2,548 sq ft
|House
622 MAYBANK LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5117075 • SALLY LOVE REAL ESTATE, Kim Coffer • SALLY LOVE REAL ESTATE
The Villages®
![705 OAK BLVD, WILDWOOD, FL, 34785, Wildwood, FL 34785]()
3 beds
|2 baths
|1,680 sq ft
|Manufactured Home
705 OAK BLVD, WILDWOOD, FL, 34785
Community: The Villages®
MLS OM731187 • DALTON WADE INC, Timothy Cowart • DALTON WADE INC
Cindy Certified
Want to learn more about 55+ communities in Winter Park?
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(888) 625-4885
Spruce Creek South
![17513 SE 95TH CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
2 beds
|2 baths
|1,390 sq ft
|House
17513 SE 95TH CT, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
MLS G5117060 • TEAM WYN REALTY LLC, Gloria Wyning... • TEAM WYN REALTY LLC
Del Webb at Viera
![8994 NIXIE AVE, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
4 beds
|3 baths
|2,149 sq ft
|House
8994 NIXIE AVE, MELBOURNE, FL, 32940
Community: Del Webb at Viera
MLS 1086221 • BHHS Florida Realty, Barbara C Wall • BHHS Florida Realty
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?
2,698
homes
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REIN updates its listings on a daily basis. Data last updated: Oct 10, 2026.
This application does not include information on all of the properties available for sale at this time.
