Call us at (888) 625-4885 to learn more about active adult communities in Winter Park
Winter Park, FL 55+ active adult communities & homes for sale - Page 54
98 communities near Winter Park
2,698 homes near Winter Park
Sort by:
Relevance
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
Want to learn more about 55+ communities in Winter Park?
55places can help!
Questions? Call us:
(888) 625-4885
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
Want to learn more about 55+ communities in Winter Park?
55places can help!
Questions? Call us:
(888) 625-4885
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
Want to learn more about 55+ communities in Winter Park?
55places can help!
Questions? Call us:
(888) 625-4885
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?
55places can help!
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®
![1648 ABASCO CT, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,156 sq ft
|Villa
1648 ABASCO CT, THE VILLAGES, FL, 32162
Community: The Villages®
MLS TB8508059 • HOMECOIN.COM, Jonathan Minerick • HOMECOIN.COM
Cindy Certified
Spruce Creek Country Club
![13500 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491]()
2 beds
|3 baths
|2,333 sq ft
|House
13500 SE 97TH TERRACE RD, SUMMERFIELD, F...
Community: Spruce Creek Country Club
MLS OM724620 • LPT REALTY, LLC, Terri Bramlett • LPT REALTY, LLC
The Villages®
![991 BARRYMOORE LOOP, THE VILLAGES, FL, 3..., The Villages, FL 32162]()
3 beds
|2 baths
|1,527 sq ft
|House
991 BARRYMOORE LOOP, THE VILLAGES, FL, 3...
Community: The Villages®
MLS OM724672 • SALLY LOVE REAL ESTATE, Star Amado... • SALLY LOVE REAL ESTATE
Trilogy® Orlando
![115 CRESCENT MOON DR, GROVELAND, FL, 347..., Groveland, FL 34736]()
3 beds
|2 baths
|1,856 sq ft
|House
115 CRESCENT MOON DR, GROVELAND, FL, 347...
Community: Trilogy® Orlando
MLS O6407445 • EXP REALTY LLC, Eddie Lopez • EXP REALTY LLC
Want to learn more about 55+ communities in Winter Park?
55places can help!
Questions? Call us:
(888) 625-4885
The Villages®
![207 DESOTA CT, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
3 beds
|2 baths
|1,889 sq ft
|House
207 DESOTA CT, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5112093 • COLDWELL BANKER VANGUARD LIFESTYLE... • COLDWELL BANKER VANGUARD LIFESTYLE REALTY
The Villages®
![1000 KENOVA AVE, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
1000 KENOVA AVE, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5112080 • COLDWELL BANKER VANGUARD LIFESTYLE... • COLDWELL BANKER VANGUARD LIFESTYLE REALTY
The Villages®
![2013 SANTO DOMINGO DR, THE VILLAGES, FL,..., The Villages, FL 32159]()
3 beds
|2 baths
|2,015 sq ft
|House
2013 SANTO DOMINGO DR, THE VILLAGES, FL,...
Community: The Villages®
MLS G5112078 • COLDWELL BANKER VANGUARD LIFESTYLE... • COLDWELL BANKER VANGUARD LIFESTYLE REALTY
Royal Highlands
![4841 GLEN COE ST, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|2,197 sq ft
|House
4841 GLEN COE ST, LEESBURG, FL, 34748
Community: Royal Highlands
MLS G5112234 • VANTAGE POINT REALTY CO., Tracie R... • VANTAGE POINT REALTY CO.
Cindy Certified
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®
![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
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
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
Want to learn more about 55+ communities in Winter Park?
55places can help!
Questions? Call us:
(888) 625-4885
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.
Grand Haven
![5 SANDPIPER CT, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
MLS FC318187 • GRAND LIVING REALTY, David Boettge... • GRAND LIVING REALTY
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
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.
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
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
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.
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
Want to learn more about 55+ communities in Winter Park?
55places can help!
Questions? Call us:
(888) 625-4885
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
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
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
![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
Traditions at Lake Ruby
![3023 CANEEL ST, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884]()
2 beds
|2 baths
|1,385 sq ft
|Townhouse
3023 CANEEL ST, WINTER HAVEN, FL, 33884
Community: Traditions at Lake Ruby
MLS TB8504638 • GOYAL & DECOSTER REALTY, Marco Si... • GOYAL & DECOSTER REALTY
Foxwood Lake Estates
![5027 FOREST CREST DR, LAKELAND, FL, 3381..., Lakeland, FL 33810]()
2 beds
|2 baths
|1,248 sq ft
|Manufactured Home
5027 FOREST CREST DR, LAKELAND, FL, 3381...
Community: Foxwood Lake Estates
MLS TB8506521 • GOYAL & DECOSTER REALTY, Marco Si... • GOYAL & DECOSTER REALTY
Del Webb at Viera
![8953 BLISSFUL BREEZE TRL, MELBOURNE, FL,..., Melbourne, FL 32940]()
2 beds
|2 baths
|1,579 sq ft
|Villa
8953 BLISSFUL BREEZE TRL, MELBOURNE, FL,...
Community: Del Webb at Viera
MLS O6405837 • PULTE REALTY OF NORTH FLORIDA LLC,... • PULTE REALTY OF NORTH FLORIDA LLC
Plantation at Leesburg
![24511 BOCAGE WAY, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|3 baths
|2,684 sq ft
|House
24511 BOCAGE WAY, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5111933 • CENTURY 21 MYERS ROSE REALTY, Mary... • CENTURY 21 MYERS ROSE REALTY
The Villages®
![16689 SE 78TH LIVE OAK AVE, THE VILLAGES..., The Villages, FL 32162]()
3 beds
|2 baths
|1,478 sq ft
|House
16689 SE 78TH LIVE OAK AVE, THE VILLAGES...
Community: The Villages®
MLS G5111884 • REAL BROKER, LLC, Denise Beserock • REAL BROKER, LLC
Lake Ashton
![1108 SAWGRASS DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884]()
2 beds
|2 baths
|1,533 sq ft
|House
1108 SAWGRASS DR, WINTER HAVEN, FL, 3388...
Community: Lake Ashton
MLS S5149437 • LA ROSA REALTY CENTRAL FLORIDA LLC... • LA ROSA REALTY CENTRAL FLORIDA LLC
Want to learn more about 55+ communities in Winter Park?
55places can help!
Questions? Call us:
(888) 625-4885
Arlington Ridge
![4025 ARLINGTON RIDGE BLVD, LEESBURG, FL,..., Leesburg, FL 34748]()
3 beds
|2 baths
|1,719 sq ft
|House
4025 ARLINGTON RIDGE BLVD, LEESBURG, FL,...
Community: Arlington Ridge
MLS O6405368 • REDFIN CORPORATION, Giselle Ramire... • REDFIN CORPORATION
The Villages®
![4348 TUSCALOOSA PATH, THE VILLAGES, FL, ..., The Villages, FL 32163]()
3 beds
|3 baths
|1,905 sq ft
|House
4348 TUSCALOOSA PATH, THE VILLAGES, FL, ...
Community: The Villages®
MLS G5111789 • 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.
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
Remove Boundaries ×
Map
Satellite
The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
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.
