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 32
93 communities near Winter Park
2,414 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
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
Want to learn more about 55+ communities in Winter Park?
55places can help!
Questions? Call us:
(888) 625-4885
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
Want to learn more about 55+ communities in Winter Park?
55places can help!
Questions? Call us:
(888) 625-4885
$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
Want to learn more about 55+ communities in Winter Park?
55places can help!
Questions? Call us:
(888) 625-4885
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?
55places can help!
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.
Solivita
![813 GLENDORA RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5144984 • PELLEGO, LLC, Stan Wilson
Grand Haven
![13 VILLAGE VIEW DR, PALM COAST, FL, 3213..., Palm Coast, FL 32137]()
3 beds
|2 baths
|2,093 sq ft
|House
13 VILLAGE VIEW DR, PALM COAST, FL, 3213...
Community: Grand Haven
MLS FC316273 • GRAND LIVING REALTY, Nancy Hutchis...
The Villages®
![17470 SE 93RD VINE AVE, THE VILLAGES, FL..., The Villages, FL 32162]()
2 beds
|2 baths
|1,172 sq ft
|Villa
17470 SE 93RD VINE AVE, THE VILLAGES, FL...
Community: The Villages®
MLS G5109426 • KELLER WILLIAMS CORNERSTONE RE, Ka...
The Villages®
![624 FAYETTE CT, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,502 sq ft
|House
624 FAYETTE CT, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5109497 • REALTY EXECUTIVES IN THE VILLAGES,...
Highland Lakes
![27217 RACQUET CIR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,756 sq ft
|House
27217 RACQUET CIR, LEESBURG, FL, 34748
Community: Highland Lakes
MLS G5108891 • COLDWELL BANKER REALTY, Sara Suthe...
Want to learn more about 55+ communities in Winter Park?
55places can help!
Questions? Call us:
(888) 625-4885
Venetian Bay
![3049 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|1,614 sq ft
|House
3049 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS O6390353 • WINSLOW HOMES, Megan Winslow
The Villages®
![1988 DOVE HOLLOW RUN, THE VILLAGES, FL, ..., The Villages, FL 32162]()
4 beds
|2 baths
|2,544 sq ft
|House
1988 DOVE HOLLOW RUN, THE VILLAGES, FL, ...
Community: The Villages®
MLS G5109106 • SALLY LOVE REAL ESTATE, Kim Coffer
Venetian Bay
![3057 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168]()
4 beds
|4 baths
|2,086 sq ft
|Townhouse
3057 ISLES WAY, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
MLS NS1087614 • EXIT REAL ESTATE PROPERTY SOL, Ca...
Trilogy® Orlando
![334 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736]()
2 beds
|2 baths
|1,967 sq ft
|House
334 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
MLS G5109432 • KELLER WILLIAMS ELITE PARTNERS III...
Harbor Hills Country Club
![39125 TACOMA DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
3 beds
|3 baths
|2,584 sq ft
|House
39125 TACOMA DR, LADY LAKE, FL, 32159
Community: Harbor Hills Country Club
MLS G5109495 • ORISON PROPERTIES INC., Stephanie ...
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
![3734 HASTING LN, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS G5108857 • COLDWELL BANKER HUBBARD HANSEN, Je...
Trilogy® Orlando
![371 SALT MARSH LN, GROVELAND, FL, 34736, Groveland, FL 34736]()
2 beds
|2 baths
|1,624 sq ft
|House
371 SALT MARSH LN, GROVELAND, FL, 34736
Community: Trilogy® Orlando
MLS O6389294 • KELLER WILLIAMS REALTY AT THE PARK...
The Villages®
![5716 MELVIN DR, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|3 baths
|1,901 sq ft
|House
5716 MELVIN DR, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5109455 • RE/MAX PREMIER REALTY, Tammy Freil...
Plantation Bay Golf & Country Club
![1290 ROYAL POINTE LN, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174]()
4 beds
|2 baths
|2,141 sq ft
|House
1290 ROYAL POINTE LN, ORMOND BEACH, FL, ...
Community: Plantation Bay Golf & Country Club
MLS 1224032 • Weichert Realtors Hallmark Properti...
The Villages®
![2261 WELCOME WAY, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
3 beds
|2 baths
|1,488 sq ft
|House
2261 WELCOME WAY, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5108528 • REALTY EXECUTIVES IN THE VILLAGES,...
Bridgewater at Viera
![2718 MILLENNIUM CIR, MELBOURNE, FL, 3294..., Melbourne, FL 32940]()
4 beds
|4 baths
|2,390 sq ft
|House
2718 MILLENNIUM CIR, MELBOURNE, FL, 3294...
Community: Bridgewater at Viera
MLS 1071697 • Ellingson Properties, Gregory Ellin...
Want to learn more about 55+ communities in Winter Park?
55places can help!
Questions? Call us:
(888) 625-4885
The Villages®
![1107 PELION PL, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,196 sq ft
|Villa
1107 PELION PL, THE VILLAGES, FL, 32162
Community: The Villages®
MLS OM720640 • RE/MAX FOXFIRE - SUMMERFIELD, Ed D...
Spruce Creek Country Club
![9037 SE 136TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|2 baths
|2,025 sq ft
|House
9037 SE 136TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek Country Club
MLS G5109404 • RE/MAX PREMIER REALTY LADY LK, Rob...
The Villages®
![17967 SE 87TH MELROSE CT, THE VILLAGES, ..., The Villages, FL 32162]()
3 beds
|2 baths
|1,924 sq ft
|House
17967 SE 87TH MELROSE CT, THE VILLAGES, ...
Community: The Villages®
MLS G5109451 • REAL BROKER, LLC, Denise Beserock
Trilogy® Orlando
![651 CONSERVATION BLVD, GROVELAND, FL, 34..., Groveland, FL 34736]()
3 beds
|2 baths
|1,862 sq ft
|House
651 CONSERVATION BLVD, GROVELAND, FL, 34...
Community: Trilogy® Orlando
MLS G5109135 • COMMUNITY ELITE REALTY, Nancy Aitk...
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.
Pennbrooke Fairways
![32833 TIMBERWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,975 sq ft
|House
32833 TIMBERWOOD DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS G5109388 • ERA GRIZZARD REAL ESTATE, Dalemari...
Solivita
![113 TIVOLI TRACE CT, POINCIANA, FL, 3475..., Poinciana, FL 34759]()
3 beds
|3 baths
|2,450 sq ft
|House
113 TIVOLI TRACE CT, POINCIANA, FL, 3475...
Community: Solivita
MLS S5145595 • BORCHINI REALTY, Yamile Osorio Var...
Spruce Creek Country Club
![9512 SE 124TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
2 beds
|3 baths
|2,475 sq ft
|House
9512 SE 124TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek Country Club
MLS OM720061 • JUDY L. TROUT REALTY, Jennifer Tra...
Grand Haven
![3 RIVER PARK DR, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
2 beds
|2 baths
|1,828 sq ft
|Townhouse
3 RIVER PARK DR, PALM COAST, FL, 32137
Community: Grand Haven
MLS FC316807 • COASTAL GATEWAY REAL ESTATE GR, La...
Trilogy® Orlando
![389 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736]()
2 beds
|2 baths
|1,932 sq ft
|House
389 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
MLS S5145090 • WATSON REALTY CORP., William Sirig...
Summer Trees
![103 MAGNOLIA LOOP, PORT ORANGE, FL, 3212..., Port Orange, FL 32128]()
2 beds
|2 baths
|1,553 sq ft
|House
103 MAGNOLIA LOOP, PORT ORANGE, FL, 3212...
Community: Summer Trees
MLS 1223999 • RE/MAX Signature, Kimberly Sbordone...
Venetian Bay
![2910 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|1,758 sq ft
|House
2910 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS A4685766 • REALTY ONE GROUP MVP, Loukas Masou...
Want to learn more about 55+ communities in Winter Park?
55places can help!
Questions? Call us:
(888) 625-4885
Summer Trees
![111 CYPRESS POND RD, PORT ORANGE, FL, 32..., Port Orange, FL 32128]()
2 beds
|2 baths
|1,160 sq ft
|House
111 CYPRESS POND RD, PORT ORANGE, FL, 32...
Community: Summer Trees
MLS NS1087600 • COLLADO REAL ESTATE, Bryan Disbro...
Latitude Margaritaville
![373 HANG LOOSE WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,466 sq ft
|House
373 HANG LOOSE WAY, DAYTONA BEACH, FL, 3...
Community: Latitude Margaritaville
MLS FC316817 • REALTY PROS ASSURED, Daniel Robins...
Sullivan Ranch
![30106 CHEVAL ST, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
4 beds
|3 baths
|2,590 sq ft
|House
30106 CHEVAL ST, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
MLS O6389511 • LAKEFIELD REALTY GROUP LLC, Autumn...
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.
Harbor Hills Country Club
![39407 TREELINE DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
4 beds
|4 baths
|2,502 sq ft
|House
39407 TREELINE DR, LADY LAKE, FL, 32159
Community: Harbor Hills Country Club
MLS G5109392 • AKIN REALTY COMPANY, Fran Dann-Aki...
Indian River Colony Club
![1161 CONTINENTAL AVE, MELBOURNE, FL, 329..., Melbourne, FL 32940]()
2 beds
|2 baths
|1,880 sq ft
|House
1161 CONTINENTAL AVE, MELBOURNE, FL, 329...
Community: Indian River Colony Club
MLS 1071561 • Four Star Real Estate LLC, Shellie ...
Legacy of Leesburg
![26903 HONEYMOON AVE, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,526 sq ft
|House
26903 HONEYMOON AVE, LEESBURG, FL, 34748
Community: Legacy of Leesburg
MLS G5109408 • COOPER HOMEFRONT REALTY, Joe Coope...
The Villages®
![889 JAY ST, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|1,986 sq ft
|Villa
889 JAY ST, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5109340 • SELLSTATE SUPERIOR REALTY, Susan B...
VillageWalk at Lake Nona
![12290 REGAL LILY LN, ORLANDO, FL, 32827, Orlando, FL 32827]()
4 beds
|4 baths
|3,000 sq ft
|House
12290 REGAL LILY LN, ORLANDO, FL, 32827
Community: VillageWalk at Lake Nona
MLS O6389610 • CHARLES RUTENBERG REALTY ORLANDO, ...
Heritage Hills
![3551 FAIRWATERS CT C, CLERMONT, FL, 3471..., Clermont, FL 34711]()
2 beds
|2 baths
|1,374 sq ft
|Villa
3551 FAIRWATERS CT C, CLERMONT, FL, 3471...
Community: Heritage Hills
MLS O6387802 • BHHS FLORIDA REALTY, Ashley Boyd
Traditions at Lake Ruby
![4020 CARTERET DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884]()
4 beds
|3 baths
|2,282 sq ft
|House
4020 CARTERET DR, WINTER HAVEN, FL, 3388...
Community: Traditions at Lake Ruby
MLS O6389154 • KELLER WILLIAMS ADVANTAGE III, Sof...
The Villages®
![5845 STORMS AVE, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|2,627 sq ft
|House
5845 STORMS AVE, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5109376 • WORTH CLARK REALTY, Chris Day
Want to learn more about 55+ communities in Winter Park?
55places can help!
Questions? Call us:
(888) 625-4885
Royal Harbor
![5245 CHINA SEA DR, TAVARES, FL, 32778, Tavares, FL 32778]()
3 beds
|2 baths
|1,862 sq ft
|House
5245 CHINA SEA DR, TAVARES, FL, 32778
Community: Royal Harbor
MLS G5109305 • BHHS FLORIDA REALTY, Catherine Lan...
The Villages®
![4354 ZEPPELIN RD, THE VILLAGES, FL, 3216..., The Villages, FL 32163]()
3 beds
|2 baths
|1,914 sq ft
|House
4354 ZEPPELIN RD, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5109204 • WORTH CLARK REALTY, Sheila Skrobec...
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
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: May 25, 2026.
This application does not include information on all of the properties available for sale at this time.
