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Winter Park, FL 55+ active adult communities & homes for sale - Page 21
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
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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.
Summer Trees
![18 SUMMER TREES RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128]()
2 beds
|2 baths
|1,026 sq ft
|House
18 SUMMER TREES RD, PORT ORANGE, FL, 321...
Community: Summer Trees
MLS 1225259 • Florida Homes Realty & Mortgage, La...
The Villages®
![4942 NE 123RD LN, OXFORD, FL, 34484, Oxford, FL 34484]()
5 beds
|4 baths
|2,402 sq ft
|House
4942 NE 123RD LN, OXFORD, FL, 34484
Community: The Villages®
MLS G5111000 • ERA GRIZZARD REAL ESTATE, Cynthia ...
The Villages®
![481 ISLAND HOUSE PATH, THE VILLAGES, FL,..., The Villages, FL 32163]()
3 beds
|3 baths
|1,903 sq ft
|House
481 ISLAND HOUSE PATH, THE VILLAGES, FL,...
Community: The Villages®
MLS G5111007 • REALTY EXECUTIVES IN THE VILLAGES,...
Latitude Margaritaville
![218 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,303 sq ft
|Villa
218 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F...
Community: Latitude Margaritaville
MLS FC317687 • COASTAL GATEWAY REAL ESTATE GROUP,...
Plantation Bay Golf & Country Club
![31 MAGNOLIA CT, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
7 beds
|5 baths
|3,863 sq ft
|House
31 MAGNOLIA CT, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS FC317609 • VENTURE DEVELOPMENT REALTY,INC, El...
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The Villages®
![17870 SE 92ND AMORY AVE, THE VILLAGES, F..., The Villages, FL 32162]()
2 beds
|2 baths
|1,136 sq ft
|House
17870 SE 92ND AMORY AVE, THE VILLAGES, F...
Community: The Villages®
MLS G5109643 • FLORIDA FINE HOMES REALTY, LLC, Ca...
Cresswind DeLand
![1293 TWIN FARMS CT, DELAND, FL, 32724, Deland, FL 32724]()
2 beds
|2 baths
|2,029 sq ft
|House
1293 TWIN FARMS CT, DELAND, FL, 32724
Community: Cresswind DeLand
MLS W7884833 • MALTBIE REALTY GROUP, Bill Maltbie
Sullivan Ranch
![30139 HACKNEY LOOP, MOUNT DORA, FL, 3275..., Mount Dora, FL 32757]()
4 beds
|3 baths
|2,432 sq ft
|House
30139 HACKNEY LOOP, MOUNT DORA, FL, 3275...
Community: Sullivan Ranch
MLS O6395484 • CREEGAN GROUP, Brad Corbitt
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 O6398567 • RE/MAX TOWN & COUNTRY REALTY, Domi...
The Villages®
![1251 EUREKA MILL RUN, THE VILLAGES, FL, ..., The Villages, FL 32162]()
3 beds
|2 baths
|2,000 sq ft
|House
1251 EUREKA MILL RUN, THE VILLAGES, FL, ...
Community: The Villages®
MLS G5110689 • 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.
Spruce Creek South
![10622 SE 179TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,450 sq ft
|House
10622 SE 179TH LN, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
MLS G5110876 • FLORIDA FINE HOMES REALTY, LLC, Pa...
The Villages®
![2849 LEICESTER TER, THE VILLAGES, FL, 32..., The Villages, FL 32162]()
3 beds
|2 baths
|1,413 sq ft
|Villa
2849 LEICESTER TER, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5110836 • REALTY EXECUTIVES IN THE VILLAGES,...
The Country Club of Mount Dora
![1880 EDGEWATER DR, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
3 beds
|2 baths
|2,343 sq ft
|House
1880 EDGEWATER DR, MOUNT DORA, FL, 32757
Community: The Country Club of Mount Dora
MLS G5110379 • COUNTRY CLUB LIFESTYLE PROPERTIES,...
The Villages®
![17830 SE 88TH CASCADE CT, THE VILLAGES, ..., The Villages, FL 32162]()
3 beds
|2 baths
|1,485 sq ft
|House
17830 SE 88TH CASCADE CT, THE VILLAGES, ...
Community: The Villages®
MLS G5110959 • REALTY EXECUTIVES IN THE VILLAGES,...
The Villages®
![416 CARRERA DR, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|2,006 sq ft
|House
416 CARRERA DR, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5110213 • RE/MAX PREMIER REALTY, Guy William...
Arlington Ridge
![4401 POPLAR GROVE CT, LEESBURG, FL, 3474..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,892 sq ft
|House
4401 POPLAR GROVE CT, LEESBURG, FL, 3474...
Community: Arlington Ridge
MLS G5110980 • LOKATION, Steven Simpkins
Want to learn more about 55+ communities in Winter Park?
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The Villages®
![1609 BLOSSOM TER, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
1609 BLOSSOM TER, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5110982 • LPT REALTY, LLC, Lena Morgan
Kings Ridge
![4364 SAMBOURNE ST, CLERMONT, FL, 34711, Clermont, FL 34711]()
2 beds
|2 baths
|1,446 sq ft
|House
4364 SAMBOURNE ST, CLERMONT, FL, 34711
Community: Kings Ridge
MLS G5110949 • KELLER WILLIAMS ELITE PARTNERS III...
The Villages®
![270 MATISSE AVE, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|2,075 sq ft
|House
270 MATISSE AVE, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5110907 • REALTY EXECUTIVES IN THE VILLAGES,...
Halifax Plantation
![1328 ANTRIM CIR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,499 sq ft
|House
1328 ANTRIM CIR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
MLS 1225203 • RE/MAX Signature, David Lieb
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.
Lakeside Landings
![10174 LAKE MIONA WAY, OXFORD, FL, 34484, Oxford, FL 34484]()
3 beds
|2 baths
|1,927 sq ft
|House
10174 LAKE MIONA WAY, OXFORD, FL, 34484
Community: Lakeside Landings
MLS OM722628 • SALLY LOVE REAL ESTATE, Star Amado...
The Villages®
![1460 CRESTWOOD LN, THE VILLAGES, FL, 321..., The Villages, FL 32162]()
2 beds
|2 baths
|1,156 sq ft
|Villa
1460 CRESTWOOD LN, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5110975 • LPT REALTY, LLC, Lena Morgan
Del Webb Sunbridge
![2873 CHERRY BLOSSOM LOOP, ST CLOUD, FL, ..., St Cloud, FL 34771]()
3 beds
|3 baths
|2,270 sq ft
|House
2873 CHERRY BLOSSOM LOOP, ST CLOUD, FL, ...
Community: Del Webb Sunbridge
MLS O6398185 • INTERNATIONAL TEAM INC, Jo Costa
Arlington Ridge
![26605 AUGUSTA SPRINGS CIR, LEESBURG, FL,..., Leesburg, FL 34748]()
3 beds
|2 baths
|2,236 sq ft
|House
26605 AUGUSTA SPRINGS CIR, LEESBURG, FL,...
Community: Arlington Ridge
MLS O6398713 • FLORIDA REALTY INVESTMENTS, Kristi...
The Villages®
![16852 SE 96TH CHAPELWOOD CIR, THE VILLAG..., The Villages, FL 32162]()
2 beds
|2 baths
|1,353 sq ft
|House
16852 SE 96TH CHAPELWOOD CIR, THE VILLAG...
Community: The Villages®
MLS OM722566 • JUDY L. TROUT REALTY, Judy Trout
The Villages®
![1479 GEORGETOWN AVE, THE VILLAGES, FL, 3..., The Villages, FL 32162]()
MLS A12000001 • Compass Florida, LLC, Yvette Tole...
Highland Fairways
![2140 GRAND CYPRESS DR, LAKELAND, FL, 338..., Lakeland, FL 33810]()
2 beds
|2 baths
|1,394 sq ft
|House
2140 GRAND CYPRESS DR, LAKELAND, FL, 338...
Community: Highland Fairways
MLS TB8489813 • UNIVERSITY REALTY OF TAMPA, Rober...
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The Villages®
![437 JARQUIN WAY, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,161 sq ft
|Villa
437 JARQUIN WAY, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5109946 • RE/MAX PREMIER REALTY LADY LK, Nao...
Spruce Creek Country Club
![13524 SE 87TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,998 sq ft
|House
13524 SE 87TH CIR, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS 1074470 • Noble & Co. R.E. Professionals, Cou...
Baytree
![116 BAYTREE BLVD, TAVARES, FL, 32778, Tavares, FL 32778]()
MLS G5110641 • COLDWELL BANKER VANGUARD EDGE, Aly...
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®
![16980 SE 96TH CHAPELWOOD CIR, THE VILLAG..., The Villages, FL 32162]()
2 beds
|2 baths
|1,148 sq ft
|House
16980 SE 96TH CHAPELWOOD CIR, THE VILLAG...
Community: The Villages®
MLS OM722622 • RE/MAX ALLSTARS REALTY, Christie C...
The Villages®
![2334 ROSE ARBOR ST, THE VILLAGES, FL, 32..., The Villages, FL 32163]()
3 beds
|2 baths
|1,695 sq ft
|Villa
2334 ROSE ARBOR ST, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5110921 • LPT REALTY, LLC, Rick McKean
Cresswind at Victoria Gardens
![115 AVENHAM DR, DELAND, FL, 32724, Deland, FL 32724]()
3 beds
|2 baths
|1,687 sq ft
|House
115 AVENHAM DR, DELAND, FL, 32724
Community: Cresswind at Victoria Gardens
MLS V4948460 • GLORY INTL. REAL ESTATE CO, Codie ...
The Villages®
![1832 HARTFORD PATH, THE VILLAGES, FL, 32..., The Villages, FL 32162]()
3 beds
|2 baths
|2,502 sq ft
|House
1832 HARTFORD PATH, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5110809 • SALLY LOVE REAL ESTATE, Kim Coffer
The Villages®
![1017 PINEWOOD PL, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
2 beds
|2 baths
|1,156 sq ft
|Villa
1017 PINEWOOD PL, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5110363 • RE/MAX PREMIER REALTY LADY LK, Lyn...
Cresswind at Victoria Gardens
![307 HERON POINT WAY, DELAND, FL, 32724, Deland, FL 32724]()
2 beds
|2 baths
|1,547 sq ft
|House
307 HERON POINT WAY, DELAND, FL, 32724
Community: Cresswind at Victoria Gardens
MLS V4948459 • RISE REALTY OF FLORIDA LLC, Alex H...
Spruce Creek Country Club
![9570 SE 136TH PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
2 beds
|2 baths
|1,528 sq ft
|House
9570 SE 136TH PL, SUMMERFIELD, FL, 34491
Community: Spruce Creek Country Club
MLS OM722590 • REALTY ONE GROUP DAVALLS, David St...
The Villages®
![1469 RAMON RD, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,562 sq ft
|House
1469 RAMON RD, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5110080 • REALTY EXECUTIVES IN THE VILLAGES,...
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The Lakes at Harmony
![3113 SONGBIRD CIR, ST CLOUD, FL, 34773, St Cloud, FL 34773]()
3 beds
|2 baths
|1,876 sq ft
|House
3113 SONGBIRD CIR, ST CLOUD, FL, 34773
Community: The Lakes at Harmony
MLS S5146996 • CORCORAN CONNECT LLC, Jeanine Corc...
Bridgewater at Viera
![2478 MILLENNIUM CIR, MELBOURNE, FL, 3294..., Melbourne, FL 32940]()
3 beds
|3 baths
|2,453 sq ft
|House
2478 MILLENNIUM CIR, MELBOURNE, FL, 3294...
Community: Bridgewater at Viera
MLS 1074427 • HomeSmart Coastal Realty, Stephen N...
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.
