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Winter Park, FL 55+ active adult communities & homes for sale - Page 14
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
Want to learn more about 55+ communities in Winter Park?
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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.
Twin Lakes
![2286 DATURA LOOP, ST CLOUD, FL, 34772, St Cloud, FL 34772]()
MLS S5148930 • 365 REALTY, INC., Robert Benenati
The Villages®
![2859 RESMONDO RD, THE VILLAGES, FL, 3216..., The Villages, FL 32163]()
3 beds
|2 baths
|1,674 sq ft
|Villa
2859 RESMONDO RD, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5110714 • LPT REALTY, LLC, Kristi CHRISTMAN
Spruce Creek Country Club
![9280 SE 126TH ST, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
2 beds
|3 baths
|2,368 sq ft
|House
9280 SE 126TH ST, SUMMERFIELD, FL, 34491
Community: Spruce Creek Country Club
MLS OM723442 • BROKER ASSOCIATES REALTY, Rich Den...
Latitude Margaritaville
![219 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,464 sq ft
|House
219 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F...
Community: Latitude Margaritaville
MLS 1225852 • RE/MAX Signature, Karen Basak-Carey
Pennbrooke Fairways
![32676 OAK PARK DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,709 sq ft
|House
32676 OAK PARK DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS G5111662 • REALTY EXECUTIVES IN THE VILLAGES,...
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Palms at Serenoa
![3421 TWIN FLOWER, CLERMONT, FL, 34714, Clermont, FL 34714]()
2 beds
|2 baths
|1,627 sq ft
|Villa
3421 TWIN FLOWER, CLERMONT, FL, 34714
Community: Palms at Serenoa
MLS O6400931 • IVRE ORLANDO, Janet Hepburn
The Villages®
![2612 MORVEN PARK WAY, THE VILLAGES, FL, ..., The Villages, FL 32162]()
3 beds
|2 baths
|1,922 sq ft
|House
2612 MORVEN PARK WAY, THE VILLAGES, FL, ...
Community: The Villages®
MLS O6403402 • RE/MAX 200 REALTY, Tom Langmann
Grand Haven
![6 RIVER POINT DR, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
2 beds
|3 baths
|2,201 sq ft
|Townhouse
6 RIVER POINT DR, PALM COAST, FL, 32137
Community: Grand Haven
MLS FC318124 • COASTAL GATEWAY REAL ESTATE GR, Cy...
Spruce Creek Country Club
![9175 SE 118TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,488 sq ft
|House
9175 SE 118TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek Country Club
MLS O6403281 • REALTY HUB, James Sparkman
The Villages®
![300 VARNVILLE WAY, THE VILLAGES, FL, 321..., The Villages, FL 32162]()
2 beds
|2 baths
|1,266 sq ft
|Villa
300 VARNVILLE WAY, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5111449 • EXP REALTY LLC, Elizabeth Pabon-Ha...
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®
![963 AVALON AVE, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,268 sq ft
|Villa
963 AVALON AVE, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5111633 • REALTY EXECUTIVES IN THE VILLAGES,...
Foxwood Lake Estates
![1688 FOXWAY DR, LAKELAND, FL, 33810, Lakeland, FL 33810]()
3 beds
|2 baths
|1,427 sq ft
|Manufactured Home
1688 FOXWAY DR, LAKELAND, FL, 33810
Community: Foxwood Lake Estates
MLS P4938590 • FLORIDA REALTY MARKETPLACE, Debra ...
Sandpiper Golf & Country Club
![6347 EGRET DR, LAKELAND, FL, 33809, Lakeland, FL 33809]()
2 beds
|2 baths
|1,028 sq ft
|House
6347 EGRET DR, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS L4961459 • REMAX EXPERTS, Diana Brown
Twin Lakes
![2305 DATURA LOOP, ST CLOUD, FL, 34772, St Cloud, FL 34772]()
MLS S5148779 • FLORIDA INT'NL REAL ESTATE LLC, Li...
Plantation Bay Golf & Country Club
![1269 HARWICK LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|2 baths
|2,148 sq ft
|House
1269 HARWICK LN, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS FC318117 • GRAND LIVING REALTY, Suzanne Johns...
Ridgehaven
![408 BROOKHAVEN TRL, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,791 sq ft
|House
408 BROOKHAVEN TRL, ORMOND BEACH, FL, 32...
Community: Ridgehaven
MLS 1225837 • Meritage Homes of Florida Realty LL...
Want to learn more about 55+ communities in Winter Park?
55places can help!
Questions? Call us:
(888) 625-4885
Royal Highlands
![21630 REGENCY PARK LN, LEESBURG, FL, 347..., Leesburg, FL 34748]()
3 beds
|2 baths
|1,438 sq ft
|House
21630 REGENCY PARK LN, LEESBURG, FL, 347...
Community: Royal Highlands
MLS O6402529 • RE/MAX TOWN & COUNTRY REALTY, Kell...
Foxwood Lake Estates
![1502 LONGBOW DR, LAKELAND, FL, 33810, Lakeland, FL 33810]()
2 beds
|2 baths
|1,144 sq ft
|Manufactured Home
1502 LONGBOW DR, LAKELAND, FL, 33810
Community: Foxwood Lake Estates
MLS L4961474 • KELLER WILLIAMS REALTY SMART, Ashl...
Lake James
![7991 LAKE JAMES BLVD, LAKELAND, FL, 3381..., Lakeland, FL 33810]()
2 beds
|2 baths
|1,890 sq ft
|House
7991 LAKE JAMES BLVD, LAKELAND, FL, 3381...
Community: Lake James
MLS TB8502616 • KELLER WILLIAMS SUBURBAN TAMPA, C...
The Villages®
![1627 KENSINGTON PL, THE VILLAGES, FL, 32..., The Villages, FL 32162]()
3 beds
|2 baths
|1,912 sq ft
|House
1627 KENSINGTON PL, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5111464 • LPT REALTY, LLC, Lena Morgan
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.
Venetian Bay
![424 LUNA BELLA LN 228, NEW SMYRNA BEACH,..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|2,030 sq ft
|Condo
424 LUNA BELLA LN 228, NEW SMYRNA BEACH,...
Community: Venetian Bay
MLS NS1088049 • COLLADO REAL ESTATE, Laura Imbria...
Grand Isle
![1611 LAGO MAR DR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
MLS 1075751 • Dalton Wade, Inc., Matthew R Stebbi...
The Villages®
![1404 BRIER CREEK CIR, THE VILLAGES, FL, ..., The Villages, FL 32162]()
4 beds
|3 baths
|3,537 sq ft
|House
1404 BRIER CREEK CIR, THE VILLAGES, FL, ...
Community: The Villages®
MLS G5111607 • COLDWELL BANKER VANGUARD LIFESTYLE...
The Villages®
![2837 GRANT WAY, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,923 sq ft
|House
2837 GRANT WAY, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5111506 • COLDWELL BANKER VANGUARD LIFESTYLE...
The Villages®
![6231 ATKINSON LN, THE VILLAGES, FL, 3216..., The Villages, FL 32163]()
3 beds
|2 baths
|1,426 sq ft
|House
6231 ATKINSON LN, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5111501 • EXP REALTY LLC, John Burgfechtel
Solivita
![537 GRAND CANAL DR, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5148682 • BORCHINI REALTY, Charles Borchini
Halifax Plantation
![2853 MONAGHAN DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,115 sq ft
|House
2853 MONAGHAN DR, ORMOND BEACH, FL, 3217...
Community: Halifax Plantation
MLS 1225800 • Florida Bluewater Realty LLC, Natha...
Want to learn more about 55+ communities in Winter Park?
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(888) 625-4885
Del Webb Orlando
![436 PONTEVEDRA RD, DAVENPORT, FL, 33837, Davenport, FL 33837]()
2 beds
|2 baths
|1,348 sq ft
|House
436 PONTEVEDRA RD, DAVENPORT, FL, 33837
Community: Del Webb Orlando
MLS OM723730 • AMPUERO REALTY CORP., Gloria Ampue...
Lakeside Landings
![5425 ADMIRAL WAY 1, OXFORD, FL, 34484, Oxford, FL 34484]()
2 beds
|2 baths
|1,281 sq ft
|Condo
5425 ADMIRAL WAY 1, OXFORD, FL, 34484
Community: Lakeside Landings
MLS O6402747 • MARCILLO REAL ESTATE LLC, Dalia Ro...
Plantation at Leesburg
![4908 CYPRESS HEAD CT, LEESBURG, FL, 3474..., Leesburg, FL 34748]()
3 beds
|2 baths
|2,087 sq ft
|House
4908 CYPRESS HEAD CT, LEESBURG, FL, 3474...
Community: Plantation at Leesburg
MLS G5111653 • RE/MAX REALTY UNLIMITED, Tammy Cam...
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®
![1603 COG HILL DR, THE VILLAGES, FL, 3215..., The Villages, FL 32159]()
2 beds
|2 baths
|1,542 sq ft
|Manufactured Home
1603 COG HILL DR, THE VILLAGES, FL, 3215...
Community: The Villages®
MLS O6390602 • WEMERT GROUP REALTY LLC, Jenny Wem...
The Villages®
![8329 SE 177TH BARTRAM LOOP, THE VILLAGES..., The Villages, FL 32162]()
3 beds
|2 baths
|1,668 sq ft
|House
8329 SE 177TH BARTRAM LOOP, THE VILLAGES...
Community: The Villages®
MLS G5111679 • REALTY EXECUTIVES IN THE VILLAGES,...
Spruce Creek Country Club
![13150 SE 93RD CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|2,051 sq ft
|House
13150 SE 93RD CIR, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS OM722715 • NEXT GENERATION REALTY OF MARION C...
The Villages®
![2766 PRIVADA DR, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,664 sq ft
|House
2766 PRIVADA DR, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5111510 • REALTY EXECUTIVES IN THE VILLAGES,...
The Villages®
![2918 CANYON AVE, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|2,013 sq ft
|House
2918 CANYON AVE, THE VILLAGES, FL, 32163
Community: The Villages®
MLS O6401444 • REDFIN CORPORATION, Jo Holton
Pelican Bay Daytona Beach
![120 SEA SPARROW CT, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32119]()
3 beds
|2 baths
|2,252 sq ft
|House
120 SEA SPARROW CT, DAYTONA BEACH, FL, 3...
Community: Pelican Bay Daytona Beach
MLS FC316850 • LPT REALTY LLC (DB), Joy Pratt-Mar...
Foxwood Lake Estates
![5091 LODGEWOOD DR, LAKELAND, FL, 33810, Lakeland, FL 33810]()
2 beds
|2 baths
|1,152 sq ft
|Manufactured Home
5091 LODGEWOOD DR, LAKELAND, FL, 33810
Community: Foxwood Lake Estates
MLS P4938574 • FLORIDA REALTY MARKETPLACE, Debra ...
The Villages®
![3064 MAYWOOD CT, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,517 sq ft
|House
3064 MAYWOOD CT, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5111631 • REALTY EXECUTIVES IN THE VILLAGES,...
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Bridgewater at Viera
![9893 ALISTER DR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|2 baths
|1,565 sq ft
|House
9893 ALISTER DR, MELBOURNE, FL, 32940
Community: Bridgewater at Viera
MLS 1075840 • Coldwell Banker Realty, Glenn Teed
Halifax Plantation
![3231 GALTY CIR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
2 beds
|2 baths
|1,943 sq ft
|House
3231 GALTY CIR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
MLS 1225753 • EXP Realty LLC, Jeff Dillard
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.
