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 61
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
Want to learn more about 55+ communities in Winter Park?
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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
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.
Halifax Plantation
![3404 REXFORD CIR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
3 beds
|3 baths
|2,586 sq ft
|House
3404 REXFORD CIR, ORMOND BEACH, FL, 3217...
Community: Halifax Plantation
MLS FC305300 • ONE SOTHEBYS INTERNATIONAL, Kory L...
Vienna Square
![1561 VIENNA SQUARE DR, WINTER HAVEN, FL,..., Winter Haven, FL 33884]()
2 beds
|2 baths
|1,231 sq ft
|Villa
1561 VIENNA SQUARE DR, WINTER HAVEN, FL,...
Community: Vienna Square
MLS P4932767 • FLORIDA HOME CHOICE REALTY, Glenda...
Spruce Creek South
![17855 SE 99TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,678 sq ft
|House
17855 SE 99TH AVE, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
MLS OM689620 • JUDY L. TROUT REALTY, Jennifer Tra...
Alhambra Villas Condominiums
![201 N HILL AVE 150, DELAND, FL, 32724, Deland, FL 32724]()
2 beds
|2 baths
|1,090 sq ft
|Condo
201 N HILL AVE 150, DELAND, FL, 32724
Community: Alhambra Villas Condominiums
MLS V4939262 • UNITED REAL ESTATE PREFERRED, Chri...
Trilogy® Orlando
![119 CRESCENT MOON DR, GROVELAND, FL, 347..., Groveland, FL 34736]()
2 beds
|2 baths
|1,556 sq ft
|House
119 CRESCENT MOON DR, GROVELAND, FL, 347...
Community: Trilogy® Orlando
MLS G5088807 • WEICHERT, REALTORS-HALLMARK PR, Br...
Want to learn more about 55+ communities in Winter Park?
55places can help!
Questions? Call us:
(888) 625-4885
Twin Lakes
![2717 GREENLANDS ST, ST CLOUD, FL, 34772, St Cloud, FL 34772]()
3 beds
|2 baths
|1,863 sq ft
|House
2717 GREENLANDS ST, ST CLOUD, FL, 34772
Community: Twin Lakes
MLS O6245416 • KELLER WILLIAMS WINTER PARK, Manny...
Highland Fairways
![1967 LONG BOAT DR, LAKELAND, FL, 33810, Lakeland, FL 33810]()
2 beds
|2 baths
|1,955 sq ft
|House
1967 LONG BOAT DR, LAKELAND, FL, 33810
Community: Highland Fairways
MLS U8253025 • FUTURE HOME REALTY INC, Frank Poll...
Foxwood Lake Estates
![5013 FOXWOOD BLVD, LAKELAND, FL, 33810, Lakeland, FL 33810]()
2 beds
|2 baths
|1,056 sq ft
|Manufactured Home
5013 FOXWOOD BLVD, LAKELAND, FL, 33810
Community: Foxwood Lake Estates
MLS S5108231 • BETTER HOMES & GARDENS RE LIFESTYL...
Pelican Bay Daytona Beach
![244 PALM SPARROW CT, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119]()
2 beds
|2 baths
|1,370 sq ft
|House
244 PALM SPARROW CT, DAYTONA BEACH, FL, ...
Community: Pelican Bay Daytona Beach
MLS 1117527 • Seemore Realty Group Inc., Judy Tin...
Indian River Colony Club
![1440 PATRIOT DR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
4 beds
|2 baths
|2,424 sq ft
|House
1440 PATRIOT DR, MELBOURNE, FL, 32940
Community: Indian River Colony Club
MLS 1017110 • Four Star Real Estate LLC, Shellie ...
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
![2323 DATURA LOOP, ST CLOUD, FL, 34772, St Cloud, FL 34772]()
MLS O6206746 • ORLANDO PROPERTY ADVISORS, Jessica...
Twin Lakes
![2410 DATURA LOOP, ST CLOUD, FL, 34772, St Cloud, FL 34772]()
MLS S5103150 • COLDWELL BANKER SOLOMON, Susy Orti...
High Vista at Ridgewood Lakes
![100 MOSS LN, DAVENPORT, FL, 33837, Davenport, FL 33837]()
3 beds
|2 baths
|2,051 sq ft
|House
100 MOSS LN, DAVENPORT, FL, 33837
Community: High Vista at Ridgewood Lakes
MLS S5101667 • KELLER WILLIAMS REALTY AT THE LAKE...
Alhambra Villas Condominiums
![217 N HILL AVE 20, DELAND, FL, 32724, Deland, FL 32724]()
2 beds
|2 baths
|1,066 sq ft
|Condo
217 N HILL AVE 20, DELAND, FL, 32724
Community: Alhambra Villas Condominiums
MLS V4934458 • UNITED REAL ESTATE PREFERRED, Chri...
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.
