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Winter Park, FL 55+ active adult communities & homes for sale - Page 11
95 communities near Winter Park
2,259 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
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
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
$300ks
- $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale
|
Age-targeted
|
Built 2004 - present
|
1,561 homes
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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 (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)
![Stonecrest]()
$200ks
- $500ks
Stonecrest, Summerfield, FL
Resale Only
|
55+ age-restricted
|
Built 1990 - 2024
|
2,224 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
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
- $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1980 - present
|
1,000 homes
5 rating (8 reviews)
![Royal Highlands]()
$200ks
- $400ks
Royal Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2006
|
1,500 homes
$100ks
- $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only
|
Age-targeted
|
Built 1980 - 2006
|
1,806 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
3.8 rating (6 reviews)
![Trilogy® Orlando]()
$200ks
- $500ks
Trilogy® Orlando, Groveland, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2022
|
1,500 homes
2.8 rating (6 reviews)
![Arlington Ridge]()
$200ks
- $500ks
Arlington Ridge, Leesburg, FL
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
629 homes
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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
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
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
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
$400ks
- $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1985 - present
|
976 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)
![Royal Harbor]()
$200ks
- $800ks
Royal Harbor, Tavares, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2008
|
755 homes
1 rating (1 reviews)
![Sullivan Ranch]()
$200ks
- $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2020
|
692 homes
4.8 rating (6 reviews)
![Highland Lakes]()
$100ks
- $200ks
Highland Lakes, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1990 - 1999
|
938 homes
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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
$200ks
- $400ks
Summer Trees, Port Orange, FL
Resale Only
|
55+ age-restricted
|
Built 1976 - 2005
|
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
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.
$200ks
- $400ks
The Lakes at Harmony, Harmony, FL
New and Resale
|
55+ age-restricted
|
Built 2016 - present
|
400 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
$200ks
- $1Ms
The Country Club of Mount..., Mount Dora, FL
Resale Only
|
Age-targeted
|
Built 1991 - 2005
|
827 homes
$100ks
- $200ks
Foxwood Lake Estates, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1982 - 1987
|
545 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
$300ks
- $400ks
Gatherings of Lake Nona, Orlando, FL
New and Resale
|
55+ age-restricted
|
Built 2017 - present
|
216 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
$200ks
- $500ks
The Timbers at Everlands, Palm Bay, FL
New Construction
|
55+ age-restricted
|
Built 2023 - present
|
450 homes
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Questions? Call us:
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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
Scottish Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1983 - 1992
|
653 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.
Venetian Bay
![3321 MARSILI AVE, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
4 beds
|3 baths
|2,540 sq ft
|House
3321 MARSILI AVE, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS NS1088502 • COLLADO REAL ESTATE, Pat Collado
Pennbrooke Fairways
![32222 SUMMERTREE CIR, LEESBURG, FL, 3474..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,725 sq ft
|House
32222 SUMMERTREE CIR, LEESBURG, FL, 3474...
Community: Pennbrooke Fairways
MLS G5113595 • KELLER WILLIAMS ELITE PARTNERS III...
Spruce Creek Country Club
![9119 SE 120TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,488 sq ft
|House
9119 SE 120TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek Country Club
MLS O6418689 • REGENCY REAL ESTATE LLC, Evelyn Te...
The Villages®
![1726 HILTON HEAD BLVD, LADY LAKE, FL, 32..., Lady Lake, FL 32159]()
2 beds
|2 baths
|1,290 sq ft
|Manufactured Home
1726 HILTON HEAD BLVD, LADY LAKE, FL, 32...
Community: The Villages®
MLS G5114051 • EXP REALTY LLC, Michael Barbier
The Villages®
![3394 RANDI RD, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|1,810 sq ft
|Villa
3394 RANDI RD, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5114046 • SALLY LOVE REAL ESTATE, Sally Love
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The Villages®
![1132 MAYNARD PATH, THE VILLAGES, FL, 321..., The Villages, FL 32163]()
3 beds
|3 baths
|1,901 sq ft
|House
1132 MAYNARD PATH, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5113873 • REALTY EXECUTIVES IN THE VILLAGES,...
Vienna Square
![2452 SALZBURG LOOP, WINTER HAVEN, FL, 33..., Winter Haven, FL 33884]()
2 beds
|2 baths
|1,729 sq ft
|House
2452 SALZBURG LOOP, WINTER HAVEN, FL, 33...
Community: Vienna Square
MLS L4962907 • AMPLIFY REAL ESTATE SERVICES FL, N...
Venetian Bay
![424 LUNA BELLA LN 231, NEW SMYRNA BEACH,..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|1,953 sq ft
|Condo
424 LUNA BELLA LN 231, NEW SMYRNA BEACH,...
Community: Venetian Bay
MLS NS1088282 • NSB HOMES LLC, Donna Concannon
Solivita
![505 MILLIFIORA LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS P4939099 • EXP REALTY LLC, Michael Jacobs
Legacy of Leesburg
![27134 NOSTALGIA DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,601 sq ft
|House
27134 NOSTALGIA DR, LEESBURG, FL, 34748
Community: Legacy of Leesburg
MLS G5114067 • KELLER WILLIAMS ELITE PARTNERS III...
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.
Scottish Highlands
![1 DURNESS CT, LEESBURG, FL, 34788, Leesburg, FL 34788]()
2 beds
|2 baths
|1,200 sq ft
|House
1 DURNESS CT, LEESBURG, FL, 34788
Community: Scottish Highlands
MLS G5113947 • FLORIDA FINE HOMES REALTY, LLC, Ca...
Legacy of Leesburg
![5127 AURORA DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|2,386 sq ft
|House
5127 AURORA DR, LEESBURG, FL, 34748
Community: Legacy of Leesburg
MLS O6418513 • MARK SPAIN REAL ESTATE, Charles Wa...
Breakaway Trails
![9 COQUINA RIDGE WAY, ORMOND BEACH, FL, 3..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,605 sq ft
|House
9 COQUINA RIDGE WAY, ORMOND BEACH, FL, 3...
Community: Breakaway Trails
MLS 1227750 • RE/MAX Signature, Karin Udolf Strob...
Spruce Creek South
![17584 SE 105TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,144 sq ft
|House
17584 SE 105TH TER, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
MLS G5114005 • RE/MAX PREMIER REALTY LADY LK, Ger...
Harbor Hills Country Club
![5506 CITATION CT, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
3 beds
|3 baths
|2,698 sq ft
|House
5506 CITATION CT, LADY LAKE, FL, 32159
Community: Harbor Hills Country Club
MLS G5113948 • MORRIS REALTY AND INVESTMENTS, The...
Halifax Plantation
![3749 BELFAST CIR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,432 sq ft
|House
3749 BELFAST CIR, ORMOND BEACH, FL, 3217...
Community: Halifax Plantation
MLS 1227731 • Century 21 Sundance Realty, Carolyn...
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Stonecrest
![17719 SE 114TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,704 sq ft
|Villa
17719 SE 114TH CT, SUMMERFIELD, FL, 3449...
Community: Stonecrest
MLS G5113536 • BASSETT PREMIER REALTY INC, Sharon...
The Timbers at Everlands
![2439 CYAN PL, PALM BAY, FL, 32907, Palm Bay, FL 32907]()
3 beds
|2 baths
|1,758 sq ft
|House
2439 CYAN PL, PALM BAY, FL, 32907
Community: The Timbers at Everlands
MLS 1080515 • Lennar Realty, Inc., Jennifer Riche...
Grand Haven
![22 IBIS CT N, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
MLS 1227726 • Tavolacci Realty, Inc, Joseph Tavol...
Del Webb Sunbridge
![6524 SHIMMERING SHORES LN, ST CLOUD, FL,..., St Cloud, FL 34771]()
3 beds
|4 baths
|2,808 sq ft
|House
6524 SHIMMERING SHORES LN, ST CLOUD, FL,...
Community: Del Webb Sunbridge
MLS TB8518894 • EXP REALTY LLC, Peter Bonanno
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.
Heritage - The Cottages of Sanders Grove
![6213 SANDERS GROVE CIR, OKAHUMPKA, FL, 3..., Okahumpka, FL 34762]()
4 beds
|2 baths
|1,625 sq ft
|House
6213 SANDERS GROVE CIR, OKAHUMPKA, FL, 3...
Community: Heritage - The Cottages of Sanders Grove
MLS G5113907 • OLYMPUS EXECUTIVE REALTY INC, Nanc...
Heritage - The Cottages of Sanders Grove
![6217 SANDERS GROVE CIR, OKAHUMPKA, FL, 3..., Okahumpka, FL 34762]()
4 beds
|3 baths
|1,938 sq ft
|House
6217 SANDERS GROVE CIR, OKAHUMPKA, FL, 3...
Community: Heritage - The Cottages of Sanders Grove
MLS G5113912 • OLYMPUS EXECUTIVE REALTY INC, Nanc...
Heritage - The Cottages of Sanders Grove
![5715 HIAWASSEE RD, OKAHUMPKA, FL, 34762, Okahumpka, FL 34762]()
4 beds
|3 baths
|1,938 sq ft
|House
5715 HIAWASSEE RD, OKAHUMPKA, FL, 34762
Community: Heritage - The Cottages of Sanders Grove
MLS G5113916 • OLYMPUS EXECUTIVE REALTY INC, Nanc...
Heritage - The Cottages of Sanders Grove
![6205 SANDERS GROVE CIR, OKAHUMPKA, FL, 3..., Okahumpka, FL 34762]()
3 beds
|2 baths
|1,407 sq ft
|House
6205 SANDERS GROVE CIR, OKAHUMPKA, FL, 3...
Community: Heritage - The Cottages of Sanders Grove
MLS G5113773 • OLYMPUS EXECUTIVE REALTY INC, Nanc...
Huntington at Hunter's Ridge
![55 HUNTINGTON PL, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
4 beds
|2 baths
|1,974 sq ft
|House
55 HUNTINGTON PL, ORMOND BEACH, FL, 3217...
Community: Huntington at Hunter's Ridge
MLS V4949746 • SIMPLY REAL ESTATE, Geri Westfall ...
The Villages®
![2752 CRAVEN WAY, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,156 sq ft
|Villa
2752 CRAVEN WAY, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5113763 • KELLER WILLIAMS CORNERSTONE RE, Ka...
The Villages®
![1516 MARTINEZ DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|1,546 sq ft
|Villa
1516 MARTINEZ DR, LADY LAKE, FL, 32159
Community: The Villages®
MLS G5113765 • KELLER WILLIAMS CORNERSTONE RE, Ka...
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Heritage - The Cottages of Sanders Grove
![5719 HIAWASSEE RD, OKAHUMPKA, FL, 34762, Okahumpka, FL 34762]()
4 beds
|2 baths
|1,625 sq ft
|House
5719 HIAWASSEE RD, OKAHUMPKA, FL, 34762
Community: Heritage - The Cottages of Sanders Grove
MLS G5113918 • OLYMPUS EXECUTIVE REALTY INC, Nanc...
The Villages®
![2132 SANSORES ST, THE VILLAGES, FL, 3215..., The Villages, FL 32159]()
3 beds
|2 baths
|1,916 sq ft
|House
2132 SANSORES ST, THE VILLAGES, FL, 3215...
Community: The Villages®
MLS G5113068 • RE/MAX FOXFIRE - SUMMERFIELD, Kell...
Grand Haven
![22 IBIS CT, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
MLS FC319206 • TAVOLACCI REALTY, Denise Gallo
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
![3916 SCARBOROUGH CT, CLERMONT, FL, 34711, Clermont, FL 34711]()
3 beds
|2 baths
|2,147 sq ft
|House
3916 SCARBOROUGH CT, CLERMONT, FL, 34711
Community: Kings Ridge
MLS G5113844 • REAL BROKER, LLC, Diane Rogers
Twin Lakes
![2841 MIDSWEET AVE, ST CLOUD, FL, 34772, St Cloud, FL 34772]()
MLS O6418332 • PULTE REALTY OF NORTH FLORIDA LLC,...
The Villages®
![1492 OLUSTEE PL, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|1,917 sq ft
|House
1492 OLUSTEE PL, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5113646 • REALTY EXECUTIVES IN THE VILLAGES,...
Kings Ridge
![2265 CALVERT CT, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS G5113837 • REAL BROKER, LLC, Diane Rogers
Twin Lakes
![5042 DANCY LN, ST CLOUD, FL, 34772, St Cloud, FL 34772]()
MLS O6418328 • PULTE REALTY OF NORTH FLORIDA LLC,...
Arlington Ridge
![27001 WHITE PLAINS WAY, LEESBURG, FL, 34..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,330 sq ft
|Villa
27001 WHITE PLAINS WAY, LEESBURG, FL, 34...
Community: Arlington Ridge
MLS G5113991 • ROBERT SLACK LLC, Sid Benachenhou
Silver Lakes
![2258 SILVER RE DR, LAKELAND, FL, 33810, Lakeland, FL 33810]()
3 beds
|2 baths
|1,355 sq ft
|House
2258 SILVER RE DR, LAKELAND, FL, 33810
Community: Silver Lakes
MLS L4962666 • TRUE FLORIDA REALTY LLC, Marilyn D...
The Villages®
![1260 GRANADA CT, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|1,541 sq ft
|House
1260 GRANADA CT, LADY LAKE, FL, 32159
Community: The Villages®
MLS G5113972 • RE/MAX SELECT PARTNERS, Renee Hous...
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The Villages®
![2453 VIOLET CT, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,398 sq ft
|Villa
2453 VIOLET CT, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5113998 • LPT REALTY, LLC, Vickie Couture
Colonnades
![4918 PLEASANT HOLLOW TRL, LAKELAND, FL, ..., Lakeland, FL 33811]()
2 beds
|2 baths
|1,123 sq ft
|House
4918 PLEASANT HOLLOW TRL, LAKELAND, FL, ...
Community: Colonnades
MLS L4962797 • KELLER WILLIAMS REALTY SMART, Ashl...
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?
2,259
homes
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REIN updates its listings on a daily basis. Data last updated: Jul 10, 2026.
This application does not include information on all of the properties available for sale at this time.
