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Winter Park, FL 55+ active adult communities & homes for sale - Page 55
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.
Kings Ridge
![3713 DOUNE WAY, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS O6348405 • FLORIDA PRESTIGIOUS HOMES INC, Ian...
Spruce Creek Country Club
![9244 SE 128TH ST, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
2 beds
|2 baths
|2,130 sq ft
|House
9244 SE 128TH ST, SUMMERFIELD, FL, 34491
Community: Spruce Creek Country Club
MLS OM710460 • RE/MAX FOXFIRE - SUMMERFIELD, Caro...
The Villages®
![3818 INFINITY RUN, THE VILLAGES, FL, 321..., The Villages, FL 32163]()
3 beds
|2 baths
|1,501 sq ft
|House
3818 INFINITY RUN, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5102409 • REALTY EXECUTIVES IN THE VILLAGES,...
Plantation Bay Golf & Country Club
![945 STONE LAKE DR, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,910 sq ft
|House
945 STONE LAKE DR, ORMOND BEACH, FL, 321...
Community: Plantation Bay Golf & Country Club
MLS FC313035 • VENTURE DEVELOPMENT REALTY,INC, El...
Cypress Lakes
![2247 CYPRESS CROSS LOOP, LAKELAND, FL, 3..., Lakeland, FL 33810]()
2 beds
|2 baths
|768 sq ft
|Manufactured Home
2247 CYPRESS CROSS LOOP, LAKELAND, FL, 3...
Community: Cypress Lakes
MLS L4956160 • KELLER WILLIAMS REALTY SMART, Casa...
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Colonnades
![4816 GOLDENVIEW LN, LAKELAND, FL, 33811, Lakeland, FL 33811]()
2 beds
|2 baths
|1,066 sq ft
|Manufactured Home
4816 GOLDENVIEW LN, LAKELAND, FL, 33811
Community: Colonnades
MLS L4955982 • COLDWELL BANKER REALTY, Lisa Broch...
Solivita
![189 GRAND CANAL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS O6347415 • KELLER WILLIAMS WINTER PARK, Jonat...
Heritage Isle
![3130 LE CONTE ST, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
2 beds
|2 baths
|1,394 sq ft
|Townhouse
3130 LE CONTE ST, MELBOURNE, FL, 32940
Community: Heritage Isle
MLS 1058050 • Blue Marlin Real Estate, Sarah Reka...
VillageWalk at Lake Nona
![12004 ULETA LN, ORLANDO, FL, 32827, Orlando, FL 32827]()
4 beds
|4 baths
|4,114 sq ft
|House
12004 ULETA LN, ORLANDO, FL, 32827
Community: VillageWalk at Lake Nona
MLS O6347169 • MS LAND & BUILDING LLC, Ataide Bra...
Lake Ashton
![4195 MUIRFIELD LOOP, LAKE WALES, FL, 338..., Lake Wales, FL 33859]()
3 beds
|2 baths
|2,039 sq ft
|House
4195 MUIRFIELD LOOP, LAKE WALES, FL, 338...
Community: Lake Ashton
MLS P4936379 • GLOBAL LIFESTYLE LLC, Brad Kirwan
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.
Vienna Square
![2470 SALZBURG LOOP, WINTER HAVEN, FL, 33..., Winter Haven, FL 33884]()
3 beds
|2 baths
|1,935 sq ft
|House
2470 SALZBURG LOOP, WINTER HAVEN, FL, 33...
Community: Vienna Square
MLS O6344501 • PREMIUM REAL ESTATE SERVICES, Nere...
Solivita
![428 BEL AIR WAY, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5134079 • BELLA VERDE REALTY LLC, Miguel Elv...
Stonecrest
![12163 SE 176TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491]()
3 beds
|2 baths
|2,645 sq ft
|House
12163 SE 176TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
MLS G5102452 • RE/MAX FOXFIRE - SUMMERFIELD, Cher...
Plantation Bay Golf & Country Club
![998 DOWNSHIRE LN, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
5 beds
|4 baths
|5,454 sq ft
|House
998 DOWNSHIRE LN, ORMOND BEACH, FL, 3217...
Community: Plantation Bay Golf & Country Club
MLS FC312940 • VENTURE DEVELOPMENT REALTY,INC, El...
Grand Haven
![200 RIVERFRONT DR B303, PALM COAST, FL, ..., Palm Coast, FL 32137]()
3 beds
|2 baths
|1,762 sq ft
|Condo
200 RIVERFRONT DR B303, PALM COAST, FL, ...
Community: Grand Haven
MLS FC312912 • TRADEMARK REALTY GROUP LLC, Bruce ...
Latitude Margaritaville
![299 POP TOP LN, DAYTONA BEACH, FL, 32124, Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,464 sq ft
|House
299 POP TOP LN, DAYTONA BEACH, FL, 32124
Community: Latitude Margaritaville
MLS 1218124 • Keller Williams Realty Florida Part...
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Latitude Margaritaville
![221 ISLAND BREEZE AVE, DAYTONA BEACH, FL..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,509 sq ft
|House
221 ISLAND BREEZE AVE, DAYTONA BEACH, FL...
Community: Latitude Margaritaville
MLS 1218111 • Bob Hodges and Sons Realty, Susan W...
The Villages®
![1712 MORELOS RD, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,193 sq ft
|Villa
1712 MORELOS RD, THE VILLAGES, FL, 32159
Community: The Villages®
MLS W7879135 • LISTWITHFREEDOM.COM, Ralph Harvey
Arlington Ridge
![26939 WHITE PLAINS WAY, LEESBURG, FL, 34..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,631 sq ft
|Villa
26939 WHITE PLAINS WAY, LEESBURG, FL, 34...
Community: Arlington Ridge
MLS G5102246 • HOAD REALTY GROUP LLC, Lisa Hoad
Heritage Hills
![3524 LITCHFIELD CT, CLERMONT, FL, 34711, Clermont, FL 34711]()
4 beds
|3 baths
|2,293 sq ft
|House
3524 LITCHFIELD CT, CLERMONT, FL, 34711
Community: Heritage Hills
MLS O6344422 • BHHS FLORIDA REALTY, Patti Kincaid
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.
Del Webb Minneola
![2761 TOP HILL CT, MINNEOLA, FL, 34715, Minneola, FL 34715]()
2 beds
|2 baths
|1,943 sq ft
|House
2761 TOP HILL CT, MINNEOLA, FL, 34715
Community: Del Webb Minneola
MLS O6345393 • SERHANT, Silvia Kinkela
Ridgehaven
![181 PARKHAVEN DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,454 sq ft
|House
181 PARKHAVEN DR, ORMOND BEACH, FL, 3217...
Community: Ridgehaven
MLS O6345928 • MERITAGE HOMES OF FL REALTY, Bryan...
Ridgehaven
![179 PARKHAVEN DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,572 sq ft
|House
179 PARKHAVEN DR, ORMOND BEACH, FL, 3217...
Community: Ridgehaven
MLS O6345925 • MERITAGE HOMES OF FL REALTY, Bryan...
Venetian Bay
![3589 GRANDE TUSCANY WAY, NEW SMYRNA BEAC..., New Smyrna Beach, FL 32168]()
6 beds
|10 baths
|8,260 sq ft
|House
3589 GRANDE TUSCANY WAY, NEW SMYRNA BEAC...
Community: Venetian Bay
MLS NS1085990 • COLLADO REAL ESTATE, Scott Yurchi...
The Villages®
![6094 DELPHINA LOOP, THE VILLAGES, FL, 32..., The Villages, FL 32163]()
3 beds
|2 baths
|1,601 sq ft
|House
6094 DELPHINA LOOP, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5102090 • KELLER WILLIAMS CORNERSTONE RE, Ka...
Solivita
![525 SHOREHAVEN DR, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5134633 • BORCHINI REALTY, Dale Pautz
Royal Harbor
![5486 BOUNTY CIR, TAVARES, FL, 32778, Tavares, FL 32778]()
MLS G5102161 • BHHS FLORIDA REALTY, Catherine Lan...
Want to learn more about 55+ communities in Winter Park?
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(888) 625-4885
Vienna Square
![1709 LINZ CT, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884]()
2 beds
|2 baths
|1,164 sq ft
|Villa
1709 LINZ CT, WINTER HAVEN, FL, 33884
Community: Vienna Square
MLS P4936273 • CENTURY 21 WATSON & MYERS REALTY, ...
Twin Lakes
![2585 YELLOW BRICK RD, ST CLOUD, FL, 3477..., St Cloud, FL 34772]()
2 beds
|2 baths
|1,464 sq ft
|Villa
2585 YELLOW BRICK RD, ST CLOUD, FL, 3477...
Community: Twin Lakes
MLS O6343239 • EXP REALTY LLC, Dawn Grigsby
Lakes of Mount Dora
![8923 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757]()
3 beds
|2 baths
|1,926 sq ft
|House
8923 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...
Community: Lakes of Mount Dora
MLS G5102118 • 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.
Plantation Bay Golf & Country Club
![1216 HAMPSTEAD LN, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,973 sq ft
|House
1216 HAMPSTEAD LN, ORMOND BEACH, FL, 321...
Community: Plantation Bay Golf & Country Club
MLS 1217915 • Venture Development Realty, Inc, El...
Highland Fairways
![1836 PRAIRIE DUNES CIR, LAKELAND, FL, 33..., Lakeland, FL 33810]()
2 beds
|2 baths
|1,545 sq ft
|House
1836 PRAIRIE DUNES CIR, LAKELAND, FL, 33...
Community: Highland Fairways
MLS L4955822 • S & D REAL ESTATE SERVICE LLC, Mel...
Royal Harbor
![4954 RAINBOW TROUT RD, TAVARES, FL, 3277..., Tavares, FL 32778]()
3 beds
|2 baths
|1,489 sq ft
|House
4954 RAINBOW TROUT RD, TAVARES, FL, 3277...
Community: Royal Harbor
MLS G5102019 • COLDWELL BANKER VANGUARD EDGE, Chr...
Royal Highlands
![5518 QUEEN VICTORIA DR, LEESBURG, FL, 34..., Leesburg, FL 34748]()
3 beds
|2 baths
|1,757 sq ft
|House
5518 QUEEN VICTORIA DR, LEESBURG, FL, 34...
Community: Royal Highlands
MLS O6343470 • KELLER WILLIAMS ADVANTAGE III, Ern...
The Villages®
![17700 SE 92ND GRANTHAM TER, THE VILLAGES..., The Villages, FL 32162]()
3 beds
|2 baths
|1,516 sq ft
|House
17700 SE 92ND GRANTHAM TER, THE VILLAGES...
Community: The Villages®
MLS OM709472 • RE/MAX FOXFIRE - HWY 40, Hope Desz...
Trilogy® Orlando
![176 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736]()
2 beds
|3 baths
|2,074 sq ft
|House
176 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
MLS O6339822 • WATSON REALTY CORP., REALTORS, Shy...
Royal Highlands
![21737 KING JOHN ST, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,326 sq ft
|House
21737 KING JOHN ST, LEESBURG, FL, 34748
Community: Royal Highlands
MLS G5101951 • FLORIDA PLUS REALTY, LLC, Celie Wh...
Arlington Ridge
![27106 CAMERONS RUN, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|2,436 sq ft
|House
27106 CAMERONS RUN, LEESBURG, FL, 34748
Community: Arlington Ridge
MLS O6343489 • LPT REALTY, LLC, Raymond Reyes
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Lake Ashton
![4429 TURNBERRY LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859]()
3 beds
|2 baths
|1,847 sq ft
|House
4429 TURNBERRY LN, LAKE WALES, FL, 33859
Community: Lake Ashton
MLS P4936246 • COLDWELL BANKER REALTY, Julie Seay
Foxwood Lake Estates
![5026 FOXWOOD BLVD, LAKELAND, FL, 33810, Lakeland, FL 33810]()
2 beds
|2 baths
|1,456 sq ft
|Manufactured Home
5026 FOXWOOD BLVD, LAKELAND, FL, 33810
Community: Foxwood Lake Estates
MLS L4955800 • KELLER WILLIAMS REALTY SMART, Casa...
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.
