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Winter Park, FL 55+ active adult communities & homes for sale - Page 47
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.
Breakaway Trails
![15 CIRCLE CREEK WAY, ORMOND BEACH, FL, 3..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,875 sq ft
|House
15 CIRCLE CREEK WAY, ORMOND BEACH, FL, 3...
Community: Breakaway Trails
MLS V4946676 • REALTY PROS ASSURED, Didiayer Snyd...
Lakes of Mount Dora
![2154 WALLINGFORD LOOP, MOUNT DORA, FL, 3..., Mount Dora, FL 32757]()
2 beds
|2 baths
|1,958 sq ft
|House
2154 WALLINGFORD LOOP, MOUNT DORA, FL, 3...
Community: Lakes of Mount Dora
MLS O6372764 • DIAMOND REAL ESTATE GROUP, George ...
Grand Haven
![455 RIVERFRONT DR A302, PALM COAST, FL, ..., Palm Coast, FL 32137]()
3 beds
|2 baths
|1,779 sq ft
|Condo
455 RIVERFRONT DR A302, PALM COAST, FL, ...
Community: Grand Haven
MLS 2124530 • CENTURY 21 INTEGRA, PATRICIA MARGAR...
Solivita
![729 GLENDORA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5141045 • BORCHINI REALTY, Heather Hayes
Halifax Plantation
![3324 WESTMEATH DR, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,724 sq ft
|House
3324 WESTMEATH DR, ORMOND BEACH, FL, 321...
Community: Halifax Plantation
MLS FC315116 • GRAND LIVING REALTY, Perry Gambrel...
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Solivita
![405 BALBOA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5141125 • LPT REALTY, LLC, Leticia Morales
Lakes of Mount Dora
![3963 KENNEBUNK LOOP, MOUNT DORA, FL, 327..., Mount Dora, FL 32757]()
3 beds
|2 baths
|1,732 sq ft
|House
3963 KENNEBUNK LOOP, MOUNT DORA, FL, 327...
Community: Lakes of Mount Dora
MLS O6372583 • DR HORTON REALTY OF CENTRAL FLORID...
The Villages®
![1433 ARBOR TRL, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,490 sq ft
|House
1433 ARBOR TRL, THE VILLAGES, FL, 32162
Community: The Villages®
MLS OM715023 • SHOWCASE PROPERTIES OF CENTRAL, Ti...
Traditions at Lake Ruby
![2733 ATTWATER LOOP, WINTER HAVEN, FL, 33..., Winter Haven, FL 33884]()
3 beds
|3 baths
|2,032 sq ft
|House
2733 ATTWATER LOOP, WINTER HAVEN, FL, 33...
Community: Traditions at Lake Ruby
MLS P4937444 • CENTURY 21 MYERS REALTY LAKE WALES...
Stonecrest
![11193 SE 173RD PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,974 sq ft
|House
11193 SE 173RD PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
MLS OM716182 • KELLER WILLIAMS CORNERSTONE RE, Ci...
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.
Sullivan Ranch
![20946 SULLIVAN RANCH BLVD, MOUNT DORA, F..., Mount Dora, FL 32757]()
6 beds
|4 baths
|3,499 sq ft
|House
20946 SULLIVAN RANCH BLVD, MOUNT DORA, F...
Community: Sullivan Ranch
MLS G5106228 • LPT REALTY, LLC, Nick Poulsen
Heritage Isle
![6977 FLORISTANA DR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|2 baths
|2,127 sq ft
|House
6977 FLORISTANA DR, MELBOURNE, FL, 32940
Community: Heritage Isle
MLS O6372367 • YHSGR-PIONEER, XENIA Geelhoed
Trilogy® Orlando
![383 ALCOVE DR, GROVELAND, FL, 34736, Groveland, FL 34736]()
2 beds
|2 baths
|1,568 sq ft
|Villa
383 ALCOVE DR, GROVELAND, FL, 34736
Community: Trilogy® Orlando
MLS G5106373 • CENTURY 21 MYERS ROSE REALTY, Gret...
Grand Haven
![455 RIVERFRONT DR UNIT A201, PALM COAST,..., Palm Coast, FL 32137]()
3 beds
|3 baths
|2,167 sq ft
|Condo
455 RIVERFRONT DR UNIT A201, PALM COAST,...
Community: Grand Haven
MLS FC315019 • COASTAL GATEWAY REAL ESTATE GR, Er...
Arlington Ridge
![27143 ROANOKE DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,699 sq ft
|House
27143 ROANOKE DR, LEESBURG, FL, 34748
Community: Arlington Ridge
MLS G5106223 • COOPER HOMEFRONT REALTY, Joe Coope...
The Villages®
![4515 BIGGS PL, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|3 baths
|2,837 sq ft
|House
4515 BIGGS PL, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5106121 • LPT REALTY, LLC, Kerry Hanson
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Plantation Bay Golf & Country Club
![844 PINEWOOD DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
2 beds
|2 baths
|1,526 sq ft
|House
844 PINEWOOD DR, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS O6369906 • REDFIN CORPORATION, Tammy Shaver
Lake Henry Estates
![656 SWEETWATER WAY, HAINES CITY, FL, 338..., Haines City, FL 33844]()
2 beds
|2 baths
|1,681 sq ft
|House
656 SWEETWATER WAY, HAINES CITY, FL, 338...
Community: Lake Henry Estates
MLS P4937438 • FLORIDA HOME CHOICE REALTY, Janell...
Spruce Creek Country Club
![9479 SE 130TH STREET RD, SUMMERFIELD, FL..., Summerfield, FL 34491]()
3 beds
|3 baths
|2,346 sq ft
|House
9479 SE 130TH STREET RD, SUMMERFIELD, FL...
Community: Spruce Creek Country Club
MLS G5106280 • RE/MAX PREMIER REALTY LADY LK, Rob...
Spruce Creek Country Club
![9345 SE 136TH PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
2 beds
|2 baths
|1,989 sq ft
|House
9345 SE 136TH PL, SUMMERFIELD, FL, 34491
Community: Spruce Creek Country Club
MLS G5106276 • RE/MAX PREMIER REALTY LADY LK, Rob...
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.
Solivita
![2316 PALM TREE DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5141190 • ARISTA REALTY GROUP, LLC, Douglas ...
Spruce Creek Country Club
![13185 SE 93RD TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,244 sq ft
|House
13185 SE 93RD TERRACE RD, SUMMERFIELD, F...
Community: Spruce Creek Country Club
MLS OM715956 • RE/MAX PREMIER REALTY LADY LK, Jay...
Lake Ashton
![4189 LIMERICK DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859]()
2 beds
|2 baths
|2,227 sq ft
|House
4189 LIMERICK DR, LAKE WALES, FL, 33859
Community: Lake Ashton
MLS P4937366 • A+ REALTY LLC, Emily Muscarella
Lake Ashton
![4081 DUNMORE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859]()
3 beds
|2 baths
|2,027 sq ft
|House
4081 DUNMORE DR, LAKE WALES, FL, 33859
Community: Lake Ashton
MLS S5141060 • MAZELG REALTY, Mary Sorrell
The Villages®
![3079 NUTWOOD AVE, THE VILLAGES, FL, 3216..., The Villages, FL 32163]()
2 beds
|2 baths
|1,156 sq ft
|Villa
3079 NUTWOOD AVE, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS V4946528 • EXP REALTY LLC, Debby Sommer
Highland Lakes
![26707 CASH CT, LEESBURG, FL, 34748, Leesburg, FL 34748]()
MLS G5106116 • ERA GRIZZARD REAL ESTATE, Ricky Ha...
Spruce Creek Country Club
![13820 SE 86TH TER, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,248 sq ft
|House
13820 SE 86TH TER, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS OM715480 • SELLSTATE NGR- SUMMERFIELD, Virgil...
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(888) 625-4885
Stonecrest
![17787 SE 114TH AVE, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,867 sq ft
|House
17787 SE 114TH AVE, SUMMERFIELD, FL, 344...
Community: Stonecrest
MLS G5105855 • RE/MAX PREMIER REALTY LADY LK, Cin...
Arlington Ridge
![26822 BULL RUN, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,602 sq ft
|House
26822 BULL RUN, LEESBURG, FL, 34748
Community: Arlington Ridge
MLS G5105994 • EXIT REALTY TRI-COUNTY, Jaret Whit...
The Villages®
![5885 FLINT LOOP, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|3 baths
|1,977 sq ft
|House
5885 FLINT LOOP, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5106008 • RE/MAX PREMIER REALTY, Tammy Freil...
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 Sunbridge
![2575 PINE PRESERVE CT, ST CLOUD, FL, 347..., St Cloud, FL 34771]()
3 beds
|3 baths
|2,483 sq ft
|House
2575 PINE PRESERVE CT, ST CLOUD, FL, 347...
Community: Del Webb Sunbridge
MLS O6370525 • REAL BROKER, LLC, Peter Frano
The Villages®
![5107 NE 122ND BLVD, OXFORD, FL, 34484, Oxford, FL 34484]()
4 beds
|3 baths
|1,910 sq ft
|House
5107 NE 122ND BLVD, OXFORD, FL, 34484
Community: The Villages®
MLS O6370099 • COLDWELL BANKER REALTY, James Gips...
Lake Ashton
![4577 BACK NINE DR, WINTER HAVEN, FL, 338..., Winter Haven, FL 33884]()
3 beds
|2 baths
|1,918 sq ft
|House
4577 BACK NINE DR, WINTER HAVEN, FL, 338...
Community: Lake Ashton
MLS P4937386 • LAKE ASHTON REALTY INC., Lori Raat...
Summer Trees
![49 CYPRESS POND RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128]()
2 beds
|2 baths
|1,048 sq ft
|House
49 CYPRESS POND RD, PORT ORANGE, FL, 321...
Community: Summer Trees
MLS 2123962 • PLANTANA REALTY, INC., SANDRA FISHE...
The Timbers at Everlands
![1273 BLESSED ISLES DR, PALM BAY, FL, 329..., Palm Bay, FL 32907]()
3 beds
|3 baths
|2,601 sq ft
|House
1273 BLESSED ISLES DR, PALM BAY, FL, 329...
Community: The Timbers at Everlands
MLS 1065749 • Blue Marlin Real Estate, Jason Bist...
Solivita
![251 ROCK SPRINGS DR, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759]()
2 beds
|2 baths
|2,050 sq ft
|House
251 ROCK SPRINGS DR, KISSIMMEE, FL, 3475...
Community: Solivita
MLS A11938835 • New Beginnings R.E. & Investm, Th...
Plantation at Leesburg
![25300 HIBISCUS ST, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,908 sq ft
|House
25300 HIBISCUS ST, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS TB8460495 • HOMECOIN.COM, Jonathan Minerick
Solivita
![699 GLENDORA RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS TB8452905 • FLORIDA EXECUTIVE REALTY, Jason L...
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55places can help!
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Latitude Margaritaville
![562 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,160 sq ft
|Villa
562 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...
Community: Latitude Margaritaville
MLS TB8460216 • APOGEE REALTY SERVICES, Mary Boor
The Villages®
![8089 SE 174TH BELHAVEN LOOP, THE VILLAGE..., The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
8089 SE 174TH BELHAVEN LOOP, THE VILLAGE...
Community: The Villages®
MLS O6370078 • CORCORAN PREMIER REALTY, Crystal G...
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.
