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Winter Park, FL 55+ active adult communities & homes for sale - Page 52
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
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Questions? Call us:
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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.
Del Webb Orlando
![540 PAMPLONA PL, DAVENPORT, FL, 33837, Davenport, FL 33837]()
2 beds
|3 baths
|1,772 sq ft
|House
540 PAMPLONA PL, DAVENPORT, FL, 33837
Community: Del Webb Orlando
MLS O6358701 • KELLER WILLIAMS WINTER PARK, David...
Plantation Bay Golf & Country Club
![823 CREEKWOOD DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,762 sq ft
|House
823 CREEKWOOD DR, ORMOND BEACH, FL, 3217...
Community: Plantation Bay Golf & Country Club
MLS FC313872 • VENTURE DEVELOPMENT REALTY,INC, De...
Grand Haven
![2 GLENEAGLES PL, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
3 beds
|2 baths
|1,785 sq ft
|House
2 GLENEAGLES PL, PALM COAST, FL, 32137
Community: Grand Haven
MLS FC314103 • RE/MAX SELECT PROFESSIONALS, Cryst...
The Villages®
![2865 JUDAH ST, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
2 beds
|2 baths
|1,286 sq ft
|Villa
2865 JUDAH ST, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5104341 • KELLER WILLIAMS CORNERSTONE RE, Ka...
The Villages®
![1067 CARVER CT, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
2 beds
|2 baths
|1,270 sq ft
|Villa
1067 CARVER CT, THE VILLAGES, FL, 32163
Community: The Villages®
MLS TB8448232 • WWW.HOMEZU.COM, Jason Saphire
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The Villages®
![442 PACE LN, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,100 sq ft
|House
442 PACE LN, THE VILLAGES, FL, 32162
Community: The Villages®
MLS OM713510 • REALTY ONE GROUP DAVALLS, David St...
Highland Lakes
![26209 NEWCOMBE CIR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,514 sq ft
|House
26209 NEWCOMBE CIR, LEESBURG, FL, 34748
Community: Highland Lakes
MLS G5104476 • COLDWELL BANKER VANGUARD EDGE, Bil...
The Villages®
![3108 CARROLLTON CT, THE VILLAGES, FL, 32..., The Villages, FL 32162]()
3 beds
|2 baths
|1,704 sq ft
|Villa
3108 CARROLLTON CT, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5103727 • BROKER ASSOCIATES REALTY, Christie...
Royal Highlands
![21122 LIONHEART DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,453 sq ft
|House
21122 LIONHEART DR, LEESBURG, FL, 34748
Community: Royal Highlands
MLS G5104218 • FLORIDA PLUS REALTY, LLC, Tonya Ti...
Lake Ashton
![4040 BIRKDALE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859]()
2 beds
|2 baths
|1,530 sq ft
|House
4040 BIRKDALE DR, LAKE WALES, FL, 33859
Community: Lake Ashton
MLS P4937011 • LAKE ASHTON REALTY INC., Lori Raat...
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®
![8143 SE 175TH COLUMBIA PL, THE VILLAGES,..., The Villages, FL 32162]()
3 beds
|2 baths
|1,231 sq ft
|House
8143 SE 175TH COLUMBIA PL, THE VILLAGES,...
Community: The Villages®
MLS OM713357 • KELLER WILLIAMS CORNERSTONE RE, Cr...
The Villages®
![2109 HARSTON TRL, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
2 beds
|2 baths
|1,142 sq ft
|House
2109 HARSTON TRL, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5104448 • WORTH CLARK REALTY, Steve Vena
Spruce Creek Country Club
![13235 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491]()
2 beds
|2 baths
|2,149 sq ft
|House
13235 SE 97TH TERRACE RD, SUMMERFIELD, F...
Community: Spruce Creek Country Club
MLS OM713351 • RE/MAX FOXFIRE - SUMMERFIELD, Ed D...
Ridgehaven
![1340 OAKHAVEN AVE, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,190 sq ft
|House
1340 OAKHAVEN AVE, ORMOND BEACH, FL, 321...
Community: Ridgehaven
MLS 1219879 • Meritage Homes of Florida Realty LL...
Colonnades
![4908 DAWNVIEW LN, LAKELAND, FL, 33811, Lakeland, FL 33811]()
MLS P4936997 • J&T PROPERTY SOLUTIONS GROUP LLC, ...
Venetian Bay
![3507 CASALTA CIR, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|2,644 sq ft
|House
3507 CASALTA CIR, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS 1219853 • Oceans Luxury Realty Full Service L...
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The Villages®
![2282 SHEEHAN ST, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
2 beds
|2 baths
|1,227 sq ft
|Villa
2282 SHEEHAN ST, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5104320 • ATLAS CENTRAL FLORIDA REALTY, Mich...
Royal Highlands
![21202 BRAVEHEART DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,588 sq ft
|House
21202 BRAVEHEART DR, LEESBURG, FL, 34748
Community: Royal Highlands
MLS G5104368 • VANGIE BERRY SIGNATURE REALTY, Ang...
Ridgehaven
![437 BROOKHAVEN TRL, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174]()
3 beds
|3 baths
|2,181 sq ft
|House
437 BROOKHAVEN TRL, ORMOND BEACH, FL, 32...
Community: Ridgehaven
MLS O6359263 • MERITAGE HOMES OF FL REALTY, Bryan...
Huntington at Hunter's Ridge
![13 FAWN HAVEN TRL, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,156 sq ft
|House
13 FAWN HAVEN TRL, ORMOND BEACH, FL, 321...
Community: Huntington at Hunter's Ridge
MLS 1219831 • Coldwell Banker Premier Properties,...
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.
Lake Ashton
![4249 BERWICK DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859]()
3 beds
|2 baths
|1,847 sq ft
|House
4249 BERWICK DR, LAKE WALES, FL, 33859
Community: Lake Ashton
MLS L4957196 • ROOST REALTY GROUP LLC, Barb Wiech...
Grand Haven
![14 EGRET DR, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
MLS FC313955 • CHAD AND SANDY REAL ESTATE GRP, Ch...
Venetian Bay
![3566 MARIBELLA DR, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168]()
5 beds
|3 baths
|2,405 sq ft
|House
3566 MARIBELLA DR, NEW SMYRNA BEACH, FL,...
Community: Venetian Bay
MLS 2117248 • HOMECOIN.COM, JONATHAN MINERICK
Tohoqua Reserve
![1991 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744]()
3 beds
|2 baths
|2,056 sq ft
|House
1991 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
MLS TB8445148 • MIHARA & ASSOCIATES INC., Raymond...
Venetian Bay
![552 CARO CT, NEW SMYRNA BEACH, FL, 32168, New Smyrna Beach, FL 32168]()
3 beds
|2 baths
|1,728 sq ft
|House
552 CARO CT, NEW SMYRNA BEACH, FL, 32168
Community: Venetian Bay
MLS NS1086506 • WATSON REALTY CORP, Margie Palmer
Pelican Bay Daytona Beach
![102 BOB WHITE CT 102C, DAYTONA BEACH, FL..., Daytona Beach, FL 32119]()
2 beds
|2 baths
|1,165 sq ft
|Condo
102 BOB WHITE CT 102C, DAYTONA BEACH, FL...
Community: Pelican Bay Daytona Beach
MLS V4945814 • RE/MAX SIGNATURE, Stephanie Cathey
Pelican Bay Daytona Beach
![102 BOB WHITE CT C, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32119]()
2 beds
|2 baths
|1,165 sq ft
|Condo
102 BOB WHITE CT C, DAYTONA BEACH, FL, 3...
Community: Pelican Bay Daytona Beach
MLS 1219796 • RE/MAX Signature, Nicole Schlaffer
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Heritage Hills
![3542 FAIRWATERS CT D, CLERMONT, FL, 3471..., Clermont, FL 34711]()
2 beds
|2 baths
|1,374 sq ft
|Villa
3542 FAIRWATERS CT D, CLERMONT, FL, 3471...
Community: Heritage Hills
MLS O6359127 • MARK SPAIN REAL ESTATE, Jeff Jones
The Villages®
![511 CHULA VISTA AVE, THE VILLAGES, FL, 3..., The Villages, FL 32159]()
3 beds
|2 baths
|1,562 sq ft
|House
511 CHULA VISTA AVE, THE VILLAGES, FL, 3...
Community: The Villages®
MLS G5104226 • WORTH CLARK REALTY, Joy Farenden
Pelican Bay Daytona Beach
![257 GULL DR, DAYTONA BEACH, FL, 32119, Daytona Beach, FL 32119]()
2 beds
|2 baths
|1,900 sq ft
|House
257 GULL DR, DAYTONA BEACH, FL, 32119
Community: Pelican Bay Daytona Beach
MLS V4945791 • ADAMS, CAMERON & CO., REALTORS, Do...
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
![1155 GLENDORA RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS FC313946 • COASTAL GATEWAY REAL ESTATE GR, Cy...
Esplanade at Highland Ranch
![1038 TIMBERVALE TRL, CLERMONT, FL, 34715, Clermont, FL 34715]()
3 beds
|3 baths
|2,287 sq ft
|House
1038 TIMBERVALE TRL, CLERMONT, FL, 34715
Community: Esplanade at Highland Ranch
MLS G5104056 • OPTIMA ONE REALTY, INC., Heather W...
The Villages®
![903 RAMOS DR, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
3 beds
|2 baths
|1,836 sq ft
|House
903 RAMOS DR, THE VILLAGES, FL, 32159
Community: The Villages®
MLS O6358859 • REALTY HUB, Gordon Veling
Four Seasons at Orlando
![2116 LIMESTONE TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747]()
3 beds
|3 baths
|2,360 sq ft
|House
2116 LIMESTONE TRL, KISSIMMEE, FL, 34747
Community: Four Seasons at Orlando
MLS O6358742 • VIVA ORLANDO REALTY INC., Susan Ri...
Spring Lake Towers
![700 MIRROR TER 505, WINTER HAVEN, FL, 33..., Winter Haven, FL 33881]()
2 beds
|2 baths
|1,190 sq ft
|Condo
700 MIRROR TER 505, WINTER HAVEN, FL, 33...
Community: Spring Lake Towers
MLS TB8445379 • CHARLES RUTENBERG REALTY INC, Vic...
The Villages®
![7168 SE 173RD ARLINGTON LOOP, THE VILLAG..., The Villages, FL 32162]()
3 beds
|2 baths
|1,512 sq ft
|House
7168 SE 173RD ARLINGTON LOOP, THE VILLAG...
Community: The Villages®
MLS G5103916 • SALLY LOVE REAL ESTATE, Caroline F...
The Villages®
![4346 HELENA TER, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
2 beds
|2 baths
|1,295 sq ft
|House
4346 HELENA TER, THE VILLAGES, FL, 32163
Community: The Villages®
MLS O6358106 • THE AGENCY FL, Cassidy McWherter
Lakes of Mount Dora
![8065 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757]()
4 beds
|3 baths
|3,551 sq ft
|House
8065 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...
Community: Lakes of Mount Dora
MLS G5103865 • WATSON REALTY CORP, Jonathan Faw
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The Villages®
![5094 NE 122ND BLVD, OXFORD, FL, 34484, Oxford, FL 34484]()
4 beds
|4 baths
|2,109 sq ft
|House
5094 NE 122ND BLVD, OXFORD, FL, 34484
Community: The Villages®
MLS OM712430 • MEADOWS REALTY, LLC, Bert Meadows
The Villages®
![1865 CLAVERTON ST, THE VILLAGES, FL, 321..., The Villages, FL 32162]()
3 beds
|2 baths
|2,579 sq ft
|House
1865 CLAVERTON ST, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5104096 • RE/MAX PREMIER REALTY LADY LK, Bud...
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.
