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Winter Park, FL 55+ active adult communities & homes for sale
90 communities near Winter Park
2,487 homes near Winter Park
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4 rating (17 reviews)
![The Villages®]()
<$100k
- $1Ms
The Villages®, The Villages, FL
New and Resale
|
55+ age-restricted
|
Built 1978 - present
|
70,000 homes
4.7 rating (18 reviews)
![Solivita]()
$100Ks
- $600Ks
Solivita, Kissimmee, FL
New and Resale
|
55+ age-restricted
|
Built 2000 - present
|
5,900 homes
3.6 rating (48 reviews)
![Latitude Margaritaville]()
$300Ks
- $900Ks
Latitude Margaritaville, Daytona Beach, FL
Resale Only
|
55+ age-restricted
|
Built 2017 - 2025
|
3,900 homes
5 rating (1 reviews)
![Plantation Bay Golf &...]()
$200Ks
- $4Ms
Plantation Bay Golf &..., Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1988 - present
|
3,500 homes
4.5 rating (11 reviews)
![Spruce Creek Country Club]()
$200Ks
- $500Ks
Spruce Creek Country Club, Summerfield, FL
Resale Only
|
55+ age-restricted
|
Built 1996 - 2007
|
3,250 homes
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5 rating (2 reviews)
![Plantation at Leesburg]()
$100Ks
- $500Ks
Plantation at Leesburg, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1987 - 2008
|
2,820 homes
5 rating (3 reviews)
![Stonecrest]()
$200Ks
- $500Ks
Stonecrest, Summerfield, FL
New and Resale
|
55+ age-restricted
|
Built 1990 - present
|
2,200 homes
5 rating (7 reviews)
![Kings Ridge]()
$200Ks
- $400Ks
Kings Ridge, Clermont, FL
Resale Only
|
55+ age-restricted
|
Built 1995 - 2000
|
2,088 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
$300Ks
- $1Ms
Grand Haven, Palm Coast, FL
New and Resale
|
Age-targeted
|
Built 1997 - present
|
1,901 homes
Download the Ultimate 55+ Homebuying Guide
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$100Ks
- $500Ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only
|
Age-targeted
|
Built 1980 - 2006
|
1,806 homes
4.7 rating (3 reviews)
![Spruce Creek South]()
$100Ks
- $300Ks
Spruce Creek South, Summerfield, FL
Resale Only
|
55+ age-restricted
|
Built 1989 - 1995
|
1,650 homes
5 rating (1 reviews)
![Cypress Lakes]()
$100Ks
- $200Ks
Cypress Lakes, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1987 - 2016
|
1,604 homes
5 rating (3 reviews)
![Lake Ashton]()
$200Ks
- $800Ks
Lake Ashton, Lake Wales, FL
Resale Only
|
55+ age-restricted
|
Built 2002 - present
|
1,600 homes
$200Ks
- $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)
![Heritage Isle]()
$200Ks
- $500Ks
Heritage Isle, Viera, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2017
|
1,500 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 (8 reviews)
![Royal Highlands]()
$200Ks
- $500Ks
Royal Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2006
|
1,500 homes
5 rating (1 reviews)
![Del Webb Sunbridge]()
$300Ks
- $1Ms
Del Webb Sunbridge, St. Cloud, FL
New and Resale
|
55+ age-restricted
|
Built 2019 - present
|
1,300 homes
5 rating (1 reviews)
![VillageWalk at Lake Nona]()
$300Ks
- $1Ms
VillageWalk at Lake Nona, Orlando, FL
Resale Only
|
Age-targeted
|
Built 2006 - 2016
|
1,300 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
- $800Ks
Del Webb at Viera, Melbourne, FL
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
1,300 homes
5 rating (8 reviews)
![Pennbrooke Fairways]()
<$100k
- $300Ks
Pennbrooke Fairways, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1980 - 2004
|
1,200 homes
5 rating (1 reviews)
![Sandpiper Golf & Coun...]()
$200Ks
- $400Ks
Sandpiper Golf & Coun..., Lakeland, FL
New and Resale
|
55+ age-restricted
|
Built 1985 - present
|
1,193 homes
3.6 rating (5 reviews)
![Heritage Hills]()
$200Ks
- $500Ks
Heritage Hills, Clermont, FL
New and Resale
|
55+ age-restricted
|
Built 2006 - present
|
1,154 homes
5 rating (1 reviews)
![Cresswind at Victoria Gar...]()
$300Ks
- $600Ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only
|
55+ age-restricted
|
Built 2001 - 2022
|
1,070 homes
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$200Ks
- $700Ks
Halifax Plantation, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1980 - present
|
1,000 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
$400Ks
- $700Ks
Breakaway Trails, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1985 - present
|
976 homes
4 rating (4 reviews)
![Lakes of Mount Dora]()
$400Ks
- $900Ks
Lakes of Mount Dora, Mount Dora, FL
New and Resale
|
55+ age-restricted
|
Built 2006 - present
|
950 homes
4 rating (2 reviews)
![Harbor Hills Country Club]()
$200Ks
- $1Ms
Harbor Hills Country Club, Lady Lake, FL
New and Resale
|
Age-targeted
|
Built 1989 - present
|
940 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.
4.8 rating (6 reviews)
![Highland Lakes]()
$100Ks
- $300Ks
Highland Lakes, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1990 - 1999
|
938 homes
4.4 rating (16 reviews)
![Del Webb Orlando]()
$300Ks
- $400Ks
Del Webb Orlando, Davenport, FL
Resale Only
|
55+ age-restricted
|
Built 2007 - 2021
|
937 homes
5 rating (2 reviews)
![Bridgewater at Viera]()
$300Ks
- $600Ks
Bridgewater at Viera, Melbourne, FL
Resale Only
|
55+ age-restricted
|
Built 2017 - 2023
|
870 homes
$200Ks
- $1Ms
The Country Club of Mount..., Mount Dora, FL
Resale Only
|
Age-targeted
|
Built 1991 - 2005
|
827 homes
4.1 rating (9 reviews)
![Indian River Colony Club]()
$200Ks
- $400Ks
Indian River Colony Club, Melbourne, FL
New and Resale
|
55+ age-restricted
|
Built 1986 - present
|
777 homes
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3.9 rating (7 reviews)
![Summit Greens]()
$300Ks
- $400Ks
Summit Greens, Clermont, FL
Resale Only
|
55+ age-restricted
|
Built 2001 - 2019
|
769 homes
5 rating (1 reviews)
![Royal Harbor]()
$200Ks
- $400Ks
Royal Harbor, Tavares, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2008
|
755 homes
$200Ks
- $500Ks
Lakeside Landings, Oxford, FL
New and Resale
|
Age-targeted
|
Built 2005 - present
|
700 homes
1 rating (1 reviews)
![Sullivan Ranch]()
$300Ks
- $600Ks
Sullivan Ranch, Mount Dora, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2020
|
692 homes
The Villages®
![3377 CLARA CT, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
2 beds
|2 baths
|1,240 sq ft
|Villa
3377 CLARA CT, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5103048 • RE/MAX PREMIER REALTY, Debbie Mart...
Latitude Margaritaville
![784 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,558 sq ft
|House
784 CORAL REEF WAY, DAYTONA BEACH, FL, 3...
Community: Latitude Margaritaville
MLS 1220087 • RE/MAX Signature, Kathleen Craig
Del Webb Sunbridge
![6213 CITRUS GROVE CT, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34771]()
3 beds
|3 baths
|2,269 sq ft
|House
6213 CITRUS GROVE CT, SAINT CLOUD, FL, 3...
Community: Del Webb Sunbridge
MLS O6346549 • PULTE REALTY OF NORTH FLORIDA LLC,...
Sandpiper Golf & Country Club
![6096 KITTIWAKE DR, LAKELAND, FL, 33809, Lakeland, FL 33809]()
3 beds
|2 baths
|1,489 sq ft
|House
6096 KITTIWAKE DR, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS L4956091 • GOLDSMITH PROPERTY SOLUTIONS, Corr...
Kings Ridge
![4122 HAMMERSMITH DR, CLERMONT, FL, 34711, Clermont, FL 34711]()
2 beds
|3 baths
|1,736 sq ft
|House
4122 HAMMERSMITH DR, CLERMONT, FL, 34711
Community: Kings Ridge
MLS G5101564 • KELLER WILLIAMS ELITE PARTNERS III...
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The Villages®
![7821 SE 166TH SMALLWOOD PL, THE VILLAGES..., The Villages, FL 32162]()
3 beds
|2 baths
|1,997 sq ft
|House
7821 SE 166TH SMALLWOOD PL, THE VILLAGES...
Community: The Villages®
MLS O6344948 • BEYCOME OF FLORIDA LLC, Steven Kol...
Plantation Bay Golf & Country Club
![1117 OXBRIDGE LN, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
4 beds
|5 baths
|5,352 sq ft
|House
1117 OXBRIDGE LN, ORMOND BEACH, FL, 3217...
Community: Plantation Bay Golf & Country Club
MLS V4943822 • WATSON REALTY CORP, Theresa Geyer
The Country Club of Mount Dora
![1760 STAFFORD SPRINGS BLVD, MOUNT DORA, ..., Mount Dora, FL 32757]()
2 beds
|2 baths
|1,609 sq ft
|House
1760 STAFFORD SPRINGS BLVD, MOUNT DORA, ...
Community: The Country Club of Mount Dora
MLS O6357581 • WORLD PROPERTIES GROUP, Krasimira ...
Palms at Serenoa
![3435 YELLOWTOP LOOP, CLERMONT, FL, 34714, Clermont, FL 34714]()
3 beds
|2 baths
|1,621 sq ft
|House
3435 YELLOWTOP LOOP, CLERMONT, FL, 34714
Community: Palms at Serenoa
MLS G5102358 • LPT REALTY, LLC, Deborah Govin
The Villages®
![2378 HILL ST, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
2 beds
|2 baths
|1,159 sq ft
|Villa
2378 HILL ST, THE VILLAGES, FL, 32163
Community: The Villages®
MLS TB8429613 • NHR BROKERAGE LLC, Madalina Tat
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 Lakes at Harmony
![3144 SONGBIRD CIR, HARMONY, FL, 34773, Harmony, FL 34773]()
3 beds
|2 baths
|1,852 sq ft
|House
3144 SONGBIRD CIR, HARMONY, FL, 34773
Community: The Lakes at Harmony
MLS O6305997 • ORLANDO PROPERTY ADVISORS, Jessica...
Highland Fairways
![3658 HIGHLAND FAIRWAYS BLVD, LAKELAND, F..., Lakeland, FL 33810]()
3 beds
|2 baths
|1,851 sq ft
|House
3658 HIGHLAND FAIRWAYS BLVD, LAKELAND, F...
Community: Highland Fairways
MLS C7513994 • LOKATION, Ashley Braverman
Twin Lakes
![2337 DATURA LOOP, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772]()
2 beds
|2 baths
|1,351 sq ft
|Villa
2337 DATURA LOOP, SAINT CLOUD, FL, 34772
Community: Twin Lakes
MLS O6265391 • ORLANDO PROPERTY ADVISORS, Jessica...
Twin Lakes
![2335 DATURA LOOP, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772]()
2 beds
|2 baths
|1,351 sq ft
|Villa
2335 DATURA LOOP, SAINT CLOUD, FL, 34772
Community: Twin Lakes
MLS O6265390 • ORLANDO PROPERTY ADVISORS, Jessica...
The Lakes at Harmony
![7520 CASTLEWOOD CT, HARMONY, FL, 34773, Harmony, FL 34773]()
2 beds
|2 baths
|1,455 sq ft
|House
7520 CASTLEWOOD CT, HARMONY, FL, 34773
Community: The Lakes at Harmony
MLS O6267296 • ORLANDO PROPERTY ADVISORS, Jessica...
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Twin Lakes
![2323 DATURA LOOP, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772]()
2 beds
|2 baths
|1,449 sq ft
|Villa
2323 DATURA LOOP, SAINT CLOUD, FL, 34772
Community: Twin Lakes
MLS O6206746 • ORLANDO PROPERTY ADVISORS, Jessica...
The Lakes at Harmony
![3156 SONGBIRD CIR, HARMONY, FL, 34773, Harmony, FL 34773]()
2 beds
|2 baths
|1,423 sq ft
|House
3156 SONGBIRD CIR, HARMONY, FL, 34773
Community: The Lakes at Harmony
MLS O6267298 • ORLANDO PROPERTY ADVISORS, Jessica...
Trilogy® Orlando
![134 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736]()
3 beds
|2 baths
|1,644 sq ft
|House
134 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
MLS G5102534 • KELLER WILLIAMS ELITE PARTNERS III...
Twin Lakes
![5031 DANCY LN, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772]()
MLS O6265389 • ORLANDO PROPERTY ADVISORS, Jessica...
Solivita
![560 GRAND CANAL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5134647 • BORCHINI REALTY, Yamile Osorio Var...
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
![536 PORTOFINO DR, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5137436 • BORCHINI REALTY, Yamile Osorio Var...
Solivita
![542 VITERRA CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5132041 • BORCHINI REALTY, Yamile Osorio Var...
The Villages®
![511 LOMA PASEO DR, THE VILLAGES, FL, 321..., The Villages, FL 32159]()
2 beds
|2 baths
|1,832 sq ft
|House
511 LOMA PASEO DR, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5103623 • RE/MAX PREMIER REALTY LADY LK, Mat...
The Villages®
![1390 VIOLA CT, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
2 beds
|2 baths
|1,156 sq ft
|Villa
1390 VIOLA CT, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5102373 • WILLIAM SMITH, William Smith
Ridgehaven
![457 BROOKHAVEN TRL, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,487 sq ft
|House
457 BROOKHAVEN TRL, ORMOND BEACH, FL, 32...
Community: Ridgehaven
MLS O6323942 • MERITAGE HOMES OF FL REALTY, Tatia...
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Solivita
![350 BALBOA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5113971 • BORCHINI REALTY, Yamile Osorio Var...
The Country Club of Mount Dora
![5061 GREENBRIAR TRL, MOUNT DORA, FL, 327..., Mount Dora, FL 32757]()
4 beds
|3 baths
|2,922 sq ft
|House
5061 GREENBRIAR TRL, MOUNT DORA, FL, 327...
Community: The Country Club of Mount Dora
MLS G5104656 • MOUNT DORA GOLF AND LAKE RLTY, Joh...
Solivita
![699 VILLA PARK RD, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5138108 • BORCHINI REALTY, Yamile Osorio Var...
Lake Henry Estates
![488 SWEETWATER WAY, HAINES CITY, FL, 338..., Haines City, FL 33844]()
2 beds
|2 baths
|1,386 sq ft
|House
488 SWEETWATER WAY, HAINES CITY, FL, 338...
Community: Lake Henry Estates
MLS B4902096 • KLINE REAL ESTATE SERVICES, Scott ...
Four Seasons at Orlando
![1598 WHITEWOOD CT, KISSIMMEE, FL, 34747, Kissimmee, FL 34747]()
3 beds
|2 baths
|2,066 sq ft
|House
1598 WHITEWOOD CT, KISSIMMEE, FL, 34747
Community: Four Seasons at Orlando
MLS S5128295 • LA ROSA REALTY KISSIMMEE, Esmelida...
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®
![752 HARVEY LN, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,985 sq ft
|House
752 HARVEY LN, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5104603 • MAXREV LLC, Jayne Marvin
The Villages®
![3374 CASTLEGATE CT, THE VILLAGES, FL, 32..., The Villages, FL 32163]()
2 beds
|2 baths
|1,156 sq ft
|Villa
3374 CASTLEGATE CT, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5103287 • VISIONARY PROPERTIES INC, Judy Blu...
The Villages®
![1705 STAUNTON ST, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
3 beds
|2 baths
|1,527 sq ft
|House
1705 STAUNTON ST, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5101292 • REALTY EXECUTIVES IN THE VILLAGES,...
The Villages®
![2519 HANLON TER, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,512 sq ft
|House
2519 HANLON TER, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5100639 • COLDWELL BANKER REALTY, William Pe...
Highland Lakes
![5616 LAVER ST, LEESBURG, FL, 34748, Leesburg, FL 34748]()
MLS G5103058 • COLDWELL BANKER REALTY, Sara Suthe...
Want to learn more about 55+ communities in Winter Park?
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(888) 625-4885
The Lakes at Harmony
![3378 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773]()
3 beds
|3 baths
|1,953 sq ft
|House
3378 SAGEBRUSH ST, HARMONY, FL, 34773
Community: The Lakes at Harmony
MLS S5126363 • FIERCE REALTY, Amy Harris
Plantation Bay Golf & Country Club
![18 LANDINGS LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
2 beds
|2 baths
|1,498 sq ft
|Townhouse
18 LANDINGS LN, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS 1213848 • Ormond Realty, Joseph Akialis
The Villages®
![1899 GROESSER PL, THE VILLAGES, FL, 3216..., The Villages, FL 32163]()
2 beds
|2 baths
|1,203 sq ft
|Villa
1899 GROESSER PL, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5104005 • REALTY EXECUTIVES IN THE VILLAGES,...
The Villages®
![2693 PERSIMMON LOOP, THE VILLAGES, FL, 3..., The Villages, FL 32162]()
3 beds
|2 baths
|1,997 sq ft
|House
2693 PERSIMMON LOOP, THE VILLAGES, FL, 3...
Community: The Villages®
MLS G5104036 • REALTY EXECUTIVES IN THE VILLAGES,...
Twin Lakes
![2621 REDBLUSH TER, SAINT CLOUD, FL, 3477..., Saint Cloud, FL 34772]()
3 beds
|3 baths
|1,982 sq ft
|House
2621 REDBLUSH TER, SAINT CLOUD, FL, 3477...
Community: Twin Lakes
MLS S5129334 • SOUTHERN GROUNDS REALTY LLC, Madie...
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2,487
homes
near Winter Park
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REIN updates its listings on a daily basis. Data last updated: Nov 30, 2025.
This application does not include information on all of the properties available for sale at this time.
