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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
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.
$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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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 (2 reviews)
![Heritage Isle]()
$200Ks
- $500Ks
Heritage Isle, Viera, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2017
|
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
$300Ks
- $800Ks
Del Webb at Viera, Melbourne, FL
New Construction
|
55+ age-restricted
|
Built 2021 - 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.
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 (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
Want to learn more about 55+ communities in Winter Park?
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Questions? Call us:
(888) 625-4885
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
- $600Ks
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
Harbor Hills Country Club
![39911 BAYVIEW DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
3 beds
|2 baths
|2,120 sq ft
|House
39911 BAYVIEW DR, LADY LAKE, FL, 32159
Community: Harbor Hills Country Club
MLS OM710713 • LPT REALTY, LLC, Gary Martin
Summer Trees
![1305 SHADOW PATH DR, PORT ORANGE, FL, 32..., Port Orange, FL 32128]()
3 beds
|2 baths
|1,821 sq ft
|House
1305 SHADOW PATH DR, PORT ORANGE, FL, 32...
Community: Summer Trees
MLS 1219736 • Realty Pros Assured, Mark Card
Del Webb at Viera
![8447 WALO DR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|3 baths
|2,570 sq ft
|House
8447 WALO DR, MELBOURNE, FL, 32940
Community: Del Webb at Viera
MLS 1061523 • Viera Builders Realty, Inc., C Scot...
Del Webb at Viera
![8497 WALO DR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
4 beds
|5 baths
|3,469 sq ft
|House
8497 WALO DR, MELBOURNE, FL, 32940
Community: Del Webb at Viera
MLS 1061480 • Viera Builders Realty, Inc., C Scot...
Spruce Creek South
![15901 SE 101ST CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
5 beds
|2 baths
|1,708 sq ft
|House
15901 SE 101ST CIR, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
MLS OM713016 • DR HORTON REALTY OF WEST CENTRAL F...
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The Villages®
![9671 SE 168TH MAPLESONG LN, THE VILLAGES..., The Villages, FL 32162]()
3 beds
|2 baths
|1,527 sq ft
|House
9671 SE 168TH MAPLESONG LN, THE VILLAGES...
Community: The Villages®
MLS G5103842 • LPT REALTY, LLC, Douglas Troyer
The Villages®
![8932 SE 168TH SEDGWICK PL, THE VILLAGES,..., The Villages, FL 32162]()
3 beds
|2 baths
|1,483 sq ft
|Villa
8932 SE 168TH SEDGWICK PL, THE VILLAGES,...
Community: The Villages®
MLS G5096744 • WORTH CLARK REALTY, Chris Day
The Villages®
![2866 JUDAH ST, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
2 beds
|2 baths
|1,257 sq ft
|House
2866 JUDAH ST, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5093055 • BHHS FLORIDA REALTY, DeLite Bowden
Royal Harbor
![5502 BOUNTY CIR, TAVARES, FL, 32778, Tavares, FL 32778]()
MLS G5091652 • ARELLANO REALTY & INVESTMENTS, Kat...
Traditions at Lake Ruby
![3365 RALEIGH DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884]()
2 beds
|2 baths
|1,295 sq ft
|House
3365 RALEIGH DR, WINTER HAVEN, FL, 33884
Community: Traditions at Lake Ruby
MLS P4936886 • EXP REALTY LLC, James Barris
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
![113 VENICE LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS O6356845 • MARK SPAIN REAL ESTATE, Jeffery Jo...
The Villages®
![2051 PALO ALTO AVE, THE VILLAGES, FL, 32..., The Villages, FL 32159]()
3 beds
|2 baths
|1,908 sq ft
|House
2051 PALO ALTO AVE, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5090005 • WORTH CLARK REALTY, Steve Vena
Trilogy® Orlando
![537 NARROW VIEW LN, GROVELAND, FL, 34736, Groveland, FL 34736]()
3 beds
|2 baths
|1,905 sq ft
|House
537 NARROW VIEW LN, GROVELAND, FL, 34736
Community: Trilogy® Orlando
MLS O6351909 • FLORIDA PLUS REALTY, LLC, Diana St...
Solivita
![543 VIA VITALE CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5137772 • BORCHINI REALTY, Edie Stauffer
Plantation at Leesburg
![24914 CRANES ROOST CIR, LEESBURG, FL, 34..., Leesburg, FL 34748]()
3 beds
|2 baths
|1,801 sq ft
|House
24914 CRANES ROOST CIR, LEESBURG, FL, 34...
Community: Plantation at Leesburg
MLS G5104174 • FLORIDA PLUS REALTY, LLC, Sandy Tw...
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The Villages®
![1738 AUGUSTINE DR, THE VILLAGES, FL, 321..., The Villages, FL 32159]()
4 beds
|3 baths
|2,959 sq ft
|House
1738 AUGUSTINE DR, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5094331 • SALLY LOVE REAL ESTATE INC, Caroli...
Palms at Serenoa
![17418 BLAZING STAR CIR, CLERMONT, FL, 34..., Clermont, FL 34714]()
3 beds
|2 baths
|1,621 sq ft
|House
17418 BLAZING STAR CIR, CLERMONT, FL, 34...
Community: Palms at Serenoa
MLS G5104050 • DENIZ REALTY PARTNERS LLC, Tommy M...
Stonecrest
![17306 SE 112TH COURT RD, SUMMERFIELD, FL..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,955 sq ft
|House
17306 SE 112TH COURT RD, SUMMERFIELD, FL...
Community: Stonecrest
MLS G5102892 • CHARLES RUTENBERG REALTY ORLANDO, ...
Trilogy® Orlando
![109 FALLING ACORN AVE, GROVELAND, FL, 34..., Groveland, FL 34736]()
3 beds
|2 baths
|1,780 sq ft
|House
109 FALLING ACORN AVE, GROVELAND, FL, 34...
Community: Trilogy® Orlando
MLS G5103725 • COLDWELL BANKER HUBBARD HANSEN, Pa...
Latitude Margaritaville
![856 MARGARITAVILLE AVE, DAYTONA BEACH, F..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,862 sq ft
|House
856 MARGARITAVILLE AVE, DAYTONA BEACH, F...
Community: Latitude Margaritaville
MLS 1219623 • 386RealEstate.com, Kevin Kling
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.
Indian River Colony Club
![1453 PATRIOT DR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
4 beds
|2 baths
|2,293 sq ft
|House
1453 PATRIOT DR, MELBOURNE, FL, 32940
Community: Indian River Colony Club
MLS 1024799 • Four Star Real Estate LLC, Shellie ...
Solivita
![525 GENOA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5131724 • FAIRWAY REALTY OF SOLIVITA, Bonnie...
Pelican Bay Daytona Beach
![114 BLUE HERON DR D, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119]()
2 beds
|2 baths
|1,242 sq ft
|Condo
114 BLUE HERON DR D, DAYTONA BEACH, FL, ...
Community: Pelican Bay Daytona Beach
MLS 1219702 • RE/MAX Signature, Julia Lomonosov
The Villages®
![2120 WILLOW GROVE WAY, THE VILLAGES, FL,..., The Villages, FL 32162]()
3 beds
|2 baths
|1,927 sq ft
|House
2120 WILLOW GROVE WAY, THE VILLAGES, FL,...
Community: The Villages®
MLS G5096711 • IM REALTY, Ira Miller
Summer Trees
![129 DUSK MEADOW TRL, PORT ORANGE, FL, 32..., Port Orange, FL 32128]()
2 beds
|2 baths
|1,414 sq ft
|House
129 DUSK MEADOW TRL, PORT ORANGE, FL, 32...
Community: Summer Trees
MLS 1218939 • RE/MAX Signature, Norina Burt
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Archers Mill
![3321 ARCH AVE, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
4 beds
|4 baths
|2,787 sq ft
|House
3321 ARCH AVE, ORMOND BEACH, FL, 32174
Community: Archers Mill
MLS O6353240 • DR HORTON REALTY OF CENTRAL FLORID...
Archers Mill
![3349 ARCH AVE, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
5 beds
|5 baths
|3,345 sq ft
|House
3349 ARCH AVE, ORMOND BEACH, FL, 32174
Community: Archers Mill
MLS 1216646 • D R Horton Realty of Central Florid...
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...
Arlington Ridge
![3507 ARLINGTON RIDGE BLVD, LEESBURG, FL,..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,476 sq ft
|House
3507 ARLINGTON RIDGE BLVD, LEESBURG, FL,...
Community: Arlington Ridge
MLS G5099008 • WATSON REALTY CORP, Nancy McCloske...
Twin Lakes
![2632 MEADOWEDGE LP LP, ST. CLOUD, FL, 34..., St. Cloud, FL 34772]()
3 beds
|3 baths
|2,335 sq ft
|House
2632 MEADOWEDGE LP LP, ST. CLOUD, FL, 34...
Community: Twin Lakes
MLS 1061376 • Metropolis R.E. Solutions LLC, Adam...
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
![307 MONTEREY ST, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5137888 • BORCHINI REALTY, Cherie Pontes
Solivita
![461 TREVISO DR, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5137945 • BORCHINI REALTY, Yamile Osorio Var...
Heritage Landings
![2667 CANYON CREST DR, LAKELAND, FL, 3381..., Lakeland, FL 33811]()
3 beds
|2 baths
|1,710 sq ft
|House
2667 CANYON CREST DR, LAKELAND, FL, 3381...
Community: Heritage Landings
MLS L4957054 • S & D REAL ESTATE SERVICE LLC, Jim...
Lakes at Laurel Highlands
![2667 CANYON CREST DR, LAKELAND, FL, 3381..., Lakeland, FL 33811]()
3 beds
|2 baths
|1,710 sq ft
|House
2667 CANYON CREST DR, LAKELAND, FL, 3381...
Community: Lakes at Laurel Highlands
MLS L4957054 • S & D REAL ESTATE SERVICE LLC, Jim...
Plantation Bay Golf & Country Club
![402 LONG COVE RD, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|2,658 sq ft
|House
402 LONG COVE RD, ORMOND BEACH, FL, 3217...
Community: Plantation Bay Golf & Country Club
MLS 1212894 • LPT Realty, LLC, Karla Fonseca
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The Villages®
![3331 OVERLAND TER, THE VILLAGES, FL, 321..., The Villages, FL 32163]()
2 beds
|2 baths
|1,161 sq ft
|Villa
3331 OVERLAND TER, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5098098 • WORTH CLARK REALTY, Steve Vena
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...
Stonecrest
![12135 SE 172ND LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|2,031 sq ft
|House
12135 SE 172ND LN, SUMMERFIELD, FL, 3449...
Community: Stonecrest
MLS G5101748 • RE/MAX FOXFIRE - LADY LAKE, Cheryl...
Solivita
![128 RIALTO RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5132072 • PELLEGO, LLC, Paul Maiatico
Plantation at Leesburg
![4826 SABLE RIDGE CT, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,882 sq ft
|House
4826 SABLE RIDGE CT, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5098317 • FLORIDA PLUS REALTY, LLC, Celie Wh...
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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.
