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Winter Park, FL 55+ active adult communities & homes for sale - Page 63
90 communities near Winter Park
2,553 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
$300ks
- $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale
|
Age-targeted
|
Built 2004 - present
|
1,561 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
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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
5 rating (3 reviews)
![Stonecrest]()
$200ks
- $500ks
Stonecrest, Summerfield, FL
New and Resale
|
55+ age-restricted
|
Built 1990 - present
|
2,200 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
4.7 rating (3 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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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
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
$300ks
- $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1980 - present
|
1,000 homes
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$200ks
- $800ks
Grand Haven, Palm Coast, FL
New and Resale
|
Age-targeted
|
Built 1997 - present
|
1,901 homes
$100ks
- $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only
|
Age-targeted
|
Built 1980 - 2006
|
1,806 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 (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
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
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 (2 reviews)
![Heritage Isle]()
$300ks
- $500ks
Heritage Isle, Viera, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2017
|
1,500 homes
4 rating (4 reviews)
![Lakes of Mount Dora]()
$300ks
- $900ks
Lakes of Mount Dora, Mount Dora, FL
New and Resale
|
55+ age-restricted
|
Built 2006 - present
|
950 homes
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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
5 rating (8 reviews)
![Pennbrooke Fairways]()
<$100k
- $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1980 - 2004
|
1,200 homes
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
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
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
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
1 rating (1 reviews)
![Sullivan Ranch]()
$200ks
- $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2020
|
692 homes
5 rating (1 reviews)
![Royal Harbor]()
$200ks
- $800ks
Royal Harbor, Tavares, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2008
|
755 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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4.8 rating (6 reviews)
![Highland Lakes]()
$100ks
- $200ks
Highland Lakes, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1990 - 1999
|
938 homes
$100ks
- $200ks
Colonnades, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1985 - 1994
|
360 homes
$200ks
- $1Ms
The Country Club of Mount..., Mount Dora, FL
Resale Only
|
Age-targeted
|
Built 1991 - 2005
|
827 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
- $200ks
Scottish Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1983 - 1992
|
653 homes
$100ks
- $200ks
Foxwood Lake Estates, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1982 - 1987
|
545 homes
3.8 rating (5 reviews)
![Traditions at Lake Ruby]()
$200ks
- $300ks
Traditions at Lake Ruby, Winter Haven, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2020
|
552 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
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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
Pennbrooke Fairways
![33409 PENNBROOKE PKWY, LEESBURG, FL, 347..., Leesburg, FL 34748]()
3 beds
|2 baths
|2,111 sq ft
|House
33409 PENNBROOKE PKWY, LEESBURG, FL, 347...
Community: Pennbrooke Fairways
MLS G5092982 • MAXREV LLC, Jayne Marvin
The Villages®
![1613 CHERRY HILL RD, THE VILLAGES, FL, 3..., The Villages, FL 32159]()
2 beds
|2 baths
|1,357 sq ft
|House
1613 CHERRY HILL RD, THE VILLAGES, FL, 3...
Community: The Villages®
MLS G5092223 • FLORIDA FINE HOMES REALTY, LLC, Ca...
The Villages®
![901 CHULA CT, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,248 sq ft
|House
901 CHULA CT, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5092725 • FLORIDA FINE HOMES REALTY, LLC, Ca...
Summer Trees
![109 CROOKED PINE RD, PORT ORANGE, FL, 32..., Port Orange, FL 32128]()
2 beds
|2 baths
|1,106 sq ft
|House
109 CROOKED PINE RD, PORT ORANGE, FL, 32...
Community: Summer Trees
MLS 1209437 • Heritage Realty Associates, Lori Cl...
Plantation Bay Golf & Country Club
![820 ALDENHAM LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
2 beds
|2 baths
|1,510 sq ft
|Townhouse
820 ALDENHAM LN, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS FC307092 • ADAMS, CAMERON & CO., REALTORS, Ki...
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Highland Fairways
![1957 PRAIRIE DUNES CIR, LAKELAND, FL, 33..., Lakeland, FL 33810]()
2 beds
|2 baths
|1,637 sq ft
|House
1957 PRAIRIE DUNES CIR, LAKELAND, FL, 33...
Community: Highland Fairways
MLS L4950660 • REMAX EXPERTS, Lorrie Clark
Plantation Bay Golf & Country Club
![51 BAY POINTE DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,996 sq ft
|House
51 BAY POINTE DR, ORMOND BEACH, FL, 3217...
Community: Plantation Bay Golf & Country Club
MLS 1209215 • Realty Evolution Inc, Marsha Thayer
Lakes of Mount Dora
![8456 NORWICH WAY, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
4 beds
|3 baths
|2,460 sq ft
|House
8456 NORWICH WAY, MOUNT DORA, FL, 32757
Community: Lakes of Mount Dora
MLS O6278226 • KELLER WILLIAMS LEGACY, Thomas Hix...
Solivita
![917 SHOREHAVEN DR, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS G5092308 • FLORIDA PLUS REALTY, LLC, Christin...
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.
Pelican Bay Daytona Beach
![105 WOOD DUCK CIR C, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119]()
2 beds
|2 baths
|1,242 sq ft
|Condo
105 WOOD DUCK CIR C, DAYTONA BEACH, FL, ...
Community: Pelican Bay Daytona Beach
MLS NS1083767 • COLDWELL BANKER COAST REALTY, Max...
Carlsberg Estates on Lake Suzanne
![524 LAKE SUZANNE DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859]()
3 beds
|3 baths
|1,718 sq ft
|House
524 LAKE SUZANNE DR, LAKE WALES, FL, 338...
Community: Carlsberg Estates on Lake Suzanne
MLS P4933513 • CENTURY 21 MYERS REALTY LAKE WALES...
Summer Trees
![89 CROOKED PINE RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128]()
2 beds
|2 baths
|1,010 sq ft
|House
89 CROOKED PINE RD, PORT ORANGE, FL, 321...
Community: Summer Trees
MLS O6275671 • HERITAGE REALTY ASSOCIATES, Susan ...
Kings Ridge
![3667 KINGSWOOD CT, CLERMONT, FL, 34711, Clermont, FL 34711]()
2 beds
|2 baths
|1,552 sq ft
|House
3667 KINGSWOOD CT, CLERMONT, FL, 34711
Community: Kings Ridge
MLS O6275507 • FLORIDA PRESTIGIOUS HOMES INC, Ian...
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Del Webb Orlando
![336 DEL SOL AVE, DAVENPORT, FL, 33837, Davenport, FL 33837]()
3 beds
|3 baths
|2,086 sq ft
|House
336 DEL SOL AVE, DAVENPORT, FL, 33837
Community: Del Webb Orlando
MLS S5118919 • RIDGE REALTY GROUP LLC, Stephen Ne...
Heritage - The Cottages of Sanders Grove
![6342 SANDERS GROVE CIR, OKAHUMPKA, FL, 3..., Okahumpka, FL 34762]()
3 beds
|2 baths
|1,788 sq ft
|House
6342 SANDERS GROVE CIR, OKAHUMPKA, FL, 3...
Community: Heritage - The Cottages of Sanders Grove
MLS G5091903 • ERA GRIZZARD REAL ESTATE, Craig Yo...
Halifax Plantation
![3169 CONNEMARA DR, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,919 sq ft
|House
3169 CONNEMARA DR, ORMOND BEACH, FL, 321...
Community: Halifax Plantation
MLS V4940513 • CENTURY 21 SUNDANCE REALTY, Nicole...
Royal Highlands
![5004 SAINT ANDREWS ARC, LEESBURG, FL, 34..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,483 sq ft
|House
5004 SAINT ANDREWS ARC, LEESBURG, FL, 34...
Community: Royal Highlands
MLS G5090900 • FLORIDA PLUS REALTY, LLC, Tonya Ti...
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.
Pennbrooke Fairways
![32712 TIMBERWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,909 sq ft
|House
32712 TIMBERWOOD DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS O6273298 • VELEZ COURTESY MANAGEMENT, Gerry K...
Spruce Creek Country Club
![12592 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491]()
3 beds
|2 baths
|2,413 sq ft
|House
12592 SE 97TH TERRACE RD, SUMMERFIELD, F...
Community: Spruce Creek Country Club
MLS G5091462 • PREMIER SOTHEBYS INT'L REALTY, Kei...
Four Seasons at Orlando
![1987 KEY BAY TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747]()
2 beds
|2 baths
|1,437 sq ft
|Villa
1987 KEY BAY TRL, KISSIMMEE, FL, 34747
Community: Four Seasons at Orlando
MLS O6270026 • KELLER WILLIAMS ADVANTAGE III, Nat...
Plantation Bay Golf & Country Club
![1221 HARWICK LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|2 baths
|2,151 sq ft
|House
1221 HARWICK LN, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS FC306494 • ADAMS, CAMERON & CO., REALTORS, Ry...
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Solivita
![2448 PALM TREE DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5117943 • PELLEGO, LLC, Paul Maiatico
Venetian Bay
![3069 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168]()
2 beds
|2 baths
|1,003 sq ft
|Townhouse
3069 ISLES WAY, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
MLS NS1083506 • EXIT REAL ESTATE PROPERTY SOL, Ca...
The Villages®
![2530 SAFFRON LN, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,512 sq ft
|House
2530 SAFFRON LN, THE VILLAGES, FL, 32162
Community: The Villages®
MLS O6269489 • BEST HOMES, LLC., Harry D'Onofrio
Arlington Ridge
![27103 CAMERONS RUN, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|2,236 sq ft
|House
27103 CAMERONS RUN, LEESBURG, FL, 34748
Community: Arlington Ridge
MLS G5090718 • RE/MAX SELECT PARTNERS, Tracy Camp...
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.
Venetian Bay
![3088 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168]()
2 beds
|2 baths
|1,003 sq ft
|Townhouse
3088 ISLES WAY, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
MLS NS1083432 • EXIT REAL ESTATE PROPERTY SOL, Ca...
The Villages®
![1881 SASSPARILLA WAY, THE VILLAGES, FL, ..., The Villages, FL 32162]()
3 beds
|2 baths
|1,965 sq ft
|House
1881 SASSPARILLA WAY, THE VILLAGES, FL, ...
Community: The Villages®
MLS G5090910 • RE/MAX PREMIER REALTY LADY LK, Oli...
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...
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...
Pelican Bay Daytona Beach
![149 BLACK DUCK CIR, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32119]()
2 beds
|2 baths
|1,075 sq ft
|House
149 BLACK DUCK CIR, DAYTONA BEACH, FL, 3...
Community: Pelican Bay Daytona Beach
MLS 1207265 • RE/MAX Signature, Jeffery Hurt
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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...
Twin Lakes
![5031 DANCY LN, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772]()
MLS O6265389 • ORLANDO PROPERTY ADVISORS, Jessica...
Spruce Creek South
![17925 SE 100TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,248 sq ft
|House
17925 SE 100TH TER, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
MLS G5090750 • RE/MAX PREMIER REALTY LADY LK, Ger...
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.
Heritage - The Cottages of Sanders Grove
![28023 CYPRESS SPRINGS LOOP, OKAHUMPKA, F..., Okahumpka, FL 34762]()
3 beds
|2 baths
|1,601 sq ft
|House
28023 CYPRESS SPRINGS LOOP, OKAHUMPKA, F...
Community: Heritage - The Cottages of Sanders Grove
MLS O6265290 • ALL REAL ESTATE & INVESTMENTS, Pat...
The Villages®
![9199 SE 171ST COOPER LOOP, THE VILLAGES,..., The Villages, FL 32162]()
3 beds
|2 baths
|1,850 sq ft
|House
9199 SE 171ST COOPER LOOP, THE VILLAGES,...
Community: The Villages®
MLS G5090513 • KELLER WILLIAMS CORNERSTONE RE, Ka...
Solivita
![1423 HARBOR RIDGE DR, POINCIANA, FL, 347..., Poinciana, FL 34759]()
2 beds
|2 baths
|1,703 sq ft
|House
1423 HARBOR RIDGE DR, POINCIANA, FL, 347...
Community: Solivita
MLS TB8329416 • NHR BROKERAGE LLC, Madalina Tat
Harbor Hills Country Club
![39320 HARBOR HILLS BLVD, LADY LAKE, FL, ..., Lady Lake, FL 32159]()
3 beds
|2 baths
|2,120 sq ft
|House
39320 HARBOR HILLS BLVD, LADY LAKE, FL, ...
Community: Harbor Hills Country Club
MLS G5090374 • MORRIS REALTY AND INVESTMENTS, Kim...
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Twin Lakes
![2482 YELLOW BRICK RD, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772]()
2 beds
|2 baths
|1,346 sq ft
|Villa
2482 YELLOW BRICK RD, SAINT CLOUD, FL, 3...
Community: Twin Lakes
MLS S5116882 • WEICHERT REALTORS HALLMARK PRO, Sh...
Legacy of Leesburg
![5107 AURORA DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,658 sq ft
|House
5107 AURORA DR, LEESBURG, FL, 34748
Community: Legacy of Leesburg
MLS G5090078 • VANGIE BERRY SIGNATURE REALTY, Ang...
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2,553
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REIN updates its listings on a daily basis. Data last updated: Feb 24, 2026.
This application does not include information on all of the properties available for sale at this time.
