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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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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
Want to learn more about 55+ communities in Winter Park?
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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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Questions? Call us:
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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
Solivita
![436 BEL AIR WAY, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5130809 • BELLA VERDE REALTY LLC, Debra DiCi...
Venetian Bay
![2840 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|2,131 sq ft
|Townhouse
2840 ISLES WAY, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
MLS 1209938 • Nexthome Endless Summer, Paige Brew...
The Savannahs
![4464 CALADIUM CIR, WEST MELBOURNE, FL, 3..., West Melbourne, FL 32904]()
4 beds
|2 baths
|2,051 sq ft
|House
4464 CALADIUM CIR, WEST MELBOURNE, FL, 3...
Community: The Savannahs
MLS 1049631 • McWright Realty, Inc., Natalie Laws...
The Villages®
![867 CORTEZ AVE, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
3 beds
|2 baths
|1,770 sq ft
|House
867 CORTEZ AVE, THE VILLAGES, FL, 32159
Community: The Villages®
MLS F10505835 • RE/MAX Select Group, Ron Piccolo
Del Webb Sunbridge
![2948 SCOUT ST, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771]()
5 beds
|5 baths
|3,517 sq ft
|House
2948 SCOUT ST, SAINT CLOUD, FL, 34771
Community: Del Webb Sunbridge
MLS S5131846 • CHARLES RUTENBERG REALTY ORLANDO, ...
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The Villages®
![17238 SE 94TH COULTS CIR, THE VILLAGES, ..., The Villages, FL 32162]()
3 beds
|2 baths
|1,558 sq ft
|House
17238 SE 94TH COULTS CIR, THE VILLAGES, ...
Community: The Villages®
MLS G5095911 • BHHS FLORIDA REALTY, Dawn Bush
Pennbrooke Fairways
![32525 OAK PARK DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|3 baths
|1,643 sq ft
|House
32525 OAK PARK DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS O6199095 • BEYCOME OF FLORIDA LLC, Steven Kol...
Pelican Bay Daytona Beach
![124 KINGBIRD CIR 2040, DAYTONA BEACH, FL..., Daytona Beach, FL 32119]()
2 beds
|2 baths
|1,295 sq ft
|Condo
124 KINGBIRD CIR 2040, DAYTONA BEACH, FL...
Community: Pelican Bay Daytona Beach
MLS FC311510 • REALTY PROS ASSURED, Marvin Adams
Kings Ridge
![2096 BRAXTON ST, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS G5100085 • OLYMPUS EXECUTIVE REALTY INC, Lisa...
Pelican Bay Daytona Beach
![244 PALM SPARROW CT, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119]()
2 beds
|2 baths
|1,370 sq ft
|House
244 PALM SPARROW CT, DAYTONA BEACH, FL, ...
Community: Pelican Bay Daytona Beach
MLS 1117527 • Seemore Realty Group Inc., Judy Tin...
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.
Latitude Margaritaville
![703 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124]()
2 beds
|3 baths
|2,161 sq ft
|House
703 CORAL REEF WAY, DAYTONA BEACH, FL, 3...
Community: Latitude Margaritaville
MLS 1213519 • LoKation, Aimee Aballo
The Villages®
![5810 PENNEY LN, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|2,016 sq ft
|House
5810 PENNEY LN, THE VILLAGES, FL, 32163
Community: The Villages®
MLS O6268450 • EQUITYPRO LLC, Gregory Aime
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...
Arlington Ridge
![4546 SHENANDOAH RIVER TRL, LEESBURG, FL,..., Leesburg, FL 34748]()
3 beds
|2 baths
|1,948 sq ft
|House
4546 SHENANDOAH RIVER TRL, LEESBURG, FL,...
Community: Arlington Ridge
MLS A11838523 • LoKation, Alexandra Soterakis
Traditions at Lake Ruby
![3023 CANEEL ST, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884]()
2 beds
|2 baths
|1,385 sq ft
|Townhouse
3023 CANEEL ST, WINTER HAVEN, FL, 33884
Community: Traditions at Lake Ruby
MLS P4935116 • CENTURY 21 WOLF'S CROSSING REALTY,...
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Traditions at Lake Ruby
![2825 ATTWATER LOOP, WINTER HAVEN, FL, 33..., Winter Haven, FL 33884]()
2 beds
|2 baths
|1,385 sq ft
|Villa
2825 ATTWATER LOOP, WINTER HAVEN, FL, 33...
Community: Traditions at Lake Ruby
MLS O6260348 • MILLENIUM REALTY GROUP, Norxis Bar...
Breakaway Trails
![4 CREEK BLUFF WAY, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|2,575 sq ft
|House
4 CREEK BLUFF WAY, ORMOND BEACH, FL, 321...
Community: Breakaway Trails
MLS 1210332 • Realty Pros Assured, Terri Wilkinso...
Spruce Creek Country Club
![8447 SE 137TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|2 baths
|2,387 sq ft
|House
8447 SE 137TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek Country Club
MLS OM671272 • RE/MAX PREMIER REALTY LADY LK, Jay...
Solivita
![3432 FALLBROOK DR, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5130489 • BORCHINI REALTY, Cherie Pontes
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...
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.
Plantation Bay Golf & Country Club
![414 LONG COVE CT, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|2,129 sq ft
|House
414 LONG COVE CT, ORMOND BEACH, FL, 3217...
Community: Plantation Bay Golf & Country Club
MLS TB8395053 • EMPIRE NETWORK REALTY, Jon Kanner
Pennbrooke Fairways
![751 OLD OAKS LN, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,753 sq ft
|House
751 OLD OAKS LN, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS G5097637 • CHARLES RUTENBERG REALTY ORLANDO, ...
Venetian Bay
![594 MARISOL DR, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|2,409 sq ft
|House
594 MARISOL DR, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
MLS 1211078 • FAME Real Estate LLC, Mike Khorassa...
The Lakes at Harmony
![3333 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773]()
3 beds
|2 baths
|1,677 sq ft
|House
3333 SAGEBRUSH ST, HARMONY, FL, 34773
Community: The Lakes at Harmony
MLS S5127761 • HOMETRUST REALTY GROUP, Lulis Bati...
The Villages®
![1202 DEL TORO DR, THE VILLAGES, FL, 3215..., The Villages, FL 32159]()
2 beds
|2 baths
|1,558 sq ft
|House
1202 DEL TORO DR, THE VILLAGES, FL, 3215...
Community: The Villages®
MLS G5104572 • WORTH CLARK REALTY, Muhammad Mufti
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The Villages®
![3459 OLDHAM LN, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|1,446 sq ft
|Villa
3459 OLDHAM LN, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5103133 • REALTY EXECUTIVES IN THE VILLAGES,...
New
Venetian Bay
![384 LEONI ST, NEW SMYRNA BEACH, FL, 3216..., New Smyrna Beach, FL 32168]()
3 beds
|2 baths
|2,083 sq ft
|House
384 LEONI ST, NEW SMYRNA BEACH, FL, 3216...
Community: Venetian Bay
MLS 1220386 • RE/MAX Signature, Shannon FitzPatri...
Spruce Creek South
![17505 SE 100TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,359 sq ft
|Villa
17505 SE 100TH CT, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
MLS OM700442 • BERKSHIRE HATHAWAY HS FLORIDA, Kim...
Traditions at Lake Ruby
![2769 ATTWATER LOOP, WINTER HAVEN, FL, 33..., Winter Haven, FL 33884]()
2 beds
|2 baths
|1,385 sq ft
|Villa
2769 ATTWATER LOOP, WINTER HAVEN, FL, 33...
Community: Traditions at Lake Ruby
MLS S5124391 • JASON MITCHELL REAL ESTATE FLO, Da...
New
Del Webb Oasis
![15162 CANOPY COVE DR, WINTER GARDEN, FL,..., Winter Garden, FL 34787]()
2 beds
|2 baths
|2,049 sq ft
|House
15162 CANOPY COVE DR, WINTER GARDEN, FL,...
Community: Del Webb Oasis
MLS S5139203 • LA ROSA REALTY LLC, Angela Camacho
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®
![3031 HICKS PL, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
4 beds
|3 baths
|2,248 sq ft
|House
3031 HICKS PL, THE VILLAGES, FL, 32163
Community: The Villages®
MLS OM708688 • LPT REALTY, LLC, Anthony Filone
New
Halifax Plantation
![2885 MONAGHAN DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,115 sq ft
|House
2885 MONAGHAN DR, ORMOND BEACH, FL, 3217...
Community: Halifax Plantation
MLS NS1086717 • PREMIER SOTHEBYS INTL REALTY, Jen...
New
Heritage Isle
![2842 GALINDO CIR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|2 baths
|2,227 sq ft
|House
2842 GALINDO CIR, MELBOURNE, FL, 32940
Community: Heritage Isle
MLS 1063055 • RE/MAX Elite, Deborah L Tomczak
New
Arlington Ridge
![4714 INDEPENDENCE TRL, LEESBURG, FL, 347..., Leesburg, FL 34748]()
3 beds
|2 baths
|1,753 sq ft
|House
4714 INDEPENDENCE TRL, LEESBURG, FL, 347...
Community: Arlington Ridge
MLS OM714183 • DISCOVER FLORIDA REALTY GROUP LLC,...
Twin Lakes
![2672 MEADOWEDGE LOOP, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772]()
3 beds
|3 baths
|2,935 sq ft
|House
2672 MEADOWEDGE LOOP, SAINT CLOUD, FL, 3...
Community: Twin Lakes
MLS O6295013 • DREAM FINDERS REALTY GROUP CORP, A...
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(888) 625-4885
The Villages®
![1169 CALGARY ST, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
2 beds
|2 baths
|1,220 sq ft
|House
1169 CALGARY ST, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5102834 • LPT REALTY, LLC, Lizzy Bell
Summer Trees
![109 UNDERBRUSH TRL, PORT ORANGE, FL, 321..., Port Orange, FL 32128]()
2 beds
|2 baths
|1,403 sq ft
|House
109 UNDERBRUSH TRL, PORT ORANGE, FL, 321...
Community: Summer Trees
MLS 1219517 • Heritage Realty Associates, Lori Cl...
The Villages®
![733 PALMA DR, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
3 beds
|2 baths
|1,936 sq ft
|House
733 PALMA DR, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5103384 • WORTH CLARK REALTY, Greg Szablewsk...
Heritage Isle
![6378 VAN NESS DR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|2 baths
|1,861 sq ft
|House
6378 VAN NESS DR, MELBOURNE, FL, 32940
Community: Heritage Isle
MLS 1060416 • aReal Estate Service Team, Maggie S...
The Villages®
![916 MEDIRA DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|1,255 sq ft
|House
916 MEDIRA DR, LADY LAKE, FL, 32159
Community: The Villages®
MLS G5099880 • DOWN HOME REALTY, LLLP, Brandon Sh...
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2,487
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near Winter Park
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