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Winter Park, FL 55+ active adult communities & homes for sale - Page 49
90 communities near Winter Park
2,513 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 (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 (3 reviews)
![Lake Ashton]()
$200ks
- $500ks
Lake Ashton, Lake Wales, FL
Resale Only
|
55+ age-restricted
|
Built 2002 - present
|
1,600 homes
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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
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 (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
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$200ks
- $800ks
Grand Haven, Palm Coast, FL
New and Resale
|
Age-targeted
|
Built 1997 - present
|
1,901 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
$300ks
- $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1980 - present
|
1,000 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)
![Sandpiper Golf & Coun...]()
$100ks
- $300ks
Sandpiper Golf & Coun..., Lakeland, FL
New and Resale
|
55+ age-restricted
|
Built 1985 - present
|
1,193 homes
2.8 rating (6 reviews)
![Arlington Ridge]()
$200ks
- $500ks
Arlington Ridge, Leesburg, FL
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
629 homes
$100ks
- $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only
|
Age-targeted
|
Built 1980 - 2006
|
1,806 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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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
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 (2 reviews)
![Heritage Isle]()
$300ks
- $500ks
Heritage Isle, Viera, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2017
|
1,500 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 (8 reviews)
![Pennbrooke Fairways]()
<$100k
- $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1980 - 2004
|
1,200 homes
4.8 rating (6 reviews)
![Highland Lakes]()
$100ks
- $200ks
Highland Lakes, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1990 - 1999
|
938 homes
5 rating (1 reviews)
![Royal Harbor]()
$200ks
- $800ks
Royal Harbor, Tavares, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2008
|
755 homes
$300ks
- $600ks
Four Seasons at Orlando, Kissimmee, FL
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
557 homes
5 rating (1 reviews)
![Cresswind at Victoria Gar...]()
$200ks
- $600ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only
|
55+ age-restricted
|
Built 2001 - 2022
|
1,070 homes
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$100ks
- $200ks
Scottish Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1983 - 1992
|
653 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
$300ks
- $600ks
Tohoqua Reserve, Kissimmee, FL
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
258 homes
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
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.
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
$200ks
- $400ks
The Lakes at Harmony, Harmony, FL
New and Resale
|
55+ age-restricted
|
Built 2016 - present
|
400 homes
$200ks
- $400ks
Summer Trees, Port Orange, FL
Resale Only
|
55+ age-restricted
|
Built 1976 - 2005
|
500 homes
$400ks
- $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1985 - present
|
976 homes
Want to learn more about 55+ communities in Winter Park?
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Questions? Call us:
(888) 625-4885
$100ks
- $200ks
Foxwood Lake Estates, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1982 - 1987
|
545 homes
Pelican Bay Daytona Beach
![102 BOB WHITE CT # 102C, DAYTONA BEACH, ..., Daytona Beach, FL 32119]()
2 beds
|2 baths
|1,165 sq ft
|Condo
102 BOB WHITE CT # 102C, DAYTONA BEACH, ...
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
Del Webb Sunbridge
![2973 CHERRY BLOSSOM LOOP, ST CLOUD, FL, ..., St Cloud, FL 34771]()
2 beds
|2 baths
|1,584 sq ft
|Villa
2973 CHERRY BLOSSOM LOOP, ST CLOUD, FL, ...
Community: Del Webb Sunbridge
MLS S5138111 • ORLANDO REGIONAL REALTY, Heike Kna...
Plantation at Leesburg
![25533 BELLE HELENE, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,352 sq ft
|Manufactured Home
25533 BELLE HELENE, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5104285 • CENTURY 21 MYERS ROSE REALTY, Eliz...
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
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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...
Latitude Margaritaville
![631 LOST SHAKER WAY, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,464 sq ft
|House
631 LOST SHAKER WAY, DAYTONA BEACH, FL, ...
Community: Latitude Margaritaville
MLS 1219771 • Bob Hodges and Sons Realty, Susan W...
Grand Haven
![19 FRONT ST, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
MLS FC313909 • COASTAL GATEWAY REAL ESTATE GR, An...
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 GROUP,...
Plantation Bay Golf & Country Club
![1109 HANSBERRY CT, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
2 beds
|3 baths
|1,604 sq ft
|Townhouse
1109 HANSBERRY CT, ORMOND BEACH, FL, 321...
Community: Plantation Bay Golf & Country Club
MLS 1219767 • The Barnett Group Inc., Sally LaCla...
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...
Ridgehaven
![1320 OAKHAVEN AVE, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
4 beds
|2 baths
|1,908 sq ft
|House
1320 OAKHAVEN AVE, ORMOND BEACH, FL, 321...
Community: Ridgehaven
MLS O6358278 • MERITAGE HOMES OF FL REALTY, Bryan...
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Plantation at Leesburg
![5414 ASTOR ST, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,256 sq ft
|House
5414 ASTOR ST, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5104214 • CHARLES RUTENBERG REALTY ORLANDO, ...
Plantation at Leesburg
![25125 BELLEVUE, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|936 sq ft
|Manufactured Home
25125 BELLEVUE, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5104233 • CENTURY 21 MYERS ROSE REALTY, Sher...
Solivita
![100 MERIDIAN AVE, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5137130 • PELLEGO, LLC, Stan Wilson
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
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®
![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,...
Sandpiper Golf & Country Club
![6189 MAGPIE DR, LAKELAND, FL, 33809, Lakeland, FL 33809]()
3 beds
|2 baths
|2,009 sq ft
|House
6189 MAGPIE DR, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS L4957153 • LAKELAND HOMES AND REALTY, LLC, Me...
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...
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The Villages®
![714 DEL ROSARIO ST, THE VILLAGES, FL, 32..., The Villages, FL 32159]()
3 beds
|2 baths
|1,908 sq ft
|House
714 DEL ROSARIO ST, THE VILLAGES, FL, 32...
Community: The Villages®
MLS O6358712 • IRON VALLEY REAL ESTATE CENTRAL FL...
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...
Plantation at Leesburg
![24725 BRIGHTWATER CT, LEESBURG, FL, 3474..., Leesburg, FL 34748]()
3 beds
|3 baths
|2,132 sq ft
|House
24725 BRIGHTWATER CT, LEESBURG, FL, 3474...
Community: Plantation at Leesburg
MLS TB8445644 • HOME SOLD REALTY LLC, Camilo Pere...
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
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.
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
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
Lake Henry Estates
![488 SWEETWATER WAY, HAINES CITY, FL, 338..., Haines City, FL 33844]()
2 beds
|2 baths
|1,626 sq ft
|House
488 SWEETWATER WAY, HAINES CITY, FL, 338...
Community: Lake Henry Estates
MLS B4902096 • KLINE REAL ESTATE SERVICES, Scott ...
Solivita
![307 MONTEREY ST, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5137888 • BORCHINI REALTY, Cherie Pontes
Foxwood Lake Estates
![5027 FOREST CREST DR, LAKELAND, FL, 3381..., Lakeland, FL 33810]()
2 beds
|2 baths
|1,248 sq ft
|Manufactured Home
5027 FOREST CREST DR, LAKELAND, FL, 3381...
Community: Foxwood Lake Estates
MLS L4957092 • KELLER WILLIAMS REALTY SMART, Dani...
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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...
The Villages®
![944 HORTON TER, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|1,647 sq ft
|Villa
944 HORTON TER, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5104062 • RE/MAX PREMIER REALTY, Matthew Rob...
Spruce Creek Country Club
![13520 SE 87TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,554 sq ft
|House
13520 SE 87TH CIR, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS G5104088 • ARROW REALTY & INVESTMENTS INC, Re...
Solivita
![461 TREVISO DR, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5137945 • 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.
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...
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, Jul...
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, Jul...
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
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Spruce Creek Country Club
![13914 SE 96TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,958 sq ft
|House
13914 SE 96TH CIR, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS OM712777 • JUDY L. TROUT REALTY, Jennifer Tra...
Latitude Margaritaville
![472 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,464 sq ft
|House
472 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...
Community: Latitude Margaritaville
MLS 1219613 • Bob Hodges and Sons Realty, Kelley ...
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2,513
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REIN updates its listings on a daily basis. Data last updated: Apr 10, 2026.
This application does not include information on all of the properties available for sale at this time.
