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Winter Park, FL 55+ active adult communities & homes for sale - Page 45
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
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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
Solivita
![591 HIGHLANDS HAMMOCK DR, KISSIMMEE, FL,..., Kissimmee, FL 34759]()
2 beds
|2 baths
|2,078 sq ft
|House
591 HIGHLANDS HAMMOCK DR, KISSIMMEE, FL,...
Community: Solivita
MLS S5139546 • BORCHINI REALTY, Heather Hayes
Plantation at Leesburg
![3425 MOUNT HOPE LOOP, LEESBURG, FL, 3474..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,888 sq ft
|House
3425 MOUNT HOPE LOOP, LEESBURG, FL, 3474...
Community: Plantation at Leesburg
MLS G5105235 • CENTURY 21 CARIOTI, Bonnie Valenti...
Solivita
![1192 VIA GALUPPI ST, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759]()
3 beds
|2 baths
|1,723 sq ft
|House
1192 VIA GALUPPI ST, KISSIMMEE, FL, 3475...
Community: Solivita
MLS G5105188 • EXP REALTY LLC, Edalys Ramos
The Villages®
![1651 DURAN DR, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,121 sq ft
|House
1651 DURAN DR, THE VILLAGES, FL, 32162
Community: The Villages®
MLS O6363935 • FLORIDA REALTY INVESTMENTS, Landon...
Bridgewater at Viera
![9763 ALISTER DR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
2 beds
|2 baths
|1,565 sq ft
|House
9763 ALISTER DR, MELBOURNE, FL, 32940
Community: Bridgewater at Viera
MLS 1063716 • Ellingson Properties, Gregory Ellin...
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Spruce Creek Country Club
![8789 SE 136TH LN, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
3 beds
|2 baths
|2,029 sq ft
|House
8789 SE 136TH LN, SUMMERFIELD, FL, 34491
Community: Spruce Creek Country Club
MLS G5105202 • RE/MAX PREMIER REALTY LADY LK, Rob...
Solivita
![601 GRAND CANAL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5139145 • BORCHINI REALTY, Heather Hayes
VillageWalk at Lake Nona
![7991 ESTA LN, ORLANDO, FL, 32827, Orlando, FL 32827]()
4 beds
|5 baths
|3,454 sq ft
|House
7991 ESTA LN, ORLANDO, FL, 32827
Community: VillageWalk at Lake Nona
MLS O6365393 • ENGEL & VOLKERS NEW SMYRNA, Chris ...
Scottish Highlands
![2105 GREENLAW CT # 2105, LEESBURG, FL, 3..., Leesburg, FL 34788]()
2 beds
|2 baths
|932 sq ft
|Condo
2105 GREENLAW CT # 2105, LEESBURG, FL, 3...
Community: Scottish Highlands
MLS S5139750 • RIVA REALTY GROUP LLC, Vildan Nigr...
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®
![2136 KERWOOD LOOP, THE VILLAGES, FL, 321..., The Villages, FL 32162]()
2 beds
|2 baths
|1,135 sq ft
|House
2136 KERWOOD LOOP, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5104968 • KELLER WILLIAMS CORNERSTONE RE, Ka...
Harbor Hills Country Club
![5090 GREENS DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
4 beds
|3 baths
|2,532 sq ft
|House
5090 GREENS DR, LADY LAKE, FL, 32159
Community: Harbor Hills Country Club
MLS G5104887 • REALTY EXECUTIVES IN THE VILLAGES,...
Del Webb at Viera
![8870 SHORELINE AVE, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|3 baths
|2,171 sq ft
|House
8870 SHORELINE AVE, MELBOURNE, FL, 32940
Community: Del Webb at Viera
MLS 1063616 • Engel&Voelkers Melb Beachside, Marc...
Solivita
![193 TORINO LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS O6365110 • SENIOR TRANSITIONS REALTY, LLC, Ki...
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Cresswind at Victoria Gardens
![322 BELLINGRATH TER, DELAND, FL, 32724, Deland, FL 32724]()
3 beds
|3 baths
|2,708 sq ft
|House
322 BELLINGRATH TER, DELAND, FL, 32724
Community: Cresswind at Victoria Gardens
MLS O6364136 • BETTER HOMES AND GARDENS REAL ESTA...
Arlington Ridge
![4719 HERITAGE TRL, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,761 sq ft
|House
4719 HERITAGE TRL, LEESBURG, FL, 34748
Community: Arlington Ridge
MLS OM714339 • DISCOVER FLORIDA REALTY GROUP LLC,...
The Villages®
![16905 SE 81ST ELLERSLIE CT, THE VILLAGES..., The Villages, FL 32162]()
2 beds
|2 baths
|1,160 sq ft
|Villa
16905 SE 81ST ELLERSLIE CT, THE VILLAGES...
Community: The Villages®
MLS G5105196 • SALLY LOVE REAL ESTATE, Kim Coffer
The Villages®
![2598 HIALEAH AVE, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
1 beds
|1 baths
|1,120 sq ft
|Villa
2598 HIALEAH AVE, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS OM714573 • RE/MAX PREMIER REALTY LADY LK, Don...
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.
Cresswind DeLand
![1213 CRESSWIND BLVD, DELAND, FL, 32724, Deland, FL 32724]()
3 beds
|3 baths
|1,983 sq ft
|House
1213 CRESSWIND BLVD, DELAND, FL, 32724
Community: Cresswind DeLand
MLS W7880799 • MALTBIE REALTY GROUP, Bill Maltbie
Cresswind DeLand
![1235 CRESSWIND BLVD, DELAND, FL, 32724, Deland, FL 32724]()
3 beds
|4 baths
|2,496 sq ft
|House
1235 CRESSWIND BLVD, DELAND, FL, 32724
Community: Cresswind DeLand
MLS W7880800 • MALTBIE REALTY GROUP, Bill Maltbie
Stonecrest
![17808 SE 115 CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
3 beds
|3 baths
|2,282 sq ft
|House
17808 SE 115 CT, SUMMERFIELD, FL, 34491
Community: Stonecrest
MLS OM714475 • BASSETT PREMIER REALTY INC, Sharon...
Solivita
![806 EBB TIDE LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5139382 • PELLEGO, LLC, Paul Maiatico
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The Villages®
![2595 ASCOT LOOP, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,156 sq ft
|Villa
2595 ASCOT LOOP, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5105147 • REAL BROKER, LLC, Katy Kelly
Plantation at Leesburg
![25245 QUAIL CROFT PL, LEESBURG, FL, 3474..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,653 sq ft
|House
25245 QUAIL CROFT PL, LEESBURG, FL, 3474...
Community: Plantation at Leesburg
MLS G5105096 • CENTURY 21 MYERS ROSE REALTY, Sher...
The Villages®
![972 GREG TER, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
2 beds
|2 baths
|1,266 sq ft
|Villa
972 GREG TER, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5105158 • GILBO REALTY LLC, Mark Gilbo
Foxwood Lake Estates
![4969 FOXWOOD LAKE DR, LAKELAND, FL, 3381..., Lakeland, FL 33810]()
2 beds
|2 baths
|1,456 sq ft
|Manufactured Home
4969 FOXWOOD LAKE DR, LAKELAND, FL, 3381...
Community: Foxwood Lake Estates
MLS P4937150 • KELLER WILLIAMS REALTY SMART 1, Ma...
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 Isle
![3352 RUSS PL, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
MLS 1063433 • Florida East Coast Real Estate, Lyn...
Spruce Creek South
![17747 SE 97TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|2,026 sq ft
|House
17747 SE 97TH AVE, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
MLS OM714384 • CHARLES RUTENBERG REALTY INC, Lind...
Heritage Hills
![3553 BELLAND CIR A, CLERMONT, FL, 34711, Clermont, FL 34711]()
2 beds
|2 baths
|1,503 sq ft
|Villa
3553 BELLAND CIR A, CLERMONT, FL, 34711
Community: Heritage Hills
MLS O6363333 • BHHS FLORIDA REALTY, Patti Kincaid
Del Webb Sunbridge
![2744 NATURE VIEW RD, ST CLOUD, FL, 34771, St Cloud, FL 34771]()
3 beds
|5 baths
|2,866 sq ft
|House
2744 NATURE VIEW RD, ST CLOUD, FL, 34771
Community: Del Webb Sunbridge
MLS V4946141 • PRIME REAL ESTATE, INC., Tresa Fla...
Arlington Ridge
![4358 ANTIETAM CREEK TRL, LEESBURG, FL, 3..., Leesburg, FL 34748]()
3 beds
|2 baths
|1,776 sq ft
|House
4358 ANTIETAM CREEK TRL, LEESBURG, FL, 3...
Community: Arlington Ridge
MLS G5105131 • RE/MAX SELECT PARTNERS, Edwin Budd
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The Villages®
![1001 MATTHEW AVE, THE VILLAGES, FL, 3215..., The Villages, FL 32159]()
2 beds
|2 baths
|1,149 sq ft
|Manufactured Home
1001 MATTHEW AVE, THE VILLAGES, FL, 3215...
Community: The Villages®
MLS G5104993 • COLDWELL BANKER VANGUARD LIFESTYLE...
Highland Fairways
![3535 SADDLEBROOK WAY, LAKELAND, FL, 3381..., Lakeland, FL 33810]()
3 beds
|2 baths
|2,145 sq ft
|House
3535 SADDLEBROOK WAY, LAKELAND, FL, 3381...
Community: Highland Fairways
MLS L4957644 • REGAL REAL ESTATE LLC, Debbie Ward...
Lake James
![7914 LAKE JAMES BLVD, LAKELAND, FL, 3381..., Lakeland, FL 33810]()
2 beds
|2 baths
|1,925 sq ft
|House
7914 LAKE JAMES BLVD, LAKELAND, FL, 3381...
Community: Lake James
MLS L4957618 • KELLER WILLIAMS REALTY SMART, Kim ...
Spruce Creek South
![17520 SE 95TH CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
2 beds
|2 baths
|1,008 sq ft
|House
17520 SE 95TH CT, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
MLS O6363989 • MARK SPAIN REAL ESTATE, Jeff Jones
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
![1009 FOREST BREEZE PATH, LEESBURG, FL, 3..., Leesburg, FL 34748]()
3 beds
|2 baths
|1,921 sq ft
|House
1009 FOREST BREEZE PATH, LEESBURG, FL, 3...
Community: Pennbrooke Fairways
MLS G5105107 • MORRIS REALTY AND INVESTMENTS, Mik...
The Lakes at Harmony
![3168 SONGBIRD CIR, HARMONY, FL, 34773, Harmony, FL 34773]()
3 beds
|2 baths
|1,850 sq ft
|House
3168 SONGBIRD CIR, HARMONY, FL, 34773
Community: The Lakes at Harmony
MLS 1063322 • Corcoran Connect LLC, Jeanine Corco...
The Timbers at Everlands
![1887 CERULEAN DR, PALM BAY, FL, 32907, Palm Bay, FL 32907]()
3 beds
|2 baths
|1,436 sq ft
|Townhouse
1887 CERULEAN DR, PALM BAY, FL, 32907
Community: The Timbers at Everlands
MLS A11923169 • The R.E. Resource Grp., Inc., Dar...
Pelican Bay Daytona Beach
![252 GULL DR, DAYTONA BEACH, FL, 32119, Daytona Beach, FL 32119]()
2 beds
|3 baths
|2,086 sq ft
|House
252 GULL DR, DAYTONA BEACH, FL, 32119
Community: Pelican Bay Daytona Beach
MLS V4946138 • ADAMS, CAMERON & CO., REALTORS, Do...
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Venetian Bay
![360 N AIRPORT RD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
2 beds
|3 baths
|1,837 sq ft
|Townhouse
360 N AIRPORT RD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS NS1086723 • THE KEYES COMPANY, Travous Dever
The Villages®
![16812 SE 86TH ALBANY AVE, THE VILLAGES, ..., The Villages, FL 32162]()
3 beds
|2 baths
|1,884 sq ft
|House
16812 SE 86TH ALBANY AVE, THE VILLAGES, ...
Community: The Villages®
MLS G5104478 • WORTH CLARK REALTY, Sam Wilson
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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.
