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Winter Park, FL 55+ active adult communities & homes for sale - Page 12
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
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 (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 (8 reviews)
![Royal Highlands]()
$200ks
- $400ks
Royal Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2006
|
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
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
1 rating (1 reviews)
![Sullivan Ranch]()
$200ks
- $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2020
|
692 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
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.
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
5 rating (8 reviews)
![Pennbrooke Fairways]()
<$100k
- $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1980 - 2004
|
1,200 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
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
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
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
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
Tohoqua Reserve, Kissimmee, FL
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
258 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
Del Webb Sunbridge
![2900 VOYAGER AVE, ST CLOUD, FL, 34771, St Cloud, FL 34771]()
3 beds
|3 baths
|1,767 sq ft
|Townhouse
2900 VOYAGER AVE, ST CLOUD, FL, 34771
Community: Del Webb Sunbridge
MLS G5109893 • OLYMPUS EXECUTIVE REALTY INC, Nanc...
Plantation Bay Golf & Country Club
![534 WINGSPAN DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
4 beds
|4 baths
|3,713 sq ft
|House
534 WINGSPAN DR, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS FC317085 • VENTURE DEVELOPMENT REALTY,INC, El...
Plantation Bay Golf & Country Club
![409 SEABROOK RD, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|2 baths
|2,153 sq ft
|House
409 SEABROOK RD, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS 1224347 • Adams, Cameron & Co., Realtors, Jer...
Del Webb Orlando
![349 TOLDEDO RD, DAVENPORT, FL, 33837, Davenport, FL 33837]()
2 beds
|2 baths
|1,468 sq ft
|House
349 TOLDEDO RD, DAVENPORT, FL, 33837
Community: Del Webb Orlando
MLS S5146108 • RIDGE REALTY GROUP LLC, Deborah Ba...
The Villages®
![1271 WHEELING WAY, THE VILLAGES, FL, 321..., The Villages, FL 32162]()
3 beds
|2 baths
|2,088 sq ft
|House
1271 WHEELING WAY, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5109606 • REALTY EXECUTIVES IN THE VILLAGES,...
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The Villages®
![3776 E TORCH LAKE DR, THE VILLAGES, FL, ..., The Villages, FL 32163]()
3 beds
|2 baths
|1,851 sq ft
|Villa
3776 E TORCH LAKE DR, THE VILLAGES, FL, ...
Community: The Villages®
MLS G5109815 • REALTY EXECUTIVES IN THE VILLAGES,...
The Villages®
![771 FENWICK LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32163]()
2 beds
|2 baths
|1,275 sq ft
|House
771 FENWICK LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5109627 • REALTY EXECUTIVES IN THE VILLAGES,...
Gatherings of Lake Nona
![7521 LAUREATE BLVD 5306, ORLANDO, FL, 32..., Orlando, FL 32827]()
2 beds
|2 baths
|1,549 sq ft
|Condo
7521 LAUREATE BLVD 5306, ORLANDO, FL, 32...
Community: Gatherings of Lake Nona
MLS O6391661 • THE WILKINS WAY LLC, Pamela Graben...
The Villages®
![529 RAINBOW BLVD, THE VILLAGES, FL, 3215..., The Villages, FL 32159]()
2 beds
|2 baths
|1,344 sq ft
|Manufactured Home
529 RAINBOW BLVD, THE VILLAGES, FL, 3215...
Community: The Villages®
MLS G5109877 • CENTURY 21 ALTON CLARK, Kathi Hill
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 Hills
![4052 SERENA LN, CLERMONT, FL, 34711, Clermont, FL 34711]()
3 beds
|2 baths
|1,672 sq ft
|House
4052 SERENA LN, CLERMONT, FL, 34711
Community: Heritage Hills
MLS O6392318 • GLOBAL REALTY INTERNATIONAL, Eliza...
Harbor Hills Country Club
![5414 SANDY HILL LN, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
3 beds
|2 baths
|2,123 sq ft
|House
5414 SANDY HILL LN, LADY LAKE, FL, 32159
Community: Harbor Hills Country Club
MLS G5109865 • CHARLES RUTENBERG REALTY ORLANDO, ...
The Villages®
![16867 SE 80TH ASHGROVE TER, THE VILLAGES..., The Villages, FL 32162]()
3 beds
|2 baths
|1,565 sq ft
|Villa
16867 SE 80TH ASHGROVE TER, THE VILLAGES...
Community: The Villages®
MLS G5109736 • KELLER WILLIAMS ELITE PARTNERS III...
The Villages®
![2558 CARRINGTON CT, THE VILLAGES, FL, 32..., The Villages, FL 32162]()
2 beds
|2 baths
|1,156 sq ft
|Villa
2558 CARRINGTON CT, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5109685 • KELLER WILLIAMS CORNERSTONE RE, Ka...
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Questions? Call us:
(888) 625-4885
Scottish Highlands
![506 GALLOWAY CT, LEESBURG, FL, 34788, Leesburg, FL 34788]()
3 beds
|2 baths
|1,524 sq ft
|House
506 GALLOWAY CT, LEESBURG, FL, 34788
Community: Scottish Highlands
MLS G5109874 • KELLER WILLIAMS ELITE PARTNERS III...
The Villages®
![1967 LAKE RIDGE DR, THE VILLAGES, FL, 32..., The Villages, FL 32162]()
3 beds
|2 baths
|2,911 sq ft
|House
1967 LAKE RIDGE DR, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5109576 • REALTY EXECUTIVES IN THE VILLAGES,...
Venetian Bay
![3359 W LOCANDA CIR, NEW SMYRNA BEACH, FL..., New Smyrna Beach, FL 32168]()
4 beds
|4 baths
|3,045 sq ft
|House
3359 W LOCANDA CIR, NEW SMYRNA BEACH, FL...
Community: Venetian Bay
MLS O6391814 • EXP REALTY LLC, Martha Grasty
Vienna Square
![1678 LINZ CT, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884]()
2 beds
|2 baths
|1,158 sq ft
|House
1678 LINZ CT, WINTER HAVEN, FL, 33884
Community: Vienna Square
MLS L4960316 • COLDWELL BANKER REALTY, Bryan Dick...
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.
Sandpiper Golf & Country Club
![6205 PEACOCK RUN, LAKELAND, FL, 33809, Lakeland, FL 33809]()
2 beds
|2 baths
|1,484 sq ft
|House
6205 PEACOCK RUN, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS L4960346 • AMPLIFY REAL ESTATE SERVICES FL, D...
The Villages®
![3079 CORDGRASS CT, THE VILLAGES, FL, 321..., The Villages, FL 32163]()
2 beds
|2 baths
|1,227 sq ft
|House
3079 CORDGRASS CT, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5109653 • KELLER WILLIAMS CORNERSTONE RE, Wi...
Cresswind at Victoria Gardens
![314 BELLINGRATH TER, DELAND, FL, 32724, Deland, FL 32724]()
4 beds
|3 baths
|2,528 sq ft
|House
314 BELLINGRATH TER, DELAND, FL, 32724
Community: Cresswind at Victoria Gardens
MLS V4947579 • REALTY PROS ASSURED, Mary Maholias
The Villages®
![9200 SE 179TH WESLEY ST, THE VILLAGES, F..., The Villages, FL 32162]()
2 beds
|2 baths
|1,136 sq ft
|House
9200 SE 179TH WESLEY ST, THE VILLAGES, F...
Community: The Villages®
MLS G5109863 • LPT REALTY, LLC, Genie Muldoon
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The Villages®
![2752 IRIS WAY, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,492 sq ft
|House
2752 IRIS WAY, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5109775 • SALLY LOVE REAL ESTATE, Julie Nay ...
Bridgewater at Viera
![2789 MILLENNIUM CIR, MELBOURNE, FL, 3294..., Melbourne, FL 32940]()
3 beds
|3 baths
|2,014 sq ft
|House
2789 MILLENNIUM CIR, MELBOURNE, FL, 3294...
Community: Bridgewater at Viera
MLS 1072438 • HomeSmart Coastal Realty, Julie Loc...
Bridgewater at Viera
![2303 GREAT BELT CIR, MELBOURNE, FL, 3294..., Melbourne, FL 32940]()
3 beds
|4 baths
|2,389 sq ft
|House
2303 GREAT BELT CIR, MELBOURNE, FL, 3294...
Community: Bridgewater at Viera
MLS 1072451 • Ellingson Properties, Gregory Ellin...
The Villages®
![2105 ZARAGOZA PL, THE VILLAGES, FL, 3215..., The Villages, FL 32159]()
3 beds
|2 baths
|2,291 sq ft
|House
2105 ZARAGOZA PL, THE VILLAGES, FL, 3215...
Community: The Villages®
MLS G5109818 • COLDWELL BANKER REALTY, William Pe...
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®
![2055 HYDRANGEA AVE, THE VILLAGES, FL, 32..., The Villages, FL 32162]()
3 beds
|2 baths
|1,398 sq ft
|Villa
2055 HYDRANGEA AVE, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5109806 • REALTY EXECUTIVES IN THE VILLAGES,...
Cresswind DeLand
![1281 TWIN FARMS CT, DELAND, FL, 32724, Deland, FL 32724]()
2 beds
|2 baths
|1,668 sq ft
|House
1281 TWIN FARMS CT, DELAND, FL, 32724
Community: Cresswind DeLand
MLS W7884058 • MALTBIE REALTY GROUP, Bill Maltbie
Del Webb at Viera
![9108 SPLASHING DR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|3 baths
|2,301 sq ft
|House
9108 SPLASHING DR, MELBOURNE, FL, 32940
Community: Del Webb at Viera
MLS O6392238 • PULTE REALTY OF NORTH FLORIDA LLC,...
Cresswind DeLand
![1314 CRESSWIND BLVD, DELAND, FL, 32724, Deland, FL 32724]()
2 beds
|2 baths
|1,968 sq ft
|House
1314 CRESSWIND BLVD, DELAND, FL, 32724
Community: Cresswind DeLand
MLS W7884057 • MALTBIE REALTY GROUP, Bill Maltbie
The Villages®
![3001 SANDY LN, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,542 sq ft
|House
3001 SANDY LN, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5109661 • KELLER WILLIAMS ELITE PARTNERS III...
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Questions? Call us:
(888) 625-4885
Solivita
![777 VINEYARD WAY, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5146159 • BORCHINI REALTY, Edie Stauffer
Latitude Margaritaville
![544 LOST SHAKER WAY, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,608 sq ft
|Villa
544 LOST SHAKER WAY, DAYTONA BEACH, FL, ...
Community: Latitude Margaritaville
MLS V4947917 • KELLER WILLIAMS RLTY FL. PARTN, Ha...
Latitude Margaritaville
![896 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,563 sq ft
|House
896 CORAL REEF WAY, DAYTONA BEACH, FL, 3...
Community: Latitude Margaritaville
MLS FC317039 • KELLER WILLIAMS RLTY FL. PARTN, Ta...
The Villages®
![2677 ENGLISH IVY CIR, THE VILLAGES, FL, ..., The Villages, FL 32162]()
3 beds
|2 baths
|1,240 sq ft
|House
2677 ENGLISH IVY CIR, THE VILLAGES, FL, ...
Community: The Villages®
MLS G5109733 • RE/MAX PREMIER REALTY, Guy William...
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.
Sullivan Ranch
![30112 KLADRUBY PT, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
3 beds
|2 baths
|2,144 sq ft
|House
30112 KLADRUBY PT, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
MLS G5109833 • ERA GRIZZARD REAL ESTATE, Jeanne S...
Twin Lakes
![2520 YELLOW BRICK RD, ST CLOUD, FL, 3477..., St Cloud, FL 34772]()
2 beds
|2 baths
|1,346 sq ft
|Villa
2520 YELLOW BRICK RD, ST CLOUD, FL, 3477...
Community: Twin Lakes
MLS O6391811 • CHARLES RUTENBERG REALTY ORLANDO, ...
The Villages®
![611 LISBON LN, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,721 sq ft
|House
611 LISBON LN, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5109564 • LPT REALTY, LLC, Dick Betts
Vienna Square
![2350 SALZBURG LOOP, WINTER HAVEN, FL, 33..., Winter Haven, FL 33884]()
2 beds
|2 baths
|1,521 sq ft
|House
2350 SALZBURG LOOP, WINTER HAVEN, FL, 33...
Community: Vienna Square
MLS P4938176 • CENTURY 21 WATSON & MYERS REALTY, ...
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The Villages®
![9280 SE 179TH WESLEY ST, THE VILLAGES, F..., The Villages, FL 32162]()
3 beds
|2 baths
|1,527 sq ft
|House
9280 SE 179TH WESLEY ST, THE VILLAGES, F...
Community: The Villages®
MLS G5109082 • FLORIDA FINE HOMES REALTY, LLC, Ca...
The Villages®
![313 GONZALES PL, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|1,240 sq ft
|House
313 GONZALES PL, LADY LAKE, FL, 32159
Community: The Villages®
MLS O6392102 • WATERFRONT REALTY GROUP INC, Jason...
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2,513
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REIN updates its listings on a daily basis. Data last updated: Apr 10, 2026.
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