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Winter Park, FL 55+ active adult communities & homes for sale - Page 20
90 communities near Winter Park
2,398 homes near Winter Park
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4 rating (17 reviews)
![The Villages®]()
<$100k
- $2Ms
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
- $3Ms
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
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
- $1Ms
Grand Haven, Palm Coast, FL
New and Resale
|
Age-targeted
|
Built 1997 - present
|
1,901 homes
$100Ks
- $400Ks
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
- $400Ks
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
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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
3.8 rating (6 reviews)
![Trilogy® Orlando]()
$200Ks
- $600Ks
Trilogy® Orlando, Groveland, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2022
|
1,500 homes
5 rating (2 reviews)
![Heritage Isle]()
$200Ks
- $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)
![Royal Highlands]()
$200Ks
- $400Ks
Royal Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2006
|
1,500 homes
$400Ks
- $1Ms
Del Webb at Viera, Melbourne, FL
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
1,300 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
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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
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.
$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
- $800Ks
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
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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
- $800Ks
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
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.
4.1 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
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
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Questions? Call us:
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1 rating (1 reviews)
![Sullivan Ranch]()
$200Ks
- $700Ks
Sullivan Ranch, Mount Dora, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2020
|
692 homes
Solivita
![777 VINEYARD WAY, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS L4956640 • LOKATION, Chad Lindsey
Del Webb at Viera
![3132 TIDEPOOL PL, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|2 baths
|1,902 sq ft
|House
3132 TIDEPOOL PL, MELBOURNE, FL, 32940
Community: Del Webb at Viera
MLS 1059263 • Engel&Voelkers Melb Beachside, Marc...
Solivita
![1272 BONITA CANYON DR, POINCIANA, FL, 34..., Poinciana, FL 34759]()
2 beds
|2 baths
|1,705 sq ft
|House
1272 BONITA CANYON DR, POINCIANA, FL, 34...
Community: Solivita
MLS S5139891 • BORCHINI REALTY, Charles Borchini
The Villages®
![17353 SE 78TH HARMONY CIR, THE VILLAGES,..., The Villages, FL 32162]()
1 beds
|1 baths
|955 sq ft
|Villa
17353 SE 78TH HARMONY CIR, THE VILLAGES,...
Community: The Villages®
MLS G5105839 • REAL BROKER, LLC, Katy Kelly
Solivita
![307 MONTEREY ST, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5137888 • BORCHINI REALTY, Cherie Pontes
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The Villages®
![2211 BACHMAN PATH, THE VILLAGES, FL, 321..., The Villages, FL 32162]()
4 beds
|2 baths
|2,509 sq ft
|House
2211 BACHMAN PATH, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5105758 • REALTY EXECUTIVES IN THE VILLAGES,...
The Villages®
![7180 SE 172ND HAZELWOOD LOOP, THE VILLAG..., The Villages, FL 32162]()
3 beds
|2 baths
|1,918 sq ft
|House
7180 SE 172ND HAZELWOOD LOOP, THE VILLAG...
Community: The Villages®
MLS G5105470 • WORTH CLARK REALTY, Denise Marie T...
The Villages®
![2447 YOUNGMANN LOOP, THE VILLAGES, FL, 3..., The Villages, FL 32163]()
3 beds
|2 baths
|1,998 sq ft
|House
2447 YOUNGMANN LOOP, THE VILLAGES, FL, 3...
Community: The Villages®
MLS G5105808 • WORTH CLARK REALTY, Nancy Reynolds
The Villages®
![3327 DALKEITH TER, THE VILLAGES, FL, 321..., The Villages, FL 32163]()
3 beds
|2 baths
|2,124 sq ft
|House
3327 DALKEITH TER, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5102757 • REALTY EXECUTIVES IN THE VILLAGES,...
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®
![3374 CASTLEGATE CT, THE VILLAGES, FL, 32..., The Villages, FL 32163]()
2 beds
|2 baths
|1,156 sq ft
|Villa
3374 CASTLEGATE CT, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5103287 • VISIONARY PROPERTIES INC, Judy Blu...
Latitude Margaritaville
![962 ATTITUDE AVE, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124]()
3 beds
|2 baths
|1,771 sq ft
|House
962 ATTITUDE AVE, DAYTONA BEACH, FL, 321...
Community: Latitude Margaritaville
MLS NS1085688 • EXP REALTY LLC, Geri Davis
The Villages®
![1537 BARNWELL PL, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
3 beds
|2 baths
|1,406 sq ft
|Villa
1537 BARNWELL PL, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5101715 • REALTY EXECUTIVES IN THE VILLAGES,...
The Villages®
![859 KLINE ST, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,861 sq ft
|House
859 KLINE ST, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5099717 • WORTH CLARK REALTY, Chris Day
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The Villages®
![278 MATISSE AVE, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,966 sq ft
|House
278 MATISSE AVE, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5095422 • HOMESMART, Maria Czarnecki
The Villages®
![1496 LIME GROVE LN, THE VILLAGES, FL, 32..., The Villages, FL 32162]()
2 beds
|2 baths
|1,132 sq ft
|Villa
1496 LIME GROVE LN, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5098536 • RE/MAX PREMIER REALTY LADY LK, Oli...
Harbor Hills Country Club
![6152 TOPSAIL RD, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|1,552 sq ft
|House
6152 TOPSAIL RD, LADY LAKE, FL, 32159
Community: Harbor Hills Country Club
MLS G5094402 • MORRIS REALTY AND INVESTMENTS, The...
Harbor Hills Country Club
![38633 LAKEVIEW WALK, LADY LAKE, FL, 3215..., Lady Lake, FL 32159]()
4 beds
|2 baths
|2,322 sq ft
|House
38633 LAKEVIEW WALK, LADY LAKE, FL, 3215...
Community: Harbor Hills Country Club
MLS G5103679 • MORRIS REALTY AND INVESTMENTS, The...
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®
![752 MAYBANK LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
3 beds
|2 baths
|1,953 sq ft
|House
752 MAYBANK LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5099328 • RE/MAX PREMIER REALTY LADY LK, Mat...
The Villages®
![511 LOMA PASEO DR, THE VILLAGES, FL, 321..., The Villages, FL 32159]()
2 beds
|2 baths
|1,832 sq ft
|House
511 LOMA PASEO DR, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5103623 • RE/MAX PREMIER REALTY LADY LK, Mat...
The Villages®
![2552 MARIEL WAY, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,156 sq ft
|Villa
2552 MARIEL WAY, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5105857 • RE/MAX PREMIER REALTY LADY LK, Mat...
New
Venetian Bay
![3617 ROMEA CIR, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|1,824 sq ft
|Townhouse
3617 ROMEA CIR, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
MLS V4946540 • WATSON REALTY CORP., Katlin Davis
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Venetian Bay
![2929 BELLA FLORE TER, NEW SMYRNA BEACH, ..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|2,536 sq ft
|House
2929 BELLA FLORE TER, NEW SMYRNA BEACH, ...
Community: Venetian Bay
MLS NS1086742 • EXIT REAL ESTATE PROPERTY SOL, Ja...
Trilogy® Orlando
![363 ALCOVE DR, GROVELAND, FL, 34736, Groveland, FL 34736]()
2 beds
|2 baths
|1,568 sq ft
|House
363 ALCOVE DR, GROVELAND, FL, 34736
Community: Trilogy® Orlando
MLS O6335931 • MARK SPAIN REAL ESTATE, Christine ...
The Villages®
![17635 SE 92ND GRANTHAM TER, THE VILLAGES..., The Villages, FL 32162]()
2 beds
|2 baths
|1,237 sq ft
|House
17635 SE 92ND GRANTHAM TER, THE VILLAGES...
Community: The Villages®
MLS G5105536 • DOWN HOME REALTY, LLLP, Kevin Russ...
The Villages®
![438 GROVEWOOD PL, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
3 beds
|2 baths
|1,397 sq ft
|Villa
438 GROVEWOOD PL, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5105373 • CENTURY 21 ALTON CLARK, Regina Rod...
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®
![904 MAYNARD PATH, THE VILLAGES, FL, 3216..., The Villages, FL 32163]()
3 beds
|2 baths
|1,944 sq ft
|House
904 MAYNARD PATH, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5101230 • COLDWELL BANKER VANGUARD EDGE, Mar...
The Villages®
![16938 SE 94TH SUNNYBROOK CIR, THE VILLAG..., The Villages, FL 32162]()
2 beds
|2 baths
|1,163 sq ft
|House
16938 SE 94TH SUNNYBROOK CIR, THE VILLAG...
Community: The Villages®
MLS G5098750 • REALTY EXECUTIVES IN THE VILLAGES,...
Latitude Margaritaville
![1082 CASTAWAY CT, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,684 sq ft
|House
1082 CASTAWAY CT, DAYTONA BEACH, FL, 321...
Community: Latitude Margaritaville
MLS 1212471 • Keller Williams Realty Florida Part...
The Villages®
![5609 HANCOCK DR, WILDWOOD, FL, 34785, Wildwood, FL 34785]()
2 beds
|1 baths
|660 sq ft
|Mobile Home
5609 HANCOCK DR, WILDWOOD, FL, 34785
Community: The Villages®
MLS O6370253 • FLORIDA REALTY INVESTMENTS, Tina V...
Grand Haven
![8 N VILLAGE DR, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
MLS FC308288 • COASTAL GATEWAY REAL ESTATE GR, Ra...
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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
New
The Villages®
![4515 BIGGS PL, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|3 baths
|2,837 sq ft
|House
4515 BIGGS PL, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5106121 • LPT REALTY, LLC, Kerry Hanson
The Villages®
![17211 SE 85TH WILLOWICK CIR, THE VILLAGE..., The Villages, FL 32162]()
3 beds
|2 baths
|2,350 sq ft
|House
17211 SE 85TH WILLOWICK CIR, THE VILLAGE...
Community: The Villages®
MLS G5105903 • COLDWELL BANKER VANGUARD LIFESTYLE...
The Villages®
![1757 FLAGSTONE TER, THE VILLAGES, FL, 32..., The Villages, FL 32162]()
3 beds
|2 baths
|1,602 sq ft
|House
1757 FLAGSTONE TER, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5104539 • RE/MAX PREMIER REALTY LADY LK, Guy...
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®
![879 CHAPMAN LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
3 beds
|2 baths
|1,621 sq ft
|House
879 CHAPMAN LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5105108 • LPT REALTY, LLC, Dave Monty
The Villages®
![926 LONG LEAF LN, THE VILLAGES, FL, 3216..., The Villages, FL 32163]()
3 beds
|2 baths
|1,541 sq ft
|House
926 LONG LEAF LN, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5105619 • ERA GRIZZARD REAL ESTATE, Melissa ...
The Villages®
![978 SMYRNA ST, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,397 sq ft
|Villa
978 SMYRNA ST, THE VILLAGES, FL, 32162
Community: The Villages®
MLS TB8449535 • CHARLES RUTENBERG REALTY INC, Bil...
The Villages®
![1220 DUSTIN DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|1,056 sq ft
|Manufactured Home
1220 DUSTIN DR, LADY LAKE, FL, 32159
Community: The Villages®
MLS O6365626 • NEST SEEKERS FLORIDA, LLC, Rudy Si...
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(888) 625-4885
The Villages®
![362 ARBELLA LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
2 beds
|2 baths
|1,393 sq ft
|House
362 ARBELLA LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5098347 • CHARLES RUTENBERG REALTY ORLANDO, ...
The Villages®
![17720 SE 84TH PEYTON CT, THE VILLAGES, F..., The Villages, FL 32162]()
3 beds
|2 baths
|1,733 sq ft
|Villa
17720 SE 84TH PEYTON CT, THE VILLAGES, F...
Community: The Villages®
MLS G5101747 • FLORIDA FINE HOMES REALTY, LLC, Je...
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2,398
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REIN updates its listings on a daily basis. Data last updated: Jan 11, 2026.
This application does not include information on all of the properties available for sale at this time.
