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Winter Park, FL 55+ active adult communities & homes for sale - Page 59
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 (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
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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
Grand Haven
![67 LAGARE ST, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
MLS FC310984 • TAKE ACTION PROPERTIES, LLC, Lucia...
Ridgehaven
![457 BROOKHAVEN TRL, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,487 sq ft
|House
457 BROOKHAVEN TRL, ORMOND BEACH, FL, 32...
Community: Ridgehaven
MLS O6323942 • MERITAGE HOMES OF FL REALTY, Bryan...
The Villages®
![4216 BALCHARAN TER, THE VILLAGES, FL, 32..., The Villages, FL 32163]()
3 beds
|2 baths
|1,924 sq ft
|House
4216 BALCHARAN TER, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5099116 • WORTH CLARK REALTY, Haskew Hayes
Heritage Isle
![3029 VALLEJO WAY, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
2 beds
|2 baths
|1,532 sq ft
|Townhouse
3029 VALLEJO WAY, MELBOURNE, FL, 32940
Community: Heritage Isle
MLS 1050635 • Florida East Coast Real Estate, Lyn...
Royal Highlands
![4738 ST ANDREWS ARC, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,892 sq ft
|House
4738 ST ANDREWS ARC, LEESBURG, FL, 34748
Community: Royal Highlands
MLS O6323322 • CORCORAN PREMIER REALTY, Robert We...
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Arlington Ridge
![3507 ARLINGTON RIDGE BLVD, LEESBURG, FL,..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,476 sq ft
|House
3507 ARLINGTON RIDGE BLVD, LEESBURG, FL,...
Community: Arlington Ridge
MLS G5099008 • WATSON REALTY CORP, Nancy McCloske...
The Villages®
![1722 BUGLE TER, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,667 sq ft
|House
1722 BUGLE TER, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5098901 • COLDWELL BANKER VANGUARD LIFESTYLE...
Lake Ashton
![5200 PEBBLE BEACH BLVD, WINTER HAVEN, FL..., Winter Haven, FL 33884]()
3 beds
|2 baths
|2,443 sq ft
|House
5200 PEBBLE BEACH BLVD, WINTER HAVEN, FL...
Community: Lake Ashton
MLS P4935325 • LAKE ASHTON REALTY INC., Lori Raat...
Summer Trees
![79 CYPRESS POND RD 79, PORT ORANGE, FL, ..., Port Orange, FL 32128]()
2 beds
|2 baths
|888 sq ft
|Condo
79 CYPRESS POND RD 79, PORT ORANGE, FL, ...
Community: Summer Trees
MLS V4943507 • EXIT BEACH REALTY, Jan Baran
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.
Summer Trees
![79 CYPRESS POND RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128]()
2 beds
|2 baths
|1,300 sq ft
|House
79 CYPRESS POND RD, PORT ORANGE, FL, 321...
Community: Summer Trees
MLS 1215083 • EXIT Beach Realty, Jan Baran
The Lakes at Harmony
![3184 SONGBIRD CIR, HARMONY, FL, 34773, Harmony, FL 34773]()
3 beds
|2 baths
|1,852 sq ft
|House
3184 SONGBIRD CIR, HARMONY, FL, 34773
Community: The Lakes at Harmony
MLS S5129784 • WEICHERT REALTORS HALLMARK PRO, Ba...
Del Webb Sunbridge
![2698 RIVER CREEK LN, SAINT CLOUD, FL, 34..., Saint Cloud, FL 34771]()
3 beds
|3 baths
|2,080 sq ft
|House
2698 RIVER CREEK LN, SAINT CLOUD, FL, 34...
Community: Del Webb Sunbridge
MLS O6322425 • REAL LIVING R E SOLUTIONS, Ladd Ts...
Spruce Creek Country Club
![12855 SE 92ND COURT RD, SUMMERFIELD, FL,..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,995 sq ft
|House
12855 SE 92ND COURT RD, SUMMERFIELD, FL,...
Community: Spruce Creek Country Club
MLS OM704508 • REALTY ONE GROUP DAVALLS, David St...
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Harbor Hills Country Club
![5235 GREENS DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
4 beds
|4 baths
|3,836 sq ft
|House
5235 GREENS DR, LADY LAKE, FL, 32159
Community: Harbor Hills Country Club
MLS G5098733 • MORRIS REALTY AND INVESTMENTS, The...
The Villages®
![902 ROSE LN, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,036 sq ft
|Manufactured Home
902 ROSE LN, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5098839 • RE/MAX PREMIER REALTY LADY LK, Cur...
Carlsberg Estates on Lake Suzanne
![464 LAKE SUZANNE DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859]()
3 beds
|2 baths
|1,429 sq ft
|House
464 LAKE SUZANNE DR, LAKE WALES, FL, 338...
Community: Carlsberg Estates on Lake Suzanne
MLS P4935255 • CENTURY 21 MYERS REALTY LAKE WALES...
Arlington Ridge
![26917 WHITE PLAINS WAY, LEESBURG, FL, 34..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,251 sq ft
|House
26917 WHITE PLAINS WAY, LEESBURG, FL, 34...
Community: Arlington Ridge
MLS G5097949 • HANSON REAL ESTATE GROUP, INC., Le...
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®
![1725 HILTON HEAD BLVD, LADY LAKE, FL, 32..., Lady Lake, FL 32159]()
2 beds
|2 baths
|1,092 sq ft
|Manufactured Home
1725 HILTON HEAD BLVD, LADY LAKE, FL, 32...
Community: The Villages®
MLS O6321543 • ORLANDO HOME DEALER LLC, Kristal M...
Solivita
![418 TREVISO DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5129151 • BELLA VERDE REALTY LLC, Debra DiCi...
Pelican Bay Daytona Beach
![133 BLUE HERON DR D, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119]()
2 beds
|2 baths
|1,242 sq ft
|Condo
133 BLUE HERON DR D, DAYTONA BEACH, FL, ...
Community: Pelican Bay Daytona Beach
MLS FC310736 • EXIT REALTY FIRST CHOICE, Kathy Ke...
Sullivan Ranch
![30308 CHEVAL ST, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
3 beds
|2 baths
|1,851 sq ft
|House
30308 CHEVAL ST, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
MLS O6319648 • LPT REALTY, LLC, Tony Tate
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Venetian Bay
![349 CARYOTA CT, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168]()
3 beds
|2 baths
|1,520 sq ft
|House
349 CARYOTA CT, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
MLS NS1085211 • CENTURY 21 SUNDANCE REALTY, Bryan...
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, ...
Cresswind at Victoria Gardens
![600 GARDEN CLUB DR, DELAND, FL, 32724, Deland, FL 32724]()
4 beds
|3 baths
|2,569 sq ft
|House
600 GARDEN CLUB DR, DELAND, FL, 32724
Community: Cresswind at Victoria Gardens
MLS O6308655 • CHARLES RUTENBERG REALTY ORLANDO, ...
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...
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.
Del Webb Minneola
![2759 PURPLE MEADOW CT, MINNEOLA, FL, 347..., Minneola, FL 34715]()
2 beds
|2 baths
|1,405 sq ft
|House
2759 PURPLE MEADOW CT, MINNEOLA, FL, 347...
Community: Del Webb Minneola
MLS O6319407 • RE/MAX SELECT GROUP, Mike Mondello
Legacy of Leesburg
![27328 PINE STRAW RD, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,894 sq ft
|House
27328 PINE STRAW RD, LEESBURG, FL, 34748
Community: Legacy of Leesburg
MLS G5098428 • VANGIE BERRY SIGNATURE REALTY, Ang...
Halifax Plantation
![3132 CONNEMARA DR, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,670 sq ft
|Townhouse
3132 CONNEMARA DR, ORMOND BEACH, FL, 321...
Community: Halifax Plantation
MLS FC310573 • ADAMS, CAMERON & CO., REALTORS, Al...
Highland Lakes
![5507 LAVER ST, LEESBURG, FL, 34748, Leesburg, FL 34748]()
MLS G5098355 • FLORIDA PLUS REALTY, LLC, Christin...
Lake James
![7770 LAKE JAMES BLVD, LAKELAND, FL, 3381..., Lakeland, FL 33810]()
2 beds
|2 baths
|1,990 sq ft
|House
7770 LAKE JAMES BLVD, LAKELAND, FL, 3381...
Community: Lake James
MLS L4953716 • KELLER WILLIAMS REALTY SMART, Joe ...
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Lakes at Laurel Highlands
![2062 BLUE HIGHLANDS DR, LAKELAND, FL, 33..., Lakeland, FL 33811]()
5 beds
|3 baths
|2,696 sq ft
|House
2062 BLUE HIGHLANDS DR, LAKELAND, FL, 33...
Community: Lakes at Laurel Highlands
MLS L4953737 • 54 REALTY LLC, Jordan Prais
Lake Ashton
![4188 MUIRFIELD LOOP, LAKE WALES, FL, 338..., Lake Wales, FL 33859]()
2 beds
|2 baths
|1,520 sq ft
|House
4188 MUIRFIELD LOOP, LAKE WALES, FL, 338...
Community: Lake Ashton
MLS L4953642 • COLDWELL BANKER REALTY, Lori Edwar...
Trilogy® Orlando
![101 FLAME VINE WAY, GROVELAND, FL, 34736, Groveland, FL 34736]()
3 beds
|2 baths
|1,794 sq ft
|House
101 FLAME VINE WAY, GROVELAND, FL, 34736
Community: Trilogy® Orlando
MLS G5098187 • COMMUNITY ELITE REALTY, Nancy Aitk...
Plantation Bay Golf & Country Club
![829 PINEWOOD DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|3 baths
|2,101 sq ft
|Townhouse
829 PINEWOOD DR, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS FC310286 • VENTURE DEVELOPMENT REALTY,INC, El...
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.
Spruce Creek South
![17533 SE 96TH CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
2 beds
|2 baths
|1,534 sq ft
|House
17533 SE 96TH CT, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
MLS G5097960 • RE/MAX PREMIER REALTY LADY LK, Ger...
Harbor Hills Country Club
![6008 APEX WAY, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
4 beds
|3 baths
|3,432 sq ft
|House
6008 APEX WAY, LADY LAKE, FL, 32159
Community: Harbor Hills Country Club
MLS G5098078 • CENTURY 21 ALTON CLARK, Regina Rod...
Spruce Creek Country Club
![9588 SE 124TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,979 sq ft
|House
9588 SE 124TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek Country Club
MLS G5097996 • RE/MAX PREMIER REALTY LADY LK, Rob...
Arlington Ridge
![4110 ARLINGTON RIDGE BLVD, LEESBURG, FL,..., Leesburg, FL 34748]()
3 beds
|2 baths
|1,857 sq ft
|House
4110 ARLINGTON RIDGE BLVD, LEESBURG, FL,...
Community: Arlington Ridge
MLS O6287135 • KELLER WILLIAMS HERITAGE REALTY, P...
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Spruce Creek South
![9499 SE 174TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,678 sq ft
|House
9499 SE 174TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
MLS G5097972 • EXP REALTY LLC, Brenda Bell
Solivita
![516 MILLIFIORA LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5128269 • TRANSCEND REALTY, Steven Friedland
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2,513
homes
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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.
