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Winter Park, FL 55+ active adult communities & homes for sale - Page 26
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
The Villages®
![17723 SE 81ST TIMBERWOOD TER, THE VILLAG..., The Villages, FL 32162]()
3 beds
|2 baths
|2,027 sq ft
|House
17723 SE 81ST TIMBERWOOD TER, THE VILLAG...
Community: The Villages®
MLS OM718904 • LPT REALTY, LLC, Gary Martin
The Villages®
![342 SAN MARINO DR, THE VILLAGES, FL, 321..., The Villages, FL 32159]()
2 beds
|2 baths
|1,230 sq ft
|House
342 SAN MARINO DR, THE VILLAGES, FL, 321...
Community: The Villages®
MLS OM719002 • CB/ELLISON RLTY WEST, Brian McCart...
Four Seasons at Orlando
![7977 HANSON BAY PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747]()
3 beds
|2 baths
|2,130 sq ft
|House
7977 HANSON BAY PL, KISSIMMEE, FL, 34747
Community: Four Seasons at Orlando
MLS O6382804 • REAL BROKER, LLC, Tyler Labod
The Villages®
![16672 SE 78TH LIVE OAK AVE, THE VILLAGES..., The Villages, FL 32162]()
3 beds
|2 baths
|1,850 sq ft
|House
16672 SE 78TH LIVE OAK AVE, THE VILLAGES...
Community: The Villages®
MLS O6381512 • COLDWELL BANKER REALTY, Bob Paulso...
Bridgewater at Viera
![963 GREAT BELT CIR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|3 baths
|2,532 sq ft
|House
963 GREAT BELT CIR, MELBOURNE, FL, 32940
Community: Bridgewater at Viera
MLS 1069578 • RE/MAX Aerospace Realty, Karla Bres...
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The Villages®
![3930 E TORCH LAKE DR, THE VILLAGES, FL, ..., The Villages, FL 32163]()
3 beds
|2 baths
|1,794 sq ft
|Villa
3930 E TORCH LAKE DR, THE VILLAGES, FL, ...
Community: The Villages®
MLS G5108262 • FLORIDA REALTY INVESTMENTS, Robyn ...
Venetian Bay
![3218 MODENA WAY, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168]()
3 beds
|2 baths
|2,269 sq ft
|House
3218 MODENA WAY, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
MLS NS1087319 • ENGEL & VOLKERS NEW SMYRNA, Amy A...
Highland Lakes
![5932 MCENROE CT, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,210 sq ft
|Villa
5932 MCENROE CT, LEESBURG, FL, 34748
Community: Highland Lakes
MLS S5143845 • WATSON REALTY CORP, James Joseph
Royal Highlands
![21849 TARTAN ST, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|2,074 sq ft
|House
21849 TARTAN ST, LEESBURG, FL, 34748
Community: Royal Highlands
MLS G5108275 • FLORIDA PLUS REALTY, LLC, Tonya Ti...
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 Country Club
![13760 SE 86TH TER, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,122 sq ft
|House
13760 SE 86TH TER, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS G5108263 • RE/MAX PREMIER REALTY LADY LK, Rob...
The Villages®
![9711 SE 171ST ARGYLL ST, THE VILLAGES, F..., The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
9711 SE 171ST ARGYLL ST, THE VILLAGES, F...
Community: The Villages®
MLS G5107046 • KELLER WILLIAMS CORNERSTONE RE, Ka...
American Village
![29 GREEN CIR, PALM COAST, FL, 32164, Palm Coast, FL 32164]()
3 beds
|2 baths
|1,604 sq ft
|House
29 GREEN CIR, PALM COAST, FL, 32164
Community: American Village
MLS FC316194 • DR HORTON REALTY INC., Charlie Rog...
Scottish Highlands
![822 DUNDEE CIR 822, LEESBURG, FL, 34788, Leesburg, FL 34788]()
2 beds
|2 baths
|1,414 sq ft
|House
822 DUNDEE CIR 822, LEESBURG, FL, 34788
Community: Scottish Highlands
MLS G5108264 • MORRIS REALTY AND INVESTMENTS, Jo ...
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Pennbrooke Fairways
![752 OLD OAKS LN, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,620 sq ft
|House
752 OLD OAKS LN, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS G5108177 • MAXREV LLC, Jayne Marvin
Indian River Colony Club
![1314 PILGRIM AVE, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
4 beds
|4 baths
|2,898 sq ft
|House
1314 PILGRIM AVE, MELBOURNE, FL, 32940
Community: Indian River Colony Club
MLS 1069484 • Four Star Real Estate LLC, Shellie ...
Highland Lakes
![26927 FOREST HILLS ST, LEESBURG, FL, 347..., Leesburg, FL 34748]()
3 beds
|2 baths
|1,580 sq ft
|House
26927 FOREST HILLS ST, LEESBURG, FL, 347...
Community: Highland Lakes
MLS G5108254 • FLORIDA PLUS REALTY, LLC, Simon Am...
Heritage Isle
![6528 VAN NESS DR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|3 baths
|2,006 sq ft
|House
6528 VAN NESS DR, MELBOURNE, FL, 32940
Community: Heritage Isle
MLS 1069459 • Arium Real Estate, LLC, Noah Lebkic...
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
![8301 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757]()
3 beds
|2 baths
|1,823 sq ft
|House
8301 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...
Community: Lakes of Mount Dora
MLS G5108256 • BAILEY AND SHAW REALTY LLC, Shawzi...
Halifax Plantation
![3145 CONNEMARA DR, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
3 beds
|3 baths
|2,384 sq ft
|House
3145 CONNEMARA DR, ORMOND BEACH, FL, 321...
Community: Halifax Plantation
MLS V4947388 • LPT REALTY, LLC, Svetlana Hardwick
Solivita
![189 LARGO DR, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5143815 • BORCHINI REALTY, Yamile Osorio Var...
Spruce Creek South
![9826 SE 178TH LN, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
2 beds
|2 baths
|1,312 sq ft
|House
9826 SE 178TH LN, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
MLS G5107726 • REALTY EXECUTIVES IN THE VILLAGES,...
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Indian River Colony Club
![1430 PATRIOT DR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|2 baths
|2,131 sq ft
|House
1430 PATRIOT DR, MELBOURNE, FL, 32940
Community: Indian River Colony Club
MLS 1069437 • Four Star Real Estate LLC, Shellie ...
The Villages®
![8442 COUNTY RD 109, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
3 beds
|2 baths
|1,664 sq ft
|Manufactured Home
8442 COUNTY RD 109, LADY LAKE, FL, 32159
Community: The Villages®
MLS G5108222 • REALTY EXECUTIVES IN THE VILLAGES,...
Solivita
![447 VILLA PARK RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS O6382686 • FLORIDA PLUS REALTY, LLC, Sarah Bo...
Royal Palm
![1328 COCONUT PALM CIR, PORT ORANGE, FL, ..., Port Orange, FL 32128]()
4 beds
|3 baths
|2,656 sq ft
|House
1328 COCONUT PALM CIR, PORT ORANGE, FL, ...
Community: Royal Palm
MLS 1223043 • Florida Investment Realty, Arun Red...
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®
![13877 COUNTY RD, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
4 beds
|2 baths
|1,960 sq ft
|Manufactured Home
13877 COUNTY RD, LADY LAKE, FL, 32159
Community: The Villages®
MLS G5108220 • ATLAS CENTRAL FLORIDA REALTY, Tiff...
Lakeside Landings
![5415 ADMIRAL WAY H5-102, OXFORD, FL, 344..., Oxford, FL 34484]()
2 beds
|2 baths
|1,281 sq ft
|Condo
5415 ADMIRAL WAY H5-102, OXFORD, FL, 344...
Community: Lakeside Landings
MLS G5108217 • LPT REALTY, LLC, Genie Muldoon
Lakeside Landings
![5105 JAREDS LANDING WAY, OXFORD, FL, 344..., Oxford, FL 34484]()
3 beds
|2 baths
|2,326 sq ft
|House
5105 JAREDS LANDING WAY, OXFORD, FL, 344...
Community: Lakeside Landings
MLS OM718783 • CHARLES RUTENBERG REALTY ORLANDO, ...
Latitude Margaritaville
![298 HANG LOOSE WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124]()
2 beds
|3 baths
|2,139 sq ft
|House
298 HANG LOOSE WAY, DAYTONA BEACH, FL, 3...
Community: Latitude Margaritaville
MLS 1223029 • Bob Hodges and Sons Realty, Kelley ...
Bridgewater at Viera
![9723 ALISTER DR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|2 baths
|1,565 sq ft
|House
9723 ALISTER DR, MELBOURNE, FL, 32940
Community: Bridgewater at Viera
MLS 1069393 • 1 Percent Lists FL's Finest, Karen ...
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Plantation at Leesburg
![4721 TARA VIEW RD, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,979 sq ft
|House
4721 TARA VIEW RD, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS O6380183 • KELLER WILLIAMS HERITAGE REALTY, R...
Legacy of Leesburg
![5352 TREASURE VIEW WAY, LEESBURG, FL, 34..., Leesburg, FL 34748]()
3 beds
|2 baths
|2,241 sq ft
|House
5352 TREASURE VIEW WAY, LEESBURG, FL, 34...
Community: Legacy of Leesburg
MLS G5108076 • FLORIDA PLUS REALTY, LLC, Christin...
Heritage Hills
![3538 FAIRWATERS CT B, CLERMONT, FL, 3471..., Clermont, FL 34711]()
2 beds
|2 baths
|1,374 sq ft
|Villa
3538 FAIRWATERS CT B, CLERMONT, FL, 3471...
Community: Heritage Hills
MLS G5107747 • KELLER WILLIAMS ELITE PARTNERS III...
Royal Highlands
![4741 INVERNESS DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,902 sq ft
|House
4741 INVERNESS DR, LEESBURG, FL, 34748
Community: Royal Highlands
MLS S5143859 • NONA LEGACY POWERED BY LA ROSA, Vi...
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.
Foxwood Lake Estates
![1631 FOXWAY DR, LAKELAND, FL, 33810, Lakeland, FL 33810]()
3 beds
|2 baths
|1,680 sq ft
|Manufactured Home
1631 FOXWAY DR, LAKELAND, FL, 33810
Community: Foxwood Lake Estates
MLS S5143840 • THE PROPERTY FIRM, Savina Delgado ...
The Villages®
![670 WOODBRIDGE WAY, THE VILLAGES, FL, 32..., The Villages, FL 32163]()
3 beds
|2 baths
|2,299 sq ft
|House
670 WOODBRIDGE WAY, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5108131 • RE/MAX PREMIER REALTY, Tammy Freil...
The Villages®
![1020 DUSTIN DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|1,240 sq ft
|Manufactured Home
1020 DUSTIN DR, LADY LAKE, FL, 32159
Community: The Villages®
MLS O6382426 • KELLER WILLIAMS CLASSIC, Francis Z...
Kings Ridge
![2302 EDMONTON CT, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS O6382577 • CENTURY 21 CARIOTI, Angelica Tomli...
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Foxwood Lake Estates
![1679 FOXWAY DR, LAKELAND, FL, 33810, Lakeland, FL 33810]()
2 beds
|2 baths
|1,248 sq ft
|Manufactured Home
1679 FOXWAY DR, LAKELAND, FL, 33810
Community: Foxwood Lake Estates
MLS L4959368 • COLDWELL BANKER REALTY, Kelley Bla...
Pelican Bay Daytona Beach
![636 BROWN PELICAN DR, DAYTONA BEACH, FL,..., Daytona Beach, FL 32119]()
3 beds
|2 baths
|1,484 sq ft
|Townhouse
636 BROWN PELICAN DR, DAYTONA BEACH, FL,...
Community: Pelican Bay Daytona Beach
MLS 1223010 • Simply Real Estate, Deana Frechette
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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.
