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Winter Park, FL 55+ active adult communities & homes for sale - Page 48
90 communities near Winter Park
2,377 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
- $4Ms
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
5 rating (2 reviews)
![Heritage Isle]()
$200Ks
- $500Ks
Heritage Isle, Viera, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2017
|
1,500 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
Download the Ultimate 55+ Homebuying Guide
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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)
![VillageWalk at Lake Nona]()
$300Ks
- $1Ms
VillageWalk at Lake Nona, Orlando, FL
Resale Only
|
Age-targeted
|
Built 2006 - 2016
|
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
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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]()
$300Ks
- $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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1 rating (1 reviews)
![Sullivan Ranch]()
$200Ks
- $700Ks
Sullivan Ranch, Mount Dora, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2020
|
692 homes
Royal Highlands
![21650 STIRLING PASS, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,469 sq ft
|House
21650 STIRLING PASS, LEESBURG, FL, 34748
Community: Royal Highlands
MLS G5102999 • FLORIDA PLUS REALTY, LLC, Tonya Ti...
The Villages®
![16966 SE 94TH SUNNYBROOK CIR, THE VILLAG..., The Villages, FL 32162]()
2 beds
|2 baths
|1,186 sq ft
|Villa
16966 SE 94TH SUNNYBROOK CIR, THE VILLAG...
Community: The Villages®
MLS G5104483 • VILLAGE VALET REALTY LLC, Grace St...
The Villages®
![2282 SHEEHAN ST, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
2 beds
|2 baths
|1,227 sq ft
|Villa
2282 SHEEHAN ST, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5104320 • ATLAS CENTRAL FLORIDA REALTY, Mich...
The Villages®
![2907 BARBOZA DR, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,156 sq ft
|Villa
2907 BARBOZA DR, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5090646 • FLORIDA FINE HOMES REALTY, LLC, Ca...
Indian River Colony Club
![1375 MAYFLOWER AVE, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|2 baths
|2,010 sq ft
|House
1375 MAYFLOWER AVE, MELBOURNE, FL, 32940
Community: Indian River Colony Club
MLS 1044056 • Four Star Real Estate LLC, Shellie ...
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Pelican Bay Daytona Beach
![144 HERRING GULL CT, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119]()
3 beds
|2 baths
|1,702 sq ft
|House
144 HERRING GULL CT, DAYTONA BEACH, FL, ...
Community: Pelican Bay Daytona Beach
MLS 1220227 • Newberry Realty & Development Group...
Del Webb Sunbridge
![2695 RIVER CREEK LN, SAINT CLOUD, FL, 34..., Saint Cloud, FL 34771]()
2 beds
|2 baths
|2,184 sq ft
|House
2695 RIVER CREEK LN, SAINT CLOUD, FL, 34...
Community: Del Webb Sunbridge
MLS S5138523 • ORLANDO REGIONAL REALTY, Heike Kna...
Lake Ashton
![4432 WATERFORD DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859]()
2 beds
|2 baths
|1,605 sq ft
|House
4432 WATERFORD DR, LAKE WALES, FL, 33859
Community: Lake Ashton
MLS P4931651 • CENTURY 21 MYERS REALTY LAKE WALES...
Latitude Margaritaville
![192 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,321 sq ft
|House
192 GYPSY PALACE LN, DAYTONA BEACH, FL, ...
Community: Latitude Margaritaville
MLS 1217073 • 386RealEstate.com, Kevin Kling
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.
Grand Haven
![26 N PARK CIR, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
MLS FC312776 • WATSON REALTY CORP, Taffi McLaughl...
The Villages®
![1067 CARVER CT, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
2 beds
|2 baths
|1,270 sq ft
|Villa
1067 CARVER CT, THE VILLAGES, FL, 32163
Community: The Villages®
MLS TB8448232 • WWW.HOMEZU.COM, Jason Saphire
The Lakes at Harmony
![3447 FEATHERGRASS CT, HARMONY, FL, 34773, Harmony, FL 34773]()
5 beds
|4 baths
|3,300 sq ft
|House
3447 FEATHERGRASS CT, HARMONY, FL, 34773
Community: The Lakes at Harmony
MLS O6356968 • THE AGENCY ORLANDO, Patrick Lynn
The Villages®
![2053 BEECHER PATH, THE VILLAGES, FL, 321..., The Villages, FL 32162]()
3 beds
|2 baths
|1,876 sq ft
|House
2053 BEECHER PATH, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5104145 • FONTANA REALTY INC., Tina Teraskie...
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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...
Heritage Isle
![3112 GRAYSON DR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
4 beds
|3 baths
|1,988 sq ft
|House
3112 GRAYSON DR, MELBOURNE, FL, 32940
Community: Heritage Isle
MLS 1063657 • Keller Williams Realty Brevard, Ana...
Stonecrest
![17680 SE 121ST CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,581 sq ft
|House
17680 SE 121ST CT, SUMMERFIELD, FL, 3449...
Community: Stonecrest
MLS R4909801 • BLACK TIE REAL ESTATE PROFESSIONAL...
Royal Highlands
![5518 QUEEN VICTORIA DR, LEESBURG, FL, 34..., Leesburg, FL 34748]()
3 beds
|2 baths
|1,757 sq ft
|House
5518 QUEEN VICTORIA DR, LEESBURG, FL, 34...
Community: Royal Highlands
MLS O6343470 • KELLER WILLIAMS ADVANTAGE III, Ern...
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.
Legacy of Leesburg
![27303 STONEY BROOK DR, LEESBURG, FL, 347..., Leesburg, FL 34748]()
3 beds
|2 baths
|2,210 sq ft
|House
27303 STONEY BROOK DR, LEESBURG, FL, 347...
Community: Legacy of Leesburg
MLS G5101669 • WHEATLEY REALTY GROUP, Laura Monte...
Heritage Hills
![3201 SONESTA CT B, CLERMONT, FL, 34711, Clermont, FL 34711]()
2 beds
|2 baths
|1,374 sq ft
|Villa
3201 SONESTA CT B, CLERMONT, FL, 34711
Community: Heritage Hills
MLS G5093860 • HOMESMART, Kevin Trout
Halifax Plantation
![2967 ARRANMORE DR, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
4 beds
|4 baths
|3,221 sq ft
|House
2967 ARRANMORE DR, ORMOND BEACH, FL, 321...
Community: Halifax Plantation
MLS V4945744 • SIMPLY REAL ESTATE, Geri Westfall ...
Arlington Ridge
![4415 ANTIETAM CREEK TRL, LEESBURG, FL, 3..., Leesburg, FL 34748]()
2 beds
|2 baths
|2,076 sq ft
|House
4415 ANTIETAM CREEK TRL, LEESBURG, FL, 3...
Community: Arlington Ridge
MLS G5103918 • CENTURY 21 ALTON CLARK, Kathi Hill
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Arlington Ridge
![26812 AUGUSTA SPRINGS CIR, LEESBURG, FL,..., Leesburg, FL 34748]()
4 beds
|3 baths
|2,318 sq ft
|House
26812 AUGUSTA SPRINGS CIR, LEESBURG, FL,...
Community: Arlington Ridge
MLS G5103238 • WATSON REALTY CORP, Nancy McCloske...
Arlington Ridge
![26712 AUGUSTA SPRINGS CIR, LEESBURG, FL,..., Leesburg, FL 34748]()
2 beds
|2 baths
|2,211 sq ft
|House
26712 AUGUSTA SPRINGS CIR, LEESBURG, FL,...
Community: Arlington Ridge
MLS G5101848 • CARLINO REAL ESTATE GROUP INC, Dia...
Del Webb Sunbridge
![2743 RIVER CREEK LN, SAINT CLOUD, FL, 34..., Saint Cloud, FL 34771]()
4 beds
|3 baths
|2,321 sq ft
|House
2743 RIVER CREEK LN, SAINT CLOUD, FL, 34...
Community: Del Webb Sunbridge
MLS O6331310 • PREMIER SOTHEBYS INT'L REALTY, Sea...
Royal Highlands
![20751 QUEEN ALEXANDRA DR, LEESBURG, FL, ..., Leesburg, FL 34748]()
3 beds
|3 baths
|2,224 sq ft
|House
20751 QUEEN ALEXANDRA DR, LEESBURG, FL, ...
Community: Royal Highlands
MLS G5094138 • VANGIE BERRY SIGNATURE REALTY, Ang...
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 Sunbridge
![6145 CITRUS GROVE CT, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34771]()
2 beds
|2 baths
|2,077 sq ft
|House
6145 CITRUS GROVE CT, SAINT CLOUD, FL, 3...
Community: Del Webb Sunbridge
MLS O6270889 • KELLER WILLIAMS REALTY AT THE PARK...
The Villages®
![2469 ELDON PL, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
2469 ELDON PL, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5104709 • WORTH CLARK REALTY, Mary Hart
Twin Lakes
![2632 MEADOWEDGE LOOP, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772]()
3 beds
|3 baths
|2,335 sq ft
|House
2632 MEADOWEDGE LOOP, SAINT CLOUD, FL, 3...
Community: Twin Lakes
MLS O6355744 • METROPOLIS R.E. SOLUTIONS, LLC, Me...
The Villages®
![17339 SE 84TH FOXGROVE AVE, THE VILLAGES..., The Villages, FL 32162]()
3 beds
|3 baths
|3,693 sq ft
|Villa
17339 SE 84TH FOXGROVE AVE, THE VILLAGES...
Community: The Villages®
MLS OM711816 • KELLER WILLIAMS CORNERSTONE RE, Ci...
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...
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Latitude Margaritaville
![553 HANG LOOSE WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124]()
3 beds
|3 baths
|2,161 sq ft
|House
553 HANG LOOSE WAY, DAYTONA BEACH, FL, 3...
Community: Latitude Margaritaville
MLS FC312280 • REALTY EXCHANGE, LLC, Daniel Shapk...
The Villages®
![6052 CHASE CT, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
2 beds
|2 baths
|1,227 sq ft
|Villa
6052 CHASE CT, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5102957 • REALTY EXECUTIVES IN THE VILLAGES,...
Kings Ridge
![4051 CAPLAND AVE, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS G5103770 • BILL WEBB REAL ESTATE & INVEST, Wi...
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 ...
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.
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,...
Pelican Bay Daytona Beach
![257 GULL DR, DAYTONA BEACH, FL, 32119, Daytona Beach, FL 32119]()
2 beds
|2 baths
|1,900 sq ft
|House
257 GULL DR, DAYTONA BEACH, FL, 32119
Community: Pelican Bay Daytona Beach
MLS V4945791 • ADAMS, CAMERON & CO., REALTORS, Do...
Summit Greens
![748 SUMMIT GREENS BLVD, CLERMONT, FL, 34..., Clermont, FL 34711]()
3 beds
|2 baths
|1,777 sq ft
|House
748 SUMMIT GREENS BLVD, CLERMONT, FL, 34...
Community: Summit Greens
MLS O6347850 • ERA GRIZZARD REAL ESTATE, Enoch Ca...
The Villages®
![428 TARRSON BLVD, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
3 beds
|2 baths
|1,392 sq ft
|House
428 TARRSON BLVD, LADY LAKE, FL, 32159
Community: The Villages®
MLS O6305404 • SUSAN CRAIG, Jen Hill
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Pelican Bay Daytona Beach
![104 SHEARWATER WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32119]()
3 beds
|3 baths
|2,107 sq ft
|Villa
104 SHEARWATER WAY, DAYTONA BEACH, FL, 3...
Community: Pelican Bay Daytona Beach
MLS V4945823 • ALLPHASE REALTY, Stephanie Bowie
Vienna Square
![1584 VIENNA SQUARE DR, WINTER HAVEN, FL,..., Winter Haven, FL 33884]()
2 beds
|2 baths
|1,231 sq ft
|Villa
1584 VIENNA SQUARE DR, WINTER HAVEN, FL,...
Community: Vienna Square
MLS L4955737 • BHHS FLORIDA PROPERTIES GROUP, Joh...
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2,377
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REIN updates its listings on a daily basis. Data last updated: Jan 11, 2026.
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