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Winter Park, FL 55+ active adult communities & homes for sale - Page 24
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
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
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)
![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]()
$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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1 rating (1 reviews)
![Sullivan Ranch]()
$200Ks
- $700Ks
Sullivan Ranch, Mount Dora, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2020
|
692 homes
Spruce Creek South
![9509 SE 173RD LN, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
2 beds
|2 baths
|1,248 sq ft
|House
9509 SE 173RD LN, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
MLS OM713553 • JUDY L. TROUT REALTY, Kevin Boutwe...
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
Pennbrooke Fairways
![751 OLD OAKS LN, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,753 sq ft
|House
751 OLD OAKS LN, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS G5097637 • CHARLES RUTENBERG REALTY ORLANDO, ...
Solivita
![1192 VIA GALUPPI ST, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759]()
3 beds
|2 baths
|1,723 sq ft
|House
1192 VIA GALUPPI ST, KISSIMMEE, FL, 3475...
Community: Solivita
MLS G5105188 • EXP REALTY LLC, Edalys Ramos
Indian River Colony Club
![1505 CHESAPEAKE CT, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|2 baths
|1,885 sq ft
|House
1505 CHESAPEAKE CT, MELBOURNE, FL, 32940
Community: Indian River Colony Club
MLS 1053171 • Four Star Real Estate LLC, Shellie ...
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Heritage Isle
![6858 TOLAND DR APT 304, MELBOURNE, FL, 3..., Melbourne, FL 32940]()
2 beds
|2 baths
|1,194 sq ft
|Condo
6858 TOLAND DR APT 304, MELBOURNE, FL, 3...
Community: Heritage Isle
MLS 1046244 • Carnu Realty LLC, Carolyn M Schuman...
Del Webb Orlando
![519 CADIZ DR, DAVENPORT, FL, 33837, Davenport, FL 33837]()
2 beds
|2 baths
|1,358 sq ft
|House
519 CADIZ DR, DAVENPORT, FL, 33837
Community: Del Webb Orlando
MLS O6356547 • GOYAL & DECOSTER REALTY, Freddy De...
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...
Royal Highlands
![5007 KELSO ST, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,469 sq ft
|House
5007 KELSO ST, LEESBURG, FL, 34748
Community: Royal Highlands
MLS OM702826 • MEADOWS REALTY, LLC, Pamela Cook
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®
![704 BOLIVAR ST, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,248 sq ft
|House
704 BOLIVAR ST, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5099980 • BEACON REAL ESTATE & ASSOC, Sandra...
Plantation at Leesburg
![4745 TARA VIEW RD, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,988 sq ft
|House
4745 TARA VIEW RD, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5101070 • CENTURY 21 MYERS REALTY, Mary Jane...
Del Webb Sunbridge
![2445 CLIFF WAY, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771]()
2 beds
|2 baths
|1,401 sq ft
|House
2445 CLIFF WAY, SAINT CLOUD, FL, 34771
Community: Del Webb Sunbridge
MLS O6366682 • CHARLES RUTENBERG REALTY ORLANDO, ...
Solivita
![1062 UMBRIA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS O6336786 • FLORIDA PLUS REALTY, LLC, Sarah Bo...
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Stonecrest
![12103 SE 176TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,822 sq ft
|House
12103 SE 176TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
MLS G5102417 • RE/MAX FOXFIRE - LADY LAKE, Mika G...
Solivita
![274 MARABELLA LOOP, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS O6357948 • KELLER WILLIAMS CLASSIC, Barbara L...
The Villages®
![2737 AVA ST, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|1,630 sq ft
|House
2737 AVA ST, THE VILLAGES, FL, 32163
Community: The Villages®
MLS C7518762 • DALTON WADE INC, Mandy Wells
The Lakes at Harmony
![3443 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773]()
2 beds
|2 baths
|1,637 sq ft
|House
3443 SAGEBRUSH ST, HARMONY, FL, 34773
Community: The Lakes at Harmony
MLS O6323985 • RESORT REALTY GROUP LTD INC, David...
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.
Four Seasons at Orlando
![7957 HANSON BAY PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747]()
3 beds
|2 baths
|2,271 sq ft
|House
7957 HANSON BAY PL, KISSIMMEE, FL, 34747
Community: Four Seasons at Orlando
MLS S5124926 • OLDE KISSIMMEE REALTY, Kelly Yerke...
Twin Lakes
![5150 GARDENROW DR, SAINT CLOUD, FL, 3477..., Saint Cloud, FL 34772]()
2 beds
|2 baths
|1,322 sq ft
|Villa
5150 GARDENROW DR, SAINT CLOUD, FL, 3477...
Community: Twin Lakes
MLS O6364860 • PULTE REALTY OF NORTH FLORIDA LLC,...
Twin Lakes
![2781 BUCKEYE LN, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772]()
2 beds
|2 baths
|1,322 sq ft
|Villa
2781 BUCKEYE LN, SAINT CLOUD, FL, 34772
Community: Twin Lakes
MLS O6364463 • PULTE REALTY OF NORTH FLORIDA LLC,...
Grand Haven
![15 CHINIER ST, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
MLS FC314149 • COASTAL GATEWAY REAL ESTATE GR, Lu...
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Grand Haven
![2 GLENEAGLES PL, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
3 beds
|2 baths
|1,785 sq ft
|House
2 GLENEAGLES PL, PALM COAST, FL, 32137
Community: Grand Haven
MLS FC314103 • RE/MAX SELECT PROFESSIONALS, Cryst...
The Villages®
![2517 PRIVADA DR, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,527 sq ft
|House
2517 PRIVADA DR, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5103249 • BROKER ASSOCIATES REALTY, David Ze...
The Villages®
![3161 DRESSENDORFER DR, THE VILLAGES, FL,..., The Villages, FL 32163]()
3 beds
|2 baths
|1,907 sq ft
|House
3161 DRESSENDORFER DR, THE VILLAGES, FL,...
Community: The Villages®
MLS O6342022 • DOUGLAS ELLIMAN, Orlando Sanchez
Del Webb Sunbridge
![3122 VANGUARD CT, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771]()
5 beds
|4 baths
|3,460 sq ft
|House
3122 VANGUARD CT, SAINT CLOUD, FL, 34771
Community: Del Webb Sunbridge
MLS O6351489 • ORLANDO PROPERTY ADVISORS, Justin ...
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.
Plantation at Leesburg
![5300 TIGERS TAIL, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,144 sq ft
|Manufactured Home
5300 TIGERS TAIL, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5096957 • CENTURY 21 MYERS REALTY, Dawn Broo...
The Timbers at Everlands
![2406 CERULEAN DR NW, PALM BAY, FL, 32907, Palm Bay, FL 32907]()
3 beds
|2 baths
|1,758 sq ft
|House
2406 CERULEAN DR NW, PALM BAY, FL, 32907
Community: The Timbers at Everlands
MLS 1057098 • Ellingson Properties, Gregory Ellin...
Plantation Bay Golf & Country Club
![51 BAY POINTE DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,996 sq ft
|House
51 BAY POINTE DR, ORMOND BEACH, FL, 3217...
Community: Plantation Bay Golf & Country Club
MLS 1209215 • Realty Evolution Inc, Marsha Thayer
Stonecrest
![17306 SE 112TH COURT RD, SUMMERFIELD, FL..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,955 sq ft
|House
17306 SE 112TH COURT RD, SUMMERFIELD, FL...
Community: Stonecrest
MLS G5102892 • CHARLES RUTENBERG REALTY ORLANDO, ...
Highland Lakes
![5606 LAVER ST, LEESBURG, FL, 34748, Leesburg, FL 34748]()
MLS G5102950 • FLORIDA PLUS REALTY, LLC, Claire B...
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VillageWalk at Lake Nona
![11794 BARLETTA DR, ORLANDO, FL, 32827, Orlando, FL 32827]()
3 beds
|2 baths
|1,949 sq ft
|House
11794 BARLETTA DR, ORLANDO, FL, 32827
Community: VillageWalk at Lake Nona
MLS S5136454 • EXP REALTY LLC, Cliff Clover
Spruce Creek Country Club
![13235 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491]()
2 beds
|2 baths
|2,149 sq ft
|House
13235 SE 97TH TERRACE RD, SUMMERFIELD, F...
Community: Spruce Creek Country Club
MLS OM713351 • RE/MAX FOXFIRE - SUMMERFIELD, Ed D...
The Villages®
![1175 JOHNSTON PATH, THE VILLAGES, FL, 32..., The Villages, FL 32162]()
3 beds
|2 baths
|2,205 sq ft
|House
1175 JOHNSTON PATH, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5102381 • ERA GRIZZARD REAL ESTATE, Stacy Br...
Plantation Bay Golf & Country Club
![1117 OXBRIDGE LN, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
4 beds
|5 baths
|5,352 sq ft
|House
1117 OXBRIDGE LN, ORMOND BEACH, FL, 3217...
Community: Plantation Bay Golf & Country Club
MLS V4943822 • WATSON REALTY CORP, Theresa Geyer
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.
Plantation Bay Golf & Country Club
![4 JASMINE RUN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
2 beds
|2 baths
|2,037 sq ft
|House
4 JASMINE RUN, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS FC311404 • ONE SOTHEBYS INTERNATIONAL, Kory L...
Scottish Highlands
![2215 ORKNEY DR, LEESBURG, FL, 34788, Leesburg, FL 34788]()
2 beds
|2 baths
|1,304 sq ft
|Condo
2215 ORKNEY DR, LEESBURG, FL, 34788
Community: Scottish Highlands
MLS G5104796 • BLU SEA DREAMS,LLC, Elizabeth Fox
Foxwood Lake Estates
![4910 LOCH NESS DR, LAKELAND, FL, 33810, Lakeland, FL 33810]()
2 beds
|2 baths
|1,404 sq ft
|Manufactured Home
4910 LOCH NESS DR, LAKELAND, FL, 33810
Community: Foxwood Lake Estates
MLS L4957893 • DALTON WADE INC, Carolyn Christian
Twin Lakes
![2699 MIDSWEET AVE, SAINT CLOUD, FL, 3477..., Saint Cloud, FL 34772]()
3 beds
|3 baths
|2,365 sq ft
|House
2699 MIDSWEET AVE, SAINT CLOUD, FL, 3477...
Community: Twin Lakes
MLS O6341153 • FLORIDA INT'NL REAL ESTATE LLC, Li...
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Latitude Margaritaville
![899 MARGARITAVILLE AVE, DAYTONA BEACH, F..., Daytona Beach, FL 32124]()
3 beds
|2 baths
|1,771 sq ft
|House
899 MARGARITAVILLE AVE, DAYTONA BEACH, F...
Community: Latitude Margaritaville
MLS 1220854 • Realty Pros Assured, Shannon Brooks
Spruce Creek South
![17356 SE 98TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,678 sq ft
|House
17356 SE 98TH CIR, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
MLS G5102778 • FLORIDA FINE HOMES REALTY, LLC, De...
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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.
