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Winter Park, FL 55+ active adult communities & homes for sale - Page 56
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
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]()
$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
Traditions at Lake Ruby
![3365 RALEIGH DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884]()
2 beds
|2 baths
|1,295 sq ft
|House
3365 RALEIGH DR, WINTER HAVEN, FL, 33884
Community: Traditions at Lake Ruby
MLS P4936886 • EXP REALTY LLC, James Barris
Solivita
![543 VIA VITALE CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5137772 • BORCHINI REALTY, Edie Stauffer
Indian River Colony Club
![1453 PATRIOT DR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
4 beds
|2 baths
|2,293 sq ft
|House
1453 PATRIOT DR, MELBOURNE, FL, 32940
Community: Indian River Colony Club
MLS 1024799 • Four Star Real Estate LLC, Shellie ...
Solivita
![525 GENOA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5131724 • FAIRWAY REALTY OF SOLIVITA, Bonnie...
Solivita
![128 RIALTO RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5132072 • PELLEGO, LLC, Paul Maiatico
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The Villages®
![1125 MAYNARD PATH, THE VILLAGES, FL, 321..., The Villages, FL 32163]()
4 beds
|3 baths
|2,296 sq ft
|House
1125 MAYNARD PATH, THE VILLAGES, FL, 321...
Community: The Villages®
MLS OM709711 • RE/MAX ALLSTARS REALTY, Amber D'An...
Lake James
![7911 LAKE JAMES BLVD, LAKELAND, FL, 3381..., Lakeland, FL 33810]()
3 beds
|2 baths
|1,886 sq ft
|House
7911 LAKE JAMES BLVD, LAKELAND, FL, 3381...
Community: Lake James
MLS L4955716 • CLARK REALTY LLC, Steven Perkins
Lake James
![8107 LAKE JAMES BLVD, LAKELAND, FL, 3381..., Lakeland, FL 33810]()
2 beds
|2 baths
|1,557 sq ft
|House
8107 LAKE JAMES BLVD, LAKELAND, FL, 3381...
Community: Lake James
MLS L4955333 • EXP REALTY LLC, Rusty Shinault
Lake James
![7895 LAKE JAMES BLVD, LAKELAND, FL, 3381..., Lakeland, FL 33810]()
3 beds
|2 baths
|1,886 sq ft
|House
7895 LAKE JAMES BLVD, LAKELAND, FL, 3381...
Community: Lake James
MLS L4954926 • COLDWELL BANKER REALTY, Nicole Alv...
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®
![1387 ZEST AVE, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
2 beds
|2 baths
|1,156 sq ft
|Villa
1387 ZEST AVE, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5102183 • LPT REALTY, LLC, Makayla Neighbors
High Vista at Ridgewood Lakes
![53 HIGH VISTA DR, DAVENPORT, FL, 33837, Davenport, FL 33837]()
3 beds
|2 baths
|1,856 sq ft
|House
53 HIGH VISTA DR, DAVENPORT, FL, 33837
Community: High Vista at Ridgewood Lakes
MLS O6280714 • SERHANT, Jonathan Fadoul
Spruce Creek South
![10465 SE 179TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,143 sq ft
|House
10465 SE 179TH ST, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
MLS OM712806 • JUDY L. TROUT REALTY, Judy Trout
Huntington at Hunter's Ridge
![14 FAWN HAVEN TRL, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|2,001 sq ft
|House
14 FAWN HAVEN TRL, ORMOND BEACH, FL, 321...
Community: Huntington at Hunter's Ridge
MLS FC313822 • DEUCES REALTY LLC, Mark Polakovich
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Solivita
![525 SHOREHAVEN DR, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5134633 • BORCHINI REALTY, Dale Pautz
Solivita
![156 GRAND CANAL DR, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5120111 • HOMETRUST REALTY GROUP, Joseph San...
Spruce Creek Country Club
![8649 SE 141ST PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
2 beds
|2 baths
|1,356 sq ft
|Villa
8649 SE 141ST PL, SUMMERFIELD, FL, 34491
Community: Spruce Creek Country Club
MLS OM708357 • REALTY ONE GROUP DAVALLS, David St...
Scottish Highlands
![610 FANNICH CT, LEESBURG, FL, 34788, Leesburg, FL 34788]()
2 beds
|2 baths
|1,182 sq ft
|House
610 FANNICH CT, LEESBURG, FL, 34788
Community: Scottish Highlands
MLS G5102200 • ERA GRIZZARD REAL ESTATE, Cynthia ...
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
![46 LONGRIDGE LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
2 beds
|2 baths
|1,529 sq ft
|Townhouse
46 LONGRIDGE LN, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS 1217630 • Venture Development Realty, Inc, Co...
Stonecrest
![17083 SE 115TH TERRACE RD, SUMMERFIELD, ..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,782 sq ft
|House
17083 SE 115TH TERRACE RD, SUMMERFIELD, ...
Community: Stonecrest
MLS OM707914 • DALTON WADE INC, Tammy Luce
The Timbers at Everlands
![853 ANTIBES CT NW, PALM BAY, FL, 32907, Palm Bay, FL 32907]()
3 beds
|3 baths
|2,182 sq ft
|House
853 ANTIBES CT NW, PALM BAY, FL, 32907
Community: The Timbers at Everlands
MLS 1051806 • Blue Marlin Real Estate, Jason Bist...
The Timbers at Everlands
![2223 ANTARUS DR NW, PALM BAY, FL, 32907, Palm Bay, FL 32907]()
3 beds
|4 baths
|1,710 sq ft
|House
2223 ANTARUS DR NW, PALM BAY, FL, 32907
Community: The Timbers at Everlands
MLS 1051805 • Blue Marlin Real Estate, Jason Bist...
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Foxwood Lake Estates
![1576 LONGBOW DR, LAKELAND, FL, 33810, Lakeland, FL 33810]()
3 beds
|2 baths
|1,152 sq ft
|Manufactured Home
1576 LONGBOW DR, LAKELAND, FL, 33810
Community: Foxwood Lake Estates
MLS TB8421306 • VINTAGE REAL ESTATE SERVICES, Bec...
Spruce Creek South
![17733 SE 95TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,390 sq ft
|House
17733 SE 95TH CIR, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
MLS G5102084 • CHARLES RUTENBERG REALTY ORLANDO, ...
Silver Lakes
![6118 SILVER LAKES DR, LAKELAND, FL, 3381..., Lakeland, FL 33810]()
3 beds
|2 baths
|1,510 sq ft
|House
6118 SILVER LAKES DR, LAKELAND, FL, 3381...
Community: Silver Lakes
MLS L4944800 • PREMIER HOMES AND REAL ESTATE, Chr...
Colonnades
![4965 GOLDENVIEW LN, LAKELAND, FL, 33811, Lakeland, FL 33811]()
2 beds
|2 baths
|1,350 sq ft
|House
4965 GOLDENVIEW LN, LAKELAND, FL, 33811
Community: Colonnades
MLS L4952142 • COLDWELL BANKER REALTY, Lisa Broch...
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 Orlando
![208 DEL SOL AVE, DAVENPORT, FL, 33837, Davenport, FL 33837]()
4 beds
|2 baths
|2,249 sq ft
|House
208 DEL SOL AVE, DAVENPORT, FL, 33837
Community: Del Webb Orlando
MLS O6346799 • A+ REALTY PROFESSIONALS, INC, Susa...
Lake Ashton
![3829 LITCHFIELD LOOP, LAKE WALES, FL, 33..., Lake Wales, FL 33859]()
2 beds
|2 baths
|1,763 sq ft
|House
3829 LITCHFIELD LOOP, LAKE WALES, FL, 33...
Community: Lake Ashton
MLS P4936618 • LAKE ASHTON REALTY INC., Lori Raat...
Royal Highlands
![5124 LINKS LN, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,759 sq ft
|House
5124 LINKS LN, LEESBURG, FL, 34748
Community: Royal Highlands
MLS G5103861 • FLORIDA PLUS REALTY, LLC, Claire B...
The Villages®
![2167 KERWOOD LOOP, THE VILLAGES, FL, 321..., The Villages, FL 32162]()
3 beds
|2 baths
|1,467 sq ft
|Villa
2167 KERWOOD LOOP, THE VILLAGES, FL, 321...
Community: The Villages®
MLS O6355925 • COLDWELL BANKER RESIDENTIAL RE, Ro...
Plantation at Leesburg
![25527 OAK ALY, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,518 sq ft
|House
25527 OAK ALY, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5093909 • CARLINO REAL ESTATE GROUP INC, Mar...
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Latitude Margaritaville
![568 HIGH TIDE LN, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,308 sq ft
|Townhouse
568 HIGH TIDE LN, DAYTONA BEACH, FL, 321...
Community: Latitude Margaritaville
MLS 1219496 • Beycome of Florida LLC, Steven Kole...
Twin Lakes
![4921 CATALPA DR, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772]()
3 beds
|3 baths
|2,365 sq ft
|House
4921 CATALPA DR, SAINT CLOUD, FL, 34772
Community: Twin Lakes
MLS S5137679 • WEICHERT REALTORS HALLMARK PRO, Sh...
Kings Ridge
![3667 KINGSWOOD CT, CLERMONT, FL, 34711, Clermont, FL 34711]()
2 beds
|2 baths
|1,552 sq ft
|House
3667 KINGSWOOD CT, CLERMONT, FL, 34711
Community: Kings Ridge
MLS O6275507 • FLORIDA PRESTIGIOUS HOMES INC, Ian...
The Villages®
![867 CASTLEBERRY CIR, THE VILLAGES, FL, 3..., The Villages, FL 32162]()
3 beds
|2 baths
|1,993 sq ft
|House
867 CASTLEBERRY CIR, THE VILLAGES, FL, 3...
Community: The Villages®
MLS OM697819 • EXP REALTY LLC, Garrett Huffman
Download the Ultimate 55+ Homebuying Guide
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Plantation at Leesburg
![25749 WHISPER OAKS RD, LEESBURG, FL, 347..., Leesburg, FL 34748]()
3 beds
|2 baths
|1,967 sq ft
|House
25749 WHISPER OAKS RD, LEESBURG, FL, 347...
Community: Plantation at Leesburg
MLS G5103779 • CENTURY 21 MYERS REALTY, Mary Jane...
Halifax Plantation
![3026 ADRIAN DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|3 baths
|2,232 sq ft
|House
3026 ADRIAN DR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
MLS FC312375 • LPT REALTY LLC (PALM COAST), Danie...
Lake James
![7898 LAKE JAMES BLVD, LAKELAND, FL, 3381..., Lakeland, FL 33810]()
2 beds
|2 baths
|1,911 sq ft
|House
7898 LAKE JAMES BLVD, LAKELAND, FL, 3381...
Community: Lake James
MLS L4956979 • THE MARKET REALTY COMPANY, Brock J...
Latitude Margaritaville
![244 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,466 sq ft
|House
244 GYPSY PALACE LN, DAYTONA BEACH, FL, ...
Community: Latitude Margaritaville
MLS V4945665 • RE/MAX SIGNATURE, Kathie Craig
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Plantation at Leesburg
![26234 GLEN EAGLE DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,761 sq ft
|House
26234 GLEN EAGLE DR, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5103920 • OLYMPUS EXECUTIVE REALTY INC, Caro...
Spruce Creek South
![10339 SE 179TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,008 sq ft
|House
10339 SE 179TH ST, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
MLS TB8442771 • KELLER WILLIAMS SUBURBAN TAMPA, T...
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2,377
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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.
