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Winter Park, FL 55+ active adult communities & homes for sale - Page 4
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
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
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:
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$100ks
- $200ks
Foxwood Lake Estates, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1982 - 1987
|
545 homes
New
The Villages®
![707 CORTEZ AVE, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
3 beds
|2 baths
|1,690 sq ft
|House
707 CORTEZ AVE, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5109433 • CHARLES RUTENBERG REALTY ORLANDO, ...
New
Plantation at Leesburg
![25312 GREEN HERON DR, LEESBURG, FL, 3474..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,289 sq ft
|House
25312 GREEN HERON DR, LEESBURG, FL, 3474...
Community: Plantation at Leesburg
MLS G5109120 • FLORIDA PLUS REALTY, LLC, Shelby M...
New
Lakes at Laurel Highlands
![1849 PRISTINE LOOP, LAKELAND, FL, 33811, Lakeland, FL 33811]()
3 beds
|2 baths
|1,711 sq ft
|House
1849 PRISTINE LOOP, LAKELAND, FL, 33811
Community: Lakes at Laurel Highlands
MLS O6396279 • RE/MAX ASSURED, William Grim
New
The Villages®
![1685 CAMPOS DR, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,121 sq ft
|Villa
1685 CAMPOS DR, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5109610 • REALTY EXECUTIVES IN THE VILLAGES,...
New
The Villages®
![6316 DANIELSON LOOP, THE VILLAGES, FL, 3..., The Villages, FL 32163]()
3 beds
|2 baths
|1,392 sq ft
|House
6316 DANIELSON LOOP, THE VILLAGES, FL, 3...
Community: The Villages®
MLS OM722002 • SALLY LOVE REAL ESTATE, Star Amado...
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New
Lake Ashton
![4152 DUNMORE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859]()
3 beds
|2 baths
|2,255 sq ft
|House
4152 DUNMORE DR, LAKE WALES, FL, 33859
Community: Lake Ashton
MLS TB8482921 • CHARLES RUTENBERG REALTY INC, Ami...
New
Spruce Creek Country Club
![14023 SE 86TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,910 sq ft
|House
14023 SE 86TH CIR, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS OM721990 • RE/MAX FOXFIRE - SUMMERFIELD, Eile...
New
Plantation at Leesburg
![5036 SAWGRASS LAKE CIR, LEESBURG, FL, 34..., Leesburg, FL 34748]()
3 beds
|3 baths
|2,439 sq ft
|House
5036 SAWGRASS LAKE CIR, LEESBURG, FL, 34...
Community: Plantation at Leesburg
MLS O6395800 • TEAMCONNECT REALTY LLC, Robert Sch...
New
The Villages®
![2247 SHANEWOOD CT, THE VILLAGES, FL, 321..., The Villages, FL 32162]()
3 beds
|2 baths
|1,656 sq ft
|Villa
2247 SHANEWOOD CT, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5110513 • COMPASS FLORIDA LLC, Michele Hart
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.
New
The Villages®
![287 MERCER WAY, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
287 MERCER WAY, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5110430 • JACOBS PREMIER PROPERTIES, Daniel ...
New
The Villages®
![408 DUARTE LN, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,102 sq ft
|Villa
408 DUARTE LN, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5110480 • CENTURY 21 ALTON CLARK, Steven San...
New
The Villages®
![1245 JONESVILLE TER, THE VILLAGES, FL, 3..., The Villages, FL 32162]()
2 beds
|2 baths
|1,156 sq ft
|Villa
1245 JONESVILLE TER, THE VILLAGES, FL, 3...
Community: The Villages®
MLS G5110471 • HOAD REALTY GROUP LLC, Lisa Hoad
New
Heritage Hills
![3859 SANIBEL ST, CLERMONT, FL, 34711, Clermont, FL 34711]()
3 beds
|3 baths
|2,554 sq ft
|House
3859 SANIBEL ST, CLERMONT, FL, 34711
Community: Heritage Hills
MLS O6391833 • BHHS FLORIDA REALTY, Patti Kincaid
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New
The Villages®
![913 BEECHWOOD AVE, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|1 baths
|672 sq ft
|Manufactured Home
913 BEECHWOOD AVE, LADY LAKE, FL, 32159
Community: The Villages®
MLS G5110545 • CHARLES RUTENBERG REALTY ORLANDO, ...
New
Latitude Margaritaville
![331 COOL WATERS WAY, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,308 sq ft
|House
331 COOL WATERS WAY, DAYTONA BEACH, FL, ...
Community: Latitude Margaritaville
MLS NS1087846 • RE/MAX SIGNATURE, Kimberly Sbordo...
New
Royal Harbor
![6071 SAILBOAT AVE, TAVARES, FL, 32778, Tavares, FL 32778]()
3 beds
|2 baths
|1,690 sq ft
|House
6071 SAILBOAT AVE, TAVARES, FL, 32778
Community: Royal Harbor
MLS G5110536 • BHHS FLORIDA REALTY, Catherine Lan...
New
Heritage Hills
![3752 QUAINT LN, CLERMONT, FL, 34711, Clermont, FL 34711]()
3 beds
|3 baths
|2,006 sq ft
|House
3752 QUAINT LN, CLERMONT, FL, 34711
Community: Heritage Hills
MLS G5110537 • COLDWELL BANKER HUBBARD HANSEN, Ri...
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.
New
Pelican Bay Daytona Beach
![537 BROWN PELICAN DR, DAYTONA BEACH, FL,..., Daytona Beach, FL 32119]()
3 beds
|2 baths
|1,484 sq ft
|Townhouse
537 BROWN PELICAN DR, DAYTONA BEACH, FL,...
Community: Pelican Bay Daytona Beach
MLS V4948315 • RE/MAX ADVANTAGE, Eric Zimmerman
New
The Villages®
![1097 HOLLYHOCK WAY, THE VILLAGES, FL, 32..., The Villages, FL 32163]()
3 beds
|2 baths
|1,561 sq ft
|House
1097 HOLLYHOCK WAY, THE VILLAGES, FL, 32...
Community: The Villages®
MLS A4688743 • FLATFEE.COM, Cliff Glansen
New
The Villages®
![514 S TIMBER TRL, WILDWOOD, FL, 34785, Wildwood, FL 34785]()
2 beds
|2 baths
|1,352 sq ft
|Manufactured Home
514 S TIMBER TRL, WILDWOOD, FL, 34785
Community: The Villages®
MLS G5110532 • MARK BECKER REALTY LLC, Mark Becke...
New
Arlington Ridge
![26601 BULL RUN, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,913 sq ft
|House
26601 BULL RUN, LEESBURG, FL, 34748
Community: Arlington Ridge
MLS O6396041 • MIGHTY REALTY INC, JoAnn Bonilla
Want to learn more about 55+ communities in Winter Park?
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(888) 625-4885
New
The Villages®
![5495 HAWKINS DR, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|2,061 sq ft
|House
5495 HAWKINS DR, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5110525 • DOWN HOME REALTY, LLLP, Amber Byrn...
New
The Villages®
![2427 TAMARIND GROVE RUN, THE VILLAGES, F..., The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
2427 TAMARIND GROVE RUN, THE VILLAGES, F...
Community: The Villages®
MLS G5110493 • REALTY EXECUTIVES IN THE VILLAGES,...
New
The Villages®
![720 SAN MARINO DR, THE VILLAGES, FL, 321..., The Villages, FL 32159]()
2 beds
|2 baths
|1,613 sq ft
|House
720 SAN MARINO DR, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5110492 • COLDWELL BANKER REALTY, William Pe...
New
The Villages®
![1410 ALMANZA DR, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,174 sq ft
|Villa
1410 ALMANZA DR, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5110428 • RE/MAX PREMIER REALTY, Guy William...
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.
New
The Villages®
![17040 SE 96TH CHAPELWOOD CIR, THE VILLAG..., The Villages, FL 32162]()
3 beds
|2 baths
|1,265 sq ft
|House
17040 SE 96TH CHAPELWOOD CIR, THE VILLAG...
Community: The Villages®
MLS G5110423 • REALTY EXECUTIVES IN THE VILLAGES,...
New
Lake Ashton
![4193 STONE CREEK LOOP, LAKE WALES, FL, 3..., Lake Wales, FL 33859]()
3 beds
|2 baths
|2,058 sq ft
|House
4193 STONE CREEK LOOP, LAKE WALES, FL, 3...
Community: Lake Ashton
MLS P4938293 • CENTURY 21 WATSON & MYERS REALTY, ...
New
Halifax Plantation
![2824 MONAGHAN DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,361 sq ft
|House
2824 MONAGHAN DR, ORMOND BEACH, FL, 3217...
Community: Halifax Plantation
MLS FC317382 • FLORIDA HOMES REALTY & MORTGAGE, A...
New
Halifax Plantation
![3003 GLIN CIR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,684 sq ft
|Villa
3003 GLIN CIR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
MLS FC317337 • TRADEMARK REALTY GROUP LLC, Marie ...
New
The Villages®
![1232 ZAPATA PL, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|1,040 sq ft
|House
1232 ZAPATA PL, LADY LAKE, FL, 32159
Community: The Villages®
MLS G5109848 • RIGHT REALTY CONNECTION, INC., Geo...
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(888) 625-4885
New
Latitude Margaritaville
![234 SUMMERTIME PL, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,778 sq ft
|House
234 SUMMERTIME PL, DAYTONA BEACH, FL, 32...
Community: Latitude Margaritaville
MLS 1224909 • Bob Hodges and Sons Realty, Kelley ...
New
Twin Lakes
![2303 DATURA LOOP, ST CLOUD, FL, 34772, St Cloud, FL 34772]()
2 beds
|2 baths
|1,346 sq ft
|Halfplex
2303 DATURA LOOP, ST CLOUD, FL, 34772
Community: Twin Lakes
MLS O6396116 • COLDWELL BANKER REALTY, Thad Czapk...
New
The Villages®
![1116 W BOONE CT, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|1,144 sq ft
|Modular
1116 W BOONE CT, LADY LAKE, FL, 32159
Community: The Villages®
MLS OM722106 • SOUTHERN ASSOCIATES REALTY LLC, Da...
New
The Lakes at Harmony
![3468 MIDDLEBROOK PL, ST CLOUD, FL, 34773, St Cloud, FL 34773]()
4 beds
|2 baths
|2,064 sq ft
|House
3468 MIDDLEBROOK PL, ST CLOUD, FL, 34773
Community: The Lakes at Harmony
MLS TB8493199 • LA ROSA REALTY, LLC, Olga Tobon
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.
New
Bridgewater at Viera
![1453 GREAT BELT CIR, MELBOURNE, FL, 3294..., Melbourne, FL 32940]()
3 beds
|2 baths
|1,590 sq ft
|House
1453 GREAT BELT CIR, MELBOURNE, FL, 3294...
Community: Bridgewater at Viera
MLS 1073848 • 1 Percent Lists FL's Finest, Karen ...
New
Spruce Creek Country Club
![13126 SE 93RD TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,644 sq ft
|House
13126 SE 93RD TERRACE RD, SUMMERFIELD, F...
Community: Spruce Creek Country Club
MLS OM720596 • JUDY L. TROUT REALTY, Judy Trout
New
Kings Ridge
![2144 ADDISON AVE, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS B26011333 • Illustrated Properties LLC, Jerly...
New
The Villages®
![626 REEVESVILLE LN, THE VILLAGES, FL, 32..., The Villages, FL 32162]()
3 beds
|2 baths
|1,398 sq ft
|Villa
626 REEVESVILLE LN, THE VILLAGES, FL, 32...
Community: The Villages®
MLS OM722006 • SALLY LOVE REAL ESTATE, Star Amado...
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(888) 625-4885
New
Twin Lakes
![5017 E FOUNTAINWOOD DR, ST CLOUD, FL, 34..., St Cloud, FL 34772]()
3 beds
|2 baths
|1,863 sq ft
|House
5017 E FOUNTAINWOOD DR, ST CLOUD, FL, 34...
Community: Twin Lakes
MLS O6395461 • EXP REALTY LLC, Brittany Pride
New
Solivita
![967 LADERA RANCH RD, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759]()
4 beds
|3 baths
|2,465 sq ft
|House
967 LADERA RANCH RD, KISSIMMEE, FL, 3475...
Community: Solivita
MLS O6395722 • STRONG FOUNDATION REALTY LLC, Harr...
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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.
