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Winter Park, FL 55+ active adult communities & homes for sale - Page 21
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
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$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
Plantation at Leesburg
![25339 CRESTWATER DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,765 sq ft
|House
25339 CRESTWATER DR, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5096143 • VANGIE BERRY SIGNATURE REALTY, Ang...
Plantation at Leesburg
![25243 RIVER CREST DR, LEESBURG, FL, 3474..., Leesburg, FL 34748]()
3 beds
|3 baths
|2,529 sq ft
|House
25243 RIVER CREST DR, LEESBURG, FL, 3474...
Community: Plantation at Leesburg
MLS G5097211 • FLORIDA PLUS REALTY, LLC, Sandy Tw...
Solivita
![134 GLENDALE CT, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5133349 • BORCHINI REALTY, Charles Borchini
Spruce Creek Country Club
![12896 SE 91ST TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,935 sq ft
|House
12896 SE 91ST TERRACE RD, SUMMERFIELD, F...
Community: Spruce Creek Country Club
MLS OM707637 • RE/MAX PREMIER REALTY LADY LK, Jay...
Spruce Creek Country Club
![13320 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491]()
2 beds
|3 baths
|2,346 sq ft
|House
13320 SE 97TH TERRACE RD, SUMMERFIELD, F...
Community: Spruce Creek Country Club
MLS OM704998 • RE/MAX PREMIER REALTY LADY LK, Jay...
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High Vista at Ridgewood Lakes
![29 HIGH VISTA DR, DAVENPORT, FL, 33837, Davenport, FL 33837]()
3 beds
|2 baths
|1,862 sq ft
|House
29 HIGH VISTA DR, DAVENPORT, FL, 33837
Community: High Vista at Ridgewood Lakes
MLS O6361061 • STAR BAY REALTY CORP., Abraham Bid...
Cypress Lakes
![2352 PEAVINE CIR # 1016, LAKELAND, FL, 3..., Lakeland, FL 33810]()
2 beds
|2 baths
|1,134 sq ft
|Manufactured Home
2352 PEAVINE CIR # 1016, LAKELAND, FL, 3...
Community: Cypress Lakes
MLS TB8445301 • REAL BROKER, LLC, Robert Johnson
Scottish Highlands
![2231 ORKNEY DR, LEESBURG, FL, 34788, Leesburg, FL 34788]()
2 beds
|2 baths
|1,608 sq ft
|House
2231 ORKNEY DR, LEESBURG, FL, 34788
Community: Scottish Highlands
MLS G5105744 • ERA GRIZZARD REAL ESTATE, Cynthia ...
Grand Haven
![14 SANDPIPER CT, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
3 beds
|2 baths
|1,868 sq ft
|House
14 SANDPIPER CT, PALM COAST, FL, 32137
Community: Grand Haven
MLS FC314803 • RE/MAX SELECT PROFESSIONALS, DOUGL...
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.
Scottish Highlands
![1514 NEW ABBEY AVE, LEESBURG, FL, 34788, Leesburg, FL 34788]()
3 beds
|2 baths
|1,600 sq ft
|House
1514 NEW ABBEY AVE, LEESBURG, FL, 34788
Community: Scottish Highlands
MLS G5104143 • HOME WISE REALTY GROUP, INC., Wend...
Kings Ridge
![3577 ROLLINGBROOK ST, CLERMONT, FL, 3471..., Clermont, FL 34711]()
2 beds
|2 baths
|1,460 sq ft
|House
3577 ROLLINGBROOK ST, CLERMONT, FL, 3471...
Community: Kings Ridge
MLS O6342985 • SPANN & ASSOCIATES REAL ESTATE, La...
The Villages®
![8143 SE 175TH COLUMBIA PL, THE VILLAGES,..., The Villages, FL 32162]()
3 beds
|2 baths
|1,231 sq ft
|House
8143 SE 175TH COLUMBIA PL, THE VILLAGES,...
Community: The Villages®
MLS OM713357 • KELLER WILLIAMS CORNERSTONE RE, Cr...
Huntington at Hunter's Ridge
![3 HAWK ROOST CT, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
2 beds
|2 baths
|1,593 sq ft
|House
3 HAWK ROOST CT, ORMOND BEACH, FL, 32174
Community: Huntington at Hunter's Ridge
MLS FC314608 • RE/MAX SIGNATURE, Douglas Gernert
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Highland Fairways
![1958 LONG BOAT DR, LAKELAND, FL, 33810, Lakeland, FL 33810]()
2 beds
|2 baths
|1,657 sq ft
|House
1958 LONG BOAT DR, LAKELAND, FL, 33810
Community: Highland Fairways
MLS L4956784 • REMAX EXPERTS, Lorrie Clark
Harbor Hills Country Club
![5556 GROVE MNR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
3 beds
|2 baths
|1,525 sq ft
|House
5556 GROVE MNR, LADY LAKE, FL, 32159
Community: Harbor Hills Country Club
MLS NS1085920 • PREMIER SOTHEBYS INTL REALTY, Tar...
Spruce Creek Country Club
![9588 SE 124TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,979 sq ft
|House
9588 SE 124TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek Country Club
MLS G5097996 • RE/MAX PREMIER REALTY LADY LK, Rob...
Spruce Creek Country Club
![13111 SE 86TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|2,258 sq ft
|House
13111 SE 86TH CIR, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS OM711544 • RE/MAX FOXFIRE - SUMMERFIELD, Davi...
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®
![17300 SE 91ST LEE AVE, THE VILLAGES, FL,..., The Villages, FL 32162]()
3 beds
|2 baths
|2,520 sq ft
|House
17300 SE 91ST LEE AVE, THE VILLAGES, FL,...
Community: The Villages®
MLS G5105694 • SALLY LOVE REAL ESTATE, Kim Coffer
Del Webb Sunbridge
![6501 CYRILS DR, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771]()
3 beds
|3 baths
|1,738 sq ft
|Townhouse
6501 CYRILS DR, SAINT CLOUD, FL, 34771
Community: Del Webb Sunbridge
MLS S5126893 • THE LANDRUA GROUP REAL ESTATE INC,...
The Villages®
![3818 MIRAGALIA LN, THE VILLAGES, FL, 321..., The Villages, FL 32163]()
2 beds
|2 baths
|1,051 sq ft
|Villa
3818 MIRAGALIA LN, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5102972 • FLORIDA FINE HOMES REALTY, LLC, Ca...
Heritage Landings
![2667 CANYON CREST DR, LAKELAND, FL, 3381..., Lakeland, FL 33811]()
3 beds
|2 baths
|1,710 sq ft
|House
2667 CANYON CREST DR, LAKELAND, FL, 3381...
Community: Heritage Landings
MLS L4957054 • S & D REAL ESTATE SERVICE LLC, Jim...
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The Villages®
![2173 JASPER WAY, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,842 sq ft
|House
2173 JASPER WAY, THE VILLAGES, FL, 32162
Community: The Villages®
MLS TB8456096 • COMMUNITY REALTY ASSOCIATES, Doug...
The Villages®
![1042 AVENIDA SONOMA, LADY LAKE, FL, 3215..., Lady Lake, FL 32159]()
3 beds
|3 baths
|2,271 sq ft
|House
1042 AVENIDA SONOMA, LADY LAKE, FL, 3215...
Community: The Villages®
MLS O6330934 • EXP REALTY LLC, Mark Ramey
Solivita
![1305 LOMBARDI CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS O6350952 • RE/MAX SELECT GROUP, Bridget Daku-...
Twin Lakes
![4909 W FOUNTAINWOOD DR, SAINT CLOUD, FL,..., Saint Cloud, FL 34772]()
3 beds
|3 baths
|2,365 sq ft
|House
4909 W FOUNTAINWOOD DR, SAINT CLOUD, FL,...
Community: Twin Lakes
MLS O6367771 • DIAMOND REAL ESTATE GROUP, George ...
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
![9 IBIS CT S, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
MLS FC313592 • VIRTUAL HOMES REALTY, Alina Pekars...
Baytree
![579 JUNIPER WAY, TAVARES, FL, 32778, Tavares, FL 32778]()
MLS G5105608 • ERA GRIZZARD REAL ESTATE, Jeanne T...
Heritage - The Cottages of Sanders Grove
![28026 CYPRESS SPRINGS LOOP, OKAHUMPKA, F..., Okahumpka, FL 34762]()
4 beds
|2 baths
|1,617 sq ft
|House
28026 CYPRESS SPRINGS LOOP, OKAHUMPKA, F...
Community: Heritage - The Cottages of Sanders Grove
MLS TB8434792 • LPT REALTY, LLC, Ashley Mason
Spruce Creek Country Club
![8789 SE 136TH LN, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
3 beds
|2 baths
|2,029 sq ft
|House
8789 SE 136TH LN, SUMMERFIELD, FL, 34491
Community: Spruce Creek Country Club
MLS G5105202 • RE/MAX PREMIER REALTY LADY LK, Rob...
The Villages®
![16950 SE 80TH BELLAVISTA CIR, THE VILLAG..., The Villages, FL 32162]()
3 beds
|2 baths
|2,687 sq ft
|House
16950 SE 80TH BELLAVISTA CIR, THE VILLAG...
Community: The Villages®
MLS O6318915 • CENTURY 21 CARIOTI, Kristi Matthew
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Spruce Creek Country Club
![12150 SE 91ST TER, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,870 sq ft
|House
12150 SE 91ST TER, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS G5100462 • RE/MAX PREMIER REALTY LADY LK, Rob...
Harbor Hills Country Club
![6200 TOPSAIL RD, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|1,537 sq ft
|Villa
6200 TOPSAIL RD, LADY LAKE, FL, 32159
Community: Harbor Hills Country Club
MLS G5094340 • HARBOR HILLS SALES, INC, Sean Rich
The Villages®
![5180 LEXINGTON CIR, WILDWOOD, FL, 34785, Wildwood, FL 34785]()
3 beds
|2 baths
|1,932 sq ft
|Manufactured Home
5180 LEXINGTON CIR, WILDWOOD, FL, 34785
Community: The Villages®
MLS O6355865 • SAND DOLLAR REALTY GROUP INC, Robe...
Twin Lakes
![2621 REDBLUSH TER, SAINT CLOUD, FL, 3477..., Saint Cloud, FL 34772]()
3 beds
|3 baths
|1,982 sq ft
|House
2621 REDBLUSH TER, SAINT CLOUD, FL, 3477...
Community: Twin Lakes
MLS S5129334 • SOUTHERN GROUNDS REALTY LLC, Madie...
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 at Viera
![9023 NIXIE AVE, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|2 baths
|1,640 sq ft
|House
9023 NIXIE AVE, MELBOURNE, FL, 32940
Community: Del Webb at Viera
MLS 1064627 • EXP Realty, LLC, Jonathan Carroll
VillageWalk at Lake Nona
![11827 JAMES BAY DR, ORLANDO, FL, 32827, Orlando, FL 32827]()
4 beds
|3 baths
|1,810 sq ft
|Townhouse
11827 JAMES BAY DR, ORLANDO, FL, 32827
Community: VillageWalk at Lake Nona
MLS O6368149 • EXP REALTY LLC, Kevin Kendrick
Lakes at Laurel Highlands
![2667 CANYON CREST DR, LAKELAND, FL, 3381..., Lakeland, FL 33811]()
3 beds
|2 baths
|1,710 sq ft
|House
2667 CANYON CREST DR, LAKELAND, FL, 3381...
Community: Lakes at Laurel Highlands
MLS L4957054 • S & D REAL ESTATE SERVICE LLC, Jim...
Harbor Hills Country Club
![39320 HARBOR HILLS BLVD, LADY LAKE, FL, ..., Lady Lake, FL 32159]()
3 beds
|2 baths
|2,120 sq ft
|House
39320 HARBOR HILLS BLVD, LADY LAKE, FL, ...
Community: Harbor Hills Country Club
MLS G5090374 • MORRIS REALTY AND INVESTMENTS, Kim...
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Royal Harbor
![5740 BOUNTY CIR, TAVARES, FL, 32778, Tavares, FL 32778]()
MLS O6367210 • PREMIER SOTHEBYS INT'L REALTY, Dou...
Twin Lakes
![2487 YELLOW BRICK RD, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772]()
2 beds
|2 baths
|1,351 sq ft
|Halfplex
2487 YELLOW BRICK RD, SAINT CLOUD, FL, 3...
Community: Twin Lakes
MLS S5140190 • WEICHERT REALTORS HALLMARK PRO, Sh...
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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.
