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Winter Park, FL 55+ active adult communities & homes for sale
90 communities near Winter Park
2,487 homes near Winter Park
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4 rating (17 reviews)
![The Villages®]()
<$100k
- $1Ms
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
$300Ks
- $1Ms
Grand Haven, Palm Coast, FL
New and Resale
|
Age-targeted
|
Built 1997 - present
|
1,901 homes
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$100Ks
- $500Ks
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
- $300Ks
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
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
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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 (2 reviews)
![Heritage Isle]()
$200Ks
- $500Ks
Heritage Isle, Viera, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2017
|
1,500 homes
5 rating (8 reviews)
![Royal Highlands]()
$200Ks
- $500Ks
Royal Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2006
|
1,500 homes
$300Ks
- $800Ks
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
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)
![Del Webb Sunbridge]()
$300Ks
- $1Ms
Del Webb Sunbridge, St. Cloud, FL
New and Resale
|
55+ age-restricted
|
Built 2019 - present
|
1,300 homes
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
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$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
- $700Ks
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
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
- $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
- $600Ks
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
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
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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
- $600Ks
Lakeside Landings, Oxford, FL
New and Resale
|
Age-targeted
|
Built 2005 - present
|
700 homes
1 rating (1 reviews)
![Sullivan Ranch]()
$300Ks
- $600Ks
Sullivan Ranch, Mount Dora, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2020
|
692 homes
Latitude Margaritaville
![494 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,204 sq ft
|House
494 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...
Community: Latitude Margaritaville
MLS 1219448 • Bob Hodges and Sons Realty, Kelley ...
Latitude Margaritaville
![476 HANG LOOSE WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,684 sq ft
|House
476 HANG LOOSE WAY, DAYTONA BEACH, FL, 3...
Community: Latitude Margaritaville
MLS 1218935 • Bob Hodges and Sons Realty, Kelley ...
Latitude Margaritaville
![235 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124]()
3 beds
|2 baths
|1,558 sq ft
|House
235 CORAL REEF WAY, DAYTONA BEACH, FL, 3...
Community: Latitude Margaritaville
MLS 1219214 • Bob Hodges and Sons Realty, Kelley ...
Latitude Margaritaville
![579 GOOD LIFE WAY, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,466 sq ft
|House
579 GOOD LIFE WAY, DAYTONA BEACH, FL, 32...
Community: Latitude Margaritaville
MLS 1218148 • RE/MAX Signature, Kathleen Craig
Latitude Margaritaville
![170 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,378 sq ft
|House
170 GYPSY PALACE LN, DAYTONA BEACH, FL, ...
Community: Latitude Margaritaville
MLS 1216572 • RE/MAX Signature, Kathleen Craig
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Latitude Margaritaville
![1082 CASTAWAY CT, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,684 sq ft
|House
1082 CASTAWAY CT, DAYTONA BEACH, FL, 321...
Community: Latitude Margaritaville
MLS 1212471 • Keller Williams Realty Florida Part...
Latitude Margaritaville
![944 MARGARITAVILLE AVE, DAYTONA BEACH, F..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,558 sq ft
|House
944 MARGARITAVILLE AVE, DAYTONA BEACH, F...
Community: Latitude Margaritaville
MLS 1218107 • LoKation, Aimee Aballo
Latitude Margaritaville
![512 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,482 sq ft
|House
512 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...
Community: Latitude Margaritaville
MLS 1213084 • LoKation, Aimee Aballo
Halifax Plantation
![3078 SILVERMINES AVE, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,914 sq ft
|House
3078 SILVERMINES AVE, ORMOND BEACH, FL, ...
Community: Halifax Plantation
MLS FC313426 • NEVER 6 PERCENT REALTY INC., Peter...
Arlington Ridge
![26822 BULL RUN, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,599 sq ft
|House
26822 BULL RUN, LEESBURG, FL, 34748
Community: Arlington Ridge
MLS G5097176 • REALTY EXECUTIVES IN THE VILLAGES,...
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.
Solivita
![504 MILLIFIORA LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5132187 • WATSON REALTY CORP., Clarissa Este...
Colonnades
![4823 COLONNADES CIR, LAKELAND, FL, 33811, Lakeland, FL 33811]()
2 beds
|2 baths
|1,196 sq ft
|House
4823 COLONNADES CIR, LAKELAND, FL, 33811
Community: Colonnades
MLS L4956860 • COLDWELL BANKER REALTY, Lisa Broch...
Latitude Margaritaville
![148 SIX STRING DR, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124]()
2 beds
|3 baths
|2,347 sq ft
|House
148 SIX STRING DR, DAYTONA BEACH, FL, 32...
Community: Latitude Margaritaville
MLS 1205904 • Bob Hodges and Sons Realty, Kelley ...
Del Webb Orlando
![210 TOMELLOSO WAY, DAVENPORT, FL, 33837, Davenport, FL 33837]()
3 beds
|3 baths
|2,004 sq ft
|House
210 TOMELLOSO WAY, DAVENPORT, FL, 33837
Community: Del Webb Orlando
MLS O6336002 • KELLER WILLIAMS ADVANTAGE III, Kar...
Twin Lakes
![5017 E FOUNTAINWOOD DR, SAINT CLOUD, FL,..., Saint Cloud, FL 34772]()
3 beds
|2 baths
|1,863 sq ft
|House
5017 E FOUNTAINWOOD DR, SAINT CLOUD, FL,...
Community: Twin Lakes
MLS O6332102 • KELLER WILLIAMS ADVANTAGE 2 REALTY...
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Twin Lakes
![5014 E FOUNTAINWOOD DR, SAINT CLOUD, FL,..., Saint Cloud, FL 34772]()
3 beds
|3 baths
|2,208 sq ft
|House
5014 E FOUNTAINWOOD DR, SAINT CLOUD, FL,...
Community: Twin Lakes
MLS S5118231 • WEICHERT REALTORS HALLMARK PRO, Sh...
Legacy of Leesburg
![27401 PINE STRAW RD, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|2,031 sq ft
|House
27401 PINE STRAW RD, LEESBURG, FL, 34748
Community: Legacy of Leesburg
MLS G5102706 • DOUBLE MM DEVELOPMENT, LLC, Mo McL...
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...
Spruce Creek South
![9948 SE 175TH PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
2 beds
|2 baths
|1,878 sq ft
|House
9948 SE 175TH PL, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
MLS G5094985 • REALTY EXECUTIVES IN THE VILLAGES,...
Esplanade at Highland Ranch
![1339 ZEEK RIDGE ST, CLERMONT, FL, 34715, Clermont, FL 34715]()
3 beds
|3 baths
|2,449 sq ft
|House
1339 ZEEK RIDGE ST, CLERMONT, FL, 34715
Community: Esplanade at Highland Ranch
MLS G5099813 • KELLER WILLIAMS ELITE PARTNERS III...
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®
![3021 BEARD RD, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
2 beds
|2 baths
|1,203 sq ft
|Villa
3021 BEARD RD, THE VILLAGES, FL, 32163
Community: The Villages®
MLS OM702838 • REALTY ONE GROUP EPIC, Michael Mil...
Spruce Creek South
![9499 SE 174TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,678 sq ft
|House
9499 SE 174TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
MLS G5097972 • EXP REALTY LLC, Brenda Bell
Latitude Margaritaville
![206 ST SOMEWHERE DR, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,606 sq ft
|Villa
206 ST SOMEWHERE DR, DAYTONA BEACH, FL, ...
Community: Latitude Margaritaville
MLS FC310356 • REALTY PROS ASSURED, Daniel Robins...
Spruce Creek Country Club
![9033 SE 135TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,726 sq ft
|House
9033 SE 135TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek Country Club
MLS OM712350 • JUDY L. TROUT REALTY, Judy Trout
Highland Lakes
![26126 NEWCOMBE CIR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,890 sq ft
|House
26126 NEWCOMBE CIR, LEESBURG, FL, 34748
Community: Highland Lakes
MLS O6351063 • RE/MAX 200 REALTY, Diane Gerry PA
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Spruce Creek Country Club
![11864 SE 91ST CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|2,270 sq ft
|House
11864 SE 91ST CIR, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS OM710939 • JUDY L. TROUT REALTY, Judy Trout
Cresswind at Victoria Gardens
![1011 CLAYMONT BLVD, DELAND, FL, 32724, Deland, FL 32724]()
3 beds
|2 baths
|1,541 sq ft
|House
1011 CLAYMONT BLVD, DELAND, FL, 32724
Community: Cresswind at Victoria Gardens
MLS O6349661 • BETTER HOMES AND GARDENS REAL ESTA...
The Lakes at Harmony
![3116 OXBOW CT, HARMONY, FL, 34773, Harmony, FL 34773]()
3 beds
|2 baths
|1,924 sq ft
|House
3116 OXBOW CT, HARMONY, FL, 34773
Community: The Lakes at Harmony
MLS O6325110 • WRA BUSINESS & REAL ESTATE, Umbert...
Lake Ashton
![4188 MUIRFIELD LOOP, LAKE WALES, FL, 338..., Lake Wales, FL 33859]()
2 beds
|2 baths
|1,520 sq ft
|House
4188 MUIRFIELD LOOP, LAKE WALES, FL, 338...
Community: Lake Ashton
MLS L4953642 • COLDWELL BANKER REALTY, Lori Edwar...
Lake Ashton
![1069 SAWGRASS DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884]()
2 beds
|2 baths
|1,688 sq ft
|House
1069 SAWGRASS DR, WINTER HAVEN, FL, 3388...
Community: Lake Ashton
MLS P4936897 • LAKE ASHTON REALTY INC., Lori Raat...
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®
![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
Spruce Creek South
![10476 SE 178TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,473 sq ft
|House
10476 SE 178TH ST, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
MLS OM712979 • JUDY L. TROUT REALTY, Jennifer Tra...
Spruce Creek South
![17888 SE 106TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,356 sq ft
|House
17888 SE 106TH TER, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
MLS OM706131 • JUDY L. TROUT REALTY, Charles Camp...
Legacy of Leesburg
![5401 WATER LILY CT, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|2,033 sq ft
|House
5401 WATER LILY CT, LEESBURG, FL, 34748
Community: Legacy of Leesburg
MLS G5103053 • HARRISON REAL PROPERTY GROUP, Aman...
Halifax Plantation
![3341 GLENSHANE WAY, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|2,094 sq ft
|House
3341 GLENSHANE WAY, ORMOND BEACH, FL, 32...
Community: Halifax Plantation
MLS V4945146 • WATSON REALTY CORP., Carolie North...
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Legacy of Leesburg
![27313 FALCON FEATHER WAY, LEESBURG, FL, ..., Leesburg, FL 34748]()
3 beds
|2 baths
|1,611 sq ft
|House
27313 FALCON FEATHER WAY, LEESBURG, FL, ...
Community: Legacy of Leesburg
MLS G5102123 • COLDWELL BANKER VANGUARD EDGE, Jam...
Spruce Creek South
![10338 SE 178TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,008 sq ft
|House
10338 SE 178TH ST, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
MLS G5092688 • RE/MAX PREMIER REALTY LADY LK, Ger...
Traditions at Lake Ruby
![3987 BEDFORD AVE, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884]()
2 beds
|2 baths
|1,817 sq ft
|House
3987 BEDFORD AVE, WINTER HAVEN, FL, 3388...
Community: Traditions at Lake Ruby
MLS P4936091 • CENTURY 21 MYERS REALTY LAKE WALES...
Trilogy® Orlando
![626 CONSERVATION BLVD, GROVELAND, FL, 34..., Groveland, FL 34736]()
3 beds
|2 baths
|1,905 sq ft
|House
626 CONSERVATION BLVD, GROVELAND, FL, 34...
Community: Trilogy® Orlando
MLS G5102078 • COMMUNITY ELITE REALTY, Nancy Aitk...
Trilogy® Orlando
![243 BAYOU BEND RD, GROVELAND, FL, 34736, Groveland, FL 34736]()
3 beds
|2 baths
|1,838 sq ft
|House
243 BAYOU BEND RD, GROVELAND, FL, 34736
Community: Trilogy® Orlando
MLS G5097755 • COMMUNITY ELITE REALTY, Nancy Aitk...
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2,487
homes
near Winter Park
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REIN updates its listings on a daily basis. Data last updated: Nov 30, 2025.
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