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Winter Park, FL 55+ active adult communities & homes for sale - Page 39
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
3.8 rating (6 reviews)
![Trilogy® Orlando]()
$200Ks
- $600Ks
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
Download the Ultimate 55+ Homebuying Guide
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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)
![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 (1 reviews)
![VillageWalk at Lake Nona]()
$300Ks
- $1Ms
VillageWalk at Lake Nona, Orlando, FL
Resale Only
|
Age-targeted
|
Built 2006 - 2016
|
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
![25504 BELLE ALLIANCE, LEESBURG, FL, 3474..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,674 sq ft
|Manufactured Home
25504 BELLE ALLIANCE, LEESBURG, FL, 3474...
Community: Plantation at Leesburg
MLS G5104384 • CENTURY 21 MYERS REALTY, Cary Fier
Breakaway Trails
![4 CREEK BEND WAY, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
5 beds
|3 baths
|3,625 sq ft
|House
4 CREEK BEND WAY, ORMOND BEACH, FL, 3217...
Community: Breakaway Trails
MLS 1213446 • LoKation, Lori Spada
Lake Ashton
![4240 DUNMORE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859]()
2 beds
|2 baths
|1,771 sq ft
|House
4240 DUNMORE DR, LAKE WALES, FL, 33859
Community: Lake Ashton
MLS P4933500 • GLOBAL LIFESTYLE LLC, Brad Kirwan
The Villages®
![491 HARLOW LN, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|1,958 sq ft
|House
491 HARLOW LN, THE VILLAGES, FL, 32163
Community: The Villages®
MLS OM708408 • ASHLEY YATES REALTY, Danielle Smit...
Cresswind at Victoria Gardens
![115 HERON POINT WAY, DELAND, FL, 32724, Deland, FL 32724]()
3 beds
|2 baths
|1,773 sq ft
|House
115 HERON POINT WAY, DELAND, FL, 32724
Community: Cresswind at Victoria Gardens
MLS A11865319 • A. Leon Realty Inc., Adolfo Quint...
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Summer Trees
![102 UNDERBRUSH TRL, PORT ORANGE, FL, 321..., Port Orange, FL 32128]()
2 beds
|2 baths
|1,370 sq ft
|House
102 UNDERBRUSH TRL, PORT ORANGE, FL, 321...
Community: Summer Trees
MLS V4941482 • GAFF'S REALTY COMPANY, Tom Grasber...
Royal Highlands
![5902 PRINCESS DIANA CT, LEESBURG, FL, 34..., Leesburg, FL 34748]()
3 beds
|3 baths
|2,021 sq ft
|House
5902 PRINCESS DIANA CT, LEESBURG, FL, 34...
Community: Royal Highlands
MLS G5102760 • EXIT REALTY TRI-COUNTY, Jason Shor...
Cresswind at Victoria Gardens
![123 AVENHAM DR, DELAND, FL, 32724, Deland, FL 32724]()
3 beds
|2 baths
|1,894 sq ft
|House
123 AVENHAM DR, DELAND, FL, 32724
Community: Cresswind at Victoria Gardens
MLS V4945564 • COLDWELL BANKER COAST REALTY, Jaso...
Carillon Lakes
![3850 SERENADE LN # 3850, LAKELAND, FL, 3..., Lakeland, FL 33811]()
2 beds
|2 baths
|1,812 sq ft
|Condo
3850 SERENADE LN # 3850, LAKELAND, FL, 3...
Community: Carillon Lakes
MLS TB8442576 • PROVANTAGE GROUP LLC, Jack Guerra
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.
Halifax Plantation
![2853 MONAGHAN DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,113 sq ft
|House
2853 MONAGHAN DR, ORMOND BEACH, FL, 3217...
Community: Halifax Plantation
MLS 1218041 • Florida Bluewater Realty LLC, Natha...
Arlington Ridge
![4714 INDEPENDENCE TRL, LEESBURG, FL, 347..., Leesburg, FL 34748]()
3 beds
|2 baths
|1,753 sq ft
|House
4714 INDEPENDENCE TRL, LEESBURG, FL, 347...
Community: Arlington Ridge
MLS OM714183 • DISCOVER FLORIDA REALTY GROUP LLC,...
Trilogy® Orlando
![103 CRESCENT MOON DR, GROVELAND, FL, 347..., Groveland, FL 34736]()
3 beds
|2 baths
|1,671 sq ft
|House
103 CRESCENT MOON DR, GROVELAND, FL, 347...
Community: Trilogy® Orlando
MLS O6333177 • POP REALTY POWERED BY SELLSTATE, J...
Lakes of Mount Dora
![8252 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757]()
3 beds
|2 baths
|1,473 sq ft
|House
8252 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...
Community: Lakes of Mount Dora
MLS G5102215 • ERA GRIZZARD REAL ESTATE, Scott Mc...
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Lakes of Mount Dora
![8852 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757]()
3 beds
|2 baths
|2,018 sq ft
|House
8852 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...
Community: Lakes of Mount Dora
MLS G5102771 • ERA GRIZZARD REAL ESTATE, Scott Mc...
Lakes of Mount Dora
![2318 WAKEFIELD WAY, MOUNT DORA, FL, 3275..., Mount Dora, FL 32757]()
3 beds
|2 baths
|1,919 sq ft
|House
2318 WAKEFIELD WAY, MOUNT DORA, FL, 3275...
Community: Lakes of Mount Dora
MLS G5105072 • ERA GRIZZARD REAL ESTATE, Scott Mc...
VillageWalk at Lake Nona
![11932 LORENZA LN, ORLANDO, FL, 32827, Orlando, FL 32827]()
3 beds
|3 baths
|1,830 sq ft
|Townhouse
11932 LORENZA LN, ORLANDO, FL, 32827
Community: VillageWalk at Lake Nona
MLS S5140170 • KELLER WILLIAMS LEGACY REALTY, Haz...
The Villages®
![420 CANTERBURY CT, THE VILLAGES, FL, 321..., The Villages, FL 32162]()
1 beds
|1 baths
|875 sq ft
|Villa
420 CANTERBURY CT, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5104296 • FILLINGAME & ASSOCIATES, Jean Fill...
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.
Royal Palm
![1322 COCONUT PALM CIR, PORT ORANGE, FL, ..., Port Orange, FL 32128]()
3 beds
|2 baths
|2,023 sq ft
|House
1322 COCONUT PALM CIR, PORT ORANGE, FL, ...
Community: Royal Palm
MLS 1220737 • Watson Realty Corp., Robert Stein
Venetian Bay
![3039 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|1,672 sq ft
|House
3039 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS O6308215 • ATKINS REALTY GROUP, Larry Atkins
The Villages®
![718 SHELTON ST, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|1,607 sq ft
|House
718 SHELTON ST, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5104756 • DOWN HOME REALTY, LLLP, Mike Joy
Kings Ridge
![3525 ROLLINGBROOK ST, CLERMONT, FL, 3471..., Clermont, FL 34711]()
2 beds
|2 baths
|1,548 sq ft
|House
3525 ROLLINGBROOK ST, CLERMONT, FL, 3471...
Community: Kings Ridge
MLS G5097071 • MICKI BLACKBURN REALTY, Patricia D...
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Plantation Bay Golf & Country Club
![801 ARBOR GLEN CT, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,569 sq ft
|House
801 ARBOR GLEN CT, ORMOND BEACH, FL, 321...
Community: Plantation Bay Golf & Country Club
MLS V4943501 • REALTY PROS ASSURED, Mary Maholias
The Villages®
![108 WINTERBERRY AVE, WILDWOOD, FL, 34785, Wildwood, FL 34785]()
2 beds
|2 baths
|1,040 sq ft
|Manufactured Home
108 WINTERBERRY AVE, WILDWOOD, FL, 34785
Community: The Villages®
MLS G5105262 • DOWN HOME REALTY, LLLP, Colleen A....
Sandpiper Golf & Country Club
![6119 SANDPIPERS DR, LAKELAND, FL, 33809, Lakeland, FL 33809]()
2 beds
|2 baths
|1,148 sq ft
|House
6119 SANDPIPERS DR, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS L4957923 • COLDWELL BANKER REALTY, Ginger Qui...
Grand Haven
![34 OSPREY CIR, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
MLS FC311638 • COASTAL GATEWAY REAL ESTATE GR, An...
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®
![1802 PETUNIA LN, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,434 sq ft
|Manufactured Home
1802 PETUNIA LN, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5099228 • COLDWELL BANKER VANGUARD LIFESTYLE...
Cresswind at Victoria Gardens
![1018 HERON POINT CIR, DELAND, FL, 32724, Deland, FL 32724]()
4 beds
|3 baths
|2,091 sq ft
|House
1018 HERON POINT CIR, DELAND, FL, 32724
Community: Cresswind at Victoria Gardens
MLS V4942681 • GREENE REALTY OF FLORIDA LLC, Heat...
Heritage Hills
![3674 CALADESI RD, CLERMONT, FL, 34711, Clermont, FL 34711]()
3 beds
|2 baths
|1,672 sq ft
|House
3674 CALADESI RD, CLERMONT, FL, 34711
Community: Heritage Hills
MLS O6336787 • BHHS FLORIDA REALTY, Andrew Kincai...
Heritage Hills
![3553 BELLAND CIR A, CLERMONT, FL, 34711, Clermont, FL 34711]()
2 beds
|2 baths
|1,503 sq ft
|Villa
3553 BELLAND CIR A, CLERMONT, FL, 34711
Community: Heritage Hills
MLS O6363333 • BHHS FLORIDA REALTY, Patti Kincaid
Heritage Hills
![3524 LITCHFIELD CT, CLERMONT, FL, 34711, Clermont, FL 34711]()
4 beds
|3 baths
|2,293 sq ft
|House
3524 LITCHFIELD CT, CLERMONT, FL, 34711
Community: Heritage Hills
MLS O6344422 • BHHS FLORIDA REALTY, Patti Kincaid
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Stonecrest
![12193 SE 175TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,647 sq ft
|House
12193 SE 175TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
MLS G5105898 • RE/MAX PREMIER REALTY LADY LK, Deb...
Vienna Square
![1703 LINZ CT, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884]()
2 beds
|2 baths
|1,164 sq ft
|Villa
1703 LINZ CT, WINTER HAVEN, FL, 33884
Community: Vienna Square
MLS P4933885 • DGCF REALTY ADVISORS LLC, Austin S...
Palms at Serenoa
![17795 BLAZING STAR CIR, CLERMONT, FL, 34..., Clermont, FL 34714]()
3 beds
|2 baths
|1,722 sq ft
|House
17795 BLAZING STAR CIR, CLERMONT, FL, 34...
Community: Palms at Serenoa
MLS S5128094 • EXP REALTY LLC, John Gomez
Lakes of Mount Dora
![8065 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757]()
4 beds
|3 baths
|3,551 sq ft
|House
8065 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...
Community: Lakes of Mount Dora
MLS G5103865 • WATSON REALTY CORP, Jonathan Faw
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.
Highland Fairways
![1967 LONG BOAT DR, LAKELAND, FL, 33810, Lakeland, FL 33810]()
2 beds
|2 baths
|1,955 sq ft
|House
1967 LONG BOAT DR, LAKELAND, FL, 33810
Community: Highland Fairways
MLS U8253025 • FUTURE HOME REALTY INC, Frank Poll...
Spruce Creek Country Club
![9063 SE 120TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,346 sq ft
|House
9063 SE 120TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek Country Club
MLS OM712093 • EXP REALTY LLC, Kelly LaFave
The Lakes at Harmony
![7480 WING SPAN WAY, HARMONY, FL, 34773, Harmony, FL 34773]()
5 beds
|4 baths
|2,717 sq ft
|House
7480 WING SPAN WAY, HARMONY, FL, 34773
Community: The Lakes at Harmony
MLS O6335751 • RESORT REALTY GROUP LTD INC, David...
The Villages®
![1641 OSPREY AVE, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,156 sq ft
|Villa
1641 OSPREY AVE, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5105821 • IM REALTY, Ira Miller
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Arlington Ridge
![26555 MANASSAS DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,888 sq ft
|House
26555 MANASSAS DR, LEESBURG, FL, 34748
Community: Arlington Ridge
MLS G5104692 • ERA GRIZZARD REAL ESTATE, Melissa ...
Heritage Landings
![2756 GRANDBURY GROVE RD, LAKELAND, FL, 3..., Lakeland, FL 33811]()
4 beds
|2 baths
|1,867 sq ft
|House
2756 GRANDBURY GROVE RD, LAKELAND, FL, 3...
Community: Heritage Landings
MLS TB8457827 • TROWBRIDGE REALTY CORP, Matthew D...
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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.
