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Winter Park, FL 55+ active adult communities & homes for sale - Page 22
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
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
Halifax Plantation
![3124 BAILEY ANN DR, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,717 sq ft
|House
3124 BAILEY ANN DR, ORMOND BEACH, FL, 32...
Community: Halifax Plantation
MLS 1217281 • Realty Pros Assured, Buzzy Porter
The Villages®
![16905 SE 81ST ELLERSLIE CT, THE VILLAGES..., The Villages, FL 32162]()
2 beds
|2 baths
|1,160 sq ft
|Villa
16905 SE 81ST ELLERSLIE CT, THE VILLAGES...
Community: The Villages®
MLS G5105196 • SALLY LOVE REAL ESTATE, Kim Coffer
Lake Ashton
![5197 PEBBLE BEACH BLVD, WINTER HAVEN, FL..., Winter Haven, FL 33884]()
2 beds
|2 baths
|1,677 sq ft
|House
5197 PEBBLE BEACH BLVD, WINTER HAVEN, FL...
Community: Lake Ashton
MLS P4937220 • LAKE ASHTON REALTY INC., Lori Raat...
Spruce Creek Country Club
![9385 SE 125TH ST, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
2 beds
|2 baths
|1,870 sq ft
|House
9385 SE 125TH ST, SUMMERFIELD, FL, 34491
Community: Spruce Creek Country Club
MLS O6356461 • REDFIN CORPORATION, William Larsen
Latitude Margaritaville
![317 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,321 sq ft
|House
317 GYPSY PALACE LN, DAYTONA BEACH, FL, ...
Community: Latitude Margaritaville
MLS 1212688 • Realty Pros Assured, Danny Robinson
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The Villages®
![6338 FLAXMAYER RD, THE VILLAGES, FL, 321..., The Villages, FL 32163]()
3 beds
|2 baths
|1,361 sq ft
|House
6338 FLAXMAYER RD, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5105559 • SUCCESS HOME SALES, LLC, Shiquan H...
Breakaway Trails
![24 LAKE VISTA WAY, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,544 sq ft
|House
24 LAKE VISTA WAY, ORMOND BEACH, FL, 321...
Community: Breakaway Trails
MLS TB8387697 • RMS ELITE PROPERTIES, Mark Segret...
The Villages®
![8690 SE 173RD WISTERIA ST, THE VILLAGES,..., The Villages, FL 32162]()
3 beds
|3 baths
|2,478 sq ft
|House
8690 SE 173RD WISTERIA ST, THE VILLAGES,...
Community: The Villages®
MLS G5096304 • OLYMPUS EXECUTIVE REALTY INC, Jen ...
Solivita
![487 MONTEREY ST, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5136139 • PELLEGO, LLC, Stan Wilson
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
![3279 PEBBLE BEND DR, LAKELAND, FL, 33810, Lakeland, FL 33810]()
2 beds
|2 baths
|1,456 sq ft
|Manufactured Home
3279 PEBBLE BEND DR, LAKELAND, FL, 33810
Community: Highland Fairways
MLS L4955165 • HOMETRUST REAL ESTATE & PTY MGT, K...
Solivita
![142 OLYMPUS WAY, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5127381 • PREMIER SOTHEBYS INT'L REALTY, Wal...
The Villages®
![506 DEAUVILLE CT, THE VILLAGES, FL, 3216..., The Villages, FL 32163]()
3 beds
|2 baths
|1,914 sq ft
|House
506 DEAUVILLE CT, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5099658 • RE/MAX PREMIER REALTY, Mark Sevegn...
Stonecrest
![11041 SE 174TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491]()
4 beds
|3 baths
|3,068 sq ft
|House
11041 SE 174TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
MLS C7518362 • EXP REALTY LLC, Bryan Kelsey
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Traditions at Lake Ruby
![3565 RALEIGH DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884]()
3 beds
|2 baths
|1,866 sq ft
|House
3565 RALEIGH DR, WINTER HAVEN, FL, 33884
Community: Traditions at Lake Ruby
MLS P4934495 • CENTURY 21 WATSON & MYERS REALTY, ...
The Villages®
![3191 WARBLER LOOP, THE VILLAGES, FL, 321..., The Villages, FL 32163]()
3 beds
|3 baths
|1,906 sq ft
|House
3191 WARBLER LOOP, THE VILLAGES, FL, 321...
Community: The Villages®
MLS TB8449357 • FLAT FEE MLS REALTY, Stephen Hach...
Royal Harbor
![5486 BOUNTY CIR, TAVARES, FL, 32778, Tavares, FL 32778]()
MLS G5102161 • BHHS FLORIDA REALTY, Catherine Lan...
The Villages®
![5453 WILLIAMSBURG LN, WILDWOOD, FL, 3478..., Wildwood, FL 34785]()
2 beds
|2 baths
|1,581 sq ft
|Manufactured Home
5453 WILLIAMSBURG LN, WILDWOOD, FL, 3478...
Community: The Villages®
MLS TB8455690 • AGILE GROUP REALTY, Chad Warren
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.
Huntington at Hunter's Ridge
![51 WRENDALE LOOP, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
2 beds
|2 baths
|1,603 sq ft
|House
51 WRENDALE LOOP, ORMOND BEACH, FL, 3217...
Community: Huntington at Hunter's Ridge
MLS V4944327 • REALTY PROS ASSURED, Jonathan Gild...
Bridgewater at Viera
![8444 ALISTER DR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|4 baths
|2,389 sq ft
|House
8444 ALISTER DR, MELBOURNE, FL, 32940
Community: Bridgewater at Viera
MLS 1058928 • Ellingson Properties, Gregory Ellin...
Ormond Renaissance
![799 STERTHAUS DR 207, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,523 sq ft
|Condo
799 STERTHAUS DR 207, ORMOND BEACH, FL, ...
Community: Ormond Renaissance
MLS A4670127 • INVESTY REALTY, LLC., Amy Stanley
Plantation Bay Golf & Country Club
![1111 HANSBERRY CT, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
2 beds
|2 baths
|1,542 sq ft
|Townhouse
1111 HANSBERRY CT, ORMOND BEACH, FL, 321...
Community: Plantation Bay Golf & Country Club
MLS 1219218 • Florida Investment Realty, Arun Red...
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Solivita
![461 TREVISO DR, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5137945 • BORCHINI REALTY, Yamile Osorio Var...
Scottish Highlands
![16 EASTER ROSS CT, LEESBURG, FL, 34788, Leesburg, FL 34788]()
2 beds
|2 baths
|1,418 sq ft
|House
16 EASTER ROSS CT, LEESBURG, FL, 34788
Community: Scottish Highlands
MLS OM714738 • COLDWELL BANKER VANGUARD EDGE, Val...
Plantation at Leesburg
![24345 AMBERLEAF CT, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,898 sq ft
|House
24345 AMBERLEAF CT, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS O6361845 • APEX INTERNATIONAL BROKERAGE, Zach...
The Villages®
![3536 ROANOKE ST, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,156 sq ft
|Villa
3536 ROANOKE ST, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5101733 • RE/MAX FOXFIRE - LADY LAKE, Robert...
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®
![1107 SAN ANTONIO LN, THE VILLAGES, FL, 3..., The Villages, FL 32159]()
3 beds
|2 baths
|2,034 sq ft
|House
1107 SAN ANTONIO LN, THE VILLAGES, FL, 3...
Community: The Villages®
MLS G5098998 • SALLY LOVE REAL ESTATE, Carol Juli...
The Villages®
![442 PACE LN, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,100 sq ft
|House
442 PACE LN, THE VILLAGES, FL, 32162
Community: The Villages®
MLS OM713510 • REALTY ONE GROUP DAVALLS, David St...
Twin Lakes
![5003 E FOUNTAINWOOD DR, SAINT CLOUD, FL,..., Saint Cloud, FL 34772]()
3 beds
|3 baths
|2,208 sq ft
|House
5003 E FOUNTAINWOOD DR, SAINT CLOUD, FL,...
Community: Twin Lakes
MLS O6363291 • EXP REALTY LLC, Brittany Pride
VillageWalk at Lake Nona
![12185 OBELIA LN, ORLANDO, FL, 32827, Orlando, FL 32827]()
3 beds
|3 baths
|2,022 sq ft
|House
12185 OBELIA LN, ORLANDO, FL, 32827
Community: VillageWalk at Lake Nona
MLS O6310416 • FUSILIER MANAGEMENT GROUP, Laura A...
The Villages®
![1651 DURAN DR, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,121 sq ft
|Villa
1651 DURAN DR, THE VILLAGES, FL, 32162
Community: The Villages®
MLS O6363935 • FLORIDA REALTY INVESTMENTS, Landon...
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The Country Club of Mount Dora
![1812 STAFFORD SPRINGS BLVD, MOUNT DORA, ..., Mount Dora, FL 32757]()
2 beds
|2 baths
|1,515 sq ft
|House
1812 STAFFORD SPRINGS BLVD, MOUNT DORA, ...
Community: The Country Club of Mount Dora
MLS G5105423 • BHHS FLORIDA REALTY, Joanne Levy
Solivita
![702 TORREY PINES WAY, POINCIANA, FL, 347..., Poinciana, FL 34759]()
3 beds
|3 baths
|2,190 sq ft
|House
702 TORREY PINES WAY, POINCIANA, FL, 347...
Community: Solivita
MLS 2077347 • MARYKATE & CO REALTY, MARY KATHLEEN...
Del Webb Orlando
![418 DEL SOL AVE, DAVENPORT, FL, 33837, Davenport, FL 33837]()
3 beds
|2 baths
|1,713 sq ft
|House
418 DEL SOL AVE, DAVENPORT, FL, 33837
Community: Del Webb Orlando
MLS S5133545 • KELLER WILLIAMS REALTY AT THE LAKE...
Four Seasons at Orlando
![2111 LIMESTONE TRL # 504, KISSIMMEE, FL,..., Kissimmee, FL 34747]()
3 beds
|2 baths
|2,189 sq ft
|House
2111 LIMESTONE TRL # 504, KISSIMMEE, FL,...
Community: Four Seasons at Orlando
MLS O6358113 • HOMEVEST REALTY, Erica Diaz
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.
Stonecrest
![17808 SE 115TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|3 baths
|2,233 sq ft
|House
17808 SE 115TH CT, SUMMERFIELD, FL, 3449...
Community: Stonecrest
MLS OM714475 • BASSETT PREMIER REALTY INC, Sharon...
Latitude Margaritaville
![557 HIGH TIDE LN, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,308 sq ft
|House
557 HIGH TIDE LN, DAYTONA BEACH, FL, 321...
Community: Latitude Margaritaville
MLS 1220616 • Bob Hodges and Sons Realty, Didi Wo...
The Villages®
![1514 CERVANTES PL, THE VILLAGES, FL, 321..., The Villages, FL 32159]()
3 beds
|2 baths
|2,308 sq ft
|House
1514 CERVANTES PL, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5105546 • REALTY EXECUTIVES IN THE VILLAGES,...
Scottish Highlands
![1605 SELKIRK DR, LEESBURG, FL, 34788, Leesburg, FL 34788]()
2 beds
|2 baths
|1,284 sq ft
|House
1605 SELKIRK DR, LEESBURG, FL, 34788
Community: Scottish Highlands
MLS G5105345 • COLDWELL BANKER VANGUARD EDGE, Lor...
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Stonecrest
![17974 SE 115TH CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,617 sq ft
|House
17974 SE 115TH CIR, SUMMERFIELD, FL, 344...
Community: Stonecrest
MLS OM706767 • KIEFER REALTY, PA, Scott Kiefer
Arlington Ridge
![4719 HERITAGE TRL, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,761 sq ft
|House
4719 HERITAGE TRL, LEESBURG, FL, 34748
Community: Arlington Ridge
MLS OM714339 • DISCOVER FLORIDA REALTY GROUP LLC,...
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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.
