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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
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.
$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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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
- $500Ks
Trilogy® Orlando, Groveland, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2022
|
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
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
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
- $800Ks
Del Webb at Viera, Melbourne, FL
New Construction
|
55+ age-restricted
|
Built 2021 - 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
Want to learn more about 55+ communities in Winter Park?
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Questions? Call us:
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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
- $500Ks
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
The Villages®
![1542 WYATT AVE, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,530 sq ft
|House
1542 WYATT AVE, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5103668 • COLDWELL BANKER VANGUARD LIFESTYLE...
The Villages®
![1501 ALFONSO LN, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,014 sq ft
|House
1501 ALFONSO LN, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5103576 • HOMERUN REALTY, LLC, Michael Engla...
Solivita
![531 VILLA PARK RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5131192 • PELLEGO, LLC, Stan Wilson
Pelican Bay Daytona Beach
![513 PELICAN BAY DR, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32119]()
3 beds
|3 baths
|2,256 sq ft
|House
513 PELICAN BAY DR, DAYTONA BEACH, FL, 3...
Community: Pelican Bay Daytona Beach
MLS 1220054 • Oceans Luxury Realty Full Service L...
New
Spruce Creek Country Club
![9105 SE 125TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
2 beds
|2 baths
|2,148 sq ft
|House
9105 SE 125TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek Country Club
MLS OM714080 • BROKER ASSOCIATES REALTY, Rich Den...
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The Villages®
![3327 DALKEITH TER, THE VILLAGES, FL, 321..., The Villages, FL 32163]()
3 beds
|2 baths
|2,124 sq ft
|House
3327 DALKEITH TER, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5102757 • REALTY EXECUTIVES IN THE VILLAGES,...
Venetian Bay
![3014 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|1,587 sq ft
|Townhouse
3014 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS O6327495 • INVESTOR'S REAL ESTATE LLC, Luz He...
Spruce Creek Country Club
![12470 SE 92ND TER, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,244 sq ft
|House
12470 SE 92ND TER, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS OM713186 • RE/MAX PREMIER REALTY LADY LK, Jay...
Grand Haven
![15 CHINIER ST, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
MLS FC314149 • COASTAL GATEWAY REAL ESTATE GROUP,...
The Villages®
![1505 LAVACA LN, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
3 beds
|2 baths
|1,897 sq ft
|House
1505 LAVACA LN, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5102401 • RE/MAX FOXFIRE - LADY LAKE, Kelly ...
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
Halifax Plantation
![4121 SALINA LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
4 beds
|2 baths
|2,317 sq ft
|House
4121 SALINA LN, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
MLS V4946104 • KELLER WILLIAMS RLTY FL. PARTN, Tr...
New
Grand Haven
![150 W WATERSIDE PKWY, PALM COAST, FL, 32..., Palm Coast, FL 32137]()
2 beds
|2 baths
|1,619 sq ft
|House
150 W WATERSIDE PKWY, PALM COAST, FL, 32...
Community: Grand Haven
MLS FC314375 • GRAND LIVING REALTY, Joan Paulus
New
Ridgehaven
![165 PARKHAVEN DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,572 sq ft
|House
165 PARKHAVEN DR, ORMOND BEACH, FL, 3217...
Community: Ridgehaven
MLS O6363528 • MERITAGE HOMES OF FL REALTY, Tatia...
New
Spruce Creek Country Club
![13026 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491]()
2 beds
|3 baths
|2,722 sq ft
|House
13026 SE 97TH TERRACE RD, SUMMERFIELD, F...
Community: Spruce Creek Country Club
MLS A4673406 • FLATFEE.COM, Cliff Glansen
New
Lake Ashton
![4480 STRATHMORE DR, LAKE WALES, FL, 3385..., Lake Wales, FL 33859]()
2 beds
|2 baths
|1,523 sq ft
|House
4480 STRATHMORE DR, LAKE WALES, FL, 3385...
Community: Lake Ashton
MLS P4937136 • LAKE ASHTON REALTY INC., Candra Al...
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New
Grand Haven
![7 MARSHVIEW LN, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
MLS FC314359 • NOKI REALTY, Olga Lagunchik
New
Del Webb Minneola
![2534 DEL WEBB DR, MINNEOLA, FL, 34715, Minneola, FL 34715]()
3 beds
|3 baths
|2,898 sq ft
|House
2534 DEL WEBB DR, MINNEOLA, FL, 34715
Community: Del Webb Minneola
MLS O6363078 • PULTE REALTY OF NORTH FLORIDA LLC,...
New
Tohoqua Reserve
![1807 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744]()
2 beds
|2 baths
|1,579 sq ft
|Villa
1807 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
MLS O6363132 • PULTE REALTY OF NORTH FLORIDA LLC,...
New
Scottish Highlands
![305 BRIGADOON CIR, LEESBURG, FL, 34788, Leesburg, FL 34788]()
2 beds
|2 baths
|1,270 sq ft
|House
305 BRIGADOON CIR, LEESBURG, FL, 34788
Community: Scottish Highlands
MLS G5104886 • COLDWELL BANKER VANGUARD EDGE, Lor...
New
The Villages®
![3068 SPANISH MOSS WAY, THE VILLAGES, FL,..., The Villages, FL 32163]()
3 beds
|2 baths
|2,309 sq ft
|House
3068 SPANISH MOSS WAY, THE VILLAGES, FL,...
Community: The Villages®
MLS G5104883 • 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.
New
Traditions at Lake Ruby
![3348 RALEIGH DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884]()
2 beds
|2 baths
|1,185 sq ft
|House
3348 RALEIGH DR, WINTER HAVEN, FL, 33884
Community: Traditions at Lake Ruby
MLS P4937125 • LA ROSA REALTY PRESTIGE, Keith St....
New
Grand Haven
![215 WILLOW OAK WAY, PALM COAST, FL, 3213..., Palm Coast, FL 32137]()
3 beds
|3 baths
|2,584 sq ft
|House
215 WILLOW OAK WAY, PALM COAST, FL, 3213...
Community: Grand Haven
MLS FC314175 • COASTAL GATEWAY REAL ESTATE GROUP,...
New
Pennbrooke Fairways
![818 FOREST BREEZE PATH, LEESBURG, FL, 34..., Leesburg, FL 34748]()
3 beds
|2 baths
|2,111 sq ft
|House
818 FOREST BREEZE PATH, LEESBURG, FL, 34...
Community: Pennbrooke Fairways
MLS G5104636 • MORRIS REALTY AND INVESTMENTS, The...
New
The Villages®
![978 SMYRNA ST, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,397 sq ft
|Villa
978 SMYRNA ST, THE VILLAGES, FL, 32162
Community: The Villages®
MLS TB8449535 • CHARLES RUTENBERG REALTY INC, Bil...
Ridgehaven
![449 BROOKHAVEN TRL, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174]()
3 beds
|3 baths
|2,181 sq ft
|House
449 BROOKHAVEN TRL, ORMOND BEACH, FL, 32...
Community: Ridgehaven
MLS O6328577 • MERITAGE HOMES OF FL REALTY, Tatia...
Want to learn more about 55+ communities in Winter Park?
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Questions? Call us:
(888) 625-4885
Plantation at Leesburg
![4634 SUMMERBRIDGE CIR, LEESBURG, FL, 347..., Leesburg, FL 34748]()
3 beds
|2 baths
|2,005 sq ft
|House
4634 SUMMERBRIDGE CIR, LEESBURG, FL, 347...
Community: Plantation at Leesburg
MLS G5089609 • CENTURY 21 MYERS REALTY, A Indicto...
Royal Palm
![1315 COCONUT PALM CIR, PORT ORANGE, FL, ..., Port Orange, FL 32128]()
4 beds
|2 baths
|1,989 sq ft
|House
1315 COCONUT PALM CIR, PORT ORANGE, FL, ...
Community: Royal Palm
MLS 1220297 • Florida Investment Realty, Arun Red...
Sandpiper Golf & Country Club
![6059 CONDOR DR, LAKELAND, FL, 33809, Lakeland, FL 33809]()
3 beds
|2 baths
|2,195 sq ft
|House
6059 CONDOR DR, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS P4936073 • COLDWELL BANKER REALTY, Ed Fahner
Venetian Bay
![2915 N ASCIANO CT, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|2,181 sq ft
|House
2915 N ASCIANO CT, NEW SMYRNA BEACH, FL,...
Community: Venetian Bay
MLS 1208050 • LoKation, Tiffany Garten
Del Webb Orlando
![136 DEL SOL AVE, DAVENPORT, FL, 33837, Davenport, FL 33837]()
3 beds
|3 baths
|1,982 sq ft
|House
136 DEL SOL AVE, DAVENPORT, FL, 33837
Community: Del Webb Orlando
MLS S5131590 • GATHERING ROOM REAL ESTATE, Shelly...
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 Orlando
![300 DEL SOL AVE, DAVENPORT, FL, 33837, Davenport, FL 33837]()
2 beds
|2 baths
|1,728 sq ft
|House
300 DEL SOL AVE, DAVENPORT, FL, 33837
Community: Del Webb Orlando
MLS S5133334 • GATHERING ROOM REAL ESTATE, Shelly...
VillageWalk at Lake Nona
![11846 NAUTICA DR, ORLANDO, FL, 32827, Orlando, FL 32827]()
3 beds
|3 baths
|1,810 sq ft
|Townhouse
11846 NAUTICA DR, ORLANDO, FL, 32827
Community: VillageWalk at Lake Nona
MLS O6285995 • LPT REALTY, LLC, Maria Rodriguez
Kings Ridge
![3907 ALLAMANDA CT, CLERMONT, FL, 34711, Clermont, FL 34711]()
3 beds
|2 baths
|1,783 sq ft
|House
3907 ALLAMANDA CT, CLERMONT, FL, 34711
Community: Kings Ridge
MLS G5097799 • KELLER WILLIAMS ELITE PARTNERS III...
Highland Fairways
![2137 GRAND CYPRESS DR, LAKELAND, FL, 338..., Lakeland, FL 33810]()
3 beds
|2 baths
|1,808 sq ft
|House
2137 GRAND CYPRESS DR, LAKELAND, FL, 338...
Community: Highland Fairways
MLS B4902076 • CRAIG BURKE REAL ESTATE GROUP, LLC...
New
The Villages®
![651 D ANGELO LN, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,357 sq ft
|House
651 D ANGELO LN, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5104824 • REALTY EXECUTIVES IN THE VILLAGES,...
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(888) 625-4885
Spring Lake Towers
![700 MIRROR TER 303, WINTER HAVEN, FL, 33..., Winter Haven, FL 33881]()
2 beds
|2 baths
|1,029 sq ft
|Condo
700 MIRROR TER 303, WINTER HAVEN, FL, 33...
Community: Spring Lake Towers
MLS P4934745 • LPT REALTY, LLC, Kevin Tison
The Villages®
![5068 NE 121ST AVE, OXFORD, FL, 34484, Oxford, FL 34484]()
3 beds
|2 baths
|1,488 sq ft
|House
5068 NE 121ST AVE, OXFORD, FL, 34484
Community: The Villages®
MLS G5098035 • REALTY EXECUTIVES IN THE VILLAGES,...
Royal Highlands
![21849 TARTAN ST, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|2,074 sq ft
|House
21849 TARTAN ST, LEESBURG, FL, 34748
Community: Royal Highlands
MLS G5104455 • COLDWELL BANKER HUBBARD HANSEN, Je...
New
Spruce Creek Country Club
![13655 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491]()
3 beds
|2 baths
|2,103 sq ft
|House
13655 SE 97TH TERRACE RD, SUMMERFIELD, F...
Community: Spruce Creek Country Club
MLS G5104734 • EXP REALTY LLC, Lili Whittington
Lake Ashton
![4115 ABERDEEN LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859]()
2 beds
|2 baths
|1,688 sq ft
|House
4115 ABERDEEN LN, LAKE WALES, FL, 33859
Community: Lake Ashton
MLS O6344464 • KELLER WILLIAMS ADVANTAGE 2 REALTY...
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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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