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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
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$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
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Questions? Call us:
(888) 625-4885
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®
![116 CYPRESS RD, WILDWOOD, FL, 34785, Wildwood, FL 34785]()
2 beds
|2 baths
|1,040 sq ft
|Manufactured Home
116 CYPRESS RD, WILDWOOD, FL, 34785
Community: The Villages®
MLS G5101054 • DOWN HOME REALTY, LLLP, Colleen A....
Latitude Margaritaville
![422 GOOD LIFE WAY, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124]()
3 beds
|2 baths
|1,922 sq ft
|House
422 GOOD LIFE WAY, DAYTONA BEACH, FL, 32...
Community: Latitude Margaritaville
MLS V4943508 • COLDWELL BANKER REALTY, Edit Perez
Grand Haven
![8 N VILLAGE DR, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
MLS FC308288 • COASTAL GATEWAY REAL ESTATE GROUP,...
Latitude Margaritaville
![500 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,464 sq ft
|House
500 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...
Community: Latitude Margaritaville
MLS 1219080 • Realty Hub, Cherri Tindall
Spruce Creek Country Club
![9126 SE 125TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,757 sq ft
|House
9126 SE 125TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek Country Club
MLS OM711149 • BROKER ASSOCIATES REALTY, Rich Den...
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Royal Highlands
![4814 SAINT ANDREWS ARC, LEESBURG, FL, 34..., Leesburg, FL 34748]()
3 beds
|2 baths
|1,728 sq ft
|House
4814 SAINT ANDREWS ARC, LEESBURG, FL, 34...
Community: Royal Highlands
MLS G5098753 • FLORIDA PLUS REALTY, LLC, Tonya Ti...
Del Webb Minneola
![2759 PURPLE MEADOW CT, MINNEOLA, FL, 347..., Minneola, FL 34715]()
2 beds
|2 baths
|1,405 sq ft
|House
2759 PURPLE MEADOW CT, MINNEOLA, FL, 347...
Community: Del Webb Minneola
MLS O6319407 • RE/MAX SELECT GROUP, Mike Mondello
Royal Highlands
![20751 QUEEN ALEXANDRA DR, LEESBURG, FL, ..., Leesburg, FL 34748]()
3 beds
|3 baths
|2,224 sq ft
|House
20751 QUEEN ALEXANDRA DR, LEESBURG, FL, ...
Community: Royal Highlands
MLS G5094138 • VANGIE BERRY SIGNATURE REALTY, Ang...
Spruce Creek Country Club
![9330 SE 132ND PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
3 beds
|3 baths
|2,333 sq ft
|House
9330 SE 132ND PL, SUMMERFIELD, FL, 34491
Community: Spruce Creek Country Club
MLS OM711747 • JUDY L. TROUT REALTY, Kevin Boutwe...
Stonecrest
![17485 SE 121ST CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,990 sq ft
|House
17485 SE 121ST CIR, SUMMERFIELD, FL, 344...
Community: Stonecrest
MLS OM707770 • KELLER WILLIAMS CORNERSTONE RE, Ri...
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.
Spruce Creek South
![10492 SE 178TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,066 sq ft
|House
10492 SE 178TH ST, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
MLS OM705001 • BERKSHIRE HATHAWAY HS FLORIDA, Mar...
Plantation at Leesburg
![24125 PEEKSKILL ST, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,935 sq ft
|House
24125 PEEKSKILL ST, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS O6304197 • WEICHERT, REALTORS-HALLMARK PR, Da...
Stonecrest
![11396 SE 178TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|3 baths
|1,735 sq ft
|Villa
11396 SE 178TH PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
MLS G5103313 • RE/MAX PREMIER REALTY LADY LK, Cin...
Halifax Plantation
![1318 ASHER CT, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,684 sq ft
|House
1318 ASHER CT, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
MLS FC313470 • WATSON REALTY CORP, Bogdana Subach...
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...
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Royal Highlands
![20700 QUEEN ALEXANDRA DR, LEESBURG, FL, ..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,332 sq ft
|House
20700 QUEEN ALEXANDRA DR, LEESBURG, FL, ...
Community: Royal Highlands
MLS G5102986 • FLORIDA PLUS REALTY, LLC, Tonya Ti...
Spruce Creek South
![17961 SE 105TH AVE, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,144 sq ft
|House
17961 SE 105TH AVE, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
MLS G5101463 • RE/MAX PREMIER REALTY LADY LK, Ger...
Highland Lakes
![5530 ROSEWALL CIR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,120 sq ft
|Villa
5530 ROSEWALL CIR, LEESBURG, FL, 34748
Community: Highland Lakes
MLS G5101613 • RE/MAX SELECT PARTNERS, Tracy Camp...
Royal Highlands
![22228 OXFORD HEIGHTS DR, LEESBURG, FL, 3..., Leesburg, FL 34748]()
3 beds
|2 baths
|1,826 sq ft
|House
22228 OXFORD HEIGHTS DR, LEESBURG, FL, 3...
Community: Royal Highlands
MLS G5101321 • FLORIDA PLUS REALTY, LLC, Tonya Ti...
Plantation at Leesburg
![25527 OAK ALY, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,518 sq ft
|House
25527 OAK ALY, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5093909 • CARLINO REAL ESTATE GROUP INC, Mar...
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.
Plantation at Leesburg
![4644 RIVER RIDGE DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,469 sq ft
|House
4644 RIVER RIDGE DR, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS O6295026 • HOMEVEST REALTY, Erica Diaz
Pennbrooke Fairways
![143 WESTWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,148 sq ft
|Manufactured Home
143 WESTWOOD DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS O6333544 • SAND DOLLAR REALTY GROUP INC, Hoss...
Solivita
![915 SAN RAPHAEL ST, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5136337 • BORCHINI REALTY, Charles Borchini
Stonecrest
![11215 SE 172ND PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,858 sq ft
|House
11215 SE 172ND PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
MLS G5097531 • CHARLES RUTENBERG REALTY ORLANDO, ...
Latitude Margaritaville
![568 HIGH TIDE LN, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,308 sq ft
|Townhouse
568 HIGH TIDE LN, DAYTONA BEACH, FL, 321...
Community: Latitude Margaritaville
MLS 1219496 • Beycome of Florida LLC, Steven Kole...
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Solivita
![258 SAND PIPER DR, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5137571 • FAIRWAY REALTY OF SOLIVITA, Elizab...
Bridgewater at Viera
![2768 MILLENNIUM CIR, MELBOURNE, FL, 3294..., Melbourne, FL 32940]()
2 beds
|2 baths
|1,827 sq ft
|House
2768 MILLENNIUM CIR, MELBOURNE, FL, 3294...
Community: Bridgewater at Viera
MLS 1060977 • Legacy Group Incorporated, Shay Dol...
Latitude Margaritaville
![279 LATITUDE DR, DAYTONA BEACH, FL, 3212..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,205 sq ft
|House
279 LATITUDE DR, DAYTONA BEACH, FL, 3212...
Community: Latitude Margaritaville
MLS FC312730 • ADAMS, CAMERON & CO., REALTORS, Jo...
Twin Lakes
![2789 SOUTHLAND ST, SAINT CLOUD, FL, 3477..., Saint Cloud, FL 34772]()
3 beds
|3 baths
|2,365 sq ft
|House
2789 SOUTHLAND ST, SAINT CLOUD, FL, 3477...
Community: Twin Lakes
MLS O6296889 • EXP REALTY LLC, Dawn Grigsby
Venetian Bay
![453 VENETIAN VILLA DR, NEW SMYRNA BEACH,..., New Smyrna Beach, FL 32168]()
5 beds
|4 baths
|3,051 sq ft
|House
453 VENETIAN VILLA DR, NEW SMYRNA BEACH,...
Community: Venetian Bay
MLS TB8412233 • CENTURY 21 INTEGRA, Terrell Newbe...
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 Sunbridge
![2793 NATURE VIEW RD, SAINT CLOUD, FL, 34..., Saint Cloud, FL 34771]()
4 beds
|3 baths
|2,761 sq ft
|House
2793 NATURE VIEW RD, SAINT CLOUD, FL, 34...
Community: Del Webb Sunbridge
MLS O6312924 • LPT REALTY, LLC, Manuel Delgado
Twin Lakes
![4921 CATALPA DR, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772]()
3 beds
|3 baths
|2,365 sq ft
|House
4921 CATALPA DR, SAINT CLOUD, FL, 34772
Community: Twin Lakes
MLS S5137679 • WEICHERT REALTORS HALLMARK PRO, Sh...
Plantation at Leesburg
![24540 MADEWOOD AVE, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|3 baths
|2,611 sq ft
|House
24540 MADEWOOD AVE, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5100626 • CENTURY 21 MYERS REALTY, Debra Ask...
Stonecrest
![11120 SE 168TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491]()
3 beds
|2 baths
|2,357 sq ft
|House
11120 SE 168TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
MLS O6305610 • AREA PRO REALTY, Shawn Murphy
Kings Ridge
![3667 KINGSWOOD CT, CLERMONT, FL, 34711, Clermont, FL 34711]()
2 beds
|2 baths
|1,552 sq ft
|House
3667 KINGSWOOD CT, CLERMONT, FL, 34711
Community: Kings Ridge
MLS O6275507 • FLORIDA PRESTIGIOUS HOMES INC, Ian...
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55places can help!
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(888) 625-4885
VillageWalk at Lake Nona
![12244 PESCARA LN, ORLANDO, FL, 32827, Orlando, FL 32827]()
3 beds
|2 baths
|1,542 sq ft
|Villa
12244 PESCARA LN, ORLANDO, FL, 32827
Community: VillageWalk at Lake Nona
MLS O6343917 • KELLER WILLIAMS ADVANTAGE 2 REALTY...
Plantation Bay Golf & Country Club
![815 WESTLAKE DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,652 sq ft
|House
815 WESTLAKE DR, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS FC312582 • CLAIRE HUNTER REALTY, Brian Hunter
Foxwood Lake Estates
![1798 FOX HILL DR, LAKELAND, FL, 33810, Lakeland, FL 33810]()
3 beds
|2 baths
|1,176 sq ft
|Manufactured Home
1798 FOX HILL DR, LAKELAND, FL, 33810
Community: Foxwood Lake Estates
MLS S5131144 • LPT REALTY, LLC, Tania Resto
Breakaway Trails
![61 COQUINA RIDGE WAY, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,566 sq ft
|House
61 COQUINA RIDGE WAY, ORMOND BEACH, FL, ...
Community: Breakaway Trails
MLS 1211048 • Realty Pros Assured, Patricia McKin...
Lake Ashton
![3064 DUNMORE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859]()
3 beds
|2 baths
|2,394 sq ft
|House
3064 DUNMORE DR, LAKE WALES, FL, 33859
Community: Lake Ashton
MLS P4936831 • LAKE ASHTON REALTY INC., Lori Raat...
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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.
This application does not include information on all of the properties available for sale at this time.
