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Winter Park, FL 55+ active adult communities & homes for sale - Page 18
90 communities near Winter Park
2,377 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
- $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
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]()
$300Ks
- $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
Scottish Highlands
![1902 TWEED CT, LEESBURG, FL, 34788, Leesburg, FL 34788]()
2 beds
|2 baths
|1,176 sq ft
|House
1902 TWEED CT, LEESBURG, FL, 34788
Community: Scottish Highlands
MLS V4943763 • COLDWELL BANKER RESIDENTIAL RE, Ka...
Latitude Margaritaville
![856 MARGARITAVILLE AVE, DAYTONA BEACH, F..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,862 sq ft
|House
856 MARGARITAVILLE AVE, DAYTONA BEACH, F...
Community: Latitude Margaritaville
MLS 1219623 • 386RealEstate.com, Kevin Kling
The Villages®
![1729 MOUNTVILLE CT, THE VILLAGES, FL, 32..., The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
1729 MOUNTVILLE CT, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5105638 • LPT REALTY, LLC, Bob Woodsford
Latitude Margaritaville
![572 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,464 sq ft
|House
572 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...
Community: Latitude Margaritaville
MLS 1220476 • 386RealEstate.com, Kevin Kling
The Villages®
![622 JENNIFER DR, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|1 baths
|936 sq ft
|Manufactured Home
622 JENNIFER DR, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5103486 • RE/MAX PREMIER REALTY LADY LK, Mat...
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Heritage Isle
![6939 MCGRADY DR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|2 baths
|2,015 sq ft
|House
6939 MCGRADY DR, MELBOURNE, FL, 32940
Community: Heritage Isle
MLS 1055131 • Dalton Wade, Inc., Rachael Renee Hu...
The Villages®
![766 ARTESIA AVE, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
766 ARTESIA AVE, THE VILLAGES, FL, 32162
Community: The Villages®
MLS O6337827 • NETWORTH REALTY OF ORLANDO, LLC, W...
Solivita
![726 IRVINE RANCH RD, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759]()
3 beds
|3 baths
|2,427 sq ft
|House
726 IRVINE RANCH RD, KISSIMMEE, FL, 3475...
Community: Solivita
MLS S5128034 • PELLEGO, LLC, Stan Wilson
New
Lake Ashton
![4189 LIMERICK DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859]()
2 beds
|2 baths
|2,227 sq ft
|House
4189 LIMERICK DR, LAKE WALES, FL, 33859
Community: Lake Ashton
MLS P4937366 • A+ REALTY LLC, Emily Muscarella
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®
![3814 FELLOWSHIP AVE, THE VILLAGES, FL, 3..., The Villages, FL 32163]()
3 beds
|2 baths
|2,109 sq ft
|House
3814 FELLOWSHIP AVE, THE VILLAGES, FL, 3...
Community: The Villages®
MLS G5103326 • SALLY LOVE REAL ESTATE, Michael Sc...
The Villages®
![1981 ANNISTON DR, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
3 beds
|2 baths
|1,685 sq ft
|Villa
1981 ANNISTON DR, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5101489 • RE/MAX PREMIER REALTY, Hope Wilson
The Villages®
![4234 MCCLOY AVE, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|3 baths
|2,033 sq ft
|House
4234 MCCLOY AVE, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5101166 • LPT REALTY, LLC, Kaitlyn Walker
The Villages®
![1723 BANBERRY RUN, THE VILLAGES, FL, 321..., The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
1723 BANBERRY RUN, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5097424 • FOUR STAR HOME BROKERS, INC., Darl...
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The Villages®
![17860 SE 89TH NATCHEZ AVE, THE VILLAGES,..., The Villages, FL 32162]()
3 beds
|2 baths
|1,625 sq ft
|House
17860 SE 89TH NATCHEZ AVE, THE VILLAGES,...
Community: The Villages®
MLS G5098361 • LPT REALTY, LLC, Marilyn Fletcher
Lake Ashton
![4025 SABLE LOOP DR, LAKE WALES, FL, 3385..., Lake Wales, FL 33859]()
4 beds
|3 baths
|2,923 sq ft
|House
4025 SABLE LOOP DR, LAKE WALES, FL, 3385...
Community: Lake Ashton
MLS P4937228 • A+ REALTY LLC, Michael Krigelski
Lake Ashton
![4168 ABERDEEN LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859]()
3 beds
|2 baths
|1,756 sq ft
|House
4168 ABERDEEN LN, LAKE WALES, FL, 33859
Community: Lake Ashton
MLS P4934058 • A+ REALTY LLC, Michael Krigelski
Lake Ashton
![5325 NICKLAUS DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884]()
2 beds
|2 baths
|1,319 sq ft
|House
5325 NICKLAUS DR, WINTER HAVEN, FL, 3388...
Community: Lake Ashton
MLS P4934140 • A+ REALTY LLC, Michael Krigelski
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.
Lakeside Landings
![10161 MAINSAIL DR, OXFORD, FL, 34484, Oxford, FL 34484]()
3 beds
|2 baths
|1,550 sq ft
|House
10161 MAINSAIL DR, OXFORD, FL, 34484
Community: Lakeside Landings
MLS G5105930 • LPT REALTY, LLC, Dave Monty
Lakes at Laurel Highlands
![2796 GRANDBURY GROVE RD, LAKELAND, FL, 3..., Lakeland, FL 33811]()
4 beds
|2 baths
|1,867 sq ft
|House
2796 GRANDBURY GROVE RD, LAKELAND, FL, 3...
Community: Lakes at Laurel Highlands
MLS L4958083 • XCELLENCE REALTY, INC, Yanery Pere...
Heritage Landings
![2796 GRANDBURY GROVE RD, LAKELAND, FL, 3..., Lakeland, FL 33811]()
4 beds
|2 baths
|1,867 sq ft
|House
2796 GRANDBURY GROVE RD, LAKELAND, FL, 3...
Community: Heritage Landings
MLS L4958083 • XCELLENCE REALTY, INC, Yanery Pere...
Sandpiper Golf & Country Club
![6325 EGRET DR, LAKELAND, FL, 33809, Lakeland, FL 33809]()
3 beds
|2 baths
|1,441 sq ft
|House
6325 EGRET DR, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS L4957052 • CLARK REALTY LLC, Steven Perkins
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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...
The Villages®
![912 ORCHID ST, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,144 sq ft
|Manufactured Home
912 ORCHID ST, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5104406 • REALTY EXECUTIVES IN THE VILLAGES,...
Cresswind at Victoria Gardens
![1677 VICTORIA GARDENS DR, DELAND, FL, 32..., Deland, FL 32724]()
3 beds
|2 baths
|1,512 sq ft
|House
1677 VICTORIA GARDENS DR, DELAND, FL, 32...
Community: Cresswind at Victoria Gardens
MLS O6331891 • SAND DOLLAR REALTY GROUP INC, Tamm...
The Villages®
![516 LOMA PASEO DR, THE VILLAGES, FL, 321..., The Villages, FL 32159]()
3 beds
|2 baths
|1,642 sq ft
|House
516 LOMA PASEO DR, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5098724 • COLDWELL BANKER VANGUARD LIFESTYLE...
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.
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
New
Kings Ridge
![3814 WESTERHAM DR, CLERMONT, FL, 34711, Clermont, FL 34711]()
2 beds
|2 baths
|1,422 sq ft
|House
3814 WESTERHAM DR, CLERMONT, FL, 34711
Community: Kings Ridge
MLS G5105624 • OLYMPUS EXECUTIVE REALTY INC, Mars...
New
Lake Ashton
![4081 DUNMORE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859]()
3 beds
|2 baths
|2,027 sq ft
|House
4081 DUNMORE DR, LAKE WALES, FL, 33859
Community: Lake Ashton
MLS S5141060 • MAZELG REALTY, Mary Sorrell
Stonecrest
![11041 SE 169TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,417 sq ft
|House
11041 SE 169TH PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
MLS G5105375 • REALTY EXECUTIVES IN THE VILLAGES,...
The Lakes at Harmony
![3184 SONGBIRD CIR, HARMONY, FL, 34773, Harmony, FL 34773]()
3 beds
|2 baths
|1,852 sq ft
|House
3184 SONGBIRD CIR, HARMONY, FL, 34773
Community: The Lakes at Harmony
MLS S5129784 • WEICHERT REALTORS HALLMARK PRO, Ba...
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The Villages®
![1415 LA HERMOSA DR, THE VILLAGES, FL, 32..., The Villages, FL 32162]()
2 beds
|2 baths
|1,495 sq ft
|House
1415 LA HERMOSA DR, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5105697 • BROKER ASSOCIATES REALTY, Christie...
The Villages®
![3753 COYNE LOOP, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|1,956 sq ft
|House
3753 COYNE LOOP, THE VILLAGES, FL, 32163
Community: The Villages®
MLS OM712313 • SALLY LOVE REAL ESTATE, Star Amado...
Compass Pointe
![958 DANVILLE CIR, MELBOURNE, FL, 32904, Melbourne, FL 32904]()
3 beds
|2 baths
|1,919 sq ft
|House
958 DANVILLE CIR, MELBOURNE, FL, 32904
Community: Compass Pointe
MLS 1056725 • Real Estate Direct of Florida, Davi...
Solivita
![572 SIENNA DR, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5128087 • BORCHINI REALTY, Dale Pautz
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
Stonecrest
![17652 SE 120TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|2 baths
|2,067 sq ft
|House
17652 SE 120TH TER, SUMMERFIELD, FL, 344...
Community: Stonecrest
MLS G5106211 • RE/MAX PREMIER REALTY LADY LK, Cin...
The Lakes at Harmony
![3168 SONGBIRD CIR, HARMONY, FL, 34773, Harmony, FL 34773]()
3 beds
|2 baths
|1,850 sq ft
|House
3168 SONGBIRD CIR, HARMONY, FL, 34773
Community: The Lakes at Harmony
MLS S5138968 • CORCORAN CONNECT LLC, Jeanine Corc...
Stonecrest
![17409 SE 111TH CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,700 sq ft
|House
17409 SE 111TH CIR, SUMMERFIELD, FL, 344...
Community: Stonecrest
MLS OM707769 • KELLER WILLIAMS CORNERSTONE RE, Ci...
Stonecrest
![17446 SE 115TH TERRACE RD, SUMMERFIELD, ..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,681 sq ft
|House
17446 SE 115TH TERRACE RD, SUMMERFIELD, ...
Community: Stonecrest
MLS OM706459 • KELLER WILLIAMS CORNERSTONE RE, Ri...
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Breakaway Trails
![94 SHADOWCREEK WAY, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|3,261 sq ft
|House
94 SHADOWCREEK WAY, ORMOND BEACH, FL, 32...
Community: Breakaway Trails
MLS 1218486 • Realty Pros Assured, Bill Navarra
Traditions at Lake Ruby
![2925 DAYTON DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884]()
3 beds
|2 baths
|2,109 sq ft
|House
2925 DAYTON DR, WINTER HAVEN, FL, 33884
Community: Traditions at Lake Ruby
MLS P4937324 • CENTURY 21 MYERS REALTY LAKE WALES...
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2,377
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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.
