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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
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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
Twin Lakes
![2585 YELLOW BRICK RD, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772]()
2 beds
|2 baths
|1,464 sq ft
|Villa
2585 YELLOW BRICK RD, SAINT CLOUD, FL, 3...
Community: Twin Lakes
MLS O6343239 • EXP REALTY LLC, Dawn Grigsby
Heritage Hills
![4016 SERENA LN, CLERMONT, FL, 34711, Clermont, FL 34711]()
3 beds
|2 baths
|2,130 sq ft
|House
4016 SERENA LN, CLERMONT, FL, 34711
Community: Heritage Hills
MLS O6346624 • BHHS FLORIDA REALTY, Patti Kincaid
Colonnades
![1690 COLONNADES CIR, LAKELAND, FL, 33811, Lakeland, FL 33811]()
2 beds
|2 baths
|1,317 sq ft
|House
1690 COLONNADES CIR, LAKELAND, FL, 33811
Community: Colonnades
MLS A4669314 • S & D REAL ESTATE SERVICE LLC, Jas...
Indian River Colony Club
![1444 PATRIOT DR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|2 baths
|1,874 sq ft
|House
1444 PATRIOT DR, MELBOURNE, FL, 32940
Community: Indian River Colony Club
MLS 1046589 • Four Star Real Estate LLC, Shellie ...
Summit Greens
![993 EVEREST ST, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS S5121766 • CENTURY 21 WOLF'S CROSSING REALTY,...
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(888) 625-4885
The Lakes at Harmony
![3388 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773]()
3 beds
|3 baths
|1,918 sq ft
|House
3388 SAGEBRUSH ST, HARMONY, FL, 34773
Community: The Lakes at Harmony
MLS O6351645 • RESORT REALTY GROUP LTD INC, David...
Solivita
![1294 HARBOR RIDGE DR, KISSIMMEE, FL, 347..., Kissimmee, FL 34759]()
3 beds
|2 baths
|1,590 sq ft
|House
1294 HARBOR RIDGE DR, KISSIMMEE, FL, 347...
Community: Solivita
MLS S5133570 • PELLEGO, LLC, Stan Wilson
Plantation Bay Golf & Country Club
![51 BAY POINTE DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,996 sq ft
|House
51 BAY POINTE DR, ORMOND BEACH, FL, 3217...
Community: Plantation Bay Golf & Country Club
MLS 1209215 • Realty Evolution Inc, Marsha Thayer
The Villages®
![804 MAPLE LN, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|944 sq ft
|Manufactured Home
804 MAPLE LN, LADY LAKE, FL, 32159
Community: The Villages®
MLS R4909508 • BLACK TIE REAL ESTATE PROFESSIONAL...
Kings Ridge
![2289 TWICKINGHAM CT, CLERMONT, FL, 34711, Clermont, FL 34711]()
3 beds
|2 baths
|2,154 sq ft
|House
2289 TWICKINGHAM CT, CLERMONT, FL, 34711
Community: Kings Ridge
MLS O6348882 • KELLER WILLIAMS WINTER PARK, Gale ...
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
![11094 SE 173RD LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,717 sq ft
|House
11094 SE 173RD LN, SUMMERFIELD, FL, 3449...
Community: Stonecrest
MLS V4942531 • RE/MAX SIGNATURE, Stephanie Cathey
Arlington Ridge
![4347 ARLINGTON RIDGE BLVD, LEESBURG, FL,..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,704 sq ft
|House
4347 ARLINGTON RIDGE BLVD, LEESBURG, FL,...
Community: Arlington Ridge
MLS G5096101 • LOKATION, Steven Simpkins
Pennbrooke Fairways
![127 WESTWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,086 sq ft
|Manufactured Home
127 WESTWOOD DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS G5103254 • ERA GRIZZARD REAL ESTATE, Ricky Ha...
Heritage Hills
![3791 SANIBEL ST, CLERMONT, FL, 34711, Clermont, FL 34711]()
3 beds
|3 baths
|2,615 sq ft
|House
3791 SANIBEL ST, CLERMONT, FL, 34711
Community: Heritage Hills
MLS G5103629 • KELLER WILLIAMS ELITE PARTNERS III...
The Villages®
![3167 SPANISH MOSS WAY, THE VILLAGES, FL,..., The Villages, FL 32163]()
3 beds
|2 baths
|1,569 sq ft
|House
3167 SPANISH MOSS WAY, THE VILLAGES, FL,...
Community: The Villages®
MLS G5103472 • COLDWELL BANKER STEVENS RE, Jeremy...
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The Villages®
![5180 LEXINGTON CIR, WILDWOOD, FL, 34785, Wildwood, FL 34785]()
3 beds
|2 baths
|1,932 sq ft
|Manufactured Home
5180 LEXINGTON CIR, WILDWOOD, FL, 34785
Community: The Villages®
MLS O6355865 • SAND DOLLAR REALTY GROUP INC, Robe...
Lake Ashton
![4028 BIRKDALE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859]()
3 beds
|2 baths
|1,706 sq ft
|House
4028 BIRKDALE DR, LAKE WALES, FL, 33859
Community: Lake Ashton
MLS P4936811 • LAKE ASHTON REALTY INC., Lori Raat...
Plantation Bay Golf & Country Club
![5 JASMINE RUN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
2 beds
|2 baths
|1,386 sq ft
|House
5 JASMINE RUN, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS FC311584 • CLAIRE HUNTER REALTY, Brian Hunter
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
VillageWalk at Lake Nona
![12026 AUTUMN FERN LN, ORLANDO, FL, 32827, Orlando, FL 32827]()
3 beds
|3 baths
|3,015 sq ft
|House
12026 AUTUMN FERN LN, ORLANDO, FL, 32827
Community: VillageWalk at Lake Nona
MLS O6331700 • RATIO REAL ESTATE, LLC, Veronica L...
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.
Arlington Ridge
![27106 CAMERONS RUN, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|2,436 sq ft
|House
27106 CAMERONS RUN, LEESBURG, FL, 34748
Community: Arlington Ridge
MLS O6343489 • LPT REALTY, LLC, Raymond Reyes
Solivita
![644 SHOREHAVEN DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5124905 • BELLA VERDE REALTY LLC, Debra DiCi...
Plantation Bay Golf & Country Club
![21 JASMINE RUN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
2 beds
|2 baths
|1,424 sq ft
|House
21 JASMINE RUN, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS 1216701 • Venture Development Realty, Inc, Sc...
Highland Lakes
![5618 ROSEWALL CIR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,306 sq ft
|House
5618 ROSEWALL CIR, LEESBURG, FL, 34748
Community: Highland Lakes
MLS G5096926 • SCATES REALTY & INVESTMENT PRO, Ei...
Lakes at Laurel Highlands
![1823 PRISTINE LOOP, LAKELAND, FL, 33811, Lakeland, FL 33811]()
3 beds
|2 baths
|1,711 sq ft
|House
1823 PRISTINE LOOP, LAKELAND, FL, 33811
Community: Lakes at Laurel Highlands
MLS T3520599 • CENTURY 21 ROSA LEON, Maribel Calz...
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Latitude Margaritaville
![640 MARGARITAVILLE AVE, DAYTONA BEACH, F..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,563 sq ft
|House
640 MARGARITAVILLE AVE, DAYTONA BEACH, F...
Community: Latitude Margaritaville
MLS 1218325 • Bob Hodges and Sons Realty, Kelley ...
Grand Haven
![19 LAKEVIEW LN, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
MLS FC311591 • EXP REALTY LLC, TERRY HOOKER
Spruce Creek South
![17937 SE 107TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,450 sq ft
|House
17937 SE 107TH TER, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
MLS G5093275 • IM REALTY, Ira Miller
Grand Haven
![37 W WATERSIDE PKWY, PALM COAST, FL, 321..., Palm Coast, FL 32137]()
2 beds
|2 baths
|2,254 sq ft
|House
37 W WATERSIDE PKWY, PALM COAST, FL, 321...
Community: Grand Haven
MLS 1215411 • Serenity Realty Group, Edward Lang
Harbor Hills Country Club
![39517 HILLRISE LN, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
4 beds
|3 baths
|2,532 sq ft
|House
39517 HILLRISE LN, LADY LAKE, FL, 32159
Community: Harbor Hills Country Club
MLS G5103664 • MORRIS REALTY AND INVESTMENTS, Cra...
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
![11037 SE 173RD PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,328 sq ft
|House
11037 SE 173RD PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
MLS G5102718 • RE/MAX FOXFIRE - SUMMERFIELD, Donn...
Colonnades
![4926 PLEASANT HOLLOW TRL, LAKELAND, FL, ..., Lakeland, FL 33811]()
2 beds
|2 baths
|1,193 sq ft
|House
4926 PLEASANT HOLLOW TRL, LAKELAND, FL, ...
Community: Colonnades
MLS L4953532 • COLDWELL BANKER REALTY, Lisa Broch...
The Villages®
![14202 SANDALWOOD DR # 202, WILDWOOD, FL,..., Wildwood, FL 34785]()
2 beds
|2 baths
|1,085 sq ft
|Condo
14202 SANDALWOOD DR # 202, WILDWOOD, FL,...
Community: The Villages®
MLS G5101963 • MORRIS REALTY AND INVESTMENTS, The...
Four Seasons at Orlando
![1987 KEY BAY TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747]()
2 beds
|2 baths
|1,437 sq ft
|Villa
1987 KEY BAY TRL, KISSIMMEE, FL, 34747
Community: Four Seasons at Orlando
MLS O6270026 • KELLER WILLIAMS ADVANTAGE III, Nat...
Latitude Margaritaville
![378 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,464 sq ft
|House
378 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...
Community: Latitude Margaritaville
MLS 1215209 • Bob Hodges and Sons Realty, Sandra ...
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Solivita
![300 FALLING WATER DR, POINCIANA, FL, 347..., Poinciana, FL 34759]()
2 beds
|2 baths
|1,171 sq ft
|Halfplex
300 FALLING WATER DR, POINCIANA, FL, 347...
Community: Solivita
MLS S5123200 • BELLA VERDE REALTY LLC, Miguel Elv...
Venetian Bay
![424 LUNA BELLA LN 422, NEW SMYRNA BEACH,..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|1,953 sq ft
|Condo
424 LUNA BELLA LN 422, NEW SMYRNA BEACH,...
Community: Venetian Bay
MLS NS1086308 • EXIT REAL ESTATE PROPERTY SOL, Ca...
Highland Lakes
![5500 LAVER ST, LEESBURG, FL, 34748, Leesburg, FL 34748]()
MLS G5096531 • FLORIDA PLUS REALTY, LLC, Christin...
Lake Ashton
![4568 TURNBERRY LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859]()
3 beds
|2 baths
|1,847 sq ft
|House
4568 TURNBERRY LN, LAKE WALES, FL, 33859
Community: Lake Ashton
MLS P4936702 • GLOBAL LIFESTYLE LLC, Brad Kirwan
Venetian Bay
![3056 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168]()
3 beds
|4 baths
|1,847 sq ft
|Townhouse
3056 ISLES WAY, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
MLS NS1086283 • EXIT REAL ESTATE PROPERTY SOL, Ca...
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2,487
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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.
