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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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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 (2 reviews)
![Heritage Isle]()
$200Ks
- $500Ks
Heritage Isle, Viera, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2017
|
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
$300Ks
- $800Ks
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
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 (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 (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:
(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
- $600Ks
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®
![16894 SE 94TH SUNNYBROOK CIR, THE VILLAG..., The Villages, FL 32162]()
2 beds
|2 baths
|1,160 sq ft
|Villa
16894 SE 94TH SUNNYBROOK CIR, THE VILLAG...
Community: The Villages®
MLS G5102725 • FLORIDA FINE HOMES REALTY, LLC, Ji...
Solivita
![780 MYSTIC HILL CT, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS G5097240 • LA ROSA REALTY HORIZONS LLC, Sabin...
Scottish Highlands
![28 GORDON CT, LEESBURG, FL, 34788, Leesburg, FL 34788]()
2 beds
|2 baths
|1,374 sq ft
|House
28 GORDON CT, LEESBURG, FL, 34788
Community: Scottish Highlands
MLS OM699593 • COLDWELL BANKER VANGUARD EDGE, Val...
The Villages®
![1850 KYRLE TER, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|2,227 sq ft
|House
1850 KYRLE TER, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5103901 • REALTY EXECUTIVES IN THE VILLAGES,...
Indian River Colony Club
![1375 MAYFLOWER AVE, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|2 baths
|2,010 sq ft
|House
1375 MAYFLOWER AVE, MELBOURNE, FL, 32940
Community: Indian River Colony Club
MLS 1044056 • Four Star Real Estate LLC, Shellie ...
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Grand Isle
![1422 KEYS GATE DR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|2 baths
|2,011 sq ft
|House
1422 KEYS GATE DR, MELBOURNE, FL, 32940
Community: Grand Isle
MLS 1060491 • RE/MAX Aerospace Realty, Teresa Fer...
Kings Ridge
![2243 ADDISON AVE, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS G5102239 • OLYMPUS EXECUTIVE REALTY INC, Mars...
The Villages®
![7796 SE 168TH LONE OAK LOOP, THE VILLAGE..., The Villages, FL 32162]()
2 beds
|2 baths
|1,540 sq ft
|House
7796 SE 168TH LONE OAK LOOP, THE VILLAGE...
Community: The Villages®
MLS OM709769 • LPT REALTY, LLC, Gary Martin
The Villages®
![1613 CHERRY HILL RD, THE VILLAGES, FL, 3..., The Villages, FL 32159]()
2 beds
|2 baths
|1,357 sq ft
|House
1613 CHERRY HILL RD, THE VILLAGES, FL, 3...
Community: The Villages®
MLS G5092223 • FLORIDA FINE HOMES REALTY, LLC, Ca...
The Villages®
![1496 LIME GROVE LN, THE VILLAGES, FL, 32..., The Villages, FL 32162]()
2 beds
|2 baths
|1,132 sq ft
|Villa
1496 LIME GROVE LN, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5098536 • RE/MAX PREMIER REALTY LADY LK, Oli...
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.
Pennbrooke Fairways
![32805 OAK PARK DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,685 sq ft
|House
32805 OAK PARK DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS G5100425 • KELLER WILLIAMS ELITE PARTNERS III...
Plantation at Leesburg
![3529 MOUNT HOPE LOOP, LEESBURG, FL, 3474..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,723 sq ft
|House
3529 MOUNT HOPE LOOP, LEESBURG, FL, 3474...
Community: Plantation at Leesburg
MLS G5104687 • CENTURY 21 CARIOTI, Bonnie Valenti...
The Villages®
![901 CHULA CT, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,248 sq ft
|House
901 CHULA CT, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5092725 • FLORIDA FINE HOMES REALTY, LLC, Ca...
The Villages®
![870 TREVINO TER, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|1,087 sq ft
|Villa
870 TREVINO TER, LADY LAKE, FL, 32159
Community: The Villages®
MLS G5104646 • MORRIS REALTY AND INVESTMENTS, Kim...
Del Webb Sunbridge
![2479 PINE PRESERVE CT, SAINT CLOUD, FL, ..., Saint Cloud, FL 34771]()
4 beds
|2 baths
|2,054 sq ft
|House
2479 PINE PRESERVE CT, SAINT CLOUD, FL, ...
Community: Del Webb Sunbridge
MLS O6356573 • WEMERT GROUP REALTY LLC, Jenny Wem...
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Solivita
![1398 DEL MAR DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5137499 • BELLA VERDE REALTY LLC, Debra DiCi...
Spruce Creek Country Club
![13863 SE 85TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,844 sq ft
|House
13863 SE 85TH CIR, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS OM702632 • JUDY L. TROUT REALTY, Judy Trout
The Villages®
![482 HILDALGO DR, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
1 beds
|1 baths
|810 sq ft
|Villa
482 HILDALGO DR, THE VILLAGES, FL, 32159
Community: The Villages®
MLS O6276758 • REAL PROPERTY INTERNATIONAL, Bob L...
Del Webb Sunbridge
![6208 CITRUS GROVE CT, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34771]()
2 beds
|2 baths
|1,670 sq ft
|House
6208 CITRUS GROVE CT, SAINT CLOUD, FL, 3...
Community: Del Webb Sunbridge
MLS O6347383 • PULTE REALTY OF NORTH FLORIDA LLC,...
Del Webb Sunbridge
![6224 CITRUS GROVE CT, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34771]()
2 beds
|2 baths
|1,405 sq ft
|House
6224 CITRUS GROVE CT, SAINT CLOUD, FL, 3...
Community: Del Webb Sunbridge
MLS O6347520 • PULTE REALTY OF NORTH FLORIDA LLC,...
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.
Pennbrooke Fairways
![321 RANCHWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,894 sq ft
|House
321 RANCHWOOD DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS G5093172 • REAL BROKER, LLC, Mary Bell
The Villages®
![1008 LAREDO LN, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,268 sq ft
|House
1008 LAREDO LN, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5104370 • RE/MAX PREMIER REALTY LADY LK, Mat...
The Villages®
![17076 SE 96TH CHAPELWOOD CIR, THE VILLAG..., The Villages, FL 32162]()
3 beds
|2 baths
|1,265 sq ft
|House
17076 SE 96TH CHAPELWOOD CIR, THE VILLAG...
Community: The Villages®
MLS G5103450 • RE/MAX PREMIER REALTY LADY LK, Guy...
Arlington Ridge
![4436 ANTIETAM CREEK TRL, LEESBURG, FL, 3..., Leesburg, FL 34748]()
3 beds
|2 baths
|2,028 sq ft
|House
4436 ANTIETAM CREEK TRL, LEESBURG, FL, 3...
Community: Arlington Ridge
MLS G5103880 • ERA GRIZZARD REAL ESTATE, Misty No...
Solivita
![223 MONTEREY ST, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS O6361778 • VYLLA HOME, Manny Duran
Want to learn more about 55+ communities in Winter Park?
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(888) 625-4885
The Villages®
![7886 SE 167TH MISTWOOD LN, THE VILLAGES,..., The Villages, FL 32162]()
3 beds
|2 baths
|2,260 sq ft
|House
7886 SE 167TH MISTWOOD LN, THE VILLAGES,...
Community: The Villages®
MLS A4669943 • SAVVY AVENUE, LLC, Moe Mossa
The Villages®
![1999 KELMSCOTT ST, THE VILLAGES, FL, 321..., The Villages, FL 32162]()
2 beds
|2 baths
|1,156 sq ft
|Villa
1999 KELMSCOTT ST, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5100001 • RE/MAX PREMIER REALTY, Erica Jacob...
The Villages®
![1818 PUERTO BELLO DR, LADY LAKE, FL, 321..., Lady Lake, FL 32159]()
3 beds
|3 baths
|2,366 sq ft
|Villa
1818 PUERTO BELLO DR, LADY LAKE, FL, 321...
Community: The Villages®
MLS G5103245 • DOWN HOME REALTY, LLLP, Colleen A....
The Villages®
![3017 MOULTRIE WAY, THE VILLAGES, FL, 321..., The Villages, FL 32162]()
2 beds
|2 baths
|1,278 sq ft
|Villa
3017 MOULTRIE WAY, THE VILLAGES, FL, 321...
Community: The Villages®
MLS OM699954 • SELLSTATE SUPERIOR REALTY, Heather...
Heritage Hills
![3613 SOLANA CIR B, CLERMONT, FL, 34711, Clermont, FL 34711]()
2 beds
|2 baths
|1,374 sq ft
|Villa
3613 SOLANA CIR B, CLERMONT, FL, 34711
Community: Heritage Hills
MLS O6350552 • CREEGAN GROUP, David Johnston
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®
![971 MARGAUX TRL, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,156 sq ft
|House
971 MARGAUX TRL, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5096444 • RE/MAX PREMIER REALTY LADY LK, Oli...
Venetian Bay
![3615 MARISOL CT, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168]()
3 beds
|2 baths
|1,764 sq ft
|House
3615 MARISOL CT, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
MLS FC309965 • COLDWELL BANKER PREMIER, John Corb...
The Country Club of Mount Dora
![8012 SAINT JAMES WAY, MOUNT DORA, FL, 32..., Mount Dora, FL 32757]()
3 beds
|2 baths
|2,062 sq ft
|House
8012 SAINT JAMES WAY, MOUNT DORA, FL, 32...
Community: The Country Club of Mount Dora
MLS G5100747 • RE/MAX PREMIER REALTY, Holly A. Fa...
Del Webb at Viera
![3132 TIDEPOOL PL, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|2 baths
|1,902 sq ft
|House
3132 TIDEPOOL PL, MELBOURNE, FL, 32940
Community: Del Webb at Viera
MLS 1059263 • Engel&Voelkers Melb Beachside, Marc...
Pelican Bay Daytona Beach
![150 BLUE HERON DR B, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119]()
3 beds
|2 baths
|1,365 sq ft
|Condo
150 BLUE HERON DR B, DAYTONA BEACH, FL, ...
Community: Pelican Bay Daytona Beach
MLS 1217166 • EXP Realty LLC, Debbie Ellis
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Halifax Plantation
![3413 REXFORD CIR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,924 sq ft
|House
3413 REXFORD CIR, ORMOND BEACH, FL, 3217...
Community: Halifax Plantation
MLS O6332412 • PREMIER SOTHEBYS INTL REALTY, Rach...
Indian River Colony Club
![1290 MAYFLOWER AVE, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
2 beds
|2 baths
|1,616 sq ft
|House
1290 MAYFLOWER AVE, MELBOURNE, FL, 32940
Community: Indian River Colony Club
MLS 1062414 • Four Star Real Estate LLC, Shellie ...
Del Webb Sunbridge
![2973 CHERRY BLOSSOM LOOP, SAINT CLOUD, F..., Saint Cloud, FL 34771]()
2 beds
|2 baths
|1,584 sq ft
|Villa
2973 CHERRY BLOSSOM LOOP, SAINT CLOUD, F...
Community: Del Webb Sunbridge
MLS S5138111 • ORLANDO REGIONAL REALTY, Heike Kna...
The Villages®
![2282 SHEEHAN ST, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
2 beds
|2 baths
|1,227 sq ft
|Villa
2282 SHEEHAN ST, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5104320 • ATLAS CENTRAL FLORIDA REALTY, Mich...
The Villages®
![1705 BETRILLO CT, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
3 beds
|2 baths
|1,210 sq ft
|House
1705 BETRILLO CT, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS O6299502 • LPT REALTY, LLC, Claudia Montes
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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.
