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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:
(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
Latitude Margaritaville
![154 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,308 sq ft
|House
154 GYPSY PALACE LN, DAYTONA BEACH, FL, ...
Community: Latitude Margaritaville
MLS 1217405 • Fathom Realty FL LLC, Adrienne Smit...
The Villages®
![5778 HENRY LOOP, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|1,531 sq ft
|House
5778 HENRY LOOP, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5098983 • DENIZ REALTY PARTNERS LLC, Ashley ...
Solivita
![448 SORRENTO RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS TB8395602 • KELLER WILLIAMS SUBURBAN TAMPA, T...
Venetian Bay
![3446 PONETA AVE, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|2,103 sq ft
|House
3446 PONETA AVE, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
MLS 1218418 • Keller Williams Realty Florida Part...
Halifax Plantation
![2889 MONAGHAN DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
3 beds
|3 baths
|2,040 sq ft
|House
2889 MONAGHAN DR, ORMOND BEACH, FL, 3217...
Community: Halifax Plantation
MLS FC313007 • BERKSHIRE HATHAWAY HOMESERVICE, Le...
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Del Webb Sunbridge
![6320 TRAILBLAZE BND, SAINT CLOUD, FL, 34..., Saint Cloud, FL 34771]()
4 beds
|3 baths
|2,249 sq ft
|House
6320 TRAILBLAZE BND, SAINT CLOUD, FL, 34...
Community: Del Webb Sunbridge
MLS O6329820 • XCELLENCE REALTY INC., Dan Dinozzi
Highland Fairways
![1967 LONG BOAT DR, LAKELAND, FL, 33810, Lakeland, FL 33810]()
2 beds
|2 baths
|1,955 sq ft
|House
1967 LONG BOAT DR, LAKELAND, FL, 33810
Community: Highland Fairways
MLS U8253025 • FUTURE HOME REALTY INC, Frank Poll...
Solivita
![1388 LOMBARDI CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS O6319738 • EPIC FLORIDA REALTY LLC, Amanda Na...
The Villages®
![5087 NE 121ST AVE, OXFORD, FL, 34484, Oxford, FL 34484]()
3 beds
|2 baths
|1,839 sq ft
|House
5087 NE 121ST AVE, OXFORD, FL, 34484
Community: The Villages®
MLS G5100497 • RE/MAX PREMIER REALTY LADY LK, Ger...
Venetian Bay
![3039 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|1,672 sq ft
|House
3039 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS O6308215 • ATKINS REALTY GROUP, Larry Atkins
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®
![471 GASKIN LN, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,732 sq ft
|House
471 GASKIN LN, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5099812 • MORRIS REALTY AND INVESTMENTS, Sco...
Lake Ashton
![6301 PINEHURST LOOP, WINTER HAVEN, FL, 3..., Winter Haven, FL 33884]()
3 beds
|2 baths
|2,057 sq ft
|House
6301 PINEHURST LOOP, WINTER HAVEN, FL, 3...
Community: Lake Ashton
MLS P4936452 • GLOBAL LIFESTYLE LLC, Brad Kirwan
Latitude Margaritaville
![443 GOOD LIFE WAY, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124]()
3 beds
|2 baths
|1,563 sq ft
|House
443 GOOD LIFE WAY, DAYTONA BEACH, FL, 32...
Community: Latitude Margaritaville
MLS 1211061 • Bob Hodges and Sons Realty, Susan W...
Scottish Highlands
![918 DUNDEE CIR, LEESBURG, FL, 34788, Leesburg, FL 34788]()
2 beds
|2 baths
|1,380 sq ft
|House
918 DUNDEE CIR, LEESBURG, FL, 34788
Community: Scottish Highlands
MLS O6346328 • WRA BUSINESS & REAL ESTATE, Andrea...
Venetian Bay
![3611 MARISOL CT, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168]()
3 beds
|2 baths
|1,712 sq ft
|House
3611 MARISOL CT, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
MLS NS1084192 • THE KEYES COMPANY, Deborah Drew M...
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Plantation Bay Golf & Country Club
![1127 HANSBERRY CT, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
2 beds
|2 baths
|1,308 sq ft
|Townhouse
1127 HANSBERRY CT, ORMOND BEACH, FL, 321...
Community: Plantation Bay Golf & Country Club
MLS FC308929 • VENTURE DEVELOPMENT REALTY,INC, De...
Harbor Hills Country Club
![6042 TOPSAIL RD, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
3 beds
|2 baths
|2,190 sq ft
|House
6042 TOPSAIL RD, LADY LAKE, FL, 32159
Community: Harbor Hills Country Club
MLS OM688631 • NEXT GENERATION REALTY OF MARION C...
Pennbrooke Fairways
![910 EAGLES LNDG, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,807 sq ft
|House
910 EAGLES LNDG, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS G5095291 • MAXREV LLC, Jayne Marvin
Del Webb Sunbridge
![6375 TRAILBLAZE BND, SAINT CLOUD, FL, 34..., Saint Cloud, FL 34771]()
4 beds
|4 baths
|2,781 sq ft
|House
6375 TRAILBLAZE BND, SAINT CLOUD, FL, 34...
Community: Del Webb Sunbridge
MLS O6347477 • LPT REALTY, LLC, Manuel Delgado
Solivita
![1062 UMBRIA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS O6336786 • FLORIDA PLUS REALTY, LLC, Sarah Bo...
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.
Solivita
![504 GRAND CANAL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5135090 • PELLEGO, LLC, Diane Cisek
Trilogy® Orlando
![373 ALCOVE DR, GROVELAND, FL, 34736, Groveland, FL 34736]()
2 beds
|2 baths
|1,579 sq ft
|House
373 ALCOVE DR, GROVELAND, FL, 34736
Community: Trilogy® Orlando
MLS G5102461 • COMMUNITY ELITE REALTY, Nancy Aitk...
Trilogy® Orlando
![277 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736]()
3 beds
|2 baths
|1,839 sq ft
|House
277 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
MLS G5102140 • COMMUNITY ELITE REALTY, Nancy Aitk...
Spruce Creek South
![9802 SE 178TH LN, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
3 beds
|2 baths
|1,450 sq ft
|House
9802 SE 178TH LN, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
MLS OM692230 • KELLER WILLIAMS CORNERSTONE RE, Ri...
The Villages®
![7706 COUNTY ROAD 109D, LADY LAKE, FL, 32..., Lady Lake, FL 32159]()
3 beds
|2 baths
|2,128 sq ft
|Manufactured Home
7706 COUNTY ROAD 109D, LADY LAKE, FL, 32...
Community: The Villages®
MLS OM705213 • ENGEL & VOLKERS OCALA, Jodi Molzof
Want to learn more about 55+ communities in Winter Park?
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Solivita
![1390 HARBOR RIDGE DR, KISSIMMEE, FL, 347..., Kissimmee, FL 34759]()
2 beds
|2 baths
|1,703 sq ft
|House
1390 HARBOR RIDGE DR, KISSIMMEE, FL, 347...
Community: Solivita
MLS O6294709 • AGENT TRUST REALTY CORPORATION, Gr...
Solivita
![502 MONTEREY ST, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5123661 • PELLEGO, LLC, Paul Maiatico
Spruce Creek South
![17835 SE 95TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,158 sq ft
|House
17835 SE 95TH CIR, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
MLS OM704375 • MEADOWS REALTY, LLC, Bert Meadows
Twin Lakes
![2666 MEADOWEDGE LOOP, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772]()
4 beds
|3 baths
|2,935 sq ft
|House
2666 MEADOWEDGE LOOP, SAINT CLOUD, FL, 3...
Community: Twin Lakes
MLS G5097478 • KELLER WILLIAMS ELITE PARTNERS III...
Del Webb Sunbridge
![3130 VANGUARD CT, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771]()
4 beds
|4 baths
|3,000 sq ft
|House
3130 VANGUARD CT, SAINT CLOUD, FL, 34771
Community: Del Webb Sunbridge
MLS O6345433 • EXP REALTY LLC, Stephany Cornelius
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.
Latitude Margaritaville
![867 BAMA BREEZE DR, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124]()
2 beds
|3 baths
|1,748 sq ft
|Villa
867 BAMA BREEZE DR, DAYTONA BEACH, FL, 3...
Community: Latitude Margaritaville
MLS O6308920 • PREMIER SOTHEBYS INT'L REALTY, Deb...
Lake Ashton
![4432 WATERFORD DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859]()
2 beds
|2 baths
|1,605 sq ft
|House
4432 WATERFORD DR, LAKE WALES, FL, 33859
Community: Lake Ashton
MLS P4931651 • CENTURY 21 MYERS REALTY LAKE WALES...
Cresswind at Victoria Gardens
![161 OLD MOSS CIR, DELAND, FL, 32724, Deland, FL 32724]()
2 beds
|2 baths
|1,510 sq ft
|House
161 OLD MOSS CIR, DELAND, FL, 32724
Community: Cresswind at Victoria Gardens
MLS O6331123 • THE C SMITH REAL ESTATE GROUP LLC,...
High Vista at Ridgewood Lakes
![322 HIGH VISTA DR, DAVENPORT, FL, 33837, Davenport, FL 33837]()
3 beds
|2 baths
|1,776 sq ft
|House
322 HIGH VISTA DR, DAVENPORT, FL, 33837
Community: High Vista at Ridgewood Lakes
MLS O6327698 • CHARLES RUTENBERG REALTY ORLANDO, ...
Pennbrooke Fairways
![543 COTTAGE PARK LN, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|1 baths
|788 sq ft
|House
543 COTTAGE PARK LN, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS G5102481 • CENTURY 21 MYERS REALTY, Lisa Wolf...
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Kings Ridge
![3416 CAPLAND AVE, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS G5098813 • RE/MAX TITANIUM GROUP, Kimberly Jo...
Stonecrest
![11246 SE 175TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,312 sq ft
|House
11246 SE 175TH LN, SUMMERFIELD, FL, 3449...
Community: Stonecrest
MLS G5102326 • CHARLES RUTENBERG REALTY ORLANDO, ...
Solivita
![3775 VIA MAZZINI CT, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759]()
4 beds
|3 baths
|2,495 sq ft
|House
3775 VIA MAZZINI CT, KISSIMMEE, FL, 3475...
Community: Solivita
MLS S5134048 • BORCHINI REALTY, Cherie Pontes
Twin Lakes
![2410 DATURA LOOP, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772]()
2 beds
|2 baths
|1,464 sq ft
|Villa
2410 DATURA LOOP, SAINT CLOUD, FL, 34772
Community: Twin Lakes
MLS S5103150 • COLDWELL BANKER SOLOMON, Susy Orti...
Indian River Colony Club
![1531 INDEPENDENCE AVE, MELBOURNE, FL, 32..., Melbourne, FL 32940]()
2 beds
|2 baths
|1,642 sq ft
|House
1531 INDEPENDENCE AVE, MELBOURNE, FL, 32...
Community: Indian River Colony Club
MLS 1024983 • Four Star Real Estate LLC, Robin St...
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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.
