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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
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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®
![133 OLANTA DR, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
133 OLANTA DR, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5103299 • REALTY EXECUTIVES IN THE VILLAGES,...
Arlington Ridge
![4671 SPRING GROVE LN, LEESBURG, FL, 3474..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,558 sq ft
|House
4671 SPRING GROVE LN, LEESBURG, FL, 3474...
Community: Arlington Ridge
MLS G5095980 • FLORIDA REALTY INVESTMENTS, Bonnie...
Royal Harbor
![5151 INDIAN OCEAN LOOP, TAVARES, FL, 327..., Tavares, FL 32778]()
4 beds
|2 baths
|2,091 sq ft
|House
5151 INDIAN OCEAN LOOP, TAVARES, FL, 327...
Community: Royal Harbor
MLS O6349567 • DAPORE REALTY INC, Diane Dapore Ro...
Venetian Bay
![3020 KING PALM DR, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168]()
4 beds
|3 baths
|2,179 sq ft
|House
3020 KING PALM DR, NEW SMYRNA BEACH, FL,...
Community: Venetian Bay
MLS NS1086490 • FLORIDA LIFE REAL ESTATE GROUP, S...
Solivita
![722 SHOREHAVEN DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5135961 • PELLEGO, LLC, Diane Cisek
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The Villages®
![752 MAYBANK LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
3 beds
|2 baths
|1,953 sq ft
|House
752 MAYBANK LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5099328 • RE/MAX PREMIER REALTY LADY LK, Mat...
Heritage Hills
![3574 LA JOLLA DR, CLERMONT, FL, 34711, Clermont, FL 34711]()
4 beds
|3 baths
|2,293 sq ft
|House
3574 LA JOLLA DR, CLERMONT, FL, 34711
Community: Heritage Hills
MLS O6316996 • ALFANO PROPERTY MANAGEMENT, Tae Ha...
Spruce Creek Country Club
![13729 SE 89TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,760 sq ft
|House
13729 SE 89TH AVE, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS A4646770 • NEW DOOR REAL ESTATE LLC, Alicia A...
The Villages®
![1161 DEL TORO DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|1,144 sq ft
|House
1161 DEL TORO DR, LADY LAKE, FL, 32159
Community: The Villages®
MLS OM713307 • KELLER WILLIAMS CORNERSTONE RE, St...
Sandpiper Golf & Country Club
![669 EAGLE RUN, LAKELAND, FL, 33809, Lakeland, FL 33809]()
2 beds
|2 baths
|1,321 sq ft
|House
669 EAGLE RUN, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS L4956387 • KELLER WILLIAMS REALTY SMART, Robi...
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.
Pelican Bay Daytona Beach
![257 GULL DR, DAYTONA BEACH, FL, 32119, Daytona Beach, FL 32119]()
2 beds
|2 baths
|1,900 sq ft
|House
257 GULL DR, DAYTONA BEACH, FL, 32119
Community: Pelican Bay Daytona Beach
MLS V4945791 • ADAMS, CAMERON & CO., REALTORS, Do...
Twin Lakes
![2717 GREENLANDS ST, SAINT CLOUD, FL, 347..., Saint Cloud, FL 34772]()
3 beds
|2 baths
|1,863 sq ft
|House
2717 GREENLANDS ST, SAINT CLOUD, FL, 347...
Community: Twin Lakes
MLS O6245416 • KELLER WILLIAMS WINTER PARK, Joana...
The Villages®
![732 PALMA DR, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,374 sq ft
|House
732 PALMA DR, THE VILLAGES, FL, 32159
Community: The Villages®
MLS O6319952 • REALTY HUB, Gordon Veling
Carillon Lakes
![4268 WINDCHIME LN, LAKELAND, FL, 33811, Lakeland, FL 33811]()
3 beds
|2 baths
|2,117 sq ft
|House
4268 WINDCHIME LN, LAKELAND, FL, 33811
Community: Carillon Lakes
MLS L4957151 • S & D REAL ESTATE SERVICE LLC, Mat...
The Villages®
![903 RAMOS DR, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
3 beds
|2 baths
|1,836 sq ft
|House
903 RAMOS DR, THE VILLAGES, FL, 32159
Community: The Villages®
MLS O6358859 • REALTY HUB, Gordon Veling
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Venetian Bay
![354 N AIRPORT RD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
2 beds
|3 baths
|1,837 sq ft
|Townhouse
354 N AIRPORT RD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS V4944616 • REALTY PROS ASSURED, James Brodick
Pelican Bay Daytona Beach
![256 PALM SPARROW CT, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119]()
2 beds
|2 baths
|1,146 sq ft
|Halfplex
256 PALM SPARROW CT, DAYTONA BEACH, FL, ...
Community: Pelican Bay Daytona Beach
MLS V4945783 • FLORIDA GLOBAL INT'L REALTY, Clara...
Trilogy® Orlando
![108 CRESCENT MOON DR, GROVELAND, FL, 347..., Groveland, FL 34736]()
3 beds
|2 baths
|1,974 sq ft
|House
108 CRESCENT MOON DR, GROVELAND, FL, 347...
Community: Trilogy® Orlando
MLS O6351834 • CHARLES RUTENBERG REALTY ORLANDO, ...
Grand Haven
![14 EGRET DR, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
MLS FC313955 • CHAD AND SANDY REAL ESTATE GRP, Ch...
Ridgehaven
![453 BROOKHAVEN TRL, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,791 sq ft
|House
453 BROOKHAVEN TRL, ORMOND BEACH, FL, 32...
Community: Ridgehaven
MLS O6323941 • MERITAGE HOMES OF FL REALTY, Tatia...
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.
Ridgehaven
![179 PARKHAVEN DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,572 sq ft
|House
179 PARKHAVEN DR, ORMOND BEACH, FL, 3217...
Community: Ridgehaven
MLS O6345925 • MERITAGE HOMES OF FL REALTY, Tatia...
Ridgehaven
![187 PARKHAVEN DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,454 sq ft
|House
187 PARKHAVEN DR, ORMOND BEACH, FL, 3217...
Community: Ridgehaven
MLS O6345911 • MERITAGE HOMES OF FL REALTY, Tatia...
High Vista at Ridgewood Lakes
![457 GOLF VISTA CIR, DAVENPORT, FL, 33837, Davenport, FL 33837]()
4 beds
|3 baths
|2,211 sq ft
|House
457 GOLF VISTA CIR, DAVENPORT, FL, 33837
Community: High Vista at Ridgewood Lakes
MLS O6330032 • VESTI LLC, Natalie Rivera
Four Seasons at Orlando
![2233 ANTILLES CLUB DR, KISSIMMEE, FL, 34..., Kissimmee, FL 34747]()
3 beds
|2 baths
|2,042 sq ft
|House
2233 ANTILLES CLUB DR, KISSIMMEE, FL, 34...
Community: Four Seasons at Orlando
MLS O6311232 • LA ROSA REALTY PREMIER LLC, Andres...
Pelican Bay Daytona Beach
![100 KILLDEER CT, DAYTONA BEACH, FL, 3211..., Daytona Beach, FL 32119]()
3 beds
|2 baths
|1,650 sq ft
|House
100 KILLDEER CT, DAYTONA BEACH, FL, 3211...
Community: Pelican Bay Daytona Beach
MLS 1216395 • EXP Realty LLC, Kevin Yarina
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Latitude Margaritaville
![182 ISLAND BREEZE AVE, DAYTONA BEACH, FL..., Daytona Beach, FL 32124]()
3 beds
|3 baths
|2,303 sq ft
|House
182 ISLAND BREEZE AVE, DAYTONA BEACH, FL...
Community: Latitude Margaritaville
MLS 1219506 • Realty Hub, Patricia Richardson
Plantation Bay Golf & Country Club
![945 STONE LAKE DR, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,910 sq ft
|House
945 STONE LAKE DR, ORMOND BEACH, FL, 321...
Community: Plantation Bay Golf & Country Club
MLS FC313035 • VENTURE DEVELOPMENT REALTY,INC, El...
Halifax Plantation
![3908 TANO DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
4 beds
|2 baths
|2,038 sq ft
|House
3908 TANO DR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
MLS FC313308 • COASTAL GATEWAY REAL ESTATE GROUP,...
Solivita
![702 TORREY PINES WAY, POINCIANA, FL, 347..., Poinciana, FL 34759]()
3 beds
|3 baths
|2,190 sq ft
|House
702 TORREY PINES WAY, POINCIANA, FL, 347...
Community: Solivita
MLS 2077347 • MARYKATE & CO REALTY, MARY KATHLEEN...
Archers Mill
![3357 ARCH AVE, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
4 beds
|2 baths
|2,034 sq ft
|House
3357 ARCH AVE, ORMOND BEACH, FL, 32174
Community: Archers Mill
MLS 1218945 • D R Horton Realty of Central Florid...
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.
Archers Mill
![3313 ARCH AVE, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,108 sq ft
|House
3313 ARCH AVE, ORMOND BEACH, FL, 32174
Community: Archers Mill
MLS O6339796 • DR HORTON REALTY OF CENTRAL FLORID...
Summer Trees
![127 CYPRESS POND RD, PORT ORANGE, FL, 32..., Port Orange, FL 32128]()
3 beds
|2 baths
|1,426 sq ft
|House
127 CYPRESS POND RD, PORT ORANGE, FL, 32...
Community: Summer Trees
MLS V4943112 • LPT REALTY, LLC, Ron Wysocarski
Solivita
![514 SAN JOAQUIN RD, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5138276 • FAIRWAY REALTY OF SOLIVITA, Elizab...
Ridgehaven
![1332 OAKHAVEN AVE, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
5 beds
|4 baths
|3,232 sq ft
|House
1332 OAKHAVEN AVE, ORMOND BEACH, FL, 321...
Community: Ridgehaven
MLS O6359264 • MERITAGE HOMES OF FL REALTY, Tatia...
Ridgehaven
![430 BROOKHAVEN TRL, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,487 sq ft
|House
430 BROOKHAVEN TRL, ORMOND BEACH, FL, 32...
Community: Ridgehaven
MLS O6359260 • MERITAGE HOMES OF FL REALTY, Tatia...
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Ridgehaven
![438 BROOKHAVEN TRL, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174]()
3 beds
|3 baths
|2,181 sq ft
|House
438 BROOKHAVEN TRL, ORMOND BEACH, FL, 32...
Community: Ridgehaven
MLS O6359262 • MERITAGE HOMES OF FL REALTY, Tatia...
Ridgehaven
![437 BROOKHAVEN TRL, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174]()
3 beds
|3 baths
|2,181 sq ft
|House
437 BROOKHAVEN TRL, ORMOND BEACH, FL, 32...
Community: Ridgehaven
MLS O6359263 • MERITAGE HOMES OF FL REALTY, Tatia...
Spruce Creek Country Club
![8865 SE 119TH ST, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
2 beds
|2 baths
|1,870 sq ft
|House
8865 SE 119TH ST, SUMMERFIELD, FL, 34491
Community: Spruce Creek Country Club
MLS G5104221 • RE/MAX PREMIER REALTY LADY LK, Rob...
Scottish Highlands
![1514 NEW ABBEY AVE, LEESBURG, FL, 34788, Leesburg, FL 34788]()
3 beds
|2 baths
|1,600 sq ft
|House
1514 NEW ABBEY AVE, LEESBURG, FL, 34788
Community: Scottish Highlands
MLS G5104143 • HOME WISE REALTY GROUP, INC., Wend...
Baytree
![512 JUNIPER WAY, TAVARES, FL, 32778, Tavares, FL 32778]()
MLS G5104072 • COLDWELL BANKER VANGUARD EDGE, Aly...
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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.
