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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:
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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
- $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
Solivita
![1309 LOMBARDI CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5129926 • PELLEGO, LLC, Claudia Gimenez-Carl...
Solivita
![243 NEW RIVER DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5135378 • BELLA VERDE REALTY LLC, Miguel Elv...
Summer Trees
![71 CROOKED PINE RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128]()
2 beds
|2 baths
|1,415 sq ft
|Townhouse
71 CROOKED PINE RD, PORT ORANGE, FL, 321...
Community: Summer Trees
MLS V4943055 • LPT REALTY LLC, Farrah Thacker
Plantation Bay Golf & Country Club
![4 JASMINE RUN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
2 beds
|2 baths
|2,037 sq ft
|House
4 JASMINE RUN, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS FC311404 • ONE SOTHEBYS INTERNATIONAL, Kory L...
The Villages®
![2530 SAFFRON LN, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,512 sq ft
|House
2530 SAFFRON LN, THE VILLAGES, FL, 32162
Community: The Villages®
MLS O6269489 • BEST HOMES, LLC., Harry D'Onofrio
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Solivita
![1329 DEL MAR DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5131377 • PELLEGO, LLC, Stan Wilson
Lakes of Mount Dora
![2440 PAWTUCKET PASS, MOUNT DORA, FL, 327..., Mount Dora, FL 32757]()
2 beds
|2 baths
|2,663 sq ft
|House
2440 PAWTUCKET PASS, MOUNT DORA, FL, 327...
Community: Lakes of Mount Dora
MLS O6320399 • REALTY HUB, Steven Amowitz PA
The Villages®
![1639 CAMPOS DR, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,121 sq ft
|Villa
1639 CAMPOS DR, THE VILLAGES, FL, 32162
Community: The Villages®
MLS O6333604 • REDFIN CORPORATION, Jo Holton
Trilogy® Orlando
![119 CRESCENT MOON DR, GROVELAND, FL, 347..., Groveland, FL 34736]()
2 beds
|2 baths
|1,556 sq ft
|House
119 CRESCENT MOON DR, GROVELAND, FL, 347...
Community: Trilogy® Orlando
MLS G5088807 • WEICHERT, REALTORS-HALLMARK PR, Br...
Spruce Creek Country Club
![9290 SE 120TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|2 baths
|2,126 sq ft
|House
9290 SE 120TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek Country Club
MLS OM698604 • SELLSTATE NGR- SUMMERFIELD, Virgil...
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
![309 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,205 sq ft
|Villa
309 GYPSY PALACE LN, DAYTONA BEACH, FL, ...
Community: Latitude Margaritaville
MLS TB8424426 • REDFIN CORPORATION, Valerie Gatzk...
Venetian Bay
![461 LUNA BELLA LN, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168]()
3 beds
|2 baths
|2,002 sq ft
|House
461 LUNA BELLA LN, NEW SMYRNA BEACH, FL,...
Community: Venetian Bay
MLS NS1085187 • WATSON REALTY CORP, Lainy McKain
Spruce Creek Country Club
![13751 SE 88TH CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
2 beds
|2 baths
|1,364 sq ft
|House
13751 SE 88TH CT, SUMMERFIELD, FL, 34491
Community: Spruce Creek Country Club
MLS OM696340 • RE/MAX FOXFIRE - SUMMERFIELD, Caro...
Stonecrest
![17645 SE 117TH CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|3 baths
|1,686 sq ft
|House
17645 SE 117TH CIR, SUMMERFIELD, FL, 344...
Community: Stonecrest
MLS OM698674 • ROBB HARRISON REALTY INC, Robb Har...
Solivita
![2285 PALM TREE DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5119372 • ARISTA REALTY GROUP, LLC, Steve Lo...
Want to learn more about 55+ communities in Winter Park?
55places can help!
Questions? Call us:
(888) 625-4885
Grand Isle
![1634 TIMACUAN DR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
MLS 1048020 • RE/MAX Elite, Deborah L Tomczak
Royal Highlands
![5401 ESSEX CT, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|3 baths
|2,009 sq ft
|House
5401 ESSEX CT, LEESBURG, FL, 34748
Community: Royal Highlands
MLS G5102657 • BONJORN REAL ESTATE, Pamela Bonjor...
Four Seasons at Orlando
![1890 FLORA PASS PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747]()
2 beds
|2 baths
|1,557 sq ft
|Villa
1890 FLORA PASS PL, KISSIMMEE, FL, 34747
Community: Four Seasons at Orlando
MLS TB8392113 • COMPASS FLORIDA LLC, Stella Sheri...
The Villages®
![491 HARLOW LN, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|1,958 sq ft
|House
491 HARLOW LN, THE VILLAGES, FL, 32163
Community: The Villages®
MLS OM708408 • ASHLEY YATES REALTY, Danielle Smit...
Solivita
![573 DAVINCI PASS, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5134315 • FLORIDA PROPERTY HOMES, Israel Tor...
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 Lakes at Harmony
![7529 CASTLEWOOD CT, HARMONY, FL, 34773, Harmony, FL 34773]()
3 beds
|2 baths
|1,852 sq ft
|House
7529 CASTLEWOOD CT, HARMONY, FL, 34773
Community: The Lakes at Harmony
MLS O6346626 • EXP REALTY LLC, Kristy Cook
The Villages®
![411 DEL MAR DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
3 beds
|2 baths
|1,730 sq ft
|House
411 DEL MAR DR, LADY LAKE, FL, 32159
Community: The Villages®
MLS O6337392 • HOUWZER INC, Daniel Robinson
Twin Lakes
![5043 VANTAGE CT, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772]()
3 beds
|3 baths
|2,365 sq ft
|House
5043 VANTAGE CT, SAINT CLOUD, FL, 34772
Community: Twin Lakes
MLS S5117701 • WEICHERT REALTORS HALLMARK PRO, Sh...
Halifax Plantation
![1510 KINNARD DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,695 sq ft
|Townhouse
1510 KINNARD DR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
MLS FC306681 • VENTURE DEVELOPMENT REALTY,INC, El...
Plantation Bay Golf & Country Club
![998 DOWNSHIRE LN, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
5 beds
|4 baths
|5,454 sq ft
|House
998 DOWNSHIRE LN, ORMOND BEACH, FL, 3217...
Community: Plantation Bay Golf & Country Club
MLS FC312940 • VENTURE DEVELOPMENT REALTY,INC, El...
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Plantation at Leesburg
![4949 SAWGRASS LAKE CIR, LEESBURG, FL, 34..., Leesburg, FL 34748]()
3 beds
|3 baths
|2,133 sq ft
|House
4949 SAWGRASS LAKE CIR, LEESBURG, FL, 34...
Community: Plantation at Leesburg
MLS G5102655 • CENTURY 21 MYERS REALTY, Mary Jane...
Latitude Margaritaville
![253 COMPASS ROSE DR, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124]()
2 beds
|3 baths
|2,067 sq ft
|House
253 COMPASS ROSE DR, DAYTONA BEACH, FL, ...
Community: Latitude Margaritaville
MLS V4945061 • RE/MAX SIGNATURE, Janet Fuller
Ridgehaven
![181 PARKHAVEN DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,454 sq ft
|House
181 PARKHAVEN DR, ORMOND BEACH, FL, 3217...
Community: Ridgehaven
MLS O6345928 • MERITAGE HOMES OF FL REALTY, Tatia...
Venetian Bay
![440 VENETIAN PALMS BLVD, NEW SMYRNA BEAC..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|1,779 sq ft
|House
440 VENETIAN PALMS BLVD, NEW SMYRNA BEAC...
Community: Venetian Bay
MLS O6342352 • TOPSKY REALTY INC, Sammi Li
Twin Lakes
![2419 DATURA LOOP, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772]()
2 beds
|2 baths
|1,261 sq ft
|Villa
2419 DATURA LOOP, SAINT CLOUD, FL, 34772
Community: Twin Lakes
MLS S5130508 • CENTURY 21 EDGE, Juan Hidalgo
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®
![3441 POSSEHL PL, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
2 beds
|2 baths
|1,148 sq ft
|Villa
3441 POSSEHL PL, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5094216 • FLORIDA REALTY INVESTMENTS, Robyn ...
Plantation Bay Golf & Country Club
![920 BROOKRIDGE LN, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,627 sq ft
|House
920 BROOKRIDGE LN, ORMOND BEACH, FL, 321...
Community: Plantation Bay Golf & Country Club
MLS FC312725 • DELCO REALTY GROUP INC., Kathy Del...
The Villages®
![5719 SPARTINA TER, THE VILLAGES, FL, 321..., The Villages, FL 32163]()
2 beds
|2 baths
|1,258 sq ft
|Villa
5719 SPARTINA TER, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5098253 • LPT REALTY, LLC, Genie Muldoon
Huntington at Hunter's Ridge
![34 FAWN HAVEN TRL, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,523 sq ft
|House
34 FAWN HAVEN TRL, ORMOND BEACH, FL, 321...
Community: Huntington at Hunter's Ridge
MLS 1210270 • Realty Executives Oceanside, Traci ...
Spruce Creek Country Club
![8806 SE 132ND LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|3 baths
|2,807 sq ft
|House
8806 SE 132ND LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek Country Club
MLS OM710433 • RE/MAX PREMIER REALTY LADY LK, Jay...
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The Villages®
![1224 DUSTIN DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|912 sq ft
|Manufactured Home
1224 DUSTIN DR, LADY LAKE, FL, 32159
Community: The Villages®
MLS OM707875 • VAUGHT REALTY, Billy Vaught
Stonecrest
![17435 SE 112TH AVE, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,682 sq ft
|House
17435 SE 112TH AVE, SUMMERFIELD, FL, 344...
Community: Stonecrest
MLS OM706907 • RE/MAX PREMIER REALTY LADY LK, Don...
The Villages®
![670 FAYETTE CT, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,539 sq ft
|House
670 FAYETTE CT, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5098846 • LPT REALTY, LLC, Dick Betts
Indian River Colony Club
![1551 INDEPENDENCE AVE, MELBOURNE, FL, 32..., Melbourne, FL 32940]()
3 beds
|2 baths
|1,816 sq ft
|House
1551 INDEPENDENCE AVE, MELBOURNE, FL, 32...
Community: Indian River Colony Club
MLS 1043419 • Four Star Real Estate LLC, Robin St...
Latitude Margaritaville
![298 HANG LOOSE WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124]()
2 beds
|3 baths
|2,158 sq ft
|House
298 HANG LOOSE WAY, DAYTONA BEACH, FL, 3...
Community: Latitude Margaritaville
MLS 1213091 • High Class Realty, Cleusa Rendon
Want more information about active adult communities around Winter Park?
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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.
