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Winter Park, FL 55+ active adult communities & homes for sale - Page 60
98 communities near Winter Park
2,702 homes near Winter Park
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4 rating (17 reviews)
![The Villages®]()
$100ks
- $1Ms
The Villages®, The Villages, FL
New and Resale
|
55+ age-restricted
|
Built 1978 - present
|
70,000 homes
$300ks
- $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale
|
Age-targeted
|
Built 2004 - present
|
1,561 homes
4.5 rating (11 reviews)
![Spruce Creek Country Club]()
$100ks
- $400ks
Spruce Creek Country Club, Summerfield, FL
Resale Only
|
55+ age-restricted
|
Built 1996 - 2007
|
3,250 homes
5 rating (2 reviews)
![Plantation at Leesburg]()
$100ks
- $300ks
Plantation at Leesburg, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1987 - 2008
|
2,820 homes
4.7 rating (18 reviews)
![Solivita]()
$300ks
- $700ks
Solivita, Kissimmee, FL
New and Resale
|
55+ age-restricted
|
Built 2000 - present
|
5,900 homes
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3.6 rating (48 reviews)
![Latitude Margaritaville]()
$300ks
- $800ks
Latitude Margaritaville, Daytona Beach, FL
Resale Only
|
55+ age-restricted
|
Built 2017 - 2025
|
3,900 homes
5 rating (1 reviews)
![Plantation Bay Golf &...]()
$400ks
- $2Ms
Plantation Bay Golf &..., Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1988 - present
|
3,500 homes
5 rating (3 reviews)
![Stonecrest]()
$200ks
- $500ks
Stonecrest, Summerfield, FL
Resale Only
|
55+ age-restricted
|
Built 1990 - 2024
|
2,224 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
$100ks
- $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only
|
Age-targeted
|
Built 1980 - 2006
|
1,806 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.
$200ks
- $800ks
Grand Haven, Palm Coast, FL
New and Resale
|
Age-targeted
|
Built 1997 - present
|
1,901 homes
5 rating (7 reviews)
![Kings Ridge]()
$200ks
- $400ks
Kings Ridge, Clermont, FL
Resale Only
|
55+ age-restricted
|
Built 1995 - 2000
|
2,088 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 (3 reviews)
![Lake Ashton]()
$200ks
- $500ks
Lake Ashton, Lake Wales, FL
Resale Only
|
55+ age-restricted
|
Built 2002 - present
|
1,600 homes
5 rating (8 reviews)
![Royal Highlands]()
$200ks
- $400ks
Royal Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2006
|
1,500 homes
4 rating (4 reviews)
![Lakes of Mount Dora]()
$300ks
- $900ks
Lakes of Mount Dora, Mount Dora, FL
New and Resale
|
55+ age-restricted
|
Built 2006 - present
|
950 homes
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2.8 rating (6 reviews)
![Arlington Ridge]()
$200ks
- $500ks
Arlington Ridge, Leesburg, FL
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
629 homes
5 rating (1 reviews)
![Sandpiper Golf & Coun...]()
$100ks
- $300ks
Sandpiper Golf & Coun..., Lakeland, FL
New and Resale
|
55+ age-restricted
|
Built 1985 - present
|
1,193 homes
$300ks
- $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1980 - present
|
1,000 homes
3.8 rating (4 reviews)
![Spruce Creek South]()
$100ks
- $200ks
Spruce Creek South, Summerfield, FL
Resale Only
|
55+ age-restricted
|
Built 1989 - 1995
|
1,650 homes
Download the Ultimate 55+ Homebuying Guide
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4 rating (2 reviews)
![Harbor Hills Country Club]()
$300ks
- $900ks
Harbor Hills Country Club, Lady Lake, FL
New and Resale
|
Age-targeted
|
Built 1989 - present
|
940 homes
5 rating (1 reviews)
![Cresswind at Victoria Gar...]()
$300ks
- $500ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only
|
55+ age-restricted
|
Built 2001 - 2022
|
1,070 homes
$100ks
- $300ks
Highland Fairways, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1983 - 1998
|
660 homes
$400ks
- $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1985 - present
|
976 homes
$200ks
- $1Ms
The Country Club of Mount..., Mount Dora, FL
Resale Only
|
Age-targeted
|
Built 1991 - 2005
|
827 homes
3.6 rating (5 reviews)
![Heritage Hills]()
$200ks
- $400ks
Heritage Hills, Clermont, FL
New and Resale
|
55+ age-restricted
|
Built 2006 - present
|
1,154 homes
5 rating (1 reviews)
![Royal Harbor]()
$200ks
- $800ks
Royal Harbor, Tavares, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2008
|
755 homes
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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)
![Del Webb Sunbridge]()
$400ks
- $800ks
Del Webb Sunbridge, St. Cloud, FL
New and Resale
|
55+ age-restricted
|
Built 2019 - present
|
1,300 homes
$300ks
- $400ks
Gatherings of Lake Nona, Orlando, FL
New and Resale
|
55+ age-restricted
|
Built 2017 - present
|
216 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
Heritage - The Cottages o..., Okahumpka, FL
New Construction
|
55+ age-restricted
|
Built 2022 - present
|
179 homes
4.8 rating (6 reviews)
![Highland Lakes]()
$100ks
- $200ks
Highland Lakes, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1990 - 1999
|
938 homes
1 rating (1 reviews)
![Sullivan Ranch]()
$200ks
- $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2020
|
692 homes
4.4 rating (16 reviews)
![Del Webb Orlando]()
$200ks
- $500ks
Del Webb Orlando, Davenport, FL
Resale Only
|
55+ age-restricted
|
Built 2007 - 2021
|
937 homes
$100ks
- $200ks
Foxwood Lake Estates, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1982 - 1987
|
545 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
$200ks
- $500ks
The Timbers at Everlands, Palm Bay, FL
New Construction
|
55+ age-restricted
|
Built 2023 - present
|
450 homes
5 rating (1 reviews)
![VillageWalk at Lake Nona]()
$300ks
- $700ks
VillageWalk at Lake Nona, Orlando, FL
Resale Only
|
Age-targeted
|
Built 2006 - 2016
|
1,300 homes
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(888) 625-4885
$300ks
- $600ks
Four Seasons at Orlando, Kissimmee, FL
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
557 homes
$100ks
- $200ks
Colonnades, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1985 - 1994
|
360 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.
The Villages®
![758 MOORE TER, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|2,642 sq ft
|House
758 MOORE TER, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5107698 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
Cindy Certified
Four Seasons at Orlando
![7637 SAND PIERRE CT, KISSIMMEE, FL, 3474..., Kissimmee, FL 34747]()
2 beds
|2 baths
|1,557 sq ft
|Villa
7637 SAND PIERRE CT, KISSIMMEE, FL, 3474...
Community: Four Seasons at Orlando
MLS O6379571 • EXP REALTY LLC, Harold Olson • EXP REALTY LLC
Huntington at Hunter's Ridge
![33 FAWN HAVEN TRL, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,156 sq ft
|House
33 FAWN HAVEN TRL, ORMOND BEACH, FL, 321...
Community: Huntington at Hunter's Ridge
MLS V4946964 • RE/MAX SIGNATURE, Rola Michael • RE/MAX SIGNATURE
Del Webb Sunbridge
![2434 N CLIFF WAY, ST CLOUD, FL, 34771, St Cloud, FL 34771]()
2 beds
|2 baths
|1,584 sq ft
|Villa
2434 N CLIFF WAY, ST CLOUD, FL, 34771
Community: Del Webb Sunbridge
MLS L4958972 • BETTER HOMES & GARDENS RE LIFESTYL... • BETTER HOMES & GARDENS RE LIFESTYLES
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Lake James
![7826 LAKE JAMES BLVD, LAKELAND, FL, 3381..., Lakeland, FL 33810]()
2 beds
|2 baths
|1,788 sq ft
|House
7826 LAKE JAMES BLVD, LAKELAND, FL, 3381...
Community: Lake James
MLS L4958971 • CLARK REALTY LLC, Steven Perkins • CLARK REALTY LLC
The Villages®
![13811 COUNTY RD, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
4 beds
|2 baths
|2,280 sq ft
|Manufactured Home
13811 COUNTY RD, LADY LAKE, FL, 32159
Community: The Villages®
MLS O6379162 • THE PROPERTY PROS REAL ESTATE, INC... • THE PROPERTY PROS REAL ESTATE, INC
The Country Club of Mount Dora
![8013 PINE HOLLOW DR, MOUNT DORA, FL, 327..., Mount Dora, FL 32757]()
3 beds
|2 baths
|2,256 sq ft
|House
8013 PINE HOLLOW DR, MOUNT DORA, FL, 327...
Community: The Country Club of Mount Dora
MLS G5106558 • COLDWELL BANKER VANGUARD EDGE, Lyn... • COLDWELL BANKER VANGUARD EDGE
Cindy Certified
Del Webb Minneola
![2750 PURPLE MEADOW CT, MINNEOLA, FL, 347..., Minneola, FL 34715]()
2 beds
|2 baths
|1,409 sq ft
|House
2750 PURPLE MEADOW CT, MINNEOLA, FL, 347...
Community: Del Webb Minneola
MLS G5107474 • CENTURY 21 MYERS ROSE REALTY, Dawn... • CENTURY 21 MYERS ROSE REALTY
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.
Plantation at Leesburg
![24239 BELLE MEDE DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|2,289 sq ft
|House
24239 BELLE MEDE DR, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5107374 • ERA GRIZZARD REAL ESTATE, Lisa Car... • ERA GRIZZARD REAL ESTATE
The Villages®
![8371 SE 168TH TRINITY PL, THE VILLAGES, ..., The Villages, FL 32162]()
3 beds
|2 baths
|1,496 sq ft
|House
8371 SE 168TH TRINITY PL, THE VILLAGES, ...
Community: The Villages®
MLS O6378880 • BEYCOME OF FLORIDA LLC, Steven Kol... • BEYCOME OF FLORIDA LLC
Halifax Plantation
![3763 CARRICK DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|2 baths
|2,264 sq ft
|House
3763 CARRICK DR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
MLS 1222469 • Ormond Realty, Jane Vasiliades • Ormond Realty
Cindy Certified
Plantation at Leesburg
![25607 BELLE HELENE, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,345 sq ft
|House
25607 BELLE HELENE, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5106688 • DOWN HOME REALTY, LLLP, Colleen A.... • DOWN HOME REALTY, LLLP
Royal Harbor
![5685 GULF STREAM ST, TAVARES, FL, 32778, Tavares, FL 32778]()
3 beds
|2 baths
|1,823 sq ft
|House
5685 GULF STREAM ST, TAVARES, FL, 32778
Community: Royal Harbor
MLS G5107595 • WATSON REALTY CORP, Darlene Fritzk... • WATSON REALTY CORP
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Questions? Call us:
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Breakaway Trails
![27 LAKE VISTA WAY, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
4 beds
|4 baths
|3,505 sq ft
|House
27 LAKE VISTA WAY, ORMOND BEACH, FL, 321...
Community: Breakaway Trails
MLS O6378370 • MARVIEW INTERNATIONAL REALTY LLC, ... • MARVIEW INTERNATIONAL REALTY LLC
Solivita
![884 GRAND CANAL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS O6378535 • FLORIDA PLUS REALTY, LLC, Sarah Bo... • FLORIDA PLUS REALTY, LLC
Solivita
![172 ACADIA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5142477 • THE FIRM RE, Judy Colon • THE FIRM RE
Latitude Margaritaville
![215 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124]()
2 beds
|3 baths
|1,748 sq ft
|House
215 GYPSY PALACE LN, DAYTONA BEACH, FL, ...
Community: Latitude Margaritaville
MLS 1222412 • Fathom Realty FL LLC, Adrienne Smit... • Fathom Realty FL 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.
Cindy Certified
Cindy Certified
Grand Haven
![33 MARSHVIEW LN, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
3 beds
|2 baths
|2,493 sq ft
|House
33 MARSHVIEW LN, PALM COAST, FL, 32137
Community: Grand Haven
MLS FC315663 • COASTAL GATEWAY REAL ESTATE GR, Su... • COASTAL GATEWAY REAL ESTATE GR
Latitude Margaritaville
![410 LOST SHAKER WAY, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,848 sq ft
|House
410 LOST SHAKER WAY, DAYTONA BEACH, FL, ...
Community: Latitude Margaritaville
MLS 1222330 • Realty Hub, Cherri Tindall • Realty Hub
Spruce Creek Country Club
![9050 SE 135TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,867 sq ft
|House
9050 SE 135TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek Country Club
MLS OM717715 • RE/MAX FOXFIRE - SUMMERFIELD, Eile... • RE/MAX FOXFIRE - SUMMERFIELD
Del Webb Sunbridge
![2722 RIVER CREEK LN, ST CLOUD, FL, 34771, St Cloud, FL 34771]()
3 beds
|4 baths
|3,778 sq ft
|House
2722 RIVER CREEK LN, ST CLOUD, FL, 34771
Community: Del Webb Sunbridge
MLS S5142728 • AVANTI WAY REALTY LLC, Jim McQuade • AVANTI WAY REALTY LLC
Pelican Bay Daytona Beach
![152 LOON CT, DAYTONA BEACH, FL, 32119, Daytona Beach, FL 32119]()
3 beds
|2 baths
|1,650 sq ft
|House
152 LOON CT, DAYTONA BEACH, FL, 32119
Community: Pelican Bay Daytona Beach
MLS O6377798 • RC GROUP REALTY LLC, Erika Gao • RC GROUP REALTY LLC
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Spruce Creek South
![10319 SE 177TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,143 sq ft
|House
10319 SE 177TH PL, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
MLS G5105087 • FLORIDA FINE HOMES REALTY, LLC, Ji... • FLORIDA FINE HOMES REALTY, LLC
High Vista at Ridgewood Lakes
![213 HIGH VISTA DR, DAVENPORT, FL, 33837, Davenport, FL 33837]()
2 beds
|2 baths
|1,542 sq ft
|House
213 HIGH VISTA DR, DAVENPORT, FL, 33837
Community: High Vista at Ridgewood Lakes
MLS O6377157 • KELLER WILLIAMS CLASSIC, Simi Lakh... • KELLER WILLIAMS CLASSIC
Cresswind at Victoria Gardens
![112 BELLINGRATH TER, DELAND, FL, 32724, Deland, FL 32724]()
3 beds
|2 baths
|2,546 sq ft
|House
112 BELLINGRATH TER, DELAND, FL, 32724
Community: Cresswind at Victoria Gardens
MLS O6376772 • BETTER HOMES AND GARDENS REAL ESTA... • BETTER HOMES AND GARDENS REAL ESTATE MANN GLOBAL P
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®
![1116 SAN BERNARDO RD, THE VILLAGES, FL, ..., The Villages, FL 32162]()
2 beds
|2 baths
|1,102 sq ft
|Villa
1116 SAN BERNARDO RD, THE VILLAGES, FL, ...
Community: The Villages®
MLS G5107263 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
Cindy Certified
Plantation Bay Golf & Country Club
![1000 KILKENNY LN, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
2 beds
|2 baths
|1,510 sq ft
|Townhouse
1000 KILKENNY LN, ORMOND BEACH, FL, 3217...
Community: Plantation Bay Golf & Country Club
MLS FC315582 • VENTURE DEVELOPMENT REALTY,INC, El... • VENTURE DEVELOPMENT REALTY,INC
Venetian Bay
![3470 TESORO CIR, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|2,852 sq ft
|House
3470 TESORO CIR, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
MLS 1222144 • EXP Realty LLC, Dolores Leza • EXP Realty LLC
Cindy Certified
Solivita
![305 ROCK SPRINGS DR, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759]()
3 beds
|3 baths
|2,454 sq ft
|House
305 ROCK SPRINGS DR, KISSIMMEE, FL, 3475...
Community: Solivita
MLS S5142040 • PELLEGO, LLC, Stan Wilson • PELLEGO, LLC
The Villages®
![1115 SALIDO AVE, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
3 beds
|2 baths
|1,728 sq ft
|House
1115 SALIDO AVE, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5107206 • RE/MAX FOXFIRE - SUMMERFIELD, Kell... • RE/MAX FOXFIRE - SUMMERFIELD
Lake Ashton
![4632 TURNBERRY LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859]()
3 beds
|2 baths
|2,354 sq ft
|House
4632 TURNBERRY LN, LAKE WALES, FL, 33859
Community: Lake Ashton
MLS L4958817 • 54 REALTY LLC, Jordan Prais • 54 REALTY LLC
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Solivita
![308 BEACON AVE, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5141183 • PELLEGO, LLC, Diane Cisek • PELLEGO, LLC
Spruce Creek Country Club
![13667 SE 91ST AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|2,270 sq ft
|House
13667 SE 91ST AVE, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS OM717197 • RE/MAX FOXFIRE - SUMMERFIELD, Ed D... • RE/MAX FOXFIRE - SUMMERFIELD
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.
Frequently Asked Questions
In Winter Park, there is 1 small community with less than 500 homes.
The smallest 55+ community in Winter Park has 178 homes, the largest has 178 homes, and the average community consists of 178 homes.
Yes, there is new 55+ home available in Winter Park. The most recent community started in Winter Park include Rosalia Winter Park. There is also 1 community in Winter Park that offers new construction homes, including Rosalia Winter Park.
Yes, there is gated 55+ community in Winter Park. The only 55+ community in Winter Park is gated. For instance, Rosalia Winter Park is a gated community with 178 homes.
Want more information about active adult communities around Winter Park?
Want to learn more about 55+ communities in Winter Park?
2,702
homes
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REIN updates its listings on a daily basis. Data last updated: Aug 25, 2026.
This application does not include information on all of the properties available for sale at this time.
