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Winter Park, FL 55+ active adult communities & homes for sale - Page 32
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
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
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4.7 rating (18 reviews)
![Solivita]()
$300ks
- $700ks
Solivita, Kissimmee, FL
New and Resale
|
55+ age-restricted
|
Built 2000 - present
|
5,900 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 (8 reviews)
![Royal Highlands]()
$200ks
- $400ks
Royal Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2006
|
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
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
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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
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
2.8 rating (6 reviews)
![Arlington Ridge]()
$200ks
- $500ks
Arlington Ridge, Leesburg, FL
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
629 homes
$300ks
- $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1980 - present
|
1,000 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 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
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)
![Cresswind at Victoria Gar...]()
$300ks
- $500ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only
|
55+ age-restricted
|
Built 2001 - 2022
|
1,070 homes
$200ks
- $1Ms
The Country Club of Mount..., Mount Dora, FL
Resale Only
|
Age-targeted
|
Built 1991 - 2005
|
827 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
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
Heritage - The Cottages o..., Okahumpka, FL
New Construction
|
55+ age-restricted
|
Built 2022 - present
|
179 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
- $400ks
Gatherings of Lake Nona, Orlando, FL
New and Resale
|
55+ age-restricted
|
Built 2017 - present
|
216 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
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
$200ks
- $500ks
The Timbers at Everlands, Palm Bay, FL
New Construction
|
55+ age-restricted
|
Built 2023 - present
|
450 homes
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$200ks
- $400ks
The Lakes at Harmony, Harmony, FL
New and Resale
|
55+ age-restricted
|
Built 2016 - present
|
400 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.
Del Webb Minneola
![2458 DEL WEBB DR, MINNEOLA, FL, 34715, Minneola, FL 34715]()
3 beds
|3 baths
|2,260 sq ft
|House
2458 DEL WEBB DR, MINNEOLA, FL, 34715
Community: Del Webb Minneola
MLS G5114083 • SELLSTATE INNOVATION REALTY, April... • SELLSTATE INNOVATION REALTY
Cindy Certified
Venetian Bay
![3321 MARSILI AVE, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
4 beds
|3 baths
|2,540 sq ft
|House
3321 MARSILI AVE, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS NS1088502 • COLLADO REAL ESTATE, Pat Collado • COLLADO REAL ESTATE
Pennbrooke Fairways
![32222 SUMMERTREE CIR, LEESBURG, FL, 3474..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,725 sq ft
|House
32222 SUMMERTREE CIR, LEESBURG, FL, 3474...
Community: Pennbrooke Fairways
MLS G5113595 • KELLER WILLIAMS ELITE PARTNERS III... • KELLER WILLIAMS ELITE PARTNERS III REALTY
Spruce Creek Country Club
![9119 SE 120TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,488 sq ft
|House
9119 SE 120TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek Country Club
MLS O6418689 • REGENCY REAL ESTATE LLC, Evelyn Te... • REGENCY REAL ESTATE LLC
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Cindy Certified
The Villages®
![3394 RANDI RD, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|1,810 sq ft
|Villa
3394 RANDI RD, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5114046 • SALLY LOVE REAL ESTATE, Sally Love • SALLY LOVE REAL ESTATE
Cindy Certified
Cindy Certified
Vienna Square
![2452 SALZBURG LOOP, WINTER HAVEN, FL, 33..., Winter Haven, FL 33884]()
2 beds
|2 baths
|1,729 sq ft
|House
2452 SALZBURG LOOP, WINTER HAVEN, FL, 33...
Community: Vienna Square
MLS L4962907 • AMPLIFY REAL ESTATE SERVICES FL, N... • AMPLIFY REAL ESTATE SERVICES FL
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.
Venetian Bay
![424 LUNA BELLA LN 231, NEW SMYRNA BEACH,..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|1,953 sq ft
|Condo
424 LUNA BELLA LN 231, NEW SMYRNA BEACH,...
Community: Venetian Bay
MLS NS1088282 • NSB HOMES LLC, Donna Concannon • NSB HOMES LLC
Legacy of Leesburg
![27134 NOSTALGIA DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,601 sq ft
|House
27134 NOSTALGIA DR, LEESBURG, FL, 34748
Community: Legacy of Leesburg
MLS G5114067 • KELLER WILLIAMS ELITE PARTNERS III... • KELLER WILLIAMS ELITE PARTNERS III REALTY
Cindy Certified
Harbor Hills Country Club
![5506 CITATION CT, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
3 beds
|3 baths
|2,698 sq ft
|House
5506 CITATION CT, LADY LAKE, FL, 32159
Community: Harbor Hills Country Club
MLS G5113948 • MORRIS REALTY AND INVESTMENTS, The... • MORRIS REALTY AND INVESTMENTS
Stonecrest
![17719 SE 114TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,704 sq ft
|Villa
17719 SE 114TH CT, SUMMERFIELD, FL, 3449...
Community: Stonecrest
MLS G5113536 • BASSETT PREMIER REALTY INC, Sharon... • BASSETT PREMIER REALTY INC
Cindy Certified
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Questions? Call us:
(888) 625-4885
Heritage - The Cottages of Sanders Grove
![6213 SANDERS GROVE CIR, OKAHUMPKA, FL, 3..., Okahumpka, FL 34762]()
4 beds
|2 baths
|1,625 sq ft
|House
6213 SANDERS GROVE CIR, OKAHUMPKA, FL, 3...
Community: Heritage - The Cottages of Sanders Grove
MLS G5113907 • OLYMPUS EXECUTIVE REALTY INC, Nanc... • OLYMPUS EXECUTIVE REALTY INC
Heritage - The Cottages of Sanders Grove
![6217 SANDERS GROVE CIR, OKAHUMPKA, FL, 3..., Okahumpka, FL 34762]()
4 beds
|3 baths
|1,938 sq ft
|House
6217 SANDERS GROVE CIR, OKAHUMPKA, FL, 3...
Community: Heritage - The Cottages of Sanders Grove
MLS G5113912 • OLYMPUS EXECUTIVE REALTY INC, Nanc... • OLYMPUS EXECUTIVE REALTY INC
Heritage - The Cottages of Sanders Grove
![5715 HIAWASSEE RD, OKAHUMPKA, FL, 34762, Okahumpka, FL 34762]()
4 beds
|3 baths
|1,938 sq ft
|House
5715 HIAWASSEE RD, OKAHUMPKA, FL, 34762
Community: Heritage - The Cottages of Sanders Grove
MLS G5113916 • OLYMPUS EXECUTIVE REALTY INC, Nanc... • OLYMPUS EXECUTIVE REALTY INC
Heritage - The Cottages of Sanders Grove
![6205 SANDERS GROVE CIR, OKAHUMPKA, FL, 3..., Okahumpka, FL 34762]()
3 beds
|2 baths
|1,407 sq ft
|House
6205 SANDERS GROVE CIR, OKAHUMPKA, FL, 3...
Community: Heritage - The Cottages of Sanders Grove
MLS G5113773 • OLYMPUS EXECUTIVE REALTY INC, Nanc... • OLYMPUS EXECUTIVE REALTY INC
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®
![1516 MARTINEZ DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|1,546 sq ft
|Villa
1516 MARTINEZ DR, LADY LAKE, FL, 32159
Community: The Villages®
MLS G5113765 • KELLER WILLIAMS CORNERSTONE RE, Ka... • KELLER WILLIAMS CORNERSTONE RE
Heritage - The Cottages of Sanders Grove
![5719 HIAWASSEE RD, OKAHUMPKA, FL, 34762, Okahumpka, FL 34762]()
4 beds
|2 baths
|1,625 sq ft
|House
5719 HIAWASSEE RD, OKAHUMPKA, FL, 34762
Community: Heritage - The Cottages of Sanders Grove
MLS G5113918 • OLYMPUS EXECUTIVE REALTY INC, Nanc... • OLYMPUS EXECUTIVE REALTY INC
The Villages®
![2132 SANSORES ST, THE VILLAGES, FL, 3215..., The Villages, FL 32159]()
3 beds
|2 baths
|1,916 sq ft
|House
2132 SANSORES ST, THE VILLAGES, FL, 3215...
Community: The Villages®
MLS G5113068 • RE/MAX FOXFIRE - SUMMERFIELD, Kell... • RE/MAX FOXFIRE - SUMMERFIELD
Kings Ridge
![3916 SCARBOROUGH CT, CLERMONT, FL, 34711, Clermont, FL 34711]()
3 beds
|2 baths
|2,147 sq ft
|House
3916 SCARBOROUGH CT, CLERMONT, FL, 34711
Community: Kings Ridge
MLS G5113844 • REAL BROKER, LLC, Diane Rogers • REAL BROKER, LLC
The Villages®
![1492 OLUSTEE PL, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|1,917 sq ft
|House
1492 OLUSTEE PL, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5113646 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
Kings Ridge
![2265 CALVERT CT, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS G5113837 • REAL BROKER, LLC, Diane Rogers • REAL BROKER, LLC
Twin Lakes
![5042 DANCY LN, ST CLOUD, FL, 34772, St Cloud, FL 34772]()
MLS O6418328 • PULTE REALTY OF NORTH FLORIDA LLC,... • PULTE REALTY OF NORTH FLORIDA LLC
Want to learn more about 55+ communities in Winter Park?
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(888) 625-4885
Silver Lakes
![2258 SILVER RE DR, LAKELAND, FL, 33810, Lakeland, FL 33810]()
3 beds
|2 baths
|1,355 sq ft
|House
2258 SILVER RE DR, LAKELAND, FL, 33810
Community: Silver Lakes
MLS L4962666 • TRUE FLORIDA REALTY LLC, Marilyn D... • TRUE FLORIDA REALTY LLC
The Villages®
![1260 GRANADA CT, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|1,541 sq ft
|House
1260 GRANADA CT, LADY LAKE, FL, 32159
Community: The Villages®
MLS G5113972 • RE/MAX SELECT PARTNERS, Renee Hous... • RE/MAX SELECT PARTNERS
Colonnades
![4918 PLEASANT HOLLOW TRL, LAKELAND, FL, ..., Lakeland, FL 33811]()
2 beds
|2 baths
|1,123 sq ft
|House
4918 PLEASANT HOLLOW TRL, LAKELAND, FL, ...
Community: Colonnades
MLS L4962797 • KELLER WILLIAMS REALTY, Ashley Bea... • KELLER WILLIAMS 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.
Solivita
![380 SORRENTO RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS O6416806 • MAINSTAY BROKERAGE LLC, Eva Hocken... • MAINSTAY BROKERAGE LLC
Arlington Ridge
![4834 INDEPENDENCE TRL, LEESBURG, FL, 347..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,772 sq ft
|House
4834 INDEPENDENCE TRL, LEESBURG, FL, 347...
Community: Arlington Ridge
MLS O6417949 • REGENCY REAL ESTATE LLC, Heather S... • REGENCY REAL ESTATE LLC
Breakaway Trails
![56 CIRCLE CREEK WAY, ORMOND BEACH, FL, 3..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,748 sq ft
|House
56 CIRCLE CREEK WAY, ORMOND BEACH, FL, 3...
Community: Breakaway Trails
MLS 1227692 • Realty Experts Florida, Lonnie Mara... • Realty Experts Florida
Lake James
![2356 LAKE JAMES WAY, LAKELAND, FL, 33810, Lakeland, FL 33810]()
2 beds
|2 baths
|2,124 sq ft
|House
2356 LAKE JAMES WAY, LAKELAND, FL, 33810
Community: Lake James
MLS L4962745 • DREAM REALTY GROUP, Teresa Roberts • DREAM REALTY GROUP
Summit Greens
![3003 PINNACLE CT, CLERMONT, FL, 34711, Clermont, FL 34711]()
2 beds
|2 baths
|1,718 sq ft
|House
3003 PINNACLE CT, CLERMONT, FL, 34711
Community: Summit Greens
MLS G5113939 • WEICHERT REALTORS-HALLMARK PR, Mar... • WEICHERT REALTORS-HALLMARK PR
Heritage - The Cottages of Sanders Grove
![5727 HIAWASSEE RD, OKAHUMPKA, FL, 34762, Okahumpka, FL 34762]()
3 beds
|2 baths
|1,407 sq ft
|House
5727 HIAWASSEE RD, OKAHUMPKA, FL, 34762
Community: Heritage - The Cottages of Sanders Grove
MLS G5113921 • OLYMPUS EXECUTIVE REALTY INC, Nanc... • OLYMPUS EXECUTIVE REALTY INC
Cindy Certified
The Villages®
![16581 SE 77TH NORTHRIDGE CT, THE VILLAGE..., The Villages, FL 32162]()
3 beds
|2 baths
|1,850 sq ft
|House
16581 SE 77TH NORTHRIDGE CT, THE VILLAGE...
Community: The Villages®
MLS TB8520567 • EXP REALTY LLC, Valerie Rubalcaba... • EXP REALTY LLC
Want to learn more about 55+ communities in Winter Park?
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(888) 625-4885
Halifax Plantation
![3250 BAILEY ANN DR, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174]()
2 beds
|2 baths
|1,687 sq ft
|House
3250 BAILEY ANN DR, ORMOND BEACH, FL, 32...
Community: Halifax Plantation
MLS 2151125 • KELLER WILLIAMS REALTY ATLANTIC PAR... • KELLER WILLIAMS REALTY ATLANTIC PARTNERS ST. AUGUSTINE
Cindy Certified
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.
