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Winter Park, FL 55+ active adult communities & homes for sale - Page 59
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
Want to learn more about 55+ communities in Winter Park?
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Questions? Call us:
(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.
Pelican Bay Daytona Beach
![136 SEA DUCK CIR, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32119]()
3 beds
|3 baths
|2,365 sq ft
|House
136 SEA DUCK CIR, DAYTONA BEACH, FL, 321...
Community: Pelican Bay Daytona Beach
MLS 1223052 • Life Real Estate, Alberto Strickhou... • Life Real Estate
Cindy Certified
Plantation at Leesburg
![4721 TARA VIEW RD, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,979 sq ft
|House
4721 TARA VIEW RD, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS O6380183 • KELLER WILLIAMS HERITAGE REALTY, R... • KELLER WILLIAMS HERITAGE REALTY
Heritage Hills
![3538 FAIRWATERS CT B, CLERMONT, FL, 3471..., Clermont, FL 34711]()
2 beds
|2 baths
|1,374 sq ft
|Villa
3538 FAIRWATERS CT B, CLERMONT, FL, 3471...
Community: Heritage Hills
MLS G5107747 • KELLER WILLIAMS ELITE PARTNERS III... • KELLER WILLIAMS ELITE PARTNERS III REALTY
Foxwood Lake Estates
![1679 FOXWAY DR, LAKELAND, FL, 33810, Lakeland, FL 33810]()
2 beds
|2 baths
|1,248 sq ft
|Manufactured Home
1679 FOXWAY DR, LAKELAND, FL, 33810
Community: Foxwood Lake Estates
MLS L4959368 • COLDWELL BANKER REALTY, Kelley Bla... • COLDWELL BANKER REALTY
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Cindy Certified
Cindy Certified
Pennbrooke Fairways
![32747 WESTWOOD LOOP, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,192 sq ft
|House
32747 WESTWOOD LOOP, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS G5108173 • GOLDKEY REAL ESTATE PARTNERS LLC, ... • GOLDKEY REAL ESTATE PARTNERS LLC
Twin Lakes
![5043 VANTAGE CT, ST. CLOUD, FL, 34772, St. Cloud, FL 34772]()
MLS 1069272 • Blue Marlin Real Estate, Kimberly C... • Blue Marlin Real Estate
Twin Lakes
![5043 VANTAGE CT, ST CLOUD, FL, 34772, St Cloud, FL 34772]()
MLS O6382007 • BLUE MARLIN REAL ESTATE, Kimberly ... • BLUE MARLIN REAL ESTATE
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 Bay Golf & Country Club
![60 KINGSLEY CIR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|2 baths
|2,144 sq ft
|House
60 KINGSLEY CIR, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS FC316097 • CLAIRE HUNTER REALTY, Brian Hunter • CLAIRE HUNTER REALTY
Indian River Colony Club
![1311 INDEPENDENCE AVE, MELBOURNE, FL, 32..., Melbourne, FL 32940]()
4 beds
|3 baths
|1,859 sq ft
|House
1311 INDEPENDENCE AVE, MELBOURNE, FL, 32...
Community: Indian River Colony Club
MLS 1069235 • Four Star Real Estate LLC, Shellie ... • Four Star Real Estate LLC
Cindy Certified
Lakes of Mount Dora
![1990 WALLINGFORD LOOP, MOUNT DORA, FL, 3..., Mount Dora, FL 32757]()
3 beds
|3 baths
|2,330 sq ft
|House
1990 WALLINGFORD LOOP, MOUNT DORA, FL, 3...
Community: Lakes of Mount Dora
MLS G5108039 • EXP REALTY LLC, Angie Cable • EXP REALTY LLC
Solivita
![116 GLENDALE CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS O6380665 • COLDWELL BANKER REALTY, Vincent Pa... • COLDWELL BANKER REALTY
Legacy of Leesburg
![5922 SAGE LEAF PL, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,913 sq ft
|House
5922 SAGE LEAF PL, LEESBURG, FL, 34748
Community: Legacy of Leesburg
MLS G5107713 • FLORIDA PLUS REALTY, LLC, Claire B... • FLORIDA PLUS REALTY, LLC
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Heritage Hills
![3632 SOLANA CIR B, CLERMONT, FL, 34711, Clermont, FL 34711]()
2 beds
|2 baths
|1,374 sq ft
|Villa
3632 SOLANA CIR B, CLERMONT, FL, 34711
Community: Heritage Hills
MLS G5107971 • KELLER WILLIAMS ELITE PARTNERS III... • KELLER WILLIAMS ELITE PARTNERS III REALTY
Harbor Hills Country Club
![5321 GREENS DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
3 beds
|2 baths
|2,948 sq ft
|House
5321 GREENS DR, LADY LAKE, FL, 32159
Community: Harbor Hills Country Club
MLS G5107981 • CHARLES RUTENBERG REALTY ORLANDO, ... • CHARLES RUTENBERG REALTY ORLANDO
Plantation Bay Golf & Country Club
![39 MAGNOLIA DR 39, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
2 beds
|2 baths
|1,300 sq ft
|Condo
39 MAGNOLIA DR 39, ORMOND BEACH, FL, 321...
Community: Plantation Bay Golf & Country Club
MLS FC315963 • VENTURE DEVELOPMENT REALTY,INC, El... • VENTURE DEVELOPMENT REALTY,INC
Spruce Creek South
![17952 SE 107TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,450 sq ft
|House
17952 SE 107TH CT, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
MLS O6380283 • ALL FLORIDA PROPERTY GROUP,INC, Me... • ALL FLORIDA PROPERTY GROUP,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.
Cindy Certified
Westhaven at Ovation - Townes Collection
![14075 LOCHEND WAY, WINTER GARDEN, FL, 34..., Winter Garden, FL 34787]()
4 beds
|3 baths
|2,197 sq ft
|Townhouse
14075 LOCHEND WAY, WINTER GARDEN, FL, 34...
Community: Westhaven at Ovation - Townes Collection
MLS O6380897 • PREMIER SOTHEBYS INT'L REALTY, Wen... • PREMIER SOTHEBYS INT'L REALTY
Plantation Bay Golf & Country Club
![39 MAGNOLIA DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
2 beds
|2 baths
|1,300 sq ft
|Condo
39 MAGNOLIA DR, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS 1222747 • Venture Development Realty, Inc, El... • Venture Development Realty, Inc
The Villages®
![3698 ROBERTSON WAY, THE VILLAGES, FL, 32..., The Villages, FL 32163]()
3 beds
|2 baths
|1,695 sq ft
|Villa
3698 ROBERTSON WAY, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5107870 • LPT REALTY, LLC, Genie Muldoon • LPT REALTY, LLC
Latitude Margaritaville
![350 LOST SHAKER WAY, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124]()
3 beds
|3 baths
|2,067 sq ft
|House
350 LOST SHAKER WAY, DAYTONA BEACH, FL, ...
Community: Latitude Margaritaville
MLS 1222743 • Realty Hub, Cherri Tindall • Realty Hub
Plantation at Leesburg
![25308 CASA DEL LAGO LN, LEESBURG, FL, 34..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,344 sq ft
|Manufactured Home
25308 CASA DEL LAGO LN, LEESBURG, FL, 34...
Community: Plantation at Leesburg
MLS G5107740 • LPT REALTY, LLC, Kelly Monroe • LPT REALTY, LLC
The Country Club of Mount Dora
![8032 PINE HOLLOW DR, MOUNT DORA, FL, 327..., Mount Dora, FL 32757]()
3 beds
|2 baths
|1,949 sq ft
|House
8032 PINE HOLLOW DR, MOUNT DORA, FL, 327...
Community: The Country Club of Mount Dora
MLS G5107406 • LPT REALTY, LLC, Kelly Monroe • LPT REALTY, LLC
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Cindy Certified
Cindy Certified
Esplanade at Highland Ranch
![2639 STARGRASS CIR, CLERMONT, FL, 34715, Clermont, FL 34715]()
2 beds
|2 baths
|1,732 sq ft
|House
2639 STARGRASS CIR, CLERMONT, FL, 34715
Community: Esplanade at Highland Ranch
MLS O6379731 • PREMIER SOTHEBYS INT'L REALTY, Aud... • PREMIER SOTHEBYS INT'L 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.
Breakaway Trails
![27 WINDING CREEK WAY, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174]()
3 beds
|3 baths
|2,370 sq ft
|House
27 WINDING CREEK WAY, ORMOND BEACH, FL, ...
Community: Breakaway Trails
MLS FC315957 • BETTER HMS & GARDENS RE SYNERG, Ja... • BETTER HMS & GARDENS RE SYNERG
The Villages®
![8337 SE 176TH LAWSON LOOP, THE VILLAGES,..., The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
8337 SE 176TH LAWSON LOOP, THE VILLAGES,...
Community: The Villages®
MLS OM717826 • WORTH CLARK REALTY, Celeste Dionne • WORTH CLARK REALTY
Stonecrest
![11255 SE 175TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,408 sq ft
|House
11255 SE 175TH LN, SUMMERFIELD, FL, 3449...
Community: Stonecrest
MLS G5107821 • CHARLES RUTENBERG REALTY ORLANDO, ... • CHARLES RUTENBERG REALTY ORLANDO
The Villages®
![2613 AYALA WAY, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,956 sq ft
|House
2613 AYALA WAY, THE VILLAGES, FL, 32162
Community: The Villages®
MLS TB8473349 • SHEEN REAL ESTATE PROFESSIONALS, ... • SHEEN REAL ESTATE PROFESSIONALS, LLC
Cindy Certified
Plantation Bay Golf & Country Club
![831 PINEWOOD DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|3 baths
|2,101 sq ft
|Townhouse
831 PINEWOOD DR, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS FC315021 • FLORIDA HOMES REALTY & MORTGAGE, T... • FLORIDA HOMES REALTY & MORTGAGE
Solivita
![632 PORTOFINO DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS O6379328 • PREMIER SOTHEBYS INT'L REALTY, Ari... • PREMIER SOTHEBYS INT'L REALTY
Park Place
![21 PARK PLACE CIR, PALM COAST, FL, 32164, Palm Coast, FL 32164]()
3 beds
|2 baths
|1,878 sq ft
|House
21 PARK PLACE CIR, PALM COAST, FL, 32164
Community: Park Place
MLS 2128257 • UNITED REAL ESTATE GALLERY, JAMES H... • UNITED REAL ESTATE GALLERY
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Venetian Bay
![3074 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168]()
4 beds
|4 baths
|2,092 sq ft
|Townhouse
3074 ISLES WAY, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
MLS 1222629 • Magnolia Properties, Margie Lints • Magnolia Properties
The Villages®
![2001 CIPRIANO PL, THE VILLAGES, FL, 3215..., The Villages, FL 32159]()
3 beds
|2 baths
|1,527 sq ft
|House
2001 CIPRIANO PL, THE VILLAGES, FL, 3215...
Community: The Villages®
MLS G5107394 • RE/MAX PREMIER REALTY LADY LK, Lyn... • RE/MAX PREMIER REALTY LADY LK
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.
