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Winter Park, FL 55+ active adult communities & homes for sale - Page 25
93 communities near Winter Park
2,414 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
4.7 rating (18 reviews)
![Solivita]()
$300ks
- $700ks
Solivita, Kissimmee, FL
New and Resale
|
55+ age-restricted
|
Built 2000 - present
|
5,900 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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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
$300ks
- $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale
|
Age-targeted
|
Built 2004 - present
|
1,561 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 (3 reviews)
![Stonecrest]()
$200ks
- $500ks
Stonecrest, Summerfield, FL
Resale Only
|
55+ age-restricted
|
Built 1990 - 2024
|
2,224 homes
$200ks
- $800ks
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.
2.8 rating (6 reviews)
![Arlington Ridge]()
$200ks
- $500ks
Arlington Ridge, Leesburg, FL
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
629 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)
![Twin Lakes]()
$200ks
- $600ks
Twin Lakes, St. Cloud, FL
New and Resale
|
55+ age-restricted
|
Built 2016 - present
|
2,000 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 (7 reviews)
![Kings Ridge]()
$200ks
- $400ks
Kings Ridge, Clermont, FL
Resale Only
|
55+ age-restricted
|
Built 1995 - 2000
|
2,088 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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$100ks
- $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only
|
Age-targeted
|
Built 1980 - 2006
|
1,806 homes
$300ks
- $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1980 - present
|
1,000 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
4 rating (4 reviews)
![Lakes of Mount Dora]()
$300ks
- $1Ms
Lakes of Mount Dora, Mount Dora, FL
New and Resale
|
55+ age-restricted
|
Built 2006 - present
|
950 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)
![Del Webb Sunbridge]()
$400ks
- $800ks
Del Webb Sunbridge, St. Cloud, FL
New and Resale
|
55+ age-restricted
|
Built 2019 - present
|
1,300 homes
5 rating (1 reviews)
![Cresswind at Victoria Gar...]()
$200ks
- $500ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only
|
55+ age-restricted
|
Built 2001 - 2022
|
1,070 homes
$200ks
- $400ks
Summer Trees, Port Orange, FL
Resale Only
|
55+ age-restricted
|
Built 1976 - 2005
|
500 homes
$200ks
- $400ks
The Lakes at Harmony, Harmony, FL
New and Resale
|
55+ age-restricted
|
Built 2016 - present
|
400 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 (2 reviews)
![Heritage Isle]()
$300ks
- $500ks
Heritage Isle, Viera, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2017
|
1,500 homes
5 rating (8 reviews)
![Pennbrooke Fairways]()
<$100k
- $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1980 - 2004
|
1,200 homes
$400ks
- $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1985 - present
|
976 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
- $600ks
Four Seasons at Orlando, Kissimmee, FL
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
557 homes
$100ks
- $200ks
Scottish Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1983 - 1992
|
653 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
$200ks
- $1Ms
The Country Club of Mount..., Mount Dora, FL
Resale Only
|
Age-targeted
|
Built 1991 - 2005
|
827 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
$100ks
- $200ks
Foxwood Lake Estates, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1982 - 1987
|
545 homes
Want to learn more about 55+ communities in Winter Park?
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Questions? Call us:
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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
5 rating (2 reviews)
![Bridgewater at Viera]()
$300ks
- $800ks
Bridgewater at Viera, Melbourne, FL
Resale Only
|
55+ age-restricted
|
Built 2017 - 2023
|
870 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®
![1503 ESPARZA PL, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
3 beds
|2 baths
|1,392 sq ft
|House
1503 ESPARZA PL, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5109597 • FLORIDA FINE HOMES REALTY, LLC, Ji...
Twin Lakes
![2303 DATURA LOOP, ST CLOUD, FL, 34772, St Cloud, FL 34772]()
MLS O6396116 • COLDWELL BANKER REALTY, Thad Czapk...
The Villages®
![1116 W BOONE CT, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|1,144 sq ft
|Modular
1116 W BOONE CT, LADY LAKE, FL, 32159
Community: The Villages®
MLS OM722106 • SOUTHERN ASSOCIATES REALTY LLC, Da...
Bridgewater at Viera
![1453 GREAT BELT CIR, MELBOURNE, FL, 3294..., Melbourne, FL 32940]()
3 beds
|2 baths
|1,590 sq ft
|House
1453 GREAT BELT CIR, MELBOURNE, FL, 3294...
Community: Bridgewater at Viera
MLS 1073848 • 1 Percent Lists FL's Finest, Karen ...
Spruce Creek Country Club
![13126 SE 93RD TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,644 sq ft
|House
13126 SE 93RD TERRACE RD, SUMMERFIELD, F...
Community: Spruce Creek Country Club
MLS OM720596 • JUDY L. TROUT REALTY, Judy Trout
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Kings Ridge
![2144 ADDISON AVE, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS B26011333 • Illustrated Properties LLC (Jupit...
The Villages®
![626 REEVESVILLE LN, THE VILLAGES, FL, 32..., The Villages, FL 32162]()
3 beds
|2 baths
|1,398 sq ft
|Villa
626 REEVESVILLE LN, THE VILLAGES, FL, 32...
Community: The Villages®
MLS OM722006 • SALLY LOVE REAL ESTATE, Star Amado...
Twin Lakes
![5017 E FOUNTAINWOOD DR, ST CLOUD, FL, 34..., St Cloud, FL 34772]()
3 beds
|2 baths
|1,863 sq ft
|House
5017 E FOUNTAINWOOD DR, ST CLOUD, FL, 34...
Community: Twin Lakes
MLS O6395461 • EXP REALTY LLC, Brittany Pride
Solivita
![967 LADERA RANCH RD, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759]()
4 beds
|3 baths
|2,465 sq ft
|House
967 LADERA RANCH RD, KISSIMMEE, FL, 3475...
Community: Solivita
MLS O6395722 • STRONG FOUNDATION REALTY LLC, Harr...
Fountain View
![1348 FOUNTAIN VIEW ST, ORMOND BEACH, FL,..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,336 sq ft
|House
1348 FOUNTAIN VIEW ST, ORMOND BEACH, FL,...
Community: Fountain View
MLS O6395883 • DR 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.
The Lakes at Harmony
![3399 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773]()
3 beds
|2 baths
|1,550 sq ft
|House
3399 SAGEBRUSH ST, HARMONY, FL, 34773
Community: The Lakes at Harmony
MLS S5147072 • LPT REALTY, LLC, Monica Guajardo G...
Highland Lakes
![5618 ROSEWALL CIR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,306 sq ft
|House
5618 ROSEWALL CIR, LEESBURG, FL, 34748
Community: Highland Lakes
MLS G5110464 • MICKI BLACKBURN REALTY, Sonia Brow...
The Villages®
![1088 GENNESSE LN, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
2 beds
|2 baths
|1,240 sq ft
|House
1088 GENNESSE LN, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS O6395404 • MARKET CONNECT REALTY LLC, Mark Cl...
The Villages®
![2149 ESCOBAR AVE, THE VILLAGES, FL, 3215..., The Villages, FL 32159]()
2 beds
|2 baths
|1,121 sq ft
|Villa
2149 ESCOBAR AVE, THE VILLAGES, FL, 3215...
Community: The Villages®
MLS G5110356 • RE/MAX PREMIER REALTY, Matthew Rob...
Stonecrest
![17180 SE 115TH TERRACE RD, SUMMERFIELD, ..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,796 sq ft
|House
17180 SE 115TH TERRACE RD, SUMMERFIELD, ...
Community: Stonecrest
MLS O6394270 • EQUITYPRO LLC, Melissa Osborne
Plantation Bay Golf & Country Club
![830 ALDENHAM LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
2 beds
|2 baths
|1,510 sq ft
|Townhouse
830 ALDENHAM LN, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS FC317274 • VENTURE DEVELOPMENT REALTY,INC, De...
Want to learn more about 55+ communities in Winter Park?
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Questions? Call us:
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Del Webb at Viera
![8984 NIXIE AVE, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|2 baths
|1,919 sq ft
|House
8984 NIXIE AVE, MELBOURNE, FL, 32940
Community: Del Webb at Viera
MLS 1073832 • Coldwell Banker Realty, Clara Quint...
Summer Trees
![120 CROOKED PINE RD, PORT ORANGE, FL, 32..., Port Orange, FL 32128]()
2 beds
|2 baths
|1,245 sq ft
|House
120 CROOKED PINE RD, PORT ORANGE, FL, 32...
Community: Summer Trees
MLS 1224895 • Heritage Realty Associates, Lori Cl...
Halifax Plantation
![1352 ARKLOW CIR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
4 beds
|4 baths
|2,721 sq ft
|House
1352 ARKLOW CIR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
MLS 1224869 • Beycome of Florida LLC, Steven Kole...
Latitude Margaritaville
![331 COOL WATERS WAY, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,308 sq ft
|House
331 COOL WATERS WAY, DAYTONA BEACH, FL, ...
Community: Latitude Margaritaville
MLS 1224868 • RE/MAX Signature, Kimberly Sbordone...
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.
Indian River Colony Club
![1427 PATRIOT DR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|2 baths
|2,016 sq ft
|House
1427 PATRIOT DR, MELBOURNE, FL, 32940
Community: Indian River Colony Club
MLS 1073709 • Four Star Real Estate LLC, Robin St...
Latitude Margaritaville
![852 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124]()
2 beds
|3 baths
|1,748 sq ft
|House
852 CORAL REEF WAY, DAYTONA BEACH, FL, 3...
Community: Latitude Margaritaville
MLS 1224866 • Fathom Realty FL LLC, Adrienne Smit...
Latitude Margaritaville
![303 LATITUDE DR, DAYTONA BEACH, FL, 3212..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,308 sq ft
|House
303 LATITUDE DR, DAYTONA BEACH, FL, 3212...
Community: Latitude Margaritaville
MLS 1224852 • Bob Hodges and Sons Realty, Susan W...
Bridgewater at Viera
![2013 GREAT BELT CIR, MELBOURNE, FL, 3294..., Melbourne, FL 32940]()
2 beds
|2 baths
|1,876 sq ft
|House
2013 GREAT BELT CIR, MELBOURNE, FL, 3294...
Community: Bridgewater at Viera
MLS 1072333 • EXP Realty, LLC, David S Jelinek
Fountain View
![1356 FOUNTAIN VIEW ST, ORMOND BEACH, FL,..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,336 sq ft
|House
1356 FOUNTAIN VIEW ST, ORMOND BEACH, FL,...
Community: Fountain View
MLS 1224831 • D R Horton Realty of Central Florid...
Heritage Isle
![6957 FLORISTANA DR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|2 baths
|2,253 sq ft
|House
6957 FLORISTANA DR, MELBOURNE, FL, 32940
Community: Heritage Isle
MLS 1073578 • Misty Morrison Real Estate, Misty A...
Trilogy® Orlando
![108 MIST FLOWER LN, GROVELAND, FL, 34736, Groveland, FL 34736]()
2 beds
|2 baths
|1,900 sq ft
|House
108 MIST FLOWER LN, GROVELAND, FL, 34736
Community: Trilogy® Orlando
MLS G5110411 • COMMUNITY ELITE REALTY, Nancy Aitk...
Want to learn more about 55+ communities in Winter Park?
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(888) 625-4885
Summit Chase Villas
![12449 ORANGEWOOD CIR 17, TAVARES, FL, 32..., Tavares, FL 32778]()
2 beds
|2 baths
|918 sq ft
|Condo
12449 ORANGEWOOD CIR 17, TAVARES, FL, 32...
Community: Summit Chase Villas
MLS O6395077 • RP INVESTMENT REALTY LLC, Mike Ste...
Summit Greens
![2197 CALEDONIAN ST, CLERMONT, FL, 34711, Clermont, FL 34711]()
3 beds
|2 baths
|1,703 sq ft
|House
2197 CALEDONIAN ST, CLERMONT, FL, 34711
Community: Summit Greens
MLS O6395250 • BALDWIN PARK REALTY LLC, Brian Cir...
Scottish Highlands
![2218 ORKNEY DR, LEESBURG, FL, 34788, Leesburg, FL 34788]()
2 beds
|2 baths
|1,500 sq ft
|House
2218 ORKNEY DR, LEESBURG, FL, 34788
Community: Scottish Highlands
MLS G5110470 • ERA GRIZZARD REAL ESTATE, Cynthia ...
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.
Heritage Isle
![6770 RINGOLD ST, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
4 beds
|3 baths
|2,032 sq ft
|House
6770 RINGOLD ST, MELBOURNE, FL, 32940
Community: Heritage Isle
MLS 1072881 • RE/MAX Elite, Deborah L Tomczak
Lake Henry Estates
![558 PINNACLE DR, HAINES CITY, FL, 33844, Haines City, FL 33844]()
2 beds
|2 baths
|1,273 sq ft
|House
558 PINNACLE DR, HAINES CITY, FL, 33844
Community: Lake Henry Estates
MLS L4960781 • LIVE FLORIDA REALTY, Ramone Harris
The Lakes at Harmony
![3464 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773]()
2 beds
|2 baths
|1,404 sq ft
|House
3464 SAGEBRUSH ST, HARMONY, FL, 34773
Community: The Lakes at Harmony
MLS O6394042 • RESORT REALTY GROUP LTD INC, David...
Arlington Ridge
![27118 ROANOKE DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,713 sq ft
|House
27118 ROANOKE DR, LEESBURG, FL, 34748
Community: Arlington Ridge
MLS G5110376 • HARRISON REAL PROPERTY GROUP, Wend...
Spruce Creek Country Club
![14160 SE 85TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,238 sq ft
|Villa
14160 SE 85TH AVE, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS OM721734 • SELLSTATE NGR- SUMMERFIELD, Linda ...
Stonecrest
![17867 SE 115TH CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,597 sq ft
|House
17867 SE 115TH CIR, SUMMERFIELD, FL, 344...
Community: Stonecrest
MLS G5110081 • WORTH CLARK REALTY, Tamara Nelson-...
Venetian Bay
![3209 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|2,273 sq ft
|House
3209 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS NS1087782 • KINCAID REALTY, Samantha McHugh
The Villages®
![17431 SE 93RD RETFORD TER, THE VILLAGES,..., The Villages, FL 32162]()
2 beds
|2 baths
|1,160 sq ft
|Villa
17431 SE 93RD RETFORD TER, THE VILLAGES,...
Community: The Villages®
MLS R4910963 • BLACK TIE REAL ESTATE PROFESSIONAL...
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Solivita
![1309 LOMBARDI CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS O6395320 • REAL BROKER, LLC, Ken Pozek
The Villages®
![1253 GREENVILLE WAY, THE VILLAGES, FL, 3..., The Villages, FL 32162]()
3 beds
|2 baths
|1,967 sq ft
|House
1253 GREENVILLE WAY, THE VILLAGES, FL, 3...
Community: The Villages®
MLS G5109327 • REALTY EXECUTIVES IN THE VILLAGES,...
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?
2,414
homes
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REIN updates its listings on a daily basis. Data last updated: May 25, 2026.
This application does not include information on all of the properties available for sale at this time.
