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Winter Park, FL 55+ active adult communities & homes for sale - Page 20
98 communities near Winter Park
2,698 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
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
$300ks
- $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)
![Plantation at Leesburg]()
$100ks
- $300ks
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
Resale Only
|
55+ age-restricted
|
Built 1990 - 2024
|
2,224 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)
![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.
5 rating (8 reviews)
![Royal Highlands]()
$200ks
- $400ks
Royal Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2006
|
1,500 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
5 rating (3 reviews)
![Lake Ashton]()
$200ks
- $500ks
Lake Ashton, Lake Wales, FL
Resale Only
|
55+ age-restricted
|
Built 2002 - present
|
1,600 homes
$200ks
- $800ks
Grand Haven, Palm Coast, FL
New and Resale
|
Age-targeted
|
Built 1997 - present
|
1,901 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)
![Kings Ridge]()
$200ks
- $400ks
Kings Ridge, Clermont, FL
Resale Only
|
55+ age-restricted
|
Built 1995 - 2000
|
2,088 homes
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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
$300ks
- $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1980 - present
|
1,000 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
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
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
5 rating (1 reviews)
![Royal Harbor]()
$200ks
- $800ks
Royal Harbor, Tavares, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2008
|
755 homes
5 rating (8 reviews)
![Pennbrooke Fairways]()
<$100k
- $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1980 - 2004
|
1,200 homes
$200ks
- $1Ms
The Country Club of Mount..., Mount Dora, FL
Resale Only
|
Age-targeted
|
Built 1991 - 2005
|
827 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
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
$100ks
- $200ks
Scottish Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1983 - 1992
|
653 homes
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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)
![Del Webb Sunbridge]()
$400ks
- $800ks
Del Webb Sunbridge, St. Cloud, FL
New and Resale
|
55+ age-restricted
|
Built 2019 - present
|
1,300 homes
$300ks
- $600ks
Four Seasons at Orlando, Kissimmee, FL
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
557 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
$400ks
- $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1985 - present
|
976 homes
4.8 rating (6 reviews)
![Highland Lakes]()
$100ks
- $200ks
Highland Lakes, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1990 - 1999
|
938 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
$300ks
- $400ks
Gatherings of Lake Nona, Orlando, FL
New and Resale
|
55+ age-restricted
|
Built 2017 - present
|
216 homes
$400ks
- $1Ms
Del Webb at Viera, Melbourne, FL
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
1,300 homes
$100ks
- $300ks
Highland Fairways, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1983 - 1998
|
660 homes
$100ks
- $300ks
Lakeside Landings, Oxford, FL
New and Resale
|
Age-targeted
|
Built 2005 - present
|
700 homes
Want to learn more about 55+ communities in Winter Park?
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Questions? Call us:
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$200ks
- $400ks
The Lakes at Harmony, Harmony, FL
New and Resale
|
55+ age-restricted
|
Built 2016 - present
|
400 homes
1 rating (1 reviews)
![Sullivan Ranch]()
$200ks
- $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2020
|
692 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®
![571 TROY LOOP, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,927 sq ft
|House
571 TROY LOOP, THE VILLAGES, FL, 32162
Community: The Villages®
MLS OM730809 • KELLER WILLIAMS CORNERSTONE RE, Ca... • KELLER WILLIAMS CORNERSTONE RE
Del Webb Oasis
![13056 SANDCASTLE DR, WINTER GARDEN, FL, ..., Winter Garden, FL 34787]()
2 beds
|2 baths
|1,889 sq ft
|House
13056 SANDCASTLE DR, WINTER GARDEN, FL, ...
Community: Del Webb Oasis
MLS O6439937 • PULTE REALTY OF NORTH FLORIDA LLC,... • PULTE REALTY OF NORTH FLORIDA LLC
Cindy Certified
Cresswind at Victoria Gardens
![506 HERON POINT WAY, DELAND, FL, 32724, Deland, FL 32724]()
3 beds
|2 baths
|1,862 sq ft
|House
506 HERON POINT WAY, DELAND, FL, 32724
Community: Cresswind at Victoria Gardens
MLS V4951147 • BEACH LIFE REALTY, Michael Scott • BEACH LIFE REALTY
The Villages®
![934 ORCHID ST, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
3 beds
|2 baths
|1,495 sq ft
|House
934 ORCHID ST, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5117350 • REAL BROKER, LLC, Katy Kelly • REAL BROKER, LLC
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Spruce Creek South
![9619 SE 174TH PLACE RD, SUMMERFIELD, FL,..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,590 sq ft
|House
9619 SE 174TH PLACE RD, SUMMERFIELD, FL,...
Community: Spruce Creek South
MLS G5117172 • LPT REALTY, LLC, Dedee Messina • LPT REALTY, LLC
Lake Ashton
![5325 SNEAD DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884]()
3 beds
|2 baths
|1,833 sq ft
|House
5325 SNEAD DR, WINTER HAVEN, FL, 33884
Community: Lake Ashton
MLS TB8546364 • LA ROSA REALTY LLC, Francis Alvar... • LA ROSA REALTY LLC
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 O6439835 • COLDWELL BANKER REALTY, Edouard Sa... • COLDWELL BANKER REALTY
Huntington at Hunter's Ridge
![19 HUNTINGTON PL, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,837 sq ft
|House
19 HUNTINGTON PL, ORMOND BEACH, FL, 3217...
Community: Huntington at Hunter's Ridge
MLS 1086988 • EXP Realty, LLC, Justin Parsons • EXP Realty, LLC
The Villages®
![811 CLIFFORD CT, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|1,504 sq ft
|House
811 CLIFFORD CT, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5117466 • SALLY LOVE REAL ESTATE, Kim Coffer • SALLY LOVE 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.
The Reserve at Victoria
![859 LILIANA DR, DELAND, FL, 32724, Deland, FL 32724]()
3 beds
|3 baths
|2,178 sq ft
|House
859 LILIANA DR, DELAND, FL, 32724
Community: The Reserve at Victoria
MLS V4951109 • SOUTHERN EXCLUSIVE REALTY CORP, Tr... • SOUTHERN EXCLUSIVE REALTY CORP
Royal Highlands
![20743 QUEEN ALEXANDRA DR, LEESBURG, FL, ..., Leesburg, FL 34748]()
3 beds
|2 baths
|1,863 sq ft
|House
20743 QUEEN ALEXANDRA DR, LEESBURG, FL, ...
Community: Royal Highlands
MLS G5117307 • FLORIDA PLUS REALTY, LLC, Claire B... • FLORIDA PLUS REALTY, LLC
Halifax Plantation
![3005 GLIN CIR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,812 sq ft
|House
3005 GLIN CIR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
MLS 1230533 • RPJ Realty LLC, Erica Johnson • RPJ Realty LLC
Highland Lakes
![6631 BORG ST, LEESBURG, FL, 34748, Leesburg, FL 34748]()
MLS G5117293 • COLDWELL BANKER REALTY, Sara Suthe... • COLDWELL BANKER REALTY
Cindy Certified
Royal Harbor
![5090 INDIAN OCEAN LOOP, TAVARES, FL, 327..., Tavares, FL 32778]()
3 beds
|2 baths
|2,035 sq ft
|House
5090 INDIAN OCEAN LOOP, TAVARES, FL, 327...
Community: Royal Harbor
MLS G5117270 • RE/MAX TITANIUM GROUP, Kimberly Jo... • RE/MAX TITANIUM GROUP
Want to learn more about 55+ communities in Winter Park?
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Questions? Call us:
(888) 625-4885
Spruce Creek Country Club
![9588 SE 124TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,979 sq ft
|House
9588 SE 124TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek Country Club
MLS G5117464 • RE/MAX PREMIER REALTY LADY LK, Rob... • RE/MAX PREMIER REALTY LADY LK
Del Webb Sunbridge
![6117 CITRUS GROVE CT, ST CLOUD, FL, 3477..., St Cloud, FL 34771]()
3 beds
|2 baths
|2,084 sq ft
|House
6117 CITRUS GROVE CT, ST CLOUD, FL, 3477...
Community: Del Webb Sunbridge
MLS O6439701 • CHEVON EATON, Chevon Eaton • CHEVON EATON
Breakaway Trails
![23 CREEK BLUFF WAY, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,935 sq ft
|House
23 CREEK BLUFF WAY, ORMOND BEACH, FL, 32...
Community: Breakaway Trails
MLS 1230525 • Simply Real Estate, Nancy Eddy • Simply Real Estate
The Villages®
![17349 SE 76TH FLINTLOCK TER, THE VILLAGE..., The Villages, FL 32162]()
3 beds
|2 baths
|1,527 sq ft
|House
17349 SE 76TH FLINTLOCK TER, THE VILLAGE...
Community: The Villages®
MLS G5117440 • REALTY EXECUTIVES IN THE VILLAGES,... • 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.
Latitude Margaritaville
![663 LOST SHAKER WAY, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,464 sq ft
|House
663 LOST SHAKER WAY, DAYTONA BEACH, FL, ...
Community: Latitude Margaritaville
MLS 1230522 • Coldwell Banker Coast Realty, Kim B... • Coldwell Banker Coast Realty
Cresswind at Victoria Gardens
![1051 GARDENSHIRE LN, DELAND, FL, 32724, Deland, FL 32724]()
2 beds
|2 baths
|1,655 sq ft
|House
1051 GARDENSHIRE LN, DELAND, FL, 32724
Community: Cresswind at Victoria Gardens
MLS O6439190 • LOKATION, Gregory Buckley • LOKATION
Royal Harbor
![6063 ARMADA ST, TAVARES, FL, 32778, Tavares, FL 32778]()
MLS O6439278 • REALTY HUB, Aviel Ben Yishai • REALTY HUB
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 1230519 • Realty Hub, Aimee Aballo • Realty Hub
Venetian Bay
![3650 PONETA AVE, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168]()
5 beds
|4 baths
|3,017 sq ft
|House
3650 PONETA AVE, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
MLS NS1089187 • EXIT REAL ESTATE PROPERTY SOL, Ca... • EXIT REAL ESTATE PROPERTY SOL
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 1230517 • Realty Hub, Aimee Aballo • Realty Hub
Royal Harbor
![5370 INDIAN OCEAN LOOP, TAVARES, FL, 327..., Tavares, FL 32778]()
3 beds
|2 baths
|1,719 sq ft
|House
5370 INDIAN OCEAN LOOP, TAVARES, FL, 327...
Community: Royal Harbor
MLS G5117438 • HARRISON REAL PROPERTY GROUP, Aman... • HARRISON REAL PROPERTY GROUP
Want to learn more about 55+ communities in Winter Park?
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(888) 625-4885
Grand Haven
![42 W WATERSIDE PKWY, PALM COAST, FL, 321..., Palm Coast, FL 32137]()
2 beds
|2 baths
|1,611 sq ft
|House
42 W WATERSIDE PKWY, PALM COAST, FL, 321...
Community: Grand Haven
MLS FC321186 • REAL ESTATE SERVICES OF PC, Cheryl... • REAL ESTATE SERVICES OF PC
Solivita
![508 LAGO MATISSE ST, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759]()
3 beds
|2 baths
|1,807 sq ft
|House
508 LAGO MATISSE ST, KISSIMMEE, FL, 3475...
Community: Solivita
MLS A4705164 • SAVVY AVENUE, LLC, Moe Mossa • SAVVY AVENUE, LLC
The Villages®
![2149 SANDALWOOD PL, THE VILLAGES, FL, 32..., The Villages, FL 32163]()
3 beds
|2 baths
|1,395 sq ft
|Villa
2149 SANDALWOOD PL, THE VILLAGES, FL, 32...
Community: The Villages®
MLS TB8544152 • FLAT FEE MLS REALTY, Stephen Hach... • FLAT FEE MLS 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.
The Villages®
![17107 SE 93RD EXETER CT, THE VILLAGES, F..., The Villages, FL 32162]()
3 beds
|2 baths
|1,512 sq ft
|House
17107 SE 93RD EXETER CT, THE VILLAGES, F...
Community: The Villages®
MLS G5117316 • RE/MAX PREMIER REALTY, Matthew Rob... • RE/MAX PREMIER REALTY
The Villages®
![2109 GERARDO AVE, THE VILLAGES, FL, 3215..., The Villages, FL 32159]()
3 beds
|2 baths
|1,668 sq ft
|House
2109 GERARDO AVE, THE VILLAGES, FL, 3215...
Community: The Villages®
MLS G5117294 • COLDWELL BANKER REALTY, William Pe... • COLDWELL BANKER REALTY
Solivita
![448 SORRENTO RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5156975 • PELLEGO, LLC, Claudia Gimenez-Carl... • PELLEGO, LLC
Stonecrest
![12225 SE 173RD PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,475 sq ft
|House
12225 SE 173RD PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
MLS G5117375 • CHARLES RUTENBERG REALTY ORLANDO, ... • CHARLES RUTENBERG REALTY ORLANDO
Solivita
![320 SORRENTO RD, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5155741 • BORCHINI REALTY, Charles Borchini • BORCHINI REALTY
The Villages®
![17601 SE 81ST TIMBERWOOD TER, THE VILLAG..., The Villages, FL 32162]()
3 beds
|2 baths
|1,761 sq ft
|House
17601 SE 81ST TIMBERWOOD TER, THE VILLAG...
Community: The Villages®
MLS G5117399 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
The Villages®
![16878 SE 94TH SUNNYBROOK CIR, THE VILLAG..., The Villages, FL 32162]()
2 beds
|2 baths
|1,160 sq ft
|Villa
16878 SE 94TH SUNNYBROOK CIR, THE VILLAG...
Community: The Villages®
MLS G5117343 • DOWN HOME REALTY, LLLP, Mike Joy • DOWN HOME REALTY, LLLP
Cindy Certified
Want to learn more about 55+ communities in Winter Park?
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(888) 625-4885
Cindy Certified
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?
2,698
homes
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© 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: Oct 10, 2026.
This application does not include information on all of the properties available for sale at this time.
