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Winter Park, FL 55+ active adult communities & homes for sale - Page 32
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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$300ks
- $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1980 - present
|
1,000 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
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
- $900ks
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.
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
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
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$100ks
- $200ks
Scottish Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1983 - 1992
|
653 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
4.8 rating (6 reviews)
![Highland Lakes]()
$100ks
- $200ks
Highland Lakes, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1990 - 1999
|
938 homes
$400ks
- $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1985 - present
|
976 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
$100ks
- $300ks
Highland Fairways, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1983 - 1998
|
660 homes
$400ks
- $1Ms
Del Webb at Viera, Melbourne, FL
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
1,300 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?
55places can help!
Questions? Call us:
(888) 625-4885
$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®
![628 BERMUDEZ CT, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,787 sq ft
|Villa
628 BERMUDEZ CT, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5116278 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
Heritage Hills
![3530 FAIRWATERS CT D, CLERMONT, FL, 3471..., Clermont, FL 34711]()
2 beds
|2 baths
|1,374 sq ft
|Villa
3530 FAIRWATERS CT D, CLERMONT, FL, 3471...
Community: Heritage Hills
MLS G5116204 • KELLER WILLIAMS ELITE PARTNERS III... • KELLER WILLIAMS ELITE PARTNERS III REALTY
Cindy Certified
The Villages®
![1674 GOVAN PL, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,368 sq ft
|Villa
1674 GOVAN PL, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5116377 • WORTH CLARK REALTY, Scott Hubbard • WORTH CLARK REALTY
Plantation Bay Golf & Country Club
![11 MAGNOLIA DR 11, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
2 beds
|2 baths
|1,300 sq ft
|Condo
11 MAGNOLIA DR 11, ORMOND BEACH, FL, 321...
Community: Plantation Bay Golf & Country Club
MLS FC320539 • REALTY EXECUTIVES OCEANSIDE, Audre... • REALTY EXECUTIVES OCEANSIDE
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The Villages®
![9671 SE 168TH MAPLESONG LN, THE VILLAGES..., The Villages, FL 32162]()
3 beds
|2 baths
|1,557 sq ft
|House
9671 SE 168TH MAPLESONG LN, THE VILLAGES...
Community: The Villages®
MLS O6433003 • BEYCOME OF FLORIDA LLC, Steven Kol... • BEYCOME OF FLORIDA LLC
Cindy Certified
Latitude Margaritaville
![521 DAIQUIRI PL, DAYTONA BEACH, FL, 3212..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,464 sq ft
|House
521 DAIQUIRI PL, DAYTONA BEACH, FL, 3212...
Community: Latitude Margaritaville
MLS 1229577 • Bob Hodges and Sons Realty, Sandra ... • Bob Hodges and Sons Realty
The Villages®
![16840 SE 97TH WILDWOOD CT, THE VILLAGES,..., The Villages, FL 32162]()
3 beds
|2 baths
|1,527 sq ft
|House
16840 SE 97TH WILDWOOD CT, THE VILLAGES,...
Community: The Villages®
MLS G5116354 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
Trilogy® Orlando
![107 BALMY COAST RD, GROVELAND, FL, 34736, Groveland, FL 34736]()
3 beds
|3 baths
|2,756 sq ft
|House
107 BALMY COAST RD, GROVELAND, FL, 34736
Community: Trilogy® Orlando
MLS O6430958 • REAL PROPERTY INTERNATIONAL, Irma ... • REAL PROPERTY INTERNATIONAL
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
Breakaway Trails
![16 CRESCENT LAKE WAY, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,552 sq ft
|House
16 CRESCENT LAKE WAY, ORMOND BEACH, FL, ...
Community: Breakaway Trails
MLS 1229566 • Selby Realty, Inc., Kyle Selby • Selby Realty, Inc.
Spruce Creek Country Club
![9317 SE 124TH PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
2 beds
|2 baths
|1,906 sq ft
|House
9317 SE 124TH PL, SUMMERFIELD, FL, 34491
Community: Spruce Creek Country Club
MLS OM730075 • MAGNOLIA HOMES AND LAND LLC, Seth ... • MAGNOLIA HOMES AND LAND LLC
Solivita
![163 OLYMPUS WAY, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5154866 • PELLEGO, LLC, Stan Wilson • PELLEGO, LLC
Solivita
![970 SAN RAPHAEL ST, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5154400 • PELLEGO, LLC, Stan Wilson • PELLEGO, LLC
Legacy of Leesburg
![27336 PINE STRAW RD, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,765 sq ft
|House
27336 PINE STRAW RD, LEESBURG, FL, 34748
Community: Legacy of Leesburg
MLS G5116219 • DOUBLE MM DEVELOPMENT, LLC, Mo McL... • DOUBLE MM DEVELOPMENT, LLC
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Spruce Creek South
![17989 SE 106TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,450 sq ft
|House
17989 SE 106TH CT, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
MLS G5115640 • HANSON REAL ESTATE GROUP, INC., Je... • HANSON REAL ESTATE GROUP, INC.
Royal Highlands
![20512 QUEEN ALEXANDRA DR, LEESBURG, FL, ..., Leesburg, FL 34748]()
3 beds
|2 baths
|2,008 sq ft
|House
20512 QUEEN ALEXANDRA DR, LEESBURG, FL, ...
Community: Royal Highlands
MLS G5116320 • VANGIE BERRY SIGNATURE REALTY, Ang... • VANGIE BERRY SIGNATURE REALTY
Twin Lakes
![2699 MIDSWEET AVE, ST CLOUD, FL, 34772, St Cloud, FL 34772]()
MLS S5155346 • WEICHERT REALTORS HALLMARK PRO, Sh... • WEICHERT REALTORS HALLMARK PRO
The Villages®
![1218 SANTOS PL, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,319 sq ft
|House
1218 SANTOS PL, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5116335 • 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.
The Villages®
![3425 CARBONDALE CT, THE VILLAGES, FL, 32..., The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
3425 CARBONDALE CT, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5116325 • RE/MAX SELECT PARTNERS, Stephanie ... • RE/MAX SELECT PARTNERS
Cresswind DeLand
![1193 CRESSWIND BLVD, DELAND, FL, 32724, Deland, FL 32724]()
3 beds
|3 baths
|2,289 sq ft
|House
1193 CRESSWIND BLVD, DELAND, FL, 32724
Community: Cresswind DeLand
MLS W7888486 • MALTBIE REALTY GROUP, Bill Maltbie • MALTBIE REALTY GROUP
Stonecrest
![17566 SE 112TH AVE, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|2 baths
|2,000 sq ft
|House
17566 SE 112TH AVE, SUMMERFIELD, FL, 344...
Community: Stonecrest
MLS G5116324 • BLACK TIE REALTY, INC., Alex Scopi... • BLACK TIE REALTY, INC.
The Villages®
![1049 JACKSON ST, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,187 sq ft
|Villa
1049 JACKSON ST, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5116316 • LPT REALTY, LLC, Dave Monty • LPT REALTY, LLC
Cindy Certified
Venetian Bay
![3006 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|1,614 sq ft
|House
3006 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS NS1088960 • KELLER WILLIAMS RLTY FL. PARTN, W... • KELLER WILLIAMS RLTY FL. PARTN
Plantation Bay Golf & Country Club
![1244 HARWICK LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,948 sq ft
|House
1244 HARWICK LN, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS O6428051 • O'BRIEN REAL ESTATE LLC, Patrick O... • O'BRIEN REAL ESTATE LLC
Want to learn more about 55+ communities in Winter Park?
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Questions? Call us:
(888) 625-4885
Cindy Certified
Cindy Certified
Trilogy® Orlando
![78 BAYOU BEND RD, GROVELAND, FL, 34736, Groveland, FL 34736]()
2 beds
|2 baths
|1,305 sq ft
|House
78 BAYOU BEND RD, GROVELAND, FL, 34736
Community: Trilogy® Orlando
MLS G5116290 • COLDWELL BANKER HUBBARD HANSEN, Pa... • COLDWELL BANKER HUBBARD HANSEN
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
![142 PORTOFINO BLVD, NEW SMYRNA BEACH, FL..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|2,456 sq ft
|House
142 PORTOFINO BLVD, NEW SMYRNA BEACH, FL...
Community: Venetian Bay
MLS V4950638 • RE/MAX SIGNATURE, Mike Fiscina • RE/MAX SIGNATURE
Lakeside Landings
![5336 EDGEWATER WAY 11, OXFORD, FL, 34484, Oxford, FL 34484]()
3 beds
|2 baths
|1,291 sq ft
|Condo
5336 EDGEWATER WAY 11, OXFORD, FL, 34484
Community: Lakeside Landings
MLS O6431511 • GR REALTY EXPERTS, Gilbert Rivera • GR REALTY EXPERTS
Arlington Ridge
![4419 BENT CREEK LN, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|3 baths
|2,333 sq ft
|House
4419 BENT CREEK LN, LEESBURG, FL, 34748
Community: Arlington Ridge
MLS O6432325 • REAL BROKER, LLC, Brian Batiz Sala... • REAL BROKER, LLC
Esplanade at Westview
![5676 NEVIS TER, KISSIMMEE, FL, 34758, Kissimmee, FL 34758]()
3 beds
|3 baths
|2,296 sq ft
|House
5676 NEVIS TER, KISSIMMEE, FL, 34758
Community: Esplanade at Westview
MLS O6432452 • TAYLOR MORRISON REALTY OF FLORIDA ... • TAYLOR MORRISON REALTY OF FLORIDA INC
Grand Haven
![92 LAGARE ST, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
MLS FC319775 • COASTAL GATEWAY REAL ESTATE GR, An... • COASTAL GATEWAY REAL ESTATE GR
The Villages®
![2706 MORVEN PARK WAY, THE VILLAGES, FL, ..., The Villages, FL 32162]()
2 beds
|2 baths
|1,248 sq ft
|House
2706 MORVEN PARK WAY, THE VILLAGES, FL, ...
Community: The Villages®
MLS G5116185 • FLAMINGO REAL ESTATE & MNGMT, Robb... • FLAMINGO REAL ESTATE & MNGMT
Esplanade at Westview
![4364 CURACAO PL, KISSIMMEE, FL, 34758, Kissimmee, FL 34758]()
3 beds
|3 baths
|3,004 sq ft
|House
4364 CURACAO PL, KISSIMMEE, FL, 34758
Community: Esplanade at Westview
MLS O6432402 • TAYLOR MORRISON REALTY OF FLORIDA ... • TAYLOR MORRISON REALTY OF FLORIDA INC
Carillon Lakes
![3007 BELLFLOWER WAY, LAKELAND, FL, 33811, Lakeland, FL 33811]()
3 beds
|3 baths
|1,846 sq ft
|House
3007 BELLFLOWER WAY, LAKELAND, FL, 33811
Community: Carillon Lakes
MLS L4964032 • REMAX EXPERTS, Maria Santillo • REMAX EXPERTS
Want to learn more about 55+ communities in Winter Park?
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Venetian Bay
![477 LUNA BELLA LN, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168]()
5 beds
|4 baths
|3,002 sq ft
|House
477 LUNA BELLA LN, NEW SMYRNA BEACH, FL,...
Community: Venetian Bay
MLS NS1088899 • WATSON REALTY CORP, Lainy McKain • WATSON REALTY CORP
Four Seasons at Orlando
![1667 KEY BAY TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747]()
2 beds
|2 baths
|1,437 sq ft
|Villa
1667 KEY BAY TRL, KISSIMMEE, FL, 34747
Community: Four Seasons at Orlando
MLS O6431972 • CHARLES RUTENBERG REALTY ORLANDO, ... • CHARLES RUTENBERG REALTY ORLANDO
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.
