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Winter Park, FL 55+ active adult communities & homes for sale - Page 25
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:
(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.
Pelican Bay Daytona Beach
![909 SEA DUCK DR, DAYTONA BEACH, FL, 3211..., Daytona Beach, FL 32119]()
3 beds
|3 baths
|2,534 sq ft
|House
909 SEA DUCK DR, DAYTONA BEACH, FL, 3211...
Community: Pelican Bay Daytona Beach
MLS 1230201 • Local Living Realty Group, Jennifer... • Local Living Realty Group
Trilogy® Orlando
![100 FLAME VINE WAY, GROVELAND, FL, 34736, Groveland, FL 34736]()
3 beds
|2 baths
|1,808 sq ft
|House
100 FLAME VINE WAY, GROVELAND, FL, 34736
Community: Trilogy® Orlando
MLS G5116962 • RE/MAX TITANIUM GROUP, Kristi Quic... • RE/MAX TITANIUM GROUP
Venetian Bay
![3659 CESI AVE, NEW SMYRNA BEACH, FL, 321..., New Smyrna Beach, FL 32168]()
4 beds
|3 baths
|2,119 sq ft
|House
3659 CESI AVE, NEW SMYRNA BEACH, FL, 321...
Community: Venetian Bay
MLS NS1089118 • EXIT REAL ESTATE PROPERTY SOL, Ca... • EXIT REAL ESTATE PROPERTY SOL
Park Place
![91 PARK PLACE CIR, PALM COAST, FL, 32164, Palm Coast, FL 32164]()
3 beds
|2 baths
|1,595 sq ft
|House
91 PARK PLACE CIR, PALM COAST, FL, 32164
Community: Park Place
MLS FC320999 • WEICHERT REALTORS HALLMARK, Brenna... • WEICHERT REALTORS HALLMARK
Solivita
![1389 LAMBARDI CT, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS TB8542522 • EXP REALTY LLC, Daniel Bustillo • EXP REALTY LLC
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Questions? Call us:
(888) 625-4885
American Village
![34 GREEN CIR 202, PALM COAST, FL, 32164, Palm Coast, FL 32164]()
1 beds
|1 baths
|659 sq ft
|Condo
34 GREEN CIR 202, PALM COAST, FL, 32164
Community: American Village
MLS FC321049 • TRADEMARK REALTY GROUP LLC, Steven... • TRADEMARK REALTY GROUP LLC
Pennbrooke Fairways
![639 NE COTTAGE PARK LN, LEESBURG, FL, 34..., Leesburg, FL 34748]()
1 beds
|1 baths
|560 sq ft
|Manufactured Home
639 NE COTTAGE PARK LN, LEESBURG, FL, 34...
Community: Pennbrooke Fairways
MLS G5117009 • PICKET FENCE REALTY LLC, David Leo • PICKET FENCE REALTY LLC
American Village
![34 GREEN CIR 201, PALM COAST, FL, 32164, Palm Coast, FL 32164]()
1 beds
|1 baths
|662 sq ft
|Condo
34 GREEN CIR 201, PALM COAST, FL, 32164
Community: American Village
MLS FC321032 • TRADEMARK REALTY GROUP LLC, Steven... • TRADEMARK REALTY GROUP LLC
Spruce Creek Country Club
![13490 SE 86TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,488 sq ft
|House
13490 SE 86TH CIR, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS G5116937 • RE/MAX PREMIER REALTY LADY LK, Dia... • RE/MAX PREMIER REALTY LADY LK
Lakeside Landings
![5408 ADMIRAL WAY 11-202, OXFORD, FL, 344..., Oxford, FL 34484]()
3 beds
|2 baths
|1,291 sq ft
|Condo
5408 ADMIRAL WAY 11-202, OXFORD, FL, 344...
Community: Lakeside Landings
MLS G5117090 • 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.
Pelican Bay Daytona Beach
![100 TERN CT, DAYTONA BEACH, FL, 32119, Daytona Beach, FL 32119]()
3 beds
|2 baths
|2,040 sq ft
|House
100 TERN CT, DAYTONA BEACH, FL, 32119
Community: Pelican Bay Daytona Beach
MLS 1230188 • Mary Lynn Realty, Mark Casel • Mary Lynn Realty
Solivita
![284 VESTRELLA DR, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5156191 • BORCHINI REALTY, Heather Hayes • BORCHINI REALTY
The Villages®
![2493 BACHMAN PATH, THE VILLAGES, FL, 321..., The Villages, FL 32162]()
3 beds
|2 baths
|2,117 sq ft
|House
2493 BACHMAN PATH, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5116973 • KELLER WILLIAMS CORNERSTONE RE, Ka... • KELLER WILLIAMS CORNERSTONE RE
The Villages®
![1207 PALMETTO DR, THE VILLAGES, FL, 3215..., The Villages, FL 32159]()
2 beds
|2 baths
|1,248 sq ft
|House
1207 PALMETTO DR, THE VILLAGES, FL, 3215...
Community: The Villages®
MLS G5116675 • FLORIDA FINE HOMES REALTY, LLC, Ji... • FLORIDA FINE HOMES REALTY, LLC
The Villages®
![756 ENDICOTT WAY, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
3 beds
|2 baths
|2,000 sq ft
|House
756 ENDICOTT WAY, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5116460 • LPT REALTY, LLC, Vickie Couture • LPT REALTY, LLC
Cindy Certified
Want to learn more about 55+ communities in Winter Park?
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Questions? Call us:
(888) 625-4885
The Villages®
![17362 SE 76TH FLINTLOCK TER, THE VILLAGE..., The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
17362 SE 76TH FLINTLOCK TER, THE VILLAGE...
Community: The Villages®
MLS OM731254 • CENTRAL CITY REALTY, Nathaniel Sul... • CENTRAL CITY REALTY
Halifax Plantation
![3087 SILVERMINES AVE, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,948 sq ft
|House
3087 SILVERMINES AVE, ORMOND BEACH, FL, ...
Community: Halifax Plantation
MLS O6436992 • ORCHARD BROKERAGE, LLC, Jamey Bris... • ORCHARD BROKERAGE, LLC
The Villages®
![3146 JACQUELINE WAY, THE VILLAGES, FL, 3..., The Villages, FL 32163]()
3 beds
|3 baths
|1,869 sq ft
|House
3146 JACQUELINE WAY, THE VILLAGES, FL, 3...
Community: The Villages®
MLS G5116975 • WORTH CLARK REALTY, Lisbeth Cline • WORTH CLARK REALTY
American Village
![34 GREEN CIR 102, PALM COAST, FL, 32164, Palm Coast, FL 32164]()
1 beds
|1 baths
|650 sq ft
|Condo
34 GREEN CIR 102, PALM COAST, FL, 32164
Community: American Village
MLS FC321009 • TRADEMARK REALTY GROUP LLC, Steven... • TRADEMARK REALTY GROUP LLC
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.
Cresswind at Victoria Gardens
![1649 VICTORIA GARDENS DR, DELAND, FL, 32..., Deland, FL 32724]()
2 beds
|2 baths
|1,933 sq ft
|House
1649 VICTORIA GARDENS DR, DELAND, FL, 32...
Community: Cresswind at Victoria Gardens
MLS O6435816 • BETTER HOMES AND GARDENS REAL ESTA... • BETTER HOMES AND GARDENS REAL ESTATE MANN GLOBAL P
Stonecrest
![11337 SE 175TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,502 sq ft
|House
11337 SE 175TH PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
MLS OM730839 • KELLER WILLIAMS CORNERSTONE RE, Ri... • KELLER WILLIAMS CORNERSTONE RE
Cindy Certified
The Villages®
![2445 BUTTONWOOD RUN, THE VILLAGES, FL, 3..., The Villages, FL 32162]()
4 beds
|2 baths
|2,053 sq ft
|House
2445 BUTTONWOOD RUN, THE VILLAGES, FL, 3...
Community: The Villages®
MLS G5117036 • SALLY LOVE REAL ESTATE, Kim Coffer • SALLY LOVE REAL ESTATE
Cindy Certified
Latitude Margaritaville
![329 POP TOP LN, DAYTONA BEACH, FL, 32124, Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,308 sq ft
|House
329 POP TOP LN, DAYTONA BEACH, FL, 32124
Community: Latitude Margaritaville
MLS 1230147 • Realty Hub, Robyn Beckett Young • Realty Hub
The Villages®
![1670 SAINT JAMES CIR, THE VILLAGES, FL, ..., The Villages, FL 32162]()
4 beds
|2 baths
|3,172 sq ft
|House
1670 SAINT JAMES CIR, THE VILLAGES, FL, ...
Community: The Villages®
MLS V4950915 • RE/MAX AEROSPACE REALTY, Nicholas ... • RE/MAX AEROSPACE REALTY
Want to learn more about 55+ communities in Winter Park?
55places can help!
Questions? Call us:
(888) 625-4885
Solivita
![133 GRAND CANAL DR, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5155979 • BORCHINI REALTY, Cherie Pontes • BORCHINI REALTY
Del Webb Oasis
![13355 SUNNY RETREAT LN, WINTER GARDEN, F..., Winter Garden, FL 34787]()
3 beds
|3 baths
|2,710 sq ft
|House
13355 SUNNY RETREAT LN, WINTER GARDEN, F...
Community: Del Webb Oasis
MLS O6436813 • PREMIER SOTHEBYS INT'L REALTY, Joh... • PREMIER SOTHEBYS INT'L REALTY
Spruce Creek South
![17624 SE 108TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,144 sq ft
|House
17624 SE 108TH TER, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
MLS TB8542986 • LPT REALTY, LLC, Krystal Rooney • LPT REALTY, LLC
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
VillageWalk at Lake Nona
![11962 GENNARO LN, ORLANDO, FL, 32827, Orlando, FL 32827]()
3 beds
|2 baths
|2,005 sq ft
|House
11962 GENNARO LN, ORLANDO, FL, 32827
Community: VillageWalk at Lake Nona
MLS O6436693 • EXP REALTY LLC, Ginny Adkins LLC • EXP REALTY LLC
Cindy Certified
Sullivan Ranch
![30238 TOKARA TER, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
4 beds
|2 baths
|2,065 sq ft
|House
30238 TOKARA TER, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
MLS V4950784 • COLDWELL BANKER REALTY, Daniel Har... • COLDWELL BANKER REALTY
Latitude Margaritaville
![215 HANG LOOSE WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,160 sq ft
|House
215 HANG LOOSE WAY, DAYTONA BEACH, FL, 3...
Community: Latitude Margaritaville
MLS 1230133 • Realty Hub, Aimee Aballo • Realty Hub
Lake Ashton
![4063 BIRKDALE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859]()
2 beds
|2 baths
|1,530 sq ft
|House
4063 BIRKDALE DR, LAKE WALES, FL, 33859
Community: Lake Ashton
MLS G5116808 • IAD REAL ESTATE, Juan Quiles Marre... • IAD REAL ESTATE
Del Webb Orlando
![333 NAVARRA LN, DAVENPORT, FL, 33837, Davenport, FL 33837]()
3 beds
|2 baths
|2,028 sq ft
|House
333 NAVARRA LN, DAVENPORT, FL, 33837
Community: Del Webb Orlando
MLS S5156401 • EXP REALTY LLC, Juan Melo • EXP REALTY LLC
Plantation at Leesburg
![25735 GLEN EAGLE DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,652 sq ft
|House
25735 GLEN EAGLE DR, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS O6436929 • MAXLIFE REALTY LLC, Ryan Solberg • MAXLIFE REALTY LLC
Want to learn more about 55+ communities in Winter Park?
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(888) 625-4885
Alamanda Key
![668 LORELEI AVE, MELBOURNE, FL, 32901, Melbourne, FL 32901]()
3 beds
|2 baths
|1,630 sq ft
|House
668 LORELEI AVE, MELBOURNE, FL, 32901
Community: Alamanda Key
MLS 1086029 • Stanley Homes LLC, Andrea L Calhoun • Stanley Homes LLC
Trilogy® Orlando
![134 FLAME VINE WAY, GROVELAND, FL, 34736, Groveland, FL 34736]()
2 beds
|2 baths
|1,556 sq ft
|House
134 FLAME VINE WAY, GROVELAND, FL, 34736
Community: Trilogy® Orlando
MLS G5117000 • REALTY PROFESSIONALS OF FL,LLC, Ha... • REALTY PROFESSIONALS OF FL,LLC
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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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.
