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Winter Park, FL 55+ active adult communities & homes for sale - Page 3
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
5 rating (8 reviews)
![Royal Highlands]()
$200ks
- $400ks
Royal Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2006
|
1,500 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.
$100ks
- $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only
|
Age-targeted
|
Built 1980 - 2006
|
1,806 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
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
$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 (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
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$300ks
- $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1980 - present
|
1,000 homes
5 rating (8 reviews)
![Kings Ridge]()
$200ks
- $400ks
Kings Ridge, Clermont, FL
Resale Only
|
55+ age-restricted
|
Built 1995 - 2000
|
2,088 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.
5 rating (1 reviews)
![Royal Harbor]()
$200ks
- $800ks
Royal Harbor, Tavares, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2008
|
755 homes
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 (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
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
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$100ks
- $200ks
Scottish Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1983 - 1992
|
653 homes
$300ks
- $600ks
Four Seasons at Orlando, Kissimmee, FL
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
557 homes
4.8 rating (6 reviews)
![Highland Lakes]()
$100ks
- $200ks
Highland Lakes, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1990 - 1999
|
938 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
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
$400ks
- $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1985 - present
|
976 homes
$300ks
- $400ks
Gatherings of Lake Nona, Orlando, FL
New and Resale
|
55+ age-restricted
|
Built 2017 - present
|
216 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
- $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?
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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
$100ks
- $200ks
Foxwood Lake Estates, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1982 - 1987
|
545 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.
New
Plantation Bay Golf & Country Club
![34 TREETOP CIR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|3 baths
|2,767 sq ft
|House
34 TREETOP CIR, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS 1231532 • Realty Pros Assured, Aimee Haase • Realty Pros Assured
New
![16437 FERNRIDGE ST, CLERMONT, FL, 34714, Clermont, FL 34714]()
Cindy Certified
New
Cresswind DeLand
![1209 BRUSH CREEK DR, DELAND, FL, 32724, Deland, FL 32724]()
2 beds
|2 baths
|2,029 sq ft
|House
1209 BRUSH CREEK DR, DELAND, FL, 32724
Community: Cresswind DeLand
MLS W7890157 • MALTBIE REALTY GROUP, Bill Maltbie • MALTBIE REALTY GROUP
New
![988 CAMBRIDGE DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33881]()
Cindy Certified
New
Pennbrooke Fairways
![1145 EAGLES LNDG, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,639 sq ft
|House
1145 EAGLES LNDG, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS G5118606 • VISIONARY PROPERTIES INC, Mary Bak... • VISIONARY PROPERTIES INC
Want to learn more about 55+ communities in Winter Park?
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Questions? Call us:
(888) 625-4885
New
Lakeside Landings
![10371 ADDISON SHORE WAY, OXFORD, FL, 344..., Oxford, FL 34484]()
4 beds
|3 baths
|2,016 sq ft
|House
10371 ADDISON SHORE WAY, OXFORD, FL, 344...
Community: Lakeside Landings
MLS G5118677 • DOWN HOME REALTY, LLLP, Kristen Pi... • DOWN HOME REALTY, LLLP
New
Summer Trees
![115 CYPRESS POND RD, PORT ORANGE, FL, 32..., Port Orange, FL 32128]()
2 beds
|2 baths
|1,340 sq ft
|House
115 CYPRESS POND RD, PORT ORANGE, FL, 32...
Community: Summer Trees
MLS 1231533 • Best Way Realty of Volusia LLC, Jim... • Best Way Realty of Volusia LLC
New
Legacy of Leesburg
![5127 AURORA DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|2,386 sq ft
|House
5127 AURORA DR, LEESBURG, FL, 34748
Community: Legacy of Leesburg
MLS G5118740 • HARRISON REAL PROPERTY GROUP, Aman... • HARRISON REAL PROPERTY GROUP
New
![11 HONEYBELL WAY, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
Cindy Certified
New
The Villages®
![3254 ZIPPERER WAY, THE VILLAGES, FL, 321..., The Villages, FL 32163]()
3 beds
|2 baths
|1,654 sq ft
|House
3254 ZIPPERER WAY, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5118513 • RE/MAX PREMIER REALTY, Matthew Rob... • RE/MAX PREMIER 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.
New
![34024 SKY BLOSSOM CIR, LEESBURG, FL, 347..., Leesburg, FL 34788]()
Cindy Certified
New
Sandpiper Golf & Country Club
![6303 EGRET DR, LAKELAND, FL, 33809, Lakeland, FL 33809]()
2 beds
|2 baths
|1,335 sq ft
|House
6303 EGRET DR, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS L4965575 • DALTON WADE INC, Carolyn Christian • DALTON WADE INC
New
The Villages®
![2182 KAYLEE DR, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,499 sq ft
|House
2182 KAYLEE DR, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5118675 • ERA GRIZZARD REAL ESTATE, Holly We... • ERA GRIZZARD REAL ESTATE
New
Spruce Creek South
![10255 SE 178TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,248 sq ft
|House
10255 SE 178TH PL, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
MLS OM733553 • RE/MAX FOXFIRE - SUMMERFIELD, Eile... • RE/MAX FOXFIRE - SUMMERFIELD
New
Pelican Bay Daytona Beach
![172 BERMUDA PETREL CT, DAYTONA BEACH, FL..., Daytona Beach, FL 32119]()
3 beds
|3 baths
|2,010 sq ft
|House
172 BERMUDA PETREL CT, DAYTONA BEACH, FL...
Community: Pelican Bay Daytona Beach
MLS 1231529 • A.H. Stone & Associates Inc, Sam Na... • A.H. Stone & Associates Inc
New
![2693 PORTADOWN ST, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
Cindy Certified
Want to learn more about 55+ communities in Winter Park?
55places can help!
Questions? Call us:
(888) 625-4885
New
The Country Club of Mount Dora
![8021 SAINT JAMES WAY, MOUNT DORA, FL, 32..., Mount Dora, FL 32757]()
3 beds
|2 baths
|2,371 sq ft
|House
8021 SAINT JAMES WAY, MOUNT DORA, FL, 32...
Community: The Country Club of Mount Dora
MLS G5118635 • ERA GRIZZARD REAL ESTATE, Loretta ... • ERA GRIZZARD REAL ESTATE
New
Del Webb Lakehaven
![15559 PEACEFUL PINES ALY, CLERMONT, FL, ..., Clermont, FL 34714]()
5 beds
|3 baths
|2,603 sq ft
|House
15559 PEACEFUL PINES ALY, CLERMONT, FL, ...
Community: Del Webb Lakehaven
MLS O6447753 • PULTE REALTY OF NORTH FLORIDA LLC,... • PULTE REALTY OF NORTH FLORIDA LLC
New
Pennbrooke Fairways
![1040 EAGLES LNDG, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,752 sq ft
|House
1040 EAGLES LNDG, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS G5118617 • GOLDKEY REAL ESTATE PARTNERS LLC, ... • GOLDKEY REAL ESTATE PARTNERS LLC
New
The Villages®
![4398 PEZZULLO CIR, THE VILLAGES, FL, 321..., The Villages, FL 32163]()
4 beds
|3 baths
|3,325 sq ft
|House
4398 PEZZULLO CIR, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5118687 • RE/MAX PREMIER REALTY, Tammy Freil... • RE/MAX PREMIER 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.
New
![15302 HONEYBELL DR, WINTER GARDEN, FL, 3..., Winter Garden, FL 34787]()
Cindy Certified
New
Twin Lakes
![5031 DANCY LN, ST CLOUD, FL, 34772, St Cloud, FL 34772]()
MLS S5158568 • WEICHERT REALTORS HALLMARK PRO, Sh... • WEICHERT REALTORS HALLMARK PRO
New
Pennbrooke Fairways
![752 OLD OAKS LN, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,620 sq ft
|House
752 OLD OAKS LN, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS G5118563 • CENTURY 21 ALTON CLARK, Steven San... • CENTURY 21 ALTON CLARK
New
Del Webb at Viera
![9190 WANDER TRL, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
4 beds
|4 baths
|2,799 sq ft
|House
9190 WANDER TRL, MELBOURNE, FL, 32940
Community: Del Webb at Viera
MLS 1089361 • Aqua Realty Services, LLC, Alexis T... • Aqua Realty Services, LLC
New
Plantation at Leesburg
![4952 HERON RUN CIR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,289 sq ft
|House
4952 HERON RUN CIR, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5118709 • CENTURY 21 MYERS ROSE REALTY, Mary... • CENTURY 21 MYERS ROSE REALTY
New
Twin Lakes
![2632 MEADOWEDGE LOOP, ST CLOUD, FL, 3477..., St Cloud, FL 34772]()
3 beds
|3 baths
|2,335 sq ft
|House
2632 MEADOWEDGE LOOP, ST CLOUD, FL, 3477...
Community: Twin Lakes
MLS S5158969 • WEICHERT REALTORS HALLMARK PRO, Sh... • WEICHERT REALTORS HALLMARK PRO
New
Breakaway Trails
![12 BROOK CREST WAY, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174]()
4 beds
|4 baths
|2,976 sq ft
|House
12 BROOK CREST WAY, ORMOND BEACH, FL, 32...
Community: Breakaway Trails
MLS V4951632 • REALTY PROS ASSURED, Patti McKinle... • REALTY PROS ASSURED
Want to learn more about 55+ communities in Winter Park?
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(888) 625-4885
New
Twin Lakes
![2457 DREAM HOME CT, ST CLOUD, FL, 34772, St Cloud, FL 34772]()
2 beds
|2 baths
|1,346 sq ft
|House
2457 DREAM HOME CT, ST CLOUD, FL, 34772
Community: Twin Lakes
MLS S5158573 • WEICHERT REALTORS HALLMARK PRO, Sh... • WEICHERT REALTORS HALLMARK PRO
New
Solivita
![637 VOLTERRA BLVD, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS O6446206 • KELLER WILLIAMS WINTER PARK, Betsy... • KELLER WILLIAMS WINTER PARK
New
The Villages®
![1103 MIONA SHORES DR, THE VILLAGES, FL, ..., The Villages, FL 32162]()
4 beds
|3 baths
|4,272 sq ft
|House
1103 MIONA SHORES DR, THE VILLAGES, FL, ...
Community: The Villages®
MLS G5118628 • SALLY LOVE REAL ESTATE, Sally Love • 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.
New
Spruce Creek Country Club
![9116 SE 135TH LN, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
2 beds
|1 baths
|943 sq ft
|House
9116 SE 135TH LN, SUMMERFIELD, FL, 34491
Community: Spruce Creek Country Club
MLS OM733500 • GUS GALLOWAY REALTY INC, Lisa Rock... • GUS GALLOWAY REALTY INC
New
The Villages®
![2334 AMBLER CIR, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|3 baths
|2,243 sq ft
|House
2334 AMBLER CIR, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5118568 • RE/MAX PREMIER REALTY, Guy William... • RE/MAX PREMIER REALTY
New
The Villages®
![1647 DURAN DR, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,121 sq ft
|Villa
1647 DURAN DR, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5118645 • RE/MAX FOXFIRE - SUMMERFIELD, Robe... • RE/MAX FOXFIRE - SUMMERFIELD
New
Sandpiper Golf & Country Club
![6464 SANDPIPERS DR 2, LAKELAND, FL, 3380..., Lakeland, FL 33809]()
2 beds
|1 baths
|872 sq ft
|House
6464 SANDPIPERS DR 2, LAKELAND, FL, 3380...
Community: Sandpiper Golf & Country Club
MLS R4912103 • DYW LLC, Yvonne Wherrett • DYW LLC
New
The Villages®
![2155 BALDWIN RUN, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
3 beds
|2 baths
|1,488 sq ft
|House
2155 BALDWIN RUN, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5117738 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
New
![5362 WHISPERING GARDEN WAY, CLERMONT, FL..., Clermont, FL 34714]()
Cindy Certified
New
Pennbrooke Fairways
![32802 CROOKED OAKS LN, LEESBURG, FL, 347..., Leesburg, FL 34748]()
3 beds
|2 baths
|1,604 sq ft
|House
32802 CROOKED OAKS LN, LEESBURG, FL, 347...
Community: Pennbrooke Fairways
MLS G5118657 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
New
The Villages®
![780 ADRIENNE WAY, THE VILLAGES, FL, 3216..., The Villages, FL 32163]()
3 beds
|2 baths
|1,357 sq ft
|House
780 ADRIENNE WAY, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5118685 • LPT REALTY, LLC, Michele Hart • LPT REALTY, LLC
Want to learn more about 55+ communities in Winter Park?
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(888) 625-4885
New
![13345 BEEBE ALY, ORLANDO, FL, 32827, Orlando, FL 32827]()
Cindy Certified
New
![2579 CLEAR NIGHT AVE, KISSIMMEE, FL, 347..., Kissimmee, FL 34744]()
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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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.
