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Winter Park, FL 55+ active adult communities & homes for sale - Page 3
97 communities near Winter Park
2,229 homes near Winter Park
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$300ks
- $500ks
Alamanda Key, Melbourne, FL
Resale Only
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55+ age-restricted
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Built 2005 - 2021
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300 homes
$100ks
- $300ks
Baytree, Tavares, FL
Resale Only
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55+ age-restricted
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Built 1990 - 2003
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221 homes
$300ks
- $400ks
Freedom Homes at Grand Re..., Bunnell, FL
Resale Only
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55+ age-restricted
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Built 2018 - 2022
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55 homes
$100ks
- $200ks
Oakview, Winter Haven, FL
Resale Only
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55+ age-restricted
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Built 1988 - 1999
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48 homes
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2 rating (1 reviews)
![Heritage Landings]()
$200ks
- $300ks
Heritage Landings, Lakeland, FL
New Construction
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55+ age-restricted
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Built 2017 - 2020
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65 homes
$200ks
Carlsberg Estates on Lake..., Lake Wales, FL
Resale Only
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55+ age-restricted
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Built 1998 - 2006
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162 homes
$700ks
- $1Ms
Enclave at VillageWalk, Orlando, FL
Resale Only
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Age-targeted
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Built 2015 - 2021
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144 homes
$200ks
- $300ks
Royal Palm, Port Orange, FL
Resale Only
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55+ age-restricted
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Built 2002 - 2016
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458 homes
$400ks
Serenity Reserve, St. Cloud, FL
Resale Only
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55+ age-restricted
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Built 2016 - 2020
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85 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.
$200ks
- $300ks
Preserve at Lakeside Land..., Winter Haven, FL
Resale Only
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55+ age-restricted
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Built 2016 - 2019
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44 homes
$100ks
- $200ks
The Wellington, Winter Haven, FL
Resale Only
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55+ age-restricted
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Built 1969 - 1981
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77 homes
5 rating (1 reviews)
![Cypress Lakes]()
$100ks
Cypress Lakes, Lakeland, FL
Resale Only
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55+ age-restricted
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Built 1987 - 2016
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1,604 homes
$100ks
- $200ks
Poinsettia Heights, Winter Haven, FL
Resale Only
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55+ age-restricted
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Built 1978 - 2000
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49 homes
$300ks
- $400ks
Ormond Renaissance, Ormond Beach, FL
New Construction
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55+ age-restricted
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Built 2016 - present
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280 homes
$300ks
- $500ks
Lennar at Sanctuary at We..., Clermont, FL
New Construction
|
55+ age-restricted
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Built 2025 - 2026
|
203 homes
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5 rating (4 reviews)
![Grand Isle]()
$400ks
Grand Isle, Melbourne, FL
Resale Only
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55+ age-restricted
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Built 2002 - 2006
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336 homes
New
The Villages®
![17648 SE 93RD BUTLER CT, THE VILLAGES, F..., The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
17648 SE 93RD BUTLER CT, THE VILLAGES, F...
Community: The Villages®
MLS G5115136 • WORTH CLARK REALTY, Chris Day • WORTH CLARK REALTY
New
Esplanade at Highland Ranch
![2612 FRAZEEK CT, CLERMONT, FL, 34715, Clermont, FL 34715]()
3 beds
|3 baths
|1,827 sq ft
|House
2612 FRAZEEK CT, CLERMONT, FL, 34715
Community: Esplanade at Highland Ranch
MLS O6422732 • PREFERRED RE BROKERS III, Lana Lar... • PREFERRED RE BROKERS III
The Villages®
![1707 GOMEZ PL, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,344 sq ft
|House
1707 GOMEZ PL, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5114499 • WORTH CLARK REALTY, Chris Day • WORTH CLARK REALTY
Latitude Margaritaville
![250 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,160 sq ft
|House
250 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F...
Community: Latitude Margaritaville
MLS FC319427 • REALTY PROS ASSURED, Daniel Robins... • REALTY PROS ASSURED
The Villages®
![728 TRUMAN AVE, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|1,056 sq ft
|Manufactured Home
728 TRUMAN AVE, LADY LAKE, FL, 32159
Community: The Villages®
MLS OM727238 • JUDY L. TROUT REALTY, Jennifer Tra... • JUDY L. TROUT REALTY
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Solivita
![373 VESTRELLA DR, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS O6418728 • CHARLES RUTENBERG REALTY ORLANDO, ... • CHARLES RUTENBERG REALTY ORLANDO
Twin Lakes
![2777 SOUTHLAND ST, ST CLOUD, FL, 34772, St Cloud, FL 34772]()
MLS O6412947 • KELLER WILLIAMS CLASSIC, Barbara L... • KELLER WILLIAMS CLASSIC
The Villages®
![1214 SAN BERNARDO RD, THE VILLAGES, FL, ..., The Villages, FL 32162]()
2 beds
|2 baths
|1,146 sq ft
|Villa
1214 SAN BERNARDO RD, THE VILLAGES, FL, ...
Community: The Villages®
MLS G5113614 • WORTH CLARK REALTY, Chris Day • WORTH CLARK REALTY
The Villages®
![4946 NE 124TH RD, OXFORD, FL, 34484, Oxford, FL 34484]()
3 beds
|3 baths
|2,547 sq ft
|House
4946 NE 124TH RD, OXFORD, FL, 34484
Community: The Villages®
MLS G5111916 • KELLER WILLIAMS ELITE PARTNERS III... • KELLER WILLIAMS ELITE PARTNERS III REALTY
The Villages®
![4295 FREDDA TER, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|1,440 sq ft
|Villa
4295 FREDDA TER, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5112718 • WORTH CLARK REALTY, Chris Day • WORTH CLARK 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.
Breakaway Trails
![1 CROOKED BRIDGE WAY, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174]()
5 beds
|3 baths
|3,193 sq ft
|House
1 CROOKED BRIDGE WAY, ORMOND BEACH, FL, ...
Community: Breakaway Trails
MLS FC318428 • ADAMS, CAMERON & CO., REALTORS, Ki... • ADAMS, CAMERON & CO., REALTORS
Del Webb Sunbridge
![2743 RIVER CREEK LN, ST CLOUD, FL, 34771, St Cloud, FL 34771]()
3 beds
|3 baths
|2,321 sq ft
|House
2743 RIVER CREEK LN, ST CLOUD, FL, 34771
Community: Del Webb Sunbridge
MLS O6403534 • CHARLES RUTENBERG REALTY ORLANDO, ... • CHARLES RUTENBERG REALTY ORLANDO
The Villages®
![1806 QUEENSBURY TER, THE VILLAGES, FL, 3..., The Villages, FL 32162]()
2 beds
|2 baths
|1,188 sq ft
|Villa
1806 QUEENSBURY TER, THE VILLAGES, FL, 3...
Community: The Villages®
MLS G5111858 • WORTH CLARK REALTY, Chris Day • WORTH CLARK REALTY
The Villages®
![17654 SE 93RD BUTLER CT, THE VILLAGES, F..., The Villages, FL 32162]()
2 beds
|2 baths
|1,148 sq ft
|House
17654 SE 93RD BUTLER CT, THE VILLAGES, F...
Community: The Villages®
MLS G5111841 • WORTH CLARK REALTY, Chris Day • WORTH CLARK REALTY
Arlington Ridge
![26669 OTTER CREEK LN, LEESBURG, FL, 3474..., Leesburg, FL 34748]()
3 beds
|2 baths
|1,718 sq ft
|House
26669 OTTER CREEK LN, LEESBURG, FL, 3474...
Community: Arlington Ridge
MLS G5111769 • KELLER WILLIAMS ELITE PARTNERS III... • KELLER WILLIAMS ELITE PARTNERS III REALTY
Spruce Creek Country Club
![13732 SE 88TH CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
2 beds
|2 baths
|1,136 sq ft
|House
13732 SE 88TH CT, SUMMERFIELD, FL, 34491
Community: Spruce Creek Country Club
MLS OM723495 • JUDY L. TROUT REALTY, Jennifer Tra... • JUDY L. TROUT REALTY
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Stonecrest
![12271 SE 175TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
4 beds
|3 baths
|2,246 sq ft
|House
12271 SE 175TH LN, SUMMERFIELD, FL, 3449...
Community: Stonecrest
MLS OM722835 • JUDY L. TROUT REALTY, Jennifer Tra... • JUDY L. TROUT REALTY
Trilogy® Orlando
![615 CONSERVATION BLVD, GROVELAND, FL, 34..., Groveland, FL 34736]()
2 beds
|3 baths
|2,009 sq ft
|House
615 CONSERVATION BLVD, GROVELAND, FL, 34...
Community: Trilogy® Orlando
MLS G5111771 • KELLER WILLIAMS ELITE PARTNERS III... • KELLER WILLIAMS ELITE PARTNERS III REALTY
Spruce Creek Country Club
![9082 SE 120TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,346 sq ft
|House
9082 SE 120TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek Country Club
MLS O6403283 • MARKET CONNECT REALTY LLC, Debra V... • MARKET CONNECT REALTY LLC
The Villages®
![1666 SUMMERCHASE LOOP, THE VILLAGES, FL,..., The Villages, FL 32162]()
2 beds
|2 baths
|1,152 sq ft
|Villa
1666 SUMMERCHASE LOOP, THE VILLAGES, FL,...
Community: The Villages®
MLS G5111491 • WORTH CLARK REALTY, Chris Day • WORTH CLARK 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.
Latitude Margaritaville
![224 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,308 sq ft
|House
224 GYPSY PALACE LN, DAYTONA BEACH, FL, ...
Community: Latitude Margaritaville
MLS FC317919 • REALTY PROS ASSURED, Daniel Robins... • REALTY PROS ASSURED
Plantation Bay Golf & Country Club
![41 MAGNOLIA DR S, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
2 beds
|2 baths
|1,300 sq ft
|Condo
41 MAGNOLIA DR S, ORMOND BEACH, FL, 3217...
Community: Plantation Bay Golf & Country Club
MLS 1225591 • Adams, Cameron & Co., Realtors, Kim... • Adams, Cameron & Co., Realtors
Cresswind at Victoria Gardens
![1157 AVERY MEADOWS WAY, DELAND, FL, 3272..., Deland, FL 32724]()
2 beds
|2 baths
|1,928 sq ft
|House
1157 AVERY MEADOWS WAY, DELAND, FL, 3272...
Community: Cresswind at Victoria Gardens
MLS O6394993 • COLDWELL BANKER REALTY, Susan Herr... • COLDWELL BANKER REALTY
The Villages®
![3984 MCDOWELL DR, THE VILLAGES, FL, 3216..., The Villages, FL 32163]()
3 beds
|2 baths
|1,926 sq ft
|House
3984 MCDOWELL DR, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5110543 • WORTH CLARK REALTY, Chris Day • WORTH CLARK REALTY
Lake Ashton
![4193 STONE CREEK LOOP, LAKE WALES, FL, 3..., Lake Wales, FL 33859]()
3 beds
|2 baths
|2,058 sq ft
|House
4193 STONE CREEK LOOP, LAKE WALES, FL, 3...
Community: Lake Ashton
MLS P4938293 • CENTURY 21 WATSON & MYERS REALTY, ... • CENTURY 21 WATSON & MYERS REALTY
Latitude Margaritaville
![444 LIME AVE, DAYTONA BEACH, FL, 32124, Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,308 sq ft
|House
444 LIME AVE, DAYTONA BEACH, FL, 32124
Community: Latitude Margaritaville
MLS FC317311 • REALTY PROS ASSURED, Daniel Robins... • REALTY PROS ASSURED
Solivita
![280 INDIAN WELLS AVE, KISSIMMEE, FL, 347..., Kissimmee, FL 34759]()
2 beds
|2 baths
|2,105 sq ft
|House
280 INDIAN WELLS AVE, KISSIMMEE, FL, 347...
Community: Solivita
MLS O6394927 • CHARLES RUTENBERG REALTY ORLANDO, ... • CHARLES RUTENBERG REALTY ORLANDO
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Spruce Creek Country Club
![9512 SE 124TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
2 beds
|3 baths
|2,475 sq ft
|House
9512 SE 124TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek Country Club
MLS OM720061 • JUDY L. TROUT REALTY, Jennifer Tra... • JUDY L. TROUT REALTY
Latitude Margaritaville
![373 HANG LOOSE WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,466 sq ft
|House
373 HANG LOOSE WAY, DAYTONA BEACH, FL, 3...
Community: Latitude Margaritaville
MLS FC316817 • REALTY PROS ASSURED, Daniel Robins... • REALTY PROS ASSURED
The Villages®
![5845 STORMS AVE, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|2,627 sq ft
|House
5845 STORMS AVE, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5109376 • WORTH CLARK REALTY, Chris Day • WORTH CLARK 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®
![1462 PELICAN PATH, THE VILLAGES, FL, 321..., The Villages, FL 32162]()
3 beds
|2 baths
|1,715 sq ft
|House
1462 PELICAN PATH, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5108545 • WORTH CLARK REALTY, Chris Day • WORTH CLARK REALTY
Latitude Margaritaville
![198 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,464 sq ft
|House
198 GYPSY PALACE LN, DAYTONA BEACH, FL, ...
Community: Latitude Margaritaville
MLS FC315361 • REALTY PROS ASSURED, Daniel Robins... • REALTY PROS ASSURED
Carlsberg Estates on Lake Suzanne
![364 LAKE SUZANNE DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859]()
2 beds
|2 baths
|1,387 sq ft
|House
364 LAKE SUZANNE DR, LAKE WALES, FL, 338...
Community: Carlsberg Estates on Lake Suzanne
MLS P4936827 • CENTURY 21 WATSON & MYERS REALTY, ... • CENTURY 21 WATSON & MYERS REALTY
Lakes of Mount Dora
![8923 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757]()
3 beds
|2 baths
|1,926 sq ft
|House
8923 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...
Community: Lakes of Mount Dora
MLS G5102118 • KELLER WILLIAMS ELITE PARTNERS III... • KELLER WILLIAMS ELITE PARTNERS III REALTY
New
The Villages®
![12439 NE 48TH CIR, OXFORD, FL, 34484, Oxford, FL 34484]()
4 beds
|3 baths
|2,224 sq ft
|House
12439 NE 48TH CIR, OXFORD, FL, 34484
Community: The Villages®
MLS OM728551 • FLORIDA ADVANTAGE REALTY GROUP, Aa... • FLORIDA ADVANTAGE REALTY GROUP
New
Breakaway Trails
![73 SHADOW CREEK WAY, ORMOND BEACH, FL, 3..., Ormond Beach, FL 32174]()
5 beds
|6 baths
|4,628 sq ft
|House
73 SHADOW CREEK WAY, ORMOND BEACH, FL, 3...
Community: Breakaway Trails
MLS FC319967 • VENTURE DEVELOPMENT REALTY,INC, El... • VENTURE DEVELOPMENT REALTY,INC
New
Stonecrest
![10949 SE 169TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,366 sq ft
|House
10949 SE 169TH LN, SUMMERFIELD, FL, 3449...
Community: Stonecrest
MLS G5114964 • REALTY EXECUTIVES IN THE VILLAGES,... • REALTY EXECUTIVES IN THE VILLAGES
New
Pelican Bay Daytona Beach
![149 BLUE HERON DR D, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119]()
2 beds
|2 baths
|1,192 sq ft
|Condo
149 BLUE HERON DR D, DAYTONA BEACH, FL, ...
Community: Pelican Bay Daytona Beach
MLS V4950240 • KELLER WILLIAMS RLTY FL. PARTN, Br... • KELLER WILLIAMS RLTY FL. PARTN
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New
Pennbrooke Fairways
![909 EAGLES LNDG, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,212 sq ft
|House
909 EAGLES LNDG, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS G5115067 • CENTURY 21 ALTON CLARK, Regina Rod... • CENTURY 21 ALTON CLARK
New
Twin Lakes
![5167 GARDENROW DR, ST CLOUD, FL, 34772, St Cloud, FL 34772]()
MLS O6425082 • PULTE REALTY OF NORTH FLORIDA LLC,... • PULTE REALTY OF NORTH FLORIDA 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?
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REIN updates its listings on a daily basis. Data last updated: Jul 17, 2026.
This application does not include information on all of the properties available for sale at this time.
