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Winter Park, FL 55+ rental communities & homes for rent
7 communities near Winter Park
2,259 homes near Winter Park
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$2,112.78
- $2,931.78 / mo
Base rent from $1,997
Overture Hamlin, Winter Garden, FL
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
163 rental homes
$2,097
- $2,612 / mo
Base rent from $1,902
Rosalia Winter Park, Winter Park, FL
New Construction
|
55+ age-restricted
|
Built 2022 - present
|
178 rental homes
$1,623.65
- $2,263.88 / mo
Base rent from $1,499
The Pointe at Siena Ridge, Davenport, FL
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
163 rental homes
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$1,668.62
- $2,022.62 / mo
Base rent from $1,504
Mariblu Hunters Creek, Kissimmee, FL
New Construction
|
55+ age-restricted
|
Built 2022 - 2023
|
152 rental homes
$1,928.56
- $2,225.56 / mo
Base rent from $1,813
Album Monterey Pointe, Kissimmee, FL
New Construction
|
55+ age-restricted
|
150 rental homes
Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
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
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...
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...
Solivita
![373 VESTRELLA DR, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS O6418728 • CHARLES RUTENBERG REALTY ORLANDO, ...
Twin Lakes
![2777 SOUTHLAND ST, ST CLOUD, FL, 34772, St Cloud, FL 34772]()
MLS O6412947 • KELLER WILLIAMS CLASSIC, Barbara L...
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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
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...
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
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 1226392 • Adams, Cameron & Co., Realtors, Kim...
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, ...
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®
![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
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
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...
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...
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...
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...
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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...
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
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...
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...
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.
Plantation at Leesburg
![4936 SAWGRASS LAKE CIR, LEESBURG, FL, 34..., Leesburg, FL 34748]()
3 beds
|2 baths
|1,784 sq ft
|House
4936 SAWGRASS LAKE CIR, LEESBURG, FL, 34...
Community: Plantation at Leesburg
MLS G5111335 • KELLER WILLIAMS ELITE PARTNERS III...
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...
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
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, ...
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...
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, ...
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...
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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...
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
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
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
![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...
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, ...
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...
New
Sullivan Ranch
![30119 TOKARA TER, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
3 beds
|2 baths
|1,670 sq ft
|House
30119 TOKARA TER, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
MLS G5114877 • KELLIE & CO REAL ESTATE, Kellie Wh...
New
Halifax Plantation
![3412 REXFORD CIR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,250 sq ft
|House
3412 REXFORD CIR, ORMOND BEACH, FL, 3217...
Community: Halifax Plantation
MLS FC319739 • REALTY PROS ASSURED, Mike Metzger
New
The Country Club of Mount Dora
![8059 LAUREL RIDGE DR, MOUNT DORA, FL, 32..., Mount Dora, FL 32757]()
3 beds
|3 baths
|2,777 sq ft
|House
8059 LAUREL RIDGE DR, MOUNT DORA, FL, 32...
Community: The Country Club of Mount Dora
MLS G5114769 • LAKE LIFE REALTY, Brandy Lake
New
Sullivan Ranch
![21315 SORRAIA CV, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
4 beds
|2 baths
|2,164 sq ft
|House
21315 SORRAIA CV, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
MLS G5114847 • HOMESTEAD REAL ESTATE LLC, Linda B...
New
The Savannahs
![4044 CALADIUM CIR, MELBOURNE, FL, 32904, Melbourne, FL 32904]()
4 beds
|2 baths
|2,046 sq ft
|House
4044 CALADIUM CIR, MELBOURNE, FL, 32904
Community: The Savannahs
MLS 1082165 • Florida Homes Rlty. & Mtg. LLC, Sha...
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New
Latitude Margaritaville
![316 TIKI TER, DAYTONA BEACH, FL, 32124, Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,563 sq ft
|Villa
316 TIKI TER, DAYTONA BEACH, FL, 32124
Community: Latitude Margaritaville
MLS O6421974 • KELLER WILLIAMS WINTER PARK, Dawn ...
New
Sandpiper Golf & Country Club
![6213 RAVEN RUN, LAKELAND, FL, 33809, Lakeland, FL 33809]()
2 beds
|2 baths
|1,112 sq ft
|House
6213 RAVEN RUN, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS L4963385 • COLDWELL BANKER REALTY, Kimberly I...
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?
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REIN updates its listings on a daily basis. Data last updated: Jul 10, 2026.
This application does not include information on all of the properties available for sale at this time.
