Winter Park, FL 55+ rental communities & homes for rent

6 communities near Winter Park

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Overture Hamlin

$2,112.78 - $2,797.78 / mo

Base rent from $1,997

Overture Hamlin, Winter Garden, FL

New Construction | 55+ age-restricted | Built 2021 - present | 163 rental homes

Rosalia Winter Park

$1,917 - $2,770 / mo

Base rent from $1,802

Rosalia Winter Park, Winter Park, FL

New Construction | 55+ age-restricted | Built 2022 - present | 178 rental homes

RISE Viera

RISE Viera, Viera, FL

| 55+ age-restricted

The Pointe at Siena Ridge

$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

Mariblu Hunters Creek

$1,772.62 - $2,126.62 / mo

Base rent from $1,608

Mariblu Hunters Creek, Kissimmee, FL

New Construction | 55+ age-restricted | Built 2022 - 2023 | 152 rental homes

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Album Monterey Pointe

$2,015.56 - $2,225.56 / mo

Base rent from $1,900

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.

New High Vista at Ridgewood Lakes

201 PRATHER DR, DAVENPORT, FL, 33837, Davenport, FL 33837

$321,900

2 beds

2 baths

1,910 sq ft

House

201 PRATHER DR, DAVENPORT, FL, 33837

Community: High Vista at Ridgewood Lakes

New Spruce Creek Country Club

9235 SE 128TH ST, SUMMERFIELD, FL, 34491, Summerfield, FL 34491

$339,900

2 beds

2 baths

1,716 sq ft

House

9235 SE 128TH ST, SUMMERFIELD, FL, 34491

Community: Spruce Creek Country Club

New Plantation Bay Golf & Country Club

426 LONG COVE RD, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174

$569,000

3 beds

2 baths

1,931 sq ft

House

426 LONG COVE RD, ORMOND BEACH, FL, 3217...

Community: Plantation Bay Golf & Country Club

New Plantation at Leesburg

24814 PINE HL, LEESBURG, FL, 34748, Leesburg, FL 34748

$215,000

2 beds

2 baths

1,358 sq ft

Manufactured Home

24814 PINE HL, LEESBURG, FL, 34748

Community: Plantation at Leesburg

New The Villages®

1033 OAK FOREST DR, THE VILLAGES, FL, 32..., The Villages, FL 32162

$359,000

3 beds

2 baths

1,840 sq ft

House

1033 OAK FOREST DR, THE VILLAGES, FL, 32...

Community: The Villages®

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New Solivita

513 HEARTWELL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$285,000

2 beds

2 baths

1,488 sq ft

House

513 HEARTWELL DR, KISSIMMEE, FL, 34759

Community: Solivita

New The Villages®

3431 SIPSEY ST, THE VILLAGES, FL, 32162, The Villages, FL 32162

$320,000

3 beds

2 baths

1,392 sq ft

House

3431 SIPSEY ST, THE VILLAGES, FL, 32162

Community: The Villages®

New Arlington Ridge

4240 JAMES RIVER CIR, LEESBURG, FL, 3474..., Leesburg, FL 34748

$457,900

3 beds

2 baths

1,948 sq ft

House

4240 JAMES RIVER CIR, LEESBURG, FL, 3474...

Community: Arlington Ridge

New The Villages®

1426 HONEA PATH, THE VILLAGES, FL, 32162, The Villages, FL 32162

$575,000

3 beds

2 baths

2,236 sq ft

House

1426 HONEA PATH, THE VILLAGES, FL, 32162

Community: The Villages®

New Sandpiper Golf & Country Club

5832 SWALLOW DR, LAKELAND, FL, 33809, Lakeland, FL 33809

$350,000

3 beds

2 baths

1,814 sq ft

House

5832 SWALLOW DR, LAKELAND, FL, 33809

Community: Sandpiper Golf & Country Club

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 The Villages®

1461 EMMA PL, THE VILLAGES, FL, 32163, The Villages, FL 32163

$375,000

2 beds

2 baths

1,295 sq ft

House

1461 EMMA PL, THE VILLAGES, FL, 32163

Community: The Villages®

New The Villages®

1202 CHAPARRAL DR, THE VILLAGES, FL, 321..., The Villages, FL 32159

$329,000

3 beds

2 baths

1,527 sq ft

House

1202 CHAPARRAL DR, THE VILLAGES, FL, 321...

Community: The Villages®

New The Villages®

2767 DUNHAM DR, THE VILLAGES, FL, 32163, The Villages, FL 32163

$1,295,000

4 beds

3 baths

2,378 sq ft

House

2767 DUNHAM DR, THE VILLAGES, FL, 32163

Community: The Villages®

New Stonecrest

17920 SE 115TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$265,000

3 beds

2 baths

1,544 sq ft

House

17920 SE 115TH CT, SUMMERFIELD, FL, 3449...

Community: Stonecrest

New Traditions at Lake Ruby

4130 BEDFORD AVE, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884

$309,900

2 beds

2 baths

1,819 sq ft

House

4130 BEDFORD AVE, WINTER HAVEN, FL, 3388...

Community: Traditions at Lake Ruby

New The Villages®

2047 DUNSTER CT, THE VILLAGES, FL, 32162, The Villages, FL 32162

$434,999

3 beds

2 baths

1,851 sq ft

House

2047 DUNSTER CT, THE VILLAGES, FL, 32162

Community: The Villages®

Want to learn more about 55+ communities in Winter Park? 55places can help!

Questions? Call us: (888) 625-4885

New The Villages®

1577 BLYTHEWOOD LOOP, THE VILLAGES, FL, ..., The Villages, FL 32162

$398,000

3 beds

2 baths

1,513 sq ft

House

1577 BLYTHEWOOD LOOP, THE VILLAGES, FL, ...

Community: The Villages®

New Kings Ridge

3525 ROLLINGBROOK ST, CLERMONT, FL, 3471..., Clermont, FL 34711

$328,900

2 beds

2 baths

1,548 sq ft

House

3525 ROLLINGBROOK ST, CLERMONT, FL, 3471...

Community: Kings Ridge

New Plantation at Leesburg

5000 SAWGRASS LAKE CIR, LEESBURG, FL, 34..., Leesburg, FL 34748

$284,900

2 beds

2 baths

1,775 sq ft

House

5000 SAWGRASS LAKE CIR, LEESBURG, FL, 34...

Community: Plantation at Leesburg

New Royal Harbor

2880 MEDITERRANEAN LOOP, TAVARES, FL, 32..., Tavares, FL 32778

$347,500

3 beds

2 baths

2,189 sq ft

House

2880 MEDITERRANEAN LOOP, TAVARES, FL, 32...

Community: Royal Harbor

New Royal Harbor

3257 BALTIC SEA BLVD, TAVARES, FL, 32778, Tavares, FL 32778

$392,000

3 beds

3 baths

2,012 sq ft

House

3257 BALTIC SEA BLVD, TAVARES, FL, 32778

Community: Royal Harbor

New The Villages®

418 FLOSSMOOR CT, THE VILLAGES, FL, 3216..., The Villages, FL 32162

$420,000

3 beds

2 baths

1,685 sq ft

Villa

418 FLOSSMOOR CT, THE VILLAGES, FL, 3216...

Community: The Villages®

New Plantation at Leesburg

5030 EL DESTINO DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$233,000

2 beds

2 baths

1,308 sq ft

House

5030 EL DESTINO DR, LEESBURG, FL, 34748

Community: Plantation at Leesburg

New Plantation Bay Golf & Country Club

642 ELK RIVER DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174

$597,500

3 beds

2 baths

1,873 sq ft

House

642 ELK RIVER DR, ORMOND BEACH, FL, 3217...

Community: Plantation Bay Golf & Country Club

New Latitude Margaritaville

317 POP TOP LN, DAYTONA BEACH, FL, 32124, Daytona Beach, FL 32124

$358,900

2 beds

2 baths

1,160 sq ft

House

317 POP TOP LN, DAYTONA BEACH, FL, 32124

Community: Latitude Margaritaville

New Solivita

478 BALBOA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$359,000

2 beds

2 baths

2,038 sq ft

House

478 BALBOA DR, KISSIMMEE, FL, 34759

Community: Solivita

New Pelican Bay Daytona Beach

766 PELICAN BAY DR, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32119

$589,999

4 beds

4 baths

3,769 sq ft

House

766 PELICAN BAY DR, DAYTONA BEACH, FL, 3...

Community: Pelican Bay Daytona Beach

Want to learn more about 55+ communities in Winter Park? 55places can help!

Questions? Call us: (888) 625-4885

New The Villages®

1344 AUGUSTINE DR, THE VILLAGES, FL, 321..., The Villages, FL 32159

$482,000

3 beds

2 baths

1,954 sq ft

House

1344 AUGUSTINE DR, THE VILLAGES, FL, 321...

Community: The Villages®

New Plantation at Leesburg

26234 GLEN EAGLE DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$238,000

3 beds

2 baths

1,761 sq ft

House

26234 GLEN EAGLE DR, LEESBURG, FL, 34748

Community: Plantation at Leesburg

New Bridgewater at Viera

1763 GREAT BELT CIR, MELBOURNE, FL, 3294..., Melbourne, FL 32940

$475,000

2 beds

2 baths

1,903 sq ft

House

1763 GREAT BELT CIR, MELBOURNE, FL, 3294...

Community: Bridgewater at Viera

New Highland Lakes

26912 BECKER CT, LEESBURG, FL, 34748, Leesburg, FL 34748

$360,000

3 beds

2 baths

2,498 sq ft

House

26912 BECKER CT, LEESBURG, FL, 34748

Community: Highland Lakes

New The Villages®

923 MOSES LOOP, THE VILLAGES, FL, 32162, The Villages, FL 32162

$1,400,000

5 beds

4 baths

3,359 sq ft

House

923 MOSES LOOP, THE VILLAGES, FL, 32162

Community: The Villages®

New Plantation at Leesburg

4835 SABLE RIDGE CT, LEESBURG, FL, 34748, Leesburg, FL 34748

$305,000

3 beds

2 baths

1,818 sq ft

House

4835 SABLE RIDGE CT, LEESBURG, FL, 34748

Community: Plantation at Leesburg

New The Villages®

5609 HANCOCK DR, WILDWOOD, FL, 34785, Wildwood, FL 34785

$100,000

2 beds

1 baths

660 sq ft

Mobile Home

5609 HANCOCK DR, WILDWOOD, FL, 34785

Community: The Villages®

New Latitude Margaritaville

328 TIKI TER, DAYTONA BEACH, FL, 32124, Daytona Beach, FL 32124

$465,000

2 beds

2 baths

1,563 sq ft

House

328 TIKI TER, DAYTONA BEACH, FL, 32124

Community: Latitude Margaritaville

New Spruce Creek South

9532 SE 173RD LN, SUMMERFIELD, FL, 34491, Summerfield, FL 34491

$245,000

2 beds

2 baths

1,678 sq ft

House

9532 SE 173RD LN, SUMMERFIELD, FL, 34491

Community: Spruce Creek South

New The Villages®

1685 CAMPOS DR, THE VILLAGES, FL, 32162, The Villages, FL 32162

$265,000

2 beds

2 baths

1,121 sq ft

House

1685 CAMPOS DR, THE VILLAGES, FL, 32162

Community: The Villages®

New Heritage Hills

3644 SOLANA CIR F, CLERMONT, FL, 34711, Clermont, FL 34711

$275,000

2 beds

2 baths

1,503 sq ft

Villa

3644 SOLANA CIR F, CLERMONT, FL, 34711

Community: Heritage Hills

Want to learn more about 55+ communities in Winter Park? 55places can help!

Questions? Call us: (888) 625-4885

New Pennbrooke Fairways

412 WESTWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$189,900

2 beds

2 baths

1,140 sq ft

House

412 WESTWOOD DR, LEESBURG, FL, 34748

Community: Pennbrooke Fairways

New Harbor Hills Country Club

5066 GREENS DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$649,000

4 beds

3 baths

2,544 sq ft

House

5066 GREENS DR, LADY LAKE, FL, 32159

Community: Harbor Hills Country Club

Frequently Asked Questions

What size 55+ communities are there in Winter Park?

In Winter Park, there is 1 small community with less than 500 homes.

How many homes are there in the smallest, largest, and average 55+ communities in Winter Park?

The smallest 55+ community in Winter Park has 178 homes, the largest has 178 homes, and the average community consists of 178 homes.

Are there new 55+ homes available in Winter Park?

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.

Are there gated 55+ communities in 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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Want to learn more about 55+ communities in Winter Park?

Call us: (888) 625-4885

6 communities

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Winter Park, FL 55+ rental communities & homes for rent

6 communities near Winter Park

2,414 homes near Winter Park

2 beds

2 baths

1,910 sq ft

House

2 beds

2 baths

1,716 sq ft

House

3 beds

2 baths

1,931 sq ft

House

2 beds

2 baths

1,358 sq ft

Manufactured Home

3 beds

2 baths

1,840 sq ft

House

2 beds

2 baths

1,488 sq ft

House

3 beds

2 baths

1,392 sq ft

House

3 beds

2 baths

1,948 sq ft

House

3 beds

2 baths

2,236 sq ft

House

3 beds

2 baths

1,814 sq ft

House

2 beds

2 baths

1,295 sq ft

House

3 beds

2 baths

1,527 sq ft

House

4 beds

3 baths

2,378 sq ft

House

3 beds

2 baths

1,544 sq ft

House

2 beds

2 baths

1,819 sq ft

House

3 beds

2 baths

1,851 sq ft

House

3 beds

2 baths

1,513 sq ft

House

2 beds

2 baths

1,548 sq ft

House

2 beds

2 baths

1,775 sq ft

House

3 beds