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

8 communities near Winter Park

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The Pointe at Siena Ridge

$1,764.65 - $2,213.88 / mo

Base rent from $1,640

The Pointe at Siena Ridge, Davenport, FL

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

Mariblu Hunters Creek

$1,818.62 - $2,224.62 / mo

Base rent from $1,654

Mariblu Hunters Creek, Kissimmee, FL

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

Album Monterey Pointe

$1,880.56 - $2,327.56 / mo

Base rent from $1,765

Album Monterey Pointe, Kissimmee, FL

New Construction | 55+ age-restricted | 150 rental homes

Rosalia Winter Park

$2,097 - $2,562 / mo

Base rent from $1,902

Rosalia Winter Park, Winter Park, FL

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

Overture Hamlin

$2,112.78 - $3,215.78 / mo

Base rent from $1,997

Overture Hamlin, Winter Garden, FL

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

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RISE Viera

$2,014.50 - $3,916.50 / mo

Base rent from $1,898

RISE Viera, Viera, FL

| 55+ age-restricted | 166 rental homes

5 rating (1 reviews)

Azalea Lake Mary

$1,960.78 - $3,775.78 / mo

Base rent from $1,820

Azalea Lake Mary, Lake Mary, FL

| 55+ age-restricted | 178 rental homes

Mera at East Shore

$1,700s - $3,700s / mo

Mera at East Shore, Apopka, FL

New Construction | 55+ age-restricted | Built 2026 - 2027 | 196 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®

$949,900

3 beds

2 baths

2,680 sq ft

House

1126 MIONA SHORES DR, THE VILLAGES, FL, ...

Community: The Villages®

Spruce Creek South

10701 SE 179TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$279,900

3 beds

2 baths

1,668 sq ft

House

10701 SE 179TH LN, SUMMERFIELD, FL, 3449...

Community: Spruce Creek South

Latitude Margaritaville

294 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124

$358,888

2 beds

2 baths

1,308 sq ft

House

294 GYPSY PALACE LN, DAYTONA BEACH, FL, ...

Community: Latitude Margaritaville

The Villages®

$349,900

2 beds

2 baths

1,258 sq ft

Villa

1075 BURNETTOWN PL, THE VILLAGES, FL, 32...

Community: The Villages®

The Villages®

$429,900

3 beds

2 baths

1,612 sq ft

Villa

2289 SWANSEA TER, THE VILLAGES, FL, 3216...

Community: The Villages®

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Trilogy® Orlando

306 ALCOVE DR, GROVELAND, FL, 34736, Groveland, FL 34736

$350,000

3 beds

2 baths

1,925 sq ft

House

306 ALCOVE DR, GROVELAND, FL, 34736

Community: Trilogy® Orlando

The Villages®

$329,900

3 beds

2 baths

1,553 sq ft

House

1507 BARRERA CT, THE VILLAGES, FL, 32159

Community: The Villages®

The Villages®

$319,900

2 beds

2 baths

1,094 sq ft

Villa

1339 LAJOLLA CIR, THE VILLAGES, FL, 3215...

Community: The Villages®

Solivita

513 BARCELONA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$295,000

2 beds

2 baths

1,574 sq ft

House

513 BARCELONA DR, KISSIMMEE, FL, 34759

Community: Solivita

The Villages®

$598,700

3 beds

2 baths

1,837 sq ft

Villa

1068 BURNETTOWN PL, THE VILLAGES, FL, 32...

Community: 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.

The Villages®

$260,000

2 beds

2 baths

1,121 sq ft

Villa

1606 CAMPOS DR, THE VILLAGES, FL, 32162

Community: The Villages®

The Villages®

$319,900

2 beds

2 baths

1,434 sq ft

Villa

1930 RHETT RD, THE VILLAGES, FL, 32163

Community: The Villages®

Baytree

615 JUNIPER WAY, TAVARES, FL, 32778, Tavares, FL 32778

$285,000

3 beds

2 baths

1,440 sq ft

House

615 JUNIPER WAY, TAVARES, FL, 32778

Community: Baytree

The Villages®

$299,900

3 beds

2 baths

1,392 sq ft

House

17648 SE 93RD BUTLER CT, THE VILLAGES, F...

Community: The Villages®

The Villages®

$269,900

2 beds

2 baths

1,344 sq ft

House

1707 GOMEZ PL, THE VILLAGES, FL, 32162

Community: The Villages®

Twin Lakes

2777 SOUTHLAND ST, ST CLOUD, FL, 34772, St Cloud, FL 34772

$550,000

3 beds

3 baths

2,365 sq ft

House

2777 SOUTHLAND ST, ST CLOUD, FL, 34772

Community: Twin Lakes

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Questions? Call us: (888) 625-4885

The Villages®

$349,900

2 beds

2 baths

1,146 sq ft

Villa

1214 SAN BERNARDO RD, THE VILLAGES, FL, ...

Community: The Villages®

The Villages®

4946 NE 124TH RD, OXFORD, FL, 34484, Oxford, FL 34484

$380,000

3 beds

3 baths

2,547 sq ft

House

4946 NE 124TH RD, OXFORD, FL, 34484

Community: The Villages®

Breakaway Trails

1 CROOKED BRIDGE WAY, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174

$725,000

5 beds

3 baths

3,193 sq ft

House

1 CROOKED BRIDGE WAY, ORMOND BEACH, FL, ...

Community: Breakaway Trails

The Villages®

$269,900

2 beds

2 baths

1,188 sq ft

Villa

1806 QUEENSBURY TER, THE VILLAGES, FL, 3...

Community: The Villages®

Stonecrest

12271 SE 175TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$389,000

4 beds

3 baths

2,246 sq ft

House

12271 SE 175TH LN, SUMMERFIELD, FL, 3449...

Community: Stonecrest

Latitude Margaritaville

224 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124

$357,900

2 beds

2 baths

1,308 sq ft

House

224 GYPSY PALACE LN, DAYTONA BEACH, FL, ...

Community: Latitude Margaritaville

Cresswind at Victoria Gardens

1157 AVERY MEADOWS WAY, DELAND, FL, 3272..., Deland, FL 32724

$449,700

2 beds

2 baths

1,928 sq ft

House

1157 AVERY MEADOWS WAY, DELAND, FL, 3272...

Community: Cresswind at Victoria Gardens

Lake Ashton

4193 STONE CREEK LOOP, LAKE WALES, FL, 3..., Lake Wales, FL 33859

$535,000

3 beds

2 baths

2,058 sq ft

House

4193 STONE CREEK LOOP, LAKE WALES, FL, 3...

Community: Lake Ashton

Latitude Margaritaville

444 LIME AVE, DAYTONA BEACH, FL, 32124, Daytona Beach, FL 32124

$359,900

2 beds

2 baths

1,308 sq ft

House

444 LIME AVE, DAYTONA BEACH, FL, 32124

Community: Latitude Margaritaville

Spruce Creek Country Club

9512 SE 124TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491

$399,900

2 beds

3 baths

2,475 sq ft

House

9512 SE 124TH LOOP, SUMMERFIELD, FL, 344...

Community: Spruce Creek Country Club

Latitude Margaritaville

373 HANG LOOSE WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124

$399,900

2 beds

2 baths

1,466 sq ft

House

373 HANG LOOSE WAY, DAYTONA BEACH, FL, 3...

Community: Latitude Margaritaville

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

Questions? Call us: (888) 625-4885

Latitude Margaritaville

198 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124

$386,495

2 beds

2 baths

1,464 sq ft

House

198 GYPSY PALACE LN, DAYTONA BEACH, FL, ...

Community: Latitude Margaritaville

Carlsberg Estates on Lake Suzanne

364 LAKE SUZANNE DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859

$284,900

2 beds

2 baths

1,387 sq ft

House

364 LAKE SUZANNE DR, LAKE WALES, FL, 338...

Community: Carlsberg Estates on Lake Suzanne

New Halifax Plantation

3250 BAILEY ANN DR, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174

$335,000

2 beds

2 baths

1,687 sq ft

House

3250 BAILEY ANN DR, ORMOND BEACH, FL, 32...

Community: Halifax Plantation

New The Villages®

1863 DALTON DR, THE VILLAGES, FL, 32162, The Villages, FL 32162

$300,000

2 beds

2 baths

1,152 sq ft

Villa

1863 DALTON DR, THE VILLAGES, FL, 32162

Community: The Villages®

New Venetian Bay

2942 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168

$315,000

3 beds

3 baths

1,754 sq ft

House

2942 MELETO BLVD, NEW SMYRNA BEACH, FL, ...

Community: Venetian Bay

New Lake Ashton

4029 SABLE LOOP DR, LAKE WALES, FL, 3385..., Lake Wales, FL 33859

$599,000

3 beds

2 baths

2,330 sq ft

House

4029 SABLE LOOP DR, LAKE WALES, FL, 3385...

Community: Lake Ashton

New Halifax Plantation

1303 BANGOR DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$350,000

2 beds

2 baths

1,687 sq ft

Townhouse

1303 BANGOR DR, ORMOND BEACH, FL, 32174

Community: Halifax Plantation

New The Villages®

1700 JADESTONE TER, THE VILLAGES, FL, 32..., The Villages, FL 32162

$359,000

2 beds

2 baths

1,138 sq ft

Villa

1700 JADESTONE TER, THE VILLAGES, FL, 32...

Community: The Villages®

New The Villages®

798 MILLHORN LOOP, THE VILLAGES, FL, 321..., The Villages, FL 32163

$359,000

3 beds

2 baths

1,500 sq ft

House

798 MILLHORN LOOP, THE VILLAGES, FL, 321...

Community: The Villages®

New Royal Palm

1671 ARECA PALM DR, PORT ORANGE, FL, 321..., Port Orange, FL 32128

$355,000

2 beds

2 baths

1,451 sq ft

Townhouse

1671 ARECA PALM DR, PORT ORANGE, FL, 321...

Community: Royal Palm

New Twin Lakes

4918 DRAWDY CT, ST CLOUD, FL, 34772, St Cloud, FL 34772

$439,000

3 beds

3 baths

2,365 sq ft

House

4918 DRAWDY CT, ST CLOUD, FL, 34772

Community: Twin Lakes

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

Questions? Call us: (888) 625-4885

New Plantation at Leesburg

24907 CRANES ROOST CIR, LEESBURG, FL, 34..., Leesburg, FL 34748

$375,000

3 beds

2 baths

1,848 sq ft

House

24907 CRANES ROOST CIR, LEESBURG, FL, 34...

Community: Plantation at Leesburg

New Plantation Bay Golf & Country Club

1025 HAMPSTEAD LN, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174

$1,375,000

4 beds

4 baths

4,342 sq ft

House

1025 HAMPSTEAD LN, ORMOND BEACH, FL, 321...

Community: Plantation Bay Golf & 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?

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8 communities

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

8 communities near Winter Park

2,703 homes near Winter Park

3 beds

2 baths

2,680 sq ft

House

3 beds

2 baths

1,668 sq ft

House

2 beds

2 baths

1,308 sq ft

House

2 beds

2 baths

1,258 sq ft

Villa

3 beds

2 baths

1,612 sq ft

Villa

3 beds

2 baths

1,925 sq ft

House

3 beds

2 baths

1,553 sq ft

House

2 beds

2 baths

1,094 sq ft

Villa

2 beds

2 baths

1,574 sq ft

House

3 beds

2 baths

1,837 sq ft

Villa

2 beds

2 baths

1,121 sq ft

Villa

2 beds

2 baths

1,434 sq ft

Villa

3 beds

2 baths

1,440 sq ft

House

3 beds

2 baths

1,392 sq ft

House

2 beds

2 baths

1,344 sq ft

House

3 beds

3 baths

2,365 sq ft

House

2 beds

2 baths

1,146 sq ft

Villa

3 beds

3 baths

2,547 sq ft

House

5 beds

3 baths

3,193 sq ft

House

2 beds