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

7 communities near Winter Park

Sort by:

Relevance

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

$1,716.62 - $2,062.62 / mo

Base rent from $1,552

Mariblu Hunters Creek, Kissimmee, FL

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

Album Monterey Pointe

$1,928.56 - $2,227.56 / mo

Base rent from $1,813

Album Monterey Pointe, Kissimmee, FL

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

Rosalia Winter Park

$2,097 - $2,572 / 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 - $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

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

Questions? Call us: (888) 625-4885

RISE Viera

$2,056.50 - $3,604.50 / mo

Base rent from $1,940

RISE Viera, Viera, FL

| 55+ age-restricted

Azalea Lake Mary

$1,920.78 - $3,485.78 / mo

Base rent from $1,800

Azalea Lake Mary, Lake Mary, FL

| 55+ age-restricted | 178 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 The Villages®

1068 BURNETTOWN PL, THE VILLAGES, FL, 32..., The Villages, FL 32162

$629,900

3 beds

2 baths

1,837 sq ft

Villa

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

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®

The Villages®

$775,000

3 beds

2 baths

1,943 sq ft

House

2643 JUPITER WAY, THE VILLAGES, FL, 3216...

Community: The Villages®

Baytree

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

$250,000

3 beds

2 baths

1,209 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®

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

Questions? Call us: (888) 625-4885

The Villages®

$279,900

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

The Villages®

$359,900

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

$405,000

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

$765,000

5 beds

3 baths

3,193 sq ft

House

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

Community: Breakaway Trails

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®

$269,900

2 beds

2 baths

1,188 sq ft

Villa

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

Community: The Villages®

Arlington Ridge

26669 OTTER CREEK LN, LEESBURG, FL, 3474..., Leesburg, FL 34748

$350,000

3 beds

2 baths

1,718 sq ft

House

26669 OTTER CREEK LN, LEESBURG, FL, 3474...

Community: Arlington Ridge

Stonecrest

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

$396,000

4 beds

3 baths

2,246 sq ft

House

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

Community: Stonecrest

Trilogy® Orlando

615 CONSERVATION BLVD, GROVELAND, FL, 34..., Groveland, FL 34736

$349,900

2 beds

3 baths

2,009 sq ft

House

615 CONSERVATION BLVD, GROVELAND, FL, 34...

Community: Trilogy® Orlando

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

$459,900

2 beds

2 baths

1,928 sq ft

House

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

Community: Cresswind at Victoria Gardens

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

Questions? Call us: (888) 625-4885

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

The Villages®

$1,042,000

3 beds

2 baths

2,627 sq ft

House

5845 STORMS AVE, THE VILLAGES, FL, 32163

Community: The Villages®

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 Del Webb Orlando

672 CORDOBA DR, DAVENPORT, FL, 33837, Davenport, FL 33837

$369,900

2 beds

2 baths

1,956 sq ft

House

672 CORDOBA DR, DAVENPORT, FL, 33837

Community: Del Webb Orlando

New Plantation Bay Golf & Country Club

1283 ROYAL POINTE LN, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174

$499,999

4 beds

2 baths

2,029 sq ft

House

1283 ROYAL POINTE LN, ORMOND BEACH, FL, ...

Community: Plantation Bay Golf & Country Club

New Harbor Hills Country Club

39407 TREELINE DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$589,000

4 beds

4 baths

2,502 sq ft

House

39407 TREELINE DR, LADY LAKE, FL, 32159

Community: Harbor Hills Country Club

New Royal Highlands

5925 BAG PIPE PL, LEESBURG, FL, 34748, Leesburg, FL 34748

$335,000

3 beds

2 baths

2,251 sq ft

House

5925 BAG PIPE PL, LEESBURG, FL, 34748

Community: Royal Highlands

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

Questions? Call us: (888) 625-4885

New Spruce Creek South

10337 SE 176TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$240,000

3 beds

2 baths

1,526 sq ft

House

10337 SE 176TH ST, SUMMERFIELD, FL, 3449...

Community: Spruce Creek South

New Plantation at Leesburg

5047 EL DESTINO DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$195,000

2 beds

2 baths

1,296 sq ft

Manufactured Home

5047 EL DESTINO DR, LEESBURG, FL, 34748

Community: Plantation at Leesburg

New

Cindy Certified

1065 CHELAN FALLS DR, DELAND, FL, 32724, Deland, FL 32724

$340,000

4 beds

2 baths

1,943 sq ft

House

1065 CHELAN FALLS DR, DELAND, FL, 32724

New Harbor Hills Country Club

39905 BAYVIEW DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$279,900

2 beds

2 baths

1,598 sq ft

Villa

39905 BAYVIEW DR, LADY LAKE, FL, 32159

Community: Harbor Hills Country Club

New The Villages®

622 LISBON LN, THE VILLAGES, FL, 32159, The Villages, FL 32159

$259,900

2 beds

2 baths

1,092 sq ft

House

622 LISBON LN, THE VILLAGES, FL, 32159

Community: The Villages®

New The Villages®

1451 LUCKETT CT, THE VILLAGES, FL, 32163, The Villages, FL 32163

$600,000

3 beds

2 baths

2,035 sq ft

House

1451 LUCKETT CT, THE VILLAGES, FL, 32163

Community: The Villages®

New Stonecrest

17105 SE 111TH TERRACE RD, SUMMERFIELD, ..., Summerfield, FL 34491

$599,000

3 beds

3 baths

2,154 sq ft

House

17105 SE 111TH TERRACE RD, SUMMERFIELD, ...

Community: Stonecrest

New Latitude Margaritaville

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

$394,900

2 beds

2 baths

1,466 sq ft

House

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

Community: Latitude Margaritaville

New Grand Haven

54 SHINNECOCK DR, PALM COAST, FL, 32137, Palm Coast, FL 32137

$479,000

3 beds

2 baths

1,506 sq ft

House

54 SHINNECOCK DR, PALM COAST, FL, 32137

Community: Grand Haven

New The Country Club of Mount Dora

8034 ARCADIAN CT, MOUNT DORA, FL, 32757, Mount Dora, FL 32757

$365,000

2 beds

2 baths

1,603 sq ft

House

8034 ARCADIAN CT, MOUNT DORA, FL, 32757

Community: The Country Club of Mount Dora

New Stonecrest

17399 SE 116TH COURT RD, SUMMERFIELD, FL..., Summerfield, FL 34491

$319,000

3 beds

2 baths

1,751 sq ft

House

17399 SE 116TH COURT RD, SUMMERFIELD, FL...

Community: Stonecrest

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

Questions? Call us: (888) 625-4885

New Gatherings of Lake Nona

7545 LAUREATE BLVD 7404, ORLANDO, FL, 32..., Orlando, FL 32827

$424,990

2 beds

2 baths

1,486 sq ft

Condo

7545 LAUREATE BLVD 7404, ORLANDO, FL, 32...

Community: Gatherings of Lake Nona

New Gatherings of Lake Nona

7545 LAUREATE BLVD 7408, ORLANDO, FL, 32..., Orlando, FL 32827

$399,990

2 beds

2 baths

1,368 sq ft

Condo

7545 LAUREATE BLVD 7408, ORLANDO, FL, 32...

Community: Gatherings of Lake Nona

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?

Global - Lead Form - Buyer or Renter

First Name

Last Name

Phone/Mobile

Text

I'm looking to:

Rent

Buy

*55places does not provide or maintain community HOA information.

Yes, I want to subscribe to email updates from 55places.com, including newsletters, community announcements, and more.

I agree to receive SMS messages to connect me with a local expert.

By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting optout@55places.com. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

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

Call us: (888) 625-4885

7 communities

Remove Boundaries ×

Map Satellite

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

7 communities near Winter Park

2,715 homes near Winter Park

3 beds

2 baths

1,837 sq ft

Villa

2 beds

2 baths

1,434 sq ft

Villa

3 beds

2 baths

1,943 sq ft

House

3 beds

2 baths

1,209 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

2 baths

1,188 sq ft

Villa

3 beds

2 baths

1,718 sq ft

House

4 beds

3 baths

2,246 sq ft

House

2 beds

3 baths

2,009 sq ft

House

2 beds

2 baths

1,308 sq ft

House

2 beds

2 baths

1,928 sq ft

House

3 beds

2 baths

2,058 sq ft

House

2 beds

2 baths

1,308 sq ft

House

2 beds

3 baths

2,475 sq ft

House

2 beds