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

6 communities near Winter Park

Sort by:

Relevance

Rosalia Winter Park

$1,892 - $2,770 / mo

Base rent from $1,777

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

Album Monterey Pointe

$1,949 - $2,213 / mo

Base rent from $1,833

Album Monterey Pointe, Kissimmee, FL

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

The Pointe at Siena Ridge

$1,779.65 - $2,263.88 / mo

Base rent from $1,655

The Pointe at Siena Ridge, Davenport, FL

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

Mariblu Hunters Creek

$1,835 - $2,119 / mo

Base rent from $1,670

Mariblu Hunters Creek, Kissimmee, FL

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

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

Questions? Call us: (888) 625-4885

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

Questions? Call us: (888) 625-4885

Overture Hamlin

$2,112.78 - $2,935.78 / mo

Base rent from $1,997

Overture Hamlin, Winter Garden, FL

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

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®

9232 SE 168TH COOK PL, THE VILLAGES, FL,..., The Villages, FL 32162

$365,000

3 beds

2 baths

1,733 sq ft

Villa

9232 SE 168TH COOK PL, THE VILLAGES, FL,...

Community: The Villages®

New The Villages®

9469 SE 176TH SAFFOLD ST, THE VILLAGES, ..., The Villages, FL 32162

$349,000

3 beds

2 baths

1,505 sq ft

House

9469 SE 176TH SAFFOLD ST, THE VILLAGES, ...

Community: The Villages®

New Palms at Serenoa

3645 BLUE SAGE LOOP, CLERMONT, FL, 34714, Clermont, FL 34714

$475,000

4 beds

2 baths

2,069 sq ft

House

3645 BLUE SAGE LOOP, CLERMONT, FL, 34714

Community: Palms at Serenoa

New The Villages®

8015 SE 174TH BELHAVEN LOOP, THE VILLAGE..., The Villages, FL 32162

$275,000

2 beds

2 baths

1,148 sq ft

House

8015 SE 174TH BELHAVEN LOOP, THE VILLAGE...

Community: The Villages®

New Four Seasons at Orlando

7624 SAND PIERRE CT, KISSIMMEE, FL, 3474..., Kissimmee, FL 34747

$349,500

2 beds

2 baths

1,437 sq ft

House

7624 SAND PIERRE CT, KISSIMMEE, FL, 3474...

Community: Four Seasons at Orlando

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

Questions? Call us: (888) 625-4885

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

Questions? Call us: (888) 625-4885

New Spruce Creek South

17590 SE 96TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$189,000

2 beds

2 baths

1,008 sq ft

House

17590 SE 96TH AVE, SUMMERFIELD, FL, 3449...

Community: Spruce Creek South

New Solivita

3461 FALLBROOK DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$300,000

2 beds

2 baths

1,499 sq ft

Villa

3461 FALLBROOK DR, KISSIMMEE, FL, 34759

Community: Solivita

New Scottish Highlands

27 GORDON CT, LEESBURG, FL, 34788, Leesburg, FL 34788

$215,000

2 beds

2 baths

1,252 sq ft

House

27 GORDON CT, LEESBURG, FL, 34788

Community: Scottish Highlands

New Plantation at Leesburg

3447 MOUNT HOPE LOOP, LEESBURG, FL, 3474..., Leesburg, FL 34748

$299,999

3 beds

2 baths

1,868 sq ft

House

3447 MOUNT HOPE LOOP, LEESBURG, FL, 3474...

Community: Plantation at Leesburg

New Gatherings of Lake Nona

7517 LAUREATE BLVD 4403, ORLANDO, FL, 32..., Orlando, FL 32827

$329,000

2 beds

2 baths

1,549 sq ft

Condo

7517 LAUREATE BLVD 4403, ORLANDO, FL, 32...

Community: Gatherings of Lake Nona

New Grand Haven

20 N VILLAGE PKWY, PALM COAST, FL, 32137, Palm Coast, FL 32137

$750,000

3 beds

3 baths

2,875 sq ft

House

20 N VILLAGE PKWY, PALM COAST, FL, 32137

Community: Grand Haven

New The Villages®

2088 VISION CT, THE VILLAGES, FL, 32163, The Villages, FL 32163

$689,000

3 beds

2 baths

2,013 sq ft

House

2088 VISION CT, THE VILLAGES, FL, 32163

Community: The Villages®

New Foxwood Lake Estates

1704 QUAIL HILL DR, LAKELAND, FL, 33810, Lakeland, FL 33810

$140,000

2 beds

2 baths

1,372 sq ft

Manufactured Home

1704 QUAIL HILL DR, LAKELAND, FL, 33810

Community: Foxwood Lake Estates

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

Questions? Call us: (888) 625-4885

New The Country Club of Mount Dora

1901 PARK FOREST BLVD, MOUNT DORA, FL, 3..., Mount Dora, FL 32757

$539,000

3 beds

2 baths

2,286 sq ft

House

1901 PARK FOREST BLVD, MOUNT DORA, FL, 3...

Community: The Country Club of Mount Dora

New Sullivan Ranch

20926 SULLIVAN RANCH BLVD, MOUNT DORA, F..., Mount Dora, FL 32757

$349,900

3 beds

2 baths

1,440 sq ft

House

20926 SULLIVAN RANCH BLVD, MOUNT DORA, F...

Community: Sullivan Ranch

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

Questions? Call us: (888) 625-4885

New Foxwood Lake Estates

4966 DEERWOOD DR, LAKELAND, FL, 33810, Lakeland, FL 33810

$174,900

2 beds

2 baths

1,352 sq ft

Manufactured Home

4966 DEERWOOD DR, LAKELAND, FL, 33810

Community: Foxwood Lake Estates

New Twin Lakes

4902 W FOUNTAINWOOD DR, ST CLOUD, FL, 34..., St Cloud, FL 34772

$420,000

2 beds

2 baths

1,624 sq ft

House

4902 W FOUNTAINWOOD DR, ST CLOUD, FL, 34...

Community: Twin Lakes

New The Villages®

1738 AUGUSTINE DR, THE VILLAGES, FL, 321..., The Villages, FL 32159

$775,000

4 beds

3 baths

2,959 sq ft

House

1738 AUGUSTINE DR, THE VILLAGES, FL, 321...

Community: The Villages®

New Foxwood Lake Estates

1798 FOX HILL DR, LAKELAND, FL, 33810, Lakeland, FL 33810

$164,900

3 beds

2 baths

1,176 sq ft

Manufactured Home

1798 FOX HILL DR, LAKELAND, FL, 33810

Community: Foxwood Lake Estates

New Four Seasons at Orlando

1999 KEY BAY TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747

$429,980

2 beds

2 baths

1,557 sq ft

Villa

1999 KEY BAY TRL, KISSIMMEE, FL, 34747

Community: Four Seasons at Orlando

New Lakes at Laurel Highlands

2933 IVY LAKE CT, LAKELAND, FL, 33811, Lakeland, FL 33811

$389,500

5 beds

3 baths

2,674 sq ft

House

2933 IVY LAKE CT, LAKELAND, FL, 33811

Community: Lakes at Laurel Highlands

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

Questions? Call us: (888) 625-4885

New The Villages®

5511 HEAD WAY, THE VILLAGES, FL, 32163, The Villages, FL 32163

$394,900

3 beds

2 baths

1,708 sq ft

House

5511 HEAD WAY, THE VILLAGES, FL, 32163

Community: The Villages®

New High Vista at Ridgewood Lakes

116 FLEMING LN, DAVENPORT, FL, 33837, Davenport, FL 33837

$309,000

2 beds

2 baths

1,776 sq ft

House

116 FLEMING LN, DAVENPORT, FL, 33837

Community: High Vista at Ridgewood Lakes

New The Villages®

603 ROBIN LANE AVE, WILDWOOD, FL, 34785, Wildwood, FL 34785

$159,900

2 beds

2 baths

1,352 sq ft

Manufactured Home

603 ROBIN LANE AVE, WILDWOOD, FL, 34785

Community: The Villages®

New The Villages®

1714 EL NINO ST, THE VILLAGES, FL, 32162, The Villages, FL 32162

$289,000

2 beds

2 baths

1,121 sq ft

Villa

1714 EL NINO ST, THE VILLAGES, FL, 32162

Community: The Villages®

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

Questions? Call us: (888) 625-4885

New The Villages®

2530 FOXBRIDGE TER, THE VILLAGES, FL, 32..., The Villages, FL 32162

$324,900

3 beds

2 baths

1,392 sq ft

House

2530 FOXBRIDGE TER, THE VILLAGES, FL, 32...

Community: The Villages®

New Plantation Bay Golf & Country Club

608 ALDENHAM LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$575,000

3 beds

2 baths

2,090 sq ft

House

608 ALDENHAM LN, ORMOND BEACH, FL, 32174

Community: Plantation Bay Golf & Country Club

New Plantation at Leesburg

25845 GLEN EAGLE DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$325,000

3 beds

2 baths

2,047 sq ft

House

25845 GLEN EAGLE DR, LEESBURG, FL, 34748

Community: Plantation at Leesburg

New The Villages®

3284 THEODORE TER, THE VILLAGES, FL, 321..., The Villages, FL 32163

$674,900

3 beds

3 baths

2,033 sq ft

House

3284 THEODORE TER, THE VILLAGES, FL, 321...

Community: The Villages®

New The Villages®

717 TANGERINE DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$220,000

2 beds

2 baths

1,332 sq ft

Manufactured Home

717 TANGERINE DR, LADY LAKE, FL, 32159

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®

2254 ISLEWORTH CIR, THE VILLAGES, FL, 32..., The Villages, FL 32163

$1,250,000

3 beds

2 baths

3,082 sq ft

House

2254 ISLEWORTH CIR, THE VILLAGES, FL, 32...

Community: The Villages®

New Harbor Hills Country Club

5204 GREENS DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$479,900

3 beds

3 baths

2,248 sq ft

House

5204 GREENS DR, LADY LAKE, FL, 32159

Community: Harbor Hills Country Club

New The Country Club of Mount Dora

9035 SAINT ANDREWS WAY, MOUNT DORA, FL, ..., Mount Dora, FL 32757

$364,900

3 beds

2 baths

1,578 sq ft

House

9035 SAINT ANDREWS WAY, MOUNT DORA, FL, ...

Community: The Country Club of Mount Dora

New The Villages®

935 WREN ST, THE VILLAGES, FL, 32163, The Villages, FL 32163

$365,000

3 beds

2 baths

1,357 sq ft

Villa

935 WREN ST, THE VILLAGES, FL, 32163

Community: The Villages®

New Venetian Bay

424 LUNA BELLA LN 416C, NEW SMYRNA BEACH..., New Smyrna Beach, FL 32168

$257,145

2 beds

2 baths

1,669 sq ft

Condo

424 LUNA BELLA LN 416C, NEW SMYRNA BEACH...

Community: Venetian Bay

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

Questions? Call us: (888) 625-4885

New Heritage - The Cottages of Sanders Grove

5715 HIAWASSEE RD, OKAHUMPKA, FL, 34762, Okahumpka, FL 34762

$363,389

4 beds

3 baths

1,938 sq ft

House

5715 HIAWASSEE RD, OKAHUMPKA, FL, 34762

Community: Heritage - The Cottages of Sanders Grove

New Solivita

1405 HARBOR RIDGE DR, KISSIMMEE, FL, 347..., Kissimmee, FL 34759

$279,000

2 beds

2 baths

1,543 sq ft

House

1405 HARBOR RIDGE DR, KISSIMMEE, FL, 347...

Community: Solivita

New Heritage - The Cottages of Sanders Grove

5727 HIAWASSEE RD, OKAHUMPKA, FL, 34762, Okahumpka, FL 34762

$323,286

3 beds

2 baths

1,407 sq ft

House

5727 HIAWASSEE RD, OKAHUMPKA, FL, 34762

Community: Heritage - The Cottages of Sanders Grove

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

Questions? Call us: (888) 625-4885

New Solivita

106 VISTA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$229,900

3 beds

2 baths

1,786 sq ft

House

106 VISTA DR, KISSIMMEE, FL, 34759

Community: Solivita

New Lake Ashton

5268 PEBBLE BEACH BLVD, WINTER HAVEN, FL..., Winter Haven, FL 33884

$579,900

3 beds

2 baths

2,354 sq ft

House

5268 PEBBLE BEACH BLVD, WINTER HAVEN, FL...

Community: Lake Ashton

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 [email protected]. 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

6 communities

Remove Boundaries ×

Map Satellite

The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: Apr 10, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us

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

6 communities near Winter Park

2,513 homes near Winter Park

3 beds

2 baths

1,733 sq ft

Villa

3 beds

2 baths

1,505 sq ft

House

4 beds

2 baths

2,069 sq ft

House

2 beds

2 baths

1,148 sq ft

House

2 beds

2 baths

1,437 sq ft

House

2 beds

2 baths

1,008 sq ft

House

2 beds

2 baths

1,499 sq ft

Villa

2 beds

2 baths

1,252 sq ft

House

3 beds

2 baths

1,868 sq ft

House

2 beds

2 baths

1,549 sq ft

Condo

3 beds

3 baths

2,875 sq ft

House

3 beds

2 baths

2,013 sq ft

House

2 beds

2 baths

1,372 sq ft

Manufactured Home

3 beds

2 baths

2,286 sq ft

House

3 beds

2 baths

1,440 sq ft

House

2 beds

2 baths

1,352 sq ft

Manufactured Home

2 beds

2 baths

1,624 sq ft

House

4 beds

3 baths

2,959 sq ft

House

3 beds

2 baths

1,176 sq ft

Manufactured Home

2 beds