Winter Park, FL 55+ active adult communities & homes for sale - Page 18

2,513 homes near Winter Park

Sort by:

Relevance

4 rating (17 reviews)

The Villages®

$100ks - $1Ms

The Villages®, The Villages, FL

New and Resale | 55+ age-restricted | Built 1978 - present | 70,000 homes

4.7 rating (18 reviews)

Solivita

$300ks - $700ks

Solivita, Kissimmee, FL

New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 homes

4.5 rating (11 reviews)

Spruce Creek Country Club

$100ks - $400ks

Spruce Creek Country Club, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1996 - 2007 | 3,250 homes

Venetian Bay

$300ks - $1Ms

Venetian Bay, New Smyrna Beach, FL

New and Resale | Age-targeted | Built 2004 - present | 1,561 homes

5 rating (2 reviews)

Plantation at Leesburg

$100ks - $300ks

Plantation at Leesburg, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 homes

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

Questions? Call us: (888) 625-4885

3.6 rating (48 reviews)

Latitude Margaritaville

$300ks - $800ks

Latitude Margaritaville, Daytona Beach, FL

Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes

5 rating (3 reviews)

Stonecrest

$200ks - $500ks

Stonecrest, Summerfield, FL

New and Resale | 55+ age-restricted | Built 1990 - present | 2,200 homes

5 rating (1 reviews)

Plantation Bay Golf &...

$400ks - $2Ms

Plantation Bay Golf &..., Ormond Beach, FL

New and Resale | Age-targeted | Built 1988 - present | 3,500 homes

5 rating (3 reviews)

Lake Ashton

$200ks - $500ks

Lake Ashton, Lake Wales, FL

Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes

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.

3.8 rating (4 reviews)

Spruce Creek South

$100ks - $200ks

Spruce Creek South, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes

5 rating (8 reviews)

Royal Highlands

$200ks - $400ks

Royal Highlands, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes

5 rating (1 reviews)

Del Webb Sunbridge

$400ks - $800ks

Del Webb Sunbridge, St. Cloud, FL

New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 homes

5 rating (7 reviews)

Kings Ridge

$200ks - $400ks

Kings Ridge, Clermont, FL

Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 homes

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

Questions? Call us: (888) 625-4885

Grand Haven

$200ks - $800ks

Grand Haven, Palm Coast, FL

New and Resale | Age-targeted | Built 1997 - present | 1,901 homes

3.8 rating (6 reviews)

Trilogy® Orlando

$200ks - $500ks

Trilogy® Orlando, Groveland, FL

Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 homes

5 rating (3 reviews)

Twin Lakes

$200ks - $600ks

Twin Lakes, St. Cloud, FL

New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes

Halifax Plantation

$300ks - $1Ms

Halifax Plantation, Ormond Beach, FL

New and Resale | Age-targeted | Built 1980 - present | 1,000 homes

5 rating (1 reviews)

Sandpiper Golf & Coun...

$100ks - $300ks

Sandpiper Golf & Coun..., Lakeland, FL

New and Resale | 55+ age-restricted | Built 1985 - present | 1,193 homes

2.8 rating (6 reviews)

Arlington Ridge

$200ks - $500ks

Arlington Ridge, Leesburg, FL

New and Resale | 55+ age-restricted | Built 2005 - present | 629 homes

Pelican Bay Daytona Beach

$100ks - $600ks

Pelican Bay Daytona Beach, Daytona Beach, FL

Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 homes

4 rating (4 reviews)

Lakes of Mount Dora

$300ks - $900ks

Lakes of Mount Dora, Mount Dora, FL

New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes

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

Questions? Call us: (888) 625-4885

4 rating (2 reviews)

Harbor Hills Country Club

$300ks - $900ks

Harbor Hills Country Club, Lady Lake, FL

New and Resale | Age-targeted | Built 1989 - present | 940 homes

1 rating (1 reviews)

Sullivan Ranch

$200ks - $500ks

Sullivan Ranch, Mount Dora, FL

Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 homes

3.6 rating (5 reviews)

Heritage Hills

$200ks - $400ks

Heritage Hills, Clermont, FL

New and Resale | 55+ age-restricted | Built 2006 - present | 1,154 homes

5 rating (2 reviews)

Heritage Isle

$300ks - $500ks

Heritage Isle, Viera, FL

Resale Only | 55+ age-restricted | Built 2005 - 2017 | 1,500 homes

4.8 rating (6 reviews)

Highland Lakes

$100ks - $200ks

Highland Lakes, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes

5 rating (1 reviews)

Royal Harbor

$200ks - $800ks

Royal Harbor, Tavares, FL

Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes

5 rating (8 reviews)

Pennbrooke Fairways

<$100k - $300ks

Pennbrooke Fairways, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes

Four Seasons at Orlando

$300ks - $600ks

Four Seasons at Orlando, Kissimmee, FL

New Construction | 55+ age-restricted | Built 2017 - present | 557 homes

5 rating (1 reviews)

Cresswind at Victoria Gar...

$200ks - $600ks

Cresswind at Victoria Gar..., DeLand, FL

Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 homes

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

Questions? Call us: (888) 625-4885

Scottish Highlands

$100ks - $200ks

Scottish Highlands, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1983 - 1992 | 653 homes

3.8 rating (5 reviews)

Traditions at Lake Ruby

$200ks - $300ks

Traditions at Lake Ruby, Winter Haven, FL

Resale Only | 55+ age-restricted | Built 2005 - 2020 | 552 homes

4.4 rating (16 reviews)

Del Webb Orlando

$200ks - $500ks

Del Webb Orlando, Davenport, FL

Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes

4.1 rating (9 reviews)

Indian River Colony Club

$200ks - $400ks

Indian River Colony Club, Melbourne, FL

New and Resale | 55+ age-restricted | Built 1986 - present | 777 homes

Tohoqua Reserve

$300ks - $600ks

Tohoqua Reserve, Kissimmee, FL

New Construction | 55+ age-restricted | Built 2021 - present | 258 homes

The Lakes at Harmony

$200ks - $400ks

The Lakes at Harmony, Harmony, FL

New and Resale | 55+ age-restricted | Built 2016 - present | 400 homes

Summer Trees

$200ks - $400ks

Summer Trees, Port Orange, FL

Resale Only | 55+ age-restricted | Built 1976 - 2005 | 500 homes

Breakaway Trails

$400ks - $800ks

Breakaway Trails, Ormond Beach, FL

New and Resale | Age-targeted | Built 1985 - present | 976 homes

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

Questions? Call us: (888) 625-4885

Foxwood Lake Estates

$100ks - $200ks

Foxwood Lake Estates, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1982 - 1987 | 545 homes

Gatherings of Lake Nona

$300ks - $400ks

Gatherings of Lake Nona, Orlando, FL

New and Resale | 55+ age-restricted | Built 2017 - present | 216 homes

1232 DUSTIN DR, LADY LAKE, FL, 32159

Community: The Villages®

Latitude Margaritaville

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

$379,900

2 beds

2 baths

1,308 sq ft

House

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

Community: Latitude Margaritaville

The Villages®

$343,800

2 beds

2 baths

1,562 sq ft

House

1204 BARCELONA DR, THE VILLAGES, FL, 321...

Community: The Villages®

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

Questions? Call us: (888) 625-4885

Highland Lakes

5506 ROSEWALL CIR, LEESBURG, FL, 34748, Leesburg, FL 34748

$199,900

2 beds

2 baths

1,120 sq ft

Villa

5506 ROSEWALL CIR, LEESBURG, FL, 34748

Community: Highland Lakes

The Villages®

$619,000

3 beds

2 baths

1,939 sq ft

House

3130 VANDENBERG CT, THE VILLAGES, FL, 32...

Community: The Villages®

The Villages®

$489,900

3 beds

2 baths

1,492 sq ft

Villa

4193 SILVANA WAY, THE VILLAGES, FL, 3216...

Community: The Villages®

Twin Lakes

$423,000

2 beds

2 baths

1,624 sq ft

House

5092 TWIN LAKES BLVD, ST CLOUD, FL, 3477...

Community: Twin Lakes

High Vista at Ridgewood Lakes

832 CUNNINGHAM DR, DAVENPORT, FL, 33837, Davenport, FL 33837

$345,000

2 beds

2 baths

1,803 sq ft

House

832 CUNNINGHAM DR, DAVENPORT, FL, 33837

Community: High Vista at Ridgewood Lakes

Del Webb Sunbridge

6354 SHIMMERING SHORES LN, ST CLOUD, FL,..., St Cloud, FL 34771

$475,000

2 beds

2 baths

1,670 sq ft

House

6354 SHIMMERING SHORES LN, ST CLOUD, FL,...

Community: Del Webb Sunbridge

Plantation at Leesburg

3810 ST EMMA CT, LEESBURG, FL, 34748, Leesburg, FL 34748

$355,000

3 beds

4 baths

2,473 sq ft

House

3810 ST EMMA CT, LEESBURG, FL, 34748

Community: Plantation at Leesburg

Royal Harbor

5135 INDIAN OCEAN LOOP, TAVARES, FL, 327..., Tavares, FL 32778

$334,999

3 beds

2 baths

1,766 sq ft

House

5135 INDIAN OCEAN LOOP, TAVARES, FL, 327...

Community: Royal Harbor

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

Questions? Call us: (888) 625-4885

Del Webb Sunbridge

2732 CHERRY BLOSSOM LOOP, ST CLOUD, FL, ..., St Cloud, FL 34771

$407,000

2 beds

2 baths

1,584 sq ft

Villa

2732 CHERRY BLOSSOM LOOP, ST CLOUD, FL, ...

Community: Del Webb Sunbridge

The Villages®

$349,900

2 beds

2 baths

1,200 sq ft

Villa

1550 LIME GROVE LN, THE VILLAGES, FL, 32...

Community: The Villages®

The Villages®

$449,900

3 beds

2 baths

1,654 sq ft

Villa

1947 TRANQUILITY LN, THE VILLAGES, FL, 3...

Community: The Villages®

The Villages®

$439,000

3 beds

2 baths

1,531 sq ft

House

5458 BACON TER, THE VILLAGES, FL, 32163

Community: The Villages®

Spruce Creek Country Club

9845 SE 138TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491

$279,000

2 beds

2 baths

1,638 sq ft

House

9845 SE 138TH LOOP, SUMMERFIELD, FL, 344...

Community: Spruce Creek Country Club

Spruce Creek South

10681 SE 178TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$170,000

2 beds

2 baths

1,296 sq ft

House

10681 SE 178TH ST, SUMMERFIELD, FL, 3449...

Community: Spruce Creek South

The Villages®

$309,000

3 beds

2 baths

1,527 sq ft

House

9211 SE 179TH OSAGE PL, THE VILLAGES, FL...

Community: The Villages®

Stonecrest

12420 SE 176TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491

$415,000

3 beds

3 baths

2,055 sq ft

House

12420 SE 176TH LOOP, SUMMERFIELD, FL, 34...

Community: Stonecrest

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

Questions? Call us: (888) 625-4885

The Villages®

$525,000

3 beds

2 baths

2,084 sq ft

House

2576 JUPITER WAY, THE VILLAGES, FL, 3216...

Community: The Villages®

The Villages®

$398,500

3 beds

2 baths

1,544 sq ft

Villa

1946 LOADSTAR AVE, THE VILLAGES, FL, 321...

Community: The Villages®

The Villages®

$349,900

3 beds

2 baths

1,855 sq ft

House

16865 SE 93RD CUTHBERT CIR, THE VILLAGES...

Community: The Villages®

Halifax Plantation

3225 LIENSTER CIR, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174

$299,900

3 beds

2 baths

1,474 sq ft

House

3225 LIENSTER CIR, ORMOND BEACH, FL, 321...

Community: Halifax Plantation

Solivita

93 OAK LEAF DR, POINCIANA, FL, 34759, Poinciana, FL 34759

$349,900

3 beds

2 baths

2,141 sq ft

House

93 OAK LEAF DR, POINCIANA, FL, 34759

Community: Solivita

Lakeside Landings

10351 ADDISON SHORE WAY, OXFORD, FL, 344..., Oxford, FL 34484

$394,900

4 beds

3 baths

2,003 sq ft

House

10351 ADDISON SHORE WAY, OXFORD, FL, 344...

Community: Lakeside Landings

Palms at Serenoa

17615 BLAZING STAR CIR, CLERMONT, FL, 34..., Clermont, FL 34714

$420,000

3 beds

2 baths

1,822 sq ft

House

17615 BLAZING STAR CIR, CLERMONT, FL, 34...

Community: Palms at Serenoa

Breakaway Trails

2 CREEK BEND WAY, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174

$769,000

4 beds

4 baths

3,098 sq ft

House

2 CREEK BEND WAY, ORMOND BEACH, FL, 3217...

Community: Breakaway Trails

Carlsberg Estates on Lake Suzanne

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

$259,000

2 beds

2 baths

1,406 sq ft

House

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

House

1301 OAK FOREST DR, THE VILLAGES, FL, 32...

Community: The Villages®

Pelican Bay Daytona Beach

168 BERMUDA PETREL CT, DAYTONA BEACH, FL..., Daytona Beach, FL 32119

$242,000

2 beds

2 baths

1,260 sq ft

House

168 BERMUDA PETREL CT, DAYTONA BEACH, FL...

Community: Pelican Bay Daytona Beach

The Villages®

$299,900

2 beds

2 baths

1,156 sq ft

Villa

1769 APALACHEE AVE, THE VILLAGES, FL, 32...

Community: The Villages®

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

Questions? Call us: (888) 625-4885

The Villages®

1404 PLANTATION DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$158,900

2 beds

2 baths

1,040 sq ft

Manufactured Home

1404 PLANTATION DR, LADY LAKE, FL, 32159

Community: The Villages®

Compass Pointe

689 DANVILLE CIR, MELBOURNE, FL, 32904, Melbourne, FL 32904

$309,000

3 beds

2 baths

1,948 sq ft

House

689 DANVILLE CIR, MELBOURNE, FL, 32904

Community: Compass Pointe

1…12 13 14 15 16 17 18 19 20 21 22 23 24…63

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

2,513 homes

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+ active adult communities & homes for sale - Page 18

90 communities near Winter Park

2,513 homes near Winter Park

3 beds

2 baths

2,031 sq ft

House

2 beds

2 baths

1,093 sq ft

Condo

2 beds

2 baths

936 sq ft

Manufactured Home

2 beds

2 baths

1,308 sq ft

House

2 beds

2 baths

1,562 sq ft

House

2 beds

2 baths

1,120 sq ft

Villa

3 beds

2 baths

1,939 sq ft

House

3 beds

2 baths

1,492 sq ft

Villa

2 beds

2 baths

1,624 sq ft

House

2 beds

2 baths

1,803 sq ft

House

2 beds

2 baths

1,670 sq ft

House

3 beds

4 baths

2,473 sq ft

House

3 beds

2 baths

1,766 sq ft

House

2 beds

2 baths

1,584 sq ft

Villa

2 beds

2 baths

1,200 sq ft

Villa

3 beds

2 baths

1,654 sq ft

Villa

3 beds

2 baths

1,531 sq ft

House

2 beds

2 baths

1,638 sq ft

House

2 beds

2 baths

1,296 sq ft

House

3 beds