Winter Park, FL 55+ active adult communities & homes for sale - Page 21

2,702 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

Venetian Bay

$300ks - $1Ms

Venetian Bay, New Smyrna Beach, FL

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

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

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

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

Questions? Call us: (888) 625-4885

4.7 rating (18 reviews)

Solivita

$300ks - $700ks

Solivita, Kissimmee, FL

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

Stonecrest

$200ks - $500ks

Stonecrest, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 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

Pelican Bay Daytona Beach

$100ks - $600ks

Pelican Bay Daytona Beach, Daytona Beach, FL

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

Grand Haven

$200ks - $800ks

Grand Haven, Palm Coast, FL

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

5 rating (7 reviews)

Kings Ridge

$200ks - $400ks

Kings Ridge, Clermont, FL

Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 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 (8 reviews)

Royal Highlands

$200ks - $400ks

Royal Highlands, Leesburg, FL

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

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

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

Questions? Call us: (888) 625-4885

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

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

Halifax Plantation

$300ks - $1Ms

Halifax Plantation, Ormond Beach, FL

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

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

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 (1 reviews)

Cresswind at Victoria Gar...

$300ks - $500ks

Cresswind at Victoria Gar..., DeLand, FL

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

The Country Club of Mount...

$200ks - $1Ms

The Country Club of Mount..., Mount Dora, FL

Resale Only | Age-targeted | Built 1991 - 2005 | 827 homes

Highland Fairways

$100ks - $300ks

Highland Fairways, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1983 - 1998 | 660 homes

Breakaway Trails

$400ks - $800ks

Breakaway Trails, Ormond Beach, FL

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

5 rating (1 reviews)

Royal Harbor

$200ks - $800ks

Royal Harbor, Tavares, FL

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

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

Questions? Call us: (888) 625-4885

5 rating (8 reviews)

Pennbrooke Fairways

<$100k - $300ks

Pennbrooke Fairways, Leesburg, FL

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

Heritage - The Cottages o...

$300ks

Heritage - The Cottages o..., Okahumpka, FL

New Construction | 55+ age-restricted | Built 2022 - present | 179 homes

Gatherings of Lake Nona

$300ks - $400ks

Gatherings of Lake Nona, Orlando, FL

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

4.8 rating (6 reviews)

Highland Lakes

$100ks - $200ks

Highland Lakes, Leesburg, FL

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

1 rating (1 reviews)

Sullivan Ranch

$200ks - $500ks

Sullivan Ranch, Mount Dora, FL

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

Foxwood Lake Estates

$100ks - $200ks

Foxwood Lake Estates, Lakeland, FL

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

5 rating (1 reviews)

Legacy of Leesburg

$200ks - $400ks

Legacy of Leesburg, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1999 - 2017 | 1,000 homes

5 rating (1 reviews)

VillageWalk at Lake Nona

$300ks - $700ks

VillageWalk at Lake Nona, Orlando, FL

Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 homes

The Timbers at Everlands

$200ks - $500ks

The Timbers at Everlands, Palm Bay, FL

New Construction | 55+ age-restricted | Built 2023 - present | 450 homes

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

Questions? Call us: (888) 625-4885

The Lakes at Harmony

$200ks - $400ks

The Lakes at Harmony, Harmony, FL

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

Colonnades

$100ks - $200ks

Colonnades, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1985 - 1994 | 360 homes

3625 SUBLETT LOOP, TAVARES, FL, 32778

Summit Greens

794 WOLF CREEK ST, CLERMONT, FL, 34711, Clermont, FL 34711

$360,000

3 beds

2 baths

1,747 sq ft

House

794 WOLF CREEK ST, CLERMONT, FL, 34711

Community: Summit Greens

House

273 SILVER MAPLE RD, GROVELAND, FL, 3473...

Community: Trilogy® Orlando

Plantation at Leesburg

25524 LAUREL VALLEY RD, LEESBURG, FL, 34..., Leesburg, FL 34748

$399,000

3 beds

3 baths

2,650 sq ft

House

25524 LAUREL VALLEY RD, LEESBURG, FL, 34...

Community: Plantation at Leesburg

Cindy Certified

3128 REPOSE DR, CLERMONT, FL, 34714, Clermont, FL 34714

$245,990

2 baths

1,158 sq ft

House

1631 EDISTO LN, THE VILLAGES, FL, 32162

Community: The Villages®

Pelican Bay Daytona Beach

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

$549,900

4 beds

4 baths

2,648 sq ft

House

785 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

The Villages®

$299,000

2 beds

2 baths

1,156 sq ft

Villa

2673 SUFFOLK ST, THE VILLAGES, FL, 32162

Community: The Villages®

Twin Lakes

5023 SUNFALLS AVE, ST CLOUD, FL, 34769, St Cloud, FL 34769

$450,000

3 beds

2 baths

1,863 sq ft

House

5023 SUNFALLS AVE, ST CLOUD, FL, 34769

Community: Twin Lakes

Twin Lakes

$509,530

3 beds

2 baths

2,084 sq ft

House

5095 TWIN LAKES BLVD, ST CLOUD, FL, 3477...

Community: Twin Lakes

Gatherings of Lake Nona

7521 LAUREATE BLVD 5208, ORLANDO, FL, 32..., Orlando, FL 32827

$419,000

2 beds

2 baths

1,445 sq ft

Condo

7521 LAUREATE BLVD 5208, ORLANDO, FL, 32...

Community: Gatherings of Lake Nona

Tohoqua Reserve

1994 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744

$435,000

3 beds

2 baths

2,056 sq ft

House

1994 SPRING SHOWER CIR, KISSIMMEE, FL, 3...

Community: Tohoqua Reserve

Lake Ashton

4188 ABERDEEN LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859

$325,000

2 beds

2 baths

1,154 sq ft

House

4188 ABERDEEN LN, LAKE WALES, FL, 33859

Community: Lake Ashton

Cindy Certified

1714 UPLAND LN, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884

$435,000

4 beds

3 baths

2,565 sq ft

House

1714 UPLAND LN, WINTER HAVEN, FL, 33884

Fountain View

$407,990

4 beds

3 baths

2,020 sq ft

House

1340 FOUNTAIN VIEW ST, ORMOND BEACH, FL,...

Community: Fountain View

489 LUNA BELLA LN, NEW SMYRNA BEACH, FL,...

House

2733 SOUTHLAND ST, 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

The Villages®

$350,000

3 beds

2 baths

1,670 sq ft

House

1602 MALACARA LN, THE VILLAGES, FL, 3216...

Community: The Villages®

Cindy Certified

5828 PUZO PL, MOUNT DORA, FL, 32757, Mount Dora, FL 32757

$439,900

3 beds

3 baths

2,558 sq ft

House

5828 PUZO PL, MOUNT DORA, FL, 32757

1…15 16 17 18 19 20 21 22 23 24 25 26 27…68

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

2,702 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: Aug 25, 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 21

98 communities near Winter Park

2,702 homes near Winter Park

3 beds

2 baths

1,503 sq ft

House

3 beds

2 baths

2,111 sq ft

House

3 beds

2 baths

1,738 sq ft

House

4 beds

3 baths

2,053 sq ft

House

3 beds

2 baths

1,747 sq ft

House

3 beds

2 baths

1,245 sq ft

House

4 beds

2 baths

1,609 sq ft

House

4 beds

2 baths

1,609 sq ft

House

4 beds

2 baths

1,530 sq ft

House

2 beds

3 baths

2,140 sq ft

House

3 beds

3 baths

2,650 sq ft

House

2 beds

2 baths

1,421 sq ft

Villa

2 beds

3 baths

2,303 sq ft

House

2 beds

2 baths

1,148 sq ft

House

2 beds

2 baths

1,158 sq ft

House

4 beds

4 baths

2,648 sq ft

House

2 beds

2 baths

1,156 sq ft

Villa

3 beds

2 baths

1,863 sq ft

House

3 beds

2 baths

2,084 sq ft

House

2 beds