Winter Park, FL 55+ active adult communities & homes for sale - Page 16

2,698 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

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

Venetian Bay

$300ks - $1Ms

Venetian Bay, New Smyrna Beach, FL

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

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

Questions? Call us: (888) 625-4885

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

5 rating (3 reviews)

Stonecrest

$200ks - $500ks

Stonecrest, Summerfield, FL

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

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.

5 rating (8 reviews)

Royal Highlands

$200ks - $400ks

Royal Highlands, Leesburg, FL

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

5 rating (3 reviews)

Lake Ashton

$200ks - $500ks

Lake Ashton, Lake Wales, FL

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

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 (8 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

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

Halifax Plantation

$300ks - $1Ms

Halifax Plantation, Ormond Beach, FL

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

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

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

The Country Club of Mount...

$200ks - $1Ms

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

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

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

Scottish Highlands

$100ks - $200ks

Scottish Highlands, Leesburg, FL

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

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

Four Seasons at Orlando

$300ks - $600ks

Four Seasons at Orlando, Kissimmee, FL

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

Heritage - The Cottages o...

$300ks

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

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

Breakaway Trails

$400ks - $800ks

Breakaway Trails, Ormond Beach, FL

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

4.8 rating (6 reviews)

Highland Lakes

$100ks - $200ks

Highland Lakes, Leesburg, FL

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

Gatherings of Lake Nona

$300ks - $400ks

Gatherings of Lake Nona, Orlando, FL

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

Del Webb at Viera

$400ks - $1Ms

Del Webb at Viera, Melbourne, FL

New Construction | 55+ age-restricted | Built 2021 - present | 1,300 homes

Highland Fairways

$100ks - $300ks

Highland Fairways, Lakeland, FL

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

Lakeside Landings

$100ks - $300ks

Lakeside Landings, Oxford, FL

New and Resale | Age-targeted | Built 2005 - present | 700 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

1 rating (1 reviews)

Sullivan Ranch

$200ks - $500ks

Sullivan Ranch, Mount Dora, FL

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

3553 CONNOR WAY, THE VILLAGES, FL, 32163

Community: The Villages®

2 baths

1,939 sq ft

House

2595 CARIBE DR, THE VILLAGES, FL, 32162

Community: The Villages®

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

Questions? Call us: (888) 625-4885

The Villages®

$325,000

3 beds

2 baths

1,496 sq ft

House

17728 SE 81ST WYNSTONE AVE, THE VILLAGES...

Community: The Villages®

The Villages®

$649,900

3 beds

3 baths

2,119 sq ft

House

4529 SAMANTHA CT, THE VILLAGES, FL, 3216...

Community: The Villages®

Plantation at Leesburg

4003 PLANTATION BLVD, LEESBURG, FL, 3474..., Leesburg, FL 34748

$299,900

2 beds

2 baths

1,865 sq ft

House

4003 PLANTATION BLVD, LEESBURG, FL, 3474...

Community: Plantation at Leesburg

Cresswind at Victoria Gardens

226 STONINGTON WAY, DELAND, FL, 32724, Deland, FL 32724

$315,000

2 beds

2 baths

1,480 sq ft

House

226 STONINGTON WAY, DELAND, FL, 32724

Community: Cresswind at Victoria Gardens

Venetian Bay

521 VENETIAN VILLA DR, NEW SMYRNA BEACH,..., New Smyrna Beach, FL 32168

$569,900

4 beds

3 baths

2,353 sq ft

House

521 VENETIAN VILLA DR, NEW SMYRNA BEACH,...

Community: Venetian Bay

Solivita

2358 PALM TREE DR, POINCIANA, FL, 34759, Poinciana, FL 34759

$290,000

2 beds

2 baths

1,539 sq ft

Villa

2358 PALM TREE DR, POINCIANA, FL, 34759

Community: Solivita

Cindy Certified

1495 MORNING WALK DR, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174

$387,990

4 beds

2 baths

1,828 sq ft

House

1495 MORNING WALK DR, ORMOND BEACH, FL, ...

Huntington at Hunter's Ridge

8 HAWK ROOST CT, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$350,000

2 beds

2 baths

1,602 sq ft

House

8 HAWK ROOST CT, ORMOND BEACH, FL, 32174

Community: Huntington at Hunter's Ridge

Cindy Certified

6736 SPOTTED EAGLE LOOP, HOWEY IN THE HI..., Howey In The Hills, FL 34737

$375,999

4 beds

2 baths

2,008 sq ft

House

6736 SPOTTED EAGLE LOOP, HOWEY IN THE HI...

Plantation at Leesburg

24242 BELLE MEDE DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$349,000

3 beds

2 baths

1,728 sq ft

House

24242 BELLE MEDE DR, LEESBURG, FL, 34748

Community: Plantation at Leesburg

Four Seasons at Orlando

1646 KEY BAY TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747

$345,000

2 beds

2 baths

1,557 sq ft

Villa

1646 KEY BAY TRL, KISSIMMEE, FL, 34747

Community: Four Seasons at Orlando

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

Questions? Call us: (888) 625-4885

The Villages®

$450,000

3 beds

3 beds

2 baths

1,945 sq ft

House

3193 KRANZ AVE, THE VILLAGES, FL, 32163

Community: The Villages®

Cindy Certified

9 PINE BUSH LN, PALM COAST, FL, 32164, Palm Coast, FL 32164

$332,500

3 beds

2 baths

1,600 sq ft

House

9 PINE BUSH LN, PALM COAST, FL, 32164

Pelican Bay Daytona Beach

156 BOB WHITE CT 1560, DAYTONA BEACH, FL..., Daytona Beach, FL 32119

$182,000

2 beds

2 baths

1,189 sq ft

Condo

156 BOB WHITE CT 1560, DAYTONA BEACH, FL...

Community: Pelican Bay Daytona Beach

911 BROOKRIDGE LN, ORMOND BEACH, FL, 321...

Community: Plantation Bay Golf & Country Club

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

Questions? Call us: (888) 625-4885

Plantation Bay Golf & Country Club

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

$399,000

3 beds

2 baths

1,872 sq ft

House

684 ALDENHAM LN, ORMOND BEACH, FL, 32174

Community: Plantation Bay Golf & Country Club

Venetian Bay

266 PORTOFINO BLVD, NEW SMYRNA BEACH, FL..., New Smyrna Beach, FL 32168

$1,100,000

4 beds

3 baths

2,788 sq ft

House

266 PORTOFINO BLVD, NEW SMYRNA BEACH, FL...

Community: Venetian Bay

1…10 11 12 13 14 15 16 17 18 19 20 21 22…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

2,698 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: Oct 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 16

98 communities near Winter Park

2,698 homes near Winter Park

2 beds

2 baths

2,296 sq ft

House

4 beds

3 baths

2,562 sq ft

House

3 beds

4 baths

2,580 sq ft

House

3 beds

2 baths

1,580 sq ft

House

3 beds

2 baths

1,809 sq ft

House

4 beds

2 baths

1,928 sq ft

House

3 beds

2 baths

1,690 sq ft

House

3 beds

3 baths

2,151 sq ft

House

5 beds

2 baths

1,708 sq ft

House

3 beds

3 baths

2,335 sq ft

House

2 beds

2 baths

1,871 sq ft

House

3 beds

2 baths

2,413 sq ft

House

3 beds

2 baths

1,822 sq ft

House

3 beds

2 baths

1,726 sq ft

House

3 beds

2 baths

1,788 sq ft

House

3 beds

2 baths

1,939 sq ft

House

3 beds

2 baths

1,496 sq ft

House

3 beds

3 baths

2,119 sq ft

House

2 beds

2 baths

1,865 sq ft

House

2 beds