Winter Park, FL 55+ active adult communities & homes for sale - Page 30

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

Halifax Plantation

$300ks - $1Ms

Halifax Plantation, Ormond Beach, FL

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

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

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

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

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

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

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

4.8 rating (6 reviews)

Highland Lakes

$100ks - $200ks

Highland Lakes, Leesburg, FL

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

Breakaway Trails

$400ks - $800ks

Breakaway Trails, Ormond Beach, FL

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

Highland Fairways

$100ks - $300ks

Highland Fairways, Lakeland, FL

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

Del Webb at Viera

$400ks - $1Ms

Del Webb at Viera, Melbourne, FL

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

2697 FERMOY DR, ORMOND BEACH, FL, 32174

Heritage Hills

3650 LIMESTONE ST, CLERMONT, FL, 34711, Clermont, FL 34711

$384,000

3 beds

2 baths

1,677 sq ft

House

3650 LIMESTONE ST, CLERMONT, FL, 34711

Community: Heritage Hills

Venetian Bay

538 VENETIAN PALMS BLVD, NEW SMYRNA BEAC..., New Smyrna Beach, FL 32168

$319,000

3 beds

3 baths

1,779 sq ft

House

538 VENETIAN PALMS BLVD, NEW SMYRNA BEAC...

Community: Venetian Bay

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

Questions? Call us: (888) 625-4885

Cindy Certified

117 LAKESIDE CT, BUNNELL, FL, 32110, Bunnell, FL 32110

$339,000

4 beds

2 baths

1,858 sq ft

House

117 LAKESIDE CT, BUNNELL, FL, 32110

The Villages®

$399,900

2 beds

3 baths

2,138 sq ft

Villa

1519 MARTINEZ DR, THE VILLAGES, FL, 3215...

Community: The Villages®

Gatherings of Lake Nona

7517 LAUREATE BLVD 4303, ORLANDO, FL, 32..., Orlando, FL 32827

$309,900

2 beds

2 baths

1,549 sq ft

Condo

7517 LAUREATE BLVD 4303, ORLANDO, FL, 32...

Community: Gatherings of Lake Nona

Twin Lakes

5013 VANTAGE CT, ST CLOUD, FL, 34772, St Cloud, FL 34772

$549,900

3 beds

3 baths

3,114 sq ft

House

5013 VANTAGE CT, ST CLOUD, FL, 34772

Community: Twin Lakes

Highland Fairways

2033 LONG BOAT DR, LAKELAND, FL, 33810, Lakeland, FL 33810

$205,000

2 beds

2 baths

1,205 sq ft

House

2033 LONG BOAT DR, LAKELAND, FL, 33810

Community: Highland Fairways

Kings Ridge

4224 SNOWDON ST, CLERMONT, FL, 34711, Clermont, FL 34711

$292,000

2 beds

2 baths

1,170 sq ft

House

4224 SNOWDON ST, CLERMONT, FL, 34711

Community: Kings Ridge

Preserve at Lakeside Landings

5852 MARSH LANDING DR, WINTER HAVEN, FL,..., Winter Haven, FL 33881

$325,000

4 beds

2 baths

2,091 sq ft

House

5852 MARSH LANDING DR, WINTER HAVEN, FL,...

Community: Preserve at Lakeside Landings

Heritage Hills

3516 KINLEY BROOKE LN, CLERMONT, FL, 347..., Clermont, FL 34711

$420,000

3 beds

2 baths

1,879 sq ft

House

3516 KINLEY BROOKE LN, CLERMONT, FL, 347...

Community: Heritage Hills

Colonnades

4983 PLEASANT HOLLOW TRL, LAKELAND, FL, ..., Lakeland, FL 33811

$199,750

2 beds

2 baths

1,520 sq ft

House

4983 PLEASANT HOLLOW TRL, LAKELAND, FL, ...

Community: Colonnades

Cindy Certified

8138 DOBRE WAY, MELBOURNE, FL, 32940, Melbourne, FL 32940

$649,900

4 beds

2 baths

1,857 sq ft

House

8138 DOBRE WAY, MELBOURNE, FL, 32940

The Villages®

$375,000

3 beds

2 baths

1,854 sq ft

House

7815 SE 166TH HIBERNIA LN, THE VILLAGES,...

Community: The Villages®

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

Questions? Call us: (888) 625-4885

Gatherings of Lake Nona

7505 LAUREATE BLVD 2407, ORLANDO, FL, 32..., Orlando, FL 32827

$550,000

3 beds

2 baths

1,799 sq ft

Condo

7505 LAUREATE BLVD 2407, ORLANDO, FL, 32...

Community: Gatherings of Lake Nona

Del Webb at Viera

3484 BUBBLES CT, MELBOURNE, FL, 32940, Melbourne, FL 32940

$499,900

2 beds

2 baths

1,397 sq ft

House

3484 BUBBLES CT, MELBOURNE, FL, 32940

Community: Del Webb at Viera

Cindy Certified

8030 WAXWING CIR, MELBOURNE, FL, 32940, Melbourne, FL 32940

$1,550,000

3 beds

4 baths

2,750 sq ft

House

8030 WAXWING CIR, MELBOURNE, FL, 32940

Solivita

105 CUPOLA LOOP, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$395,000

2 beds

2 baths

2,066 sq ft

House

105 CUPOLA LOOP, KISSIMMEE, FL, 34759

Community: Solivita

Plantation Bay Golf & Country Club

773 COBBLESTONE WAY, ORMOND BEACH, FL, 3..., Ormond Beach, FL 32174

$599,000

2 beds

3 baths

2,115 sq ft

Townhouse

773 COBBLESTONE WAY, ORMOND BEACH, FL, 3...

Community: Plantation Bay Golf & Country Club

Gatherings of Lake Nona

7557 LAUREATE BLVD 6401, ORLANDO, FL, 32..., Orlando, FL 32827

$359,990

2 beds

2 baths

1,368 sq ft

Condo

7557 LAUREATE BLVD 6401, ORLANDO, FL, 32...

Community: Gatherings of Lake Nona

Plantation Bay Golf & Country Club

1280 HARWICK LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$543,900

4 beds

2 baths

2,476 sq ft

House

1280 HARWICK LN, ORMOND BEACH, FL, 32174

Community: Plantation Bay Golf & Country Club

The Villages®

$920,000

3 beds

2 baths

2,310 sq ft

House

2841 APACHE CT, THE VILLAGES, FL, 32163

Community: The Villages®

The Reserve at Victoria

1576 LAKE RESERVE DR, DELAND, FL, 32724, Deland, FL 32724

$672,000

3 beds

3 baths

2,437 sq ft

House

1576 LAKE RESERVE DR, DELAND, FL, 32724

Community: The Reserve at Victoria

Indian River Colony Club

1062 CONTINENTAL AVE, MELBOURNE, FL, 329..., Melbourne, FL 32940

$375,000

4 beds

3 baths

2,239 sq ft

House

1062 CONTINENTAL AVE, MELBOURNE, FL, 329...

Community: Indian River Colony Club

The Villages®

$475,000

3 beds

2 baths

1,569 sq ft

House

5738 CARLEY LOOP, THE VILLAGES, FL, 3216...

Community: The Villages®

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

Questions? Call us: (888) 625-4885

Solivita

1055 HARBOR RIDGE DR, KISSIMMEE, FL, 347..., Kissimmee, FL 34759

$279,000

3 beds

2 baths

1,590 sq ft

House

1055 HARBOR RIDGE DR, KISSIMMEE, FL, 347...

Community: Solivita

Cresswind at Victoria Gardens

300 BELLINGRATH TER, DELAND, FL, 32724, Deland, FL 32724

$525,000

2 beds

2 baths

2,435 sq ft

House

300 BELLINGRATH TER, DELAND, FL, 32724

Community: Cresswind at Victoria Gardens

The Villages®

$259,500

1 beds

1 baths

938 sq ft

Villa

5844 MARSH CT, THE VILLAGES, FL, 32163

Community: The Villages®

The Villages®

$274,900

2 beds

2 baths

1,156 sq ft

Villa

973 YORK TER, THE VILLAGES, FL, 32162

Community: The Villages®

Cindy Certified

80 PERGOLA PL, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$345,000

3 beds

2 baths

1,913 sq ft

188 PERSIMMON DR, PALM COAST, FL, 32164

Cindy Certified

3052 NAMASTE DR, CLERMONT, FL, 34714, Clermont, FL 34714

$887,000

74 beds

3 baths

2,199 sq ft

House

3052 NAMASTE DR, CLERMONT, FL, 34714

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

Questions? Call us: (888) 625-4885

The Villages®

$288,000

3 beds

2 baths

1,392 sq ft

House

17766 SE 91ST POPLAR TER, THE VILLAGES, ...

Community: The Villages®

Cresswind at Victoria Gardens

1314 EGGLESTON DR, DELAND, FL, 32724, Deland, FL 32724

$455,000

2 beds

2 baths

1,813 sq ft

House

1314 EGGLESTON DR, DELAND, FL, 32724

Community: Cresswind at Victoria Gardens

1…24 25 26 27 28 29 30 31 32 33 34 35 36…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 30

98 communities near Winter Park

2,698 homes near Winter Park

3 beds

2 baths

1,921 sq ft

House

4 beds

3 baths

2,326 sq ft

House

3 beds

2 baths

1,662 sq ft

House

3 beds

2 baths

1,677 sq ft

House

3 beds

3 baths

1,779 sq ft

House

4 beds

2 baths

1,858 sq ft

House

2 beds

3 baths

2,138 sq ft

Villa

2 beds

2 baths

1,549 sq ft

Condo

3 beds

3 baths

3,114 sq ft

House

2 beds

2 baths

1,205 sq ft

House

2 beds

2 baths

1,170 sq ft

House

4 beds

2 baths

2,091 sq ft

House

3 beds

2 baths

1,879 sq ft

House

2 beds

2 baths

1,520 sq ft

House

4 beds

2 baths

1,857 sq ft

House

3 beds

2 baths

1,854 sq ft

House

3 beds

2 baths

1,799 sq ft

Condo

2 beds

2 baths

1,397 sq ft

House

3 beds

4 baths

2,750 sq ft

House

2 beds