Winter Park, FL 55+ active adult communities & homes for sale - Page 56

2,414 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

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

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

Venetian Bay

$300ks - $1Ms

Venetian Bay, New Smyrna Beach, FL

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

5 rating (3 reviews)

Stonecrest

$200ks - $500ks

Stonecrest, Summerfield, FL

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

Grand Haven

$200ks - $800ks

Grand Haven, Palm Coast, FL

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

2.8 rating (6 reviews)

Arlington Ridge

$200ks - $500ks

Arlington Ridge, Leesburg, FL

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

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 (7 reviews)

Kings Ridge

$200ks - $400ks

Kings Ridge, Clermont, FL

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

Pelican Bay Daytona Beach

$100ks - $600ks

Pelican Bay Daytona Beach, Daytona Beach, FL

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

4 rating (4 reviews)

Lakes of Mount Dora

$300ks - $1Ms

Lakes of Mount Dora, Mount Dora, FL

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

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 (1 reviews)

Cresswind at Victoria Gar...

$200ks - $500ks

Cresswind at Victoria Gar..., DeLand, FL

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

Summer Trees

$200ks - $400ks

Summer Trees, Port Orange, FL

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

The Lakes at Harmony

$200ks - $400ks

The Lakes at Harmony, Harmony, FL

New and Resale | 55+ age-restricted | Built 2016 - present | 400 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 (2 reviews)

Heritage Isle

$300ks - $500ks

Heritage Isle, Viera, FL

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

5 rating (8 reviews)

Pennbrooke Fairways

<$100k - $300ks

Pennbrooke Fairways, Leesburg, FL

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

Breakaway Trails

$400ks - $800ks

Breakaway Trails, Ormond Beach, FL

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

Four Seasons at Orlando

$300ks - $600ks

Four Seasons at Orlando, Kissimmee, FL

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

Ridgehaven

$300ks - $600ks

Ridgehaven, Ormond Beach, FL

New Construction | 55+ age-restricted

Scottish Highlands

$100ks - $200ks

Scottish Highlands, Leesburg, FL

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

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)

VillageWalk at Lake Nona

$300ks - $700ks

VillageWalk at Lake Nona, Orlando, FL

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

Foxwood Lake Estates

$100ks - $200ks

Foxwood Lake Estates, Lakeland, FL

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

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

Questions? Call us: (888) 625-4885

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

5 rating (2 reviews)

Bridgewater at Viera

$300ks - $800ks

Bridgewater at Viera, Melbourne, FL

Resale Only | 55+ age-restricted | Built 2017 - 2023 | 870 homes

1 2...3

Royal Highlands

4802 GLEN COE ST, LEESBURG, FL, 34748, Leesburg, FL 34748

$425,000

2 beds

2 baths

3,034 sq ft

House

4802 GLEN COE ST, LEESBURG, FL, 34748

Community: Royal Highlands

Twin Lakes

2491 YELLOW BRICK RD, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772

$299,999

2 beds

2 baths

1,464 sq ft

Halfplex

2491 YELLOW BRICK RD, SAINT CLOUD, FL, 3...

Community: Twin Lakes

Heritage Hills

3538 BELLAND CIR B, CLERMONT, FL, 34711, Clermont, FL 34711

$284,000

2 beds

2 baths

1,374 sq ft

Villa

3538 BELLAND CIR B, CLERMONT, FL, 34711

Community: Heritage Hills

Harbor Hills Country Club

39640 HARBOR HILLS BLVD, LADY LAKE, FL, ..., Lady Lake, FL 32159

$497,500

3 beds

3 baths

2,531 sq ft

House

39640 HARBOR HILLS BLVD, LADY LAKE, FL, ...

Community: Harbor Hills Country Club

Lake James

$495,900

3 beds

2 baths

1,886 sq ft

House

7911 LAKE JAMES BLVD, LAKELAND, FL, 3381...

Villa

1991 KEY BAY TRL, KISSIMMEE, FL, 34747

Community: Four Seasons at Orlando

Latitude Margaritaville

663 LOST SHAKER WAY, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124

$429,000

2 beds

2 baths

1,464 sq ft

House

663 LOST SHAKER WAY, DAYTONA BEACH, FL, ...

Community: Latitude Margaritaville

Grand Haven

6 POINT DORAL CT, PALM COAST, FL, 32137, Palm Coast, FL 32137

$438,900

3 beds

2 baths

1,542 sq ft

House

6 POINT DORAL CT, PALM COAST, FL, 32137

Community: Grand Haven

Plantation at Leesburg

25119 CRANES ROOST CIR, LEESBURG, FL, 34..., Leesburg, FL 34748

$224,000

2 beds

2 baths

1,328 sq ft

House

25119 CRANES ROOST CIR, LEESBURG, FL, 34...

Community: Plantation at Leesburg

Pelican Bay Daytona Beach

236 GULL DR, DAYTONA BEACH, FL, 32119, Daytona Beach, FL 32119

$279,900

2 beds

2 baths

2,100 sq ft

House

236 GULL DR, DAYTONA BEACH, FL, 32119

Community: Pelican Bay Daytona Beach

Sandpiper Golf & Country Club

6381 EGRET DR 28, LAKELAND, FL, 33809, Lakeland, FL 33809

$214,000

2 beds

2 baths

1,053 sq ft

Villa

6381 EGRET DR 28, LAKELAND, FL, 33809

Community: Sandpiper Golf & Country Club

Summer Trees

125 CROOKED PINE RD, PORT ORANGE, FL, 32..., Port Orange, FL 32128

$285,000

2 beds

2 baths

1,855 sq ft

House

125 CROOKED PINE RD, PORT ORANGE, FL, 32...

Community: Summer Trees

Plantation Bay Golf & Country Club

46 LONGRIDGE LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$435,000

2 beds

2 baths

1,529 sq ft

Townhouse

46 LONGRIDGE LN, ORMOND BEACH, FL, 32174

Community: Plantation Bay Golf & Country Club

Solivita

157 SAND PIPER DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$314,500

3 beds

3 baths

2,267 sq ft

House

157 SAND PIPER DR, KISSIMMEE, FL, 34759

Community: Solivita

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

Questions? Call us: (888) 625-4885

Sullivan Ranch

30113 JUTLAND CT, MOUNT DORA, FL, 32757, Mount Dora, FL 32757

$619,900

5 beds

4 baths

3,320 sq ft

House

30113 JUTLAND CT, MOUNT DORA, FL, 32757

Community: Sullivan Ranch

Plantation Bay Golf & Country Club

1283 ROYAL POINTE LN, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174

$535,000

3 beds

2 baths

2,029 sq ft

House

1283 ROYAL POINTE LN, ORMOND BEACH, FL, ...

Community: Plantation Bay Golf & Country Club

The Villages®

12406 NE 50TH VW, OXFORD, FL, 34484, Oxford, FL 34484

$277,500

4 beds

4 baths

2,096 sq ft

House

12406 NE 50TH VW, OXFORD, FL, 34484

Community: The Villages®

Summer Trees

55 CROOKED PINE RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128

$244,000

3 beds

2 baths

1,775 sq ft

House

55 CROOKED PINE RD, PORT ORANGE, FL, 321...

Community: Summer Trees

Stonecrest

17520 SE 112TH AVE, SUMMERFIELD, FL, 344..., Summerfield, FL 34491

$299,000

2 beds

2 baths

1,402 sq ft

House

17520 SE 112TH AVE, SUMMERFIELD, FL, 344...

Community: Stonecrest

VillageWalk at Lake Nona

11887 DELFINA LN, ORLANDO, FL, 32827, Orlando, FL 32827

$439,000

2 beds

2 baths

1,708 sq ft

House

11887 DELFINA LN, ORLANDO, FL, 32827

Community: VillageWalk at Lake Nona

Stonecrest

17076 SE 115TH TERRACE RD, SUMMERFIELD, ..., Summerfield, FL 34491

$279,000

3 beds

2 baths

1,752 sq ft

House

17076 SE 115TH TERRACE RD, SUMMERFIELD, ...

Community: Stonecrest

Pennbrooke Fairways

32716 WESTWOOD LOOP, LEESBURG, FL, 34748, Leesburg, FL 34748

$228,900

2 beds

2 baths

1,370 sq ft

House

32716 WESTWOOD LOOP, LEESBURG, FL, 34748

Community: Pennbrooke Fairways

Del Webb Orlando

507 CADIZ DR, DAVENPORT, FL, 33837, Davenport, FL 33837

$399,900

4 beds

3 baths

2,616 sq ft

House

507 CADIZ DR, DAVENPORT, FL, 33837

Community: Del Webb Orlando

Cresswind at Victoria Gardens

115 HERON POINT WAY, DELAND, FL, 32724, Deland, FL 32724

$299,000

3 beds

2 baths

1,773 sq ft

House

115 HERON POINT WAY, DELAND, FL, 32724

Community: Cresswind at Victoria Gardens

Pelican Bay Daytona Beach

150 BLUE HERON DR B, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119

$230,900

3 beds

2 baths

1,365 sq ft

Condo

150 BLUE HERON DR B, DAYTONA BEACH, FL, ...

House

9667 SE 173RD LN, SUMMERFIELD, FL, 34491

21 JASMINE RUN, ORMOND BEACH, FL, 32174

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

Venetian Bay

668 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168

$665,138

5 beds

4 baths

3,221 sq ft

House

668 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ...

Community: Venetian Bay

Venetian Bay

672 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168

$625,684

4 beds

4 baths

2,748 sq ft

House

672 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ...

Community: Venetian Bay

1…48 49 50 51 52 53 54 55 56 57 58 59 60…61

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 [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

2,414 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: May 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 56

93 communities near Winter Park

2,414 homes near Winter Park

2 beds

2 baths

3,034 sq ft

House

2 beds

2 baths

1,464 sq ft

Halfplex

2 beds

2 baths

1,374 sq ft

Villa

3 beds

3 baths

2,531 sq ft

House

3 beds

2 baths

1,886 sq ft

House

2 beds

2 baths

1,368 sq ft

Condo

3 beds

2 baths

2,065 sq ft

House

2 beds

2 baths

1,437 sq ft

Villa

2 beds

2 baths

1,464 sq ft

House

3 beds

2 baths

1,542 sq ft

House

2 beds

2 baths

1,328 sq ft

House

2 beds

2 baths

2,100 sq ft

House

2 beds

2 baths

1,053 sq ft

Villa

2 beds

2 baths

1,855 sq ft

House

2 beds

2 baths

1,529 sq ft

Townhouse

3 beds

3 baths

2,267 sq ft

House

5 beds

4 baths

3,320 sq ft

House

3 beds

2 baths

2,029 sq ft

House

4 beds

4 baths

2,096 sq ft

House

3 beds