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

2,487 homes near Winter Park

Sort by:

Relevance

4 rating (17 reviews)

The Villages®

<$100k - $1Ms

The Villages®, The Villages, FL

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

4.7 rating (18 reviews)

Solivita

$100Ks - $600Ks

Solivita, Kissimmee, FL

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

3.6 rating (48 reviews)

Latitude Margaritaville

$300Ks - $900Ks

Latitude Margaritaville, Daytona Beach, FL

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

5 rating (1 reviews)

Plantation Bay Golf &...

$200Ks - $4Ms

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

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

4.5 rating (11 reviews)

Spruce Creek Country Club

$200Ks - $500Ks

Spruce Creek Country Club, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1996 - 2007 | 3,250 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 - $500Ks

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

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

5 rating (7 reviews)

Kings Ridge

$200Ks - $400Ks

Kings Ridge, Clermont, FL

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

Grand Haven

$300Ks - $1Ms

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.

Pelican Bay Daytona Beach

$100Ks - $500Ks

Pelican Bay Daytona Beach, Daytona Beach, FL

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

4.7 rating (3 reviews)

Spruce Creek South

$100Ks - $300Ks

Spruce Creek South, Summerfield, FL

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

5 rating (1 reviews)

Cypress Lakes

$100Ks - $200Ks

Cypress Lakes, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 homes

5 rating (3 reviews)

Lake Ashton

$200Ks - $800Ks

Lake Ashton, Lake Wales, FL

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

Venetian Bay

$200Ks - $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

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 (2 reviews)

Heritage Isle

$200Ks - $500Ks

Heritage Isle, Viera, FL

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

5 rating (8 reviews)

Royal Highlands

$200Ks - $500Ks

Royal Highlands, Leesburg, FL

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

Del Webb at Viera

$300Ks - $800Ks

Del Webb at Viera, Melbourne, FL

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

5 rating (1 reviews)

VillageWalk at Lake Nona

$300Ks - $1Ms

VillageWalk at Lake Nona, Orlando, FL

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

5 rating (1 reviews)

Del Webb Sunbridge

$300Ks - $1Ms

Del Webb Sunbridge, St. Cloud, FL

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

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)

Sandpiper Golf & Coun...

$200Ks - $400Ks

Sandpiper Golf & Coun..., Lakeland, FL

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

3.6 rating (5 reviews)

Heritage Hills

$200Ks - $500Ks

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 - $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

Halifax Plantation

$200Ks - $700Ks

Halifax Plantation, Ormond Beach, FL

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

Breakaway Trails

$400Ks - $700Ks

Breakaway Trails, Ormond Beach, FL

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

4 rating (4 reviews)

Lakes of Mount Dora

$400Ks - $900Ks

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

$200Ks - $1Ms

Harbor Hills Country Club, Lady Lake, FL

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

4.8 rating (6 reviews)

Highland Lakes

$100Ks - $300Ks

Highland Lakes, Leesburg, FL

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

4.4 rating (16 reviews)

Del Webb Orlando

$300Ks - $400Ks

Del Webb Orlando, Davenport, FL

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

5 rating (2 reviews)

Bridgewater at Viera

$300Ks - $600Ks

Bridgewater at Viera, Melbourne, FL

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

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

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

Questions? Call us: (888) 625-4885

3.9 rating (7 reviews)

Summit Greens

$300Ks - $400Ks

Summit Greens, Clermont, FL

Resale Only | 55+ age-restricted | Built 2001 - 2019 | 769 homes

5 rating (1 reviews)

Royal Harbor

$200Ks - $400Ks

Royal Harbor, Tavares, FL

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

Lakeside Landings

$200Ks - $600Ks

Lakeside Landings, Oxford, FL

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

1 rating (1 reviews)

Sullivan Ranch

$300Ks - $600Ks

Sullivan Ranch, Mount Dora, FL

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

Highland Fairways

$100Ks - $300Ks

Highland Fairways, Lakeland, FL

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

27046 ROANOKE DR, LEESBURG, FL, 34748

Community: Arlington Ridge

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

Questions? Call us: (888) 625-4885

Ridgehaven

422 BROOKHAVEN TRL, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174

$513,410

4 beds

3 baths

2,487 sq ft

House

422 BROOKHAVEN TRL, ORMOND BEACH, FL, 32...

Community: Ridgehaven

Del Webb Orlando

540 PAMPLONA PL, DAVENPORT, FL, 33837, Davenport, FL 33837

$330,000

2 beds

3 baths

1,772 sq ft

House

540 PAMPLONA PL, DAVENPORT, FL, 33837

Community: Del Webb Orlando

Ridgehaven

434 BROOKHAVEN TRL, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174

$606,420

5 beds

5 baths

3,807 sq ft

House

434 BROOKHAVEN TRL, ORMOND BEACH, FL, 32...

Community: Ridgehaven

Ridgehaven

441 BROOKHAVEN TRL, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174

$543,290

4 beds

3 baths

2,791 sq ft

House

441 BROOKHAVEN TRL, ORMOND BEACH, FL, 32...

Community: Ridgehaven

Spruce Creek Country Club

9175 SE 118TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491

$269,900

2 beds

2 baths

1,488 sq ft

House

9175 SE 118TH LOOP, SUMMERFIELD, FL, 344...

Community: Spruce Creek Country Club

The Villages®

$329,900

2 beds

2 baths

1,286 sq ft

Villa

2865 JUDAH ST, THE VILLAGES, FL, 32163

Community: The Villages®

The Villages®

$358,789

2 beds

2 baths

2,170 sq ft

Villa

1067 CARVER CT, THE VILLAGES, FL, 32163

Community: The Villages®

The Villages®

$299,000

2 beds

2 baths

1,100 sq ft

House

442 PACE LN, THE VILLAGES, FL, 32162

Community: The Villages®

Plantation at Leesburg

4712 BELLE GRV, LEESBURG, FL, 34748, Leesburg, FL 34748

$220,000

3 beds

2 baths

1,524 sq ft

Manufactured Home

4712 BELLE GRV, LEESBURG, FL, 34748

Community: Plantation at Leesburg

Harbor Hills Country Club

39342 HARBOR HILLS BLVD, LADY LAKE, FL, ..., Lady Lake, FL 32159

$489,000

3 beds

2 baths

2,233 sq ft

House

39342 HARBOR HILLS BLVD, LADY LAKE, FL, ...

Halfplex

1775 COUNTRY CLUB BLVD, MOUNT DORA, FL, ...

3205 BAILEY ANN DR, ORMOND BEACH, FL, 32...

Community: Halifax Plantation

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

Questions? Call us: (888) 625-4885

The Villages®

$214,000

2 beds

2 baths

936 sq ft

Manufactured Home

1336 E SCHWARTZ BLVD, THE VILLAGES, FL, ...

Community: The Villages®

Twin Lakes

4911 DRAWDY CT, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772

$580,000

3 beds

2 baths

3,122 sq ft

House

4911 DRAWDY CT, SAINT CLOUD, FL, 34772

Community: Twin Lakes

The Villages®

$549,900

3 beds

2 baths

1,935 sq ft

House

3526 CLUSTER CT, THE VILLAGES, FL, 32163

Community: The Villages®

Highland Lakes

6131 WILANDER ST, LEESBURG, FL, 34748, Leesburg, FL 34748

$319,900

3 beds

2 baths

2,027 sq ft

House

6131 WILANDER ST, LEESBURG, FL, 34748

Community: Highland Lakes

The Villages®

$424,900

3 beds

2 baths

1,840 sq ft

House

1676 VAN BUREN WAY, THE VILLAGES, FL, 32...

Community: The Villages®

Palms at Serenoa

17613 SUMMERSWEET WAY, CLERMONT, FL, 347..., Clermont, FL 34714

$335,000

2 beds

2 baths

1,627 sq ft

House

17613 SUMMERSWEET WAY, CLERMONT, FL, 347...

Community: Palms at Serenoa

Harbor Hills Country Club

5235 GREENS DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$1,450,000

4 beds

4 baths

3,836 sq ft

House

5235 GREENS DR, LADY LAKE, FL, 32159

Community: Harbor Hills Country Club

The Villages®

$511,000

3 beds

2 baths

1,633 sq ft

Villa

4686 HILES PL, THE VILLAGES, FL, 32163

Community: The Villages®

The Villages®

$249,000

2 beds

2 baths

1,156 sq ft

Villa

1382 ZEST AVE, THE VILLAGES, FL, 32163

Community: The Villages®

Spruce Creek Country Club

12024 SE 91ST CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$249,900

2 beds

2 baths

1,488 sq ft

House

12024 SE 91ST CIR, SUMMERFIELD, FL, 3449...

House

304 BRIGADOON CIR, LEESBURG, FL, 34788

Community: Scottish Highlands

1…29 30 31 32 33 34 35 36 37 38 39 40 41…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

2,487 homes near Winter Park

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.
© 2025 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: Nov 30, 2025.
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

90 communities near Winter Park

2,487 homes near Winter Park

2 beds

3 baths

2,012 sq ft

House

2 beds

2 baths

1,751 sq ft

House

3 beds

2 baths

1,927 sq ft

House

4 beds

3 baths

2,544 sq ft

House

2 beds

2 baths

1,532 sq ft

House

4 beds

3 baths

2,487 sq ft

House

2 beds

3 baths

1,772 sq ft

House

5 beds

5 baths

3,807 sq ft

House

4 beds

3 baths

2,791 sq ft

House

2 beds

2 baths

1,488 sq ft

House

2 beds

2 baths

1,286 sq ft

Villa

2 beds

2 baths

2,170 sq ft

Villa

2 beds

2 baths

1,100 sq ft

House

3 beds

2 baths

1,524 sq ft

Manufactured Home

3 beds

2 baths

2,233 sq ft

House

2 beds

2 baths

1,627 sq ft

House

3 beds

2 baths

1,974 sq ft

House

3 beds

2 baths

1,542 sq ft

House

2 beds

2 baths

1,032 sq ft

House

2 beds