Winter Park, FL 55+ active adult communities & homes for sale - Page 19

2,377 homes near Winter Park

Sort by:

Relevance

4 rating (17 reviews)

The Villages®

<$100k - $2Ms

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

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

$300Ks - $1Ms

Grand Haven, Palm Coast, FL

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

Pelican Bay Daytona Beach

$100Ks - $400Ks

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 - $400Ks

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

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

Questions? Call us: (888) 625-4885

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

5 rating (2 reviews)

Heritage Isle

$200Ks - $500Ks

Heritage Isle, Viera, FL

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

3.8 rating (6 reviews)

Trilogy® Orlando

$200Ks - $600Ks

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

Del Webb at Viera

$400Ks - $1Ms

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

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)

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

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 - $800Ks

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

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

Questions? Call us: (888) 625-4885

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 - $800Ks

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

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

$300Ks - $400Ks

Royal Harbor, Tavares, FL

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

Lakeside Landings

$200Ks - $500Ks

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

1 rating (1 reviews)

Sullivan Ranch

$200Ks - $700Ks

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

6223 ATKINSON LN, THE VILLAGES, FL, 3216...

House

12463 SE 93RD COURT RD, SUMMERFIELD, FL,...

Community: Spruce Creek Country Club

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

Questions? Call us: (888) 625-4885

The Villages®

$329,999

3 beds

2 baths

1,398 sq ft

House

2294 TRAILWINDS TER, THE VILLAGES, FL, 3...

Community: The Villages®

Del Webb Orlando

300 DEL SOL AVE, DAVENPORT, FL, 33837, Davenport, FL 33837

$428,200

2 beds

2 baths

1,728 sq ft

House

300 DEL SOL AVE, DAVENPORT, FL, 33837

Community: Del Webb Orlando

The Villages®

$364,000

3 beds

2 baths

1,521 sq ft

House

995 JOINER PL, THE VILLAGES, FL, 32162

Community: The Villages®

Traditions at Lake Ruby

3686 PLYMOUTH DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884

$388,900

4 beds

3 baths

2,404 sq ft

House

3686 PLYMOUTH DR, WINTER HAVEN, FL, 3388...

Community: Traditions at Lake Ruby

Traditions at Lake Ruby

3987 BEDFORD AVE, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884

$358,000

2 beds

2 baths

1,817 sq ft

House

3987 BEDFORD AVE, WINTER HAVEN, FL, 3388...

Community: Traditions at Lake Ruby

Solivita

693 SAN RAPHAEL ST, POINCIANA, FL, 34759, Poinciana, FL 34759

$585,000

4 beds

3 baths

2,761 sq ft

House

693 SAN RAPHAEL ST, POINCIANA, FL, 34759

Community: Solivita

Heritage Isle

6488 VAN NESS DR, MELBOURNE, FL, 32940, Melbourne, FL 32940

$430,000

3 beds

2 baths

1,861 sq ft

House

6488 VAN NESS DR, MELBOURNE, FL, 32940

Community: Heritage Isle

New Heritage Isle

2510 CAMBERLY CIR, MELBOURNE, FL, 32940, Melbourne, FL 32940

$290,000

2 beds

2 baths

1,407 sq ft

Townhouse

2510 CAMBERLY CIR, MELBOURNE, FL, 32940

Community: Heritage Isle

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

Questions? Call us: (888) 625-4885

Harbor Hills Country Club

6008 APEX WAY, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$749,500

4 beds

3 baths

3,432 sq ft

House

6008 APEX WAY, LADY LAKE, FL, 32159

Community: Harbor Hills Country Club

The Villages®

$309,000

2 beds

2 baths

1,360 sq ft

House

304 SAN MARINO DR, THE VILLAGES, FL, 321...

Community: The Villages®

Plantation Bay Golf & Country Club

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

$555,000

3 beds

2 baths

2,029 sq ft

House

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

Community: Plantation Bay Golf & Country Club

Colonnades

$125,000

2 beds

2 baths

1,248 sq ft

Manufactured Home

4805 COLONNADES CIR, LAKELAND, FL, 33811

Community: Colonnades

Spruce Creek Country Club

9921 SE 138TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491

$299,900

2 beds

2 baths

1,872 sq ft

House

9921 SE 138TH LOOP, SUMMERFIELD, FL, 344...

Community: Spruce Creek Country Club

The Timbers at Everlands

1443 BLESSED ISLES DR NW, PALM BAY, FL, ..., Palm Bay, FL 32907

$528,000

4 beds

3 baths

2,638 sq ft

House

1443 BLESSED ISLES DR NW, PALM BAY, FL, ...

Community: The Timbers at Everlands

The Timbers at Everlands

1423 BLESSED ISLES DR NW, PALM BAY, FL, ..., Palm Bay, FL 32907

$483,160

3 beds

3 baths

2,470 sq ft

House

1423 BLESSED ISLES DR NW, PALM BAY, FL, ...

Community: The Timbers at Everlands

The Timbers at Everlands

913 VERONESE PL NW, PALM BAY, FL, 32907, Palm Bay, FL 32907

$443,220

3 beds

4 baths

2,389 sq ft

House

913 VERONESE PL NW, PALM BAY, FL, 32907

Community: The Timbers at Everlands

The Timbers at Everlands

1413 BLESSED ISLES DR NW, PALM BAY, FL, ..., Palm Bay, FL 32907

$475,895

3 beds

3 baths

2,325 sq ft

House

1413 BLESSED ISLES DR NW, PALM BAY, FL, ...

Community: The Timbers at Everlands

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

Questions? Call us: (888) 625-4885

The Timbers at Everlands

943 VERONESE PL NW, PALM BAY, FL, 32907, Palm Bay, FL 32907

$405,640

3 beds

3 baths

2,032 sq ft

House

943 VERONESE PL NW, PALM BAY, FL, 32907

Community: The Timbers at Everlands

The Timbers at Everlands

2522 ANTARUS DR NW, PALM BAY, FL, 32907, Palm Bay, FL 32907

$340,430

3 beds

3 baths

1,963 sq ft

House

2522 ANTARUS DR NW, PALM BAY, FL, 32907

Community: The Timbers at Everlands

The Timbers at Everlands

2662 ANTARUS DR NW, PALM BAY, FL, 32907, Palm Bay, FL 32907

$362,747

3 beds

3 baths

1,831 sq ft

House

2662 ANTARUS DR NW, PALM BAY, FL, 32907

Community: The Timbers at Everlands

The Timbers at Everlands

2672 ANTARUS DR NW, PALM BAY, FL, 32907, Palm Bay, FL 32907

$335,765

2 beds

3 baths

1,713 sq ft

House

2672 ANTARUS DR NW, PALM BAY, FL, 32907

Community: The Timbers at Everlands

Archers Mill

3313 ARCH AVE, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$439,990

4 beds

3 baths

2,108 sq ft

House

3313 ARCH AVE, ORMOND BEACH, FL, 32174

Community: Archers Mill

Venetian Bay

3604 ROMEA CIR, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168

$379,000

3 beds

2 baths

1,870 sq ft

Townhouse

3604 ROMEA CIR, NEW SMYRNA BEACH, FL, 32...

Community: Venetian Bay

Scottish Highlands

803 DUNDEE CIR, LEESBURG, FL, 34788, Leesburg, FL 34788

$259,000

2 beds

2 baths

1,436 sq ft

House

803 DUNDEE CIR, LEESBURG, FL, 34788

Community: Scottish Highlands

Pelican Bay Daytona Beach

105 WOOD DUCK CIR C, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119

$173,000

2 beds

2 baths

1,242 sq ft

Condo

105 WOOD DUCK CIR C, DAYTONA BEACH, FL, ...

Community: Pelican Bay Daytona Beach

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

Questions? Call us: (888) 625-4885

Halifax Plantation

3169 CONNEMARA DR, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174

$375,000

3 beds

2 baths

1,919 sq ft

House

3169 CONNEMARA DR, ORMOND BEACH, FL, 321...

Community: Halifax Plantation

Spruce Creek Country Club

9685 SE 136TH PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491

$319,500

2 beds

2 baths

1,873 sq ft

House

9685 SE 136TH PL, SUMMERFIELD, FL, 34491

Community: Spruce Creek Country Club

1…13 14 15 16 17 18 19 20 21 22 23 24 25…60

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

2,377 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: Jan 11, 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 19

90 communities near Winter Park

2,377 homes near Winter Park

2 beds

2 baths

1,425 sq ft

House

3 beds

2 baths

1,690 sq ft

House

2 beds

2 baths

1,312 sq ft

Villa

4 beds

2 baths

1,908 sq ft

House

2 beds

2 baths

1,203 sq ft

House

2 beds

2 baths

1,213 sq ft

House

3 beds

2 baths

1,790 sq ft

House

3 beds

3 baths

1,734 sq ft

House

3 beds

2 baths

2,444 sq ft

House

3 beds

2 baths

1,815 sq ft

House

3 beds

2 baths

1,741 sq ft

House

3 beds

2 baths

1,844 sq ft

House

3 beds

3 baths

2,459 sq ft

House

3 beds

2 baths

1,398 sq ft

House

2 beds

2 baths

1,728 sq ft

House

3 beds

2 baths

1,521 sq ft

House

4 beds

3 baths

2,404 sq ft

House

2 beds

2 baths

1,817 sq ft

House

4 beds

3 baths

2,761 sq ft

House

3 beds