Winter Park, FL 55+ active adult communities & homes for sale - Page 53

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

3713 DOUNE WAY, CLERMONT, FL, 34711

Community: Kings Ridge

Huntington at Hunter's Ridge

59 FAWN HAVEN TRL, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174

$559,000

3 beds

2 baths

1,852 sq ft

House

59 FAWN HAVEN TRL, ORMOND BEACH, FL, 321...

Community: Huntington at Hunter's Ridge

Plantation at Leesburg

25440 CRESTWATER DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$329,000

3 beds

2 baths

2,077 sq ft

House

25440 CRESTWATER DR, LEESBURG, FL, 34748

Community: Plantation at Leesburg

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

Questions? Call us: (888) 625-4885

Sullivan Ranch

22004 BELGIAN CT, MOUNT DORA, FL, 32757, Mount Dora, FL 32757

$309,699

3 beds

2 baths

1,437 sq ft

House

22004 BELGIAN CT, MOUNT DORA, FL, 32757

Community: Sullivan Ranch

Lake Ashton

4172 DUNMORE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859

$580,000

3 beds

2 baths

2,284 sq ft

House

4172 DUNMORE DR, LAKE WALES, FL, 33859

Community: Lake Ashton

Lakes of Mount Dora

8788 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757

$519,900

3 beds

2 baths

1,985 sq ft

House

8788 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...

Community: Lakes of Mount Dora

Colonnades

$249,900

2 beds

2 baths

1,305 sq ft

House

1608 COLONNADES CIR, LAKELAND, FL, 33811

Community: Colonnades

Sandpiper Golf & Country Club

6189 MAGPIE DR, LAKELAND, FL, 33809, Lakeland, FL 33809

$475,000

3 beds

2 baths

2,009 sq ft

House

6189 MAGPIE DR, LAKELAND, FL, 33809

Community: Sandpiper Golf & Country Club

Plantation Bay Golf & Country Club

22 JASMINE RUN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$235,000

2 beds

2 baths

1,596 sq ft

House

22 JASMINE RUN, ORMOND BEACH, FL, 32174

Community: Plantation Bay Golf & Country Club

Grand Haven

18 PLAYERS CIR, PALM COAST, FL, 32137, Palm Coast, FL 32137

$619,000

3 beds

3 baths

2,529 sq ft

House

18 PLAYERS CIR, PALM COAST, FL, 32137

Community: Grand Haven

Pelican Bay Daytona Beach

144 AVOCET CT, DAYTONA BEACH, FL, 32119, Daytona Beach, FL 32119

$299,900

3 beds

3 baths

2,072 sq ft

Townhouse

144 AVOCET CT, DAYTONA BEACH, FL, 32119

Community: Pelican Bay Daytona Beach

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

1290 MAYFLOWER AVE, MELBOURNE, FL, 32940

Community: Indian River Colony Club

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

Questions? Call us: (888) 625-4885

Del Webb Sunbridge

2973 CHERRY BLOSSOM LOOP, SAINT CLOUD, F..., Saint Cloud, FL 34771

$358,980

2 beds

2 baths

1,584 sq ft

Villa

2973 CHERRY BLOSSOM LOOP, SAINT CLOUD, F...

Community: Del Webb Sunbridge

Plantation Bay Golf & Country Club

17 MAGNOLIA DR N, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174

$500,000

4 beds

4 baths

2,308 sq ft

House

17 MAGNOLIA DR N, ORMOND BEACH, FL, 3217...

Community: Plantation Bay Golf & Country Club

The Villages®

1025 AVALON AVE, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$330,000

2 beds

2 baths

1,268 sq ft

Villa

1025 AVALON AVE, LADY LAKE, FL, 32159

Community: The Villages®

Harbor Hills Country Club

39023 GRIFFIN LNDG, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$564,900

3 beds

3 baths

2,833 sq ft

House

39023 GRIFFIN LNDG, LADY LAKE, FL, 32159

Community: Harbor Hills Country Club

The Villages®

1725 HILTON HEAD BLVD, LADY LAKE, FL, 32..., Lady Lake, FL 32159

$174,000

2 beds

2 baths

1,092 sq ft

Manufactured Home

1725 HILTON HEAD BLVD, LADY LAKE, FL, 32...

Community: The Villages®

Traditions at Lake Ruby

3020 CANEEL ST, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884

$219,900

2 beds

2 baths

1,521 sq ft

Villa

3020 CANEEL ST, WINTER HAVEN, FL, 33884

Community: Traditions at Lake Ruby

The Villages®

$309,500

2 beds

2 baths

1,516 sq ft

House

17700 SE 92ND GRANTHAM TER, THE VILLAGES...

Community: The Villages®

Indian River Colony Club

1340 DEMOCRACY AVE, MELBOURNE, FL, 32940, Melbourne, FL 32940

$399,000

4 beds

3 baths

2,361 sq ft

House

1340 DEMOCRACY AVE, MELBOURNE, FL, 32940

Community: Indian River Colony Club

Grand Haven

200 RIVERFRONT DR B303, PALM COAST, FL, ..., Palm Coast, FL 32137

$379,900

3 beds

2 baths

1,762 sq ft

Condo

200 RIVERFRONT DR B303, PALM COAST, FL, ...

House

4614 RIVER RIDGE DR, LEESBURG, FL, 34748

Community: Plantation at Leesburg

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

Questions? Call us: (888) 625-4885

Breakaway Trails

180 BLACK HICKORY WAY, ORMOND BEACH, FL,..., Ormond Beach, FL 32174

$505,000

3 beds

2 baths

1,983 sq ft

House

180 BLACK HICKORY WAY, ORMOND BEACH, FL,...

Community: Breakaway Trails

Alhambra Villas Condominiums

239 N HILL AVE # 110, DELAND, FL, 32724, Deland, FL 32724

$199,000

2 beds

2 baths

1,091 sq ft

Condo

239 N HILL AVE # 110, DELAND, FL, 32724

Community: Alhambra Villas Condominiums

1…47 48 49 50 51 52 53 54 55 56 57 58 59…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 53

90 communities near Winter Park

2,377 homes near Winter Park

3 beds

3 baths

1,718 sq ft

House

2 beds

2 baths

1,559 sq ft

House

2 beds

2 baths

1,705 sq ft

House

3 beds

2 baths

1,852 sq ft

House

3 beds

2 baths

2,077 sq ft

House

3 beds

2 baths

1,437 sq ft

House

3 beds

2 baths

2,284 sq ft

House

3 beds

2 baths

1,985 sq ft

House

2 beds

2 baths

1,305 sq ft

House

3 beds

2 baths

2,009 sq ft

House

2 beds

2 baths

1,596 sq ft

House

3 beds

3 baths

2,529 sq ft

House

3 beds

3 baths

2,072 sq ft

Townhouse

3 beds

2 baths

1,598 sq ft

House

2 beds

3 baths

2,053 sq ft

House

3 beds

2 baths

2,011 sq ft

House

2 beds

2 baths

1,595 sq ft

House

3 beds

2 baths

2,028 sq ft

House

3 beds

2 baths

1,764 sq ft

House

4 beds