Winter Park, FL 55+ active adult communities & homes for sale - Page 44

2,698 homes near Winter Park

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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

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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

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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

14 POWDER HILL LN, PALM COAST, FL, 32164

Highland Fairways

3250 PEBBLE BEND DR, LAKELAND, FL, 33810, Lakeland, FL 33810

$239,900

2 beds

2 baths

1,092 sq ft

House

3250 PEBBLE BEND DR, LAKELAND, FL, 33810

House

723 HEATHROW AVE, THE VILLAGES, FL, 3215...

6807 SUNRISE COVE DR, CLERMONT, FL, 3471...

House

754 GRAND RESERVE DR, BUNNELL, FL, 32110

Legacy of Leesburg

5901 CANDLE GLOW PL, LEESBURG, FL, 34748, Leesburg, FL 34748

$320,000

3 beds

2 baths

1,978 sq ft

House

5901 CANDLE GLOW PL, LEESBURG, FL, 34748

Community: Legacy of Leesburg

Plantation Bay Golf & Country Club

501 WINGSPAN DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$1,099,000

3 beds

3 baths

House

501 WINGSPAN DR, ORMOND BEACH, FL, 32174

Community: Plantation Bay Golf & Country Club

Twin Lakes

5003 DANCY LN, ST CLOUD, FL, 34772, St Cloud, FL 34772

$595,000

3 beds

3 baths

2,293 sq ft

House

5003 DANCY LN, ST CLOUD, FL, 34772

3042 KINGSMAN TRL, ORMOND BEACH, FL, 321...

The Villages®

$289,000

2 beds

2 baths

1,240 sq ft

House

1070 BERKSHIRE PL, THE VILLAGES, FL, 321...

Community: The Villages®

Spruce Creek South

9427 SE 174TH PLACE RD, SUMMERFIELD, FL,..., Summerfield, FL 34491

$189,900

2 beds

1 baths

816 sq ft

House

9427 SE 174TH PLACE RD, SUMMERFIELD, FL,...

Community: Spruce Creek South

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

Questions? Call us: (888) 625-4885

Del Webb Oasis

13361 SUNNY RETREAT LN, WINTER GARDEN, F..., Winter Garden, FL 34787

$859,900

4 beds

3 baths

3,172 sq ft

House

13361 SUNNY RETREAT LN, WINTER GARDEN, F...

Community: Del Webb Oasis

Cindy Certified

2975 PARKFIELD RD, ST CLOUD, FL, 34772, St Cloud, FL 34772

$399,990

4 beds

3 baths

2,098 sq ft

House

2975 PARKFIELD RD, ST CLOUD, FL, 34772

Solivita

2316 PALM TREE DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$296,000

2 beds

2 baths

1,539 sq ft

Villa

2316 PALM TREE DR, KISSIMMEE, FL, 34759

Community: Solivita

Spruce Creek Country Club

12603 SE 90TH TER, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$309,900

2 beds

2 baths

1,596 sq ft

House

12603 SE 90TH TER, SUMMERFIELD, FL, 3449...

Community: Spruce Creek Country Club

Solivita

624 GRAND CANAL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$268,500

2 beds

2 baths

1,543 sq ft

House

624 GRAND CANAL DR, KISSIMMEE, FL, 34759

Community: Solivita

Grand Haven

14 EGRET DR, PALM COAST, FL, 32137, Palm Coast, FL 32137

$548,000

3 beds

2 baths

2,456 sq ft

House

14 EGRET DR, PALM COAST, FL, 32137

Community: Grand Haven

The Villages®

$295,000

3 beds

2 baths

1,265 sq ft

House

9603 SE 171ST ARGYLL ST, THE VILLAGES, F...

Community: The Villages®

Sullivan Ranch

30115 KLADRUBY PT, MOUNT DORA, FL, 32757, Mount Dora, FL 32757

$468,000

4 beds

3 baths

2,432 sq ft

House

30115 KLADRUBY PT, MOUNT DORA, FL, 32757

Community: Sullivan Ranch

Lake Ashton

5308 GREEN DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884

$249,900

3 beds

2 baths

1,495 sq ft

House

5308 GREEN DR, WINTER HAVEN, FL, 33884

Community: Lake Ashton

The Villages®

$624,900

3 beds

3 baths

2,488 sq ft

House

3095 KRAMER CT, THE VILLAGES, FL, 32163

Community: The Villages®

Lake Ashton

1061 SAWGRASS DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884

$449,900

3 beds

2 baths

2,069 sq ft

House

1061 SAWGRASS DR, WINTER HAVEN, FL, 3388...

Community: Lake Ashton

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

Questions? Call us: (888) 625-4885

Cindy Certified

2039 ROSEWOOD CIR, LAKELAND, FL, 33810, Lakeland, FL 33810

$370,000

3 beds

2 baths

1,845 sq ft

House

2039 ROSEWOOD CIR, LAKELAND, FL, 33810

The Villages®

$588,000

3 beds

2 baths

1,939 sq ft

House

486 INDEPENDENCE PATH, THE VILLAGES, FL,...

Community: The Villages®

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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.

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2,698 homes

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Winter Park, FL 55+ active adult communities & homes for sale - Page 44

98 communities near Winter Park

2,698 homes near Winter Park

2 beds

2 baths

2,213 sq ft

House

2 beds

2 baths

918 sq ft

Villa

3 beds

2 baths

2,523 sq ft

House

4 beds

2 baths

1,800 sq ft

House

2 beds

2 baths

1,092 sq ft

House

3 beds

2 baths

1,709 sq ft

House

2 beds

2 baths

1,925 sq ft

House

2 beds

2 baths

768 sq ft

Manufactured Home

2 beds

2 baths

1,352 sq ft

House

2 beds

2 baths

1,558 sq ft

House

3 beds

2 baths

1,959 sq ft

House

3 beds

2 baths

1,392 sq ft

House

3 beds

2 baths

1,883 sq ft

House

3 beds

3 baths

2,650 sq ft

House

3 beds

2 baths

2,028 sq ft

House

3 beds

2 baths

1,943 sq ft

House

3 beds

2 baths

2,054 sq ft

House

2 beds

2 baths

1,655 sq ft

House

3 beds

2 baths

1,402 sq ft

House

3 beds