Winter Park, FL 55+ active adult communities & homes for sale - Page 26

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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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

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

Halifax Plantation

$300ks - $1Ms

Halifax Plantation, Ormond Beach, FL

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

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

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

Scottish Highlands

$100ks - $200ks

Scottish Highlands, Leesburg, FL

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

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Questions? Call us: (888) 625-4885

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

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

Breakaway Trails

$400ks - $800ks

Breakaway Trails, Ormond Beach, FL

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

4.8 rating (6 reviews)

Highland Lakes

$100ks - $200ks

Highland Lakes, Leesburg, FL

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

Del Webb at Viera

$400ks - $1Ms

Del Webb at Viera, Melbourne, FL

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

Highland Fairways

$100ks - $300ks

Highland Fairways, Lakeland, FL

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

1 2...3

Spruce Creek Country Club

13785 SE 84TH CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491

$269,000

2 beds

2 beds

3 baths

2,204 sq ft

House

4817 SABLE RIDGE CT, LEESBURG, FL, 34748

Community: Plantation at Leesburg

Plantation at Leesburg

5350 ASTOR ST, LEESBURG, FL, 34748, Leesburg, FL 34748

$259,900

2 beds

2 baths

1,665 sq ft

House

5350 ASTOR ST, 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

Huntington at Hunter's Ridge

6 FOX LAIR CT, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$357,500

3 beds

2 baths

1,637 sq ft

House

6 FOX LAIR CT, ORMOND BEACH, FL, 32174

Community: Huntington at Hunter's Ridge

Indian River Colony Club

1309 PILGRIM AVE, MELBOURNE, FL, 32940, Melbourne, FL 32940

$285,000

2 beds

2 baths

1,868 sq ft

House

1309 PILGRIM AVE, MELBOURNE, FL, 32940

Community: Indian River Colony Club

Spruce Creek Country Club

13806 SE 93RD AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$305,000

2 beds

2 baths

1,346 sq ft

House

13806 SE 93RD AVE, SUMMERFIELD, FL, 3449...

Community: Spruce Creek Country Club

Spruce Creek Country Club

11985 SE 91ST CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$339,900

2 beds

2 baths

1,591 sq ft

House

11985 SE 91ST CIR, SUMMERFIELD, FL, 3449...

Community: Spruce Creek Country Club

Twin Lakes

2374 DATURA LOOP, ST CLOUD, FL, 34772, St Cloud, FL 34772

$304,000

2 beds

2 baths

1,464 sq ft

Villa

2374 DATURA LOOP, ST CLOUD, FL, 34772

Community: Twin Lakes

The Villages®

802 OAK BLVD, WILDWOOD, FL, 34785, Wildwood, FL 34785

$189,900

2 beds

4 baths

1,508 sq ft

Manufactured Home

802 OAK BLVD, WILDWOOD, FL, 34785

Community: The Villages®

Cindy Certified

1836 ANDOVER ST, PALM BAY, FL, 32907, Palm Bay, FL 32907

$350,000

4 beds

2 baths

1,827 sq ft

House

1836 ANDOVER ST, PALM BAY, FL, 32907

Latitude Margaritaville

156 MARGARITAVILLE AVE, DAYTONA BEACH, F..., Daytona Beach, FL 32124

$465,000

2 beds

2 baths

1,563 sq ft

House

156 MARGARITAVILLE AVE, DAYTONA BEACH, F...

Community: Latitude Margaritaville

Cindy Certified

1847 BUCKEYE RD, DAVENPORT, FL, 33837, Davenport, FL 33837

$329,990

3 beds

2 baths

1,725 sq ft

House

1847 BUCKEYE RD, DAVENPORT, FL, 33837

Pelican Bay Daytona Beach

100 KINGBIRD CIR 1040, DAYTONA BEACH, FL..., Daytona Beach, FL 32119

$199,900

2 beds

2 baths

1,500 sq ft

Condo

100 KINGBIRD CIR 1040, DAYTONA BEACH, FL...

Community: Pelican Bay Daytona Beach

Cindy Certified

120 PANDA WAY, DAVENPORT, FL, 33837, Davenport, FL 33837

$340,000

4 beds

2 baths

1,851 sq ft

House

120 PANDA WAY, DAVENPORT, FL, 33837

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

Questions? Call us: (888) 625-4885

The Villages®

$449,900

3 beds

2 baths

1,633 sq ft

Villa

5805 CAMDYN CT, THE VILLAGES, FL, 32163

Community: The Villages®

American Village

34 GREEN CIR 101, PALM COAST, FL, 32164, Palm Coast, FL 32164

$185,000

1 beds

1 baths

662 sq ft

Condo

34 GREEN CIR 101, PALM COAST, FL, 32164

Community: American Village

Cindy Certified

17307 BAL HARBOUR DR, WINTER GARDEN, FL,..., Winter Garden, FL 34787

$624,900

3 beds

2 baths

2,123 sq ft

House

17307 BAL HARBOUR DR, WINTER GARDEN, FL,...

Esplanade at McKinnon Groves

11234 SILVER TRUMPET LOOP, WINTER GARDEN..., Winter Garden, FL 34787

$415,000

2 beds

2 baths

1,515 sq ft

Villa

11234 SILVER TRUMPET LOOP, WINTER GARDEN...

Community: Esplanade at McKinnon Groves

Cindy Certified

1799 ALTAVISTA CIR, LAKELAND, FL, 33810, Lakeland, FL 33810

$367,000

3 beds

2 baths

1,753 sq ft

House

1799 ALTAVISTA CIR, LAKELAND, FL, 33810

Trilogy® Orlando

243 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736

$485,000

3 beds

3 baths

2,534 sq ft

House

243 SILVER MAPLE RD, GROVELAND, FL, 3473...

Community: Trilogy® Orlando

Esplanade at McKinnon Groves

11199 SILVER TRUMPET LOOP, WINTER GARDEN..., Winter Garden, FL 34787

$447,118

2 beds

2 baths

1,515 sq ft

Villa

11199 SILVER TRUMPET LOOP, WINTER GARDEN...

Community: Esplanade at McKinnon Groves

Cindy Certified

1005 CHELAN FALLS DR, DELAND, FL, 32724, Deland, FL 32724

$425,000

4 beds

3 baths

1,965 sq ft

House

1005 CHELAN FALLS DR, DELAND, FL, 32724

Esplanade at McKinnon Groves

11202 SILVER TRUMPET LOOP, WINTER GARDEN..., Winter Garden, FL 34787

$437,993

2 beds

2 baths

1,515 sq ft

Villa

11202 SILVER TRUMPET LOOP, WINTER GARDEN...

Community: Esplanade at McKinnon Groves

Plantation Bay Golf & Country Club

426 HARBOUR TOWN LN, ORMOND BEACH, FL, 3..., Ormond Beach, FL 32174

$434,000

3 beds

3 baths

2,316 sq ft

House

426 HARBOUR TOWN LN, ORMOND BEACH, FL, 3...

Community: Plantation Bay Golf & Country Club

Spruce Creek South

10731 SE 174TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491

$299,900

2 beds

2 baths

1,736 sq ft

House

10731 SE 174TH LOOP, SUMMERFIELD, FL, 34...

1313 ZESTY CITRUS LN, MINNEOLA, FL, 3471...

Community: Del Webb Minneola

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

Questions? Call us: (888) 625-4885

Lakeside Landings

5368 COMPASS PT 202, OXFORD, FL, 34484, Oxford, FL 34484

$205,000

2 beds

2 baths

1,402 sq ft

Condo

5368 COMPASS PT 202, OXFORD, FL, 34484

Community: Lakeside Landings

Heritage Hills

3615 SOLANA CIR B, CLERMONT, FL, 34711, Clermont, FL 34711

$249,900

2 beds

2 baths

1,374 sq ft

Villa

3615 SOLANA CIR B, CLERMONT, FL, 34711

Community: Heritage Hills

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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.

Want more information about active adult communities around Winter Park?

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2,698 homes

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Winter Park, FL 55+ active adult communities & homes for sale - Page 26

98 communities near Winter Park

2,698 homes near Winter Park

2 beds

2 baths

1,346 sq ft

House

3 beds

2 baths

1,691 sq ft

House

3 beds

2 baths

1,691 sq ft

House

2 beds

3 baths

2,204 sq ft

House

2 beds

2 baths

1,665 sq ft

House

3 beds

2 baths

1,637 sq ft

House

2 beds

2 baths

1,868 sq ft

House

2 beds

2 baths

1,346 sq ft

House

2 beds

2 baths

1,591 sq ft

House

2 beds

2 baths

1,464 sq ft

Villa

2 beds

4 baths

1,508 sq ft

Manufactured Home

4 beds

2 baths

1,827 sq ft

House

2 beds

2 baths

1,563 sq ft

House

3 beds

2 baths

1,725 sq ft

House

2 beds

2 baths

1,500 sq ft

Condo

4 beds

2 baths

1,851 sq ft

House

3 beds

2 baths

1,633 sq ft

Villa

1 beds

1 baths

662 sq ft

Condo

3 beds

2 baths

2,123 sq ft

House

2 beds