Winter Park, FL 55+ active adult communities & homes for sale - Page 17

2,259 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

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

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

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 (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)

Stonecrest

$200ks - $500ks

Stonecrest, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 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

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.

Halifax Plantation

$300ks - $1Ms

Halifax Plantation, Ormond Beach, FL

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

5 rating (8 reviews)

Royal Highlands

$200ks - $400ks

Royal Highlands, Leesburg, FL

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

Pelican Bay Daytona Beach

$100ks - $600ks

Pelican Bay Daytona Beach, Daytona Beach, FL

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

3.8 rating (6 reviews)

Trilogy® Orlando

$200ks - $500ks

Trilogy® Orlando, Groveland, FL

Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 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

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Questions? Call us: (888) 625-4885

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

5 rating (7 reviews)

Kings Ridge

$200ks - $400ks

Kings Ridge, Clermont, FL

Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 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 (1 reviews)

Cresswind at Victoria Gar...

$200ks - $500ks

Cresswind at Victoria Gar..., DeLand, FL

Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 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

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

Breakaway Trails

$400ks - $800ks

Breakaway Trails, Ormond Beach, FL

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

5 rating (1 reviews)

Royal Harbor

$200ks - $800ks

Royal Harbor, Tavares, FL

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

1 rating (1 reviews)

Sullivan Ranch

$200ks - $500ks

Sullivan Ranch, Mount Dora, FL

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

4.8 rating (6 reviews)

Highland Lakes

$100ks - $200ks

Highland Lakes, Leesburg, FL

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

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Questions? Call us: (888) 625-4885

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

Summer Trees

$200ks - $400ks

Summer Trees, Port Orange, FL

Resale Only | 55+ age-restricted | Built 1976 - 2005 | 500 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 Lakes at Harmony

$200ks - $400ks

The Lakes at Harmony, Harmony, FL

New and Resale | 55+ age-restricted | Built 2016 - present | 400 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

The Country Club of Mount...

$200ks - $1Ms

The Country Club of Mount..., Mount Dora, FL

Resale Only | Age-targeted | Built 1991 - 2005 | 827 homes

Foxwood Lake Estates

$100ks - $200ks

Foxwood Lake Estates, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1982 - 1987 | 545 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

Gatherings of Lake Nona

$300ks - $400ks

Gatherings of Lake Nona, Orlando, FL

New and Resale | 55+ age-restricted | Built 2017 - present | 216 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

The Timbers at Everlands

$200ks - $500ks

The Timbers at Everlands, Palm Bay, FL

New Construction | 55+ age-restricted | Built 2023 - present | 450 homes

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

Questions? Call us: (888) 625-4885

5 rating (1 reviews)

VillageWalk at Lake Nona

$300ks - $700ks

VillageWalk at Lake Nona, Orlando, FL

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

Scottish Highlands

$100ks - $200ks

Scottish Highlands, Leesburg, FL

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

1575 HOLLYBERRY PL, THE VILLAGES, FL, 32...

Community: The Villages®

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Questions? Call us: (888) 625-4885

Legacy of Leesburg

5351 AURORA DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$379,900

4 beds

4 baths

3,125 sq ft

House

5351 AURORA DR, LEESBURG, FL, 34748

Community: Legacy of Leesburg

Highland Lakes

26010 NEWCOMBE CIR, LEESBURG, FL, 34748, Leesburg, FL 34748

$309,000

3 beds

2 baths

1,903 sq ft

House

26010 NEWCOMBE CIR, LEESBURG, FL, 34748

Community: Highland Lakes

Spruce Creek Country Club

12716 SE 91ST TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491

$424,900

3 beds

2 baths

2,128 sq ft

House

12716 SE 91ST TERRACE RD, SUMMERFIELD, F...

Community: Spruce Creek Country Club

Venetian Bay

3421 GALLIA ST, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168

$374,900

3 beds

3 baths

2,090 sq ft

Townhouse

3421 GALLIA ST, NEW SMYRNA BEACH, FL, 32...

57 OSPREY CIR, PALM COAST, FL, 32137

2264 MARGARITA DR, THE VILLAGES, FL, 321...

Community: The Villages®

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Questions? Call us: (888) 625-4885

Spruce Creek South

17587 SE 106TH AVE, SUMMERFIELD, FL, 344..., Summerfield, FL 34491

$279,900

2 beds

2 baths

1,546 sq ft

House

17587 SE 106TH AVE, SUMMERFIELD, FL, 344...

Community: Spruce Creek South

Compass Pointe

685 NAPLES CT, MELBOURNE, FL, 32904, Melbourne, FL 32904

$379,900

3 beds

2 baths

1,936 sq ft

House

685 NAPLES CT, MELBOURNE, FL, 32904

Community: Compass Pointe

Latitude Margaritaville

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

$529,000

2 beds

2 baths

1,771 sq ft

House

927 MARGARITAVILLE AVE, DAYTONA BEACH, F...

Community: Latitude Margaritaville

The Villages®

$349,900

3 beds

2 baths

1,390 sq ft

House

3812 INFINITY RUN, THE VILLAGES, FL, 321...

Community: The Villages®

The Villages®

$304,000

2 beds

2 baths

1,520 sq ft

House

3001 SAINT THOMAS LN, THE VILLAGES, FL, ...

Community: The Villages®

Bridgewater at Viera

2881 TREASURE CAY LN, MELBOURNE, FL, 329..., Melbourne, FL 32940

$495,000

2 beds

2 baths

1,908 sq ft

House

2881 TREASURE CAY LN, MELBOURNE, FL, 329...

Community: Bridgewater at Viera

The Villages®

$725,000

3 beds

3 baths

2,551 sq ft

House

1322 AUGUSTINE DR, THE VILLAGES, FL, 321...

Community: The Villages®

Arlington Ridge

27132 ROANOKE DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$445,000

3 beds

2 baths

1,722 sq ft

House

27132 ROANOKE DR, LEESBURG, FL, 34748

Community: Arlington Ridge

Del Webb at Viera

9030 WANDER TRAIL TRL, MELBOURNE, FL, 32..., Melbourne, FL 32940

$849,850

3 beds

3 baths

2,305 sq ft

House

9030 WANDER TRAIL TRL, MELBOURNE, FL, 32...

Community: Del Webb at Viera

The Villages®

101 CYPRESS RD, WILDWOOD, FL, 34785, Wildwood, FL 34785

$128,500

2 beds

2 baths

1,144 sq ft

Manufactured Home

101 CYPRESS RD, WILDWOOD, FL, 34785

Community: The Villages®

Halifax Plantation

3319 NEWBLISS CIR, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174

$313,000

3 beds

2 baths

1,957 sq ft

House

3319 NEWBLISS CIR, ORMOND BEACH, FL, 321...

Community: Halifax Plantation

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

Questions? Call us: (888) 625-4885

Del Webb at Viera

9030 WANDER TRL, MELBOURNE, FL, 32940, Melbourne, FL 32940

$849,850

3 beds

3 baths

2,305 sq ft

House

9030 WANDER TRL, MELBOURNE, FL, 32940

Community: Del Webb at Viera

Venetian Bay

3515 ROMEA CIR, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168

$320,000

3 beds

3 baths

1,794 sq ft

Townhouse

3515 ROMEA CIR, NEW SMYRNA BEACH, FL, 32...

Community: Venetian Bay

Kings Ridge

3605 WESTERHAM DR, CLERMONT, FL, 34711, Clermont, FL 34711

$334,995

3 beds

2 baths

1,572 sq ft

House

3605 WESTERHAM DR, CLERMONT, FL, 34711

Community: Kings Ridge

Westhaven at Ovation - Townes Collection

12792 SUNSET WALK DR, WINTER GARDEN, FL,..., Winter Garden, FL 34787

$527,000

4 beds

3 baths

1,930 sq ft

Townhouse

12792 SUNSET WALK DR, WINTER GARDEN, FL,...

Community: Westhaven at Ovation - Townes Collection

The Villages®

$348,000

3 beds

2 baths

1,559 sq ft

House

3323 ABANA PATH, THE VILLAGES, FL, 32163

Community: The Villages®

The Villages®

$379,000

2 beds

2 baths

1,327 sq ft

Villa

587 AUDREY LN, THE VILLAGES, FL, 32162

Community: The Villages®

Del Webb Orlando

212 GRANADA LN, DAVENPORT, FL, 33837, Davenport, FL 33837

$413,900

3 beds

2 baths

1,568 sq ft

House

212 GRANADA LN, DAVENPORT, FL, 33837

Community: Del Webb Orlando

Alhambra Villas Condominiums

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

$190,000

2 beds

2 baths

1,091 sq ft

Condo

239 N HILL AVE 110, DELAND, FL, 32724

Community: Alhambra Villas Condominiums

The Villages®

$285,000

2 beds

2 baths

1,388 sq ft

House

2718 BENAVIDES DR, THE VILLAGES, FL, 321...

Community: The Villages®

Harbor Hills Country Club

6042 TOPSAIL RD, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$369,900

3 beds

2 baths

2,190 sq ft

Halfplex

6042 TOPSAIL RD, LADY LAKE, FL, 32159

Community: Harbor Hills Country Club

Stonecrest

12115 SE 176TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491

$289,000

3 beds

2 baths

1,472 sq ft

House

12115 SE 176TH LOOP, SUMMERFIELD, FL, 34...

Community: Stonecrest

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

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Plantation Bay Golf & Country Club

50 TREETOP CIR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$549,900

3 beds

4 baths

3,014 sq ft

House

50 TREETOP CIR, ORMOND BEACH, FL, 32174

Community: Plantation Bay Golf & Country Club

Trilogy® Orlando

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

$399,900

2 beds

2 baths

1,848 sq ft

House

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

Community: Trilogy® Orlando

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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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2,259 homes

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Winter Park, FL 55+ active adult communities & homes for sale - Page 17

95 communities near Winter Park

2,259 homes near Winter Park

2 beds

2 baths

1,148 sq ft

House

3 beds

2 baths

1,397 sq ft

Villa

3 beds

2 baths

1,392 sq ft

House

2 beds

2 baths

1,187 sq ft

Villa

3 beds

2 baths

1,392 sq ft

House

4 beds

4 baths

3,125 sq ft

House

3 beds

2 baths

1,903 sq ft

House

3 beds

2 baths

2,128 sq ft

House

3 beds

3 baths

2,090 sq ft

Townhouse

2 beds

2 baths

1,308 sq ft

House

3 beds

3 baths

1,995 sq ft

House

2 beds

2 baths

1,380 sq ft

House

3 beds

3 baths

3,093 sq ft

House

2 beds

2 baths

1,565 sq ft

House

2 beds

2 baths

1,156 sq ft

Condo

3 beds

2 baths

1,609 sq ft

House

2 beds

2 baths

1,546 sq ft

House

3 beds

2 baths

1,936 sq ft

House

2 beds

2 baths

1,771 sq ft

House

3 beds