Winter Park, FL 55+ active adult communities & homes for sale - Page 3

2,414 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

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

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

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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

Venetian Bay

$300ks - $1Ms

Venetian Bay, New Smyrna Beach, FL

New and Resale | Age-targeted | Built 2004 - present | 1,561 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

5 rating (3 reviews)

Stonecrest

$200ks - $500ks

Stonecrest, Summerfield, FL

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

2.8 rating (6 reviews)

Arlington Ridge

$200ks - $500ks

Arlington Ridge, Leesburg, FL

New and Resale | 55+ age-restricted | Built 2005 - present | 629 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 (3 reviews)

Twin Lakes

$200ks - $600ks

Twin Lakes, St. Cloud, FL

New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes

5 rating (8 reviews)

Royal Highlands

$200ks - $400ks

Royal Highlands, Leesburg, FL

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

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

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Questions? Call us: (888) 625-4885

Pelican Bay Daytona Beach

$100ks - $600ks

Pelican Bay Daytona Beach, Daytona Beach, FL

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

Halifax Plantation

$300ks - $1Ms

Halifax Plantation, Ormond Beach, FL

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

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

$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

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)

Cresswind at Victoria Gar...

$200ks - $500ks

Cresswind at Victoria Gar..., DeLand, FL

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

Summer Trees

$200ks - $400ks

Summer Trees, Port Orange, FL

Resale Only | 55+ age-restricted | Built 1976 - 2005 | 500 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)

Royal Harbor

$200ks - $800ks

Royal Harbor, Tavares, FL

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

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Questions? Call us: (888) 625-4885

5 rating (2 reviews)

Heritage Isle

$300ks - $500ks

Heritage Isle, Viera, FL

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

5 rating (8 reviews)

Pennbrooke Fairways

<$100k - $300ks

Pennbrooke Fairways, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes

Breakaway Trails

$400ks - $800ks

Breakaway Trails, Ormond Beach, FL

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

Four Seasons at Orlando

$300ks - $600ks

Four Seasons at Orlando, Kissimmee, FL

New Construction | 55+ age-restricted | Built 2017 - present | 557 homes

Ridgehaven

$300ks - $600ks

Ridgehaven, Ormond Beach, FL

New Construction | 55+ age-restricted

Scottish Highlands

$100ks - $200ks

Scottish Highlands, Leesburg, FL

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

4.8 rating (6 reviews)

Highland Lakes

$100ks - $200ks

Highland Lakes, Leesburg, FL

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

1 rating (1 reviews)

Sullivan Ranch

$200ks - $500ks

Sullivan Ranch, Mount Dora, FL

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

VillageWalk at Lake Nona

$300ks - $700ks

VillageWalk at Lake Nona, Orlando, FL

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

Foxwood Lake Estates

$100ks - $200ks

Foxwood Lake Estates, Lakeland, FL

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

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

Questions? Call us: (888) 625-4885

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

5 rating (2 reviews)

Bridgewater at Viera

$300ks - $800ks

Bridgewater at Viera, Melbourne, FL

Resale Only | 55+ age-restricted | Built 2017 - 2023 | 870 homes

823 PINEWOOD DR, ORMOND BEACH, FL, 32174

Community: Plantation Bay Golf & Country Club

New Lake Ashton

5288 GREEN DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884

$190,000

3 beds

2 baths

1,847 sq ft

House

5288 GREEN DR, WINTER HAVEN, FL, 33884

Community: Lake Ashton

New Solivita

28 KNOLL WOOD DR, POINCIANA, FL, 34759, Poinciana, FL 34759

$270,000

2 beds

2 baths

1,467 sq ft

House

28 KNOLL WOOD DR, POINCIANA, FL, 34759

Community: Solivita

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Questions? Call us: (888) 625-4885

New Grand Haven

90 W WATERSIDE PKWY, PALM COAST, FL, 321..., Palm Coast, FL 32137

$369,900

2 beds

2 baths

1,628 sq ft

House

90 W WATERSIDE PKWY, PALM COAST, FL, 321...

Community: Grand Haven

New Solivita

118 VISTA DR, POINCIANA, FL, 34759, Poinciana, FL 34759

$368,000

2 beds

2 baths

2,170 sq ft

House

118 VISTA DR, POINCIANA, FL, 34759

Community: Solivita

New The Villages®

2589 ALCADE PL, THE VILLAGES, FL, 32163, The Villages, FL 32163

$278,000

3 beds

2 baths

1,357 sq ft

House

2589 ALCADE PL, THE VILLAGES, FL, 32163

Community: The Villages®

New Solivita

165 LARGO DR, POINCIANA, FL, 34759, Poinciana, FL 34759

$475,000

3 beds

3 baths

2,449 sq ft

House

165 LARGO DR, POINCIANA, FL, 34759

Community: Solivita

New Latitude Margaritaville

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

$799,000

2 beds

3 baths

2,160 sq ft

House

768 MARGARITAVILLE AVE, DAYTONA BEACH, F...

Community: Latitude Margaritaville

New Kings Ridge

4084 CAPLAND AVE, CLERMONT, FL, 34711, Clermont, FL 34711

$325,000

2 beds

2 baths

1,572 sq ft

House

4084 CAPLAND AVE, CLERMONT, FL, 34711

Community: Kings Ridge

New Four Seasons at Orlando

1981 FLORA PASS PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747

$685,000

3 beds

2 baths

2,130 sq ft

House

1981 FLORA PASS PL, KISSIMMEE, FL, 34747

Community: Four Seasons at Orlando

New The Villages®

16856 SE 96TH CHAPELWOOD CIR, THE VILLAG..., The Villages, FL 32162

$300,000

3 beds

2 baths

1,527 sq ft

House

16856 SE 96TH CHAPELWOOD CIR, THE VILLAG...

Community: The Villages®

New Trilogy® Orlando

187 BALMY COAST RD, GROVELAND, FL, 34736, Groveland, FL 34736

$465,000

2 beds

2 baths

2,296 sq ft

House

187 BALMY COAST RD, GROVELAND, FL, 34736

Community: Trilogy® Orlando

New Plantation at Leesburg

3600 MOUNT HOPE LOOP, LEESBURG, FL, 3474..., Leesburg, FL 34748

$305,000

2 beds

2 baths

1,868 sq ft

House

3600 MOUNT HOPE LOOP, LEESBURG, FL, 3474...

Community: Plantation at Leesburg

New The Villages®

2007 RIOS CT, THE VILLAGES, FL, 32159, The Villages, FL 32159

$284,000

2 beds

2 baths

1,139 sq ft

Villa

2007 RIOS CT, THE VILLAGES, FL, 32159

House

17115 SE 93RD TELLFIER TER, THE VILLAGES...

1432 KINNARD CIR, ORMOND BEACH, FL, 3217...

Community: Halifax Plantation

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

Questions? Call us: (888) 625-4885

Cresswind DeLand

1291 SAVOY LN, DELAND, FL, 32724, Deland, FL 32724

$524,990

3 beds

3 baths

2,289 sq ft

House

1291 SAVOY LN, DELAND, FL, 32724

Community: Cresswind DeLand

Royal Harbor

3370 SAINT LUCIA CT, TAVARES, FL, 32778, Tavares, FL 32778

$352,900

3 beds

2 baths

1,893 sq ft

House

3370 SAINT LUCIA CT, TAVARES, FL, 32778

Community: Royal Harbor

Foxwood Lake Estates

1629 TALLY HO DR, LAKELAND, FL, 33810, Lakeland, FL 33810

$187,000

2 beds

2 baths

1,482 sq ft

Manufactured Home

1629 TALLY HO DR, LAKELAND, FL, 33810

Community: Foxwood Lake Estates

Carlsberg Estates on Lake Suzanne

241 LOURDES ST, LAKE WALES, FL, 33859, Lake Wales, FL 33859

$297,000

2 beds

2 baths

1,251 sq ft

House

241 LOURDES ST, LAKE WALES, FL, 33859

Community: Carlsberg Estates on Lake Suzanne

Venetian Bay

424 LUNA BELLA LN 415, NEW SMYRNA BEACH,..., New Smyrna Beach, FL 32168

$319,900

2 beds

2 baths

1,492 sq ft

Condo

424 LUNA BELLA LN 415, NEW SMYRNA BEACH,...

Community: Venetian Bay

The Villages®

$310,000

2 beds

2 baths

1,116 sq ft

Villa

872 WINCHESTER CT, THE VILLAGES, FL, 321...

Community: The Villages®

The Villages®

$260,000

2 beds

2 baths

1,190 sq ft

Villa

16848 SE 94TH SUNNYBROOK CIR, THE VILLAG...

Community: The Villages®

Pelican Bay Daytona Beach

100 BLACK CROW CIR 4000, DAYTONA BEACH, ..., Daytona Beach, FL 32119

$294,900

3 beds

3 baths

1,869 sq ft

Condo

100 BLACK CROW CIR 4000, DAYTONA BEACH, ...

Community: Pelican Bay Daytona Beach

Stonecrest

11086 SE 175TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$259,900

2 beds

2 baths

1,348 sq ft

House

11086 SE 175TH PL, SUMMERFIELD, FL, 3449...

Community: Stonecrest

Latitude Margaritaville

616 BEACH BUM BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124

$724,900

3 beds

3 baths

2,083 sq ft

House

616 BEACH BUM BLVD, DAYTONA BEACH, FL, 3...

Community: Latitude Margaritaville

Sandpiper Golf & Country Club

5817 SWALLOW DR, LAKELAND, FL, 33809, Lakeland, FL 33809

$365,000

3 beds

2 baths

1,957 sq ft

House

5817 SWALLOW DR, LAKELAND, FL, 33809

Community: Sandpiper Golf & Country Club

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

Questions? Call us: (888) 625-4885

The Villages®

$239,000

1 beds

1 baths

828 sq ft

Villa

5597 GRACIE LN, THE VILLAGES, FL, 32163

Community: The Villages®

VillageWalk at Lake Nona

11830 ISELLE DR, ORLANDO, FL, 32827, Orlando, FL 32827

$450,000

2 beds

2 baths

1,512 sq ft

Halfplex

11830 ISELLE DR, ORLANDO, FL, 32827

Community: VillageWalk at Lake Nona

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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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2,414 homes

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Winter Park, FL 55+ active adult communities & homes for sale - Page 3

93 communities near Winter Park

2,414 homes near Winter Park

3 beds

2 baths

1,489 sq ft

House

3 beds

2 baths

1,392 sq ft

House

2 beds

2 baths

1,526 sq ft

Townhouse

3 beds

2 baths

1,847 sq ft

House

2 beds

2 baths

1,467 sq ft

House

2 beds

2 baths

1,628 sq ft

House

2 beds

2 baths

2,170 sq ft

House

3 beds

2 baths

1,357 sq ft

House

3 beds

3 baths

2,449 sq ft

House

2 beds

3 baths

2,160 sq ft

House

2 beds

2 baths

1,572 sq ft

House

3 beds

2 baths

2,130 sq ft

House

3 beds

2 baths

1,527 sq ft

House

2 beds

2 baths

2,296 sq ft

House

2 beds

2 baths

1,868 sq ft

House

2 beds

2 baths

1,139 sq ft

Villa

3 beds

2 baths

1,416 sq ft

House

3 beds

2 baths

1,862 sq ft

House

3 beds

2 baths

2,411 sq ft

House

3 beds