Winter Park, FL 55+ active adult communities & homes for sale - Page 23

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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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 (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

3811 WESTERHAM DR, CLERMONT, FL, 34711

Community: Kings Ridge

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Questions? Call us: (888) 625-4885

The Villages®

1616 BAYHILL DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$249,000

2 beds

2 baths

1,300 sq ft

Manufactured Home

1616 BAYHILL DR, LADY LAKE, FL, 32159

Community: The Villages®

The Villages®

$449,000

3 beds

2 baths

2,179 sq ft

House

1979 REMBERT RD, THE VILLAGES, FL, 32162

Community: The Villages®

The Villages®

$319,000

3 beds

2 baths

1,442 sq ft

Villa

7372 SE 168TH MITZI ST, THE VILLAGES, FL...

Community: The Villages®

Cresswind at Hammock Oaks

948 CLUB CRESSWIND DR, LADY LAKE, FL, 32..., Lady Lake, FL 32159

$645,110

3 beds

3 baths

2,289 sq ft

House

948 CLUB CRESSWIND DR, LADY LAKE, FL, 32...

423 ARMADA LN, DAVENPORT, FL, 33837

Community: Del Webb Orlando

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Questions? Call us: (888) 625-4885

Plantation at Leesburg

4750 SAWGRASS LAKE CIR, LEESBURG, FL, 34..., Leesburg, FL 34748

$399,975

2 beds

2 baths

1,880 sq ft

House

4750 SAWGRASS LAKE CIR, LEESBURG, FL, 34...

Community: Plantation at Leesburg

Lake Ashton

4436 TURNBERRY LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859

$229,900

2 beds

2 baths

1,083 sq ft

House

4436 TURNBERRY LN, LAKE WALES, FL, 33859

Community: Lake Ashton

The Villages®

$620,000

3 beds

2 baths

1,684 sq ft

House

1606 SNELLING AVE, THE VILLAGES, FL, 321...

Community: The Villages®

The Villages®

1033 ALOHA WAY, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$385,000

3 beds

2 baths

1,527 sq ft

House

1033 ALOHA WAY, LADY LAKE, FL, 32159

Community: The Villages®

Plantation at Leesburg

25335 CRANES ROOST CIR, LEESBURG, FL, 34..., Leesburg, FL 34748

$244,900

2 beds

2 baths

1,386 sq ft

House

25335 CRANES ROOST CIR, LEESBURG, FL, 34...

Community: Plantation at Leesburg

Solivita

453 SORRENTO RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$499,900

3 beds

4 baths

2,580 sq ft

House

453 SORRENTO RD, KISSIMMEE, FL, 34759

Community: Solivita

Grand Haven

102 LAGARE ST, PALM COAST, FL, 32137, Palm Coast, FL 32137

$874,995

3 beds

4 baths

2,760 sq ft

House

102 LAGARE ST, PALM COAST, FL, 32137

Community: Grand Haven

Lake James

$414,000

2 beds

2 baths

1,925 sq ft

House

7783 LAKE JAMES BLVD, LAKELAND, FL, 3381...

Community: Lake James

Plantation at Leesburg

5106 CHANTICLEER DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$535,000

3 beds

3 baths

3,112 sq ft

House

5106 CHANTICLEER DR, LEESBURG, FL, 34748

Community: Plantation at Leesburg

The Villages®

$375,000

3 beds

2 baths

1,512 sq ft

House

403 MCLEOD LN, THE VILLAGES, FL, 32162

Community: The Villages®

Twin Lakes

5019 DANCY LN, ST CLOUD, FL, 34772, St Cloud, FL 34772

$589,000

3 beds

3 baths

2,305 sq ft

House

5019 DANCY LN, ST CLOUD, FL, 34772

Community: Twin Lakes

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

Questions? Call us: (888) 625-4885

Latitude Margaritaville

230 SAND BAR LN, DAYTONA BEACH, FL, 3212..., Daytona Beach, FL 32124

$472,500

2 beds

2 baths

1,563 sq ft

Villa

230 SAND BAR LN, DAYTONA BEACH, FL, 3212...

Community: Latitude Margaritaville

Latitude Margaritaville

284 POP TOP LN, DAYTONA BEACH, FL, 32124, Daytona Beach, FL 32124

$357,900

2 beds

2 baths

1,208 sq ft

House

284 POP TOP LN, DAYTONA BEACH, FL, 32124

Community: Latitude Margaritaville

Foxwood Lake Estates

1603 FOXWAY DR, LAKELAND, FL, 33810, Lakeland, FL 33810

$155,000

2 beds

3 baths

1,248 sq ft

Manufactured Home

1603 FOXWAY DR, LAKELAND, FL, 33810

Community: Foxwood Lake Estates

The Villages®

$459,900

3 beds

2 baths

1,918 sq ft

House

1529 STRATON WAY, THE VILLAGES, FL, 3216...

Community: The Villages®

Latitude Margaritaville

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

$490,000

3 beds

2 baths

1,848 sq ft

Villa

466 MARGARITAVILLE AVE, DAYTONA BEACH, F...

Community: Latitude Margaritaville

Latitude Margaritaville

144 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F..., Daytona Beach, FL 32124

$407,500

2 beds

2 baths

1,464 sq ft

House

144 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F...

Community: Latitude Margaritaville

Carillon Lakes

3842 SERENADE LN 1, LAKELAND, FL, 33811, Lakeland, FL 33811

$269,999

2 beds

2 baths

1,722 sq ft

Condo

3842 SERENADE LN 1, LAKELAND, FL, 33811

858 PINCKNEY LN, THE VILLAGES, FL, 32162

Community: The Villages®

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

Questions? Call us: (888) 625-4885

The Villages®

5085 NE 122ND BLVD, OXFORD, FL, 34484, Oxford, FL 34484

$249,900

2 beds

2 baths

1,221 sq ft

House

5085 NE 122ND BLVD, OXFORD, FL, 34484

Community: The Villages®

The Villages®

$359,900

3 beds

2 baths

1,426 sq ft

House

1773 BLACKWELL LN, THE VILLAGES, FL, 321...

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.

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 23

95 communities near Winter Park

2,259 homes near Winter Park

2 beds

2 baths

1,898 sq ft

House

2 beds

1 baths

1,071 sq ft

Villa

2 beds

2 baths

1,160 sq ft

Villa

3 beds

2 baths

1,621 sq ft

House

2 beds

2 baths

1,679 sq ft

House

2 beds

2 baths

1,300 sq ft

Manufactured Home

3 beds

2 baths

2,179 sq ft

House

3 beds

2 baths

1,442 sq ft

Villa

3 beds

3 baths

2,289 sq ft

House

3 beds

3 baths

2,621 sq ft

House

3 beds

2 baths

1,968 sq ft

House

3 beds

2 baths

2,249 sq ft

House

3 beds

3 baths

2,490 sq ft

House

4 beds

4 baths

3,544 sq ft

House

3 beds

2 baths

1,727 sq ft

House

2 beds

2 baths

1,970 sq ft

House

2 beds

2 baths

1,880 sq ft

House

2 beds

2 baths

1,083 sq ft

House

3 beds

2 baths

1,684 sq ft

House

3 beds