Winter Park, FL 55+ active adult communities & homes for sale - Page 2

97 communities near Winter Park

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Esplanade at Westview

$300ks - $700ks

Esplanade at Westview, Kissimmee, FL

New Construction | Age-targeted | Built 2025 - present | 600 homes

Four Seasons at Orlando

$300ks - $600ks

Four Seasons at Orlando, Kissimmee, FL

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

5 rating (2 reviews)

Heritage Isle

$300ks - $500ks

Heritage Isle, Viera, FL

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

Ridgehaven

$300ks - $600ks

Ridgehaven, Ormond Beach, FL

New Construction | 55+ age-restricted

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Highland Fairways

$100ks - $300ks

Highland Fairways, Lakeland, FL

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

Tohoqua Reserve

$300ks - $600ks

Tohoqua Reserve, Kissimmee, FL

New Construction | 55+ age-restricted | Built 2021 - present | 258 homes

Cresswind at Lake Harris

$300ks - $500ks

Cresswind at Lake Harris, Tavares, FL

New Construction | 55+ age-restricted | Built 2025 - present | 625 homes

3.8 rating (5 reviews)

Traditions at Lake Ruby

$200ks - $300ks

Traditions at Lake Ruby, Winter Haven, FL

Resale Only | 55+ age-restricted | Built 2005 - 2020 | 552 homes

Colonnades

$100ks - $200ks

Colonnades, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1985 - 1994 | 360 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.

Del Webb at Viera

$400ks - $1Ms

Del Webb at Viera, Melbourne, FL

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

4 rating (4 reviews)

High Vista at Ridgewood L...

$200ks - $300ks

High Vista at Ridgewood L..., Davenport, FL

Resale Only | 55+ age-restricted | Built 1995 - 2005 | 623 homes

4.2 rating (10 reviews)

Indian River Colony Club

$200ks - $400ks

Indian River Colony Club, Melbourne, FL

New and Resale | 55+ age-restricted | Built 1986 - present | 777 homes

The Reserve at Victoria

$400ks - $800ks

The Reserve at Victoria, DeLand, FL

New Construction | Age-targeted | Built 2022 - 2025 | 408 homes

Del Webb Lakehaven

$400ks - $800ks

Del Webb Lakehaven, Clermont, FL

New Construction | 55+ age-restricted | Built 2026 - present

Westhaven at Ovation - To...

$400ks - $500ks

Westhaven at Ovation - To..., Winter Garden, FL

New Construction | Age-targeted | Built 2025 - present

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Questions? Call us: (888) 625-4885

3.9 rating (7 reviews)

Summit Greens

$300ks - $400ks

Summit Greens, Clermont, FL

Resale Only | 55+ age-restricted | Built 2001 - 2019 | 769 homes

5 rating (1 reviews)

Esplanade at Highland Ran...

$300ks - $600ks

Esplanade at Highland Ran..., Clermont, FL

Resale Only | 55+ age-restricted | Built 2014 - 2022 | 475 homes

Lakeside Landings

$100ks - $300ks

Lakeside Landings, Oxford, FL

New and Resale | Age-targeted | Built 2005 - present | 700 homes

Huntington at Hunter's Ri...

$300ks

Huntington at Hunter's Ri..., Ormond Beach, FL

New Construction | 55+ age-restricted | Built 2015 - present | 326 homes

Lake James

$300ks

Lake James, Lakeland, FL

New and Resale | 55+ age-restricted | Built 2004 - present | 216 homes

5 rating (2 reviews)

American Village

$300ks

American Village, Palm Coast, FL

New Construction | 55+ age-restricted | Built 2018 - present | 141 homes

Del Webb Minneola

$400ks - $700ks

Del Webb Minneola, Minneola, FL

New Construction | 55+ age-restricted | Built 2020 - present

Lakes at Laurel Highlands

$200ks - $300ks

Lakes at Laurel Highlands, Lakeland, FL

New Construction | Age-targeted | Built 2017 - present | 65 homes

Summit Chase Villas

$100ks

Summit Chase Villas, Tavares, FL

Resale Only | 55+ age-restricted | Built 1982 - 1989 | 60 homes

Cresswind DeLand

$300ks - $500ks

Cresswind DeLand, DeLand, FL

New Construction | 55+ age-restricted | Built 2023 - present | 600 homes

5 rating (1 reviews)

Del Webb Oasis

$400ks - $700ks

Del Webb Oasis, Winter Garden, FL

New Construction | 55+ age-restricted | Built 2020 - present | 422 homes

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Carmel Condominium

$100ks

Carmel Condominium, Rockledge, FL

Resale Only | 55+ age-restricted | Built 1996 - 1996 | 60 homes

Lake Henry Estates

$100ks - $300ks

Lake Henry Estates, Haines City, FL

Resale Only | 55+ age-restricted | Built 1992 - 2004 | 280 homes

Vienna Square

$100ks - $200ks

Vienna Square, Winter Haven, FL

New and Resale | 55+ age-restricted | Built 2007 - present | 181 homes

5 rating (2 reviews)

Palms at Serenoa

$200ks - $400ks

Palms at Serenoa, Clermont, FL

New Construction | 55+ age-restricted | Built 2018 - present | 570 homes

The Savannahs

$400ks - $500ks

The Savannahs, West Melbourne, FL

Resale Only | 55+ age-restricted | Built 2017 - 2020 | 125 homes

Cresswind at Hammock Oaks

$300ks - $500ks

Cresswind at Hammock Oaks, Lady Lake, FL

New and Resale | 55+ age-restricted | Built 2024 - 2025 | 141 homes

5 rating (1 reviews)

Park Place

$200ks - $400ks

Park Place, Palm Coast, FL

Resale Only | 55+ age-restricted | Built 2015 - present | 123 homes

Alhambra Villas Condomini...

$100ks - $200ks

Alhambra Villas Condomini..., DeLand, FL

Resale Only | 55+ age-restricted | Built 1970 - 1972 | 60 homes

5 rating (1 reviews)

Silver Lakes

$100ks - $300ks

Silver Lakes, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1996 - 2001 | 148 homes

Fountain View

$300ks - $400ks

Fountain View, Ormond Beach, FL

New Construction | 55+ age-restricted | Built 2023 - present | 100 homes

5 rating (4 reviews)

Carillon Lakes

$200ks - $400ks

Carillon Lakes, Lakeland, FL

Resale Only | Age-targeted | Built 2000 - 2006 | 650 homes

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Questions? Call us: (888) 625-4885

Compass Pointe

$200ks - $300ks

Compass Pointe, West Melbourne, FL

Resale Only | 55+ age-restricted | Built 1999 - 2004 | 155 homes

Spring Lake Towers

$100ks

Spring Lake Towers, Winter Haven, FL

Resale Only | 55+ age-restricted | Built 1970 - 1970 | 79 homes

728 TRUMAN AVE, LADY LAKE, FL, 32159

Community: The Villages®

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

Questions? Call us: (888) 625-4885

Solivita

373 VESTRELLA DR, POINCIANA, FL, 34759, Poinciana, FL 34759

$349,900

2 beds

2 baths

1,658 sq ft

House

373 VESTRELLA DR, POINCIANA, FL, 34759

Community: Solivita

Twin Lakes

2777 SOUTHLAND ST, ST CLOUD, FL, 34772, St Cloud, FL 34772

$550,000

3 beds

3 baths

2,365 sq ft

House

2777 SOUTHLAND ST, ST CLOUD, FL, 34772

Community: Twin Lakes

The Villages®

$359,900

2 beds

2 baths

1,146 sq ft

Villa

1214 SAN BERNARDO RD, THE VILLAGES, FL, ...

Community: The Villages®

The Villages®

4946 NE 124TH RD, OXFORD, FL, 34484, Oxford, FL 34484

$425,000

3 beds

3 baths

2,547 sq ft

House

4946 NE 124TH RD, OXFORD, FL, 34484

Community: The Villages®

The Villages®

$334,900

3 beds

2 baths

1,440 sq ft

Villa

4295 FREDDA TER, THE VILLAGES, FL, 32163

Community: The Villages®

Breakaway Trails

1 CROOKED BRIDGE WAY, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174

$775,000

5 beds

3 baths

3,193 sq ft

House

1 CROOKED BRIDGE WAY, ORMOND BEACH, FL, ...

Community: Breakaway Trails

Del Webb Sunbridge

2743 RIVER CREEK LN, ST CLOUD, FL, 34771, St Cloud, FL 34771

$679,900

3 beds

3 baths

2,321 sq ft

House

2743 RIVER CREEK LN, ST CLOUD, FL, 34771

Community: Del Webb Sunbridge

The Villages®

$269,900

2 beds

2 baths

1,188 sq ft

Villa

1806 QUEENSBURY TER, THE VILLAGES, FL, 3...

Community: The Villages®

The Villages®

$299,900

2 beds

2 baths

1,148 sq ft

House

17654 SE 93RD BUTLER CT, THE VILLAGES, F...

Community: The Villages®

Arlington Ridge

26669 OTTER CREEK LN, LEESBURG, FL, 3474..., Leesburg, FL 34748

$350,000

3 beds

2 baths

1,718 sq ft

House

26669 OTTER CREEK LN, LEESBURG, FL, 3474...

Community: Arlington Ridge

Spruce Creek Country Club

13732 SE 88TH CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491

$229,900

2 beds

2 baths

1,136 sq ft

House

13732 SE 88TH CT, SUMMERFIELD, FL, 34491

Community: Spruce Creek Country Club

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

Questions? Call us: (888) 625-4885

Stonecrest

12271 SE 175TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$396,000

4 beds

3 baths

2,246 sq ft

House

12271 SE 175TH LN, SUMMERFIELD, FL, 3449...

Community: Stonecrest

Trilogy® Orlando

615 CONSERVATION BLVD, GROVELAND, FL, 34..., Groveland, FL 34736

$349,900

2 beds

3 baths

2,009 sq ft

House

615 CONSERVATION BLVD, GROVELAND, FL, 34...

Community: Trilogy® Orlando

Spruce Creek Country Club

9082 SE 120TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491

$275,000

2 beds

2 baths

1,346 sq ft

House

9082 SE 120TH LOOP, SUMMERFIELD, FL, 344...

Community: Spruce Creek Country Club

The Villages®

$339,900

2 beds

2 baths

1,152 sq ft

Villa

1666 SUMMERCHASE LOOP, THE VILLAGES, FL,...

Community: The Villages®

Latitude Margaritaville

224 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124

$357,900

2 beds

2 baths

1,308 sq ft

House

224 GYPSY PALACE LN, DAYTONA BEACH, FL, ...

280 INDIAN WELLS AVE, KISSIMMEE, FL, 347...

Community: Solivita

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

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Spruce Creek Country Club

9512 SE 124TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491

$399,900

2 beds

3 baths

2,475 sq ft

House

9512 SE 124TH LOOP, SUMMERFIELD, FL, 344...

Community: Spruce Creek Country Club

Latitude Margaritaville

373 HANG LOOSE WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124

$399,900

2 beds

2 baths

1,466 sq ft

House

373 HANG LOOSE WAY, DAYTONA BEACH, FL, 3...

Community: Latitude Margaritaville

The Villages®

$1,042,000

3 beds

2 baths

2,627 sq ft

House

5845 STORMS AVE, THE VILLAGES, FL, 32163

Community: The Villages®

The Villages®

$429,900

3 beds

2 baths

1,715 sq ft

House

1462 PELICAN PATH, THE VILLAGES, FL, 321...

Community: The Villages®

Latitude Margaritaville

198 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124

$376,495

2 beds

2 baths

1,464 sq ft

House

198 GYPSY PALACE LN, DAYTONA BEACH, FL, ...

Community: Latitude Margaritaville

Carlsberg Estates on Lake Suzanne

364 LAKE SUZANNE DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859

$284,900

2 beds

2 baths

1,387 sq ft

House

364 LAKE SUZANNE DR, LAKE WALES, FL, 338...

Community: Carlsberg Estates on Lake Suzanne

Lakes of Mount Dora

8923 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757

$384,900

3 beds

2 baths

1,926 sq ft

House

8923 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...

Community: Lakes of Mount Dora

New The Villages®

12439 NE 48TH CIR, OXFORD, FL, 34484, Oxford, FL 34484

$355,000

4 beds

3 baths

2,224 sq ft

House

12439 NE 48TH CIR, OXFORD, FL, 34484

Community: The Villages®

New Breakaway Trails

73 SHADOW CREEK WAY, ORMOND BEACH, FL, 3..., Ormond Beach, FL 32174

$1,250,000

5 beds

6 baths

4,628 sq ft

House

73 SHADOW CREEK WAY, ORMOND BEACH, FL, 3...

Community: Breakaway Trails

New Stonecrest

10949 SE 169TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$325,000

3 beds

2 baths

1,366 sq ft

House

10949 SE 169TH LN, SUMMERFIELD, FL, 3449...

Community: Stonecrest

New Pelican Bay Daytona Beach

149 BLUE HERON DR D, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119

$183,900

2 beds

2 baths

1,192 sq ft

Condo

149 BLUE HERON DR D, DAYTONA BEACH, FL, ...

Community: Pelican Bay Daytona Beach

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

Questions? Call us: (888) 625-4885

New Pennbrooke Fairways

909 EAGLES LNDG, LEESBURG, FL, 34748, Leesburg, FL 34748

$229,900

2 beds

2 baths

1,212 sq ft

House

909 EAGLES LNDG, LEESBURG, FL, 34748

Community: Pennbrooke Fairways

New Twin Lakes

5167 GARDENROW DR, ST CLOUD, FL, 34772, St Cloud, FL 34772

$348,440

2 beds

2 baths

1,322 sq ft

Villa

5167 GARDENROW DR, ST CLOUD, FL, 34772

Community: Twin Lakes

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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97 communities

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Winter Park, FL 55+ active adult communities & homes for sale - Page 2

97 communities near Winter Park

2,229 homes near Winter Park

3 beds

2 baths

1,392 sq ft

House

3 beds

3 baths

1,827 sq ft

House

2 beds

2 baths

1,344 sq ft

House

2 beds

2 baths

1,160 sq ft

House

2 beds

2 baths

1,056 sq ft

Manufactured Home

2 beds

2 baths

1,658 sq ft

House

3 beds

3 baths

2,365 sq ft

House

2 beds

2 baths

1,146 sq ft

Villa

3 beds

3 baths

2,547 sq ft

House

3 beds

2 baths

1,440 sq ft

Villa

5 beds

3 baths

3,193 sq ft

House

3 beds

3 baths

2,321 sq ft

House

2 beds

2 baths

1,188 sq ft

Villa

2 beds

2 baths

1,148 sq ft

House

3 beds

2 baths

1,718 sq ft

House

2 beds

2 baths

1,136 sq ft

House

4 beds

3 baths

2,246 sq ft

House

2 beds

3 baths

2,009 sq ft

House

2 beds

2 baths

1,346 sq ft

House

2 beds