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

98 communities near Winter Park

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The Reserve at Victoria

$400ks - $800ks

The Reserve at Victoria, DeLand, FL

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

Colonnades

$100ks - $200ks

Colonnades, Lakeland, FL

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

The Lakes at Harmony

$200ks - $400ks

The Lakes at Harmony, Harmony, FL

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

Scottish Highlands

$100ks - $200ks

Scottish Highlands, Leesburg, FL

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

Four Seasons at Orlando

$300ks - $600ks

Four Seasons at Orlando, Kissimmee, FL

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

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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

Esplanade at Westview

$300ks - $700ks

Esplanade at Westview, Kissimmee, FL

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

Summer Trees

$200ks - $400ks

Summer Trees, Port Orange, FL

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

Westhaven at Ovation - To...

$400ks - $500ks

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

New Construction | Age-targeted | Built 2025 - present

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 Minneola

$400ks - $700ks

Del Webb Minneola, Minneola, FL

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

5 rating (2 reviews)

Palms at Serenoa

$200ks - $400ks

Palms at Serenoa, Clermont, FL

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

Ridgehaven

$300ks - $600ks

Ridgehaven, Ormond Beach, FL

New Construction | 55+ age-restricted

Esplanade at McKinnon Gro...

$300ks - $900ks

Esplanade at McKinnon Gro..., Winter Garden, FL

New Construction | Age-targeted | Built 2024 - present | 658 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

Tohoqua Reserve

$300ks - $600ks

Tohoqua Reserve, Kissimmee, FL

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

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Huntington at Hunter's Ri...

$300ks

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

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

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

Vienna Square

$100ks - $200ks

Vienna Square, Winter Haven, FL

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

3.9 rating (7 reviews)

Summit Greens

$300ks - $400ks

Summit Greens, Clermont, FL

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

Cresswind at Lake Harris

$300ks - $500ks

Cresswind at Lake Harris, Tavares, FL

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

Lake Henry Estates

$100ks - $300ks

Lake Henry Estates, Haines City, FL

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

5 rating (2 reviews)

American Village

$100ks - $300ks

American Village, Palm Coast, FL

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

Cresswind DeLand

$300ks - $500ks

Cresswind DeLand, DeLand, FL

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

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4 rating (3 reviews)

Heritage Isle

$300ks - $500ks

Heritage Isle, Viera, FL

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

Del Webb Lakehaven

$400ks - $800ks

Del Webb Lakehaven, Clermont, FL

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

Alamanda Key

$300ks - $500ks

Alamanda Key, Melbourne, FL

Resale Only | 55+ age-restricted | Built 2005 - 2021 | 300 homes

Alhambra Villas Condomini...

$100ks - $200ks

Alhambra Villas Condomini..., DeLand, FL

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

Lake James

$300ks

Lake James, Lakeland, FL

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

5 rating (4 reviews)

Carillon Lakes

$200ks - $400ks

Carillon Lakes, Lakeland, FL

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

Carmel Condominium

$100ks

Carmel Condominium, Rockledge, FL

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

Summit Chase Villas

$100ks

Summit Chase Villas, Tavares, FL

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

5 rating (1 reviews)

Silver Lakes

$100ks - $300ks

Silver Lakes, Lakeland, FL

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

5 rating (1 reviews)

Park Place

$200ks - $400ks

Park Place, Palm Coast, FL

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

Lakes at Laurel Highlands

$200ks - $300ks

Lakes at Laurel Highlands, Lakeland, FL

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

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Questions? Call us: (888) 625-4885

The Savannahs

$400ks - $500ks

The Savannahs, West Melbourne, FL

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

Spring Lake Towers

$100ks

Spring Lake Towers, Winter Haven, FL

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

615 JUNIPER WAY, TAVARES, FL, 32778

Community: Baytree

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The Villages®

$299,900

3 beds

2 baths

1,392 sq ft

House

17648 SE 93RD BUTLER CT, THE VILLAGES, F...

Community: The Villages®

The Villages®

$279,900

2 beds

2 baths

1,344 sq ft

House

1707 GOMEZ PL, THE VILLAGES, FL, 32162

Community: The Villages®

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

$405,000

3 beds

3 baths

2,547 sq ft

House

4946 NE 124TH RD, OXFORD, FL, 34484

Community: The Villages®

Breakaway Trails

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

$765,000

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

$648,500

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®

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

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...

Villa

2015 PEACEFUL PL, THE VILLAGES, FL, 3216...

Community: The Villages®

New Pelican Bay Daytona Beach

101 BOB WHITE CT 101J, DAYTONA BEACH, FL..., Daytona Beach, FL 32119

$179,000

2 beds

2 baths

1,165 sq ft

House

101 BOB WHITE CT 101J, 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 Grand Haven

7 RIVER LANDING DR, PALM COAST, FL, 3213..., Palm Coast, FL 32137

$439,000

2 beds

3 baths

1,919 sq ft

Townhouse

7 RIVER LANDING DR, PALM COAST, FL, 3213...

Community: Grand Haven

New The Villages®

17198 SE 84TH KNIGHT AVE, THE VILLAGES, ..., The Villages, FL 32162

$415,000

3 beds

2 baths

1,568 sq ft

Villa

17198 SE 84TH KNIGHT AVE, THE VILLAGES, ...

Community: The Villages®

New The Villages®

4236 YARDHAM TER, THE VILLAGES, FL, 3216..., The Villages, FL 32163

$599,000

3 beds

2 baths

2,400 sq ft

House

4236 YARDHAM TER, THE VILLAGES, FL, 3216...

Community: The Villages®

New Grand Haven

38 FRONT ST, PALM COAST, FL, 32137, Palm Coast, FL 32137

$699,500

5 beds

4 baths

2,600 sq ft

House

38 FRONT ST, PALM COAST, FL, 32137

Community: Grand Haven

New The Villages®

644 ELLSWORTH WAY, LADY LAKE, FL, 32162, Lady Lake, FL 32162

$250,000

2 beds

2 baths

1,148 sq ft

House

644 ELLSWORTH WAY, LADY LAKE, FL, 32162

Community: The Villages®

New The Villages®

2018 CASTANO PL, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$280,000

2 beds

2 baths

1,213 sq ft

House

2018 CASTANO PL, LADY LAKE, FL, 32159

Community: The Villages®

New

Cindy Certified

3008 RIBBON GRASS DR, MELBOURNE, FL, 329..., Melbourne, FL 32940

$550,000

2 baths

1,670 sq ft

House

6401 WHITE WILLOW CT, ST CLOUD, FL, 3477...

Community: Del Webb Sunbridge

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

Questions? Call us: (888) 625-4885

New Heritage Hills

3505 BELLAND CIR F, CLERMONT, FL, 34711, Clermont, FL 34711

$350,000

2 beds

2 baths

1,503 sq ft

Townhouse

3505 BELLAND CIR F, CLERMONT, FL, 34711

Community: Heritage Hills

New The Villages®

6088 KECKONEN DR, THE VILLAGES, FL, 3216..., The Villages, FL 32163

$749,900

3 beds

2 baths

1,960 sq ft

House

6088 KECKONEN DR, THE VILLAGES, FL, 3216...

Community: The Villages®

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.

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98 communities

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

98 communities near Winter Park

2,733 homes near Winter Park

2 beds

2 baths

1,574 sq ft

House

3 beds

2 baths

1,837 sq ft

Villa

2 beds

2 baths

1,434 sq ft

Villa

3 beds

2 baths

1,943 sq ft

House

3 beds

2 baths

1,209 sq ft

House

3 beds

2 baths

1,392 sq ft

House

2 beds

2 baths

1,344 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

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

3 beds

2 baths

1,718 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

1,308 sq ft

House

2 beds

2 baths

1,928 sq ft

House

3 beds

2 baths

2,058 sq ft

House

2 beds