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

2,487 homes near Winter Park

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4 rating (17 reviews)

The Villages®

<$100k - $1Ms

The Villages®, The Villages, FL

New and Resale | 55+ age-restricted | Built 1978 - present | 70,000 homes

4.7 rating (18 reviews)

Solivita

$100Ks - $600Ks

Solivita, Kissimmee, FL

New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 homes

3.6 rating (48 reviews)

Latitude Margaritaville

$300Ks - $900Ks

Latitude Margaritaville, Daytona Beach, FL

Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes

5 rating (1 reviews)

Plantation Bay Golf &...

$200Ks - $4Ms

Plantation Bay Golf &..., Ormond Beach, FL

New and Resale | Age-targeted | Built 1988 - present | 3,500 homes

4.5 rating (11 reviews)

Spruce Creek Country Club

$200Ks - $500Ks

Spruce Creek Country Club, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1996 - 2007 | 3,250 homes

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5 rating (2 reviews)

Plantation at Leesburg

$100Ks - $500Ks

Plantation at Leesburg, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 homes

5 rating (3 reviews)

Stonecrest

$200Ks - $500Ks

Stonecrest, Summerfield, FL

New and Resale | 55+ age-restricted | Built 1990 - present | 2,200 homes

5 rating (7 reviews)

Kings Ridge

$200Ks - $400Ks

Kings Ridge, Clermont, FL

Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 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

Grand Haven

$300Ks - $1Ms

Grand Haven, Palm Coast, FL

New and Resale | Age-targeted | Built 1997 - present | 1,901 homes

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Pelican Bay Daytona Beach

$100Ks - $500Ks

Pelican Bay Daytona Beach, Daytona Beach, FL

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

4.7 rating (3 reviews)

Spruce Creek South

$100Ks - $300Ks

Spruce Creek South, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes

5 rating (1 reviews)

Cypress Lakes

$100Ks - $200Ks

Cypress Lakes, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 homes

5 rating (3 reviews)

Lake Ashton

$200Ks - $800Ks

Lake Ashton, Lake Wales, FL

Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes

Venetian Bay

$200Ks - $1Ms

Venetian Bay, New Smyrna Beach, FL

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

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

Questions? Call us: (888) 625-4885

5 rating (2 reviews)

Heritage Isle

$200Ks - $500Ks

Heritage Isle, Viera, FL

Resale Only | 55+ age-restricted | Built 2005 - 2017 | 1,500 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 (8 reviews)

Royal Highlands

$200Ks - $500Ks

Royal Highlands, Leesburg, FL

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

5 rating (1 reviews)

Del Webb Sunbridge

$300Ks - $1Ms

Del Webb Sunbridge, St. Cloud, FL

New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 homes

5 rating (1 reviews)

VillageWalk at Lake Nona

$300Ks - $1Ms

VillageWalk at Lake Nona, Orlando, FL

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

Del Webb at Viera

$300Ks - $800Ks

Del Webb at Viera, Melbourne, FL

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

5 rating (8 reviews)

Pennbrooke Fairways

<$100k - $300Ks

Pennbrooke Fairways, Leesburg, FL

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

5 rating (1 reviews)

Sandpiper Golf & Coun...

$200Ks - $400Ks

Sandpiper Golf & Coun..., Lakeland, FL

New and Resale | 55+ age-restricted | Built 1985 - present | 1,193 homes

3.6 rating (5 reviews)

Heritage Hills

$200Ks - $500Ks

Heritage Hills, Clermont, FL

New and Resale | 55+ age-restricted | Built 2006 - present | 1,154 homes

5 rating (1 reviews)

Cresswind at Victoria Gar...

$300Ks - $600Ks

Cresswind at Victoria Gar..., DeLand, FL

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

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Questions? Call us: (888) 625-4885

Halifax Plantation

$200Ks - $700Ks

Halifax Plantation, Ormond Beach, FL

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

Breakaway Trails

$400Ks - $700Ks

Breakaway Trails, Ormond Beach, FL

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

4 rating (4 reviews)

Lakes of Mount Dora

$400Ks - $900Ks

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

$200Ks - $1Ms

Harbor Hills Country Club, Lady Lake, FL

New and Resale | Age-targeted | Built 1989 - present | 940 homes

4.8 rating (6 reviews)

Highland Lakes

$100Ks - $300Ks

Highland Lakes, Leesburg, FL

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

4.4 rating (16 reviews)

Del Webb Orlando

$300Ks - $400Ks

Del Webb Orlando, Davenport, FL

Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes

5 rating (2 reviews)

Bridgewater at Viera

$300Ks - $600Ks

Bridgewater at Viera, Melbourne, FL

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

4.1 rating (9 reviews)

Indian River Colony Club

$200Ks - $400Ks

Indian River Colony Club, Melbourne, FL

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

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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)

Royal Harbor

$200Ks - $400Ks

Royal Harbor, Tavares, FL

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

Lakeside Landings

$200Ks - $500Ks

Lakeside Landings, Oxford, FL

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

1 rating (1 reviews)

Sullivan Ranch

$300Ks - $600Ks

Sullivan Ranch, Mount Dora, FL

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

Highland Fairways

$100Ks - $300Ks

Highland Fairways, Lakeland, FL

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

1 2...3

Trilogy® Orlando

112 FLAME VINE WAY, GROVELAND, FL, 34736, Groveland, FL 34736

$299,000

2 beds

2 baths

1,556 sq ft

House

112 FLAME VINE WAY, GROVELAND, FL, 34736

Community: Trilogy® Orlando

Cresswind at Victoria Gardens

213 OLD MOSS CIR, DELAND, FL, 32724, Deland, FL 32724

$365,000

2 beds

2 baths

1,507 sq ft

House

213 OLD MOSS CIR, DELAND, FL, 32724

434 VENETIAN PALMS BLVD, NEW SMYRNA BEAC...

Community: Venetian Bay

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

Questions? Call us: (888) 625-4885

The Villages®

$415,000

3 beds

2 baths

1,532 sq ft

House

1089 ISLE OF PALMS PATH, THE VILLAGES, F...

Community: The Villages®

The Villages®

$509,900

3 beds

2 baths

1,950 sq ft

House

862 BOWDEN RD, THE VILLAGES, FL, 32163

Community: The Villages®

Plantation Bay Golf & Country Club

1009 SUDBURY LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$2,838,751

4 beds

5 baths

3,927 sq ft

House

1009 SUDBURY LN, ORMOND BEACH, FL, 32174

Community: Plantation Bay Golf & Country Club

New Latitude Margaritaville

280 LAST MANGO DR, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124

$409,900

2 beds

2 baths

1,456 sq ft

Villa

280 LAST MANGO DR, DAYTONA BEACH, FL, 32...

Community: Latitude Margaritaville

Tohoqua Reserve

2015 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744

$420,000

3 beds

2 baths

2,054 sq ft

House

2015 SPRING SHOWER CIR, KISSIMMEE, FL, 3...

Community: Tohoqua Reserve

The Villages®

$429,900

2 beds

3 baths

1,575 sq ft

Villa

1120 AVENIDA DE LAS CASAS, THE VILLAGES,...

Community: The Villages®

Colonnades

$125,000

2 beds

2 baths

1,248 sq ft

Manufactured Home

4805 COLONNADES CIR, LAKELAND, FL, 33811

Community: Colonnades

Kings Ridge

3817 DOUNE WAY, CLERMONT, FL, 34711, Clermont, FL 34711

$289,990

2 beds

2 baths

1,625 sq ft

House

3817 DOUNE WAY, CLERMONT, FL, 34711

Community: Kings Ridge

Tohoqua Reserve

1901 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744

$350,000

2 beds

2 baths

1,559 sq ft

House

1901 SPRING SHOWER CIR, KISSIMMEE, FL, 3...

Community: Tohoqua Reserve

Highland Fairways

3154 PRAIRIE DUNES CIR, LAKELAND, FL, 33..., Lakeland, FL 33810

$235,000

2 beds

2 baths

1,529 sq ft

House

3154 PRAIRIE DUNES CIR, LAKELAND, FL, 33...

Community: Highland Fairways

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

Questions? Call us: (888) 625-4885

Carillon Lakes

4361 WHISTLEWOOD CIR, LAKELAND, FL, 3381..., Lakeland, FL 33811

$429,000

3 beds

3 baths

2,430 sq ft

House

4361 WHISTLEWOOD CIR, LAKELAND, FL, 3381...

Community: Carillon Lakes

Sandpiper Golf & Country Club

6325 EGRET DR, LAKELAND, FL, 33809, Lakeland, FL 33809

$284,000

3 beds

2 baths

1,441 sq ft

House

6325 EGRET DR, LAKELAND, FL, 33809

Community: Sandpiper Golf & Country Club

New Heritage Hills

3768 SERENA LN, CLERMONT, FL, 34711, Clermont, FL 34711

$389,899

3 beds

2 baths

1,856 sq ft

House

3768 SERENA LN, CLERMONT, FL, 34711

Community: Heritage Hills

The Villages®

$325,000

3 beds

2 baths

1,392 sq ft

House

1723 BANBERRY RUN, THE VILLAGES, FL, 321...

Community: The Villages®

Harbor Hills Country Club

6145 SPINNAKER LOOP, LADY LAKE, FL, 3215..., Lady Lake, FL 32159

$649,900

4 beds

3 baths

3,294 sq ft

House

6145 SPINNAKER LOOP, LADY LAKE, FL, 3215...

Community: Harbor Hills Country Club

The Villages®

$775,000

3 beds

2 baths

2,234 sq ft

House

1091 NOBLE WAY, THE VILLAGES, FL, 32162

Community: The Villages®

Royal Highlands

21937 KING ALFRED ST, LEESBURG, FL, 3474..., Leesburg, FL 34748

$550,000

5 beds

3 baths

3,422 sq ft

House

21937 KING ALFRED ST, LEESBURG, FL, 3474...

Community: Royal Highlands

Spruce Creek South

17710 SE 108TH AVE, SUMMERFIELD, FL, 344..., Summerfield, FL 34491

$239,900

2 beds

2 baths

1,496 sq ft

House

17710 SE 108TH AVE, SUMMERFIELD, FL, 344...

Community: Spruce Creek South

Spruce Creek South

10815 SE 178TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$229,900

2 beds

2 baths

1,144 sq ft

House

10815 SE 178TH ST, SUMMERFIELD, FL, 3449...

Community: Spruce Creek South

Heritage Hills

3205 SONESTA CT B, CLERMONT, FL, 34711, Clermont, FL 34711

$285,000

2 beds

2 baths

1,374 sq ft

Villa

3205 SONESTA CT B, CLERMONT, FL, 34711

Community: Heritage Hills

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The Villages®

$279,000

2 beds

2 baths

1,120 sq ft

House

1142 W BOONE CT, THE VILLAGES, FL, 32159

Community: The Villages®

New Twin Lakes

2557 YELLOW BRICK RD, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772

$345,000

2 beds

2 baths

1,464 sq ft

Villa

2557 YELLOW BRICK RD, SAINT CLOUD, FL, 3...

Community: Twin Lakes

New Gatherings of Lake Nona

7573 LAUREATE BLVD UNIT 1305, ORLANDO, F..., Orlando, FL 32827

$449,995

2 beds

2 baths

1,486 sq ft

Condo

7573 LAUREATE BLVD UNIT 1305, ORLANDO, F...

Community: Gatherings of Lake Nona

New Spruce Creek Country Club

9894 SE 138TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491

$419,000

3 beds

2 baths

2,267 sq ft

House

9894 SE 138TH LOOP, SUMMERFIELD, FL, 344...

Community: Spruce Creek Country Club

New The Villages®

1201 DUSTIN DR, THE VILLAGES, FL, 32159, The Villages, FL 32159

$379,000

3 beds

2 baths

1,744 sq ft

House

1201 DUSTIN DR, THE VILLAGES, FL, 32159

Community: The Villages®

New Spruce Creek Country Club

13516 SE 87TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$310,000

2 beds

2 baths

1,575 sq ft

House

13516 SE 87TH CIR, SUMMERFIELD, FL, 3449...

Community: Spruce Creek Country Club

New Lakes of Mount Dora

8852 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757

$535,000

3 beds

2 baths

2,018 sq ft

House

8852 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...

Community: Lakes of Mount Dora

Ridgehaven

445 BROOKHAVEN TRL, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174

$573,000

5 beds

5 baths

3,807 sq ft

House

445 BROOKHAVEN TRL, ORMOND BEACH, FL, 32...

Community: Ridgehaven

The Villages®

$254,900

2 beds

2 baths

1,188 sq ft

Villa

2805 BURGOS DR, THE VILLAGES, FL, 32162

Community: The Villages®

Foxwood Lake Estates

5079 LODGEWOOD DR, LAKELAND, FL, 33810, Lakeland, FL 33810

$189,000

2 beds

2 baths

1,144 sq ft

Manufactured Home

5079 LODGEWOOD DR, LAKELAND, FL, 33810

Community: Foxwood Lake Estates

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8039 SE 174TH BELHAVEN LOOP, THE VILLAGE...

Community: The Villages®

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2,487 homes near Winter Park

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

90 communities near Winter Park

2,487 homes near Winter Park

2 beds

2 baths

1,556 sq ft

House

2 beds

2 baths

1,507 sq ft

House

4 beds

3 baths

2,852 sq ft

House

4 beds

3 baths

2,417 sq ft

House

4 beds

3 baths

2,101 sq ft

House

3 beds

2 baths

1,532 sq ft

House

3 beds

2 baths

1,950 sq ft

House

4 beds

5 baths

3,927 sq ft

House

2 beds

2 baths

1,456 sq ft

Villa

3 beds

2 baths

2,054 sq ft

House

2 beds

3 baths

1,575 sq ft

Villa

2 beds

2 baths

1,248 sq ft

Manufactured Home

2 beds

2 baths

1,625 sq ft

House

2 beds

2 baths

1,559 sq ft

House

2 beds

2 baths

1,529 sq ft

House

3 beds

3 baths

2,430 sq ft

House

3 beds

2 baths

1,441 sq ft

House

3 beds

2 baths

1,856 sq ft

House

3 beds

2 baths

1,392 sq ft

House

4 beds