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Winter Park, FL 55+ active adult communities & homes for sale - Page 32

2,398 homes near Winter Park

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4 rating (17 reviews) The Villages®
<$100k - $2Ms
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 - $3Ms
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
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.
Grand Haven
$300Ks - $1Ms
Grand Haven, Palm Coast, FL
New and Resale | Age-targeted | Built 1997 - present | 1,901 homes
Pelican Bay Daytona Beach
$100Ks - $400Ks
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 - $400Ks
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
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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
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 - $600Ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 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.
5 rating (8 reviews) Royal Highlands
$200Ks - $400Ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes
Del Webb at Viera
$400Ks - $1Ms
Del Webb at Viera, Melbourne, FL
New Construction | 55+ age-restricted | Built 2021 - 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
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
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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
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
$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 - $800Ks
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
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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 - $800Ks
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
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.
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
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
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1 rating (1 reviews) Sullivan Ranch
$200Ks - $700Ks
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
The Villages® 1178 BETHUNE WAY, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$500,000

3 beds

|

2 baths

|

2,085 sq ft

|

House

1178 BETHUNE WAY, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 220 PALERMO PL, THE VILLAGES, FL, 32159, The Villages, FL 32159
$283,000

2 beds

|

2 baths

|

1,383 sq ft

|

House

220 PALERMO PL, THE VILLAGES, FL, 32159
Community: The Villages®
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®
The Villages® 4881 JOHN CRAMER CIR, THE VILLAGES, FL, ..., The Villages, FL 32163
$325,000

3 beds

|

2 baths

|

1,426 sq ft

|

House

4881 JOHN CRAMER CIR, THE VILLAGES, FL, ...
Community: The Villages®
The Villages® 2403 ST GEORGE AVE, THE VILLAGES, FL, 32..., The Villages, FL 32162
$539,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

2403 ST GEORGE AVE, THE VILLAGES, FL, 32...
Community: The Villages®
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Questions? Call us: (888) 625-4885
The Villages® 32 HICKORY HEAD HAMMOCK, THE VILLAGES, F..., The Villages, FL 32159
$1,399,000

3 beds

|

2 baths

|

2,522 sq ft

|

House

32 HICKORY HEAD HAMMOCK, THE VILLAGES, F...
Community: The Villages®
The Villages® 2132 BLACKVILLE DR, THE VILLAGES, FL, 32..., The Villages, FL 32162
$550,000

3 beds

|

3 baths

|

2,400 sq ft

|

House

2132 BLACKVILLE DR, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 944 HORTON TER, THE VILLAGES, FL, 32163, The Villages, FL 32163
$400,000

3 beds

|

2 baths

|

1,647 sq ft

|

Villa

944 HORTON TER, THE VILLAGES, FL, 32163
Community: The Villages®
Del Webb Sunbridge 2698 RIVER CREEK LN, SAINT CLOUD, FL, 34..., Saint Cloud, FL 34771
$595,000

3 beds

|

3 baths

|

2,080 sq ft

|

House

2698 RIVER CREEK LN, SAINT CLOUD, FL, 34...
Community: Del Webb Sunbridge
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.
Solivita 513 VINEYARD WAY, POINCIANA, FL, 34759, Poinciana, FL 34759
$265,000

2 beds

|

2 baths

|

1,240 sq ft

|

House

513 VINEYARD WAY, POINCIANA, FL, 34759
Community: Solivita
Colonnades 4911 COLONNADES CLUB BLVD, LAKELAND, FL,..., Lakeland, FL 33811
$189,000

2 beds

|

2 baths

|

1,514 sq ft

|

Manufactured Home

4911 COLONNADES CLUB BLVD, LAKELAND, FL,...
Community: Colonnades
The Villages® 7886 SE 167TH MISTWOOD LN, THE VILLAGES,..., The Villages, FL 32162
$540,000

3 beds

|

2 baths

|

2,260 sq ft

|

House

7886 SE 167TH MISTWOOD LN, THE VILLAGES,...
Community: The Villages®
Heritage Hills 3547 FAIRWATERS CT A, CLERMONT, FL, 3471..., Clermont, FL 34711
$334,900

2 beds

|

2 baths

|

1,503 sq ft

|

Villa

3547 FAIRWATERS CT A, CLERMONT, FL, 3471...
Community: Heritage Hills
Want to learn more about 55+ communities in Winter Park? 55places can help!
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Solivita 699 GLENDORA RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$474,900

3 beds

|

3 baths

|

2,450 sq ft

|

House

699 GLENDORA RD, KISSIMMEE, FL, 34759
Community: Solivita
Grand Haven 10 S WATERVIEW DR, PALM COAST, FL, 32137, Palm Coast, FL 32137
$819,000

3 beds

|

3 baths

|

2,643 sq ft

|

House

10 S WATERVIEW DR, PALM COAST, FL, 32137
Community: Grand Haven
Grand Haven 6 SCARLET OAK CIR, PALM COAST, FL, 32137, Palm Coast, FL 32137
$829,000

3 beds

|

3 baths

|

2,465 sq ft

|

House

6 SCARLET OAK CIR, PALM COAST, FL, 32137
Community: Grand Haven
The Villages® 987 FREDERICK TER, THE VILLAGES, FL, 321..., The Villages, FL 32163
$815,000

3 beds

|

2 baths

|

2,060 sq ft

|

House

987 FREDERICK TER, THE VILLAGES, FL, 321...
Community: The Villages®
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.
Pelican Bay Daytona Beach 108 BERMUDA PETREL CT, DAYTONA BEACH, FL..., Daytona Beach, FL 32119
$259,900

2 beds

|

2 baths

|

1,394 sq ft

|

House

108 BERMUDA PETREL CT, DAYTONA BEACH, FL...
Del Webb Sunbridge 6224 CITRUS GROVE CT, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34771
$549,835

2 beds

|

2 baths

|

1,405 sq ft

|

House

6224 CITRUS GROVE CT, SAINT CLOUD, FL, 3...
Community: Del Webb Sunbridge
Del Webb Sunbridge 6213 CITRUS GROVE CT, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34771
$924,821

3 beds

|

3 baths

|

2,269 sq ft

|

House

6213 CITRUS GROVE CT, SAINT CLOUD, FL, 3...
Community: Del Webb Sunbridge
Del Webb Oasis 15843 GEM VIEW ST, WINTER GARDEN, FL, 34..., Winter Garden, FL 34787
$459,090

2 beds

|

2 baths

|

1,579 sq ft

|

Villa

15843 GEM VIEW ST, WINTER GARDEN, FL, 34...
Community: Del Webb Oasis
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Del Webb Oasis 15837 GEM VIEW ST, WINTER GARDEN, FL, 34..., Winter Garden, FL 34787
$460,410

2 beds

|

2 baths

|

1,579 sq ft

|

Villa

15837 GEM VIEW ST, WINTER GARDEN, FL, 34...
Community: Del Webb Oasis
Del Webb Oasis 15831 GEM VIEW ST, WINTER GARDEN, FL, 34..., Winter Garden, FL 34787
$452,090

3 beds

|

2 baths

|

1,579 sq ft

|

Villa

15831 GEM VIEW ST, WINTER GARDEN, FL, 34...
Community: Del Webb Oasis
Del Webb Oasis 15825 GEM VIEW ST, WINTER GARDEN, FL, 34..., Winter Garden, FL 34787
$449,080

2 beds

|

2 baths

|

1,579 sq ft

|

Villa

15825 GEM VIEW ST, WINTER GARDEN, FL, 34...
Community: Del Webb Oasis
The Villages® 6230 DINGMAN WAY, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$479,600

3 beds

|

2 baths

|

1,484 sq ft

|

House

6230 DINGMAN WAY, THE VILLAGES, FL, 3216...
Community: The Villages®
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.
VillageWalk at Lake Nona 12287 REGAL LILY LN, ORLANDO, FL, 32827, Orlando, FL 32827
$699,000

3 beds

|

2 baths

|

1,958 sq ft

|

House

12287 REGAL LILY LN, ORLANDO, FL, 32827
The Villages® 603 ROBIN LN, WILDWOOD, FL, 34785, Wildwood, FL 34785
$179,000

2 beds

|

2 baths

|

1,352 sq ft

|

Manufactured Home

603 ROBIN LN, WILDWOOD, FL, 34785
Community: The Villages®
The Villages® 9230 SE 179TH WESLEY ST, THE VILLAGES, F..., The Villages, FL 32162
$269,000

2 beds

|

2 baths

|

1,148 sq ft

|

House

9230 SE 179TH WESLEY ST, THE VILLAGES, F...
Community: The Villages®
Grand Haven 19 LAKEVIEW LN, PALM COAST, FL, 32137, Palm Coast, FL 32137
$679,000

4 beds

|

3 baths

|

2,809 sq ft

|

House

19 LAKEVIEW LN, PALM COAST, FL, 32137
Community: Grand Haven
Halifax Plantation 1312 ARKLOW CIR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$779,000

5 beds

|

5 baths

|

3,825 sq ft

|

House

1312 ARKLOW CIR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Foxwood Lake Estates 4969 FOXWOOD LAKE DR, LAKELAND, FL, 3381..., Lakeland, FL 33810
$185,000

2 beds

|

2 baths

|

1,456 sq ft

|

Manufactured Home

4969 FOXWOOD LAKE DR, LAKELAND, FL, 3381...
Heritage Hills 3557 BELLAND CIR D, CLERMONT, FL, 34711, Clermont, FL 34711
$299,000

2 beds

|

2 baths

|

1,374 sq ft

|

Villa

3557 BELLAND CIR D, CLERMONT, FL, 34711
Community: Heritage Hills
The Villages® 7168 SE 173RD ARLINGTON LOOP, THE VILLAG..., The Villages, FL 32162
$319,000

3 beds

|

2 baths

|

1,512 sq ft

|

House

7168 SE 173RD ARLINGTON LOOP, THE VILLAG...
Community: The Villages®
The Villages® 527 BEVILLE PL, THE VILLAGES, FL, 32163, The Villages, FL 32163
$599,999

3 beds

|

2 baths

|

2,050 sq ft

|

House

527 BEVILLE PL, THE VILLAGES, FL, 32163
Community: The Villages®
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.
Gatherings of Lake Nona 7545 LAUREATE BLVD UNIT 7203, ORLANDO, F..., Orlando, FL 32827
$457,990

2 beds

|

2 baths

|

1,549 sq ft

|

Condo

7545 LAUREATE BLVD UNIT 7203, ORLANDO, F...
Gatherings of Lake Nona 7545 LAUREATE BLVD UNIT 7202, ORLANDO, F..., Orlando, FL 32827
$489,990

3 beds

|

2 baths

|

1,805 sq ft

|

Condo

7545 LAUREATE BLVD UNIT 7202, ORLANDO, F...
Gatherings of Lake Nona 7557 LAUREATE BLVD UNIT 6301, ORLANDO, F..., Orlando, FL 32827
$365,990

2 beds

|

2 baths

|

1,368 sq ft

|

Condo

7557 LAUREATE BLVD UNIT 6301, ORLANDO, F...
Plantation at Leesburg 3644 PLANTATION BLVD, LEESBURG, FL, 3474..., Leesburg, FL 34748
$295,000

2 beds

|

2 baths

|

1,862 sq ft

|

House

3644 PLANTATION BLVD, LEESBURG, FL, 3474...
Want to learn more about 55+ communities in Winter Park? 55places can help!
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Plantation at Leesburg 3728 MULBERRY GROVE LOOP, LEESBURG, FL, ..., Leesburg, FL 34748
$399,000

3 beds

|

2 baths

|

2,636 sq ft

|

House

3728 MULBERRY GROVE LOOP, LEESBURG, FL, ...
Plantation at Leesburg 24502 PARLANGE CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$319,000

2 beds

|

2 baths

|

1,880 sq ft

|

House

24502 PARLANGE CT, LEESBURG, FL, 34748

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2,398 homes
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