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

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® 471 GASKIN LN, THE VILLAGES, FL, 32162, The Villages, FL 32162
$439,900

3 beds

|

2 baths

|

1,732 sq ft

|

House

471 GASKIN LN, THE VILLAGES, FL, 32162
Community: The Villages®
Royal Highlands 4814 SAINT ANDREWS ARC, LEESBURG, FL, 34..., Leesburg, FL 34748
$299,999

3 beds

|

2 baths

|

1,728 sq ft

|

House

4814 SAINT ANDREWS ARC, LEESBURG, FL, 34...
Community: Royal Highlands
The Villages® 3942 ZENITH LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$506,000

3 beds

|

2 baths

|

1,922 sq ft

|

House

3942 ZENITH LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
Solivita 270 ADDISON DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$439,000

3 beds

|

2 baths

|

2,159 sq ft

|

House

270 ADDISON DR, POINCIANA, FL, 34759
Community: Solivita
American Village 73 GREEN CIR, PALM COAST, FL, 32164, Palm Coast, FL 32164
$369,990

2 beds

|

2 baths

|

1,799 sq ft

|

House

73 GREEN CIR, PALM COAST, FL, 32164
Community: American Village
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Questions? Call us: (888) 625-4885
Indian River Colony Club 1469 PATRIOT DR, MELBOURNE, FL, 32940, Melbourne, FL 32940
$430,000

4 beds

|

3 baths

|

1,963 sq ft

|

House

1469 PATRIOT DR, MELBOURNE, FL, 32940
The Villages® 8544 SE 177TH BARTRAM LOOP, THE VILLAGES..., The Villages, FL 32162
$309,000

3 beds

|

2 baths

|

1,481 sq ft

|

House

8544 SE 177TH BARTRAM LOOP, THE VILLAGES...
Community: The Villages®
The Villages® 2142 MARGARITA DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$380,000

3 beds

|

2 baths

|

1,904 sq ft

|

House

2142 MARGARITA DR, THE VILLAGES, FL, 321...
Community: The Villages®
Four Seasons at Orlando 2051 FLORA PASS PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$535,000

3 beds

|

2 baths

|

1,964 sq ft

|

House

2051 FLORA PASS PL, KISSIMMEE, FL, 34747
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.
American Village 43 GREEN CIR, PALM COAST, FL, 32164, Palm Coast, FL 32164
$354,990

3 beds

|

2 baths

|

1,604 sq ft

|

House

43 GREEN CIR, PALM COAST, FL, 32164
Community: American Village
American Village 71 GREEN CIR, PALM COAST, FL, 32164, Palm Coast, FL 32164
$349,990

4 beds

|

2 baths

|

1,986 sq ft

|

House

71 GREEN CIR, PALM COAST, FL, 32164
Community: American Village
Foxwood Lake Estates 4903 DEERWOOD DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$174,999

2 beds

|

2 baths

|

1,248 sq ft

|

Manufactured Home

4903 DEERWOOD DR, LAKELAND, FL, 33810
Foxwood Lake Estates 5082 FOX CLIFF DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$199,999

2 beds

|

2 baths

|

1,352 sq ft

|

Manufactured Home

5082 FOX CLIFF DR, LAKELAND, FL, 33810
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Huntington at Hunter's Ridge 13 FAWN HAVEN TRL, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$409,900

4 beds

|

3 baths

|

2,156 sq ft

|

House

13 FAWN HAVEN TRL, ORMOND BEACH, FL, 321...
Plantation Bay Golf & Country Club 1130 HANSBERRY CT, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$324,900

3 beds

|

2 baths

|

1,551 sq ft

|

Townhouse

1130 HANSBERRY CT, ORMOND BEACH, FL, 321...
Arlington Ridge 4358 ANTIETAM CREEK TRL, LEESBURG, FL, 3..., Leesburg, FL 34748
$379,900

3 beds

|

2 baths

|

1,776 sq ft

|

House

4358 ANTIETAM CREEK TRL, LEESBURG, FL, 3...
Community: Arlington Ridge
Solivita 650 CARMEL LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$439,900

3 beds

|

2 baths

|

2,352 sq ft

|

House

650 CARMEL LN, KISSIMMEE, FL, 34759
Community: Solivita
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.
Lake Ashton 5225 PEBBLE BEACH BLVD, WINTER HAVEN, FL..., Winter Haven, FL 33884
$448,900

3 beds

|

2 baths

|

2,031 sq ft

|

House

5225 PEBBLE BEACH BLVD, WINTER HAVEN, FL...
Community: Lake Ashton
The Villages® 2757 PLAINRIDGE LOOP, THE VILLAGES, FL, ..., The Villages, FL 32162
$349,900

2 beds

|

2 baths

|

1,142 sq ft

|

House

2757 PLAINRIDGE LOOP, THE VILLAGES, FL, ...
Community: The Villages®
The Villages® 714 DEL ROSARIO ST, THE VILLAGES, FL, 32..., The Villages, FL 32159
$379,000

3 beds

|

2 baths

|

1,908 sq ft

|

House

714 DEL ROSARIO ST, THE VILLAGES, FL, 32...
Community: The Villages®
Lakes at Laurel Highlands 2162 BLUE HIGHLANDS DR, LAKELAND, FL, 33..., Lakeland, FL 33811
$314,900

3 beds

|

2 baths

|

1,784 sq ft

|

House

2162 BLUE HIGHLANDS DR, LAKELAND, FL, 33...
Want to learn more about 55+ communities in Winter Park? 55places can help!
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Twin Lakes 5114 TWIN LAKES BLVD, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772
$549,370

2 beds

|

2 baths

|

1,917 sq ft

|

House

5114 TWIN LAKES BLVD, SAINT CLOUD, FL, 3...
Community: Twin Lakes
Twin Lakes 2758 MIDSWEET AVE, SAINT CLOUD, FL, 3477..., Saint Cloud, FL 34772
$474,810

2 beds

|

2 baths

|

1,981 sq ft

|

House

2758 MIDSWEET AVE, SAINT CLOUD, FL, 3477...
Community: Twin Lakes
Park Place 76 PARK PLACE CIR, PALM COAST, FL, 32164, Palm Coast, FL 32164
$385,000

3 beds

|

2 baths

|

1,786 sq ft

|

House

76 PARK PLACE CIR, PALM COAST, FL, 32164
Community: Park Place
Arlington Ridge 26821 AUGUSTA SPRINGS CIR, LEESBURG, FL,..., Leesburg, FL 34748
$410,000

2 beds

|

2 baths

|

2,282 sq ft

|

House

26821 AUGUSTA SPRINGS CIR, LEESBURG, FL,...
Community: Arlington Ridge
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 116 DUCK HAWK CIR 3040, DAYTONA BEACH, F..., Daytona Beach, FL 32119
$227,000

2 beds

|

2 baths

|

1,467 sq ft

|

Halfplex

116 DUCK HAWK CIR 3040, DAYTONA BEACH, F...
Grand Haven 455 RIVERFRONT DR UNIT A104, PALM COAST,..., Palm Coast, FL 32137
$975,000

3 beds

|

3 baths

|

2,167 sq ft

|

Condo

455 RIVERFRONT DR UNIT A104, PALM COAST,...
Community: Grand Haven
The Villages® 964 KINGMONT TER, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$339,900

2 beds

|

2 baths

|

1,142 sq ft

|

House

964 KINGMONT TER, THE VILLAGES, FL, 3216...
Community: The Villages®
Heritage Hills 3791 SANIBEL ST, CLERMONT, FL, 34711, Clermont, FL 34711
$538,899

3 beds

|

3 baths

|

2,615 sq ft

|

House

3791 SANIBEL ST, CLERMONT, FL, 34711
Community: Heritage Hills
The Villages® 528 VALENCIA PL, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$270,000

2 beds

|

2 baths

|

1,175 sq ft

|

House

528 VALENCIA PL, 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
Sullivan Ranch 21224 NORIC CV, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$495,000

5 beds

|

3 baths

|

2,638 sq ft

|

House

21224 NORIC CV, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
Solivita 505 MILLIFIORA LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$294,500

2 beds

|

2 baths

|

1,548 sq ft

|

House

505 MILLIFIORA LN, KISSIMMEE, FL, 34759
Community: Solivita
Solivita 507 PRESIDO PARK PL, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$304,500

2 beds

|

2 baths

|

1,302 sq ft

|

House

507 PRESIDO PARK PL, KISSIMMEE, FL, 3475...
Community: Solivita
Solivita 540 GRAND CANAL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$195,000

2 beds

|

2 baths

|

1,507 sq ft

|

House

540 GRAND CANAL DR, KISSIMMEE, FL, 34759
Community: Solivita
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.
The Villages® 4346 HELENA TER, THE VILLAGES, FL, 32163, The Villages, FL 32163
$347,900

2 beds

|

2 baths

|

1,295 sq ft

|

House

4346 HELENA TER, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 9345 SE 177TH SIMONS LN, THE VILLAGES, F..., The Villages, FL 32162
$320,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

9345 SE 177TH SIMONS LN, THE VILLAGES, F...
Community: The Villages®
Royal Harbor 3257 BALTIC SEA BLVD, TAVARES, FL, 32778, Tavares, FL 32778
$389,999

3 beds

|

3 baths

|

2,012 sq ft

|

House

3257 BALTIC SEA BLVD, TAVARES, FL, 32778
Community: Royal Harbor
The Villages® 1705 BETRILLO CT, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$234,900

3 beds

|

2 baths

|

1,210 sq ft

|

House

1705 BETRILLO CT, THE VILLAGES, FL, 3216...
Community: The Villages®
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Royal Highlands 5610 KING JAMES AVE, LEESBURG, FL, 34748, Leesburg, FL 34748
$249,900

3 beds

|

2 baths

|

1,606 sq ft

|

House

5610 KING JAMES AVE, LEESBURG, FL, 34748
Community: Royal Highlands
Vienna Square 1709 LINZ CT, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$259,000

2 beds

|

2 baths

|

1,164 sq ft

|

Villa

1709 LINZ CT, WINTER HAVEN, FL, 33884
Community: Vienna Square

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2,398 homes
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