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Winter Park, FL 55+ active adult communities & homes for sale - Page 44

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
Want to learn more about 55+ communities in Winter Park? 55places can help!
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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® 3459 OLDHAM LN, THE VILLAGES, FL, 32163, The Villages, FL 32163
$424,900

3 beds

|

2 baths

|

1,446 sq ft

|

Villa

3459 OLDHAM LN, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 1258 WEATON CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$359,000

3 beds

|

2 baths

|

1,477 sq ft

|

House

1258 WEATON CT, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 1221 SANTA CRUZ DR, THE VILLAGES, FL, 32..., The Villages, FL 32162
$289,900

2 beds

|

2 baths

|

1,174 sq ft

|

Villa

1221 SANTA CRUZ DR, THE VILLAGES, FL, 32...
Community: The Villages®
Stonecrest 11276 SE 170TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$389,000

3 beds

|

2 baths

|

2,000 sq ft

|

House

11276 SE 170TH PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Twin Lakes 5037 FALLGLO WAY, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772
$539,900

3 beds

|

3 baths

|

2,208 sq ft

|

House

5037 FALLGLO WAY, SAINT CLOUD, FL, 34772
Community: Twin Lakes
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 845 VASQUEZ AVE, THE VILLAGES, FL, 32163, The Villages, FL 32163
$479,000

3 beds

|

2 baths

|

1,652 sq ft

|

House

845 VASQUEZ AVE, THE VILLAGES, FL, 32163
Community: The Villages®
Pennbrooke Fairways 738 COTTAGE PARK LN, LEESBURG, FL, 34748, Leesburg, FL 34748
$139,500

1 beds

|

1 baths

|

588 sq ft

|

House

738 COTTAGE PARK LN, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Lakeside Landings 10199 MAINSAIL DR, OXFORD, FL, 34484, Oxford, FL 34484
$364,900

3 beds

|

2 baths

|

1,537 sq ft

|

Villa

10199 MAINSAIL DR, OXFORD, FL, 34484
Community: Lakeside Landings
Solivita 157 SAND PIPER DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$329,990

3 beds

|

3 baths

|

2,267 sq ft

|

House

157 SAND PIPER 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® 1819 ZIRCON PL, THE VILLAGES, FL, 32163, The Villages, FL 32163
$719,900

4 beds

|

2 baths

|

2,534 sq ft

|

House

1819 ZIRCON PL, THE VILLAGES, FL, 32163
Community: The Villages®
Stonecrest 17409 SE 111TH CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$330,000

3 beds

|

2 baths

|

1,700 sq ft

|

House

17409 SE 111TH CIR, SUMMERFIELD, FL, 344...
Community: Stonecrest
Stonecrest 17446 SE 115TH TERRACE RD, SUMMERFIELD, ..., Summerfield, FL 34491
$314,900

3 beds

|

2 baths

|

1,681 sq ft

|

House

17446 SE 115TH TERRACE RD, SUMMERFIELD, ...
Community: Stonecrest
The Villages® 2377 LONGBOW TRL, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$360,000

3 beds

|

2 baths

|

1,512 sq ft

|

House

2377 LONGBOW TRL, 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
High Vista at Ridgewood Lakes 457 GOLF VISTA CIR, DAVENPORT, FL, 33837, Davenport, FL 33837
$375,000

4 beds

|

3 baths

|

2,211 sq ft

|

House

457 GOLF VISTA CIR, DAVENPORT, FL, 33837
Spruce Creek South 17970 SE 102ND CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$274,000

3 beds

|

2 baths

|

1,708 sq ft

|

House

17970 SE 102ND CT, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
The Villages® 516 LOMA PASEO DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$394,500

3 beds

|

2 baths

|

1,642 sq ft

|

House

516 LOMA PASEO DR, THE VILLAGES, FL, 321...
Community: The Villages®
Spruce Creek Country Club 9891 SE 138TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$284,900

3 beds

|

2 baths

|

1,760 sq ft

|

House

9891 SE 138TH LOOP, SUMMERFIELD, FL, 344...
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.
Harbor Hills Country Club 6008 APEX WAY, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$749,500

4 beds

|

3 baths

|

3,432 sq ft

|

House

6008 APEX WAY, LADY LAKE, FL, 32159
Legacy of Leesburg 27328 PINE STRAW RD, LEESBURG, FL, 34748, Leesburg, FL 34748
$375,000

3 beds

|

2 baths

|

1,894 sq ft

|

House

27328 PINE STRAW RD, LEESBURG, FL, 34748
Community: Legacy of Leesburg
Spruce Creek South 17533 SE 96TH CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$254,900

2 beds

|

2 baths

|

1,534 sq ft

|

House

17533 SE 96TH CT, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
Four Seasons at Orlando 7748 FOUR SEASONS BLVD, KISSIMMEE, FL, 3..., Kissimmee, FL 34747
$729,500

3 beds

|

3 baths

|

2,754 sq ft

|

House

7748 FOUR SEASONS BLVD, KISSIMMEE, FL, 3...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Cresswind at Victoria Gardens 1079 LINCOLNSHIRE DR, DELAND, FL, 32724, Deland, FL 32724
$369,900

2 beds

|

2 baths

|

1,651 sq ft

|

House

1079 LINCOLNSHIRE DR, DELAND, FL, 32724
Solivita 501 HEARTWELL DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$315,000

2 beds

|

2 baths

|

1,574 sq ft

|

House

501 HEARTWELL DR, POINCIANA, FL, 34759
Community: Solivita
Halifax Plantation 3169 CONNEMARA DR, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$375,000

3 beds

|

2 baths

|

1,919 sq ft

|

House

3169 CONNEMARA DR, ORMOND BEACH, FL, 321...
Community: Halifax Plantation
The Villages® 17096 SE 96TH CHAPELWOOD CIR, THE VILLAG..., The Villages, FL 32162
$299,900

3 beds

|

2 baths

|

1,527 sq ft

|

House

17096 SE 96TH CHAPELWOOD CIR, THE VILLAG...
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.
Arlington Ridge 27103 CAMERONS RUN, LEESBURG, FL, 34748, Leesburg, FL 34748
$460,000

3 beds

|

2 baths

|

2,236 sq ft

|

House

27103 CAMERONS RUN, LEESBURG, FL, 34748
Community: Arlington Ridge
Grand Haven 200 RIVERFRONT DR B103, PALM COAST, FL, ..., Palm Coast, FL 32137
$375,000

3 beds

|

2 baths

|

1,762 sq ft

|

Condo

200 RIVERFRONT DR B103, PALM COAST, FL, ...
Community: Grand Haven
New High Vista at Ridgewood Lakes 245 FITZGERALD LN, DAVENPORT, FL, 33837, Davenport, FL 33837
$285,000

2 beds

|

2 baths

|

1,388 sq ft

|

House

245 FITZGERALD LN, DAVENPORT, FL, 33837
Trilogy® Orlando 108 CRESCENT MOON DR, GROVELAND, FL, 347..., Groveland, FL 34736
$275,000

3 beds

|

2 baths

|

1,974 sq ft

|

House

108 CRESCENT MOON DR, GROVELAND, FL, 347...
Community: Trilogy® Orlando
Venetian Bay 3218 MEDICI BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$639,900

4 beds

|

2 baths

|

2,240 sq ft

|

House

3218 MEDICI BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Want to learn more about 55+ communities in Winter Park? 55places can help!
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Venetian Bay 351 VENETIAN PALMS BLVD, NEW SMYRNA BEAC..., New Smyrna Beach, FL 32168
$569,000

3 beds

|

2 baths

|

1,987 sq ft

|

House

351 VENETIAN PALMS BLVD, NEW SMYRNA BEAC...
Community: Venetian Bay
Ridgehaven 1320 OAKHAVEN AVE, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$418,420

4 beds

|

2 baths

|

1,908 sq ft

|

House

1320 OAKHAVEN AVE, ORMOND BEACH, FL, 321...
Community: Ridgehaven
The Villages® 1019 AVALON AVE, THE VILLAGES, FL, 32159, The Villages, FL 32159
$280,000

2 beds

|

2 baths

|

1,623 sq ft

|

Villa

1019 AVALON AVE, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 1092 INCORVAIA WAY, THE VILLAGES, FL, 32..., The Villages, FL 32163
$639,900

3 beds

|

3 baths

|

2,409 sq ft

|

House

1092 INCORVAIA WAY, THE VILLAGES, FL, 32...
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.
The Villages® 8039 SE 174TH BELHAVEN LOOP, THE VILLAGE..., The Villages, FL 32162
$325,000

3 beds

|

2 baths

|

1,265 sq ft

|

House

8039 SE 174TH BELHAVEN LOOP, THE VILLAGE...
Community: The Villages®
New Grand Haven 83 FRONT ST, PALM COAST, FL, 32137, Palm Coast, FL 32137
$1,250,000

4 beds

|

4 baths

|

3,259 sq ft

|

House

83 FRONT ST, PALM COAST, FL, 32137
Community: Grand Haven
Twin Lakes 2410 DATURA LOOP, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772
$369,000

2 beds

|

2 baths

|

1,464 sq ft

|

Villa

2410 DATURA LOOP, SAINT CLOUD, FL, 34772
Community: Twin Lakes
New The Villages® 4774 COSENTINO CT, THE VILLAGES, FL, 321..., The Villages, FL 32163
$659,000

3 beds

|

2 baths

|

2,024 sq ft

|

House

4774 COSENTINO CT, THE VILLAGES, FL, 321...
Community: The Villages®
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
New Solivita 2825 PALM TREE DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$349,000

2 beds

|

2 baths

|

1,839 sq ft

|

Villa

2825 PALM TREE DR, KISSIMMEE, FL, 34759
Community: Solivita
New Summit Greens 916 WOLF CREEK ST, CLERMONT, FL, 34711, Clermont, FL 34711
$319,000

3 beds

|

2 baths

|

1,872 sq ft

|

House

916 WOLF CREEK ST, CLERMONT, FL, 34711
Community: Summit Greens

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