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Winter Park, FL 55+ active adult communities & homes for sale - Page 46

2,513 homes near Winter Park

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4 rating (17 reviews) The Villages®
$100ks - $1Ms
The Villages®, The Villages, FL
New and Resale | 55+ age-restricted | Built 1978 - present | 70,000 homes
4.7 rating (18 reviews) Solivita
$300ks - $700ks
Solivita, Kissimmee, FL
New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 homes
4.5 rating (11 reviews) Spruce Creek Country Club
$100ks - $400ks
Spruce Creek Country Club, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1996 - 2007 | 3,250 homes
Venetian Bay
$300ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 homes
5 rating (2 reviews) Plantation at Leesburg
$100ks - $300ks
Plantation at Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 homes
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3.6 rating (48 reviews) Latitude Margaritaville
$300ks - $800ks
Latitude Margaritaville, Daytona Beach, FL
Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 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 (1 reviews) Plantation Bay Golf &...
$400ks - $2Ms
Plantation Bay Golf &..., Ormond Beach, FL
New and Resale | Age-targeted | Built 1988 - present | 3,500 homes
5 rating (3 reviews) Lake Ashton
$200ks - $500ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 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.
3.8 rating (4 reviews) Spruce Creek South
$100ks - $200ks
Spruce Creek South, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes
5 rating (1 reviews) Del Webb Sunbridge
$400ks - $800ks
Del Webb Sunbridge, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 homes
5 rating (8 reviews) Royal Highlands
$200ks - $400ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes
5 rating (7 reviews) Kings Ridge
$200ks - $400ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 homes
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Grand Haven
$200ks - $800ks
Grand Haven, Palm Coast, FL
New and Resale | Age-targeted | Built 1997 - present | 1,901 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 (3 reviews) Twin Lakes
$200ks - $600ks
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
Halifax Plantation
$300ks - $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale | Age-targeted | Built 1980 - present | 1,000 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.
5 rating (1 reviews) Sandpiper Golf & Coun...
$100ks - $300ks
Sandpiper Golf & Coun..., Lakeland, FL
New and Resale | 55+ age-restricted | Built 1985 - present | 1,193 homes
2.8 rating (6 reviews) Arlington Ridge
$200ks - $500ks
Arlington Ridge, Leesburg, FL
New and Resale | 55+ age-restricted | Built 2005 - present | 629 homes
Pelican Bay Daytona Beach
$100ks - $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 homes
4 rating (4 reviews) Lakes of Mount Dora
$300ks - $900ks
Lakes of Mount Dora, Mount Dora, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes
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Questions? Call us: (888) 625-4885
4 rating (2 reviews) Harbor Hills Country Club
$300ks - $900ks
Harbor Hills Country Club, Lady Lake, FL
New and Resale | Age-targeted | Built 1989 - present | 940 homes
3.6 rating (5 reviews) Heritage Hills
$200ks - $400ks
Heritage Hills, Clermont, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 1,154 homes
1 rating (1 reviews) Sullivan Ranch
$200ks - $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 homes
5 rating (2 reviews) Heritage Isle
$300ks - $500ks
Heritage Isle, Viera, FL
Resale Only | 55+ age-restricted | Built 2005 - 2017 | 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) Pennbrooke Fairways
<$100k - $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes
4.8 rating (6 reviews) Highland Lakes
$100ks - $200ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
5 rating (1 reviews) Royal Harbor
$200ks - $800ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes
Four Seasons at Orlando
$300ks - $600ks
Four Seasons at Orlando, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2017 - present | 557 homes
5 rating (1 reviews) Cresswind at Victoria Gar...
$200ks - $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
Scottish Highlands
$100ks - $200ks
Scottish Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1983 - 1992 | 653 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
Tohoqua Reserve
$300ks - $600ks
Tohoqua Reserve, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2021 - present | 258 homes
4.4 rating (16 reviews) Del Webb Orlando
$200ks - $500ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 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.
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
The Lakes at Harmony
$200ks - $400ks
The Lakes at Harmony, Harmony, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 400 homes
Summer Trees
$200ks - $400ks
Summer Trees, Port Orange, FL
Resale Only | 55+ age-restricted | Built 1976 - 2005 | 500 homes
Breakaway Trails
$400ks - $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Foxwood Lake Estates
$100ks - $200ks
Foxwood Lake Estates, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1982 - 1987 | 545 homes
Gatherings of Lake Nona
$300ks - $400ks
Gatherings of Lake Nona, Orlando, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 216 homes
12...3
Plantation at Leesburg 4704 RIVER RIDGE DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$425,000

3 beds

|

2 baths

|

2,155 sq ft

|

House

4704 RIVER RIDGE DR, LEESBURG, FL, 34748
Lake Ashton 6165 PEBBLE BEACH BLVD, WINTER HAVEN, FL..., Winter Haven, FL 33884
$469,000

3 beds

|

2 baths

|

2,045 sq ft

|

House

6165 PEBBLE BEACH BLVD, WINTER HAVEN, FL...
Community: Lake Ashton
The Villages® 9653 SE 171ST ARGYLL ST, THE VILLAGES, F..., The Villages, FL 32162
$319,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

9653 SE 171ST ARGYLL ST, THE VILLAGES, F...
Community: The Villages®
Sullivan Ranch 21632 HIDDEN CRK, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$695,000

4 beds

|

4 baths

|

3,853 sq ft

|

House

21632 HIDDEN CRK, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
Spruce Creek South 10767 SE 174TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$239,000

3 beds

|

2 baths

|

1,690 sq ft

|

House

10767 SE 174TH LOOP, SUMMERFIELD, FL, 34...
Community: Spruce Creek South
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Stonecrest 12459 SE 176TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$299,900

3 beds

|

2 baths

|

1,326 sq ft

|

House

12459 SE 176TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
Del Webb Oasis 15162 CANOPY COVER DR, WINTER GARDEN, FL..., Winter Garden, FL 34787
$885,000

2 beds

|

2 baths

|

2,049 sq ft

|

House

15162 CANOPY COVER DR, WINTER GARDEN, FL...
Community: Del Webb Oasis
The Lakes at Harmony 3168 SONGBIRD CIR, ST CLOUD, FL, 34773, St Cloud, FL 34773
$375,000

3 beds

|

2 baths

|

1,850 sq ft

|

House

3168 SONGBIRD CIR, ST CLOUD, FL, 34773
The Villages® 7858 SE 171ST BUCHANAN PL, THE VILLAGES,..., The Villages, FL 32162
$286,000

2 beds

|

2 baths

|

1,186 sq ft

|

Villa

7858 SE 171ST BUCHANAN PL, THE VILLAGES,...
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.
Venetian Bay 3328 MARSILI AVE, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$389,000

3 beds

|

2 baths

|

1,423 sq ft

|

House

3328 MARSILI AVE, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
The Villages® 8065 SE 175TH COLUMBIA PL, THE VILLAGES,..., The Villages, FL 32162
$274,900

2 beds

|

2 baths

|

1,120 sq ft

|

House

8065 SE 175TH COLUMBIA PL, THE VILLAGES,...
Community: The Villages®
The Villages® 9179 SE 167TH FORD ST, THE VILLAGES, FL,..., The Villages, FL 32162
$300,000

2 beds

|

2 baths

|

1,152 sq ft

|

Villa

9179 SE 167TH FORD ST, THE VILLAGES, FL,...
Community: The Villages®
Grand Haven 14 IBIS CT, PALM COAST, FL, 32137, Palm Coast, FL 32137
$465,000

3 beds

|

2 baths

|

2,043 sq ft

|

House

14 IBIS CT, PALM COAST, FL, 32137
Community: Grand Haven
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Grand Haven 150 W WATERSIDE PKWY, PALM COAST, FL, 32..., Palm Coast, FL 32137
$375,000

2 beds

|

2 baths

|

1,619 sq ft

|

House

150 W WATERSIDE PKWY, PALM COAST, FL, 32...
Community: Grand Haven
The Villages® 1016 PICKERING PATH, THE VILLAGES, FL, 3..., The Villages, FL 32163
$694,000

3 beds

|

2 baths

|

2,230 sq ft

|

House

1016 PICKERING PATH, THE VILLAGES, FL, 3...
Community: The Villages®
Lake Ashton 4480 STRATHMORE DR, LAKE WALES, FL, 3385..., Lake Wales, FL 33859
$280,000

2 beds

|

2 baths

|

1,523 sq ft

|

House

4480 STRATHMORE DR, LAKE WALES, FL, 3385...
Community: Lake Ashton
Stonecrest 11041 SE 174TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$450,000

4 beds

|

3 baths

|

2,628 sq ft

|

House

11041 SE 174TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
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.
Traditions at Lake Ruby 3348 RALEIGH DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$227,400

2 beds

|

2 baths

|

1,185 sq ft

|

House

3348 RALEIGH DR, WINTER HAVEN, FL, 33884
The Villages® 3068 SPANISH MOSS WAY, THE VILLAGES, FL,..., The Villages, FL 32163
$765,000

3 beds

|

2 baths

|

2,309 sq ft

|

House

3068 SPANISH MOSS WAY, THE VILLAGES, FL,...
Community: The Villages®
Spruce Creek Country Club 13026 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491
$399,999

2 beds

|

3 baths

|

2,722 sq ft

|

House

13026 SE 97TH TERRACE RD, SUMMERFIELD, F...
Twin Lakes 2557 YELLOW BRICK RD, ST CLOUD, FL, 3477..., St Cloud, FL 34772
$319,900

2 beds

|

2 baths

|

1,464 sq ft

|

Villa

2557 YELLOW BRICK RD, ST CLOUD, FL, 3477...
Community: Twin Lakes
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Lakes of Mount Dora 8852 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757
$515,000

3 beds

|

2 baths

|

2,081 sq ft

|

House

8852 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...
Community: Lakes of Mount Dora
Gatherings of Lake Nona 7573 LAUREATE BLVD 1-305, ORLANDO, FL, 3..., Orlando, FL 32827
$349,995

2 beds

|

2 baths

|

1,486 sq ft

|

Condo

7573 LAUREATE BLVD 1-305, ORLANDO, FL, 3...
Latitude Margaritaville 280 LAST MANGO DR, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124
$389,000

2 beds

|

2 baths

|

1,456 sq ft

|

Villa

280 LAST MANGO DR, DAYTONA BEACH, FL, 32...
Twin Lakes 5027 DANCY LN, ST CLOUD, FL, 34772, St Cloud, FL 34772
$515,000

3 beds

|

3 baths

|

2,197 sq ft

|

House

5027 DANCY LN, ST CLOUD, FL, 34772
Community: Twin Lakes
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® 2879 REMINGTON RD, THE VILLAGES, FL, 321..., The Villages, FL 32162
$379,900

3 beds

|

2 baths

|

1,699 sq ft

|

Villa

2879 REMINGTON RD, THE VILLAGES, FL, 321...
Community: The Villages®
Halifax Plantation 1480 KILRUSH DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$614,000

4 beds

|

3 baths

|

2,788 sq ft

|

House

1480 KILRUSH DR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
Royal Highlands 20642 PRINCE RANIER PL, LEESBURG, FL, 34..., Leesburg, FL 34748
$299,000

2 beds

|

2 baths

|

1,592 sq ft

|

House

20642 PRINCE RANIER PL, LEESBURG, FL, 34...
Community: Royal Highlands
Royal Palm 1315 COCONUT PALM CIR, PORT ORANGE, FL, ..., Port Orange, FL 32128
$414,800

4 beds

|

2 baths

|

1,989 sq ft

|

House

1315 COCONUT PALM CIR, PORT ORANGE, FL, ...
Community: Royal Palm
Trilogy® Orlando 615 CONSERVATION BLVD, GROVELAND, FL, 34..., Groveland, FL 34736
$375,000

2 beds

|

3 baths

|

2,009 sq ft

|

House

615 CONSERVATION BLVD, GROVELAND, FL, 34...
Community: Trilogy® Orlando
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 791 ENISGROVE WAY, THE VILLAGES, FL, 321..., The Villages, FL 32163
$465,000

3 beds

|

2 baths

|

1,956 sq ft

|

House

791 ENISGROVE WAY, THE VILLAGES, FL, 321...
Community: The Villages®
Pennbrooke Fairways 131 WILLOW BROOK DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$232,900

3 beds

|

2 baths

|

1,720 sq ft

|

House

131 WILLOW BROOK DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Spruce Creek South 10337 SE 176TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$239,800

3 beds

|

2 baths

|

1,526 sq ft

|

House

10337 SE 176TH ST, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
The Villages® 1052 JACKSON ST, THE VILLAGES, FL, 32162, The Villages, FL 32162
$419,900

2 beds

|

2 baths

|

1,258 sq ft

|

Villa

1052 JACKSON ST, THE VILLAGES, FL, 32162
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.
Tohoqua Reserve 1855 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744
$365,000

2 beds

|

2 baths

|

1,559 sq ft

|

Villa

1855 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
Legacy of Leesburg 5304 FANTASY WAY, LEESBURG, FL, 34748, Leesburg, FL 34748
$322,222

3 beds

|

2 baths

|

2,087 sq ft

|

House

5304 FANTASY WAY, LEESBURG, FL, 34748
Community: Legacy of Leesburg
The Villages® 560 SMITHFIELD PL, THE VILLAGES, FL, 321..., The Villages, FL 32162
$399,000

3 beds

|

2 baths

|

1,667 sq ft

|

House

560 SMITHFIELD PL, THE VILLAGES, FL, 321...
Community: The Villages®
Four Seasons at Orlando 1855 FLORA PASS PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$329,990

2 beds

|

2 baths

|

1,437 sq ft

|

Villa

1855 FLORA PASS PL, KISSIMMEE, FL, 34747
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Legacy of Leesburg 27400 ORCHID GLADE ST, LEESBURG, FL, 347..., Leesburg, FL 34748
$375,000

3 beds

|

2 baths

|

1,804 sq ft

|

House

27400 ORCHID GLADE ST, LEESBURG, FL, 347...
Community: Legacy of Leesburg
Venetian Bay 3009 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$299,000

3 beds

|

3 baths

|

1,614 sq ft

|

Townhouse

3009 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay

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2,513 homes
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