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Winter Park, FL 55+ active adult communities & homes for sale - Page 28

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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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
Pelican Bay Daytona Beach 528 SPOTTED SANDPIPER DR, DAYTONA BEACH,..., Daytona Beach, FL 32119
$439,000

3 beds

|

2 baths

|

2,270 sq ft

|

House

528 SPOTTED SANDPIPER DR, DAYTONA BEACH,...
The Villages® 1504 LYNCHBURG LOOP, THE VILLAGES, FL, 3..., The Villages, FL 32162
$359,900

3 beds

|

2 baths

|

1,550 sq ft

|

House

1504 LYNCHBURG LOOP, THE VILLAGES, FL, 3...
Community: The Villages®
Cresswind DeLand 1279 EDEN ROCK CT, DELAND, FL, 32724, Deland, FL 32724
$367,990

2 beds

|

2 baths

|

1,434 sq ft

|

House

1279 EDEN ROCK CT, DELAND, FL, 32724
Community: Cresswind DeLand
The Villages® 829 EVELYNTON LOOP, THE VILLAGES, FL, 32..., The Villages, FL 32162
$289,900

3 beds

|

2 baths

|

1,392 sq ft

|

House

829 EVELYNTON LOOP, THE VILLAGES, FL, 32...
Community: The Villages®
Del Webb Orlando 329 ALICANTE CT, DAVENPORT, FL, 33837, Davenport, FL 33837
$415,000

3 beds

|

2 baths

|

2,000 sq ft

|

House

329 ALICANTE CT, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Solivita 116 GLENDALE CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$319,000

2 beds

|

2 baths

|

1,655 sq ft

|

House

116 GLENDALE CT, KISSIMMEE, FL, 34759
Community: Solivita
Plantation at Leesburg 25239 CRANES ROOST CIR, LEESBURG, FL, 34..., Leesburg, FL 34748
$259,900

2 beds

|

2 baths

|

1,563 sq ft

|

House

25239 CRANES ROOST CIR, LEESBURG, FL, 34...
The Villages® 4138 BURGESS DR, THE VILLAGES, FL, 32163, The Villages, FL 32163
$840,000

3 beds

|

2 baths

|

1,929 sq ft

|

House

4138 BURGESS DR, THE VILLAGES, FL, 32163
Community: The Villages®
Highland Fairways 3104 SAND TRAP CT, LAKELAND, FL, 33810, Lakeland, FL 33810
$320,000

3 beds

|

2 baths

|

1,839 sq ft

|

House

3104 SAND TRAP CT, LAKELAND, FL, 33810
Community: Highland Fairways
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® 3550 YATES AVE, THE VILLAGES, FL, 32163, The Villages, FL 32163
$724,900

3 beds

|

3 baths

|

2,351 sq ft

|

House

3550 YATES AVE, THE VILLAGES, FL, 32163
Community: The Villages®
Solivita 362 VIA TORRENTE DR, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$379,000

2 beds

|

2 baths

|

1,705 sq ft

|

House

362 VIA TORRENTE DR, KISSIMMEE, FL, 3475...
Community: Solivita
Scottish Highlands 2108 GREENLAW CT, LEESBURG, FL, 34788, Leesburg, FL 34788
$235,000

3 beds

|

2 baths

|

1,740 sq ft

|

House

2108 GREENLAW CT, LEESBURG, FL, 34788
Community: Scottish Highlands
Harbor Hills Country Club 5236 ISLAND TERRACE CT, LADY LAKE, FL, 3..., Lady Lake, FL 32159
$407,494

3 beds

|

2 baths

|

2,083 sq ft

|

House

5236 ISLAND TERRACE CT, LADY LAKE, FL, 3...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Del Webb Sunbridge 2499 CLIFF WAY, ST CLOUD, FL, 34771, St Cloud, FL 34771
$479,980

3 beds

|

2 baths

|

1,650 sq ft

|

House

2499 CLIFF WAY, ST CLOUD, FL, 34771
Community: Del Webb Sunbridge
Legacy of Leesburg 5922 SAGE LEAF PL, LEESBURG, FL, 34748, Leesburg, FL 34748
$329,000

3 beds

|

2 baths

|

1,913 sq ft

|

House

5922 SAGE LEAF PL, LEESBURG, FL, 34748
Community: Legacy of Leesburg
Esplanade at Highland Ranch 915 BRAEWOOD DR, CLERMONT, FL, 34715, Clermont, FL 34715
$450,000

2 beds

|

2 baths

|

1,758 sq ft

|

House

915 BRAEWOOD DR, CLERMONT, FL, 34715
Highland Lakes 5636 LAVER ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$264,900

2 beds

|

2 baths

|

1,497 sq ft

|

House

5636 LAVER ST, LEESBURG, FL, 34748
Community: Highland 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.
Heritage Hills 3632 SOLANA CIR B, CLERMONT, FL, 34711, Clermont, FL 34711
$279,900

2 beds

|

2 baths

|

1,374 sq ft

|

Villa

3632 SOLANA CIR B, CLERMONT, FL, 34711
Community: Heritage Hills
Harbor Hills Country Club 39914 SUNBEAM WAY, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$442,900

3 beds

|

2 baths

|

2,034 sq ft

|

House

39914 SUNBEAM WAY, LADY LAKE, FL, 32159
The Villages® 621 ENCONTO ST, THE VILLAGES, FL, 32159, The Villages, FL 32159
$272,000

2 beds

|

2 baths

|

1,109 sq ft

|

Villa

621 ENCONTO ST, THE VILLAGES, FL, 32159
Community: The Villages®
Grand Haven 6 IBIS CT, PALM COAST, FL, 32137, Palm Coast, FL 32137
$550,000

4 beds

|

2 baths

|

2,276 sq ft

|

House

6 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
The Villages® 3300 BOARDROOM TRL, THE VILLAGES, FL, 32..., The Villages, FL 32163
$999,999

3 beds

|

3 baths

|

2,255 sq ft

|

House

3300 BOARDROOM TRL, THE VILLAGES, FL, 32...
Community: The Villages®
Pennbrooke Fairways 213 WILLOW BROOK DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$194,900

2 beds

|

2 baths

|

816 sq ft

|

House

213 WILLOW BROOK DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Cresswind DeLand 1288 TWIN FARMS CT, DELAND, FL, 32724, Deland, FL 32724
$589,990

2 beds

|

2 baths

|

2,029 sq ft

|

House

1288 TWIN FARMS CT, DELAND, FL, 32724
Community: Cresswind DeLand
Harbor Hills Country Club 5321 GREENS DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$574,900

3 beds

|

2 baths

|

2,948 sq ft

|

House

5321 GREENS DR, LADY LAKE, FL, 32159
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.
Bridgewater at Viera 1794 VELKY LN, MELBOURNE, FL, 32940, Melbourne, FL 32940
$374,900

2 beds

|

2 baths

|

1,565 sq ft

|

House

1794 VELKY LN, MELBOURNE, FL, 32940
The Villages® 1863 W SCHWARTZ BLVD, LADY LAKE, FL, 321..., Lady Lake, FL 32159
$150,000

2 beds

|

2 baths

|

1,442 sq ft

|

Manufactured Home

1863 W SCHWARTZ BLVD, LADY LAKE, FL, 321...
Community: The Villages®
The Villages® 1116 RUSSELL LOOP, THE VILLAGES, FL, 321..., The Villages, FL 32162
$1,275,000

3 beds

|

2 baths

|

2,844 sq ft

|

House

1116 RUSSELL LOOP, THE VILLAGES, FL, 321...
Community: The Villages®
Lake Ashton 4083 ASHTON CLUB DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$535,000

3 beds

|

2 baths

|

2,477 sq ft

|

House

4083 ASHTON CLUB DR, LAKE WALES, FL, 338...
Community: Lake Ashton
The Villages® 1204 FLAMINGO PL, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$499,900

3 beds

|

2 baths

|

1,433 sq ft

|

Villa

1204 FLAMINGO PL, 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
The Villages® 7177 SE 172ND HAZELWOOD LOOP, THE VILLAG..., The Villages, FL 32162
$415,000

3 beds

|

2 baths

|

1,918 sq ft

|

House

7177 SE 172ND HAZELWOOD LOOP, THE VILLAG...
Community: The Villages®
Plantation Bay Golf & Country Club 39 MAGNOLIA DR 39, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$274,900

2 beds

|

2 baths

|

1,300 sq ft

|

Condo

39 MAGNOLIA DR 39, ORMOND BEACH, FL, 321...
Del Webb Sunbridge 2707 RIVER CREEK LN, ST CLOUD, FL, 34769, St Cloud, FL 34769
$529,000

2 beds

|

2 baths

|

1,670 sq ft

|

House

2707 RIVER CREEK LN, ST CLOUD, FL, 34769
Community: Del Webb Sunbridge
Plantation Bay Golf & Country Club 209 HEATHERWOOD CT, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174
$689,900

3 beds

|

3 baths

|

2,402 sq ft

|

House

209 HEATHERWOOD CT, ORMOND BEACH, FL, 32...
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.
Carillon Lakes 3891 WHISTLEWOOD CIR, LAKELAND, FL, 3381..., Lakeland, FL 33811
$310,000

3 beds

|

2 baths

|

1,758 sq ft

|

House

3891 WHISTLEWOOD CIR, LAKELAND, FL, 3381...
Community: Carillon Lakes
Traditions at Lake Ruby 3588 RALEIGH DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$274,995

2 beds

|

2 baths

|

1,719 sq ft

|

House

3588 RALEIGH DR, WINTER HAVEN, FL, 33884
Arlington Ridge 4506 SHENANDOAH RIVER TRL, LEESBURG, FL,..., Leesburg, FL 34748
$354,900

3 beds

|

2 baths

|

1,711 sq ft

|

House

4506 SHENANDOAH RIVER TRL, LEESBURG, FL,...
Community: Arlington Ridge
The Villages® 2610 LINDEWOOD ST, THE VILLAGES, FL, 321..., The Villages, FL 32163
$385,000

3 beds

|

2 baths

|

1,620 sq ft

|

Villa

2610 LINDEWOOD ST, 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
Stonecrest 11266 SE 170TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$409,999

3 beds

|

2 baths

|

1,987 sq ft

|

House

11266 SE 170TH LN, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Palms at Serenoa 17718 BLAZING STAR CIR, CLERMONT, FL, 34..., Clermont, FL 34714
$425,000

2 beds

|

2 baths

|

1,816 sq ft

|

House

17718 BLAZING STAR CIR, CLERMONT, FL, 34...
Community: Palms at Serenoa

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