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Winter Park, FL 55+ active adult communities & homes for sale - Page 41

2,698 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
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
Venetian Bay
$300ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 homes
Want to learn more about 55+ communities in Winter Park? 55places can help!
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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
5 rating (3 reviews) Stonecrest
$200ks - $500ks
Stonecrest, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 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) Twin Lakes
$200ks - $600ks
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
Pelican Bay Daytona Beach
$100ks - $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 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
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 (3 reviews) Lake Ashton
$200ks - $500ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes
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 (8 reviews) Kings Ridge
$200ks - $400ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 homes
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Questions? Call us: (888) 625-4885
Halifax Plantation
$300ks - $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale | Age-targeted | Built 1980 - present | 1,000 homes
5 rating (1 reviews) Cresswind at Victoria Gar...
$300ks - $500ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 homes
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
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
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.
2.8 rating (6 reviews) Arlington Ridge
$200ks - $500ks
Arlington Ridge, Leesburg, FL
New and Resale | 55+ age-restricted | Built 2005 - present | 629 homes
5 rating (1 reviews) Royal Harbor
$200ks - $800ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes
5 rating (8 reviews) Pennbrooke Fairways
<$100k - $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 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
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
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
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
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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
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
Four Seasons at Orlando
$300ks - $600ks
Four Seasons at Orlando, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2017 - present | 557 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.
Heritage - The Cottages o...
$300ks
Heritage - The Cottages o..., Okahumpka, FL
New Construction | 55+ age-restricted | Built 2022 - present | 179 homes
4.8 rating (6 reviews) Highland Lakes
$100ks - $200ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
Breakaway Trails
$400ks - $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 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
Gatherings of Lake Nona
$300ks - $400ks
Gatherings of Lake Nona, Orlando, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 216 homes
Highland Fairways
$100ks - $300ks
Highland Fairways, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1983 - 1998 | 660 homes
Del Webb at Viera
$400ks - $1Ms
Del Webb at Viera, Melbourne, FL
New Construction | 55+ age-restricted | Built 2021 - present | 1,300 homes
Lakeside Landings
$100ks - $300ks
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!
Questions? Call us: (888) 625-4885
The Lakes at Harmony
$200ks - $400ks
The Lakes at Harmony, Harmony, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 400 homes
1 rating (1 reviews) Sullivan Ranch
$200ks - $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 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.
12...3
Royal Harbor 6170 SAILBOAT AVE, TAVARES, FL, 32778, Tavares, FL 32778
$346,000

3 beds

|

2 baths

|

1,535 sq ft

|

House

6170 SAILBOAT AVE, TAVARES, FL, 32778
Community: Royal Harbor
Trilogy® Orlando 290 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736
$589,900

2 beds

|

3 baths

|

2,315 sq ft

|

House

290 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
Twin Lakes 2447 YELLOW BRICK RD, ST CLOUD, FL, 3477..., St Cloud, FL 34772
$305,000

2 beds

|

2 baths

|

1,464 sq ft

|

Villa

2447 YELLOW BRICK RD, ST CLOUD, FL, 3477...
Community: Twin Lakes
Solivita 501 HERITAGE TRAIL ST, POINCIANA, FL, 34..., Poinciana, FL 34759
$295,000

2 beds

|

2 baths

|

1,574 sq ft

|

House

501 HERITAGE TRAIL ST, POINCIANA, FL, 34...
Community: Solivita
The Country Club of Mount Dora 8027 SAINT ANDREWS WAY, MOUNT DORA, FL, ..., Mount Dora, FL 32757
$387,000

2 beds

|

2 baths

|

1,678 sq ft

|

House

8027 SAINT ANDREWS WAY, MOUNT DORA, FL, ...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Harbor Hills Country Club 5701 CRESTVIEW DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$529,500

5 beds

|

3 baths

|

2,448 sq ft

|

House

5701 CRESTVIEW DR, LADY LAKE, FL, 32159
Cindy Certified
1183 TURTLE ISLAND RD, LADY LAKE, FL, 32..., Lady Lake, FL 32159
$249,900

3 beds

|

2 baths

|

1,509 sq ft

|

Halfplex

1183 TURTLE ISLAND RD, LADY LAKE, FL, 32...
Cindy Certified
17 FLAGSTICK LN, BUNNELL, FL, 32110, Bunnell, FL 32110
$295,395

3 beds

|

2 baths

|

1,459 sq ft

|

House

17 FLAGSTICK LN, BUNNELL, FL, 32110
Grand Haven 52 SOUTHLAKE DR, PALM COAST, FL, 32137, Palm Coast, FL 32137
$550,000

4 beds

|

2 baths

|

2,443 sq ft

|

House

52 SOUTHLAKE DR, PALM COAST, FL, 32137
Community: Grand Haven
Lakes of Mount Dora 8270 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757
$399,000

3 beds

|

2 baths

|

1,828 sq ft

|

House

8270 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...
Community: Lakes of Mount Dora
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 - The Cottages of Sanders Grove 6217 SANDERS GROVE CIR 1, OKAHUMKA, FL, ..., Okahumka, FL 34762
$363,389

4 beds

|

3 baths

|

1,938 sq ft

|

House

6217 SANDERS GROVE CIR 1, OKAHUMKA, FL, ...
Heritage - The Cottages of Sanders Grove 5715 5715 HIAWASSEE RD, OKAHUMKA, FL, 34..., Okahumka, FL 34762
$349,250

4 beds

|

3 baths

|

1,938 sq ft

|

House

5715 5715 HIAWASSEE RD, OKAHUMKA, FL, 34...
The Lakes at Harmony 3430 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773
$358,990

3 beds

|

2 baths

|

1,876 sq ft

|

House

3430 SAGEBRUSH ST, HARMONY, FL, 34773
Heritage - The Cottages of Sanders Grove 6209 SANDERS GROVE CIR 1, OKAHUMKA, FL, ..., Okahumka, FL 34762
$343,445

4 beds

|

2 baths

|

1,758 sq ft

|

House

6209 SANDERS GROVE CIR 1, OKAHUMKA, FL, ...
The Country Club of Mount Dora 1750 STAFFORD SPRINGS BLVD, MOUNT DORA, ..., Mount Dora, FL 32757
$399,000

2 beds

|

2 baths

|

1,288 sq ft

|

House

1750 STAFFORD SPRINGS BLVD, MOUNT DORA, ...
Heritage - The Cottages of Sanders Grove 6201 SANDERS GROVE CIR 1, OKAHUMKA, FL, ..., Okahumka, FL 34762
$341,535

4 beds

|

2 baths

|

1,625 sq ft

|

House

6201 SANDERS GROVE CIR 1, OKAHUMKA, FL, ...
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Heritage - The Cottages of Sanders Grove 5719 HIAWASSEE RD 1, OKAHUMKA, FL, 34762, Okahumka, FL 34762
$329,990

4 beds

|

2 baths

|

1,625 sq ft

|

House

5719 HIAWASSEE RD 1, OKAHUMKA, FL, 34762
Heritage - The Cottages of Sanders Grove 6213 SANDERS GROVE CIR, OKAHUMKA, FL, 34..., Okahumka, FL 34762
$332,595

4 beds

|

2 baths

|

1,625 sq ft

|

House

6213 SANDERS GROVE CIR, OKAHUMKA, FL, 34...
Heritage - The Cottages of Sanders Grove 6205 SANDERS GROVE CIR 1, OKAHUMKA, FL, ..., Okahumka, FL 34762
$323,286

3 beds

|

2 baths

|

1,407 sq ft

|

House

6205 SANDERS GROVE CIR 1, OKAHUMKA, FL, ...
Heritage - The Cottages of Sanders Grove 5727 HIAWASSEE RD, OKAHUMKA, FL, 34762, Okahumka, FL 34762
$309,990

3 beds

|

2 baths

|

1,407 sq ft

|

House

5727 HIAWASSEE RD, OKAHUMKA, FL, 34762
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.
Cindy Certified
1236 GLENDALE AVE, PALM BAY, FL, 32907, Palm Bay, FL 32907
$334,900

4 beds

|

2 baths

|

2,052 sq ft

|

House

1236 GLENDALE AVE, PALM BAY, FL, 32907
Lake Ashton 4084 STONE CREEK LOOP, LAKE WALES, FL, 3..., Lake Wales, FL 33859
$385,000

3 beds

|

2 baths

|

2,074 sq ft

|

House

4084 STONE CREEK LOOP, LAKE WALES, FL, 3...
Community: Lake Ashton
Tohoqua Reserve 2726 SUMMER RETREAT LN, KISSIMMEE, FL, 3..., Kissimmee, FL 34744
$349,900

3 beds

|

2 baths

|

1,559 sq ft

|

Villa

2726 SUMMER RETREAT LN, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
The Villages® 714 CIMARRON AVE, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$998,500

3 beds

|

2 baths

|

2,774 sq ft

|

House

714 CIMARRON AVE, THE VILLAGES, FL, 3215...
Community: The Villages®
The Villages® 992 RIDGELAND PATH, THE VILLAGES, FL, 32..., The Villages, FL 32162
$425,000

3 beds

|

2 baths

|

1,703 sq ft

|

House

992 RIDGELAND PATH, THE VILLAGES, FL, 32...
Community: The Villages®
Esplanade at Highland Ranch 2612 FRAZEEK CT, CLERMONT, FL, 34715, Clermont, FL 34715
$435,000

3 beds

|

3 baths

|

1,827 sq ft

|

House

2612 FRAZEEK CT, CLERMONT, FL, 34715
Venetian Bay 3364 TORRE BLVD, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168
$420,000

3 beds

|

2 baths

|

1,939 sq ft

|

Halfplex

3364 TORRE BLVD, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Pelican Bay Daytona Beach 348 BOB WHITE CT 7, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32119
$167,000

1 beds

|

1 baths

|

894 sq ft

|

Condo

348 BOB WHITE CT 7, DAYTONA BEACH, FL, 3...
Spruce Creek Country Club 13650 SE 91ST AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$350,000

3 beds

|

2 baths

|

1,870 sq ft

|

House

13650 SE 91ST AVE, SUMMERFIELD, FL, 3449...
The Villages® 2875 RAIN LILY LOOP, THE VILLAGES, FL, 3..., The Villages, FL 32163
$624,000

3 beds

|

2 baths

|

1,965 sq ft

|

House

2875 RAIN LILY LOOP, THE VILLAGES, FL, 3...
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.
Plantation at Leesburg 4438 RIVER RIDGE DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$280,000

2 beds

|

2 baths

|

1,871 sq ft

|

House

4438 RIVER RIDGE DR, LEESBURG, FL, 34748
The Villages® 17946 SE 87TH MELROSE CT, THE VILLAGES, ..., The Villages, FL 32162
$445,000

3 beds

|

2 baths

|

2,013 sq ft

|

House

17946 SE 87TH MELROSE CT, THE VILLAGES, ...
Community: The Villages®
Cindy Certified
26180 FEATHERGRASS CIR, LEESBURG, FL, 34..., Leesburg, FL 34748
$285,000

3 beds

|

2 baths

|

1,432 sq ft

|

House

26180 FEATHERGRASS CIR, LEESBURG, FL, 34...
Colonnades 4976 PLEASANT HOLLOW TRL, LAKELAND, FL, ..., Lakeland, FL 33811
$210,000

2 beds

|

2 baths

|

1,543 sq ft

|

House

4976 PLEASANT HOLLOW TRL, LAKELAND, FL, ...
Community: Colonnades
Cindy Certified
2 PAT PL, PALM COAST, FL, 32164, Palm Coast, FL 32164
$549,900

4 beds

|

3 baths

|

2,675 sq ft

|

House

2 PAT PL, PALM COAST, FL, 32164
The Villages® 2311 GLADE RUN, THE VILLAGES, FL, 32162, The Villages, FL 32162
$490,000

3 beds

|

2 baths

|

1,927 sq ft

|

House

2311 GLADE RUN, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 728 CONGAREE LOOP, THE VILLAGES, FL, 321..., The Villages, FL 32163
$819,900

3 beds

|

3 baths

|

2,829 sq ft

|

House

728 CONGAREE LOOP, THE VILLAGES, FL, 321...
Community: The Villages®
Grand Haven 1 GLENEAGLES PL, PALM COAST, FL, 32137, Palm Coast, FL 32137
$340,000

3 beds

|

2 baths

|

1,488 sq ft

|

House

1 GLENEAGLES PL, 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
Spruce Creek South 17676 SE 102ND CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$279,900

3 beds

|

3 baths

|

1,988 sq ft

|

House

17676 SE 102ND CIR, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
Cindy Certified
740 PREAKNESS CIR, DELAND, FL, 32724, Deland, FL 32724
$369,900

4 beds

|

2 baths

|

2,029 sq ft

|

House

740 PREAKNESS CIR, DELAND, FL, 32724
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.

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2,698 homes
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