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Winter Park, FL 55+ active adult communities & homes for sale - Page 26

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
3.8 rating (6 reviews) Trilogy® Orlando
$200Ks - $600Ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 homes
5 rating (2 reviews) Heritage Isle
$200Ks - $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) 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) Del Webb Sunbridge
$300Ks - $1Ms
Del Webb Sunbridge, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2019 - 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
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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® 1307 GALINDO PL, THE VILLAGES, FL, 32159, The Villages, FL 32159
$345,000

3 beds

|

2 baths

|

1,872 sq ft

|

House

1307 GALINDO PL, THE VILLAGES, FL, 32159
Community: The Villages®
Spruce Creek Country Club 13191 SE 93RD TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491
$305,000

2 beds

|

2 baths

|

1,452 sq ft

|

House

13191 SE 93RD TERRACE RD, SUMMERFIELD, F...
Spruce Creek Country Club 8516 SE 137TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$265,000

2 beds

|

2 baths

|

1,296 sq ft

|

House

8516 SE 137TH LOOP, SUMMERFIELD, FL, 344...
Spruce Creek Country Club 9910 SE 138TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$398,700

3 beds

|

2 baths

|

2,025 sq ft

|

House

9910 SE 138TH LOOP, SUMMERFIELD, FL, 344...
The Villages® 1485 MURRELLS INLET LOOP, THE VILLAGES, ..., The Villages, FL 32162
$328,000

2 beds

|

2 baths

|

1,382 sq ft

|

House

1485 MURRELLS INLET LOOP, THE VILLAGES, ...
Community: The Villages®
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Questions? Call us: (888) 625-4885
Plantation at Leesburg 5042 DESOTO WAY, LEESBURG, FL, 34748, Leesburg, FL 34748
$194,750

2 beds

|

2 baths

|

1,326 sq ft

|

House

5042 DESOTO WAY, LEESBURG, FL, 34748
Plantation at Leesburg 25501 MAUREPAS LN, LEESBURG, FL, 34748, Leesburg, FL 34748
$569,900

2 beds

|

2 baths

|

2,945 sq ft

|

House

25501 MAUREPAS LN, LEESBURG, FL, 34748
Stonecrest 17672 SE 121ST CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$280,000

3 beds

|

2 baths

|

1,911 sq ft

|

House

17672 SE 121ST CT, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Breakaway Trails 45 WINDING CREEK WAY, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174
$614,900

3 beds

|

2 baths

|

2,366 sq ft

|

House

45 WINDING CREEK WAY, ORMOND BEACH, FL, ...
Community: Breakaway Trails
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.
Spruce Creek South 17655 SE 102ND CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$174,000

2 beds

|

2 baths

|

1,008 sq ft

|

House

17655 SE 102ND CIR, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
Venetian Bay 3611 MARISOL CT, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168
$559,000

3 beds

|

2 baths

|

1,712 sq ft

|

House

3611 MARISOL CT, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
Trilogy® Orlando 615 CONSERVATION BLVD, GROVELAND, FL, 34..., Groveland, FL 34736
$395,000

2 beds

|

3 baths

|

2,009 sq ft

|

House

615 CONSERVATION BLVD, GROVELAND, FL, 34...
Community: Trilogy® Orlando
Grand Haven 200 RIVERFRONT DR D201, PALM COAST, FL, ..., Palm Coast, FL 32137
$575,000

3 beds

|

3 baths

|

2,167 sq ft

|

Condo

200 RIVERFRONT DR D201, PALM COAST, FL, ...
Community: Grand Haven
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Spruce Creek Country Club 12176 SE 91ST AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$328,000

3 beds

|

2 baths

|

2,120 sq ft

|

House

12176 SE 91ST AVE, SUMMERFIELD, FL, 3449...
Bridgewater at Viera 9704 ALISTER DR, MELBOURNE, FL, 32940, Melbourne, FL 32940
$535,000

2 beds

|

2 baths

|

1,876 sq ft

|

House

9704 ALISTER DR, MELBOURNE, FL, 32940
Plantation Bay Golf & Country Club 645 ELK RIVER DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$439,000

3 beds

|

2 baths

|

1,762 sq ft

|

House

645 ELK RIVER DR, ORMOND BEACH, FL, 3217...
Sandpiper Golf & Country Club 6054 CRANE DR, LAKELAND, FL, 33809, Lakeland, FL 33809
$335,000

3 beds

|

2 baths

|

1,915 sq ft

|

House

6054 CRANE DR, LAKELAND, FL, 33809
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.
Latitude Margaritaville 279 LATITUDE DR, DAYTONA BEACH, FL, 3212..., Daytona Beach, FL 32124
$419,900

2 beds

|

2 baths

|

1,205 sq ft

|

House

279 LATITUDE DR, DAYTONA BEACH, FL, 3212...
The Villages® 852 SAPPHIRE PL, THE VILLAGES, FL, 32163, The Villages, FL 32163
$355,000

3 beds

|

2 baths

|

1,407 sq ft

|

Villa

852 SAPPHIRE PL, THE VILLAGES, FL, 32163
Community: The Villages®
Del Webb Orlando 280 DEL SOL AVE, DAVENPORT, FL, 33837, Davenport, FL 33837
$474,000

3 beds

|

2 baths

|

2,365 sq ft

|

House

280 DEL SOL AVE, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Heritage - The Cottages of Sanders Grove 6342 SANDERS GROVE CIR, OKAHUMPKA, FL, 3..., Okahumpka, FL 34762
$314,900

3 beds

|

2 baths

|

1,788 sq ft

|

House

6342 SANDERS GROVE CIR, OKAHUMPKA, FL, 3...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Venetian Bay 2820 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$442,500

3 beds

|

3 baths

|

2,203 sq ft

|

Townhouse

2820 ISLES WAY, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
Spruce Creek Country Club 13324 SE 91ST COURT RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$408,000

3 beds

|

2 baths

|

1,870 sq ft

|

House

13324 SE 91ST COURT RD, SUMMERFIELD, FL,...
Del Webb Orlando 333 ALMANSA ST, DAVENPORT, FL, 33837, Davenport, FL 33837
$354,900

2 beds

|

2 baths

|

1,655 sq ft

|

House

333 ALMANSA ST, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Lake Ashton 4063 BIRKDALE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$300,000

2 beds

|

2 baths

|

1,530 sq ft

|

House

4063 BIRKDALE DR, LAKE WALES, FL, 33859
Community: Lake Ashton
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® 870 TREVINO TER, THE VILLAGES, FL, 32159, The Villages, FL 32159
$315,000

2 beds

|

2 baths

|

1,087 sq ft

|

Villa

870 TREVINO TER, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 3349 COUNTRYSIDE PATH, THE VILLAGES, FL,..., The Villages, FL 32163
$385,000

3 beds

|

2 baths

|

1,855 sq ft

|

House

3349 COUNTRYSIDE PATH, THE VILLAGES, FL,...
Community: The Villages®
Sandpiper Golf & Country Club 669 EAGLE RUN, LAKELAND, FL, 33809, Lakeland, FL 33809
$285,000

2 beds

|

2 baths

|

1,321 sq ft

|

House

669 EAGLE RUN, LAKELAND, FL, 33809
Latitude Margaritaville 613 GOOD LIFE WAY, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124
$345,000

2 beds

|

2 baths

|

1,204 sq ft

|

House

613 GOOD LIFE WAY, DAYTONA BEACH, FL, 32...
Stonecrest 11108 SE 170TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$595,000

3 beds

|

2 baths

|

2,195 sq ft

|

House

11108 SE 170TH PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
New Latitude Margaritaville 745 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$619,900

2 beds

|

2 baths

|

1,922 sq ft

|

House

745 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...
Trilogy® Orlando 602 CONSERVATION BLVD, GROVELAND, FL, 34..., Groveland, FL 34736
$589,999

2 beds

|

3 baths

|

1,900 sq ft

|

House

602 CONSERVATION BLVD, GROVELAND, FL, 34...
Community: Trilogy® Orlando
Bridgewater at Viera 2183 GREAT BELT CIR, MELBOURNE, FL, 3294..., Melbourne, FL 32940
$619,000

3 beds

|

4 baths

|

2,390 sq ft

|

House

2183 GREAT BELT CIR, MELBOURNE, FL, 3294...
Stonecrest 16896 SE 110TH COURT RD, SUMMERFIELD, FL..., Summerfield, FL 34491
$381,000

3 beds

|

2 baths

|

1,951 sq ft

|

House

16896 SE 110TH COURT RD, SUMMERFIELD, FL...
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.
Stonecrest 11396 SE 178TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$357,000

3 beds

|

3 baths

|

1,735 sq ft

|

Villa

11396 SE 178TH PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Spruce Creek Country Club 9811 SE 138TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$325,000

2 beds

|

2 baths

|

1,858 sq ft

|

House

9811 SE 138TH LOOP, SUMMERFIELD, FL, 344...
Trilogy® Orlando 251 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736
$419,000

2 beds

|

2 baths

|

1,900 sq ft

|

House

251 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
Heritage Isle 3029 VALLEJO WAY, MELBOURNE, FL, 32940, Melbourne, FL 32940
$328,200

2 beds

|

2 baths

|

1,532 sq ft

|

Townhouse

3029 VALLEJO WAY, MELBOURNE, FL, 32940
Community: Heritage Isle
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Stonecrest 17414 SE 123RD TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$355,000

3 beds

|

2 baths

|

1,914 sq ft

|

House

17414 SE 123RD TER, SUMMERFIELD, FL, 344...
Community: Stonecrest
The Villages® 1208 TARPON LN, THE VILLAGES, FL, 32159, The Villages, FL 32159
$264,500

2 beds

|

2 baths

|

1,583 sq ft

|

House

1208 TARPON LN, THE VILLAGES, FL, 32159
Community: The Villages®

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2,398 homes
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