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Leesburg, FL 55+ active adult communities & homes for sale - Page 6

Living in Leesburg

Homebuyers looking for 55+ communities in Leesburg will enjoy this small Central Florida city. Located just 45 miles northwest of Orlando it is the oldest city in Lake County.…

Homebuyers looking for 55+ communities in Leesburg will enjoy this small Central Florida city. Located just 45 miles northwest of Orlando it is the oldest city in Lake County. Residents enjoy a variety of entertainment and outdoor recreation as well as Florida's tax friendly economy.

Leesburg Climate & Geography

For some residents, one of the perks of living in Florida is the lack of snowfall and high temperatures. However, Leesburg is a prime location for retirees who still enjoy some seasonal variation. While the city’s drier season lasts for most of the year, rainfall, humidity, and water temperature do vary. Summers are typically hot, wet, and humid while winters are dry and warm.

Recreation, Culture & Entertainment In Leesburg

Leesburg's sunny weather is perfect for exploring the multiple nature parks in the area. Popular parks include Venetians Gardens Park, Herlong Park, Flat Island Preserve, and Emeralda Marsh Conserve. 

Favorite indoor activities include the Cane Garden Country Club, Eisenhower Regional Recreation Center, and Savannah Center. In addition the Melon Patch Theatre, and Tropic Theater are located in Leesburg and offer a variety of entertainment.

Once a year, Leesburg hosts the world’s largest motorcycle and music event, the Leesburg Bikefest. This event lasts for three days and is loaded with concerts, vendors, bike shows, and more.

Leesburg Cost of Living & Taxes

Florida is ranked as one of the top 10 most tax-friendly states for retirees. Retirement benefits and Social Security income are not taxed. Moreover Florida residents 65 and older who meet certain requirements receive a tax break on property taxes.

While the overall cost of living in Leesburg is lower than the state average, the sales tax is one percent higher. The cost of living for a resident of Leesburg is 6.2 percent lower than the national average while other cities such as Orlando and Jacksonville are higher than the average. The costs of health care, groceries, housing, and transportation all contribute to the city’s lower cost of living when compared to the state average.

Health Care in Leesburg

Both the Leesburg Regional Medical Center and LifeStream Behavioral Center are located in Leesburg. Additionally, AdventHealth Waterman, Villages Regional Hospital, and South Lake Hospital are within 20 miles of Leesburg. The Leesburg Regional Medical Center is recognized as No. 3 in Central Florida. The medical center ranks as a high performing facility in chronic obstructive pulmonary disease, heart failure and bypass surgery, and knee replacements.

Frequently Asked Questions


1,145 homes near Leesburg

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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
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
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 (8 reviews) Royal Highlands
$200ks - $400ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
5 rating (8 reviews) Kings Ridge
$200ks - $400ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 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 (1 reviews) Royal Harbor
$200ks - $800ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 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
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
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 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
Scottish Highlands
$100ks - $200ks
Scottish Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1983 - 1992 | 653 homes
4.8 rating (6 reviews) Highland Lakes
$100ks - $200ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
Heritage - The Cottages o...
$300ks
Heritage - The Cottages o..., Okahumpka, FL
New Construction | 55+ age-restricted | Built 2022 - present | 179 homes
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
Lakeside Landings
$100ks - $300ks
Lakeside Landings, Oxford, FL
New and Resale | Age-targeted | Built 2005 - present | 700 homes
Esplanade at McKinnon Gro...
$300ks - $900ks
Esplanade at McKinnon Gro..., Winter Garden, FL
New Construction | Age-targeted | Built 2024 - present | 658 homes
5 rating (1 reviews) Esplanade at Highland Ran...
$300ks - $600ks
Esplanade at Highland Ran..., Clermont, FL
Resale Only | 55+ age-restricted | Built 2014 - 2022 | 475 homes
Del Webb Minneola
$400ks - $700ks
Del Webb Minneola, Minneola, FL
New Construction | 55+ age-restricted | Built 2020 - present
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.
3.9 rating (7 reviews) Summit Greens
$300ks - $400ks
Summit Greens, Clermont, FL
Resale Only | 55+ age-restricted | Built 2001 - 2019 | 769 homes
Summit Chase Villas
$100ks
Summit Chase Villas, Tavares, FL
Resale Only | 55+ age-restricted | Built 1982 - 1989 | 60 homes
Cresswind at Hammock Oaks
$300ks - $500ks
Cresswind at Hammock Oaks, Lady Lake, FL
New and Resale | 55+ age-restricted | Built 2024 - 2025 | 141 homes
Baytree
$100ks - $300ks
Baytree, Tavares, FL
Resale Only | 55+ age-restricted | Built 1990 - 2003 | 221 homes
Cresswind at Lake Harris
$300ks - $500ks
Cresswind at Lake Harris, Tavares, FL
New Construction | 55+ age-restricted | Built 2025 - present | 625 homes
Esplanade at McKinnon Groves 11232 CARDING MILL LN, WINTER GARDEN, FL..., Winter Garden, FL 34787
$690,000

3 beds

|

3 baths

|

1,843 sq ft

|

House

11232 CARDING MILL LN, WINTER GARDEN, FL...
Kings Ridge 3613 WESTERHAM DR, CLERMONT, FL, 34711, Clermont, FL 34711
$350,000

2 beds

|

2 baths

|

1,441 sq ft

|

House

3613 WESTERHAM DR, CLERMONT, FL, 34711
Community: Kings Ridge
The Villages® 8305 SE 168TH MARDELL LN, THE VILLAGES, ..., The Villages, FL 32162
$388,876

3 beds

|

2 baths

|

1,766 sq ft

|

House

8305 SE 168TH MARDELL LN, THE VILLAGES, ...
Community: The Villages®
The Villages® 560 KIMBERLY ST, THE VILLAGES, FL, 32163, The Villages, FL 32163
$345,000

2 beds

|

2 baths

|

1,266 sq ft

|

Villa

560 KIMBERLY ST, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 1302 LA ESTRELLITA WAY, THE VILLAGES, FL..., The Villages, FL 32162
$550,000

3 beds

|

2 baths

|

2,197 sq ft

|

House

1302 LA ESTRELLITA WAY, THE VILLAGES, FL...
Community: The Villages®
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
The Villages® 1524 CERVANTES PL, THE VILLAGES, FL, 321..., The Villages, FL 32159
$725,000

3 beds

|

2 baths

|

2,286 sq ft

|

House

1524 CERVANTES PL, THE VILLAGES, FL, 321...
Community: The Villages®
The Villages® 349 PACOLET TER, THE VILLAGES, FL, 32162, The Villages, FL 32162
$555,000

3 beds

|

3 baths

|

2,043 sq ft

|

House

349 PACOLET TER, THE VILLAGES, FL, 32162
Community: The Villages®
Stonecrest 11375 SE 175TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$269,900

3 beds

|

2 baths

|

1,607 sq ft

|

House

11375 SE 175TH LN, SUMMERFIELD, FL, 3449...
Community: Stonecrest
The Villages® 2084 NORDIC LN, THE VILLAGES, FL, 32163, The Villages, FL 32163
$769,900

3 beds

|

2 baths

|

1,956 sq ft

|

House

2084 NORDIC LN, THE VILLAGES, FL, 32163
Community: The Villages®
Spruce Creek South 17929 SE 107TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$229,900

2 beds

|

2 baths

|

1,356 sq ft

|

House

17929 SE 107TH CT, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
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® 1457 SOTHELL ST, THE VILLAGES, FL, 32162, The Villages, FL 32162
$299,000

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

1457 SOTHELL ST, THE VILLAGES, FL, 32162
Community: The Villages®
Plantation at Leesburg 24445 MADEWOOD AVE, LEESBURG, FL, 34748, Leesburg, FL 34748
$357,000

2 beds

|

2 baths

|

2,051 sq ft

|

House

24445 MADEWOOD AVE, LEESBURG, FL, 34748
The Villages® 3075 LICCIARDELLO PATH, THE VILLAGES, FL..., The Villages, FL 32163
$795,000

3 beds

|

3 baths

|

1,905 sq ft

|

House

3075 LICCIARDELLO PATH, THE VILLAGES, FL...
Community: The Villages®
The Villages® 728 PRADO DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$239,000

2 beds

|

2 baths

|

1,144 sq ft

|

Manufactured Home

728 PRADO DR, LADY LAKE, FL, 32159
Community: The Villages®
Cindy Certified
3292 WINDBEAM CT, WINTER GARDEN, FL, 347..., Winter Garden, FL 34787
$899,000

3 beds

|

4 baths

|

2,872 sq ft

|

House

3292 WINDBEAM CT, WINTER GARDEN, FL, 347...
Heritage Hills 2819 MAYPORT ST, CLERMONT, FL, 34711, Clermont, FL 34711
$485,000

3 beds

|

2 baths

|

2,194 sq ft

|

House

2819 MAYPORT ST, CLERMONT, FL, 34711
Community: Heritage Hills
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
Kings Ridge 2109 GRAFTON AVE, CLERMONT, FL, 34711, Clermont, FL 34711
$369,000

2 beds

|

2 baths

|

2,031 sq ft

|

House

2109 GRAFTON AVE, CLERMONT, FL, 34711
Community: Kings Ridge
The Villages® 1398 SHOREWOOD ST, THE VILLAGES, FL, 321..., The Villages, FL 32162
$600,000

3 beds

|

2 baths

|

2,287 sq ft

|

House

1398 SHOREWOOD ST, THE VILLAGES, FL, 321...
Community: The Villages®
Summit Greens 1176 MESA VERDE CT, CLERMONT, FL, 34711, Clermont, FL 34711
$335,000

2 beds

|

2 baths

|

1,422 sq ft

|

House

1176 MESA VERDE CT, CLERMONT, FL, 34711
Community: Summit Greens
Del Webb Minneola 1323 ORANGE VALLEY RD, MINNEOLA, FL, 347..., Minneola, FL 34715
$579,000

2 beds

|

2 baths

|

1,737 sq ft

|

House

1323 ORANGE VALLEY RD, MINNEOLA, FL, 347...
Community: Del Webb Minneola
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® 928 EASTMONT CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$385,000

3 beds

|

2 baths

|

1,623 sq ft

|

House

928 EASTMONT CT, THE VILLAGES, FL, 32162
Community: The Villages®
Stonecrest 11268 SE 175TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$230,000

2 beds

|

2 baths

|

1,560 sq ft

|

House

11268 SE 175TH LN, SUMMERFIELD, FL, 3449...
Community: Stonecrest
The Villages® 1624 TAMPICO PL, THE VILLAGES, FL, 32159, The Villages, FL 32159
$299,900

2 beds

|

2 baths

|

1,198 sq ft

|

Villa

1624 TAMPICO PL, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 17632 SE 92ND GRANTHAM TER, THE VILLAGES..., The Villages, FL 32162
$269,000

2 beds

|

2 baths

|

1,148 sq ft

|

House

17632 SE 92ND GRANTHAM TER, THE VILLAGES...
Community: The Villages®
Harbor Hills Country Club 6043 APEX WAY, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$780,000

4 beds

|

3 baths

|

2,615 sq ft

|

House

6043 APEX WAY, LADY LAKE, FL, 32159
Highland Lakes 5440 ROSEWALL CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$229,900

2 beds

|

2 baths

|

1,210 sq ft

|

Villa

5440 ROSEWALL CIR, LEESBURG, FL, 34748
Community: Highland Lakes
Scottish Highlands 1032 SCOTCH PINE CT, LEESBURG, FL, 34788, Leesburg, FL 34788
$239,900

3 beds

|

2 baths

|

1,685 sq ft

|

House

1032 SCOTCH PINE CT, LEESBURG, FL, 34788
Community: Scottish Highlands
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
Lakeside Landings 5310 BOWLINE CT 1, OXFORD, FL, 34484, Oxford, FL 34484
$214,900

2 beds

|

2 baths

|

1,281 sq ft

|

Condo

5310 BOWLINE CT 1, OXFORD, FL, 34484
Community: Lakeside Landings
Kings Ridge 3810 SCARBOROUGH CT, CLERMONT, FL, 34711, Clermont, FL 34711
$435,000

3 beds

|

2 baths

|

1,996 sq ft

|

House

3810 SCARBOROUGH CT, CLERMONT, FL, 34711
Community: Kings Ridge
The Villages® 1645 HOLLOW BRANCH WAY, THE VILLAGES, FL..., The Villages, FL 32162
$565,000

3 beds

|

2 baths

|

1,927 sq ft

|

House

1645 HOLLOW BRANCH WAY, THE VILLAGES, FL...
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 3916 MANOR OAKS CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$299,900

2 beds

|

2 baths

|

1,617 sq ft

|

House

3916 MANOR OAKS CT, LEESBURG, FL, 34748
The Villages® 920 SILVER OAK AVE, THE VILLAGES, FL, 32..., The Villages, FL 32159
$205,000

2 beds

|

2 baths

|

1,344 sq ft

|

Manufactured Home

920 SILVER OAK AVE, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 1800 ST JAMES CIR, THE VILLAGES, FL, 321..., The Villages, FL 32162
$1,749,000

3 beds

|

3 baths

|

3,591 sq ft

|

House

1800 ST JAMES CIR, THE VILLAGES, FL, 321...
Community: The Villages®
The Villages® 16969 SE 92ND PELHAM AVE, THE VILLAGES, ..., The Villages, FL 32162
$335,000

3 beds

|

2 baths

|

1,717 sq ft

|

House

16969 SE 92ND PELHAM AVE, THE VILLAGES, ...
Community: The Villages®
The Villages® 1232 CABELLA CIR, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$440,000

3 beds

|

2 baths

|

2,146 sq ft

|

House

1232 CABELLA CIR, THE VILLAGES, FL, 3215...
Community: The Villages®
Stonecrest 17031 SE 115TH TERRACE RD, SUMMERFIELD, ..., Summerfield, FL 34491
$355,000

3 beds

|

2 baths

|

1,925 sq ft

|

House

17031 SE 115TH TERRACE RD, SUMMERFIELD, ...
Community: Stonecrest
The Villages® 1110 EBLING LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$579,000

3 beds

|

3 baths

|

1,977 sq ft

|

House

1110 EBLING LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
Spruce Creek South 17870 SE 107TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$215,000

2 beds

|

2 baths

|

1,150 sq ft

|

House

17870 SE 107TH TER, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
The Villages® 2573 EDENVILLE PATH, THE VILLAGES, FL, 3..., The Villages, FL 32162
$330,000

3 beds

|

2 baths

|

1,468 sq ft

|

House

2573 EDENVILLE PATH, THE VILLAGES, FL, 3...
Community: The Villages®
Legacy of Leesburg 26939 HONEYMOON AVE, LEESBURG, FL, 34748, Leesburg, FL 34748
$395,000

3 beds

|

2 baths

|

2,002 sq ft

|

House

26939 HONEYMOON AVE, LEESBURG, FL, 34748
Community: Legacy of Leesburg
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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1,145 homes
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