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Leesburg, FL 55+ active adult communities & homes for sale - Page 7

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
The Villages® 2798 CHURCHILL DOWNS, THE VILLAGES, FL, ..., The Villages, FL 32162
$389,900

2 beds

|

2 baths

|

1,537 sq ft

|

House

2798 CHURCHILL DOWNS, THE VILLAGES, FL, ...
Community: The Villages®
The Villages® 912 HUBBARD LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$699,900

3 beds

|

2 baths

|

2,033 sq ft

|

House

912 HUBBARD LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 816 BEECHWOOD AVE, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$119,900

2 beds

|

1 baths

|

672 sq ft

|

Manufactured Home

816 BEECHWOOD AVE, LADY LAKE, FL, 32159
Community: The Villages®
The Villages® 1802 ESTAFANA WAY, THE VILLAGES, FL, 321..., The Villages, FL 32159
$799,000

3 beds

|

4 baths

|

2,317 sq ft

|

House

1802 ESTAFANA WAY, THE VILLAGES, FL, 321...
Community: The Villages®
The Villages® 1897 HARTFORD PATH, THE VILLAGES, FL, 32..., The Villages, FL 32162
$995,000

3 beds

|

2 baths

|

3,100 sq ft

|

House

1897 HARTFORD PATH, THE VILLAGES, FL, 32...
Community: The Villages®
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
Plantation at Leesburg 24817 RIVERBOAT BND, LEESBURG, FL, 34748, Leesburg, FL 34748
$290,000

3 beds

|

2 baths

|

1,747 sq ft

|

House

24817 RIVERBOAT BND, LEESBURG, FL, 34748
Plantation at Leesburg 25524 BELLE HELENE, LEESBURG, FL, 34748, Leesburg, FL 34748
$180,000

2 beds

|

2 baths

|

1,352 sq ft

|

Manufactured Home

25524 BELLE HELENE, LEESBURG, FL, 34748
The Villages® 1454 SAN CLEMENTE CT, THE VILLAGES, FL, ..., The Villages, FL 32159
$798,000

3 beds

|

2 baths

|

2,174 sq ft

|

House

1454 SAN CLEMENTE CT, THE VILLAGES, FL, ...
Community: The Villages®
Pennbrooke Fairways 642 GLEN OAKS DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$247,500

2 beds

|

2 baths

|

1,632 sq ft

|

House

642 GLEN OAKS DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
The Villages® 481 HILDALGO DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$235,000

2 beds

|

2 baths

|

1,121 sq ft

|

Villa

481 HILDALGO DR, THE VILLAGES, FL, 32159
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.
Kings Ridge 3635 KINGSWOOD CT, CLERMONT, FL, 34711, Clermont, FL 34711
$385,000

2 beds

|

2 baths

|

1,661 sq ft

|

House

3635 KINGSWOOD CT, CLERMONT, FL, 34711
Community: Kings Ridge
The Villages® 5870 FLINT LOOP, THE VILLAGES, FL, 32163, The Villages, FL 32163
$765,000

3 beds

|

2 baths

|

2,051 sq ft

|

House

5870 FLINT LOOP, THE VILLAGES, FL, 32163
Community: The Villages®
Legacy of Leesburg 5811 GREENBRIAR LOOP, LEESBURG, FL, 3474..., Leesburg, FL 34748
$340,000

2 beds

|

2 baths

|

1,665 sq ft

|

House

5811 GREENBRIAR LOOP, LEESBURG, FL, 3474...
Community: Legacy of Leesburg
The Villages® 3003 MONUMENT WAY, THE VILLAGES, FL, 321..., The Villages, FL 32163
$597,000

3 beds

|

2 baths

|

1,535 sq ft

|

House

3003 MONUMENT WAY, THE VILLAGES, FL, 321...
Community: The Villages®
Scottish Highlands 1113 BEN HOPE DR, LEESBURG, FL, 34788, Leesburg, FL 34788
$192,900

2 beds

|

2 baths

|

1,089 sq ft

|

House

1113 BEN HOPE DR, LEESBURG, FL, 34788
Community: Scottish Highlands
The Villages® 2224 MARGARITA DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$429,000

3 beds

|

2 baths

|

1,932 sq ft

|

House

2224 MARGARITA DR, THE VILLAGES, FL, 321...
Community: The Villages®
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
The Villages® 1311 TRINIDAD CT, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$359,000

3 beds

|

2 baths

|

1,457 sq ft

|

House

1311 TRINIDAD CT, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 5672 GRIMES CT, THE VILLAGES, FL, 32163, The Villages, FL 32163
$429,900

3 beds

|

2 baths

|

1,791 sq ft

|

Villa

5672 GRIMES CT, THE VILLAGES, FL, 32163
Community: The Villages®
Scottish Highlands 2008 TWEED CT, LEESBURG, FL, 34788, Leesburg, FL 34788
$205,000

3 beds

|

2 baths

|

1,314 sq ft

|

House

2008 TWEED CT, LEESBURG, FL, 34788
Community: Scottish Highlands
Stonecrest 17739 SE 121ST TERRACE RD, SUMMERFIELD, ..., Summerfield, FL 34491
$378,900

2 beds

|

2 baths

|

1,572 sq ft

|

House

17739 SE 121ST TERRACE RD, SUMMERFIELD, ...
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.
Kings Ridge 3805 DOUNE WAY, CLERMONT, FL, 34711, Clermont, FL 34711
$295,000

2 beds

|

2 baths

|

1,091 sq ft

|

House

3805 DOUNE WAY, CLERMONT, FL, 34711
Community: Kings Ridge
Spruce Creek South 17978 SE 104TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$237,900

2 beds

|

2 baths

|

1,356 sq ft

|

House

17978 SE 104TH TER, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
The Villages® 484 AINTREE LN, THE VILLAGES, FL, 32162, The Villages, FL 32162
$329,247

2 beds

|

2 baths

|

1,120 sq ft

|

Villa

484 AINTREE LN, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 2304 WHISPER ST, THE VILLAGES, FL, 32162, The Villages, FL 32162
$315,000

2 beds

|

2 baths

|

1,188 sq ft

|

Villa

2304 WHISPER ST, THE VILLAGES, FL, 32162
Community: The Villages®
Royal Harbor 5596 FREEPORT DR, TAVARES, FL, 32778, Tavares, FL 32778
$280,000

3 beds

|

2 baths

|

1,655 sq ft

|

House

5596 FREEPORT DR, TAVARES, FL, 32778
Community: Royal Harbor
Legacy of Leesburg 5138 AURORA DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$299,900

2 beds

|

2 baths

|

1,856 sq ft

|

House

5138 AURORA DR, LEESBURG, FL, 34748
Community: Legacy of Leesburg
The Villages® 5459 THOME LOOP, THE VILLAGES, FL, 32163, The Villages, FL 32163
$1,711,021

3 beds

|

2 baths

|

2,106 sq ft

|

House

5459 THOME LOOP, THE VILLAGES, FL, 32163
Community: The Villages®
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
Spruce Creek South 10190 SE 178TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$229,999

2 beds

|

2 baths

|

1,008 sq ft

|

House

10190 SE 178TH ST, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
The Villages® 8053 SE 171ST MCALPIN ST, THE VILLAGES, ..., The Villages, FL 32162
$399,000

3 beds

|

2 baths

|

1,879 sq ft

|

House

8053 SE 171ST MCALPIN ST, THE VILLAGES, ...
Community: The Villages®
Highland Lakes 5500 LAVER ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$234,900

3 beds

|

2 baths

|

1,591 sq ft

|

House

5500 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.
Pennbrooke Fairways 439 GRAND VISTA TRL, LEESBURG, FL, 34748, Leesburg, FL 34748
$315,000

3 beds

|

2 baths

|

1,869 sq ft

|

House

439 GRAND VISTA TRL, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
The Villages® 2940 GULLEY LN, THE VILLAGES, FL, 32163, The Villages, FL 32163
$450,000

3 beds

|

2 baths

|

1,525 sq ft

|

House

2940 GULLEY LN, THE VILLAGES, FL, 32163
Community: The Villages®
Scottish Highlands 62 ABERDEEN CIR, LEESBURG, FL, 34788, Leesburg, FL 34788
$225,000

2 beds

|

2 baths

|

1,152 sq ft

|

Condo

62 ABERDEEN CIR, LEESBURG, FL, 34788
Community: Scottish Highlands
The Villages® 1102 ALLAIRE LOOP, THE VILLAGES, FL, 321..., The Villages, FL 32163
$799,900

3 beds

|

2 baths

|

2,000 sq ft

|

House

1102 ALLAIRE LOOP, THE VILLAGES, FL, 321...
Community: The Villages®
The Villages® 2902 CHELTENHAM CT, THE VILLAGES, FL, 32..., The Villages, FL 32162
$425,000

3 beds

|

2 baths

|

1,590 sq ft

|

House

2902 CHELTENHAM CT, THE VILLAGES, FL, 32...
Community: The Villages®
Cindy Certified
2812 DOOLITTLE ST, TAVARES, FL, 32778, Tavares, FL 32778
$359,990

4 beds

|

2 baths

|

1,625 sq ft

|

House

2812 DOOLITTLE ST, TAVARES, FL, 32778
Cindy Certified
2914 SUPERMARINE RD, TAVARES, FL, 32778, Tavares, FL 32778
$366,990

4 beds

|

2 baths

|

1,938 sq ft

|

House

2914 SUPERMARINE RD, TAVARES, FL, 32778
Cindy Certified
2962 SUPERMARINE RD, TAVARES, FL, 32778, Tavares, FL 32778
$364,990

4 beds

|

2 baths

|

1,938 sq ft

|

House

2962 SUPERMARINE RD, TAVARES, FL, 32778
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
The Villages® 3000 SANDY LN, THE VILLAGES, FL, 32162, The Villages, FL 32162
$425,000

3 beds

|

2 baths

|

2,044 sq ft

|

House

3000 SANDY LN, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 2218 LEWISTON LN, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$299,000

3 beds

|

2 baths

|

1,240 sq ft

|

House

2218 LEWISTON LN, THE VILLAGES, FL, 3216...
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.

Frequently Asked Questions


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1,145 homes
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