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Leesburg, FL 55+ active adult communities & homes for sale - Page 29

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
Cindy Certified
855 SUNSHOWER DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$299,000

4 beds

|

3 baths

|

1,988 sq ft

|

House

855 SUNSHOWER DR, LADY LAKE, FL, 32159
Cindy Certified
851 SUNSHOWER DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$294,000

4 beds

|

2 baths

|

1,840 sq ft

|

House

851 SUNSHOWER DR, LADY LAKE, FL, 32159
Del Webb Minneola 2761 TOP HILL CT, MINNEOLA, FL, 34715, Minneola, FL 34715
$569,900

2 beds

|

2 baths

|

1,943 sq ft

|

House

2761 TOP HILL CT, MINNEOLA, FL, 34715
Community: Del Webb Minneola
Plantation at Leesburg 25119 CRANES ROOST CIR, LEESBURG, FL, 34..., Leesburg, FL 34748
$213,900

2 beds

|

2 baths

|

1,328 sq ft

|

House

25119 CRANES ROOST CIR, LEESBURG, FL, 34...
Cindy Certified
2866 SUPERMARINE RD, TAVARES, FL, 32778, Tavares, FL 32778
$349,990

4 beds

|

2 baths

|

1,758 sq ft

|

House

2866 SUPERMARINE RD, TAVARES, FL, 32778
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
Stonecrest 17435 SE 112TH AVE, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$339,500

3 beds

|

2 baths

|

1,682 sq ft

|

House

17435 SE 112TH AVE, SUMMERFIELD, FL, 344...
Community: Stonecrest
The Villages® 375 SIMPSON ST, THE VILLAGES, FL, 32162, The Villages, FL 32162
$399,900

3 beds

|

2 baths

|

1,887 sq ft

|

House

375 SIMPSON ST, THE VILLAGES, FL, 32162
Community: The Villages®
Kings Ridge 4202 HAMMERSMITH DR, CLERMONT, FL, 34711, Clermont, FL 34711
$389,900

2 beds

|

2 baths

|

1,968 sq ft

|

House

4202 HAMMERSMITH DR, CLERMONT, FL, 34711
Community: Kings Ridge
Royal Highlands 4738 ST ANDREWS ARC, LEESBURG, FL, 34748, Leesburg, FL 34748
$299,999

3 beds

|

2 baths

|

1,892 sq ft

|

House

4738 ST ANDREWS ARC, LEESBURG, FL, 34748
Community: Royal Highlands
Arlington Ridge 3507 ARLINGTON RIDGE BLVD, LEESBURG, FL,..., Leesburg, FL 34748
$289,900

2 beds

|

2 baths

|

1,476 sq ft

|

House

3507 ARLINGTON RIDGE BLVD, LEESBURG, FL,...
Community: Arlington Ridge
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.
Del Webb Minneola 2759 PURPLE MEADOW CT, MINNEOLA, FL, 347..., Minneola, FL 34715
$459,000

2 beds

|

2 baths

|

1,405 sq ft

|

House

2759 PURPLE MEADOW CT, MINNEOLA, FL, 347...
Community: Del Webb Minneola
Legacy of Leesburg 27328 PINE STRAW RD, LEESBURG, FL, 34748, Leesburg, FL 34748
$334,999

3 beds

|

2 baths

|

1,894 sq ft

|

House

27328 PINE STRAW RD, LEESBURG, FL, 34748
Community: Legacy of Leesburg
Cindy Certified
336 FREE RANGE DR, GROVELAND, FL, 34736, Groveland, FL 34736
$499,990

4 beds

|

3 baths

|

2,472 sq ft

|

House

336 FREE RANGE DR, GROVELAND, FL, 34736
Cindy Certified
159 WATERSTONE LOOP, TAVARES, FL, 32778, Tavares, FL 32778
$397,999

4 beds

|

3 baths

|

2,051 sq ft

|

House

159 WATERSTONE LOOP, TAVARES, FL, 32778
Plantation at Leesburg 25800 BELLE HELENE, LEESBURG, FL, 34748, Leesburg, FL 34748
$228,000

3 beds

|

2 baths

|

1,653 sq ft

|

House

25800 BELLE HELENE, LEESBURG, FL, 34748
Plantation at Leesburg 25339 CRESTWATER DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$284,900

3 beds

|

2 baths

|

1,765 sq ft

|

House

25339 CRESTWATER DR, LEESBURG, FL, 34748
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
Royal Highlands 20631 PRINCE RANIER PL, LEESBURG, FL, 34..., Leesburg, FL 34748
$347,900

3 beds

|

2 baths

|

2,070 sq ft

|

House

20631 PRINCE RANIER PL, LEESBURG, FL, 34...
Community: Royal Highlands
Kings Ridge 3684 EVERSHOLT ST, CLERMONT, FL, 34711, Clermont, FL 34711
$309,900

3 beds

|

2 baths

|

1,552 sq ft

|

House

3684 EVERSHOLT ST, CLERMONT, FL, 34711
Community: Kings Ridge
Royal Highlands 20751 QUEEN ALEXANDRA DR, LEESBURG, FL, ..., Leesburg, FL 34748
$364,900

3 beds

|

3 baths

|

2,224 sq ft

|

House

20751 QUEEN ALEXANDRA DR, LEESBURG, FL, ...
Community: Royal Highlands
Kings Ridge 3667 KINGSWOOD CT, CLERMONT, FL, 34711, Clermont, FL 34711
$339,900

2 beds

|

2 baths

|

1,552 sq ft

|

House

3667 KINGSWOOD CT, CLERMONT, FL, 34711
Community: Kings Ridge
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® 9199 SE 171ST COOPER LOOP, THE VILLAGES,..., The Villages, FL 32162
$399,000

3 beds

|

2 baths

|

1,850 sq ft

|

House

9199 SE 171ST COOPER LOOP, THE VILLAGES,...
Community: The Villages®
Trilogy® Orlando 119 CRESCENT MOON DR, GROVELAND, FL, 347..., Groveland, FL 34736
$315,000

2 beds

|

2 baths

|

1,556 sq ft

|

House

119 CRESCENT MOON DR, GROVELAND, FL, 347...
Community: Trilogy® Orlando
Cindy Certified
10611 GRAND OAKS BLVD, OXFORD, FL, 34484, Oxford, FL 34484
$409,000

4 beds

|

2 baths

|

1,754 sq ft

|

House

10611 GRAND OAKS BLVD, OXFORD, FL, 34484
Cindy Certified
10619 GRAND OAKS BLVD, OXFORD, FL, 34484, Oxford, FL 34484
$399,999

3 beds

|

2 baths

|

1,806 sq ft

|

House

10619 GRAND OAKS BLVD, OXFORD, FL, 34484
Cindy Certified
10547 BURLWOOD DR, LEESBURG, FL, 34788, Leesburg, FL 34788
$330,000

3 beds

|

2 baths

|

1,697 sq ft

|

House

10547 BURLWOOD DR, LEESBURG, FL, 34788

Frequently Asked Questions


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