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Leesburg, FL 55+ active adult communities & homes for sale - Page 2

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
Plantation at Leesburg 24809 RIVERBOAT BND, LEESBURG, FL, 34748, Leesburg, FL 34748
$300,000

2 beds

|

2 baths

|

1,829 sq ft

|

House

24809 RIVERBOAT BND, LEESBURG, FL, 34748
Spruce Creek South 10434 SE 178TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$224,900

2 beds

|

2 baths

|

1,008 sq ft

|

House

10434 SE 178TH PL, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
Spruce Creek South 17565 SE 102ND AVE, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$249,000

2 beds

|

2 baths

|

1,144 sq ft

|

House

17565 SE 102ND AVE, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
The Villages® 438 TARRSON BLVD, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$169,900

2 beds

|

2 baths

|

960 sq ft

|

Manufactured Home

438 TARRSON BLVD, LADY LAKE, FL, 32159
Community: The Villages®
The Villages® 1926 ELDRIDGE LOOP, THE VILLAGES, FL, 32..., The Villages, FL 32162
$440,000

3 beds

|

2 baths

|

1,751 sq ft

|

House

1926 ELDRIDGE LOOP, 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
Stonecrest 17432 SE 112TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$329,000

2 beds

|

2 baths

|

1,706 sq ft

|

House

17432 SE 112TH CT, SUMMERFIELD, FL, 3449...
Community: Stonecrest
The Villages® 1230 CARVELLO DR, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$435,000

4 beds

|

3 baths

|

1,661 sq ft

|

House

1230 CARVELLO DR, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 954 BARRYMOORE LOOP, THE VILLAGES, FL, 3..., The Villages, FL 32162
$345,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

954 BARRYMOORE LOOP, THE VILLAGES, FL, 3...
Community: The Villages®
Stonecrest 17187 SE 116TH COURT RD, SUMMERFIELD, FL..., Summerfield, FL 34491
$474,900

3 beds

|

3 baths

|

2,026 sq ft

|

House

17187 SE 116TH COURT RD, SUMMERFIELD, FL...
Community: Stonecrest
The Villages® 3161 DRESSENDORFER DR, THE VILLAGES, FL,..., The Villages, FL 32163
$385,000

3 beds

|

2 baths

|

1,907 sq ft

|

House

3161 DRESSENDORFER DR, 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.
The Villages® 2835 CEDAR GROVE LOOP, THE VILLAGES, FL,..., The Villages, FL 32163
$849,000

4 beds

|

3 baths

|

2,759 sq ft

|

House

2835 CEDAR GROVE LOOP, THE VILLAGES, FL,...
Community: The Villages®
Harbor Hills Country Club 39914 SUNBEAM WAY, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$319,999

3 beds

|

2 baths

|

2,034 sq ft

|

House

39914 SUNBEAM WAY, LADY LAKE, FL, 32159
The Villages® 3342 VELTRE WAY, THE VILLAGES, FL, 32163, The Villages, FL 32163
$499,900

4 beds

|

2 baths

|

2,013 sq ft

|

House

3342 VELTRE WAY, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 2917 LARRANAGA DR, THE VILLAGES, FL, 321..., The Villages, FL 32162
$3,100,000

5 beds

|

4 baths

|

6,070 sq ft

|

House

2917 LARRANAGA DR, THE VILLAGES, FL, 321...
Community: The Villages®
The Villages® 1436 W SCHWARTZ BLVD, LADY LAKE, FL, 321..., Lady Lake, FL 32159
$300,000

2 beds

|

2 baths

|

1,144 sq ft

|

House

1436 W SCHWARTZ BLVD, LADY LAKE, FL, 321...
Community: The Villages®
Pennbrooke Fairways 341 RANCHWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$319,000

3 beds

|

2 baths

|

2,014 sq ft

|

House

341 RANCHWOOD DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
Trilogy® Orlando 394 ALCOVE DR, GROVELAND, FL, 34736, Groveland, FL 34736
$325,000

2 beds

|

2 baths

|

1,568 sq ft

|

House

394 ALCOVE DR, GROVELAND, FL, 34736
Community: Trilogy® Orlando
The Villages® 1115 SAN BERNARDO RD, THE VILLAGES, FL, ..., The Villages, FL 32162
$319,900

2 beds

|

2 baths

|

1,146 sq ft

|

Villa

1115 SAN BERNARDO RD, THE VILLAGES, FL, ...
Community: The Villages®
The Villages® 2300 RILEY RD, THE VILLAGES, FL, 32162, The Villages, FL 32162
$269,000

2 beds

|

2 baths

|

1,156 sq ft

|

House

2300 RILEY RD, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 388 BRADLEY TER, THE VILLAGES, FL, 32162, The Villages, FL 32162
$374,900

2 beds

|

2 baths

|

1,196 sq ft

|

Villa

388 BRADLEY TER, THE VILLAGES, FL, 32162
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.
Arlington Ridge 4719 HERITAGE TRL, LEESBURG, FL, 34748, Leesburg, FL 34748
$519,900

2 beds

|

2 baths

|

1,761 sq ft

|

House

4719 HERITAGE TRL, LEESBURG, FL, 34748
Community: Arlington Ridge
Kings Ridge 4122 KINGSLEY ST, CLERMONT, FL, 34711, Clermont, FL 34711
$350,000

2 beds

|

2 baths

|

2,031 sq ft

|

House

4122 KINGSLEY ST, CLERMONT, FL, 34711
Community: Kings Ridge
Legacy of Leesburg 26717 WETLANDS WAY, LEESBURG, FL, 34748, Leesburg, FL 34748
$365,000

3 beds

|

3 baths

|

2,620 sq ft

|

House

26717 WETLANDS WAY, LEESBURG, FL, 34748
Community: Legacy of Leesburg
The Villages® 1863 DALTON DR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$300,000

2 beds

|

2 baths

|

1,152 sq ft

|

Villa

1863 DALTON DR, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 1700 JADESTONE TER, THE VILLAGES, FL, 32..., The Villages, FL 32162
$359,000

2 beds

|

2 baths

|

1,138 sq ft

|

Villa

1700 JADESTONE TER, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 798 MILLHORN LOOP, THE VILLAGES, FL, 321..., The Villages, FL 32163
$359,000

3 beds

|

2 baths

|

1,500 sq ft

|

House

798 MILLHORN LOOP, THE VILLAGES, FL, 321...
Community: The Villages®
Cindy Certified
9760 BLACK WALNUT DR, CLERMONT, FL, 3471..., Clermont, FL 34715
$370,000

3 beds

|

2 baths

|

1,516 sq ft

|

House

9760 BLACK WALNUT DR, CLERMONT, FL, 3471...
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
The Villages® 497 LITTLE RIVER PATH, THE VILLAGES, FL,..., The Villages, FL 32162
$400,000

3 beds

|

2 baths

|

1,568 sq ft

|

House

497 LITTLE RIVER PATH, THE VILLAGES, FL,...
Community: The Villages®
The Villages® 1034 VENTURA DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$270,000

2 beds

|

2 baths

|

1,338 sq ft

|

House

1034 VENTURA DR, LADY LAKE, FL, 32159
Community: The Villages®
The Villages® 2800 PLAINRIDGE LOOP, THE VILLAGES, FL, ..., The Villages, FL 32162
$349,900

3 beds

|

2 baths

|

1,240 sq ft

|

House

2800 PLAINRIDGE LOOP, 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.
The Villages® 1836 CAPTIVA CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$324,900

3 beds

|

2 baths

|

1,392 sq ft

|

House

1836 CAPTIVA CT, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 3277 KRANZ AVE, THE VILLAGES, FL, 32163, The Villages, FL 32163
$465,000

3 beds

|

3 baths

|

1,854 sq ft

|

House

3277 KRANZ AVE, THE VILLAGES, FL, 32163
Community: The Villages®
Baytree 136 JUNIPER WAY, TAVARES, FL, 32778, Tavares, FL 32778
$267,990

2 beds

|

2 baths

|

1,179 sq ft

|

Villa

136 JUNIPER WAY, TAVARES, FL, 32778
Community: Baytree
Cindy Certified
10381 CHURCH HAMMOCK RD, LEESBURG, FL, 3..., Leesburg, FL 34788
$375,000

4 beds

|

3 baths

|

2,077 sq ft

|

House

10381 CHURCH HAMMOCK RD, LEESBURG, FL, 3...
The Villages® 4157 COLLERETTE CT, THE VILLAGES, FL, 32..., The Villages, FL 32163
$484,900

3 beds

|

2 baths

|

1,949 sq ft

|

House

4157 COLLERETTE CT, THE VILLAGES, FL, 32...
Community: The Villages®
Esplanade at Highland Ranch 959 BRAEWOOD DR, CLERMONT, FL, 34715, Clermont, FL 34715
$400,000

2 beds

|

2 baths

|

1,788 sq ft

|

House

959 BRAEWOOD DR, CLERMONT, FL, 34715
The Villages® 1241 TARFLOWER TER, THE VILLAGES, FL, 32..., The Villages, FL 32163
$497,000

3 beds

|

2 baths

|

1,956 sq ft

|

House

1241 TARFLOWER TER, THE VILLAGES, FL, 32...
Community: The Villages®
Pennbrooke Fairways 1145 EAGLES LNDG, LEESBURG, FL, 34748, Leesburg, FL 34748
$249,900

3 beds

|

2 baths

|

1,639 sq ft

|

House

1145 EAGLES LNDG, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
Lakeside Landings 10371 ADDISON SHORE WAY, OXFORD, FL, 344..., Oxford, FL 34484
$425,000

4 beds

|

3 baths

|

2,016 sq ft

|

House

10371 ADDISON SHORE WAY, OXFORD, FL, 344...
Community: Lakeside Landings
Legacy of Leesburg 5127 AURORA DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$349,900

3 beds

|

2 baths

|

2,386 sq ft

|

House

5127 AURORA DR, 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.

Frequently Asked Questions


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1,145 homes
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