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Leesburg, FL 55+ active adult communities & homes for sale - Page 18

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® 8420 COUNTY RD A1, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$299,900

3 beds

|

2 baths

|

2,176 sq ft

|

Manufactured Home

8420 COUNTY RD A1, LADY LAKE, FL, 32159
Community: The Villages®
The Villages® 3452 BOSIE RUN, THE VILLAGES, FL, 32163, The Villages, FL 32163
$950,000

3 beds

|

3 baths

|

2,192 sq ft

|

House

3452 BOSIE RUN, THE VILLAGES, FL, 32163
Community: The Villages®
Stonecrest 17879 SE 125TH CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$415,000

3 beds

|

3 baths

|

2,071 sq ft

|

House

17879 SE 125TH CIR, SUMMERFIELD, FL, 344...
Community: Stonecrest
The Villages® 3602 PEPPERIDGE CIR, THE VILLAGES, FL, 3..., The Villages, FL 32163
$440,000

3 beds

|

2 baths

|

1,731 sq ft

|

House

3602 PEPPERIDGE CIR, THE VILLAGES, FL, 3...
Community: The Villages®
Esplanade at McKinnon Groves 11341 BOURBON ROSE CIR, WINTER GARDEN, F..., Winter Garden, FL 34787
$925,000

4 beds

|

5 baths

|

2,974 sq ft

|

House

11341 BOURBON ROSE CIR, WINTER GARDEN, F...
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
The Villages® 2129 MARGARITA DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$372,000

3 beds

|

2 baths

|

1,694 sq ft

|

House

2129 MARGARITA DR, THE VILLAGES, FL, 321...
Community: The Villages®
The Villages® 2716 LYALL LOOP, THE VILLAGES, FL, 32163, The Villages, FL 32163
$589,000

3 beds

|

2 baths

|

1,920 sq ft

|

House

2716 LYALL LOOP, THE VILLAGES, FL, 32163
Community: The Villages®
Esplanade at McKinnon Groves 11275 SILVER TRUMPET LOOP, WINTER GARDEN..., Winter Garden, FL 34787
$400,000

2 beds

|

2 baths

|

1,515 sq ft

|

Villa

11275 SILVER TRUMPET LOOP, WINTER GARDEN...
Esplanade at McKinnon Groves 11279 SILVER TRUMPET LOOP, WINTER GARDEN..., Winter Garden, FL 34787
$432,318

2 beds

|

2 baths

|

1,515 sq ft

|

Villa

11279 SILVER TRUMPET LOOP, WINTER GARDEN...
Stonecrest 11972 SE 176TH PLACE RD, SUMMERFIELD, FL..., Summerfield, FL 34491
$315,000

3 beds

|

2 baths

|

1,738 sq ft

|

House

11972 SE 176TH PLACE 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.
Cindy Certified
3625 SUBLETT LOOP, TAVARES, FL, 32778, Tavares, FL 32778
$457,000

4 beds

|

3 baths

|

2,053 sq ft

|

House

3625 SUBLETT LOOP, TAVARES, FL, 32778
Summit Greens 794 WOLF CREEK ST, CLERMONT, FL, 34711, Clermont, FL 34711
$350,000

3 beds

|

2 baths

|

1,747 sq ft

|

House

794 WOLF CREEK ST, CLERMONT, FL, 34711
Community: Summit Greens
Trilogy® Orlando 273 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736
$479,888

2 beds

|

3 baths

|

2,140 sq ft

|

House

273 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
The Villages® 17481 SE 76TH FLINTLOCK TER, THE VILLAGE..., The Villages, FL 32162
$285,000

2 beds

|

2 baths

|

1,148 sq ft

|

House

17481 SE 76TH FLINTLOCK TER, THE VILLAGE...
Community: The Villages®
The Villages® 2673 SUFFOLK ST, THE VILLAGES, FL, 32162, The Villages, FL 32162
$297,000

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

2673 SUFFOLK ST, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 5230 LEXINGTON CIR, WILDWOOD, FL, 34785, Wildwood, FL 34785
$219,900

2 beds

|

2 baths

|

1,367 sq ft

|

Manufactured Home

5230 LEXINGTON CIR, WILDWOOD, FL, 34785
Community: The Villages®
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
The Villages® 726 BRADFORD LOOP, THE VILLAGES, FL, 321..., The Villages, FL 32163
$415,000

3 beds

|

2 baths

|

1,561 sq ft

|

House

726 BRADFORD LOOP, THE VILLAGES, FL, 321...
Community: The Villages®
The Villages® 1106 RICARDO AVE, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$318,000

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

1106 RICARDO AVE, THE VILLAGES, FL, 3215...
Community: The Villages®
The Villages® 17770 SE 85TH ELLERBE AVE, THE VILLAGES,..., The Villages, FL 32162
$420,000

3 beds

|

2 baths

|

1,749 sq ft

|

House

17770 SE 85TH ELLERBE AVE, THE VILLAGES,...
Community: The Villages®
The Villages® 108 CHERRY BLOSSOM LN, LADY LAKE, FL, 32..., Lady Lake, FL 32159
$335,900

4 beds

|

2 baths

|

1,754 sq ft

|

House

108 CHERRY BLOSSOM LN, LADY LAKE, FL, 32...
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.
Legacy of Leesburg 5530 CELEBRATION WAY, LEESBURG, FL, 3474..., Leesburg, FL 34748
$399,999

3 beds

|

2 baths

|

2,593 sq ft

|

House

5530 CELEBRATION WAY, LEESBURG, FL, 3474...
Community: Legacy of Leesburg
Stonecrest 11193 SE 173RD PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$332,750

3 beds

|

2 baths

|

1,974 sq ft

|

House

11193 SE 173RD PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Arlington Ridge 4348 ANTIETAM CREEK TRL, LEESBURG, FL, 3..., Leesburg, FL 34748
$436,415

3 beds

|

3 baths

|

2,359 sq ft

|

House

4348 ANTIETAM CREEK TRL, LEESBURG, FL, 3...
Community: Arlington Ridge
Spruce Creek South 17832 SE 96TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$239,900

2 beds

|

2 baths

|

1,248 sq ft

|

House

17832 SE 96TH AVE, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
The Villages® 3101 ARCHER AVE, THE VILLAGES, FL, 32162, The Villages, FL 32162
$539,500

3 beds

|

2 baths

|

2,058 sq ft

|

Villa

3101 ARCHER AVE, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 867 CORTEZ AVE, THE VILLAGES, FL, 32159, The Villages, FL 32159
$350,000

2 beds

|

2 baths

|

1,770 sq ft

|

House

867 CORTEZ AVE, THE VILLAGES, FL, 32159
Community: The Villages®
Pennbrooke Fairways 33236 GRAND CYPRESS WAY, LEESBURG, FL, 3..., Leesburg, FL 34748
$279,247

3 beds

|

2 baths

|

1,598 sq ft

|

House

33236 GRAND CYPRESS WAY, LEESBURG, FL, 3...
Community: Pennbrooke Fairways
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
The Villages® 12439 NE 48TH CIR, OXFORD, FL, 34484, Oxford, FL 34484
$355,000

4 beds

|

3 baths

|

2,224 sq ft

|

House

12439 NE 48TH CIR, OXFORD, FL, 34484
Community: The Villages®
Summit Greens 1028 EVEREST ST, CLERMONT, FL, 34711, Clermont, FL 34711
$379,000

3 beds

|

2 baths

|

2,084 sq ft

|

House

1028 EVEREST ST, CLERMONT, FL, 34711
Community: Summit Greens
Stonecrest 11860 SE 179TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$519,000

3 beds

|

3 baths

|

2,222 sq ft

|

House

11860 SE 179TH ST, SUMMERFIELD, FL, 3449...
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.
The Villages® 308 ALMERIA ST, THE VILLAGES, FL, 32162, The Villages, FL 32162
$335,000

2 beds

|

2 baths

|

1,132 sq ft

|

Villa

308 ALMERIA ST, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 2877 FEUSTEL AVE, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$390,000

3 beds

|

2 baths

|

1,384 sq ft

|

Villa

2877 FEUSTEL AVE, THE VILLAGES, FL, 3216...
Community: The Villages®
Cindy Certified
436 LEMONGRASS RD, MINNEOLA, FL, 34715, Minneola, FL 34715
$579,990

4 beds

|

3 baths

|

2,105 sq ft

|

House

436 LEMONGRASS RD, MINNEOLA, FL, 34715
The Villages® 1967 FLOWERSVILLE PL, THE VILLAGES, FL, ..., The Villages, FL 32163
$530,000

3 beds

|

3 baths

|

2,016 sq ft

|

House

1967 FLOWERSVILLE PL, THE VILLAGES, FL, ...
Community: The Villages®
Royal Harbor 6170 SAILBOAT AVE, TAVARES, FL, 32778, Tavares, FL 32778
$346,000

3 beds

|

2 baths

|

1,535 sq ft

|

House

6170 SAILBOAT AVE, TAVARES, FL, 32778
Community: Royal Harbor
Trilogy® Orlando 290 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736
$589,900

2 beds

|

3 baths

|

2,315 sq ft

|

House

290 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
Harbor Hills Country Club 5701 CRESTVIEW DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$529,500

5 beds

|

3 baths

|

2,448 sq ft

|

House

5701 CRESTVIEW DR, LADY LAKE, FL, 32159
Heritage - The Cottages of Sanders Grove 6217 SANDERS GROVE CIR 1, OKAHUMKA, FL, ..., Okahumka, FL 34762
$363,389

4 beds

|

3 baths

|

1,938 sq ft

|

House

6217 SANDERS GROVE CIR 1, OKAHUMKA, FL, ...
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
Heritage - The Cottages of Sanders Grove 5715 5715 HIAWASSEE RD, OKAHUMKA, FL, 34..., Okahumka, FL 34762
$349,250

4 beds

|

3 baths

|

1,938 sq ft

|

House

5715 5715 HIAWASSEE RD, OKAHUMKA, FL, 34...
Heritage - The Cottages of Sanders Grove 6209 SANDERS GROVE CIR 1, OKAHUMKA, FL, ..., Okahumka, FL 34762
$343,445

4 beds

|

2 baths

|

1,758 sq ft

|

House

6209 SANDERS GROVE CIR 1, OKAHUMKA, FL, ...
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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