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Leesburg, FL 55+ active adult communities & homes for sale - Page 17

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
Del Webb Minneola 2546 DEL WEBB DR, MINNEOLA, FL, 34715, Minneola, FL 34715
$589,000

3 beds

|

2 baths

|

1,905 sq ft

|

House

2546 DEL WEBB DR, MINNEOLA, FL, 34715
Community: Del Webb Minneola
The Villages® 631 ENCONTO ST, THE VILLAGES, FL, 32159, The Villages, FL 32159
$299,900

2 beds

|

2 baths

|

1,128 sq ft

|

Villa

631 ENCONTO ST, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 413 S TIMBER TRL, WILDWOOD, FL, 34785, Wildwood, FL 34785
$124,900

2 beds

|

2 baths

|

1,092 sq ft

|

Manufactured Home

413 S TIMBER TRL, WILDWOOD, FL, 34785
Community: The Villages®
Cindy Certified
4566 LIVE OAK LN, OXFORD, FL, 34484, Oxford, FL 34484
$398,990

4 beds

|

3 baths

|

2,165 sq ft

|

House

4566 LIVE OAK LN, OXFORD, FL, 34484
Royal Highlands 20554 QUEEN ALEXANDRA DR, LEESBURG, FL, ..., Leesburg, FL 34748
$459,900

3 beds

|

2 baths

|

2,583 sq ft

|

House

20554 QUEEN ALEXANDRA DR, LEESBURG, FL, ...
Community: Royal Highlands
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
Plantation at Leesburg 4755 TARA VIEW RD, LEESBURG, FL, 34748, Leesburg, FL 34748
$295,000

2 beds

|

2 baths

|

2,035 sq ft

|

House

4755 TARA VIEW RD, LEESBURG, FL, 34748
Scottish Highlands 70 STONE HAVEN CT, LEESBURG, FL, 34788, Leesburg, FL 34788
$255,000

3 beds

|

3 baths

|

2,146 sq ft

|

House

70 STONE HAVEN CT, LEESBURG, FL, 34788
Community: Scottish Highlands
The Villages® 710 CORTEZ AVE, THE VILLAGES, FL, 32159, The Villages, FL 32159
$283,000

2 beds

|

2 baths

|

1,564 sq ft

|

House

710 CORTEZ AVE, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 3501 CONNOR WAY, THE VILLAGES, FL, 32163, The Villages, FL 32163
$435,000

3 beds

|

2 baths

|

1,492 sq ft

|

Villa

3501 CONNOR WAY, THE VILLAGES, FL, 32163
Community: The Villages®
Stonecrest 11932 SE 179TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$305,000

3 beds

|

3 baths

|

2,118 sq ft

|

House

11932 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.
Arlington Ridge 3601 ARLINGTON RIDGE BLVD, LEESBURG, FL,..., Leesburg, FL 34748
$300,000

2 beds

|

2 baths

|

1,649 sq ft

|

House

3601 ARLINGTON RIDGE BLVD, LEESBURG, FL,...
Community: Arlington Ridge
Cindy Certified
1258 TURTLE ISLAND RD, LADY LAKE, FL, 32..., Lady Lake, FL 32159
$249,990

3 beds

|

2 baths

|

1,509 sq ft

|

Villa

1258 TURTLE ISLAND RD, LADY LAKE, FL, 32...
Cindy Certified
1079 OCEAN LODGE RD, LADY LAKE, FL, 3215..., Lady Lake, FL 32159
$324,990

3 beds

|

2 baths

|

2,021 sq ft

|

House

1079 OCEAN LODGE RD, LADY LAKE, FL, 3215...
Royal Highlands 5619 PRINCE ANDREW CT, LEESBURG, FL, 347..., Leesburg, FL 34748
$337,262

3 beds

|

2 baths

|

1,776 sq ft

|

House

5619 PRINCE ANDREW CT, LEESBURG, FL, 347...
Community: Royal Highlands
The Villages® 313 GONZALES PL, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$349,900

2 beds

|

2 baths

|

1,240 sq ft

|

House

313 GONZALES PL, LADY LAKE, FL, 32159
Community: The Villages®
Cindy Certified
11426 LAKEVIEW DR, LEESBURG, FL, 34788, Leesburg, FL 34788
$315,000

3 beds

|

2 baths

|

1,457 sq ft

|

House

11426 LAKEVIEW DR, LEESBURG, FL, 34788
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
The Villages® 970 KENOVA AVE, THE VILLAGES, FL, 32162, The Villages, FL 32162
$325,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

970 KENOVA AVE, THE VILLAGES, FL, 32162
Community: The Villages®
Harbor Hills Country Club 5141 GREENS DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$669,500

4 beds

|

3 baths

|

2,500 sq ft

|

House

5141 GREENS DR, LADY LAKE, FL, 32159
The Villages® 2850 CHARLEVOIX ST, THE VILLAGES, FL, 32..., The Villages, FL 32163
$469,900

3 beds

|

2 baths

|

1,461 sq ft

|

Villa

2850 CHARLEVOIX ST, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 764 BAISLEY TRL, THE VILLAGES, FL, 32162, The Villages, FL 32162
$439,900

3 beds

|

2 baths

|

1,861 sq ft

|

House

764 BAISLEY TRL, 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.
The Villages® 2844 PLAINRIDGE LOOP, THE VILLAGES, FL, ..., The Villages, FL 32162
$365,000

2 beds

|

2 baths

|

1,142 sq ft

|

House

2844 PLAINRIDGE LOOP, THE VILLAGES, FL, ...
Community: The Villages®
Royal Harbor 3393 BALTIC SEA BLVD, TAVARES, FL, 32778, Tavares, FL 32778
$330,000

3 beds

|

2 baths

|

1,902 sq ft

|

House

3393 BALTIC SEA BLVD, TAVARES, FL, 32778
Community: Royal Harbor
Stonecrest 17832 SE 115TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$310,000

3 beds

|

3 baths

|

1,749 sq ft

|

House

17832 SE 115TH CT, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Kings Ridge 4334 HAMMERSMITH DR, CLERMONT, FL, 34711, Clermont, FL 34711
$379,000

2 beds

|

2 baths

|

1,989 sq ft

|

House

4334 HAMMERSMITH DR, CLERMONT, FL, 34711
Community: Kings Ridge
Kings Ridge 1940 FARMINGTON CT, CLERMONT, FL, 34711, Clermont, FL 34711
$397,000

2 beds

|

3 baths

|

1,722 sq ft

|

House

1940 FARMINGTON CT, CLERMONT, FL, 34711
Community: Kings Ridge
Harbor Hills Country Club 5331 GROVE MNR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$539,000

4 beds

|

3 baths

|

2,332 sq ft

|

House

5331 GROVE MNR, LADY LAKE, FL, 32159
The Villages® 17116 SE 79TH MCLAWREN TER, THE VILLAGES..., The Villages, FL 32162
$650,000

3 beds

|

2 baths

|

2,097 sq ft

|

House

17116 SE 79TH MCLAWREN TER, THE VILLAGES...
Community: The Villages®
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
Harbor Hills Country Club 38700 LAKEVIEW WALK, LADY LAKE, FL, 3215..., Lady Lake, FL 32159
$645,000

3 beds

|

3 baths

|

2,354 sq ft

|

House

38700 LAKEVIEW WALK, LADY LAKE, FL, 3215...
The Villages® 5 HICKORY HEAD HAMMOCK, THE VILLAGES, FL..., The Villages, FL 32159
$499,850

2 beds

|

2 baths

|

1,898 sq ft

|

House

5 HICKORY HEAD HAMMOCK, THE VILLAGES, FL...
Community: The Villages®
The Villages® 1115 SALDIVAR RD, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$434,000

3 beds

|

2 baths

|

1,628 sq ft

|

House

1115 SALDIVAR RD, THE VILLAGES, FL, 3215...
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 3604 KINGSWOOD CT, CLERMONT, FL, 34711, Clermont, FL 34711
$320,000

2 beds

|

2 baths

|

1,377 sq ft

|

House

3604 KINGSWOOD CT, CLERMONT, FL, 34711
Community: Kings Ridge
The Villages® 1304 BRUNELL ST, THE VILLAGES, FL, 32163, The Villages, FL 32163
$490,000

3 beds

|

3 baths

|

2,084 sq ft

|

House

1304 BRUNELL ST, THE VILLAGES, FL, 32163
Community: The Villages®
Royal Harbor 5809 BOUNTY CIR, TAVARES, FL, 32778, Tavares, FL 32778
$325,000

3 beds

|

2 baths

|

1,949 sq ft

|

House

5809 BOUNTY CIR, TAVARES, FL, 32778
Community: Royal Harbor
Harbor Hills Country Club 6042 LANDINGS BLVD, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$619,900

3 beds

|

2 baths

|

1,850 sq ft

|

House

6042 LANDINGS BLVD, LADY LAKE, FL, 32159
The Villages® 7851 SE 173RD PANORAMA PL, THE VILLAGES,..., The Villages, FL 32162
$214,000

1 beds

|

1 baths

|

955 sq ft

|

Villa

7851 SE 173RD PANORAMA PL, THE VILLAGES,...
Community: The Villages®
Stonecrest 12220 SE 172ND LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$269,999

3 beds

|

2 baths

|

1,330 sq ft

|

House

12220 SE 172ND LN, SUMMERFIELD, FL, 3449...
Community: Stonecrest
The Villages® 9188 SE 166TH SPRUNG LN, THE VILLAGES, F..., The Villages, FL 32162
$335,000

3 beds

|

2 baths

|

1,437 sq ft

|

Villa

9188 SE 166TH SPRUNG LN, THE VILLAGES, F...
Community: The Villages®
Esplanade at McKinnon Groves 17742 SEDONA ST, WINTER GARDEN, FL, 3478..., Winter Garden, FL 34787
$900,000

3 beds

|

3 baths

|

2,475 sq ft

|

House

17742 SEDONA ST, WINTER GARDEN, FL, 3478...
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
The Villages® 7618 SE 171ST SUN VALLEY PL, THE VILLAGE..., The Villages, FL 32162
$325,000

2 beds

|

2 baths

|

1,332 sq ft

|

Villa

7618 SE 171ST SUN VALLEY PL, THE VILLAGE...
Community: The Villages®
Pennbrooke Fairways 228 GRAND VISTA TRL, LEESBURG, FL, 34748, Leesburg, FL 34748
$270,000

2 beds

|

2 baths

|

1,568 sq ft

|

House

228 GRAND VISTA TRL, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
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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