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Leesburg, FL 55+ active adult communities & homes for sale - Page 23

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® 3087 BLACKSTOCK WAY, THE VILLAGES, FL, 3..., The Villages, FL 32163
$489,000

3 beds

|

2 baths

|

2,046 sq ft

|

House

3087 BLACKSTOCK WAY, THE VILLAGES, FL, 3...
Community: The Villages®
Heritage Hills 4056 SERENA LN, CLERMONT, FL, 34711, Clermont, FL 34711
$367,900

3 beds

|

2 baths

|

1,857 sq ft

|

House

4056 SERENA LN, CLERMONT, FL, 34711
Community: Heritage Hills
Cindy Certified
823 SUNSHOWER DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$294,000

4 beds

|

2 baths

|

1,840 sq ft

|

House

823 SUNSHOWER DR, LADY LAKE, FL, 32159
Harbor Hills Country Club 6115 LANDINGS BLVD, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$349,900

3 beds

|

2 baths

|

1,640 sq ft

|

House

6115 LANDINGS BLVD, LADY LAKE, FL, 32159
Del Webb Minneola 1384 ZESTY CITRUS LN, MINNEOLA, FL, 3471..., Minneola, FL 34715
$569,000

3 beds

|

2 baths

|

1,737 sq ft

|

House

1384 ZESTY CITRUS LN, MINNEOLA, FL, 3471...
Community: Del Webb Minneola
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
Arlington Ridge 26617 OTTER CREEK LN, LEESBURG, FL, 3474..., Leesburg, FL 34748
$492,500

4 beds

|

3 baths

|

2,580 sq ft

|

House

26617 OTTER CREEK LN, LEESBURG, FL, 3474...
Community: Arlington Ridge
Plantation at Leesburg 3538 MULBERRY GROVE LOOP, LEESBURG, FL, ..., Leesburg, FL 34748
$403,000

3 beds

|

2 baths

|

2,407 sq ft

|

House

3538 MULBERRY GROVE LOOP, LEESBURG, FL, ...
The Villages® 2047 DUNSTER CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$424,999

3 beds

|

2 baths

|

1,851 sq ft

|

House

2047 DUNSTER CT, THE VILLAGES, FL, 32162
Community: The Villages®
Royal Harbor 3257 BALTIC SEA BLVD, TAVARES, FL, 32778, Tavares, FL 32778
$374,900

3 beds

|

3 baths

|

2,012 sq ft

|

House

3257 BALTIC SEA BLVD, TAVARES, FL, 32778
Community: Royal Harbor
The Villages® 418 FLOSSMOOR CT, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$405,000

3 beds

|

2 baths

|

1,685 sq ft

|

Villa

418 FLOSSMOOR CT, 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.
Plantation at Leesburg 5030 EL DESTINO DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$223,000

2 beds

|

2 baths

|

1,308 sq ft

|

House

5030 EL DESTINO DR, LEESBURG, FL, 34748
Highland Lakes 26912 BECKER CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$360,000

3 beds

|

2 baths

|

2,498 sq ft

|

House

26912 BECKER CT, LEESBURG, FL, 34748
Community: Highland Lakes
Spruce Creek South 9532 SE 173RD LN, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$240,000

2 beds

|

2 baths

|

1,678 sq ft

|

House

9532 SE 173RD LN, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
Pennbrooke Fairways 412 WESTWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$170,000

2 beds

|

2 baths

|

1,140 sq ft

|

House

412 WESTWOOD DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Harbor Hills Country Club 5066 GREENS DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$599,999

4 beds

|

3 baths

|

2,544 sq ft

|

House

5066 GREENS DR, LADY LAKE, FL, 32159
Highland Lakes 5503 LAVER ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$219,900

2 beds

|

2 baths

|

1,332 sq ft

|

House

5503 LAVER ST, LEESBURG, FL, 34748
Community: Highland Lakes
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
The Villages® 23202 SANDALWOOD DR 202, WILDWOOD, FL, 3..., Wildwood, FL 34785
$129,900

3 beds

|

3 baths

|

1,474 sq ft

|

Condo

23202 SANDALWOOD DR 202, WILDWOOD, FL, 3...
Community: The Villages®
Highland Lakes 6419 BORG ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$279,900

3 beds

|

2 baths

|

1,964 sq ft

|

House

6419 BORG ST, LEESBURG, FL, 34748
Community: Highland Lakes
Royal Highlands 21101 BRAVEHEART DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$349,900

3 beds

|

3 baths

|

2,221 sq ft

|

House

21101 BRAVEHEART DR, LEESBURG, FL, 34748
Community: Royal Highlands
The Villages® 2382 OTHELLO CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$339,900

2 beds

|

2 baths

|

1,196 sq ft

|

Villa

2382 OTHELLO CT, 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® 170 PALERMO PL, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$412,500

3 beds

|

2 baths

|

1,979 sq ft

|

House

170 PALERMO PL, LADY LAKE, FL, 32159
Community: The Villages®
The Villages® 3746 NEW MOON AVE, THE VILLAGES, FL, 321..., The Villages, FL 32163
$478,788

3 beds

|

2 baths

|

1,905 sq ft

|

House

3746 NEW MOON AVE, THE VILLAGES, FL, 321...
Community: The Villages®
Kings Ridge 4215 GREENWICH CT, CLERMONT, FL, 34711, Clermont, FL 34711
$348,000

2 beds

|

2 baths

|

2,000 sq ft

|

House

4215 GREENWICH CT, CLERMONT, FL, 34711
Community: Kings Ridge
Royal Harbor 4962 RAINBOW TROUT RD, TAVARES, FL, 3277..., Tavares, FL 32778
$269,900

3 beds

|

2 baths

|

1,489 sq ft

|

House

4962 RAINBOW TROUT RD, TAVARES, FL, 3277...
Community: Royal Harbor
Cindy Certified
291 PRICKLY PEAR CT, LADY LAKE, FL, 3215..., Lady Lake, FL 32159
$279,990

3 beds

|

2 baths

|

1,549 sq ft

|

House

291 PRICKLY PEAR CT, LADY LAKE, FL, 3215...
The Villages® 1678 GOVAN PL, THE VILLAGES, FL, 32162, The Villages, FL 32162
$549,900

3 beds

|

2 baths

|

1,978 sq ft

|

Villa

1678 GOVAN PL, THE VILLAGES, FL, 32162
Community: The Villages®
Cindy Certified
15351 WILLOW RIDGE DR, MONTVERDE, FL, 34..., Montverde, FL 34756
$650,000

3 beds

|

4 baths

|

2,976 sq ft

|

House

15351 WILLOW RIDGE DR, MONTVERDE, FL, 34...
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
The Villages® 17350 SE 77TH SYCAMORE AVE, THE VILLAGES..., The Villages, FL 32162
$240,000

2 beds

|

1 baths

|

1,071 sq ft

|

Villa

17350 SE 77TH SYCAMORE AVE, THE VILLAGES...
Community: The Villages®
Kings Ridge 3811 WESTERHAM DR, CLERMONT, FL, 34711, Clermont, FL 34711
$310,500

2 beds

|

2 baths

|

1,679 sq ft

|

House

3811 WESTERHAM DR, CLERMONT, FL, 34711
Community: Kings Ridge
The Villages® 1616 BAYHILL DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$249,000

2 beds

|

2 baths

|

1,300 sq ft

|

Manufactured Home

1616 BAYHILL DR, LADY LAKE, 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.
The Villages® 1606 SNELLING AVE, THE VILLAGES, FL, 321..., The Villages, FL 32162
$579,000

3 beds

|

2 baths

|

1,684 sq ft

|

House

1606 SNELLING AVE, THE VILLAGES, FL, 321...
Community: The Villages®
Plantation at Leesburg 25335 CRANES ROOST CIR, LEESBURG, FL, 34..., Leesburg, FL 34748
$233,500

2 beds

|

2 baths

|

1,386 sq ft

|

House

25335 CRANES ROOST CIR, LEESBURG, FL, 34...
Plantation at Leesburg 5106 CHANTICLEER DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$513,000

3 beds

|

3 baths

|

3,112 sq ft

|

House

5106 CHANTICLEER DR, LEESBURG, FL, 34748
The Villages® 1529 STRATON WAY, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$435,000

3 beds

|

2 baths

|

1,918 sq ft

|

House

1529 STRATON WAY, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 858 PINCKNEY LN, THE VILLAGES, FL, 32162, The Villages, FL 32162
$1,649,000

3 beds

|

3 baths

|

3,921 sq ft

|

House

858 PINCKNEY LN, THE VILLAGES, FL, 32162
Community: The Villages®
Cindy Certified
2459 VALHALLA DR, TAVARES, FL, 32778, Tavares, FL 32778
$350,000

4 beds

|

2 baths

|

1,828 sq ft

|

House

2459 VALHALLA DR, TAVARES, FL, 32778
The Villages® 1773 BLACKWELL LN, THE VILLAGES, FL, 321..., The Villages, FL 32163
$359,900

3 beds

|

2 baths

|

1,426 sq ft

|

House

1773 BLACKWELL LN, THE VILLAGES, FL, 321...
Community: The Villages®
The Villages® 600 AUDREY LN, THE VILLAGES, FL, 32162, The Villages, FL 32162
$409,000

3 beds

|

2 baths

|

1,397 sq ft

|

Villa

600 AUDREY LN, THE VILLAGES, FL, 32162
Community: The Villages®
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
Del Webb Minneola 1552 SKYLINE HEIGHTS CIR, MINNEOLA, FL, ..., Minneola, FL 34715
$799,500

3 beds

|

4 baths

|

2,844 sq ft

|

House

1552 SKYLINE HEIGHTS CIR, MINNEOLA, FL, ...
Community: Del Webb Minneola
The Villages® 8142 SE 175TH COLUMBIA PL, THE VILLAGES,..., The Villages, FL 32162
$340,000

3 beds

|

2 baths

|

1,265 sq ft

|

House

8142 SE 175TH COLUMBIA PL, THE VILLAGES,...
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.

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1,145 homes
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