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Leesburg, FL 55+ active adult communities & homes for sale - Page 19

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
Heritage - The Cottages of Sanders Grove 6201 SANDERS GROVE CIR 1, OKAHUMKA, FL, ..., Okahumka, FL 34762
$341,535

4 beds

|

2 baths

|

1,625 sq ft

|

House

6201 SANDERS GROVE CIR 1, OKAHUMKA, FL, ...
Heritage - The Cottages of Sanders Grove 5719 HIAWASSEE RD 1, OKAHUMKA, FL, 34762, Okahumka, FL 34762
$329,990

4 beds

|

2 baths

|

1,625 sq ft

|

House

5719 HIAWASSEE RD 1, OKAHUMKA, FL, 34762
Heritage - The Cottages of Sanders Grove 6213 SANDERS GROVE CIR, OKAHUMKA, FL, 34..., Okahumka, FL 34762
$332,595

4 beds

|

2 baths

|

1,625 sq ft

|

House

6213 SANDERS GROVE CIR, OKAHUMKA, FL, 34...
Heritage - The Cottages of Sanders Grove 6205 SANDERS GROVE CIR 1, OKAHUMKA, FL, ..., Okahumka, FL 34762
$323,286

3 beds

|

2 baths

|

1,407 sq ft

|

House

6205 SANDERS GROVE CIR 1, OKAHUMKA, FL, ...
Heritage - The Cottages of Sanders Grove 5727 HIAWASSEE RD, OKAHUMKA, FL, 34762, Okahumka, FL 34762
$309,990

3 beds

|

2 baths

|

1,407 sq ft

|

House

5727 HIAWASSEE RD, OKAHUMKA, FL, 34762
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
The Villages® 714 CIMARRON AVE, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$998,500

3 beds

|

2 baths

|

2,774 sq ft

|

House

714 CIMARRON AVE, THE VILLAGES, FL, 3215...
Community: The Villages®
The Villages® 992 RIDGELAND PATH, THE VILLAGES, FL, 32..., The Villages, FL 32162
$425,000

3 beds

|

2 baths

|

1,703 sq ft

|

House

992 RIDGELAND PATH, THE VILLAGES, FL, 32...
Community: The Villages®
Esplanade at Highland Ranch 2612 FRAZEEK CT, CLERMONT, FL, 34715, Clermont, FL 34715
$435,000

3 beds

|

3 baths

|

1,827 sq ft

|

House

2612 FRAZEEK CT, CLERMONT, FL, 34715
The Villages® 2875 RAIN LILY LOOP, THE VILLAGES, FL, 3..., The Villages, FL 32163
$624,000

3 beds

|

2 baths

|

1,965 sq ft

|

House

2875 RAIN LILY LOOP, THE VILLAGES, FL, 3...
Community: The Villages®
Plantation at Leesburg 4438 RIVER RIDGE DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$280,000

2 beds

|

2 baths

|

1,871 sq ft

|

House

4438 RIVER RIDGE DR, LEESBURG, FL, 34748
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® 17946 SE 87TH MELROSE CT, THE VILLAGES, ..., The Villages, FL 32162
$445,000

3 beds

|

2 baths

|

2,013 sq ft

|

House

17946 SE 87TH MELROSE CT, THE VILLAGES, ...
Community: The Villages®
Cindy Certified
26180 FEATHERGRASS CIR, LEESBURG, FL, 34..., Leesburg, FL 34748
$285,000

3 beds

|

2 baths

|

1,432 sq ft

|

House

26180 FEATHERGRASS CIR, LEESBURG, FL, 34...
The Villages® 2311 GLADE RUN, THE VILLAGES, FL, 32162, The Villages, FL 32162
$490,000

3 beds

|

2 baths

|

1,927 sq ft

|

House

2311 GLADE RUN, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 728 CONGAREE LOOP, THE VILLAGES, FL, 321..., The Villages, FL 32163
$819,900

3 beds

|

3 baths

|

2,829 sq ft

|

House

728 CONGAREE LOOP, THE VILLAGES, FL, 321...
Community: The Villages®
Spruce Creek South 17676 SE 102ND CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$265,000

3 beds

|

3 baths

|

1,988 sq ft

|

House

17676 SE 102ND CIR, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
The Villages® 13718 COUNTY RD, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$285,000

5 beds

|

3 baths

|

2,176 sq ft

|

Manufactured Home

13718 COUNTY RD, LADY LAKE, FL, 32159
Community: The Villages®
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
The Villages® 5217 CAMBRIDGE CT, WILDWOOD, FL, 34785, Wildwood, FL 34785
$170,000

2 beds

|

2 baths

|

1,352 sq ft

|

Manufactured Home

5217 CAMBRIDGE CT, WILDWOOD, FL, 34785
Community: The Villages®
Scottish Highlands 1117 BEN HOPE DR, LEESBURG, FL, 34788, Leesburg, FL 34788
$315,000

2 beds

|

3 baths

|

2,280 sq ft

|

House

1117 BEN HOPE DR, LEESBURG, FL, 34788
Community: Scottish Highlands
The Villages® 1012 DIEGO CT, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$414,900

3 beds

|

2 baths

|

1,976 sq ft

|

House

1012 DIEGO CT, LADY LAKE, FL, 32159
Community: The Villages®
Highland Lakes 27305 RACQUET CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$325,000

3 beds

|

2 baths

|

2,886 sq ft

|

House

27305 RACQUET CIR, LEESBURG, FL, 34748
Community: Highland Lakes
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® 1230 DESILVA ST, THE VILLAGES, FL, 32159, The Villages, FL 32159
$492,000

3 beds

|

2 baths

|

1,842 sq ft

|

House

1230 DESILVA ST, THE VILLAGES, FL, 32159
Community: The Villages®
Plantation at Leesburg 3851 MANOR OAKS CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$339,999

3 beds

|

3 baths

|

2,555 sq ft

|

House

3851 MANOR OAKS CT, LEESBURG, FL, 34748
Scottish Highlands 32 GORDON CT, LEESBURG, FL, 34788, Leesburg, FL 34788
$252,000

2 beds

|

2 baths

|

1,528 sq ft

|

House

32 GORDON CT, LEESBURG, FL, 34788
Community: Scottish Highlands
Cindy Certified
26220 FEATHERGRASS CIR, LEESBURG, FL, 34..., Leesburg, FL 34748
$285,000

3 beds

|

2 baths

|

1,432 sq ft

|

House

26220 FEATHERGRASS CIR, LEESBURG, FL, 34...
Cindy Certified
4475 CAICOS DR, TAVARES, FL, 32778, Tavares, FL 32778
$225,000

3 beds

|

2 baths

|

1,528 sq ft

|

House

4475 CAICOS DR, TAVARES, FL, 32778
Summit Greens 2361 PRAIRIE DUNES, CLERMONT, FL, 34711, Clermont, FL 34711
$344,000

2 beds

|

2 baths

|

1,565 sq ft

|

House

2361 PRAIRIE DUNES, CLERMONT, FL, 34711
Community: Summit Greens
Royal Highlands 4646 INVERNESS DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$289,900

3 beds

|

2 baths

|

2,020 sq ft

|

House

4646 INVERNESS DR, LEESBURG, FL, 34748
Community: Royal Highlands
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
The Villages® 3461 EARL WAY, THE VILLAGES, FL, 32163, The Villages, FL 32163
$545,000

3 beds

|

2 baths

|

1,903 sq ft

|

House

3461 EARL WAY, THE VILLAGES, FL, 32163
Community: The Villages®
Scottish Highlands 1305 MORAY CT, LEESBURG, FL, 34788, Leesburg, FL 34788
$212,900

3 beds

|

2 baths

|

1,569 sq ft

|

House

1305 MORAY CT, LEESBURG, FL, 34788
Community: Scottish Highlands
The Villages® 1213 EL ESPARZA LN, THE VILLAGES, FL, 32..., The Villages, FL 32159
$379,900

3 beds

|

2 baths

|

1,404 sq ft

|

House

1213 EL ESPARZA LN, THE VILLAGES, 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.
The Villages® 1203 GRANADA CT, THE VILLAGES, FL, 32159, The Villages, FL 32159
$229,999

2 beds

|

2 baths

|

1,300 sq ft

|

Manufactured Home

1203 GRANADA CT, THE VILLAGES, FL, 32159
Community: The Villages®
Cindy Certified
2202 WILDBERRY WAY WAY, MINNEOLA, FL, 34..., Minneola, FL 34715
$440,000

3 beds

|

2 baths

|

1,483 sq ft

|

House

2202 WILDBERRY WAY WAY, MINNEOLA, FL, 34...
Plantation at Leesburg 24044 PEEKSKILL ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$399,000

2 beds

|

3 baths

|

2,634 sq ft

|

House

24044 PEEKSKILL ST, LEESBURG, FL, 34748
The Villages® 791 ENISGROVE WAY, THE VILLAGES, FL, 321..., The Villages, FL 32163
$439,000

3 beds

|

2 baths

|

1,956 sq ft

|

House

791 ENISGROVE WAY, THE VILLAGES, FL, 321...
Community: The Villages®
Stonecrest 17585 SE 122ND TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$649,000

3 beds

|

3 baths

|

2,087 sq ft

|

House

17585 SE 122ND TER, SUMMERFIELD, FL, 344...
Community: Stonecrest
Plantation at Leesburg 25517 LAUREL VALLEY RD, LEESBURG, FL, 34..., Leesburg, FL 34748
$369,000

3 beds

|

2 baths

|

2,381 sq ft

|

House

25517 LAUREL VALLEY RD, LEESBURG, FL, 34...
Lakeside Landings 5011 BELTED KINGFISHER DR, OXFORD, FL, 3..., Oxford, FL 34484
$369,900

3 beds

|

2 baths

|

1,832 sq ft

|

House

5011 BELTED KINGFISHER DR, OXFORD, FL, 3...
Community: Lakeside Landings
The Villages® 712 ARTESIA AVE, THE VILLAGES, FL, 32162, The Villages, FL 32162
$295,000

2 beds

|

2 baths

|

1,148 sq ft

|

House

712 ARTESIA AVE, 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
The Villages® 1550 HILLCREST DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$189,900

2 beds

|

2 baths

|

1,196 sq ft

|

Manufactured Home

1550 HILLCREST DR, THE VILLAGES, FL, 321...
Community: The Villages®
Stonecrest 11363 SE 177TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$350,000

3 beds

|

3 baths

|

2,637 sq ft

|

House

11363 SE 177TH LN, 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.

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1,145 homes
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