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Leesburg, FL 55+ active adult communities & homes for sale - Page 24

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
Spruce Creek South 17814 SE 107TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$249,900

3 beds

|

2 baths

|

1,450 sq ft

|

House

17814 SE 107TH TER, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
The Villages® 3541 ROANOKE ST, THE VILLAGES, FL, 32162, The Villages, FL 32162
$269,000

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

3541 ROANOKE ST, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 1795 HAGOOD LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$467,500

3 beds

|

2 baths

|

1,770 sq ft

|

House

1795 HAGOOD LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
Kings Ridge 4390 SAMBOURNE ST, CLERMONT, FL, 34711, Clermont, FL 34711
$289,900

2 beds

|

2 baths

|

1,363 sq ft

|

House

4390 SAMBOURNE ST, CLERMONT, FL, 34711
Community: Kings Ridge
The Villages® 2696 MIDLAND TER, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$850,000

3 beds

|

2 baths

|

2,133 sq ft

|

House

2696 MIDLAND TER, THE VILLAGES, FL, 3216...
Community: The Villages®
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
Cindy Certified
573 KISTLER CIR, CLERMONT, FL, 34715, Clermont, FL 34715
$415,000

3 beds

|

2 baths

|

2,071 sq ft

|

House

573 KISTLER CIR, CLERMONT, FL, 34715
The Villages® 1969 HAGOOD LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$400,000

3 beds

|

2 baths

|

2,000 sq ft

|

House

1969 HAGOOD LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 1648 ABASCO CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$329,900

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

1648 ABASCO CT, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 991 BARRYMOORE LOOP, THE VILLAGES, FL, 3..., The Villages, FL 32162
$399,900

3 beds

|

2 baths

|

1,527 sq ft

|

House

991 BARRYMOORE LOOP, THE VILLAGES, FL, 3...
Community: The Villages®
Trilogy® Orlando 115 CRESCENT MOON DR, GROVELAND, FL, 347..., Groveland, FL 34736
$295,000

3 beds

|

2 baths

|

1,856 sq ft

|

House

115 CRESCENT MOON DR, GROVELAND, FL, 347...
Community: Trilogy® Orlando
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® 207 DESOTA CT, THE VILLAGES, FL, 32159, The Villages, FL 32159
$450,000

3 beds

|

2 baths

|

1,889 sq ft

|

House

207 DESOTA CT, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 1000 KENOVA AVE, THE VILLAGES, FL, 32162, The Villages, FL 32162
$320,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

1000 KENOVA AVE, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 2013 SANTO DOMINGO DR, THE VILLAGES, FL,..., The Villages, FL 32159
$425,000

3 beds

|

2 baths

|

2,015 sq ft

|

House

2013 SANTO DOMINGO DR, THE VILLAGES, FL,...
Community: The Villages®
Royal Highlands 4841 GLEN COE ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$280,000

3 beds

|

2 baths

|

2,197 sq ft

|

House

4841 GLEN COE ST, LEESBURG, FL, 34748
Community: Royal Highlands
The Villages® 1420 FAIRWAY ST, THE VILLAGES, FL, 32162, The Villages, FL 32162
$289,560

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

1420 FAIRWAY ST, THE VILLAGES, FL, 32162
Community: The Villages®
Trilogy® Orlando 508 NARROW VIEW LN, GROVELAND, FL, 34736, Groveland, FL 34736
$430,000

2 beds

|

2 baths

|

1,835 sq ft

|

House

508 NARROW VIEW LN, GROVELAND, FL, 34736
Community: Trilogy® Orlando
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
Royal Harbor 6274 SAILBOAT AVE, TAVARES, FL, 32778, Tavares, FL 32778
$825,000

4 beds

|

3 baths

|

3,323 sq ft

|

House

6274 SAILBOAT AVE, TAVARES, FL, 32778
Community: Royal Harbor
Plantation at Leesburg 24947 CRANES ROOST CIR, LEESBURG, FL, 34..., Leesburg, FL 34748
$205,000

3 beds

|

2 baths

|

1,653 sq ft

|

House

24947 CRANES ROOST CIR, LEESBURG, FL, 34...
Kings Ridge 4127 KINGSLEY ST, CLERMONT, FL, 34711, Clermont, FL 34711
$349,000

2 beds

|

2 baths

|

1,884 sq ft

|

House

4127 KINGSLEY ST, CLERMONT, FL, 34711
Community: Kings Ridge
Kings Ridge 3445 CAPLAND AVE, CLERMONT, FL, 34711, Clermont, FL 34711
$389,000

3 beds

|

2 baths

|

1,816 sq ft

|

House

3445 CAPLAND AVE, CLERMONT, FL, 34711
Community: Kings Ridge
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® 7631 SE 170TH LONGVIEW LN, THE VILLAGES,..., The Villages, FL 32162
$269,000

2 beds

|

2 baths

|

1,186 sq ft

|

Villa

7631 SE 170TH LONGVIEW LN, THE VILLAGES,...
Community: The Villages®
The Villages® 2306 NACKMAN PL, THE VILLAGES, FL, 32162, The Villages, FL 32162
$390,000

3 beds

|

2 baths

|

1,397 sq ft

|

Villa

2306 NACKMAN PL, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 1936 NEEDLEWOOD LN, THE VILLAGES, FL, 32..., The Villages, FL 32162
$550,000

3 beds

|

2 baths

|

1,602 sq ft

|

Villa

1936 NEEDLEWOOD LN, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 17705 SE 93RD HAWTHORNE AVE, THE VILLAGE..., The Villages, FL 32162
$308,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

17705 SE 93RD HAWTHORNE AVE, THE VILLAGE...
Community: The Villages®
Plantation at Leesburg 24511 BOCAGE WAY, LEESBURG, FL, 34748, Leesburg, FL 34748
$415,000

3 beds

|

3 baths

|

2,684 sq ft

|

House

24511 BOCAGE WAY, LEESBURG, FL, 34748
The Villages® 16689 SE 78TH LIVE OAK AVE, THE VILLAGES..., The Villages, FL 32162
$348,900

3 beds

|

2 baths

|

1,478 sq ft

|

House

16689 SE 78TH LIVE OAK AVE, THE VILLAGES...
Community: The Villages®
Arlington Ridge 4025 ARLINGTON RIDGE BLVD, LEESBURG, FL,..., Leesburg, FL 34748
$374,900

3 beds

|

2 baths

|

1,719 sq ft

|

House

4025 ARLINGTON RIDGE BLVD, LEESBURG, FL,...
Community: Arlington Ridge
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
The Villages® 4348 TUSCALOOSA PATH, THE VILLAGES, FL, ..., The Villages, FL 32163
$539,900

3 beds

|

3 baths

|

1,905 sq ft

|

House

4348 TUSCALOOSA PATH, THE VILLAGES, FL, ...
Community: The Villages®
The Villages® 1106 EBLING LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$499,000

3 beds

|

2 baths

|

1,569 sq ft

|

House

1106 EBLING LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 312 S TIMBER TRL, WILDWOOD, FL, 34785, Wildwood, FL 34785
$124,500

2 beds

|

2 baths

|

1,144 sq ft

|

Manufactured Home

312 S TIMBER TRL, WILDWOOD, FL, 34785
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 27215 ROANOKE DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$355,000

3 beds

|

2 baths

|

1,709 sq ft

|

House

27215 ROANOKE DR, LEESBURG, FL, 34748
Community: Arlington Ridge
Heritage Hills 2892 SANDY CAY ST, CLERMONT, FL, 34711, Clermont, FL 34711
$520,000

3 beds

|

3 baths

|

2,597 sq ft

|

House

2892 SANDY CAY ST, CLERMONT, FL, 34711
Community: Heritage Hills
Plantation at Leesburg 4810 SABLE RIDGE CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$335,000

2 beds

|

2 baths

|

2,350 sq ft

|

House

4810 SABLE RIDGE CT, LEESBURG, FL, 34748
Pennbrooke Fairways 32914 CROOKED OAKS LN, LEESBURG, FL, 347..., Leesburg, FL 34748
$259,900

3 beds

|

2 baths

|

1,745 sq ft

|

House

32914 CROOKED OAKS LN, LEESBURG, FL, 347...
Community: Pennbrooke Fairways
Trilogy® Orlando 111 FLAME VINE WAY, GROVELAND, FL, 34736, Groveland, FL 34736
$315,000

3 beds

|

2 baths

|

1,848 sq ft

|

House

111 FLAME VINE WAY, GROVELAND, FL, 34736
Community: Trilogy® Orlando
The Villages® 1256 AVENIDA DE LAS CASAS, LADY LAKE, FL..., Lady Lake, FL 32159
$409,750

2 beds

|

2 baths

|

1,361 sq ft

|

Condo

1256 AVENIDA DE LAS CASAS, LADY LAKE, FL...
Community: The Villages®
The Villages® 2165 GORDON PATH, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$1,000,000

3 beds

|

3 baths

|

2,581 sq ft

|

House

2165 GORDON PATH, THE VILLAGES, FL, 3216...
Community: The Villages®
Del Webb Minneola 1333 ZESTY CITRUS LN, MINNEOLA, FL, 3471..., Minneola, FL 34715
$564,000

3 beds

|

2 baths

|

1,690 sq ft

|

House

1333 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
Legacy of Leesburg 27111 NOSTALGIA DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$279,000

3 beds

|

2 baths

|

1,477 sq ft

|

House

27111 NOSTALGIA DR, LEESBURG, FL, 34748
Community: Legacy of Leesburg
The Villages® 1809 DAFFODIL LN, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$170,000

2 beds

|

1 baths

|

936 sq ft

|

Manufactured Home

1809 DAFFODIL LN, 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.

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1,145 homes
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