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Leesburg, FL 55+ active adult communities & homes for sale - Page 14

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® 2527 BOTELLO AVE, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$305,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

2527 BOTELLO AVE, THE VILLAGES, FL, 3216...
Community: The Villages®
Stonecrest 11734 SE 173RD LANE RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$345,000

2 beds

|

2 baths

|

1,630 sq ft

|

House

11734 SE 173RD LANE RD, SUMMERFIELD, FL,...
Community: Stonecrest
Spruce Creek South 17790 SE 101ST CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$273,900

3 beds

|

2 baths

|

1,910 sq ft

|

House

17790 SE 101ST CT, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
Trilogy® Orlando 381 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736
$319,900

2 beds

|

2 baths

|

1,479 sq ft

|

House

381 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
Stonecrest 11137 SE 174TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$258,000

3 beds

|

2 baths

|

1,453 sq ft

|

House

11137 SE 174TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
The Villages® 476 ISLAND HOUSE PATH, THE VILLAGES, FL,..., The Villages, FL 32163
$400,000

3 beds

|

2 baths

|

1,618 sq ft

|

House

476 ISLAND HOUSE PATH, THE VILLAGES, FL,...
Community: The Villages®
The Villages® 2494 FLINTSHIRE AVE, THE VILLAGES, FL, 3..., The Villages, FL 32162
$395,000

3 beds

|

2 baths

|

1,644 sq ft

|

House

2494 FLINTSHIRE AVE, THE VILLAGES, FL, 3...
Community: The Villages®
The Villages® 2732 PRIVADA DR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$299,999

3 beds

|

2 baths

|

1,392 sq ft

|

House

2732 PRIVADA DR, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 1532 W SCHWARTZ BLVD, LADY LAKE, FL, 321..., Lady Lake, FL 32159
$224,900

2 beds

|

2 baths

|

1,092 sq ft

|

Modular

1532 W SCHWARTZ BLVD, LADY LAKE, FL, 321...
Community: The Villages®
Cresswind at Hammock Oaks 533 HAMMOCK OAKS BLVD, LADY LAKE, FL, 32..., Lady Lake, FL 32159
$475,990

3 beds

|

3 baths

|

2,129 sq ft

|

House

533 HAMMOCK OAKS BLVD, LADY LAKE, FL, 32...
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.
Cresswind at Hammock Oaks 545 HAMMOCK OAKS BLVD, LADY LAKE, FL, 32..., Lady Lake, FL 32159
$495,990

3 beds

|

3 baths

|

2,289 sq ft

|

House

545 HAMMOCK OAKS BLVD, LADY LAKE, FL, 32...
Cresswind at Hammock Oaks 419 VERONA WAY, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$371,990

2 beds

|

2 baths

|

1,434 sq ft

|

House

419 VERONA WAY, LADY LAKE, FL, 32159
The Villages® 3578 OBRIEN PL, THE VILLAGES, FL, 32163, The Villages, FL 32163
$529,000

3 beds

|

2 baths

|

1,943 sq ft

|

House

3578 OBRIEN PL, THE VILLAGES, FL, 32163
Community: The Villages®
Cresswind at Hammock Oaks 423 VERONA WAY, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$394,990

3 beds

|

2 baths

|

1,724 sq ft

|

House

423 VERONA WAY, LADY LAKE, FL, 32159
The Villages® 16947 SE 93RD CUTHBERT CIR, THE VILLAGES..., The Villages, FL 32162
$332,000

3 beds

|

2 baths

|

1,497 sq ft

|

House

16947 SE 93RD CUTHBERT CIR, THE VILLAGES...
Community: The Villages®
Cresswind at Lake Harris 1732 POINT GRACE RD, TAVARES, FL, 32778, Tavares, FL 32778
$516,990

3 beds

|

3 baths

|

2,129 sq ft

|

House

1732 POINT GRACE RD, TAVARES, FL, 32778
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
The Villages® 16573 SE 77TH NORTHRIDGE CT, THE VILLAGE..., The Villages, FL 32162
$400,000

3 beds

|

2 baths

|

1,902 sq ft

|

House

16573 SE 77TH NORTHRIDGE CT, THE VILLAGE...
Community: The Villages®
Royal Harbor 5964 BRITTANIA BLVD, TAVARES, FL, 32778, Tavares, FL 32778
$325,000

2 beds

|

3 baths

|

2,080 sq ft

|

House

5964 BRITTANIA BLVD, TAVARES, FL, 32778
Community: Royal Harbor
Stonecrest 17408 SE 121ST CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$289,900

3 beds

|

2 baths

|

1,733 sq ft

|

House

17408 SE 121ST CIR, SUMMERFIELD, FL, 344...
Community: Stonecrest
The Villages® 556 KINGSTON WAY, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$424,700

3 beds

|

2 baths

|

2,413 sq ft

|

House

556 KINGSTON WAY, 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.
The Villages® 2417 TATUM TER, THE VILLAGES, FL, 32162, The Villages, FL 32162
$389,000

3 beds

|

2 baths

|

1,792 sq ft

|

House

2417 TATUM TER, THE VILLAGES, FL, 32162
Community: The Villages®
Stonecrest 17742 SE 114TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$249,900

2 beds

|

3 baths

|

1,675 sq ft

|

House

17742 SE 114TH CT, SUMMERFIELD, FL, 3449...
Community: Stonecrest
The Villages® 1969 HARTFORD PATH, THE VILLAGES, FL, 32..., The Villages, FL 32162
$799,000

3 beds

|

2 baths

|

2,314 sq ft

|

House

1969 HARTFORD PATH, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 2334 ROSE ARBOR ST, THE VILLAGES, FL, 32..., The Villages, FL 32163
$499,900

3 beds

|

2 baths

|

1,695 sq ft

|

Villa

2334 ROSE ARBOR ST, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 301 KLAMUT CT, THE VILLAGES, FL, 32163, The Villages, FL 32163
$329,900

3 beds

|

2 baths

|

1,392 sq ft

|

House

301 KLAMUT CT, THE VILLAGES, FL, 32163
Community: The Villages®
Scottish Highlands 1410 NEW ABBEY AVE, LEESBURG, FL, 34788, Leesburg, FL 34788
$269,990

2 beds

|

2 baths

|

1,663 sq ft

|

House

1410 NEW ABBEY AVE, LEESBURG, FL, 34788
Community: Scottish Highlands
Pennbrooke Fairways 1009 FOREST BREEZE PATH, LEESBURG, FL, 3..., Leesburg, FL 34748
$279,000

3 beds

|

2 baths

|

1,921 sq ft

|

House

1009 FOREST BREEZE PATH, LEESBURG, FL, 3...
Community: Pennbrooke Fairways
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
Heritage Hills 3650 LIMESTONE ST, CLERMONT, FL, 34711, Clermont, FL 34711
$384,000

3 beds

|

2 baths

|

1,677 sq ft

|

House

3650 LIMESTONE ST, CLERMONT, FL, 34711
Community: Heritage Hills
The Villages® 1519 MARTINEZ DR, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$399,900

2 beds

|

3 baths

|

2,138 sq ft

|

Villa

1519 MARTINEZ DR, THE VILLAGES, FL, 3215...
Community: The Villages®
Kings Ridge 4224 SNOWDON ST, CLERMONT, FL, 34711, Clermont, FL 34711
$292,000

2 beds

|

2 baths

|

1,170 sq ft

|

House

4224 SNOWDON ST, 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.
Heritage Hills 3516 KINLEY BROOKE LN, CLERMONT, FL, 347..., Clermont, FL 34711
$420,000

3 beds

|

2 baths

|

1,879 sq ft

|

House

3516 KINLEY BROOKE LN, CLERMONT, FL, 347...
Community: Heritage Hills
The Villages® 7815 SE 166TH HIBERNIA LN, THE VILLAGES,..., The Villages, FL 32162
$375,000

3 beds

|

2 baths

|

1,854 sq ft

|

House

7815 SE 166TH HIBERNIA LN, THE VILLAGES,...
Community: The Villages®
The Villages® 2841 APACHE CT, THE VILLAGES, FL, 32163, The Villages, FL 32163
$920,000

3 beds

|

2 baths

|

2,310 sq ft

|

House

2841 APACHE CT, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 5738 CARLEY LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$475,000

3 beds

|

2 baths

|

2,015 sq ft

|

House

5738 CARLEY LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 5844 MARSH CT, THE VILLAGES, FL, 32163, The Villages, FL 32163
$259,500

1 beds

|

1 baths

|

938 sq ft

|

Villa

5844 MARSH CT, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 973 YORK TER, THE VILLAGES, FL, 32162, The Villages, FL 32162
$274,900

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

973 YORK TER, THE VILLAGES, FL, 32162
Community: The Villages®
Highland Lakes 26616 WIMBLEDON ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$275,000

3 beds

|

2 baths

|

2,254 sq ft

|

House

26616 WIMBLEDON ST, LEESBURG, FL, 34748
Community: Highland Lakes
The Villages® 371 ARBELLA LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$334,900

2 beds

|

2 baths

|

1,143 sq ft

|

House

371 ARBELLA LOOP, 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
The Villages® 3437 GREENACRES TER, THE VILLAGES, FL, 3..., The Villages, FL 32163
$299,000

2 beds

|

2 baths

|

1,130 sq ft

|

House

3437 GREENACRES TER, THE VILLAGES, FL, 3...
Community: The Villages®
The Villages® 17766 SE 91ST POPLAR TER, THE VILLAGES, ..., The Villages, FL 32162
$288,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

17766 SE 91ST POPLAR TER, 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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