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Leesburg, FL 55+ active adult communities & homes for sale - Page 3

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® 3254 ZIPPERER WAY, THE VILLAGES, FL, 321..., The Villages, FL 32163
$550,000

3 beds

|

2 baths

|

1,654 sq ft

|

House

3254 ZIPPERER WAY, THE VILLAGES, FL, 321...
Community: The Villages®
Cindy Certified
34024 SKY BLOSSOM CIR, LEESBURG, FL, 347..., Leesburg, FL 34788
$331,500

4 beds

|

2 baths

|

1,850 sq ft

|

House

34024 SKY BLOSSOM CIR, LEESBURG, FL, 347...
The Villages® 2182 KAYLEE DR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$400,000

3 beds

|

2 baths

|

1,499 sq ft

|

House

2182 KAYLEE DR, THE VILLAGES, FL, 32162
Community: The Villages®
Spruce Creek South 10255 SE 178TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$239,000

2 beds

|

2 baths

|

1,248 sq ft

|

House

10255 SE 178TH PL, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
Pennbrooke Fairways 1040 EAGLES LNDG, LEESBURG, FL, 34748, Leesburg, FL 34748
$274,247

2 beds

|

2 baths

|

1,752 sq ft

|

House

1040 EAGLES LNDG, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
The Villages® 4398 PEZZULLO CIR, THE VILLAGES, FL, 321..., The Villages, FL 32163
$995,000

4 beds

|

3 baths

|

3,325 sq ft

|

House

4398 PEZZULLO CIR, THE VILLAGES, FL, 321...
Community: The Villages®
Pennbrooke Fairways 752 OLD OAKS LN, LEESBURG, FL, 34748, Leesburg, FL 34748
$239,900

3 beds

|

2 baths

|

1,620 sq ft

|

House

752 OLD OAKS LN, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Plantation at Leesburg 4952 HERON RUN CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$240,000

2 beds

|

2 baths

|

1,289 sq ft

|

House

4952 HERON RUN CIR, LEESBURG, FL, 34748
The Villages® 1103 MIONA SHORES DR, THE VILLAGES, FL, ..., The Villages, FL 32162
$1,585,000

4 beds

|

3 baths

|

4,272 sq ft

|

House

1103 MIONA SHORES DR, THE VILLAGES, FL, ...
Community: The Villages®
The Villages® 2334 AMBLER CIR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$699,816

3 beds

|

3 baths

|

2,243 sq ft

|

House

2334 AMBLER CIR, 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® 1647 DURAN DR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$272,000

2 beds

|

2 baths

|

1,121 sq ft

|

Villa

1647 DURAN DR, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 2155 BALDWIN RUN, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$400,000

3 beds

|

2 baths

|

1,488 sq ft

|

House

2155 BALDWIN RUN, THE VILLAGES, FL, 3216...
Community: The Villages®
Pennbrooke Fairways 32802 CROOKED OAKS LN, LEESBURG, FL, 347..., Leesburg, FL 34748
$250,000

3 beds

|

2 baths

|

1,604 sq ft

|

House

32802 CROOKED OAKS LN, LEESBURG, FL, 347...
Community: Pennbrooke Fairways
The Villages® 780 ADRIENNE WAY, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$410,000

3 beds

|

2 baths

|

1,357 sq ft

|

House

780 ADRIENNE WAY, THE VILLAGES, FL, 3216...
Community: The Villages®
Arlington Ridge 27033 WHITE PLAINS WAY, LEESBURG, FL, 34..., Leesburg, FL 34748
$240,000

2 beds

|

2 baths

|

1,323 sq ft

|

House

27033 WHITE PLAINS WAY, LEESBURG, FL, 34...
Community: Arlington Ridge
The Villages® 1700 NORFOLK AVE, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$476,000

3 beds

|

2 baths

|

1,920 sq ft

|

House

1700 NORFOLK AVE, 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® 1234 EAGLE RIDGE DR, THE VILLAGES, FL, 3..., The Villages, FL 32162
$315,000

2 beds

|

2 baths

|

1,156 sq ft

|

House

1234 EAGLE RIDGE DR, THE VILLAGES, FL, 3...
Community: The Villages®
Stonecrest 17681 SE 115TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$323,900

2 beds

|

3 baths

|

1,952 sq ft

|

House

17681 SE 115TH CT, SUMMERFIELD, FL, 3449...
Community: Stonecrest
The Villages® 17115 SE 93RD TELLFIER TER, THE VILLAGES..., The Villages, FL 32162
$495,000

3 beds

|

2 baths

|

2,036 sq ft

|

House

17115 SE 93RD TELLFIER TER, THE VILLAGES...
Community: The Villages®
Royal Highlands 21736 PRINCESS GRACE CT, LEESBURG, FL, 3..., Leesburg, FL 34748
$375,000

3 beds

|

2 baths

|

2,233 sq ft

|

House

21736 PRINCESS GRACE CT, LEESBURG, FL, 3...
Community: Royal Highlands
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® 3209 HAMPTON LN, THE VILLAGES, FL, 32162, The Villages, FL 32162
$399,000

3 beds

|

2 baths

|

1,640 sq ft

|

House

3209 HAMPTON LN, THE VILLAGES, FL, 32162
Community: The Villages®
Scottish Highlands 803 DUNDEE CIR 803, LEESBURG, FL, 34788, Leesburg, FL 34788
$229,900

2 beds

|

2 baths

|

1,436 sq ft

|

Condo

803 DUNDEE CIR 803, LEESBURG, FL, 34788
Community: Scottish Highlands
The Villages® 2459 LAUREL BAY LN, THE VILLAGES, FL, 32..., The Villages, FL 32162
$239,000

2 beds

|

2 baths

|

1,156 sq ft

|

House

2459 LAUREL BAY LN, THE VILLAGES, FL, 32...
Community: The Villages®
Plantation at Leesburg 25078 RIVERWALK DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$279,900

2 beds

|

2 baths

|

1,549 sq ft

|

House

25078 RIVERWALK DR, LEESBURG, FL, 34748
The Villages® 1318 BALBOA CT, THE VILLAGES, FL, 32159, The Villages, FL 32159
$274,500

2 beds

|

2 baths

|

978 sq ft

|

Villa

1318 BALBOA CT, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 16870 SE 96TH CHAPELWOOD CIR, THE VILLAG..., The Villages, FL 32162
$274,900

2 beds

|

2 baths

|

1,160 sq ft

|

House

16870 SE 96TH CHAPELWOOD CIR, THE VILLAG...
Community: The Villages®
The Villages® 1693 MOUNT CROGHAN TRL, THE VILLAGES, FL..., The Villages, FL 32162
$455,000

3 beds

|

2 baths

|

1,927 sq ft

|

House

1693 MOUNT CROGHAN TRL, THE VILLAGES, FL...
Community: The Villages®
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
The Villages® 9595 SE 171ST ARGYLL ST, THE VILLAGES, F..., The Villages, FL 32162
$345,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

9595 SE 171ST ARGYLL ST, THE VILLAGES, F...
Community: The Villages®
Cindy Certified
4419 LINWOOD TRACE LN, CLERMONT, FL, 347..., Clermont, FL 34711
$615,000

4 beds

|

3 baths

|

2,105 sq ft

|

House

4419 LINWOOD TRACE LN, CLERMONT, FL, 347...
The Villages® 5099 NE 124TH PL, OXFORD, FL, 34484, Oxford, FL 34484
$397,500

3 beds

|

3 baths

|

2,491 sq ft

|

House

5099 NE 124TH PL, OXFORD, FL, 34484
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® 1648 PENNECAMP DR, THE VILLAGES, FL, 321..., The Villages, FL 32162
$429,900

3 beds

|

2 baths

|

1,753 sq ft

|

House

1648 PENNECAMP DR, THE VILLAGES, FL, 321...
Community: The Villages®
Legacy of Leesburg 5401 AURORA DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$298,800

3 beds

|

2 baths

|

1,621 sq ft

|

House

5401 AURORA DR, LEESBURG, FL, 34748
Community: Legacy of Leesburg
Stonecrest 12173 SE 178TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$310,000

3 beds

|

2 baths

|

1,636 sq ft

|

House

12173 SE 178TH ST, SUMMERFIELD, FL, 3449...
Community: Stonecrest
The Villages® 3144 ROBBS RD, THE VILLAGES, FL, 32163, The Villages, FL 32163
$392,000

3 beds

|

2 baths

|

1,628 sq ft

|

Villa

3144 ROBBS RD, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 3067 SOUTHERN TRCE, THE VILLAGES, FL, 32..., The Villages, FL 32162
$369,000

3 beds

|

2 baths

|

1,632 sq ft

|

House

3067 SOUTHERN TRCE, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 3275 KILARNY PL, THE VILLAGES, FL, 32163, The Villages, FL 32163
$525,000

3 beds

|

2 baths

|

1,938 sq ft

|

House

3275 KILARNY PL, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 3208 HOPEWELL ST, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$399,900

3 beds

|

2 baths

|

1,946 sq ft

|

House

3208 HOPEWELL ST, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 1318 GREENVILLE WAY, THE VILLAGES, FL, 3..., The Villages, FL 32162
$450,000

3 beds

|

2 baths

|

1,927 sq ft

|

House

1318 GREENVILLE WAY, THE VILLAGES, FL, 3...
Community: The Villages®
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
Summit Chase Villas 12441 ORANGEWOOD CIR, TAVARES, FL, 32778, Tavares, FL 32778
$198,500

2 beds

|

2 baths

|

986 sq ft

|

House

12441 ORANGEWOOD CIR, TAVARES, FL, 32778
Community: Summit Chase Villas
Stonecrest 10957 SE 170TH LANE RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$289,900

3 beds

|

2 baths

|

1,381 sq ft

|

House

10957 SE 170TH LANE RD, SUMMERFIELD, FL,...
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.

Frequently Asked Questions


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1,145 homes
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