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Leesburg, FL 55+ active adult communities & homes for sale - Page 27

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® 2679 LANTANA AVE, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$499,000

3 beds

|

2 baths

|

1,966 sq ft

|

House

2679 LANTANA AVE, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 258 ARBELLA LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$298,000

2 beds

|

2 baths

|

1,130 sq ft

|

House

258 ARBELLA LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
Legacy of Leesburg 27106 GREENFLY ORCHID LN, LEESBURG, FL, ..., Leesburg, FL 34748
$289,900

3 beds

|

2 baths

|

1,541 sq ft

|

House

27106 GREENFLY ORCHID LN, LEESBURG, FL, ...
Community: Legacy of Leesburg
Cindy Certified
4049 PINNACLE PL, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$579,900

3 beds

|

3 baths

|

2,505 sq ft

|

House

4049 PINNACLE PL, LADY LAKE, FL, 32159
Royal Harbor 6105 DORY WAY, TAVARES, FL, 32778, Tavares, FL 32778
$295,000

3 beds

|

2 baths

|

1,556 sq ft

|

House

6105 DORY WAY, TAVARES, FL, 32778
Community: Royal Harbor
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
The Villages® 17470 SE 93RD VINE AVE, THE VILLAGES, FL..., The Villages, FL 32162
$245,000

2 beds

|

2 baths

|

1,172 sq ft

|

Villa

17470 SE 93RD VINE AVE, THE VILLAGES, FL...
Community: The Villages®
Trilogy® Orlando 334 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736
$425,000

2 beds

|

2 baths

|

1,967 sq ft

|

House

334 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
Royal Harbor 5245 CHINA SEA DR, TAVARES, FL, 32778, Tavares, FL 32778
$326,000

3 beds

|

2 baths

|

1,862 sq ft

|

House

5245 CHINA SEA DR, TAVARES, FL, 32778
Community: Royal Harbor
Trilogy® Orlando 374 SALT MARSH LN, GROVELAND, FL, 34736, Groveland, FL 34736
$326,000

2 beds

|

2 baths

|

1,624 sq ft

|

House

374 SALT MARSH LN, GROVELAND, FL, 34736
Community: Trilogy® Orlando
Stonecrest 11900 SE 178TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$357,000

3 beds

|

2 baths

|

1,613 sq ft

|

House

11900 SE 178TH ST, 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.
Trilogy® Orlando 115 SALT MARSH LN, GROVELAND, FL, 34736, Groveland, FL 34736
$418,000

2 beds

|

2 baths

|

1,940 sq ft

|

House

115 SALT MARSH LN, GROVELAND, FL, 34736
Community: Trilogy® Orlando
Plantation at Leesburg 3810 ST EMMA CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$334,900

3 beds

|

4 baths

|

2,473 sq ft

|

House

3810 ST EMMA CT, LEESBURG, FL, 34748
The Villages® 16938 SE 94TH SUNNYBROOK CIR, THE VILLAG..., The Villages, FL 32162
$255,000

2 beds

|

2 baths

|

1,163 sq ft

|

Villa

16938 SE 94TH SUNNYBROOK CIR, THE VILLAG...
Community: The Villages®
Esplanade at Highland Ranch 1282 ZEEK RIDGE ST, CLERMONT, FL, 34715, Clermont, FL 34715
$415,500

2 beds

|

2 baths

|

1,710 sq ft

|

House

1282 ZEEK RIDGE ST, CLERMONT, FL, 34715
Heritage Hills 2876 SANDY CAY ST, CLERMONT, FL, 34711, Clermont, FL 34711
$499,900

3 beds

|

2 baths

|

2,123 sq ft

|

House

2876 SANDY CAY ST, CLERMONT, FL, 34711
Community: Heritage Hills
The Villages® 5186 NE 122ND BLVD, OXFORD, FL, 34484, Oxford, FL 34484
$280,000

3 beds

|

4 baths

|

1,929 sq ft

|

House

5186 NE 122ND BLVD, OXFORD, FL, 34484
Community: The Villages®
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
Stonecrest 17584 SE 119TH CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$285,000

3 beds

|

2 baths

|

1,482 sq ft

|

House

17584 SE 119TH CIR, SUMMERFIELD, FL, 344...
Community: Stonecrest
Cindy Certified
3058 GRANITE RIDGE AVE, MINNEOLA, FL, 34..., Minneola, FL 34715
$509,490

4 beds

|

3 baths

|

2,366 sq ft

|

House

3058 GRANITE RIDGE AVE, MINNEOLA, FL, 34...
Royal Harbor 5732 FREEPORT DR, TAVARES, FL, 32778, Tavares, FL 32778
$339,000

3 beds

|

2 baths

|

1,756 sq ft

|

House

5732 FREEPORT DR, TAVARES, FL, 32778
Community: Royal Harbor
Lakeside Landings 5427 COMPASS PT 1, OXFORD, FL, 34484, Oxford, FL 34484
$197,500

2 beds

|

2 baths

|

1,281 sq ft

|

Condo

5427 COMPASS PT 1, OXFORD, FL, 34484
Community: Lakeside Landings
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® 648 SAN MARINO DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$355,000

3 beds

|

2 baths

|

1,774 sq ft

|

House

648 SAN MARINO DR, THE VILLAGES, FL, 321...
Community: The Villages®
Cindy Certified
811 SUNSHOWER DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$294,000

4 beds

|

2 baths

|

1,840 sq ft

|

House

811 SUNSHOWER DR, LADY LAKE, FL, 32159
The Villages® 1194 MCDONOUGH PL, THE VILLAGES, FL, 321..., The Villages, FL 32163
$499,000

4 beds

|

2 baths

|

2,028 sq ft

|

House

1194 MCDONOUGH PL, THE VILLAGES, FL, 321...
Community: The Villages®
The Villages® 17723 SE 81ST TIMBERWOOD TER, THE VILLAG..., The Villages, FL 32162
$355,000

3 beds

|

2 baths

|

2,027 sq ft

|

House

17723 SE 81ST TIMBERWOOD TER, THE VILLAG...
Community: The Villages®
Royal Highlands 21849 TARTAN ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$424,900

3 beds

|

2 baths

|

2,074 sq ft

|

House

21849 TARTAN ST, LEESBURG, FL, 34748
Community: Royal Highlands
Cindy Certified
304 FREE RANGE DR, GROVELAND, FL, 34736, Groveland, FL 34736
$515,990

4 beds

|

3 baths

|

2,472 sq ft

|

House

304 FREE RANGE DR, GROVELAND, FL, 34736
Cindy Certified
324 FREE RANGE DR, GROVELAND, FL, 34736, Groveland, FL 34736
$499,990

4 beds

|

4 baths

|

2,442 sq ft

|

House

324 FREE RANGE DR, GROVELAND, FL, 34736
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
The Villages® 9711 SE 171ST ARGYLL ST, THE VILLAGES, F..., The Villages, FL 32162
$325,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

9711 SE 171ST ARGYLL ST, THE VILLAGES, F...
Community: The Villages®
Plantation at Leesburg 4721 TARA VIEW RD, LEESBURG, FL, 34748, Leesburg, FL 34748
$302,900

3 beds

|

2 baths

|

1,979 sq ft

|

House

4721 TARA VIEW RD, LEESBURG, FL, 34748
Legacy of Leesburg 5922 SAGE LEAF PL, LEESBURG, FL, 34748, Leesburg, FL 34748
$324,000

3 beds

|

2 baths

|

1,913 sq ft

|

House

5922 SAGE LEAF PL, LEESBURG, FL, 34748
Community: Legacy of Leesburg
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.
Harbor Hills Country Club 5321 GREENS DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$499,000

3 beds

|

2 baths

|

2,948 sq ft

|

House

5321 GREENS DR, LADY LAKE, FL, 32159
Spruce Creek South 17952 SE 107TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$209,900

3 beds

|

2 baths

|

1,450 sq ft

|

House

17952 SE 107TH CT, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
The Villages® 3698 ROBERTSON WAY, THE VILLAGES, FL, 32..., The Villages, FL 32163
$548,900

3 beds

|

2 baths

|

1,695 sq ft

|

Villa

3698 ROBERTSON WAY, THE VILLAGES, FL, 32...
Community: The Villages®
Esplanade at Highland Ranch 2639 STARGRASS CIR, CLERMONT, FL, 34715, Clermont, FL 34715
$479,000

2 beds

|

2 baths

|

1,732 sq ft

|

House

2639 STARGRASS CIR, CLERMONT, FL, 34715
Stonecrest 11255 SE 175TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$229,900

2 beds

|

2 baths

|

1,408 sq ft

|

House

11255 SE 175TH LN, SUMMERFIELD, FL, 3449...
Community: Stonecrest
The Villages® 758 MOORE TER, THE VILLAGES, FL, 32162, The Villages, FL 32162
$800,000

3 beds

|

2 baths

|

2,642 sq ft

|

House

758 MOORE TER, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 13811 COUNTY RD, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$300,000

4 beds

|

2 baths

|

2,280 sq ft

|

Manufactured Home

13811 COUNTY RD, LADY LAKE, FL, 32159
Community: The Villages®
Del Webb Minneola 2750 PURPLE MEADOW CT, MINNEOLA, FL, 347..., Minneola, FL 34715
$499,000

2 beds

|

2 baths

|

1,409 sq ft

|

House

2750 PURPLE MEADOW CT, MINNEOLA, FL, 347...
Community: Del Webb Minneola
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
Plantation at Leesburg 24239 BELLE MEDE DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$375,000

3 beds

|

2 baths

|

2,289 sq ft

|

House

24239 BELLE MEDE DR, LEESBURG, FL, 34748
The Villages® 8371 SE 168TH TRINITY PL, THE VILLAGES, ..., The Villages, FL 32162
$304,900

3 beds

|

2 baths

|

1,496 sq ft

|

House

8371 SE 168TH TRINITY 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.

Frequently Asked Questions


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1,145 homes
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