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Leesburg, FL 55+ active adult communities & homes for sale - Page 4

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
Plantation at Leesburg 25419 CRESTWATER DRIVE DR, LEESBURG, FL,..., Leesburg, FL 34748
$245,000

2 beds

|

2 baths

|

1,581 sq ft

|

House

25419 CRESTWATER DRIVE DR, LEESBURG, FL,...
Lakeside Landings 10150 MAINSAIL DR, OXFORD, FL, 34484, Oxford, FL 34484
$267,500

3 beds

|

2 baths

|

1,592 sq ft

|

House

10150 MAINSAIL DR, OXFORD, FL, 34484
Community: Lakeside Landings
The Villages® 2265 HACKNEY WAY, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$399,900

3 beds

|

2 baths

|

1,715 sq ft

|

House

2265 HACKNEY WAY, THE VILLAGES, FL, 3216...
Community: The Villages®
Trilogy® Orlando 771 ALCOVE DR, GROVELAND, FL, 34736, Groveland, FL 34736
$539,990

2 beds

|

3 baths

|

2,087 sq ft

|

House

771 ALCOVE DR, GROVELAND, FL, 34736
Community: Trilogy® Orlando
The Villages® 3001 GLENWOOD PL, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$347,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

3001 GLENWOOD PL, 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
Lakeside Landings 10331 ADDISON SHORE WAY, OXFORD, FL, 344..., Oxford, FL 34484
$423,500

3 beds

|

2 baths

|

2,003 sq ft

|

House

10331 ADDISON SHORE WAY, OXFORD, FL, 344...
Community: Lakeside Landings
Scottish Highlands 1409 NEW ABBEY AVE, LEESBURG, FL, 34788, Leesburg, FL 34788
$219,900

2 beds

|

2 baths

|

1,674 sq ft

|

House

1409 NEW ABBEY AVE, LEESBURG, FL, 34788
Community: Scottish Highlands
The Villages® 720 SAN MARINO DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$318,000

2 beds

|

2 baths

|

1,613 sq ft

|

House

720 SAN MARINO DR, THE VILLAGES, FL, 321...
Community: The Villages®
Harbor Hills Country Club 39622 HARBOR HILLS BLVD, LADY LAKE, FL, ..., Lady Lake, FL 32159
$410,000

3 beds

|

2 baths

|

2,175 sq ft

|

House

39622 HARBOR HILLS BLVD, LADY LAKE, FL, ...
Plantation at Leesburg 5336 TIDEWATER ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$325,000

2 beds

|

2 baths

|

1,918 sq ft

|

House

5336 TIDEWATER ST, 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.
Cindy Certified
5204 MEADOW SONG DR, OKAHUMPKA, FL, 3476..., Okahumpka, FL 34762
$390,000

4 beds

|

3 baths

|

2,291 sq ft

|

House

5204 MEADOW SONG DR, OKAHUMPKA, FL, 3476...
Royal Highlands 21212 ROYAL ST GEORGES LN, LEESBURG, FL,..., Leesburg, FL 34748
$249,000

2 beds

|

2 baths

|

1,299 sq ft

|

House

21212 ROYAL ST GEORGES LN, LEESBURG, FL,...
Community: Royal Highlands
The Villages® 806 SAN SALVADOR DR, THE VILLAGES, FL, 3..., The Villages, FL 32159
$379,900

3 beds

|

2 baths

|

1,527 sq ft

|

House

806 SAN SALVADOR DR, THE VILLAGES, FL, 3...
Community: The Villages®
Esplanade at Highland Ranch 1334 ZEEK RIDGE ST, CLERMONT, FL, 34715, Clermont, FL 34715
$554,900

3 beds

|

3 baths

|

2,084 sq ft

|

House

1334 ZEEK RIDGE ST, CLERMONT, FL, 34715
The Villages® 1402 CAMERO DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$429,900

3 beds

|

2 baths

|

1,904 sq ft

|

House

1402 CAMERO DR, THE VILLAGES, FL, 32159
Community: The Villages®
Scottish Highlands 37 GORDON CT, LEESBURG, FL, 34788, Leesburg, FL 34788
$189,900

2 beds

|

2 baths

|

1,101 sq ft

|

House

37 GORDON CT, LEESBURG, FL, 34788
Community: Scottish Highlands
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
The Villages® 2022 CASTANO PL, THE VILLAGES, FL, 32159, The Villages, FL 32159
$327,500

3 beds

|

2 baths

|

1,527 sq ft

|

House

2022 CASTANO PL, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 9367 SE 176TH SAFFOLD ST, THE VILLAGES, ..., The Villages, FL 32162
$332,000

3 beds

|

2 baths

|

1,555 sq ft

|

House

9367 SE 176TH SAFFOLD ST, THE VILLAGES, ...
Community: The Villages®
Pennbrooke Fairways 622 COTTAGE PARK LN, LEESBURG, FL, 34748, Leesburg, FL 34748
$139,500

1 beds

|

1 baths

|

560 sq ft

|

Manufactured Home

622 COTTAGE PARK LN, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Royal Highlands 21516 CASTLE VIEW CT, LEESBURG, FL, 3474..., Leesburg, FL 34748
$380,000

3 beds

|

2 baths

|

1,798 sq ft

|

House

21516 CASTLE VIEW CT, LEESBURG, FL, 3474...
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.
Harbor Hills Country Club 6053 SPINNAKER LOOP, LADY LAKE, FL, 3215..., Lady Lake, FL 32159
$617,500

3 beds

|

3 baths

|

3,024 sq ft

|

House

6053 SPINNAKER LOOP, LADY LAKE, FL, 3215...
Trilogy® Orlando 902 TIDAL POND DR, GROVELAND, FL, 34736, Groveland, FL 34736
$365,000

2 beds

|

2 baths

|

1,704 sq ft

|

House

902 TIDAL POND DR, GROVELAND, FL, 34736
Community: Trilogy® Orlando
The Villages® 2741 DUNHAM DR, THE VILLAGES, FL, 32163, The Villages, FL 32163
$1,190,000

3 beds

|

3 baths

|

2,673 sq ft

|

House

2741 DUNHAM DR, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 2615 PRIVADA DR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$255,000

3 beds

|

2 baths

|

1,210 sq ft

|

House

2615 PRIVADA DR, THE VILLAGES, FL, 32162
Community: The Villages®
Heritage Hills 3493 EMBERS LN, CLERMONT, FL, 34711, Clermont, FL 34711
$395,000

3 beds

|

2 baths

|

1,672 sq ft

|

House

3493 EMBERS LN, CLERMONT, FL, 34711
Community: Heritage Hills
Cindy Certified
4540 GLIDING WAVE ST, WINTER GARDEN, FL,..., Winter Garden, FL 34787
$560,000

3 beds

|

2 baths

|

2,144 sq ft

|

House

4540 GLIDING WAVE ST, WINTER GARDEN, FL,...
Trilogy® Orlando 342 ALCOVE DR, GROVELAND, FL, 34736, Groveland, FL 34736
$350,000

2 beds

|

2 baths

|

1,568 sq ft

|

House

342 ALCOVE DR, GROVELAND, FL, 34736
Community: Trilogy® Orlando
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
The Villages® 3254 DELK DR, THE VILLAGES, FL, 32163, The Villages, FL 32163
$559,900

3 beds

|

2 baths

|

1,930 sq ft

|

House

3254 DELK DR, THE VILLAGES, FL, 32163
Community: The Villages®
Cindy Certified
593 KISTLER CIR, CLERMONT, FL, 34715, Clermont, FL 34715
$499,900

4 beds

|

2 baths

|

2,065 sq ft

|

House

593 KISTLER CIR, CLERMONT, FL, 34715
The Villages® 974 JAY ST, THE VILLAGES, FL, 32163, The Villages, FL 32163
$439,000

3 beds

|

2 baths

|

1,647 sq ft

|

House

974 JAY ST, THE VILLAGES, FL, 32163
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.
Pennbrooke Fairways 911 GRAND VISTA TRL, LEESBURG, FL, 34748, Leesburg, FL 34748
$249,900

2 beds

|

2 baths

|

1,571 sq ft

|

House

911 GRAND VISTA TRL, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
The Villages® 683 KRIETEMEYER PATH, THE VILLAGES, FL, ..., The Villages, FL 32163
$1,900,000

4 beds

|

3 baths

|

3,345 sq ft

|

House

683 KRIETEMEYER PATH, THE VILLAGES, FL, ...
Community: The Villages®
Plantation at Leesburg 5418 BARNWELL CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$349,000

2 beds

|

3 baths

|

2,188 sq ft

|

House

5418 BARNWELL CT, LEESBURG, FL, 34748
The Villages® 2701 DAFFODIL CT, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$534,900

3 beds

|

3 baths

|

2,075 sq ft

|

House

2701 DAFFODIL CT, THE VILLAGES, FL, 3216...
Community: The Villages®
Spruce Creek South 17841 SE 106TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$209,000

2 beds

|

2 baths

|

1,446 sq ft

|

House

17841 SE 106TH CT, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
The Villages® 313 VARNVILLE WAY, THE VILLAGES, FL, 321..., The Villages, FL 32162
$324,000

2 beds

|

2 baths

|

1,266 sq ft

|

Villa

313 VARNVILLE WAY, THE VILLAGES, FL, 321...
Community: The Villages®
Plantation at Leesburg 4431 NOTTOWAY DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$260,000

3 beds

|

2 baths

|

1,751 sq ft

|

House

4431 NOTTOWAY DR, LEESBURG, FL, 34748
The Villages® 17382 SE 93RD RETFORD TER, THE VILLAGES,..., The Villages, FL 32162
$229,900

2 beds

|

2 baths

|

1,160 sq ft

|

House

17382 SE 93RD RETFORD TER, THE VILLAGES,...
Community: The Villages®
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
The Villages® 1319 CARVELLO DR, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$309,000

2 beds

|

2 baths

|

1,148 sq ft

|

House

1319 CARVELLO DR, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 2105 SUAREZ CT, THE VILLAGES, FL, 32159, The Villages, FL 32159
$365,900

3 beds

|

2 baths

|

1,452 sq ft

|

House

2105 SUAREZ CT, THE VILLAGES, 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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