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Leesburg, FL 55+ active adult communities & homes for sale - Page 21

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
Harbor Hills Country Club 4008 PINNACLE PLACE CT, LADY LAKE, FL, 3..., Lady Lake, FL 32159
$685,000

3 beds

|

3 baths

|

2,434 sq ft

|

House

4008 PINNACLE PLACE CT, LADY LAKE, FL, 3...
The Villages® 1506 DELLANO WAY, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$412,000

2 beds

|

2 baths

|

1,782 sq ft

|

House

1506 DELLANO WAY, THE VILLAGES, FL, 3215...
Community: The Villages®
Del Webb Minneola 2458 DEL WEBB DR, MINNEOLA, FL, 34715, Minneola, FL 34715
$725,000

3 beds

|

3 baths

|

2,260 sq ft

|

House

2458 DEL WEBB DR, MINNEOLA, FL, 34715
Community: Del Webb Minneola
Pennbrooke Fairways 32222 SUMMERTREE CIR, LEESBURG, FL, 3474..., Leesburg, FL 34748
$289,000

2 beds

|

2 baths

|

1,725 sq ft

|

House

32222 SUMMERTREE CIR, LEESBURG, FL, 3474...
Community: Pennbrooke Fairways
Cindy Certified
4550 LIVE OAK LN, OXFORD, FL, 34484, Oxford, FL 34484
$428,990

5 beds

|

3 baths

|

2,587 sq ft

|

House

4550 LIVE OAK LN, OXFORD, FL, 34484
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
Legacy of Leesburg 27134 NOSTALGIA DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$299,900

3 beds

|

2 baths

|

1,601 sq ft

|

House

27134 NOSTALGIA DR, LEESBURG, FL, 34748
Community: Legacy of Leesburg
Cindy Certified
10608 OAK TREE ALY, OXFORD, FL, 34484, Oxford, FL 34484
$307,990

3 beds

|

2 baths

|

1,654 sq ft

|

House

10608 OAK TREE ALY, OXFORD, FL, 34484
Harbor Hills Country Club 5506 CITATION CT, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$619,000

3 beds

|

3 baths

|

2,698 sq ft

|

House

5506 CITATION CT, LADY LAKE, FL, 32159
Stonecrest 17719 SE 114TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$260,000

2 beds

|

2 baths

|

1,704 sq ft

|

Villa

17719 SE 114TH CT, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Cindy Certified
4558 LIVE OAK LN, OXFORD, FL, 34484, Oxford, FL 34484
$330,990

4 beds

|

3 baths

|

1,933 sq ft

|

House

4558 LIVE OAK LN, OXFORD, FL, 34484
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 - The Cottages of Sanders Grove 6213 SANDERS GROVE CIR, LEESBURG, FL, 34..., Leesburg, FL 34748
$327,595

4 beds

|

2 baths

|

1,625 sq ft

|

House

6213 SANDERS GROVE CIR, LEESBURG, FL, 34...
Heritage - The Cottages of Sanders Grove 6217 SANDERS GROVE CIR, LEESBURG, FL, 34..., Leesburg, FL 34748
$358,389

4 beds

|

3 baths

|

1,938 sq ft

|

House

6217 SANDERS GROVE CIR, LEESBURG, FL, 34...
Heritage - The Cottages of Sanders Grove 5715 HIAWASSEE RD, LEESBURG, FL, 34748, Leesburg, FL 34748
$344,250

4 beds

|

3 baths

|

1,938 sq ft

|

House

5715 HIAWASSEE RD, LEESBURG, FL, 34748
Heritage - The Cottages of Sanders Grove 6205 SANDERS GROVE CIR, OKAHUMPKA, FL, 3..., Okahumpka, FL 34762
$320,091

3 beds

|

2 baths

|

1,407 sq ft

|

House

6205 SANDERS GROVE CIR, OKAHUMPKA, FL, 3...
The Villages® 1516 MARTINEZ DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$479,000

2 beds

|

2 baths

|

1,546 sq ft

|

Villa

1516 MARTINEZ DR, LADY LAKE, FL, 32159
Community: The Villages®
Heritage - The Cottages of Sanders Grove 5719 HIAWASSEE RD, OKAHUMPKA, FL, 34762, Okahumpka, FL 34762
$335,990

4 beds

|

2 baths

|

1,625 sq ft

|

House

5719 HIAWASSEE RD, OKAHUMPKA, FL, 34762
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
Kings Ridge 3916 SCARBOROUGH CT, CLERMONT, FL, 34711, Clermont, FL 34711
$469,000

3 beds

|

2 baths

|

2,147 sq ft

|

House

3916 SCARBOROUGH CT, CLERMONT, FL, 34711
Community: Kings Ridge
Kings Ridge 2265 CALVERT CT, CLERMONT, FL, 34711, Clermont, FL 34711
$429,900

3 beds

|

2 baths

|

2,031 sq ft

|

House

2265 CALVERT CT, CLERMONT, FL, 34711
Community: Kings Ridge
Summit Greens 3003 PINNACLE CT, CLERMONT, FL, 34711, Clermont, FL 34711
$349,000

2 beds

|

2 baths

|

1,718 sq ft

|

House

3003 PINNACLE CT, CLERMONT, FL, 34711
Community: Summit Greens
Heritage - The Cottages of Sanders Grove 5727 HIAWASSEE RD, LEESBURG, FL, 34748, Leesburg, FL 34748
$299,990

3 beds

|

2 baths

|

1,407 sq ft

|

House

5727 HIAWASSEE RD, 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.
The Villages® 16581 SE 77TH NORTHRIDGE CT, THE VILLAGE..., The Villages, FL 32162
$469,000

3 beds

|

2 baths

|

1,850 sq ft

|

House

16581 SE 77TH NORTHRIDGE CT, THE VILLAGE...
Community: The Villages®
Heritage - The Cottages of Sanders Grove 6209 SANDERS GROVE CIR, LEESBURG, FL, 34..., Leesburg, FL 34748
$338,445

4 beds

|

2 baths

|

1,758 sq ft

|

House

6209 SANDERS GROVE CIR, LEESBURG, FL, 34...
Heritage - The Cottages of Sanders Grove 6201 N SANDERS GROVE CIR, LEESBURG, FL, ..., Leesburg, FL 34748
$336,535

4 beds

|

2 baths

|

1,625 sq ft

|

House

6201 N SANDERS GROVE CIR, LEESBURG, FL, ...
Plantation at Leesburg 25245 QUAIL CROFT PL, LEESBURG, FL, 3474..., Leesburg, FL 34748
$230,000

2 beds

|

2 baths

|

1,653 sq ft

|

House

25245 QUAIL CROFT PL, LEESBURG, FL, 3474...
Scottish Highlands 1622 NEW ABBEY AVE, LEESBURG, FL, 34788, Leesburg, FL 34788
$279,000

2 beds

|

2 baths

|

1,532 sq ft

|

House

1622 NEW ABBEY AVE, LEESBURG, FL, 34788
Community: Scottish Highlands
The Villages® 17421 SE 78TH HARMONY CIR, THE VILLAGES,..., The Villages, FL 32162
$248,000

2 beds

|

2 baths

|

1,160 sq ft

|

House

17421 SE 78TH HARMONY CIR, THE VILLAGES,...
Community: The Villages®
Royal Highlands 21932 ROYAL ST GEORGES LN, LEESBURG, FL,..., Leesburg, FL 34748
$368,000

3 beds

|

2 baths

|

1,684 sq ft

|

House

21932 ROYAL ST GEORGES LN, LEESBURG, FL,...
Community: Royal Highlands
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
Cindy Certified
864 VINEYARD RIDGE RD, MINNEOLA, FL, 347..., Minneola, FL 34715
$560,000

4 beds

|

2 baths

|

2,236 sq ft

|

House

864 VINEYARD RIDGE RD, MINNEOLA, FL, 347...
The Villages® 3419 CARRABELLE CT, THE VILLAGES, FL, 32..., The Villages, FL 32163
$265,000

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

3419 CARRABELLE CT, THE VILLAGES, FL, 32...
Community: The Villages®
Stonecrest 17424 SE 111TH AVE, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$260,900

3 beds

|

2 baths

|

1,446 sq ft

|

House

17424 SE 111TH AVE, SUMMERFIELD, FL, 344...
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.
The Villages® 1625 HILTON HEAD BLVD, LADY LAKE, FL, 32..., Lady Lake, FL 32159
$149,900

2 beds

|

2 baths

|

1,332 sq ft

|

Manufactured Home

1625 HILTON HEAD BLVD, LADY LAKE, FL, 32...
Community: The Villages®
Royal Highlands 21830 KING EDWARD CT, LEESBURG, FL, 3474..., Leesburg, FL 34748
$339,900

3 beds

|

2 baths

|

2,268 sq ft

|

House

21830 KING EDWARD CT, LEESBURG, FL, 3474...
Community: Royal Highlands
Cindy Certified
795 SUNSHOWER DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$324,000

4 beds

|

3 baths

|

1,988 sq ft

|

House

795 SUNSHOWER DR, LADY LAKE, FL, 32159
Stonecrest 16887 SE 110TH COURT RD, SUMMERFIELD, FL..., Summerfield, FL 34491
$419,000

3 beds

|

2 baths

|

2,100 sq ft

|

House

16887 SE 110TH COURT RD, SUMMERFIELD, FL...
Community: Stonecrest
The Villages® 2446 HOPESPRING LOOP, THE VILLAGES, FL, ..., The Villages, FL 32162
$379,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

2446 HOPESPRING LOOP, THE VILLAGES, FL, ...
Community: The Villages®
The Villages® 321 SAN MARINO DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$350,000

2 beds

|

2 baths

|

1,478 sq ft

|

House

321 SAN MARINO DR, THE VILLAGES, FL, 321...
Community: The Villages®
Legacy of Leesburg 5304 TREASURE VIEW WAY, LEESBURG, FL, 34..., Leesburg, FL 34748
$315,000

3 beds

|

2 baths

|

1,641 sq ft

|

House

5304 TREASURE VIEW WAY, LEESBURG, FL, 34...
Community: Legacy of Leesburg
Kings Ridge 3786 AVON CT, CLERMONT, FL, 34711, Clermont, FL 34711
$339,000

3 beds

|

2 baths

|

1,639 sq ft

|

House

3786 AVON CT, CLERMONT, FL, 34711
Community: Kings Ridge
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
The Villages® 1133 DEL TORO DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$299,000

2 beds

|

2 baths

|

1,332 sq ft

|

House

1133 DEL TORO DR, LADY LAKE, FL, 32159
Community: The Villages®
Cindy Certified
779 SUNSHOWER DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$323,604

4 beds

|

3 baths

|

1,988 sq ft

|

House

779 SUNSHOWER DR, LADY LAKE, FL, 32159
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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