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Leesburg, FL 55+ active adult communities & homes for sale - Page 25

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
Trilogy® Orlando 119 FALLING ACORN AVE, GROVELAND, FL, 34..., Groveland, FL 34736
$338,000

2 beds

|

2 baths

|

1,651 sq ft

|

House

119 FALLING ACORN AVE, GROVELAND, FL, 34...
Community: Trilogy® Orlando
The Villages® 732 ROYAL PALM AVE, THE VILLAGES, FL, 32..., The Villages, FL 32159
$219,900

3 beds

|

2 baths

|

1,100 sq ft

|

Manufactured Home

732 ROYAL PALM AVE, THE VILLAGES, FL, 32...
Community: The Villages®
Arlington Ridge 4258 JAMES RIVER CIR, LEESBURG, FL, 3474..., Leesburg, FL 34748
$464,900

4 beds

|

3 baths

|

2,524 sq ft

|

House

4258 JAMES RIVER CIR, LEESBURG, FL, 3474...
Community: Arlington Ridge
Stonecrest 17440 SE 112TH AVE, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$320,000

3 beds

|

2 baths

|

1,794 sq ft

|

House

17440 SE 112TH AVE, SUMMERFIELD, FL, 344...
Community: Stonecrest
Pennbrooke Fairways 32676 OAK PARK DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$275,000

3 beds

|

2 baths

|

1,709 sq ft

|

House

32676 OAK PARK DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
Cindy Certified
707 SUNSHOWER DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$350,734

4 beds

|

3 baths

|

1,988 sq ft

|

House

707 SUNSHOWER DR, LADY LAKE, FL, 32159
The Villages® 2837 GRANT WAY, THE VILLAGES, FL, 32162, The Villages, FL 32162
$555,777

3 beds

|

2 baths

|

1,923 sq ft

|

House

2837 GRANT WAY, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 6231 ATKINSON LN, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$299,900

3 beds

|

2 baths

|

1,426 sq ft

|

House

6231 ATKINSON LN, THE VILLAGES, FL, 3216...
Community: The Villages®
Plantation at Leesburg 4908 CYPRESS HEAD CT, LEESBURG, FL, 3474..., Leesburg, FL 34748
$334,900

3 beds

|

2 baths

|

2,087 sq ft

|

House

4908 CYPRESS HEAD CT, LEESBURG, FL, 3474...
The Villages® 1603 COG HILL DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$248,000

2 beds

|

2 baths

|

1,542 sq ft

|

Manufactured Home

1603 COG HILL DR, LADY LAKE, 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.
Harbor Hills Country Club 5013 HARBOR HEIGHTS, LADY LAKE, FL, 3215..., Lady Lake, FL 32159
$320,000

3 beds

|

2 baths

|

1,954 sq ft

|

House

5013 HARBOR HEIGHTS, LADY LAKE, FL, 3215...
The Villages® 2427 SOUTHERN OAK ST, THE VILLAGES, FL, ..., The Villages, FL 32162
$294,499

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

2427 SOUTHERN OAK ST, THE VILLAGES, FL, ...
Community: The Villages®
Plantation at Leesburg 25073 RIVERWALK DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$285,000

3 beds

|

2 baths

|

1,814 sq ft

|

House

25073 RIVERWALK DR, LEESBURG, FL, 34748
The Villages® 930 TARRSON BLVD, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$109,907

2 beds

|

2 baths

|

960 sq ft

|

Manufactured Home

930 TARRSON BLVD, LADY LAKE, FL, 32159
Community: The Villages®
Heritage - The Cottages of Sanders Grove 6358 SANDERS GROVE CIR, OKAHUMPKA, FL, 3..., Okahumpka, FL 34762
$270,000

3 beds

|

2 baths

|

1,690 sq ft

|

House

6358 SANDERS GROVE CIR, OKAHUMPKA, FL, 3...
Harbor Hills Country Club 39654 GROVE HEIGHTS, LADY LAKE, FL, 3215..., Lady Lake, FL 32159
$699,900

4 beds

|

4 baths

|

2,761 sq ft

|

House

39654 GROVE HEIGHTS, LADY LAKE, FL, 3215...
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
Summit Chase Villas 12532 ORANGEWOOD CT, TAVARES, FL, 32778, Tavares, FL 32778
$199,800

2 beds

|

2 baths

|

918 sq ft

|

Condo

12532 ORANGEWOOD CT, TAVARES, FL, 32778
Community: Summit Chase Villas
The Villages® 17637 SE 80TH ALTAMAHA CT, THE VILLAGES,..., The Villages, FL 32162
$299,995

3 beds

|

2 baths

|

1,392 sq ft

|

House

17637 SE 80TH ALTAMAHA CT, THE VILLAGES,...
Community: The Villages®
Legacy of Leesburg 27545 DISCOVER CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$269,900

2 beds

|

2 baths

|

1,600 sq ft

|

House

27545 DISCOVER CT, LEESBURG, FL, 34748
Community: Legacy of Leesburg
Arlington Ridge 4334 BENT CREEK LN, LEESBURG, FL, 34748, Leesburg, FL 34748
$565,000

3 beds

|

3 baths

|

2,565 sq ft

|

House

4334 BENT CREEK LN, LEESBURG, FL, 34748
Community: Arlington 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.
The Villages® 1514 HILLCREST DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$205,000

2 beds

|

2 baths

|

1,513 sq ft

|

Manufactured Home

1514 HILLCREST DR, LADY LAKE, FL, 32159
Community: The Villages®
The Villages® 1166 BLOUNT AVE, THE VILLAGES, FL, 32163, The Villages, FL 32163
$729,000

3 beds

|

2 baths

|

2,103 sq ft

|

House

1166 BLOUNT AVE, THE VILLAGES, FL, 32163
Community: The Villages®
Legacy of Leesburg 27210 STONEY BROOK DR, LEESBURG, FL, 347..., Leesburg, FL 34748
$299,000

3 beds

|

2 baths

|

1,601 sq ft

|

House

27210 STONEY BROOK DR, LEESBURG, FL, 347...
Community: Legacy of Leesburg
Arlington Ridge 26921 WHITE PLAINS WAY, LEESBURG, FL, 34..., Leesburg, FL 34748
$199,000

2 beds

|

2 baths

|

1,254 sq ft

|

Villa

26921 WHITE PLAINS WAY, LEESBURG, FL, 34...
Community: Arlington Ridge
Royal Highlands 5607 SIR CHURCHILL DR, LEESBURG, FL, 347..., Leesburg, FL 34748
$389,999

3 beds

|

2 baths

|

2,312 sq ft

|

House

5607 SIR CHURCHILL DR, LEESBURG, FL, 347...
Community: Royal Highlands
Harbor Hills Country Club 6120 LANDINGS BLVD, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$699,000

3 beds

|

2 baths

|

2,598 sq ft

|

House

6120 LANDINGS BLVD, LADY LAKE, FL, 32159
The Villages® 17009 SE 96TH CHAPELWOOD CIR, THE VILLAG..., The Villages, FL 32162
$339,900

3 beds

|

2 baths

|

1,392 sq ft

|

House

17009 SE 96TH CHAPELWOOD CIR, THE VILLAG...
Community: The Villages®
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
The Villages® 324 EMMALEE PL, THE VILLAGES, FL, 32162, The Villages, FL 32162
$275,000

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

324 EMMALEE PL, THE VILLAGES, FL, 32162
Community: The Villages®
Arlington Ridge 4307 BENT CREEK LN, LEESBURG, FL, 34748, Leesburg, FL 34748
$369,900

3 beds

|

2 baths

|

1,683 sq ft

|

House

4307 BENT CREEK LN, LEESBURG, FL, 34748
Community: Arlington Ridge
Kings Ridge 3871 EVERSHOLT ST, CLERMONT, FL, 34711, Clermont, FL 34711
$289,900

2 beds

|

2 baths

|

1,327 sq ft

|

House

3871 EVERSHOLT 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.
The Villages® 2033 SALMON WAY, THE VILLAGES, FL, 32162, The Villages, FL 32162
$449,900

3 beds

|

2 baths

|

1,939 sq ft

|

House

2033 SALMON WAY, THE VILLAGES, FL, 32162
Community: The Villages®
Stonecrest 17083 SE 115TH TERRACE RD, SUMMERFIELD, ..., Summerfield, FL 34491
$289,900

3 beds

|

2 baths

|

1,724 sq ft

|

House

17083 SE 115TH TERRACE RD, SUMMERFIELD, ...
Community: Stonecrest
Plantation at Leesburg 3719 BELLE ROSE DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$445,000

3 beds

|

3 baths

|

2,571 sq ft

|

House

3719 BELLE ROSE DR, LEESBURG, FL, 34748
Plantation at Leesburg 4967 HERON RUN CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$229,800

2 beds

|

2 baths

|

1,119 sq ft

|

House

4967 HERON RUN CIR, LEESBURG, FL, 34748
The Villages® 1314 SANTA ROSA CT, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$400,000

2 beds

|

2 baths

|

1,302 sq ft

|

Villa

1314 SANTA ROSA CT, LADY LAKE, FL, 32159
Community: The Villages®
The Villages® 4151 BALCHARAN TER, THE VILLAGES, FL, 32..., The Villages, FL 32163
$361,000

3 beds

|

2 baths

|

1,539 sq ft

|

House

4151 BALCHARAN TER, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 23104 SANDALWOOD DR 104, WILDWOOD, FL, 3..., Wildwood, FL 34785
$125,000

2 beds

|

2 baths

|

1,110 sq ft

|

Condo

23104 SANDALWOOD DR 104, WILDWOOD, FL, 3...
Community: The Villages®
Cindy Certified
5208 MEADOW SONG DR, OKAHUMPKA, FL, 3476..., Okahumpka, FL 34762
$364,900

4 beds

|

3 baths

|

2,291 sq ft

|

House

5208 MEADOW SONG DR, OKAHUMPKA, FL, 3476...
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
The Villages® 16596 SE 77TH NORTHRIDGE CT, THE VILLAGE..., The Villages, FL 32162
$332,000

3 beds

|

2 baths

|

1,483 sq ft

|

House

16596 SE 77TH NORTHRIDGE CT, THE VILLAGE...
Community: The Villages®
Summit Chase Villas 12418 ORANGEWOOD CIR, TAVARES, FL, 32778, Tavares, FL 32778
$160,000

2 beds

|

2 baths

|

918 sq ft

|

Villa

12418 ORANGEWOOD CIR, TAVARES, FL, 32778
Community: Summit Chase Villas
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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