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Leesburg, FL 55+ active adult communities & homes for sale - Page 26

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® 1609 BLOSSOM TER, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$325,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

1609 BLOSSOM TER, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 1521 HOLLYBERRY PL, THE VILLAGES, FL, 32..., The Villages, FL 32162
$349,900

3 beds

|

2 baths

|

1,527 sq ft

|

House

1521 HOLLYBERRY PL, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 8331 COUNTY RD 109, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$283,000

4 beds

|

2 baths

|

2,240 sq ft

|

Manufactured Home

8331 COUNTY RD 109, LADY LAKE, FL, 32159
Community: The Villages®
Spruce Creek South 17990 SE 100TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$299,900

3 beds

|

2 baths

|

1,870 sq ft

|

House

17990 SE 100TH TER, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
Cindy Certified
588 AUTUMN ASH DR, CLERMONT, FL, 34715, Clermont, FL 34715
$585,000

4 beds

|

3 baths

|

2,827 sq ft

|

House

588 AUTUMN ASH DR, CLERMONT, FL, 34715
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
Kings Ridge 2308 TWICKINGHAM CT, CLERMONT, FL, 34711, Clermont, FL 34711
$359,900

3 beds

|

2 baths

|

1,892 sq ft

|

House

2308 TWICKINGHAM CT, CLERMONT, FL, 34711
Community: Kings Ridge
The Villages® 603 ROBIN LN, WILDWOOD, FL, 34785, Wildwood, FL 34785
$159,900

2 beds

|

2 baths

|

1,352 sq ft

|

Manufactured Home

603 ROBIN LN, WILDWOOD, FL, 34785
Community: The Villages®
The Villages® 7809 SE 171ST HARLESTON ST, THE VILLAGES..., The Villages, FL 32162
$464,900

3 beds

|

2 baths

|

2,048 sq ft

|

Villa

7809 SE 171ST HARLESTON ST, THE VILLAGES...
Community: The Villages®
Plantation at Leesburg 4960 HERON RUN CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$234,900

2 beds

|

2 baths

|

1,289 sq ft

|

House

4960 HERON RUN CIR, LEESBURG, FL, 34748
Cindy Certified
1208 TURTLE ISLAND RD, LADY LAKE, FL, 32..., Lady Lake, FL 32159
$299,000

3 beds

|

2 baths

|

1,509 sq ft

|

Halfplex

1208 TURTLE ISLAND RD, LADY LAKE, FL, 32...
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® 1411 JUAREZ PL, THE VILLAGES, FL, 32159, The Villages, FL 32159
$459,000

3 beds

|

2 baths

|

1,388 sq ft

|

House

1411 JUAREZ PL, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 1147 ELIZABETH CT, THE VILLAGES, FL, 321..., The Villages, FL 32162
$499,900

3 beds

|

2 baths

|

1,602 sq ft

|

Villa

1147 ELIZABETH CT, THE VILLAGES, FL, 321...
Community: The Villages®
Cindy Certified
142 TRANQUIL MIRROR LAKE CT 18, CLERMONT..., Clermont, FL 34711
$1,492,545

4 beds

|

3 baths

|

2,974 sq ft

|

House

142 TRANQUIL MIRROR LAKE CT 18, CLERMONT...
Plantation at Leesburg 25312 GREEN HERON DR, LEESBURG, FL, 3474..., Leesburg, FL 34748
$220,000

2 beds

|

2 baths

|

1,289 sq ft

|

House

25312 GREEN HERON DR, LEESBURG, FL, 3474...
Heritage Hills 3752 QUAINT LN, CLERMONT, FL, 34711, Clermont, FL 34711
$399,900

3 beds

|

3 baths

|

2,006 sq ft

|

House

3752 QUAINT LN, CLERMONT, FL, 34711
Community: Heritage Hills
The Villages® 1232 ZAPATA PL, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$249,000

2 beds

|

2 baths

|

1,040 sq ft

|

House

1232 ZAPATA PL, LADY LAKE, FL, 32159
Community: The Villages®
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
Cindy Certified
951 VINEYARD RIDGE RD, MINNEOLA, FL, 347..., Minneola, FL 34715
$475,000

4 beds

|

3 baths

|

1,974 sq ft

|

House

951 VINEYARD RIDGE RD, MINNEOLA, FL, 347...
Highland Lakes 5618 ROSEWALL CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$205,000

2 beds

|

2 baths

|

1,306 sq ft

|

House

5618 ROSEWALL CIR, LEESBURG, FL, 34748
Community: Highland Lakes
Summit Chase Villas 12449 ORANGEWOOD CIR 17, TAVARES, FL, 32..., Tavares, FL 32778
$174,900

2 beds

|

2 baths

|

918 sq ft

|

Condo

12449 ORANGEWOOD CIR 17, TAVARES, FL, 32...
Community: Summit Chase Villas
Summit Greens 2197 CALEDONIAN ST, CLERMONT, FL, 34711, Clermont, FL 34711
$332,500

3 beds

|

2 baths

|

1,703 sq ft

|

House

2197 CALEDONIAN ST, CLERMONT, FL, 34711
Community: Summit Greens
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.
Arlington Ridge 27118 ROANOKE DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$364,900

3 beds

|

2 baths

|

1,713 sq ft

|

House

27118 ROANOKE DR, LEESBURG, FL, 34748
Community: Arlington Ridge
The Villages® 110 CHULA VISTA AVE, LADY LAKE, FL, 3215..., Lady Lake, FL 32159
$400,000

3 beds

|

2 baths

|

2,038 sq ft

|

House

110 CHULA VISTA AVE, LADY LAKE, FL, 3215...
Community: The Villages®
Highland Lakes 26627 RACQUET CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$219,000

2 beds

|

2 baths

|

1,120 sq ft

|

Villa

26627 RACQUET CIR, LEESBURG, FL, 34748
Community: Highland Lakes
Cindy Certified
5256 MEADOW SONG DR, OKAHUMPKA, FL, 3476..., Okahumpka, FL 34762
$375,000

4 beds

|

2 baths

|

1,928 sq ft

|

House

5256 MEADOW SONG DR, OKAHUMPKA, FL, 3476...
Trilogy® Orlando 184 CREPE MYRTLE DR, GROVELAND, FL, 3473..., Groveland, FL 34736
$519,000

4 beds

|

3 baths

|

3,044 sq ft

|

House

184 CREPE MYRTLE DR, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
Arlington Ridge 26645 MANASSAS DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$450,000

3 beds

|

2 baths

|

2,236 sq ft

|

House

26645 MANASSAS DR, LEESBURG, FL, 34748
Community: Arlington Ridge
The Villages® 17403 SE 77TH SYCAMORE AVE, THE VILLAGES..., The Villages, FL 32162
$270,000

2 beds

|

2 baths

|

1,160 sq ft

|

Villa

17403 SE 77TH SYCAMORE AVE, 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® 108 N TIMBER TRL, WILDWOOD, FL, 34785, Wildwood, FL 34785
$119,900

2 beds

|

2 baths

|

1,232 sq ft

|

Manufactured Home

108 N TIMBER TRL, WILDWOOD, FL, 34785
Community: The Villages®
The Villages® 415 S TIMBER TRL, WILDWOOD, FL, 34785, Wildwood, FL 34785
$79,900

2 beds

|

2 baths

|

1,144 sq ft

|

Manufactured Home

415 S TIMBER TRL, WILDWOOD, FL, 34785
Community: The Villages®
Stonecrest 11217 SE 170TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$285,000

3 beds

|

2 baths

|

1,472 sq ft

|

House

11217 SE 170TH LN, 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.
Stonecrest 11614 SE 172ND LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$349,000

3 beds

|

2 baths

|

1,919 sq ft

|

House

11614 SE 172ND LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
The Villages® 9230 SE 179TH WESLEY ST, THE VILLAGES, F..., The Villages, FL 32162
$254,900

2 beds

|

2 baths

|

1,148 sq ft

|

House

9230 SE 179TH WESLEY ST, THE VILLAGES, F...
Community: The Villages®
Stonecrest 17380 SE 111TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$259,000

2 beds

|

2 baths

|

1,359 sq ft

|

Villa

17380 SE 111TH CT, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Royal Highlands 21811 KING HENRY AVE, LEESBURG, FL, 3474..., Leesburg, FL 34748
$324,900

3 beds

|

2 baths

|

1,918 sq ft

|

House

21811 KING HENRY AVE, LEESBURG, FL, 3474...
Community: Royal Highlands
Trilogy® Orlando 329 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736
$385,900

2 beds

|

2 baths

|

1,808 sq ft

|

House

329 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
Royal Highlands 5729 KING JAMES AVE, LEESBURG, FL, 34748, Leesburg, FL 34748
$349,900

3 beds

|

3 baths

|

2,402 sq ft

|

House

5729 KING JAMES AVE, LEESBURG, FL, 34748
Community: Royal Highlands
The Villages® 5719 SPARTINA TER, THE VILLAGES, FL, 321..., The Villages, FL 32163
$279,000

2 beds

|

2 baths

|

1,258 sq ft

|

Villa

5719 SPARTINA TER, THE VILLAGES, FL, 321...
Community: The Villages®
Heritage Hills 4052 SERENA LN, CLERMONT, FL, 34711, Clermont, FL 34711
$385,000

3 beds

|

2 baths

|

1,672 sq ft

|

House

4052 SERENA LN, CLERMONT, FL, 34711
Community: Heritage Hills
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
Plantation at Leesburg 3544 MOUNT HOPE LOOP, LEESBURG, FL, 3474..., Leesburg, FL 34748
$310,000

3 beds

|

2 baths

|

1,856 sq ft

|

House

3544 MOUNT HOPE LOOP, LEESBURG, FL, 3474...
Cindy Certified
902 BUCKEYE DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$427,990

4 beds

|

3 baths

|

2,471 sq ft

|

House

902 BUCKEYE 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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