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Leesburg, FL 55+ active adult communities & homes for sale - Page 8

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 25845 GLEN EAGLE DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$325,000

3 beds

|

2 baths

|

2,047 sq ft

|

House

25845 GLEN EAGLE DR, LEESBURG, FL, 34748
Royal Highlands 5401 ESSEX CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$370,000

3 beds

|

3 baths

|

2,009 sq ft

|

House

5401 ESSEX CT, LEESBURG, FL, 34748
Community: Royal Highlands
Highland Lakes 27138 RACQUET CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$329,900

3 beds

|

2 baths

|

2,025 sq ft

|

House

27138 RACQUET CIR, LEESBURG, FL, 34748
Community: Highland Lakes
The Villages® 622 KELLER CT, THE VILLAGES, FL, 32163, The Villages, FL 32163
$529,900

3 beds

|

2 baths

|

1,907 sq ft

|

House

622 KELLER CT, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 1537 E SCHWARTZ BLVD, LADY LAKE, FL, 321..., Lady Lake, FL 32159
$179,900

2 beds

|

2 baths

|

1,342 sq ft

|

Manufactured Home

1537 E SCHWARTZ BLVD, LADY LAKE, FL, 321...
Community: The Villages®
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
Scottish Highlands 21 ABERDEEN CIR, LEESBURG, FL, 34788, Leesburg, FL 34788
$162,500

2 beds

|

2 baths

|

960 sq ft

|

House

21 ABERDEEN CIR, LEESBURG, FL, 34788
Community: Scottish Highlands
The Villages® 1744 GIST CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$1,499,950

3 beds

|

3 baths

|

3,444 sq ft

|

House

1744 GIST CT, THE VILLAGES, FL, 32162
Community: The Villages®
Lakeside Landings 4994 GOLDEN EAGLE DR, OXFORD, FL, 34484, Oxford, FL 34484
$289,000

3 beds

|

2 baths

|

1,315 sq ft

|

House

4994 GOLDEN EAGLE DR, OXFORD, FL, 34484
Community: Lakeside Landings
Pennbrooke Fairways 402 GRAND VISTA TRL, LEESBURG, FL, 34748, Leesburg, FL 34748
$389,000

3 beds

|

2 baths

|

2,500 sq ft

|

House

402 GRAND VISTA TRL, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Scottish Highlands 2311 BONNIE VIEW CT, LEESBURG, FL, 34788, Leesburg, FL 34788
$220,000

2 beds

|

2 baths

|

1,479 sq ft

|

House

2311 BONNIE VIEW CT, LEESBURG, FL, 34788
Community: Scottish 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.
The Villages® 1212 AVENIDA DE LAS CASAS, THE VILLAGES,..., The Villages, FL 32159
$509,000

2 beds

|

4 baths

|

2,582 sq ft

|

Condo

1212 AVENIDA DE LAS CASAS, THE VILLAGES,...
Community: The Villages®
Cindy Certified
151 BRIDGER TRAIL CT, MINNEOLA, FL, 3471..., Minneola, FL 34715
$450,000

5 beds

|

3 baths

|

2,080 sq ft

|

House

151 BRIDGER TRAIL CT, MINNEOLA, FL, 3471...
The Villages® 1364 FRANCESCA PL, THE VILLAGES, FL, 321..., The Villages, FL 32163
$569,000

3 beds

|

3 baths

|

1,921 sq ft

|

House

1364 FRANCESCA PL, THE VILLAGES, FL, 321...
Community: The Villages®
Stonecrest 11041 SE 174TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$465,000

4 beds

|

3 baths

|

2,628 sq ft

|

House

11041 SE 174TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
Royal Highlands 21506 QUEEN ANNE CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$349,900

3 beds

|

2 baths

|

2,041 sq ft

|

House

21506 QUEEN ANNE CT, LEESBURG, FL, 34748
Community: Royal Highlands
Spruce Creek South 10622 SE 179TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$242,000

3 beds

|

2 baths

|

1,450 sq ft

|

House

10622 SE 179TH LN, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
Summit Greens 803 WOLF CREEK ST, CLERMONT, FL, 34711, Clermont, FL 34711
$335,000

2 beds

|

2 baths

|

1,420 sq ft

|

House

803 WOLF CREEK ST, CLERMONT, FL, 34711
Community: Summit Greens
The Villages® 1006 OREN AVE, THE VILLAGES, FL, 32159, The Villages, FL 32159
$137,500

2 beds

|

1 baths

|

876 sq ft

|

House

1006 OREN AVE, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 1757 PENNECAMP DR, THE VILLAGES, FL, 321..., The Villages, FL 32162
$725,000

3 beds

|

2 baths

|

1,856 sq ft

|

House

1757 PENNECAMP DR, THE VILLAGES, FL, 321...
Community: The Villages®
The Villages® 1856 POPPY CIR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$375,000

3 beds

|

2 baths

|

1,868 sq ft

|

House

1856 POPPY CIR, THE VILLAGES, FL, 32162
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.
Cresswind at Lake Harris 1725 POINT GRACE RD, TAVARES, FL, 32778, Tavares, FL 32778
$499,990

2 beds

|

2 baths

|

1,968 sq ft

|

House

1725 POINT GRACE RD, TAVARES, FL, 32778
Cindy Certified
1636 WILSON PRAIRIE CIR, GROVELAND, FL, ..., Groveland, FL 34736
$465,000

3 beds

|

2 baths

|

1,983 sq ft

|

House

1636 WILSON PRAIRIE CIR, GROVELAND, FL, ...
Highland Lakes 26616 EVERT ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$234,900

2 beds

|

2 baths

|

1,288 sq ft

|

House

26616 EVERT ST, LEESBURG, FL, 34748
Community: Highland Lakes
Trilogy® Orlando 217 CREPE MYRTLE DR, GROVELAND, FL, 3473..., Groveland, FL 34736
$485,000

3 beds

|

2 baths

|

2,151 sq ft

|

House

217 CREPE MYRTLE DR, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
The Villages® 6108 RODRIGUEZ LN, THE VILLAGES, FL, 321..., The Villages, FL 32163
$375,000

2 beds

|

2 baths

|

1,290 sq ft

|

Villa

6108 RODRIGUEZ LN, THE VILLAGES, FL, 321...
Community: The Villages®
Cindy Certified
209 LONG WAVE WAY, GROVELAND, FL, 34736, Groveland, FL 34736
$429,990

4 beds

|

2 baths

|

1,894 sq ft

|

House

209 LONG WAVE WAY, GROVELAND, FL, 34736
Cindy Certified
370 FREE RANGE DR, GROVELAND, FL, 34736, Groveland, FL 34736
$472,990

4 beds

|

3 baths

|

1,894 sq ft

|

House

370 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® 1068 BECKER AVE, THE VILLAGES, FL, 32163, The Villages, FL 32163
$439,000

3 beds

|

2 baths

|

1,617 sq ft

|

Villa

1068 BECKER AVE, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 2961 KRAMER CT, THE VILLAGES, FL, 32163, The Villages, FL 32163
$300,000

2 beds

|

2 baths

|

1,137 sq ft

|

Villa

2961 KRAMER CT, THE VILLAGES, FL, 32163
Community: The Villages®
Plantation at Leesburg 25040 BETTON HL, LEESBURG, FL, 34748, Leesburg, FL 34748
$179,000

2 beds

|

2 baths

|

1,428 sq ft

|

Manufactured Home

25040 BETTON HL, 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.
Plantation at Leesburg 24215 BELLE MEDE DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$417,500

3 beds

|

3 baths

|

2,755 sq ft

|

House

24215 BELLE MEDE DR, LEESBURG, FL, 34748
Legacy of Leesburg 27303 GINGERBREAD PL, LEESBURG, FL, 3474..., Leesburg, FL 34748
$388,790

3 beds

|

3 baths

|

2,287 sq ft

|

House

27303 GINGERBREAD PL, LEESBURG, FL, 3474...
Community: Legacy of Leesburg
The Villages® 1793 HARTFORD PATH, THE VILLAGES, FL, 32..., The Villages, FL 32162
$1,400,000

3 beds

|

2 baths

|

3,478 sq ft

|

House

1793 HARTFORD PATH, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 1314 TEAKWOOD LN, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$134,900

2 beds

|

1 baths

|

720 sq ft

|

Mobile Home

1314 TEAKWOOD LN, LADY LAKE, FL, 32159
Community: The Villages®
The Villages® 1705 MOUNT CROGHAN TRL, THE VILLAGES, FL..., The Villages, FL 32162
$585,000

3 beds

|

2 baths

|

2,094 sq ft

|

House

1705 MOUNT CROGHAN TRL, THE VILLAGES, FL...
Community: The Villages®
The Villages® 5825 FLINT LOOP, THE VILLAGES, FL, 32163, The Villages, FL 32163
$727,500

3 beds

|

2 baths

|

1,908 sq ft

|

House

5825 FLINT LOOP, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 7169 SE 172ND HAZELWOOD LOOP, THE VILLAG..., The Villages, FL 32162
$319,900

3 beds

|

2 baths

|

1,404 sq ft

|

House

7169 SE 172ND HAZELWOOD LOOP, THE VILLAG...
Community: The Villages®
Arlington Ridge 4400 BEDFORD WAY, LEESBURG, FL, 34748, Leesburg, FL 34748
$294,900

2 beds

|

2 baths

|

1,632 sq ft

|

Villa

4400 BEDFORD WAY, LEESBURG, FL, 34748
Community: Arlington Ridge
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
Heritage Hills 2862 CAPTIVA ST, CLERMONT, FL, 34711, Clermont, FL 34711
$544,900

4 beds

|

3 baths

|

2,562 sq ft

|

House

2862 CAPTIVA ST, CLERMONT, FL, 34711
Community: Heritage Hills
The Villages® 3553 CONNOR WAY, THE VILLAGES, FL, 32163, The Villages, FL 32163
$487,500

3 beds

|

2 baths

|

1,809 sq ft

|

House

3553 CONNOR WAY, 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.

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1,145 homes
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