Call us at (352) 805-1035 to learn more about active adult communities in Leesburg

Leesburg, FL 55+ active adult communities & homes for sale - Page 22

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

Sort by:

Relevance

Relevance

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
Cindy Certified
180 BLUE STAR CT, TAVARES, FL, 32778, Tavares, FL 32778
$392,999

4 beds

|

3 baths

|

2,070 sq ft

|

House

180 BLUE STAR CT, TAVARES, FL, 32778
The Villages® 1534 HILLCREST DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$250,000

2 beds

|

2 baths

|

1,144 sq ft

|

House

1534 HILLCREST DR, LADY LAKE, FL, 32159
Community: The Villages®
Royal Highlands 5506 PRINCE CHARLES LN, LEESBURG, FL, 34..., Leesburg, FL 34748
$369,000

3 beds

|

2 baths

|

1,895 sq ft

|

House

5506 PRINCE CHARLES LN, LEESBURG, FL, 34...
Community: Royal Highlands
Stonecrest 11137 SE 173RD PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$315,900

3 beds

|

2 baths

|

1,695 sq ft

|

House

11137 SE 173RD PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Stonecrest 12421 SE 174TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$399,900

3 beds

|

2 baths

|

1,945 sq ft

|

House

12421 SE 174TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
The Villages® 716 TRUMAN AVE, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$228,900

2 beds

|

1 baths

|

1,124 sq ft

|

House

716 TRUMAN AVE, LADY LAKE, FL, 32159
Community: The Villages®
The Villages® 2054 PALO ALTO AVE, THE VILLAGES, FL, 32..., The Villages, FL 32159
$628,000

3 beds

|

2 baths

|

2,312 sq ft

|

House

2054 PALO ALTO AVE, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 1317 CARVELLO DR, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$310,000

3 beds

|

2 baths

|

1,527 sq ft

|

House

1317 CARVELLO DR, THE VILLAGES, FL, 3216...
Community: The Villages®
Stonecrest 17520 SE 112TH AVE, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$275,000

2 beds

|

2 baths

|

1,402 sq ft

|

House

17520 SE 112TH AVE, SUMMERFIELD, FL, 344...
Community: Stonecrest
Esplanade at McKinnon Groves 17806 SEDONA ST, WINTER GARDEN, FL, 3478..., Winter Garden, FL 34787
$630,000

2 beds

|

2 baths

|

1,843 sq ft

|

House

17806 SEDONA ST, WINTER GARDEN, FL, 3478...
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 25501 MAUREPAS LN, LEESBURG, FL, 34748, Leesburg, FL 34748
$440,000

3 beds

|

2 baths

|

2,945 sq ft

|

House

25501 MAUREPAS LN, LEESBURG, FL, 34748
Esplanade at McKinnon Groves 11221 CARDING MILL LN, WINTER GARDEN, FL..., Winter Garden, FL 34787
$750,000

3 beds

|

3 baths

|

2,085 sq ft

|

House

11221 CARDING MILL LN, WINTER GARDEN, FL...
Stonecrest 11584 SE 175TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$299,400

2 beds

|

2 baths

|

1,702 sq ft

|

House

11584 SE 175TH ST, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Spruce Creek South 9900 SE 175TH PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$377,000

3 beds

|

2 baths

|

2,349 sq ft

|

House

9900 SE 175TH PL, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
Cindy Certified
2974 SUPERMARINE RD, TAVARES, FL, 32778, Tavares, FL 32778
$379,432

4 beds

|

2 baths

|

2,110 sq ft

|

House

2974 SUPERMARINE RD, TAVARES, FL, 32778
Royal Highlands 4905 KELSO ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$269,000

3 beds

|

2 baths

|

1,571 sq ft

|

House

4905 KELSO ST, LEESBURG, FL, 34748
Community: Royal Highlands
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
Pennbrooke Fairways 1142 MEADOWBEND DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$240,000

2 beds

|

2 baths

|

1,770 sq ft

|

House

1142 MEADOWBEND DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
The Villages® 17755 SE 84TH SHELDON TER, THE VILLAGES,..., The Villages, FL 32162
$349,900

3 beds

|

2 baths

|

1,607 sq ft

|

House

17755 SE 84TH SHELDON TER, THE VILLAGES,...
Community: The Villages®
The Villages® 3561 COCHRAN ST, THE VILLAGES, FL, 32163, The Villages, FL 32163
$319,000

2 beds

|

2 baths

|

1,148 sq ft

|

House

3561 COCHRAN ST, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 9345 SE 177TH SIMONS LN, THE VILLAGES, F..., The Villages, FL 32162
$280,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

9345 SE 177TH SIMONS LN, THE VILLAGES, F...
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.
The Villages® 1575 HOLLYBERRY PL, THE VILLAGES, FL, 32..., The Villages, FL 32162
$349,900

3 beds

|

2 baths

|

1,392 sq ft

|

House

1575 HOLLYBERRY PL, THE VILLAGES, FL, 32...
Community: The Villages®
Legacy of Leesburg 5351 AURORA DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$369,900

4 beds

|

4 baths

|

3,125 sq ft

|

House

5351 AURORA DR, LEESBURG, FL, 34748
Community: Legacy of Leesburg
The Villages® 5833 ABNEY AVE, THE VILLAGES, FL, 32163, The Villages, FL 32163
$695,000

3 beds

|

3 baths

|

1,995 sq ft

|

House

5833 ABNEY AVE, THE VILLAGES, FL, 32163
Community: The Villages®
Baytree 623 JUNIPER WAY, TAVARES, FL, 32778, Tavares, FL 32778
$315,000

3 beds

|

2 baths

|

1,634 sq ft

|

House

623 JUNIPER WAY, TAVARES, FL, 32778
Community: Baytree
The Villages® 3812 INFINITY RUN, THE VILLAGES, FL, 321..., The Villages, FL 32163
$325,000

3 beds

|

2 baths

|

1,390 sq ft

|

House

3812 INFINITY RUN, THE VILLAGES, FL, 321...
Community: The Villages®
Kings Ridge 3605 WESTERHAM DR, CLERMONT, FL, 34711, Clermont, FL 34711
$316,500

3 beds

|

2 baths

|

1,572 sq ft

|

House

3605 WESTERHAM DR, CLERMONT, FL, 34711
Community: Kings Ridge
The Villages® 587 AUDREY LN, THE VILLAGES, FL, 32162, The Villages, FL 32162
$349,000

2 beds

|

2 baths

|

1,327 sq ft

|

Villa

587 AUDREY LN, THE VILLAGES, FL, 32162
Community: The Villages®
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
Cindy Certified
6837 SERPENT HAWK LN, HOWEY IN THE HILLS..., Howey In The Hills, FL 34737
$350,354

3 beds

|

2 baths

|

1,643 sq ft

|

House

6837 SERPENT HAWK LN, HOWEY IN THE HILLS...
Spruce Creek South 9498 SE 174TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$274,900

2 beds

|

2 baths

|

1,884 sq ft

|

House

9498 SE 174TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
The Villages® 892 NASH LOOP, THE VILLAGES, FL, 32162, The Villages, FL 32162
$259,900

2 beds

|

2 baths

|

1,090 sq ft

|

House

892 NASH LOOP, 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.
The Villages® 1718 MEANS LN, THE VILLAGES, FL, 32162, The Villages, FL 32162
$587,500

3 beds

|

2 baths

|

1,927 sq ft

|

House

1718 MEANS LN, THE VILLAGES, FL, 32162
Community: The Villages®
Legacy of Leesburg 27326 ORCHID GLADE ST, LEESBURG, FL, 347..., Leesburg, FL 34748
$290,000

3 beds

|

2 baths

|

1,480 sq ft

|

House

27326 ORCHID GLADE ST, LEESBURG, FL, 347...
Community: Legacy of Leesburg
The Villages® 116 CYPRESS RD, WILDWOOD, FL, 34785, Wildwood, FL 34785
$145,000

2 beds

|

2 baths

|

1,040 sq ft

|

Manufactured Home

116 CYPRESS RD, WILDWOOD, FL, 34785
Community: The Villages®
Royal Harbor 5052 CHINA SEA DR, TAVARES, FL, 32778, Tavares, FL 32778
$310,000

3 beds

|

2 baths

|

1,613 sq ft

|

House

5052 CHINA SEA DR, TAVARES, FL, 32778
Community: Royal Harbor
Cindy Certified
988 VINEYARD RIDGE RD, MINNEOLA, FL, 347..., Minneola, FL 34715
$469,900

4 beds

|

2 baths

|

2,215 sq ft

|

House

988 VINEYARD RIDGE RD, MINNEOLA, FL, 347...
Pennbrooke Fairways 420 GLEN ARBOR LN, LEESBURG, FL, 34748, Leesburg, FL 34748
$254,000

2 beds

|

2 baths

|

1,559 sq ft

|

Villa

420 GLEN ARBOR LN, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Cindy Certified
1013 SADIE RIDGE RD, CLERMONT, FL, 34715, Clermont, FL 34715
$444,500

4 beds

|

2 baths

|

1,846 sq ft

|

House

1013 SADIE RIDGE RD, CLERMONT, FL, 34715
The Villages® 914 MENDOZA BLVD, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$330,000

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

914 MENDOZA BLVD, 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
Stonecrest 17808 SE 115TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$329,900

3 beds

|

3 baths

|

2,282 sq ft

|

Villa

17808 SE 115TH CT, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Royal Highlands 5745 KING JAMES AVE, LEESBURG, FL, 34748, Leesburg, FL 34748
$269,999

2 beds

|

2 baths

|

1,280 sq ft

|

House

5745 KING JAMES AVE, LEESBURG, FL, 34748
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.

Frequently Asked Questions


Want more information about active adult communities around Leesburg?

Global - Lead Form - Buyer or Renter
*55places does not provide or maintain community HOA information.
By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting optout@55places.com. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

Want to learn more about 55+ communities in Leesburg?

Call us: (352) 805-1035
1,145 homes
Remove Boundaries ×
Map Satellite

Reinmlsx

The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: Oct 14, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us
Scroll to Top