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 15

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
Highland Lakes 5606 ROSEWALL CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$307,500

3 beds

|

2 baths

|

2,040 sq ft

|

House

5606 ROSEWALL CIR, LEESBURG, FL, 34748
Community: Highland Lakes
Royal Highlands 21738 KING RICHARDS WAY, LEESBURG, FL, 3..., Leesburg, FL 34748
$269,999

2 beds

|

2 baths

|

1,309 sq ft

|

House

21738 KING RICHARDS WAY, LEESBURG, FL, 3...
Community: Royal Highlands
The Villages® 1906 HARSTON TRL, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$365,000

3 beds

|

2 baths

|

1,488 sq ft

|

House

1906 HARSTON TRL, THE VILLAGES, FL, 3216...
Community: The Villages®
Trilogy® Orlando 122 FLAME VINE WAY, GROVELAND, FL, 34736, Groveland, FL 34736
$300,000

3 beds

|

2 baths

|

1,774 sq ft

|

House

122 FLAME VINE WAY, GROVELAND, FL, 34736
Community: Trilogy® Orlando
Esplanade at Highland Ranch 908 BRAEWOOD DR, CLERMONT, FL, 34715, Clermont, FL 34715
$624,450

3 beds

|

3 baths

|

2,396 sq ft

|

House

908 BRAEWOOD DR, CLERMONT, FL, 34715
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
Spruce Creek South 9486 SE 173RD PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$234,000

2 beds

|

2 baths

|

1,008 sq ft

|

House

9486 SE 173RD PL, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
The Villages® 1712 W SCHWARTZ BLVD, THE VILLAGES, FL, ..., The Villages, FL 32159
$225,000

2 beds

|

2 baths

|

1,144 sq ft

|

Manufactured Home

1712 W SCHWARTZ BLVD, THE VILLAGES, FL, ...
Community: The Villages®
The Villages® 1660 ORR TER, THE VILLAGES, FL, 32162, The Villages, FL 32162
$279,900

2 beds

|

2 baths

|

1,156 sq ft

|

House

1660 ORR TER, THE VILLAGES, FL, 32162
Community: The Villages®
Esplanade at Highland Ranch 2666 STARGRASS CIR, CLERMONT, FL, 34715, Clermont, FL 34715
$525,000

2 beds

|

2 baths

|

2,172 sq ft

|

House

2666 STARGRASS CIR, CLERMONT, FL, 34715
Cindy Certified
26144 AZALEA OAK CIR, GROVELAND, FL, 347..., Groveland, FL 34736
$358,420

3 beds

|

2 baths

|

1,695 sq ft

|

House

26144 AZALEA OAK CIR, GROVELAND, FL, 347...
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® 1613 SAN DIEGO ST, THE VILLAGES, FL, 321..., The Villages, FL 32159
$275,000

2 beds

|

2 baths

|

1,102 sq ft

|

House

1613 SAN DIEGO ST, THE VILLAGES, FL, 321...
Community: The Villages®
Stonecrest 11768 SE 176TH PLACE RD, SUMMERFIELD, FL..., Summerfield, FL 34491
$419,000

3 beds

|

2 baths

|

2,030 sq ft

|

House

11768 SE 176TH PLACE RD, SUMMERFIELD, FL...
Community: Stonecrest
The Villages® 746 ANGELITA AVE, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$285,000

2 beds

|

2 baths

|

1,121 sq ft

|

Villa

746 ANGELITA AVE, THE VILLAGES, FL, 3215...
Community: The Villages®
The Villages® 443 POMEGRANATE PATH, THE VILLAGES, FL, ..., The Villages, FL 32163
$454,500

3 beds

|

2 baths

|

1,895 sq ft

|

House

443 POMEGRANATE PATH, THE VILLAGES, FL, ...
Community: The Villages®
The Villages® 3037 LICCIARDELLO PATH, THE VILLAGES, FL..., The Villages, FL 32163
$569,000

3 beds

|

2 baths

|

1,922 sq ft

|

House

3037 LICCIARDELLO PATH, THE VILLAGES, FL...
Community: The Villages®
Cindy Certified
26148 AZALEA OAK CIR, GROVELAND, FL, 347..., Groveland, FL 34736
$376,850

5 beds

|

3 baths

|

2,133 sq ft

|

House

26148 AZALEA OAK CIR, GROVELAND, FL, 347...
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
Cindy Certified
26152 AZALEA OAK CIR, GROVELAND, FL, 347..., Groveland, FL 34736
$366,960

4 beds

|

2 baths

|

1,840 sq ft

|

House

26152 AZALEA OAK CIR, GROVELAND, FL, 347...
The Villages® 1563 HOLLYBERRY PL, THE VILLAGES, FL, 32..., The Villages, FL 32162
$339,000

3 beds

|

2 baths

|

1,527 sq ft

|

House

1563 HOLLYBERRY PL, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 628 BERMUDEZ CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$525,000

3 beds

|

2 baths

|

1,787 sq ft

|

Villa

628 BERMUDEZ CT, THE VILLAGES, FL, 32162
Community: The Villages®
Heritage Hills 3530 FAIRWATERS CT D, CLERMONT, FL, 3471..., Clermont, FL 34711
$269,899

2 beds

|

2 baths

|

1,374 sq ft

|

Villa

3530 FAIRWATERS CT D, CLERMONT, FL, 3471...
Community: Heritage Hills
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® 1674 GOVAN PL, THE VILLAGES, FL, 32162, The Villages, FL 32162
$394,000

3 beds

|

2 baths

|

1,368 sq ft

|

Villa

1674 GOVAN PL, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 9671 SE 168TH MAPLESONG LN, THE VILLAGES..., The Villages, FL 32162
$308,900

3 beds

|

2 baths

|

1,557 sq ft

|

House

9671 SE 168TH MAPLESONG LN, THE VILLAGES...
Community: The Villages®
The Villages® 16840 SE 97TH WILDWOOD CT, THE VILLAGES,..., The Villages, FL 32162
$359,900

3 beds

|

2 baths

|

1,527 sq ft

|

House

16840 SE 97TH WILDWOOD CT, THE VILLAGES,...
Community: The Villages®
Trilogy® Orlando 107 BALMY COAST RD, GROVELAND, FL, 34736, Groveland, FL 34736
$614,900

3 beds

|

3 baths

|

2,756 sq ft

|

House

107 BALMY COAST RD, GROVELAND, FL, 34736
Community: Trilogy® Orlando
Legacy of Leesburg 27336 PINE STRAW RD, LEESBURG, FL, 34748, Leesburg, FL 34748
$285,000

3 beds

|

2 baths

|

1,765 sq ft

|

House

27336 PINE STRAW RD, LEESBURG, FL, 34748
Community: Legacy of Leesburg
Spruce Creek South 17989 SE 106TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$239,900

3 beds

|

2 baths

|

1,450 sq ft

|

House

17989 SE 106TH CT, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
Royal Highlands 20512 QUEEN ALEXANDRA DR, LEESBURG, FL, ..., Leesburg, FL 34748
$339,900

3 beds

|

2 baths

|

2,008 sq ft

|

House

20512 QUEEN ALEXANDRA DR, LEESBURG, FL, ...
Community: Royal Highlands
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
The Villages® 1218 SANTOS PL, THE VILLAGES, FL, 32159, The Villages, FL 32159
$279,900

2 beds

|

2 baths

|

1,319 sq ft

|

House

1218 SANTOS PL, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 3425 CARBONDALE CT, THE VILLAGES, FL, 32..., The Villages, FL 32162
$329,900

3 beds

|

2 baths

|

1,392 sq ft

|

House

3425 CARBONDALE CT, THE VILLAGES, FL, 32...
Community: The Villages®
Stonecrest 17566 SE 112TH AVE, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$319,000

3 beds

|

2 baths

|

2,000 sq ft

|

House

17566 SE 112TH 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® 1049 JACKSON ST, THE VILLAGES, FL, 32162, The Villages, FL 32162
$325,000

2 beds

|

2 baths

|

1,187 sq ft

|

Villa

1049 JACKSON ST, THE VILLAGES, FL, 32162
Community: The Villages®
Trilogy® Orlando 78 BAYOU BEND RD, GROVELAND, FL, 34736, Groveland, FL 34736
$330,000

2 beds

|

2 baths

|

1,305 sq ft

|

House

78 BAYOU BEND RD, GROVELAND, FL, 34736
Community: Trilogy® Orlando
Lakeside Landings 5336 EDGEWATER WAY 11, OXFORD, FL, 34484, Oxford, FL 34484
$205,000

3 beds

|

2 baths

|

1,291 sq ft

|

Condo

5336 EDGEWATER WAY 11, OXFORD, FL, 34484
Community: Lakeside Landings
Arlington Ridge 4419 BENT CREEK LN, LEESBURG, FL, 34748, Leesburg, FL 34748
$525,000

2 beds

|

3 baths

|

2,333 sq ft

|

House

4419 BENT CREEK LN, LEESBURG, FL, 34748
Community: Arlington Ridge
The Villages® 2706 MORVEN PARK WAY, THE VILLAGES, FL, ..., The Villages, FL 32162
$309,999

2 beds

|

2 baths

|

1,248 sq ft

|

House

2706 MORVEN PARK WAY, THE VILLAGES, FL, ...
Community: The Villages®
The Villages® 112 LYONIA LN, WILDWOOD, FL, 34785, Wildwood, FL 34785
$197,000

2 beds

|

2 baths

|

1,664 sq ft

|

Manufactured Home

112 LYONIA LN, WILDWOOD, FL, 34785
Community: The Villages®
Royal Harbor 3204 ANTIGUA BAY LN, TAVARES, FL, 32778, Tavares, FL 32778
$334,900

3 beds

|

2 baths

|

1,785 sq ft

|

House

3204 ANTIGUA BAY LN, TAVARES, FL, 32778
Community: Royal Harbor
Kings Ridge 4075 KINGSLEY ST, CLERMONT, FL, 34711, Clermont, FL 34711
$334,900

3 beds

|

2 baths

|

1,782 sq ft

|

House

4075 KINGSLEY ST, 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® 16970 SE 94TH SUNNYBROOK CIR, THE VILLAG..., The Villages, FL 32162
$240,000

2 beds

|

2 baths

|

1,198 sq ft

|

House

16970 SE 94TH SUNNYBROOK CIR, THE VILLAG...
Community: The Villages®
Spruce Creek South 10298 SE 176TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$185,000

2 beds

|

2 baths

|

1,248 sq ft

|

House

10298 SE 176TH ST, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
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