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 9

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
Legacy of Leesburg 26958 HONEYMOON AVE, LEESBURG, FL, 34748, Leesburg, FL 34748
$275,500

2 beds

|

2 baths

|

1,871 sq ft

|

House

26958 HONEYMOON AVE, LEESBURG, FL, 34748
Community: Legacy of Leesburg
Spruce Creek South 17726 SE 106TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$260,900

3 beds

|

2 baths

|

1,726 sq ft

|

House

17726 SE 106TH TER, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
The Villages® 2595 CARIBE DR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$575,000

3 beds

|

2 baths

|

1,939 sq ft

|

House

2595 CARIBE DR, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 17728 SE 81ST WYNSTONE AVE, THE VILLAGES..., The Villages, FL 32162
$325,000

3 beds

|

2 baths

|

1,496 sq ft

|

House

17728 SE 81ST WYNSTONE AVE, THE VILLAGES...
Community: The Villages®
The Villages® 4529 SAMANTHA CT, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$649,900

3 beds

|

3 baths

|

2,119 sq ft

|

House

4529 SAMANTHA CT, THE VILLAGES, FL, 3216...
Community: The Villages®
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
Plantation at Leesburg 4003 PLANTATION BLVD, LEESBURG, FL, 3474..., Leesburg, FL 34748
$299,900

2 beds

|

2 baths

|

1,865 sq ft

|

House

4003 PLANTATION BLVD, LEESBURG, FL, 3474...
Cindy Certified
6736 SPOTTED EAGLE LOOP, HOWEY IN THE HI..., Howey In The Hills, FL 34737
$375,999

4 beds

|

2 baths

|

2,008 sq ft

|

House

6736 SPOTTED EAGLE LOOP, HOWEY IN THE HI...
Plantation at Leesburg 24242 BELLE MEDE DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$349,000

3 beds

|

2 baths

|

1,728 sq ft

|

House

24242 BELLE MEDE DR, LEESBURG, FL, 34748
The Villages® 2112 KERWOOD LOOP, THE VILLAGES, FL, 321..., The Villages, FL 32162
$450,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

2112 KERWOOD LOOP, THE VILLAGES, FL, 321...
Community: The Villages®
The Villages® 3193 KRANZ AVE, THE VILLAGES, FL, 32163, The Villages, FL 32163
$460,000

3 beds

|

2 baths

|

1,945 sq ft

|

House

3193 KRANZ AVE, 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.
The Villages® 3785 WHITNEY PARK LN, GREENACRES, FL, 33..., Greenacres, FL 33463
$549,000

4 beds

|

3 baths

|

2,078 sq ft

|

House

3785 WHITNEY PARK LN, GREENACRES, FL, 33...
Community: The Villages®
The Villages® 1042 SOLEDAD WAY, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$449,900

3 beds

|

2 baths

|

2,360 sq ft

|

House

1042 SOLEDAD WAY, THE VILLAGES, FL, 3215...
Community: The Villages®
Trilogy® Orlando 189 BALMY COAST RD, GROVELAND, FL, 34736, Groveland, FL 34736
$360,000

3 beds

|

2 baths

|

1,820 sq ft

|

House

189 BALMY COAST RD, GROVELAND, FL, 34736
Community: Trilogy® Orlando
Plantation at Leesburg 4617 MANOR VIEW DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$285,900

3 beds

|

2 baths

|

1,858 sq ft

|

House

4617 MANOR VIEW DR, LEESBURG, FL, 34748
Royal Harbor 4925 PORTSMOUTH ST, TAVARES, FL, 32778, Tavares, FL 32778
$285,000

3 beds

|

2 baths

|

1,469 sq ft

|

House

4925 PORTSMOUTH ST, TAVARES, FL, 32778
Community: Royal Harbor
The Villages® 770 GOLIATH PL, THE VILLAGES, FL, 32162, The Villages, FL 32162
$349,900

3 beds

|

2 baths

|

1,512 sq ft

|

House

770 GOLIATH PL, 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
The Villages® 17760 SE 84TH PEYTON CT, THE VILLAGES, F..., The Villages, FL 32162
$315,000

2 beds

|

2 baths

|

1,165 sq ft

|

Villa

17760 SE 84TH PEYTON CT, THE VILLAGES, F...
Community: The Villages®
Summit Chase Villas 12422 CLUBHOUSE CT, TAVARES, FL, 32778, Tavares, FL 32778
$180,000

2 beds

|

2 baths

|

935 sq ft

|

Villa

12422 CLUBHOUSE CT, TAVARES, FL, 32778
Community: Summit Chase Villas
Spruce Creek South 17760 SE 108 AVE, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$249,990

2 beds

|

2 baths

|

1,544 sq ft

|

House

17760 SE 108 AVE, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
The Villages® 939 EBLING LOOP, THE VILLAGES, FL, 32163, The Villages, FL 32163
$449,900

3 beds

|

2 baths

|

1,611 sq ft

|

House

939 EBLING LOOP, 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.
Royal Highlands 5049 ST ANDREWS ARC, LEESBURG, FL, 34748, Leesburg, FL 34748
$369,900

3 beds

|

2 baths

|

2,147 sq ft

|

House

5049 ST ANDREWS ARC, LEESBURG, FL, 34748
Community: Royal Highlands
Plantation at Leesburg 25121 MERIWEATHER RD, LEESBURG, FL, 3474..., Leesburg, FL 34748
$336,000

3 beds

|

2 baths

|

1,761 sq ft

|

House

25121 MERIWEATHER RD, LEESBURG, FL, 3474...
Esplanade at Highland Ranch 1279 ZEEK RIDGE ST, CLERMONT, FL, 34715, Clermont, FL 34715
$675,000

3 beds

|

3 baths

|

2,311 sq ft

|

House

1279 ZEEK RIDGE ST, CLERMONT, FL, 34715
The Villages® 730 SAN MARINO DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$405,000

2 beds

|

3 baths

|

1,921 sq ft

|

House

730 SAN MARINO DR, THE VILLAGES, FL, 321...
Community: The Villages®
Kings Ridge 3821 AVON CT, CLERMONT, FL, 34711, Clermont, FL 34711
$395,000

2 beds

|

2 baths

|

1,792 sq ft

|

House

3821 AVON CT, CLERMONT, FL, 34711
Community: Kings Ridge
Heritage Hills 3541 BELLAND CIR C, CLERMONT, FL, 34711, Clermont, FL 34711
$255,000

2 beds

|

2 baths

|

1,374 sq ft

|

Villa

3541 BELLAND CIR C, CLERMONT, FL, 34711
Community: Heritage Hills
The Villages® 3565 IDLEWOOD LOOP, THE VILLAGES, FL, 32..., The Villages, FL 32162
$289,900

3 beds

|

2 baths

|

1,240 sq ft

|

House

3565 IDLEWOOD LOOP, THE VILLAGES, FL, 32...
Community: The Villages®
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
Pennbrooke Fairways 32732 TIMBERWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$229,900

2 beds

|

2 baths

|

1,310 sq ft

|

House

32732 TIMBERWOOD DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Trilogy® Orlando 649 CONSERVATION BLVD, GROVELAND, FL, 34..., Groveland, FL 34736
$419,990

3 beds

|

3 baths

|

1,905 sq ft

|

House

649 CONSERVATION BLVD, GROVELAND, FL, 34...
Community: Trilogy® Orlando
The Villages® 1020 NELL WAY, THE VILLAGES, FL, 32159, The Villages, FL 32159
$150,000

2 beds

|

2 baths

|

864 sq ft

|

Mobile Home

1020 NELL WAY, THE VILLAGES, 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.
Royal Harbor 5693 GULF STREAM ST, TAVARES, FL, 32778, Tavares, FL 32778
$349,900

3 beds

|

2 baths

|

1,830 sq ft

|

House

5693 GULF STREAM ST, TAVARES, FL, 32778
Community: Royal Harbor
The Villages® 5693 BLANCHARD LN, THE VILLAGES, FL, 321..., The Villages, FL 32163
$995,000

3 beds

|

3 baths

|

1,977 sq ft

|

House

5693 BLANCHARD LN, THE VILLAGES, FL, 321...
Community: The Villages®
Scottish Highlands 822 DUNDEE CIR, LEESBURG, FL, 34788, Leesburg, FL 34788
$215,000

2 beds

|

2 baths

|

1,414 sq ft

|

House

822 DUNDEE CIR, LEESBURG, FL, 34788
Community: Scottish Highlands
The Villages® 6036 ALTMAN AVE, THE VILLAGES, FL, 32163, The Villages, FL 32163
$289,000

2 beds

|

2 baths

|

1,337 sq ft

|

House

6036 ALTMAN AVE, THE VILLAGES, FL, 32163
Community: The Villages®
Plantation at Leesburg 25606 BELLE ALLIANCE, LEESBURG, FL, 3474..., Leesburg, FL 34748
$180,000

2 beds

|

2 baths

|

1,120 sq ft

|

Manufactured Home

25606 BELLE ALLIANCE, LEESBURG, FL, 3474...
Royal Highlands 21709 KING RICHARDS WAY, LEESBURG, FL, 3..., Leesburg, FL 34748
$249,900

2 beds

|

2 baths

|

1,322 sq ft

|

House

21709 KING RICHARDS WAY, LEESBURG, FL, 3...
Community: Royal Highlands
The Villages® 1089 VANCE TRL, THE VILLAGES, FL, 32162, The Villages, FL 32162
$1,495,247

4 beds

|

3 baths

|

3,000 sq ft

|

House

1089 VANCE TRL, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 16804 SE 96TH CHAPELWOOD CIR 52, THE VIL..., The Villages, FL 32162
$288,000

3 beds

|

2 baths

|

1,485 sq ft

|

House

16804 SE 96TH CHAPELWOOD CIR 52, THE VIL...
Community: The Villages®
Want to learn more about 55+ communities in Leesburg? 55places can help!
Questions? Call us: (352) 805-1035
Highland Lakes 5536 ROSEWALL CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$210,000

2 beds

|

2 baths

|

1,350 sq ft

|

Villa

5536 ROSEWALL CIR, LEESBURG, FL, 34748
Community: Highland Lakes
The Villages® 16838 SE 93RD CUTHBERT CIR, THE VILLAGES..., The Villages, FL 32162
$349,900

3 beds

|

2 baths

|

1,648 sq ft

|

House

16838 SE 93RD CUTHBERT CIR, THE VILLAGES...
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.

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