1-407-575-5392
Menu

Chesterbrook Condo Leesburg Fl Homes For Sale

NEXT
PREV
Chesterbrook Condo Leesburg Fl Homes For Sale

 Chesterbrook Condo Leesburg Fl  

Chesterbrook in Leesburg FL is one of the few condo communities. Homes for sale there are the apartment style condos that some purchase for investment rental properties. The community has the old English cottage style appearance just without the cold rainy weather. Instead you get a community pool and beautiful nearby lakes and beaches.

Chesterbrook is a 55+ community. It is located on the southern end of Lake Griffin and it's primary entrance is on Newell Hill Road. Leesburg's East Main Street is less than 1/2 of a mile to it's south. A great location with a country feel but having all of downtown Leesburg just minutes away. You would never guess it standing in this community. 

 

Chesterbrook Community Pool

Above is the community pool which is centrally located in the community. 

Chesterbrook goes overlooked by many. This is because it is somewhat out of the way. However if you like the condo lifestyle I suggest checking it out. The cost of a home for sale here is very reasonable. In the previous 3 years they have sold for prices ranging from $28,500 to $58,000. In the past some have sold for up to $109,900. The HOA however is $425 monthly and there are restrictions other than age. The community was built between 1975 and 1980.

If you are interested in a 55+ community we would love to assist you. If you are interested, when they are available all of the Chesterbrook homes for sale or rent will be below.

 

 All Chesterbrook Homes For Sale  




All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independent verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. The source of the listing data is as follows: Stellar MLS (updated 8/23/26 6:20 PM) |

Listing Search



Translate Tool

Featured Listings
Altamonte Springs Real Estate
$1,149,000
5 BED
4 BATH
NEED MORE THAN JUST A HOUSE? Discover a rare 1.7 ACRE GATED ESTATE with NO HOA in Altamonte Springs, offering something ... Read More
Altamonte Springs Real Estate
$1,049,990
5 BED
3 BATH
IN PAST 3 YEARS HOME HAS BEEN EXTENSIVELY REMODELED/UPDATED, NEW FLOORING, KITCHEN,BATH CABINETS, SOLID SURFACE TOPS, RO... Read More
Apopka Real Estate
$1,010,000
5 BED
4 BATH
Welcome to your private slice of Central Florida. Situated on 1.25 fully fenced acres with no HOA, this custom-built hom... Read More
Apopka Real Estate
$1,999,000
3 BED
2 BATH
A private slice of paradise. Discover the extraordinary charm of this newly constructed rustic luxury cabin, ideally on ... Read More
Apopka Real Estate
$1,225,000
4 BED
2 BATH
4 Acres with Two Structures – Endless Potential! Nestled on approximately 4 acres, this exceptional property features tw... Read More
Apopka Real Estate
$1,250,000
5 BED
4 BATH
Under Construction. Experience luxury living from Nest Homes by Urban Perch, award-winning custom home builder. This tho... Read More
Apopka Real Estate
$1,350,000
4 BED
2 BATH
Fabulous Bear Lake Home with 85' of pristine waterfrontage and sweeping views of incredible 310-acre Bear Lake! Every in... Read More
Apopka Real Estate
$1,150,000
4 BED
3 BATH
The resort-style, waterfront homeownership dream you keep having might actually come true! Roughly an ACRE of lush, trop... Read More
Apopka Real Estate
$4,900,000
6 BED
6 BATH
Prime 5.32± acre development opportunity in the rapidly growing Kelly Park corridor near SR-429. Three contiguous parcel... Read More
Contact Wendy Morris

407-575-5392

Wendy Morris LLC

Licensed in the State of Florida
BK 3146762
16797 Broadwater Avenue
Winter Garden, Florida 34787

Your privacy is our utmost concern. We will never sell your personal information. Privacy Policy
©2026 windermereluxuryproperty.com - all rights reserved. | Site Map