Below you can view all the condos for sale in the Chesterbrook subdivision located in Leesburg Florida. Listings in Chesterbrook are updated daily from data we receive from the Orlando multiple listing service.

To learn more about any of these condos or to receive custom notifications when a new property is listed for sale in Chesterbrook, give us a call at 407-641-2236.

7 Results

Chesterbrook Leesburg Florida Condos For Sale

Chesterbrook For Sale $109,000

Charming condo with a Tudor-style exterior, lush landscaping, and covered entryway at 500 Newell Hill Rd # 113D, Leesburg, FL 34748
View Details 33 Photos
Scenic aerial view of the community with lake views, lush trees, and well-maintained buildings at 500 Newell Hill Rd # 113D, Leesburg, FL 34748
Bright living room featuring hardwood floors, modern decor, and ample closet space at 500 Newell Hill Rd # 113D, Leesburg, FL 34748
Cozy living room with modern furniture, a ceiling fan, and a large window for natural light at 500 Newell Hill Rd # 113D, Leesburg, FL 34748
On Market For 22 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1413

  • Year Built

    1980

  • $/SqFt

    $77

ARE YOU READY TO start living the lifestyle you’ve always imagined. DOWN HOME REALTY, LLLP.

Chesterbrook For Sale $90,000

Reduced By $9,900

Exterior view of Tudor-style townhome with lush landscaping and private entrance at 500 Newell Hill Rd # 111A, Leesburg, FL 34748
View Details 27 Photos
Exterior view of Tudor-style townhome with lush landscaping and private entrance at 500 Newell Hill Rd # 111A, Leesburg, FL 34748
Exterior stairs to a unit featuring Tudor-style accents, mailbox, light fixture, and door at 500 Newell Hill Rd # 111A, Leesburg, FL 34748
A unit's front entrance features Tudor-style accents, mailbox, light fixture, and door knocker at 500 Newell Hill Rd # 111A, Leesburg, FL 34748
On Market For 51 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1413

  • Year Built

    1980

  • $/SqFt

    $64

Call today for your private showing! ERA GRIZZARD REAL ESTATE.

Chesterbrook For Sale $100,000

Striking clubhouse entrance featuring Tudor-style accents and well-maintained landscaping at 500 Newell Hill Rd # 113A, Leesburg, FL 34748
View Details 23 Photos
Sun-filled living room with stylish furniture, modern decor, and wood-look floors at 500 Newell Hill Rd # 113A, Leesburg, FL 34748
Cozy dining area featuring modern table, stylish seating, and adjacent updated kitchen at 500 Newell Hill Rd # 113A, Leesburg, FL 34748
Well-lit kitchen featuring granite countertops, modern appliances, and sleek white cabinets at 500 Newell Hill Rd # 113A, Leesburg, FL 34748
On Market For 60 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1413

  • Year Built

    1980

  • $/SqFt

    $71

Whether you’re searching for a stylish and comfortable place to call home or a prime investment opportunity, this move-in-ready unit is waiting for you! KELLER WILLIAMS REALTY AT THE LAKES.

Chesterbrook For Sale $60,000

Reduced By $5,000

Attractive multi-Gathering building featuring tudor-style architecture and well-maintained landscaping at 500 Newell Hill Rd # D, Leesburg, FL 34748
View Details 32 Photos
Picture of a charming building featuring a tudor-style facade and a well-kept parking lot at 500 Newell Hill Rd # D, Leesburg, FL 34748
View of a tudor-style building with a meticulously maintained parking area at 500 Newell Hill Rd # D, Leesburg, FL 34748
Attractive community sign showing the logo and an American flag at 500 Newell Hill Rd # D, Leesburg, FL 34748
*POTENTIAL GREAT VALUE
On Market For 65 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1134

  • Year Built

    1975

  • $/SqFt

    $53

The Seller will offer $3,000 towards closing costs or updates!! Make your appointment today! RIGHT REALTY CONNECTION, INC..

Chesterbrook For Sale $112,000

Reduced By $4,000

Inviting exterior view of Tudor-style condos with well-maintained landscaping and ample parking at 500 Newell Hill Rd # 107C, Leesburg, FL 34748
View Details 25 Photos
Close up of unit's entryway, featuring a two-story portico and well-manicured shrubs at 500 Newell Hill Rd # 107C, Leesburg, FL 34748
Exterior shot of the front door showcasing the Tudor architecture and unit design at 500 Newell Hill Rd # 107C, Leesburg, FL 34748
Open-concept living and dining room with wood laminate flooring and neutral wall paint at 500 Newell Hill Rd # 107C, Leesburg, FL 34748
On Market For 66 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1413

  • Year Built

    1979

  • $/SqFt

    $79

Come see why life at Chesterbrook feels like home. KELLER WILLIAMS ADVANTAGE REALTY.

Chesterbrook Pended $65,000

Reduced By $10,000

Charming Tudor-style condo featuring a unique architectural style at 500 Newell Hill Rd # 111D, Leesburg, FL 34748
View Details 20 Photos
Spacious living room featuring sleek wood flooring and a mounted television at 500 Newell Hill Rd # 111D, Leesburg, FL 34748
Open-concept dining room with modern light fixture and flooring at 500 Newell Hill Rd # 111D, Leesburg, FL 34748
Bright living room with large window, hardwood floors, and simple décor at 500 Newell Hill Rd # 111D, Leesburg, FL 34748
*POTENTIAL GREAT VALUE
On Market For 57 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1413

  • Year Built

    1980

  • $/SqFt

    $46

*Please note that this is a cash-only sale due to the roofs needing repairs/replacement. KELLER WILLIAMS ELITE PARTNERS III REALTY.

Chesterbrook For Sale $84,900

Reduced By $15,000

Exterior view of charming two-story building at 500 Newell Hill Rd # 104 B, Leesburg, FL 34748
View Details 25 Photos
Exterior view of building entrance with stairs at 500 Newell Hill Rd # 104 B, Leesburg, FL 34748
Building entrance with security door and mailboxes at 500 Newell Hill Rd # 104 B, Leesburg, FL 34748
Living Room with sofa, coffee table, and TV at 500 Newell Hill Rd # 104 B, Leesburg, FL 34748
On Market For 430 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1134

  • Year Built

    1975

  • $/SqFt

    $75

A great location that is close to downtown Leesburg & UF Hospital. ERA GRIZZARD REAL ESTATE.

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Similar Properties For Sale

Area Stats

These statistics are updated daily from the My Florida Regional MLS. For further analysis or to obtain statistics not shown below please call EasyStreet Realty at 407-641-2236 and speak with one of our real estate consultants.

Popular Condos

City
Avg Price
Median Price
Available
Distressed
Reduced
Avg DOM
Debary
$322,029
$333,520
26
0.0%
34.6%
75

Deltona
$175,984
$174,900
20
0.0%
50.0%
80

Eustis
$240,371
$199,900
7
0.0%
85.7%
150

Howey In The Hills
$377,676
$364,994
21
4.8%
52.4%
140

Lady Lake
$297,435
$279,750
8
0.0%
87.5%
76

Lake Mary
$299,300
$297,000
104
0.0%
51.0%
88

Mount Dora
$275,663
$276,500
19
0.0%
63.2%
161

Orange City
$198,945
$198,217
7
0.0%
28.6%
37

Tavares
$251,609
$269,990
39
2.6%
66.7%
116

The Villages
$339,767
$319,950
178
0.6%
63.5%
77

Yalaha
$313,300
$299,900
3
0.0%
66.7%
72

EasyStreet

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