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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 407-967-1435.

9 Results

Chesterbrook Leesburg Florida Condos For Sale

Chesterbrook For Sale $89,000

Reduced By $1,000

Exterior view of building, showcasing unique architectural details at 500 Newell Hill Rd # 108C, Leesburg, FL 34748
View Details 11 Photos
Community sign for Chesterbrook, a 55+ condominium community at 500 Newell Hill Rd # 108C, Leesburg, FL 34748
Quaint community clubhouse with a charming, inviting entrance at 500 Newell Hill Rd # 108C, Leesburg, FL 34748
Refreshing community pool, ideal for relaxation and recreation at 500 Newell Hill Rd # 108C, Leesburg, FL 34748
*POTENTIAL GREAT VALUE
On Market For 68 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1413

  • Year Built

    1980

  • $/SqFt

    $63

Don't miss this happy home! Furnished. CENTURY 21 ALTON CLARK.

Chesterbrook For Sale $112,000

Condo building exterior with Tudor-style architecture at 500 Newell Hill Rd # 107C, Leesburg, FL 34748
View Details 22 Photos
Chesterbrook community sign, A 55+ Condominium at 500 Newell Hill Rd # 107C, Leesburg, FL 34748
Inviting exterior of a two-story building with ample parking at 500 Newell Hill Rd # 107C, Leesburg, FL 34748
Well-lit entryway with a view into a living area with hardwood floors at 500 Newell Hill Rd # 107C, Leesburg, FL 34748
On Market For 97 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1413

  • Year Built

    1979

  • $/SqFt

    $79

Don’t wait—schedule a tour today! KELLER WILLIAMS CLASSIC.

Chesterbrook For Sale $92,000

Reduced By $1,500

Building exterior featuring a staircase and entrance at 500 Newell Hill Rd # 115C, Leesburg, FL 34748
View Details 24 Photos
Chesterbrook community entrance sign for 55+ condo residents at 500 Newell Hill Rd # 115C, Leesburg, FL 34748
Simple kitchen with white cabinets, double sink, and appliances at 500 Newell Hill Rd # 115C, Leesburg, FL 34748
Efficient kitchen featuring white cabinets and black appliances at 500 Newell Hill Rd # 115C, Leesburg, FL 34748
On Market For 98 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1134

  • Year Built

    1980

  • $/SqFt

    $81

Schedule your viewing today and discover why this could be your perfect new home or investment property. ~No blind offers~ LOVELAND PROPERTIES.

Chesterbrook For Sale $93,500

Exterior view of a building entrance with unique architectural details and landscaping at 500 Newell Hill Rd # 101C, Leesburg, FL 34748
View Details 7 Photos
Kitchen with white cabinets, granite countertops, and stainless steel appliances at 500 Newell Hill Rd # 101C, Leesburg, FL 34748
Kitchen features include gas stove, microwave, and built-in oven at 500 Newell Hill Rd # 101C, Leesburg, FL 34748
Kitchen with white cabinets, granite countertops, and a freestanding refrigerator at 500 Newell Hill Rd # 101C, Leesburg, FL 34748
On Market For 147 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1134

  • Year Built

    1975

  • $/SqFt

    $82

This 2nd Floor Condo Is Turnkey And Ready For You To Move Into - Take Your Cloths And Toothbrush And You Are Moved - Priced To Sell - Call To See This Beauty RE/MAX FOXFIRE - LADY LAKE.

Chesterbrook For Sale $95,000

Front view of charming two-story building at 500 Newell Hill Rd # 115A, Leesburg, FL 34748
View Details 28 Photos
Front view of a two-story building with unique architecture at 500 Newell Hill Rd # 115A, Leesburg, FL 34748
Living room with a large ornate sofa and tiled floor at 500 Newell Hill Rd # 115A, Leesburg, FL 34748
Living room featuring a unique sofa and built-in shelving at 500 Newell Hill Rd # 115A, Leesburg, FL 34748
On Market For 174 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1134

  • Year Built

    1980

  • $/SqFt

    $84

Approximately 60 minutes to East/West Coast Beaches, Orlando/Daytona International Airports, Disney plus other great theme parks. Come visit, easy to see! SUCCESS INVESTMENT REALTY.

Chesterbrook For Sale $84,900

Reduced By $14,600

Two-story building with a unique architectural design at 500 Newell Hill Rd # 107A, Leesburg, FL 34748
View Details 25 Photos
Front view of a two-story building with landscaping at 500 Newell Hill Rd # 107A, Leesburg, FL 34748
Building entry with stairs and a security system at 500 Newell Hill Rd # 107A, Leesburg, FL 34748
Spacious living room with large windows and ceiling fan at 500 Newell Hill Rd # 107A, Leesburg, FL 34748
*POTENTIAL GREAT VALUE
On Market For 159 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1413

  • Year Built

    1979

  • $/SqFt

    $60

Community pool, recreation building and shuffleboard. ERA GRIZZARD REAL ESTATE.

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 252 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.

Chesterbrook For Sale $135,000

Reduced By $24,900

Exterior view of charming two-story building with brown roof at 500 Newell Hill Rd # 104 D, Leesburg, FL 34748
View Details 37 Photos
Exterior view of charming two-story building with brown roof at 500 Newell Hill Rd # 104 D, Leesburg, FL 34748
Community pool with lounge chairs and surrounding buildings at 500 Newell Hill Rd # 104 D, Leesburg, FL 34748
Living room with light beige couch, glass coffee table, and hardwood floors at 500 Newell Hill Rd # 104 D, Leesburg, FL 34748
On Market For 308 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1134

  • Year Built

    1975

  • $/SqFt

    $119

Call now to schedule your appointment. Bring offers; ONLY CASH OFFERS PREFERRED RE BROKERS III.

Chesterbrook For Sale $120,000

Reduced By $15,000

Exterior view of two story building with stairs at 500 Newell Hill Rd # 106A, Leesburg, FL 34748
View Details 30 Photos
Aerial view of building with parking at 500 Newell Hill Rd # 106A, Leesburg, FL 34748
Community pool with lounge chairs at 500 Newell Hill Rd # 106A, Leesburg, FL 34748
Living room with tiled floors and sofa at 500 Newell Hill Rd # 106A, Leesburg, FL 34748
On Market For 341 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1134

  • Year Built

    1979

  • $/SqFt

    $106

1.5 hrs to either coast, East or West. Bring Offers; only Cash! PREFERRED RE BROKERS III.

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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 407-967-1435 and speak with one of our real estate consultants.

Popular Condos

City
Avg Price
Median Price
Available
Distressed
Reduced
Avg DOM
Debary
$244,400
$229,900
7
0.0%
71.4%
103

Deltona
$169,744
$167,950
16
0.0%
56.2%
109

Eustis
$308,475
$237,000
4
0.0%
75.0%
86

Howey In The Hills
$356,088
$308,740
30
0.0%
46.7%
95

Lady Lake
$306,235
$287,235
4
0.0%
25.0%
49

Lake Mary
$337,363
$312,000
70
0.0%
48.6%
86

Mount Dora
$359,600
$310,950
22
0.0%
45.5%
113

Tavares
$237,325
$262,500
20
5.0%
55.0%
97

The Villages
$372,995
$349,900
151
0.0%
51.0%
70

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