Nowadays the wireless technology becomes popular and receives growing acceptance as a Broadband Wireless Access (BWA) system. Wireless system has potential success in its line-of-sight (LOS) and non line-of-sight (NLOS) conditions which operating with different frequency. Estimation of path loss is very important in initial deployment of wireless network and cell planning. Numerous path loss (PL) models (e.g. Okumura Model, Hata Model) are available to predict the propagation loss, but they are inclined to be limited to the lower frequency bands. Radio propagation is essential for emerging technologies with appropriate design deployment and management strategies for any wireless network. It is site specific and can vary significantly depending on terrain, frequency of operation, velocity of mobile terminal, interface sources and other dynamic factor. Accurate characterization of radio channel through key parameters and a mathematical model is important for predicting signal coverage, achievable data rates, specific performance attributes of alternative signaling and reception schemes. Empirical path loss models for macro cells such as free path loss, Hata Okumura, COST 231 Hata and ECC 33 models are analyzed and compared. The received signal strength is calculated with respect to distance to determine the model that can be adopted to minimize the number of handoffs and avoid ping pong effect. This paper proposes a comparison study of different propagation model such as Okumara-Hata model, COST 231 Hata model, ECC-33 to calculate path loss for highway and urban between Bhubaneswar and Cuttack. Comparative study with real time measurement obtained from Bharat Sanchar Nigam Limited (BSNL) a GSM based wireless networks for Bhubaneswar and Cuttack has been implemented. A suitable empirical model for different environments is to be proposed. Also calculate received signal strength for each environment under all three models and calculate the probability for each case. Keywords: Cellular mobile, Handoff, Path loss, Ping Pong, Received signal strength.