Maxwell began his career as a youth player at Chelsea before moving onto Crystal Palace and Reading in 1999. He went on to join Isthmian League Premier Division club Grays Athletic in 2002. In 2003, he joined Scottish club Hamilton Academical making three appearances, two in the Scottish Second Division and one in the Scottish League Cup. The following season, 2004–05, he joined Raith Rovers in the Scottish First Division. He was released by mutual consent in January 2005 by manager Gordon Dalziel. Following his release from Raith, Maxwell subsequently joined Conference National club Dagenham & Redbridge. Failing to make an appearance for the Daggers, he went on to join Redbridge, and then joined Conference South outfit Basingstoke Town on August 2005. However, he made just two league appearances in August before he departed, and eventually joined Margate in October. In January 2006, Maxwell joined Bishop's Stortford on loan from Gravesend & Northfleet, making his début in the 3–1 away loss against Weymouth on 5 January. He signed for Welsh Premier League club Llanelli in the close season of 2006, featuring in their UEFA Cupqualifying ties. In the first leg of the first round of qualifying on 13 July against Swedish club Gefle IF, he came on as a 90th minute substitute for Craig Williams in the 1–2 away win. In the second leg on 27 July, Maxwell started the match before being substituted in injury time for Richard Appleby. The game finished 0–0, meaning Llanelli qualified 2–1 on aggregate. Llanelli were beaten 6–1 on aggregate in the second qualifying round by Danish club Odense BK. Maxwell received interest from Hartlepool but decided not to go on trial for family reasons. Maxwell joined Isthmian League Premier Division club Tonbridge Angels in October 2010, before going on to join a number of non-League clubs including Braintree Town and Boreham Wood through 2006 to 2007. He then joined Northern Irish club Larne, before returning to England with Welling United. Having trialled for St Albans City in the 2009–10 pre-season, he eventually signed for the Conference South club in September 2009. He made just two appearances for the Saints, both coming on as a substitute. His début was in the 1–0 away defeat to Heybridge Swifts in the FA Cup Second Round Qualifying on 26 September, replacing Godfrey Poku in the 46th minute. Maxwell went on to play for Waltham Abbey, prior to signing for Harlow Town in October 2011, before leaving at the end of the season in July 2012. At the start of the 2012–13 season, Maxwell re-joined Grays Athletic in the Isthmian League Division One North alongside three other players. He rejoined Grays again at the start of the 2013–14 season as a player-coach. In March 2014 he left and went to Heybridge Swifts, and at the start of June 2014 he signed for A.F.C. Sudbury. He became the A.F.C. Sudbury fitness coach and played also until the middle of October 2014. His contract was terminated on 8 November 2014 after a discipline problem, and on 20 November he signed for Witham Town. He did not make many appearances at the Spa Road club during the 2014–15 season, but featured on the bench against Tonbridge Angels amongst others. On the eve of the 2015–16 season, 7 August 2015 he had re-joined one of his former clubs, Heybridge Swifts. Ware announced he had joined them on 4 August 2015 and he was still there in October 2015, however on 5 December he was back playing for Heybridge Swifts. In January 2017 he left his position as a player-coach at Waltham Forest, alongside manager Kem Kemal. Later that year he joined Ware for his second spell, but left again in December 2017 as Kem Kamal was replaced by Craig Edwards as the manager. Yet another managerial change at Waltham Forest, later to be renamed to Walthamstow, saw Maxwell replace Qayum Shakoor for the position in February 2018. He also registered as a player. On 23 January 2020, Maxwell left Walthamstow after a mutual decision with the club to part ways.
