Severed from a group representation constituency where the People's Action Party eked out its second-closest win in 2011.
Helmed by a first-term MP, the heavily pregnant Ms Tin Pei Ling.
MacPherson - on the electoral map as a single seat again after being part of Marine Parade GRC in 2011 - appears to be ripe for the opposition's plucking.
But a look at its history and demographics suggests the single-member constituency might be a safer seat than it seems.
Current MacPherson division MP Ms Tin may be a first-termer, but PAP activists are confident about her going it alone, assuming she will be fielded there again.
Says branch secretary Rosemary Lim, referring to MacPherson's long history of being an SMC: "We are optimistic that we will be able to perform well, because we have been on our own for a long time."
Admittedly, MacPherson was part of the GRC where the PAP saw its second-lowest winning vote share in 2011, with 56.7 per cent against the National Solidarity Party. But that figure disguises MacPherson's own performance. The ward reportedly had the second-highest PAP vote share within the GRC.
It also has a history of PAP support. In each of the six elections in which MacPherson was contested as a single seat, the PAP won no less than 65 per cent of the vote.
Its worst performance was in 1997, when MacPherson was carved out as a single seat in response to Singapore Democratic Party leader Chee Soon Juan's challenge to the PAP's Matthias Yao.
Mr Yao won with 65.1 per cent of the vote, and bettered that performance in the next two elections.
In 2001 and 2006, Mr Yao took 83.7 per cent of the vote against Democratic Progressive Party's Tan Soo Phuan and 68.5 per cent against Singapore Democratic Alliance's Sin Kek Tong respectively.
Ward demographics may have worked in its favour. It has a higher than average proportion of public rental residents and senior citizens, two groups traditionally seen as PAP supporters.
Madam Lee Soon Ying, 76, is one long-time PAP voter. The retiree finds Ms Tin "very good, very helpful". She says: "I didn't like the opposition (in 2011) because it felt like they did not really care about us."
Updated figures are not available, but in 2010, only 9.3 per cent of MacPherson residents lived in private housing. And 61.8 per cent lived in three-room or smaller HDB flats, much higher than the islandwide proportion of about a quarter.
Granted, MacPherson's boundaries have changed since 2006 to include private housing around Jalan Anggerek and Jalan Belangkas.
Private housing residents are seen as more open to the idea of voting for the opposition. Landed property resident Ryan Cheong, 24, declines to reveal any party preference but says he will vote for whoever seems able to "listen to residents and make the necessary changes".
However, the new boundaries also take in HDB blocks around Balam Road, north of Circuit Road.
In any case, these were already the internal boundaries in 2011.
One complication for opposition hopefuls is that both the Workers' Party and NSP have stated their intention to contest MacPherson, though WP chief Low Thia Khiang said the WP would "avoid three-cornered fights as far as possible".
If the WP ventures into MacPherson, where it has not stood since 1972, it will find some supporters, like retiree Tham Yoke Guang, 76. "If the WP come here, I will welcome them. They're my favourite," says Mr Tham, who went to Punggol East during its 2013 by-election to attend the WP rallies.
The WP's cachet as the most successful opposition party could help in a three-cornered fight, as it may interest opposition-friendly voters who may not vote for the NSP.
Says university student Poh Jun Jie, 22: "I don't think it's good if we have so many PAP members in Parliament, so I'm likely to vote for the opposition, but it depends on the party. WP has more resources, even though they have some issues in (AHPETC). If they come here, I might vote for them."
Ms Tin says the branch is "prepared for different scenarios".
Then there is Ms Tin's upcoming temporary absence - she is due to give birth this week. But the PAP's Ms Lim says: "We have all worked out our plans for when she's away."
Ms Tin confirms it will be "business as usual" while she is away, and expects to be back in action after the traditional month-long confinement period for new mothers.
Her team is in place and communication channels have been set up, she says. "I am grateful to have a great team... I am confident I will be able to cope with the demands of GE and as a mother of a newborn."
MS TIN A FAMILIAR FACE
Unlike the opposition candidates who have yet to be announced, Ms Tin is a familiar face. This election will be the culmination of her last four years on the ground, after a bruising 2011 campaign where netizens questioned her maturity as the PAP's youngest candidate, at 27.
There is little sign that anyone else might be fielded, with Marine Parade GRC's anchor minister Tan Chuan-Jin expressing support for Ms Tin's solo contest. "Although it's an (SMC), we will continue to work closely with Pei Ling. She's been working hard here," he said.
MacPherson Citizens' Consultative Committee chairman Goh Khon Chong notes Ms Tin's dedication - she is still attending Meet-the-People sessions at her advanced stage of pregnancy.
As MP, she has introduced initiatives such as a fund to help elderly citizens with healthcare costs, a milk powder scheme for low-income families and learning activities for children with limited access to enrichment courses.
Residents say she is particularly popular with the older set. Says economics undergraduate Cheryl Law, 23: "She's quite active in visiting the old folks around here. My grandma thinks she's quite nice."
Nor does it seem that opposition parties will have an easy local hook for their campaign.
Municipal issues seem unlikely to feature, with even opposition supporters unable to name any.
Instead, residents note improvements: "We've been having quite a lot of upgrading projects here recently," says a 48-year-old semi-retired businessman who wants to be known only as Mr Han.
Retiree Koh Thong Guan, 60, appreciates new eldercare centres where he can drop by, while technician Salim Hussein, 48, points out a new playground and covered walkways, adding: "The atmosphere and ambience have improved."
The fight in MacPherson will be partly a referendum on how far Ms Tin has come since 2011. Says political watcher Eugene Tan: "It's a fantastic opportunity for her, and if she wins, it will be hard for the critics to continue with their attacks."