The Massachusetts Turnpike Authority’s latest offering of developable air-rights space at the intersection of Boylston Street and Massachusetts Avenue in Boston has some familiar faces jockeying for position.

At stake is 145,540 developable square feet, spread over four parcels spanning the Pike (Turnpike Parcels 12-15).

Proposals due Friday at noon show ADG Scotia LLC – a joint venture between Weiner Ventures and John Fish’s Suffolk Ventures – bid on three parcels (12, 14, 15) for housing, office and retail totaling 960,000 square feet; the Chiofaro Co. with Prudential Insurance Company of America bid on Parcels 14 and 15 for 636,000 square feet of office, parking and ground floor retail space; Trinity Financial put in for parcels 12 and 13 for just over 750,000 square feet of housing (546 units), retail and parking; while Carpenter & Co. wants parcels 14 and 15 for a 200-room hotel, 400,000 square feet in office space and a 500-car parking lot totaling 745,000 square feet.

Ahead Of The Pack

Adam Weiner’s group may have an inside track on the Pike parcels, thanks to a land acquisition this past spring. In May, ADG Scotia LLC purchased an 11,187-square-foot parcel from the Archdiocese of Boston for $13.85 million. The parcel, a vacant lot formerly belonging to St. Cecilia parish, abuts Parcels 14 and 15 and is seen as a staging ground that might be used to leverage more significant development.

Weiner’s father, Stephen, is the developer behind the Mandarin Oriental complex on Boylston Street, not far from the Turnpike parcels. ADG Scotia’s public filings with the Secretary of State’s office list Stephen Weiner as an officer.

The Weiner-Fish group has an incentive to be an active developer, rather than a group of investors looking to flip their parcel. A clause in the purchase agreement stipulates that if ADG Scotia sells the St. Cecilia parcel within five years of acquiring it, half of the resulting profit will revert back to the Archdiocese.

Chiofaro, the big-ticket developer behind International Place, acquired the Harbor Garage for $155 million last November.

Trinity Financial, developers of the $150 million Avenir mixed-use project in the Bulfinch Triangle, has been briefing neighborhood politicians and residents on its plans for a mixed-use project over the Pike for the past month.

Cambridge-based Carpenter & Co. is the team behind the Charles Hotel, the Liberty Hotel and Logan Airport’s Hilton.

Size Matters

Appropriate size is a hurdle any developer will have to clear, because it is difficult to squeeze profit out of an air rights development that may face serious massing constraints.

The BRA’s 1998 master plan for the area, commissioned in response to Millennium Partners failed 1 million-square-foot proposal for Parcel 12, envisions only one building topping 15 stories, with the rest topping out at 14 floors. Height would be set back, too, with street-front heights only reaching between 50 and 75 feet. The Neighborhood Association of the Back Bay has said it will be evaluating bids based on the parameters outlined in this plan.

State Rep. Marty Walz held up Millennium and Arthur Winn’s Columbus Center as cautionary examples any would-be Pike developers should avoid repeating. Both proposals were “grossly out of scale,” Walz said.

“Developers would be well advised to propose projects consistent with the neighborhood,” Walz warned. She also said state aid for the decking necessary to bridge the Turnpike may not be forthcoming, especially given the for-profit nature of any proposed development.