Oldstreet | Calgary Real Estate Development


Oldstreet is a company with boundless energy and ideas. We bring passion and a fresh approach to everything we do. Our time horizon is long. Our journey has just begun.

Parc on 30th | Boutique NYC-styled brick residences set on leafy South Calgary Park.
Featured in Avenue Magazine
  • No cookie cutters.
  • No chasing trends.

Founded in 2018, Oldstreet was borne out of a desire to build better – better homes, better communities and a better Calgary.

Stylish projects, each one unique. No cookie cutters, and no chasing trends leaving homes and communities feeling dated and listless. We create buildings that hold their value while enhancing and reinforcing community character.

We bring much needed quality housing stock to inner city communities, contributing to more dense, thriving communities – communities that we ourselves, and our kids, and their kids, will want to live in.

Oldstreet | Calgary Real Estate Development

With each development we ask ourselves “does this look great now and will this look great 10, 20, 50 years from now? Does this create a more beautiful, vibrant and livable community? Is this a home we would want to live in ourselves?” These questions guide our every decision throughout the creative process.

Oldstreet | Building the Calgary of the Future
Oldstreet | Building the Calgary of the Future
Oldstreet | Building the Calgary of the Future

Fellow Calgarians: Let’s build the best city in the world. Let’s build a global city that is beautiful, vibrant and sustainable. Let’s build the Calgary of the future!

Oldstreet | Building the Calgary of the Future
Oldstreet | Building the Calgary of the Future
Oldstreet | Building the Calgary of the Future
Oldstreet | Building the Calgary of the Future

“Be the change you want to see in the world”.

Our Team

Nathan Robb, Co-Founder, Principal

Nate has a keen interest in real estate, architecture and design and those interests, combined with an entrepreneurial spirit, led to the founding of Oldstreet. Nate has over 15 years experience in the real estate sector, beginning with summer work in various trades and then as legal counsel, investor and company founder.

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Nate previously practiced corporate, securities and M&A law in Calgary and London, UK (where the Oldstreet vision and name was born!), completing 100+ transactions with combined deal values in the billions of dollars, and worked in finance roles in Mumbai and Hong Kong. Opportunities to live, work and travel abroad in global cities and among diverse cultures is an ongoing source of inspiration for Nate and his family. It motivates him to create vibrancy and progressive change in his home city of Calgary and to develop real estate in interesting global locations. Nate obtained his law degree from the University of Alberta and his Bachelor of Management (Finance) degree from the University of Lethbridge.

Connor Irving, Co-Founder, Principal

Connor has always aspired to be an entrepreneur and find opportunities to drive change, add value and improve the world in some way. The opportunity to create, innovate and build a distinctive brand and business is something that is truly unique and led him to founding Oldstreet. Connor grew up in Calgary and is proud to call the city home.
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He has enjoyed watching it grow into a vibrant, active and diverse city and is excited to help shape its communities and neighbourhoods through Oldstreet. Prior to Oldstreet Connor spent a decade in the finance and banking industry, most recently with Bank of Montreal in their mid-market private equity leverage finance group. He was a Senior Director focused on building relationships with Private Equity groups across the Prairies and US and assisted in structuring new deals across a wide range of sectors from real estate, manufacturing, health sciences and energy, and managed a portfolio of loan authorizations of over $600MM. During his time with Bank of Montreal Connor worked on 100+ transactions totaling over $5 billion dollars in loan value. Outside of work, Connor loves spending time with his family which includes his wife, Meghan, their son, Griffin, their first daughter, Tia, and their newest baby girl, Andie. In the moments between work and family, Connor finds time to run, having completed several marathons and ultra-marathons, and whenever there’s a chance, being a die-hard sports fan, he cheers on his favorite teams, the Toronto Blue Jays and Dallas Cowboys. Connor has an MBA with honors from the Ivey Business School.

Jon Turton, Construction Operations Manager

Jon brings 25+ years experience in residential construction to Oldstreet. He started his career as a site labourer and draftsman, working his way up to warranty and construction management with some of Western Canada’s largest homebuilders undertaking programs ranging from 130 to 450 homes per year. Jon enjoys an active outdoors family life with his wife, two boys and dog Max.
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Jon studied Pre-Engineering and Architectural Technology at NAIT while also maintaining studies in Building Sciences, Energy Efficiency, Net Zero initiatives, Customer Service and Safety.

Miles Kortje P. Eng., Project Manager

Miles brings 25+ years experience in all aspects of construction project management to Oldstreet. He has successfully led projects ranging from large custom single-family homes to, most recently, multi-family projects ranging from 230 to 400+ units with project values of up to $70 million. Miles has an active family and enjoys playing hockey, golf and baseball.
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Miles obtained his Bachelor of Science degree in Civil Engineering from the University of Saskatchewan and is a lifetime member of the Association of Professional Engineers and Geoscientists of Alberta (APEGA).

Our Inspiration

We have spent time exploring iconic neighbourhoods in global cities such as London’s Chelsea, Manhattan’s Greenwich Village, Brooklyn’s Park Slope and Boston’s Beacon Hill (we suggest you do the same!). We love the density, walkability, access to local amenities, diversity and character in these communities. We are inspired by the timeless and dramatic brownstones and other low and medium density housing options in these neighbourhoods and the lifestyle they afford their residents. In fact, Oldstreet is named after a tube station in London!

Oldstreet Development | Inspiration

We constantly seek new and interesting global destinations for travel – we draw inspiration from unique cultures, weather, lifestyles, art, architecture, design, cuisine and much more. We have been moved to action by the Pura Vida lifestyle in Costa Rica (a great place to beat Canadian winters!) and are excited to grow our presence throughout the country and in other unique and interesting global destinations in the future.

Oldstreet | Calgary Real Estate Development

Our Promise

We promise to use the highest quality standards of design and construction. We will build every home as if it was our own. We will respect and enhance neighbourhood character and vitality and build upon existing heritage and cultural identity. We will foster efficient use of land, helping to create complete communities that offer a greater variety of housing choices. We will help rejuvenate communities and create a better quality of life for residents and guests – the elderly living next to young families, school yards full of activity, bustling coffee shops and local business thriving.

This is our promise and our commitment to our customers, our neighbours and the communities we are in.

Oldstreet | Calgary Real Estate Development

Frequently Asked Questions


Will you sell us a home before it is complete?
Yes! We “presell” many of our homes. Buyers get to secure their home before it goes to someone else. Also, we often work with presale buyers to customize certain details to their liking.
Do you have any projects coming that are not listed on your website?
We have a lot of fun stuff in the works! Our projects are long-lead, and we are typically working on them long before they become public knowledge. Please reach out. If we know what you are looking for, we can do our best to make something work.
Do you offer a warranty on your homes?
Yes! Oldstreet is a licensed developer and is pleased to provide homebuyers with a comprehensive warranty through the Alberta New Home Warranty Program. In summary, this includes warranty of 1 year on labour & materials (e.g. baseboards, flooring and fixtures), 2 years on distribution systems (e.g. heating, electrical and plumbing), 5 years on building envelope (e.g. roof and exterior walls) and 10 years on structural (e.g. frame and foundation).
Will you build me a custom home?
We are a small and focused company. Our main business is not custom homebuilding; however, we are architecture and design obsessed and love an opportunity to build unique and stylish homes. We consider custom projects on an induvial basis – please reach out if you think we could be a fit.


Do you pay realtor commissions on land or homes not listed on MLS?
Absolutely. Realtors offer tremendous value, and we are happy to pay for their services. Please reach out to discuss fees with us – we always work out a good and fair deal for all parties involved.


Why is Oldstreet now building rentals?

As Canada’s population grows and home prices continue to outpace incomes in many parts of the country, the demand for rental housing continues to grow. We want to do our part in keeping housing affordable and accessible for more people (especially in Calgary, where our relative affordability has been a good competitive advantage!).

Also, we think renting is cool – you can save money to get ahead, allocate more spending to travel, friends and family and live more flexibly, trying out different housing types, neighbourhoods and cities.

Why rent an Oldstreet home?
A lot of rental housing stock is dated and non-descript. It doesn’t have to be this way. We are excited to build stylish, high-quality rental homes that you can be proud of.


I own land that I think has development potential. Are you interested in buying it?
Yes! Landowners regularly get in touch with us if they are looking to sell their land privately or without realtor involvement. Please reach out – we are happy to chat.
I own land that I think has development potential. Are you interested in partnering or joint venturing with me?
Yes! We are open to creative arrangements that could lead to a win-win for both parties. Please reach out and we can discuss your vision and see if we can make something work.