FeaturedYonge-Eglinton · Toronto
69 Chaplin Crescent
$3,399,000
Real estate advice shaped since 2003
Serious decisions.
Clear direction.
Buying, selling or leasing, Anna Oliver brings direct advice, careful preparation and full concierge support to every stage of the move.
ExperienceSince 2003
ApproachFull concierge
WorkBuy · Sell · Lease
ReachCanada + international
Press & television
Seen, quoted & featured.
Selected property coverage, market commentary and on-screen appearances across Canadian and international media.
Publication marks identify the outlets in which Anna has appeared or been credited. Links open the most direct public source currently available.
Direct. Proactive. Client-focused.Toronto to Prince Edward County
Since 2003 in real estate
Halifax → Toronto market experience
Canada + international client support
Meet Anna
Experience matters most when it creates better decisions.
Anna began her real estate career in Halifax in 2003 and moved into the Toronto market in 2008. She built her practice through difficult markets by staying practical, proactive and close to the people relying on her.
Her work covers residential purchases and sales, leasing, investment and property strategy. Long-standing industry relationships also allow her to support clients across Canada and internationally.
The service is deliberately hands-on. Anna brings options before problems become emergencies, explains what the market is actually doing and remains involved after the paperwork is complete.
2003Career began in Halifax
2008Toronto practice established
RecognizedFeatured in national and real estate media
InternationalCanada + global client reach
Featured properties
Featured properties, clearly presented.
This is a curated snapshot of Anna’s featured listings. Availability, pricing and property details can change, so confirm the listing before relying on it.
Featured
FeaturedStreetsville · Mississauga
102 · 86 Joymar Drive
$759,000
High Park-Swansea · Toronto
88 South Kingsway
$10,000 / month
High Park-Swansea · Toronto
88 South Kingsway
$11,975 / month
North Marysburg · Prince Edward County
3246 County Road 8
$1,799,000
Picton · Prince Edward County
346 Picton Main Street
$3,390,000
Casa Loma · Toronto
209 · 380 Macpherson Avenue
$769,000
FeaturedThe Beaches · Toronto
20 Brookmount Road
$2,925,000
This is a curated listing snapshot and may change. Availability, measurements and pricing should be confirmed directly with the brokerage before relying on them.
Full service
Luxury service without the theatre.
Good service is not a performance. It is the quiet coordination of dozens of details before, during and after the transaction.
Anna’s approachPrepare carefully. Communicate clearly. Stay accountable.
Staging
Experienced interior stylists prepare each room so buyers can understand the home quickly and see how it could work for them.
Photography
Professional stills and property media are planned around the listing story, not treated as a box to tick before launch.
Digital marketing
Targeted distribution across social, search, video, agent networks, media contacts and an established client database.
Market intelligence
Comparable sales, neighbourhood context and current competition are translated into an actual decision.
Negotiation
Price matters. So do deposits, dates, inclusions, conditions and the risk inside a superficially attractive offer.
Logistics
Packers, movers, storage, painters, construction contacts, lawyers and the practical jobs that continue after the deal closes.
Your move
A clear plan for both sides of the transaction.
For sellersSelling with Anna
Hand us the keys. We will make the list shorter.
A strong sale comes from a series of sensible decisions made in the right order: value, timing, presentation, positioning, exposure, negotiation and a clean close.
- Understand the moveGoals, timing and a realistic view of value.
- Build the strategyPrice, competition, repairs and preparation.
- Prepare properlyTrades, styling, photography and final details.
- Take it to marketClear presentation and deliberate distribution.
- Negotiate, close and moveOffers, conditions, lawyers, packing and keys.
For buyersBuying with Anna
Find the right home. Keep your head while doing it.
Buying can be exciting and still require discipline. Anna helps separate the important detail from the noise, then negotiates from a position you can live with after the adrenaline wears off.
- PrepareBudget, mortgage options and practical requirements.
- Search intelligentlyTimely alerts, local knowledge and agent networks.
- Evaluate the propertyCondition, value, neighbourhood and future use.
- Offer and negotiatePrice, deposit, inclusions, dates and conditions.
- Close with fewer surprisesFinancing, inspection, legal work and handover.
Anna Oliver / Connected across Canada
Local knowledge. Connections that travel.
From a city address to a County home, start with the right local conversation. Moving further afield? Ask Anna about an introduction.
Property advice, rooted in local knowledge
Select a place to exploreCanada / Anna Oliver
Buying, selling & leasing
City moves, carefully handled.
Talk to Anna about buying, selling or leasing in Toronto, Mississauga and Oakville, or planning your next chapter in Prince Edward County.
The team
Clear roles. Shared standards. One team, clearly coordinated.
Anna leads the advice and client relationship. Ilja brings operational structure and precision. You know who is handling each part of the work and what happens next.
REALTOR® + Founder
Anna Oliver
Anna combines more than two decades of experience with a practical instinct for solving the problem before it becomes the client’s full-time job. Her approach is assertive, forward-looking and built around the person making the move.
- Service areas
- Toronto, Oakville, Mississauga and Prince Edward County
- Specialties
- Property management, development, appraising, retail leasing and apartment brokerage
REALTOR® + Director of Operations
Ilja Semikolennihs
With a Chemical Engineering background from Toronto Metropolitan University, Ilja brings structure, precision and a clear view of risk. He is candid when a client needs candour and methodical when the details get busy.
- Service areas
- Toronto, York, Simcoe, Niagara, Durham, Peel and Halton
- Specialties
- Resale, pre-construction, assignment sales, residential leasing and appraisals
Client experience
The transaction ends. The relationship does not.
Clients describe clear explanations, practical help, personal attention and a team that stays visible when the process gets tense.
Professional, private guidance, clear answers and the feeling that every concern was properly handled.
Downsizing into a condo closer to work and the life they wanted, with a smooth sale and a next home that felt right.
After an earlier listing failed, practical help created a route through the work the home needed and into a successful fresh start.
Personally supported through their home search, with their needs kept at the centre of each decision.
A planned downsizing became a clean sale, an ideal new place and far less friction than expected.
First-time sellers walked through the process in plain language, with a fast close and no mystery around the next step.
After an earlier attempt stalled, the family received practical help, a completed sale and a clean start in their next home.
Worked with Anna? Leave a review
Podcast + real estate digest
Real Conversations · Anna Oliver + Owen Ramirez
A new conversation about how real estate actually works.
Real Conversations is Anna Oliver and Owen Ramirez’s new podcast and real estate digest, with its own dedicated website.
Anna and Owen are recording conversations about Canadian housing, what agents are seeing on the ground, how brokerage is changing and the questions that deserve more than another headline. Episode 1 is now available on the podcast website.
Canadian housingAgent perspectiveCloud brokerage
Visit the podcast website
REALCONVERSATIONS
REAL with Anna Oliver
The business is working. Is the model keeping up?
Anna’s agent resource centre puts cloud brokerage, costs, fit and transition planning into plain language—with calculators that show the result before asking for your email.
Explore REAL with Anna Useful tools
Start with the numbers. Then have the real conversation.
Use the compact calculator here, open the full Mortgage Payment Planner or request a comparative market analysis. These are planning tools, not substitutes for qualified advice.
Mortgage Payment PlannerEstimate
A quick payment estimate.
Estimated monthly payment$4,428Based on an $800,000 mortgage
Open the full planner with closing costs
Planning estimate only. Taxes, insurance, fees and mortgage insurance are not included. Confirm lending terms with a qualified mortgage professional.
Home evaluationPersonal review
What might your home be worth?
Anna will prepare a comparative market analysis using relevant recent sales, current competition and the details that make your property different.
Latest activity
Recent listings, viewings and completed sales.
A focused view of recent open houses, newly listed properties and completed results.
69 Chaplin Crescent
Five-bedroom detached home on a 45 by 120 foot south-facing lot in Yonge-Eglinton, with a heated saltwater pool and Davisville Station close by.
69 Chaplin Crescent
A second weekend viewing for the same Midtown property, with Oriole Park, the Beltline and Yonge-Eglinton within easy reach.
102 · 86 Joymar Drive
Furnished three-bedroom Streetsville townhome near the GO station, schools and village shops, with an unfinished basement ready for future use.
4603 · 2191 Yonge Street
A high-floor Midtown residence with panoramic southeast views, one bedroom plus den, parking and a locker has completed its sale.
2101S · 127 Broadway Avenue
A meticulously maintained residence at Line 5 Condos has completed its sale in Midtown Toronto.
102 · 86 Joymar Drive
The Streetsville townhome joined the market furnished, offering a practical option for first-time buyers and investors.
Start here
A big decision deserves a proper first conversation.
Tell Anna what you are considering, what feels unclear and what kind of timing you are working with. You do not need a perfect brief.
Call416-206-9867
Emailanna@annaoliver.ca
Office130 King Street West, Suite 1900
Toronto, Ontario M5X 1E3
Toronto, Ontario M5X 1E3
Tell us what you are working through.Anna’s team will respond directly.
Occasional updates
Useful property notes. Not daily inbox furniture.
Market context, new listings and the conversations worth keeping up with.