Annie Oakman, Real Estate

Annie Oakman, Real Estate Annie Oakman, Media Realty Group
Massachusetts & Connecticut Real Estate Agent & Real Estate Investor! I am a Real Estate Salesperson with Media Realty.

I specialize in buying, selling, renovations, and investments. I am an excellent listener and will work tirelessly on your behalf. My goal is to provide you with a positive experience, exceptional service and the highest level of professionalism. I will be with you from start to finish and will work to make your real estate experience enjoyable. I'm also a Real Estate Investor with my company, Flipping Millennials, LLC and would love to work with clients looking to purchase a fixer upper & guide them through that process.

Selling a home in Central Massachusetts this fall? Learn 4 strategies to attract buyers, price competitively, improve fi...
09/18/2026

Selling a home in Central Massachusetts this fall? Learn 4 strategies to attract buyers, price competitively, improve first impressions, negotiate confidently, and know when to adjust your listing strategy in today’s Worcester County and Middlesex County real estate market.

Selling a home in Central Massachusetts this fall? Learn 4 strategies to attract buyers, price competitively, improve first impressions, negotiate confidently, and know when to adjust your listing strategy in today’s Worcester County and Middlesex Coun...

Just Listed! 8 Glenmere Rd, Charlton, MA 4 beds, 2 baths, 2076 sq ft Large deck, formal dining room, and a walk in close...
09/18/2026

Just Listed! 8 Glenmere Rd, Charlton, MA

4 beds, 2 baths, 2076 sq ft

Large deck, formal dining room, and a walk in closet next to the primary that could easily be converted into a primary bathroom!

DM me “Charlton” for more information!

09/18/2026

I often get asked when I’m showing a property “Where does the sun rise and set?” This app gives you an amazing visual of how the sun and shade move across a property throughout the day.

It’s called ShadeMap, and it’s incredibly useful if sunlight matters to you when buying a home.

Share this with someone who’s house hunting & save it for when you’ll need it next! (It’s also helpful when deciding where to put your garden!)

If you’re looking to buy, sell, or invest in real estate, DM me “HOME”

Annie Oakman
Media Realty Group

7 Central Mass hikes worth doing this September 🍂Cooler air, no bugs, and the color is just starting to turn. Best hikin...
09/18/2026

7 Central Mass hikes worth doing this September 🍂

Cooler air, no bugs, and the color is just starting to turn. Best hiking month of the year!

📍 Gates Pond Loop, Berlin: easy 2.4 mile loop around the water. This is one of our favorites!
📍 Danforth Falls, Hudson: short 1.2 mile loop with a little waterfall. The kids LOVE this one, it’s one of their favorites!
📍 Mount Wachusett, Princeton: We typically do the Echo Lake Trail to High Meadows and then Jack Frost to the summit. Or if we need to switch it up or are limited on time, we’ll park at the visitor center and do the Pine Hill Trail up to the summit which is steeper but it’s the most direct trail so you get to the top quicker (typically!)
📍 Rock House Reservation, West Brookfield: a giant natural rock shelter kids can climb into, plus a great pond loop
📍 Doane’s Falls, Royalston: waterfalls right along the trail. Stay on the path, the rocks can be slippery here.
📍 Purgatory Chasm, Sutton: 70 foot granite walls, a rock scramble that kids love. Playground and bathrooms too, which is important when you have little ones! I won’t lie, this is my least favorite because the chasm gives me quite a bit of anxiety but typically we’ll start by going through the chasm and then will loop back around on the Chasm Loop Trail or Charley’s Loop Trail.
📍 Lookout Rock, Northbridge: quick climb, big Blackstone Valley view

All free to park at. Gates Pond is a drinking water supply, so no swimming there or at Doane’s Falls.

Save this for your fall weekends 🥾

Follow for hiking, biking, family fun, and all things Central Massachusetts!

Thinking about selling your home in Central Massachusetts this fall? About one third of annual home sales happen in the ...
09/15/2026

Thinking about selling your home in Central Massachusetts this fall? About one third of annual home sales happen in the final four months of the year. Learn why Worcester and Middlesex County sellers still have an opportunity to attract serious buyers before year end.

Thinking about selling your home in Central Massachusetts this fall? About one third of annual home sales happen in the final four months of the year. Learn why Worcester and Middlesex County sellers still have an opportunity to attract serious buyers ...

09/15/2026

Fall festival season is here in Central Mass 🍂

Here are 8 free (or low cost) events happening within about 45 minutes of Worcester this fall:

🍎 Hollis Hills Farm Apple Festival
🍺 Douglas Oktoberfest
🌾 Fall Fest at Wildwood Farm
🎉 Worcester Armenian Festival
🍏 Annual Apple Country Fair
🎃 West Boylston Fall Fest
🌽 Annual Sturbridge Harvest Festival
🍿 Annual Westminster Cracker Festival

Save this so you have it when the weekends roll around!

Follow for hiking, biking, family fun, and all things Central Massachusetts!

09/12/2026

9 hidden fall spots in Central MA that deserve a spot on your weekend list! 🍁

Think quiet trails, waterfalls, overlooks, old stone ruins, and gorgeous foliage without the crowds.

📍 From Berlin to Royalston, these are some of my favorite places to soak up fall in Central Massachusetts.

Save this for your next fall adventure! 🥾🍂

Which one are you checking out first?

Follow for hiking, biking, family fun, and all things Central Massachusetts!

09/11/2026

Worcester County’s average home value is now right around in the mid-to-high $500k’s. For a lot of first time buyers, that number ends the search before it starts.

But an average is just an average. Here’s where I’m suggesting my first time home buyers look right now:

📍 Sturbridge
📍 Charlton
📍 Auburn
📍 Millbury
📍 Lunenburg
📍 Worcester
📍 Leominster

Every one of these offers something a little different. A few are great if you commute. A few give you actual yard space. A couple have walkable centers and that neighborhood feel.

And some have homes that need work. That’s not a dealbreaker. I can walk a house with you and tell you the difference between “cosmetic and fixable”.

Save this for when you’re ready to start touring 👇 and comment the town you want me to break down first.

Wondering what you can actually afford, or whether you qualify for a Massachusetts first time buyer program? Send me a message. No pressure, just straight answers.

Follow for hiking, biking, family fun, and all things Central Massachusetts!

Data centers are becoming more common across the U.S. and could affect nearby homes, utility costs, and local developmen...
09/10/2026

Data centers are becoming more common across the U.S. and could affect nearby homes, utility costs, and local development. Here’s what Massachusetts home buyers and sellers should know about data centers and real estate values in Worcester County and beyond.

Data centers are becoming more common across the U.S. and could affect nearby homes, utility costs, and local development. Here’s what Massachusetts home buyers and sellers should know about data centers and real estate values in Worcester County and b...

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469 Southbridge Street
Auburn, MA
01501

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