Why Maitland (Winter Park/Orlando) is such a great place to live!!

Services for Real Estate Pros with John Henry Masterworks Design International, Inc. 13013

Yup, that's me above.  At the Pig Floyd's restaurant on a Saturday afternoon -- about 2 o'clock -- photo was sent to my relatives who decided to move to the hills of North Carolina and were posting sub-freezing temperatures and rain for several days in January.


This winter we have turned on our electric heat for only 2 hours to date.  

Let me count the ways I love Maitland, Florida and why we have been living in the Orlando area for the last 30 plus years!

Maitland has only about 18,000 people living here, but it is Central Florida's best-kept secret.  It has a small-town feel but a large town reach.  See new condo complex below right.

  1. BUSINESS  The pull to Central Florida for me was a steadily increasing economy.  Not a boom or bust from where I escaped.  In the mid-80s Florida was bringing in retirees from the north with pockets full of cash (from the houses they just sold) and would do drive-bys and point to the new house they wanted to buy. They really didn't want to spend any time designing new houses.  Speculative construction was booming as builders built as fast or faster than they sold.  Banks were lending money hand over fist.  Things have slowed down a bit since the last national recession but business in leisure and related industries is very strong.  For me, several clients fly in to enjoy the fun and sun and will visit my office to have a house designed.  
  2. LOCATION  Maitland is located in the middle of the state of Florida, just north of downtown Orlando and adjacent to Winter Park and Altamonte Springs.  In under two hours you can drive to either the Gulf of Mexico or enjoy the Atlantic coast.  In four hours you can visit Miami; in eight you can be in Atlanta or settled into your hotel room in the Keys.  We are 45 minutes from an international airport with direct flights to Europe.  Very convenient..
    Maitland itself is 30 minutes from Universal Studios, Seaworld and Disney attractions.  It takes 4 minutes from our house to get to the Interstate and downtown to national sports events to opera in 9 minutes. 
  3. It's just super.  DAY TO DAY LIVING: Wow, it's amazingly great!  We can be at any mall, bank, food store, restaurant we like, 7-11, movie theater, park, funeral home, church, hospital, etc. within a 6 to 10-minute drive.  We are in a subdivision of older homes, on a lake, heavy oaks, and can go north/south/east/west without any problems.  The neighborhood is quiet and walking the doggies very easy while taking photos of the changing seasons and flora.  There are over 5 parks with walking trails, lakes, children's playgrounds, etc. within that 10 minutes.  The sheer convenience of day to day living is the number one thing.  
  4. FUN THINGS TO DO  Fish and boat on local lakes or deep water, attend art museums, golf on numerous courses at public and private clubs, attend NBA or baseball games, spend days at Universal Studios and Disney, jog and walk at nice neighborhood parks, drive to the beach and come back in one day, lots of restaurants and movies, have bbqs by the pool, stay casual nearly all year long, feel alive!  Drive east for an hour and feel the thunder of a rocket launch from the Cape.  While in the area stop in for an airboat ride!  Drive 25 minutes north to Sanford and rent a float boat to navigate the clear waters of the St. John River. Florida is for outdoor folks who enjoy water, sun, sports, and sightseeing. A nearby freshwater spring and park, Wekiva, takes you back to primitive days as you swim in clear water as the Seminoles and canoe the tributaries watching 'gators glide underneath. My favorite haunt: Winter Park's Park Avenue on which numerous tasty restaurants and boutique shops lure you in.  It is the closest thing to being in France or Italy.  The outdoor cafes are fabulous.  Friends + food = fun.  Don't miss the Winter Park Scenic boat tour, and ask for Alan Woods!  Culture? The only museum featuring the work of Louis Comfort Tiffany is at 445 N. Park Ave.  There is an intact altar from the 1893 World's Fair. A 45-minute drive northwest lands you in beautiful Mt. Dora, on a large chain of lakes. Oh yes, we have a Film Festival sponsored by the Enzian theater and a Fringe Fest, which features very creative types.  There are jazz and blues clubs to boot! Oh, the second largest Ferris wheel in the U.S. is on International Drive.  The strip also has a Ripley's and other adventure rides.  What else?  I have never seen so many restaurants per square mile as in the Tampa area!  My favorite is Mykonos in Tarpon Springs.  Tell Andy I sent you.  Amazing homemade Greek delicacies.  While there take a tour on the sponge diving boat and another to take you out to the Gulf and watch manatees and dolphin frolic.  Almost forgot: DAYTONA 500!  And Bike Week for cycle lovers!
  5. WEATHER Most of the fun things above are possible by nearly perfect weather all year round.  Yes, it rains and we see a hurricane or two a year or every two to three years.  The winter is so easy to take.  Fine weather starts in November and goes through mid-April until things just start heating up.  There is heat and humidity for a good three to five months but is not overbearing for more than 3 or 4 weeks.  Flip flops, t-shirts, and shorts are the look of summer and through most of the year in fact.  Today, March 2, 2020, we have a high of 77 degrees.  Gorgeous.  Oh yes... 'gators love to come out in the cold weather and sun on the shores of the lakes.  Boat tours in Mt. Dora and The Villages take you through beautiful pristine waters so that you can watch them in their natural habitat...  
  6. HOUSING  Orlando is in the “Top 10 best cities for first-time homebuyers.”  Appreciation last year was 6%.  Median rents are at $1,599 per month.  The median price of homes currently for sale in Orlando is $289,000. You can move to Central Florida with little money and rent a house or apartment easily as you move up in your career and expand your contacts.  There are multiple luxury gated golf communities for the high-end buyer (Isleworth, Lake Nona, Alaqua, Golden Oaks) and a wide mix of housing below that.  Condos have sprung up to get you closer to the concentrated fun described above.  Mid-level prices are still very good and appreciation is quite nice.  There is a lot of construction activity at this time and remodeling seems to be strong. (Transitional style house above designed by John Henry Architect, Builder is Charles Clayton Construction).
  7. EMPLOYMENT  Florida enjoys an unemployment rate of 3.2%~! The Orlando metro area is at an astounding 2.8%! -- the tenth lowest in the country.  Business is churning, people are working, and fortunes are being made.  This is the lowest rate in over 8 years and well below the 3.6% national average.  Florida attracts 900 people a DAY.  This should be good news for anyone related to the housing and food industries and all support businesses in between.  Another statistic: there is a 34% deficit of houses for sale.
  8. YOU CAN HAVE IT ALL  No doubt, living in Central Florida is a 'best of all worlds' adventure!  So many things to do, so much bright sun and outdoor living.  From children's activities to adult living, there are a myriad of choices available.  Maitland is a hidden gem and still priced right.  You are in secluded tree-lined streets and feel small town but in 6-8 minutes you can get just about anything you want.  Florida has zero income tax to boot!  If you come by on a Saturday, I will give you a tour.  Wear flip flops, a t-shirt, and shorts!  Let's meet at the Croissant Gourmet in Winter Park for boutique coffee and some of the best French pastries available in Florida!  If you miss me, ask for Francois; he will treat you right. Doesn't this look like the European riviera below?
  9. TOURISTS  (If you can't manage a trip to Italy right now, stay at the Universal Studios Portofino Hotel, above, and with just a little squint -- you're there!)  The Orlando theme parks drew over 75 million visitors in 2018!!  That is a 5% increase over the year before.  You would think that living here would be a true jungle with so many people running around.  Well, the nice thing about Maitland is that NO ONE drives through this area unless they live close by.  Maitland is about 20 miles away from Universal Studios,  Sea World and Disney attractions.  You can freely move about and rarely bump into a tourist.  The amazing resort hotels, discount malls, and attractions centered in the southwest part of the metro area keep all these people in that zone.  So if you want a year-round Florida pass to any of the parks, you can pick the best times to go and to stay away when packed and too hot! 
  10. ARCHITECTS  Why, you only have to contact me to have nearly anything you have in mind designed!  There are a lot of close-in properties that are ready for a teardown start from scratch custom design or great remodel.  We do both and are well known in the area.  For over thirty years I have been creating inspiring  and practical custom homes for Central Florida in Maitland, Winter Park, and the Orlando and Windermere area.  We have won multiple local and regional awards.  We are doing historical projects and custom homes from 2,800 SF to 28,000 SF here and out of state.  Let me know if you have any questions about the area and where you would like to live.  I can also put you in touch with several great Realtors.  Here is a link to start now with any design that you have in mind.  I am here to help make your vision a reality. (Craftsman style home above, Palm Beach mansion below)

This post is part of the The Perks of Living in My Community – March 2020 ActiveRain Challenge


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Kathy Streib
Room Service Home Staging - Delray Beach, FL
Home Stager - Palm Beach County,FL -561-914-6224

Hi John- I loved living in Maitland, and yes, Park Avenue in Winter Park was one of my favorite places to be on a Saturday or even Friday date night. 

Mar 02, 2020 07:39 PM #1
James Dray
Fathom Realty - Bentonville, AR
Exceptional Agents, Outstanding Results

Morning John.

So, by your post I take it you love living in Maitland.  Just a wild guess on my part.  LOL

Mar 03, 2020 01:27 AM #2
Michael Jacobs
Pasadena, CA
Los Angeles Pasadena 818.516.4393

Hello John -  you do make  Maitland sound like a year-round vacation spot.  And vacationing while at home is a nice incentive.  

Mar 03, 2020 03:11 AM #3
John Henry, Florida Architect
John Henry Masterworks Design International, Inc. - Orlando, FL
Residential Architect, Luxury Custom Home Design

Hi Kathy Streib   I forgot you also lived in Maitland!  We are in the Druid area, the farthest west in Maitland.  I find so many advantages here that I have just stayed plum put!  Winter Park is charming and without it, things wouldn't be the same.

Hey there James Dray   I just starting counting the ways... I received a call from the Chamber of Commerce just a few minutes ago!!!

Yes, Michael Jacobs  It is exactly that, yet out of the way!  And the vacationing at home is great...just have to force yourself to get back to work!!!


Mar 03, 2020 04:39 AM #4
Wayne Martin
Wayne M Martin - Chicago, IL
Real Estate Broker - Retired

Good morning John. Hard to argue with living in Florida. Certainly liked it for 26 years until family called us back to Chicago. Enjoy your day!

Mar 03, 2020 05:18 AM #5
Jeff Dowler, CRS
eXp Realty of California, Inc. - Carlsbad, CA
The Southern California Relocation Dude

Hi John:

Wow, this is wonderful! You are the ambassador for Maitland for sure - what a wealth of information and all that anyone need to know. And your photos bring the community to life!! Thank you for sharing your community with us!


Mar 03, 2020 07:53 AM #6
John Henry, Florida Architect
John Henry Masterworks Design International, Inc. - Orlando, FL
Residential Architect, Luxury Custom Home Design

Hi Wayne Martin   I really enjoyed the sights in Chicago, what a great place!  We went on two of the Wright tours.  So much real history and culture.  Come back here for a few days of warm weather!  Thank you.

Hello Jeff Dowler, CRS   I am a big fish in a small pond!!  Only 18,000 of us here at most.  It's just that the location is so good and things absolutely so convenient it hurts!  Appreciate the opportunity to crow a bit and thanks for the great idea for the challenge.

Mar 03, 2020 07:57 AM #7
Grant Schneider
Performance Development Strategies - Armonk, NY
Your Coach Helping You Create Successful Outcomes

Good afternoon John Henry, Florida Architect - no arguement here.  I love my home in Florida and love the lifestyle.

Mar 03, 2020 10:25 AM #8
Ron and Alexandra Seigel
Napa Consultants - Carpinteria, CA
Luxury Real Estate Branding, Marketing & Strategy


What an enticing description of Maitland, and we are delighted that you love living there as well as all the amenities that you have.  Enjoy.  A

Mar 03, 2020 12:38 PM #9
John Henry, Florida Architect
John Henry Masterworks Design International, Inc. - Orlando, FL
Residential Architect, Luxury Custom Home Design

Hi Alexandra: Sunny, convenient to so much.  Thanks Ron and Alexandra Seigel 

Mar 04, 2020 08:32 AM #10
Melinda (Mel) Peterson
Grants Pass, OR - Bend, OR
The Blessed Realtor - ABR, CRS

Awesome post about your small-town community with huge appeal!  I had to laugh out loud on this part... We can be at any mall, bank, food store, restaurant we like, 7-11, movie theater, park, funeral home, church, hospital, etc. within a 6-10 minute drive.  

Mar 04, 2020 10:26 AM #11
Lawrence "Larry" & Sheila Agranoff. Cell: 631-805-4400
The Top Team @ Charles Rutenberg Realty 255 Executive Dr, Plainview NY 11803 - Plainview, NY
Long Island Home and Condo Specialists

This is a very nice introduction to life in Maitland. It's a town I was not familiar with and looks lovely!

Mar 04, 2020 10:38 AM #12
John Henry, Florida Architect
John Henry Masterworks Design International, Inc. - Orlando, FL
Residential Architect, Luxury Custom Home Design

Hi Melinda (Mel) Peterson YES: we are womb to tomb here!!!  It is crazy but there is one arterial that HAS IT ALL.  Including a funeral parlor, dog vet, autobody shop, Turkish restaurant, and dozens of other shops and offices.  I thought someone would get a kick out of that.  THANKS!!!

Hello Lawrence "Larry" & Sheila Agranoff. Cell: 631-805-4400   Well, it's not Long Island and New York but it offers a heck of a lot to do in this location!  Thanks very much.

Mar 04, 2020 10:46 AM #13
Patricia Feager, MBA, CRS, GRI,MRP
Selling Homes Changing Lives

John Henry, Florida Architect - You crack me up! That first photo of you was not expected but then when I read about the relatives who decided to move to the "hills of North Carolina posting sub-freezing temperatures and rain in January," I couldn't stop laughing!

Prospective Buyers and Sellers not only get someone who is very comfortable in his own skin, but extremely knowledgeable about the area, what FL has to offer, great Architecture, the building process, and Designing Luxury Custom Homes. 

John, your photos always speak to me and your content is always in depth with wisdom. Your expertise is phenomenal. You have a mind like no other. 

Buyers and Sellers will be pleased when they hire you.  

Mar 05, 2020 08:12 AM #14
John Henry, Florida Architect
John Henry Masterworks Design International, Inc. - Orlando, FL
Residential Architect, Luxury Custom Home Design

Hi Patricia Feager, MBA, CRS, GRI,MRP   Great to hear from you!  Yes, the opening line is a continual dig aimed at my silly relatives who moved to a cabin in the middle of nowhere and didn't read the weather charts which indicate rain half the year and sub-freezing temperatures throughout the winter.  I dig in hard on them.  They even block my texts.  HA!!  Yes, here for perhaps too long.  The summer can wear a bit.  I used to live in Houston; I think this is less humid.  Austin was great. Dallas has to be dryer.  I took a few of those photos, thanks.  I only report the facts. I don't make them up.  I do appreciate your always kind assessment.  Hope all is well!

Mar 05, 2020 12:50 PM #15
Debb Janes EcoBroker and Bernie Stea JD
ViewHomes of Clark County - Nature As Neighbors - Camas, WA
REALTORS® in Clark County, WA

Okay, womb to tomb is a new one for me. Lol, lol, lol. Let me just say, your first photo had me sold. Nice job, John. 

Mar 05, 2020 01:25 PM #16
Raymond Henson, SRES, GRI
eXp Realty of California, Inc. (lic. #01878277) - Elk Grove, CA

We have been close to your area several times over the last few years and have not heard of Maitland.  It is a best kept secret.  I think I want to try one of those crepes.  Next time we visit, we better get in touch. 

Mar 28, 2020 03:32 PM #17
John Henry, Florida Architect
John Henry Masterworks Design International, Inc. - Orlando, FL
Residential Architect, Luxury Custom Home Design

Hello Raymond, this is really a small town sandwiched between Winter Park and Altamonte Springs.  It's about location most of all.  SO convenient to everything and taxes much lower than Winter Park.  The crepes at Croissant Gourmet are very very good.  Hope to see you next time you come into town!
Thanks, Raymond Henson, SRES, GRI 

Mar 29, 2020 12:42 PM #18
Debe Maxwell, CRS
www.iCharlotteHomes.com | The Maxwell House Group | RE/MAX Executive | (704) 491-3310 - Charlotte, NC
The right Charlotte REALTOR!

Oh my gosh - first I was mesmerized by the slideshow (and figuring out how you did that!) and then reading all that you have there - OH MY! I'm nearly convinced to move there, John! 

And, I had to laugh about your relatives who moved to the mountains of NC. I much prefer the foothills where we live!

Thank you so much for sharing so much great information about Maitland/Winter Park/Orlando, FL, John. What a wonderful entry in this month's challenge!

Mar 31, 2020 10:36 PM #19
John Henry, Florida Architect
John Henry Masterworks Design International, Inc. - Orlando, FL
Residential Architect, Luxury Custom Home Design

Hi, Debe Maxwell, CRS   I am glad you got a chuckle out of that!  My relatives live in western NC in Andrews.  They are on lockdown and the sheriff is stopping all car coming through!  Here is what I did this morning in Winter Park: https://activerain.com/blogsview/5484007/how-one-architect-in-winter-park-is-dealing-with-the-current-economic-slowdown

Apr 01, 2020 11:45 AM #20
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