Rob Sassos -Broker/President

Rob Sassos

Phone: 407.982.4456
Fax: 407.386.6136

Simplicity: A Real Estate Brokerage Company

960 Aragon Avenue Winter Park, FL 32789

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Broker/President

A Desire to Achieve and Serve

Rob has been actively selling real estate since 2009, but his commitment to building and maintaining professional relationships spans over thirty years. With a diverse background in real estate, banking, technology, and law, Rob prioritizes the customer experience, always striving to exceed client expectations.

A University of Central Florida graduate and former college athlete, Rob has lived in the Orlando area for over twenty-five years and currently resides in Winter Park with his wife, Shannon, and their fur baby, Savannah.

Rob and Shannon own a successful wine and cigar lounge in downtown Winter Park called Morse Code. An avid soccer and martial arts enthusiast, Rob supports Orlando City and Tottenham Hotspur and regularly trains in Brazilian Jiu-Jitsu, holding a brown belt.

As a professional Realtor, Rob is an active Real Estate Broker dedicated to giving back to his profession and community. He is a member of the Orlando Regional Realtors Association (ORRA) and serves on the Community Relations and Government Affairs committees.

Rob is also highly active on social media. His Facebook Live show, Java Jabber, has garnered a large following, covering a wide range of topics with a real estate twist. New episodes air every Tuesday and Thursday.

A consistent multi-million dollar producer, Rob leverages cutting-edge technology, extensive knowledge of the Metro-Orlando and Winter Park real estate market, and insights into the latest trends in Central Florida to provide his clients with a competitive advantage and powerful advocacy.

Some of My Favorite Properties

347 Agnes Street, Orlando — 347 $665,000

Rarely on the market - This fabulous 2 bedroom, 2.5 bath townhome is located just south of downtown Orlando in the historic district of Lake Cherokee. PLANTATION OAKS of...

2 Beds
2.5 Baths
Plantation Oaks SubDv.
32801 Zip Code

322 E Central Boulevard Unit 901, Orlando image

322 E Central Boulevard Unit 901, Orlando — Waverly/Lk Eola $1,000,000

Discover this penthouse-style condominium featuring breathtaking panoramic views of Lake Eola and the stunning Orlando skyline—truly an iconic sight for the city. This is...

3 Beds
2 Baths
Waverly/Lk Eola SubDv.
32801 Zip Code

901 E Pine Street Unit 2, Orlando — Beth Kelly $777,000

Rare opportunity to own a piece of Orlando history! Formerly home to the Bethea Ebsen Dance Theater, where Jed Clampett of “The Beverly Hillbillies’ lived, this charming ...

3 Beds
2.5 Baths
Bethea Ebsen Condo Or 6377 5415 SubDv.
32801 Zip Code

150 E Robinson Street Unit 1401, Orlando image

150 E Robinson Street Unit 1401, Orlando — Vue At Lake Eola $549,000

Experience premier high-rise living in the heart of downtown Orlando with this unique 2-story loft-style condo, offering breathtaking, panoramic views of Lake Eola and th...

1 Beds
1.5 Baths
Vue/Lk Eola SubDv.
32801 Zip Code

150 E Robinson Street Unit 1907, Orlando image

150 E Robinson Street Unit 1907, Orlando — Vue $600,000

Enjoy luxury living at its finest at The VUE at Lake Eola, located in the heart of downtown Orlando. This LAKESIDE unit offers breathtaking views of Lake Eola, right from...

2 Beds
2 Baths
Vue/Lk Eola SubDv.
32801 Zip Code

150 E Robinson Street Unit 2211, Orlando image

150 E Robinson Street Unit 2211, Orlando — The Vue $649,990

LIVE INSPIRED in this BEAUTIFUL 2 Bedroom / 2 Bathroom CORNER UNIT with FLOOR to CEILING WINDOWS on the 22nd FLOOR of Orlando’s TALLEST RESIDENTIAL BUILDING, The VUE! The...

2 Beds
2 Baths
Vue/Lk Eola SubDv.
32801 Zip Code

150 E Robinson Street Unit 1711, Orlando image

150 E Robinson Street Unit 1711, Orlando — The Vue At Lake Eola $639,000 ▼

Discover the epitome of urban luxury in this immaculate 2-bedroom, 2-bathroom corner unit, perfectly situated on the 17th floor of The Vue at Lake Eola. Spanning 1,445 sq...

2 Beds
2 Baths
Vue/Lk Eola SubDv.
32801 Zip Code

150 E Robinson Street Unit 3405, Orlando image

150 E Robinson Street Unit 3405, Orlando — The Vue $599,990 ▼

Huge Price Drop!! Come get it!! Best Views in Orlando Welcome to a Realm of Sophistication and Modern Luxury!! Discover unparalleled grandeur and elegance in the heart ...

2 Beds
2 Baths
Vue/Lk Eola SubDv.
32801 Zip Code

1911 Park Lake Street, Orlando — 1 $599,990 ▼

Welcome to Colonial Town! This new rear unit 3-bedroom, 2.5-bathroom townhome is completed and awaiting it's new owner! More photos to come!! Featuring a light and brigh...

3 Beds
2.5 Baths
Aa Morey"S Sub SubDv.
32803 Zip Code

2179 E South Street Unit 3, Orlando image

2179 E South Street Unit 3, Orlando — Townes At Vdara $657,990

Pre-Construction. To be built. Nestled in Orange County, Orlando's Vdara community offers residents the ideal fusion of metropolitan accessibility and suburban serenity. ...

4 Beds
3.5 Baths
Vdara Ph 2 SubDv.
32803 Zip Code

2183 E South Street Unit 2, Orlando image

2183 E South Street Unit 2, Orlando — Townes At Vdara $599,990 ▼

Pre-Construction. To be built. Nestled in Orange County, Orlando's Vdara community offers residents the ideal fusion of metropolitan accessibility and suburban serenity. ...

4 Beds
3.5 Baths
Vdara Ph 2 SubDv.
32803 Zip Code

260 S Osceola Avenue Unit 907, Orlando image

260 S Osceola Avenue Unit 907, Orlando — Star Tower Condominium $620,000

How would you like to live in pure Luxury in the heart of Downtown Orlando??? Welcome to the Modern elegance of the Star Tower downtown Orlando condominium! This Gorgeo...

2 Beds
2 Baths
Star Tower Condo SubDv.
32801 Zip Code

117 E Concord Street Unit 8, Orlando image

117 E Concord Street Unit 8, Orlando — 117 $570,000 ▼

Downtown Orlando luxury living at its finest! The front invites you in with the gated walkway welcoming you to this picturesque palace! The open and spacious floor plan...

3 Beds
3.5 Baths
Lake Eola Heights SubDv.
32801 Zip Code

530 E Central Boulevard Unit 1901, Orlando image

530 E Central Boulevard Unit 1901, Orlando — 530 $1,295,000 ▼

Welcome to your new home in the heart of downtown Orlando! This exquisite 3 bedroom 2 bathroom luxury penthouse offers an unparalleled living experience with its impeccab...

3 Beds
2 Baths
530 East Central Condo SubDv.
32801 Zip Code

150 E Robinson Street Unit 1709, Orlando image

150 E Robinson Street Unit 1709, Orlando — The Vue At Lake Eola $599,900 ▼

Welcome to The VUE at Lake Eola, an exquisite high-rise residence situated in the dynamic heart of Downtown Orlando. This unique, larger 2-bedroom, 2-bathroom condo—a rar...

2 Beds
2 Baths
Vue/Lk Eola SubDv.
32801 Zip Code

337 Cathcart Ave Unit 6, Orlando — Casa Eola $600,000 ▼

PRICE IMPROVEMENT!! CHARMING 3 BEDROOM/3.5 BATH CONDO in the Heart of Downtown Orlando, just two blocks from Beautiful Lake Eola!! Spanish style retreat with maintenance ...

3 Beds
3.5 Baths
Casa Eola Condo Or 6062/4341 SubDv.
32803 Zip Code

260 S Osceola Avenue Unit 1104, Orlando image

260 S Osceola Avenue Unit 1104, Orlando — Star Tower $749,900 ▼

STAR TOWER condominium, SOUTHEAST CORNER UNIT, 2 bed/2.1 bath,2,000 SQ FT, Floor-To-Ceiling glass, with 2 PARKING SPOTS. Located in the South Eola District, with brick li...

2 Beds
2.5 Baths
Star Tower Condo SubDv.
32801 Zip Code

322 E Central Boulevard Unit 401, Orlando image

322 E Central Boulevard Unit 401, Orlando — The Waverly $900,000 ▼

Combining the spaciousness of an urban loft with the luxurious finishes and picturesque view only a select few condos in Orlando can offer, Residence 401 at The Waverly i...

2 Beds
2 Baths
The Waverly SubDv.
32801 Zip Code

101 S Eola Drive Unit 521, Orlando image

101 S Eola Drive Unit 521, Orlando — 101 Eola $550,000

Located in the heart of the South Eola District, this condo-home has been impeccably renovated with the highest quality finishes. Floor-to-Ceiling windows invite the beau...

2 Beds
2 Baths
101 Eola Condos SubDv.
32801 Zip Code

576 S Osceola Avenue Unit 16, Orlando image

576 S Osceola Avenue Unit 16, Orlando — Na $735,000 ▼

Step into refined luxury and unparalleled comfort with this exceptional 3 bed/ 3 bath lakefront residence. The attention to detail is evident from the moment you arrive, ...

3 Beds
3 Baths
Cherokee Place Condo Ph 01 SubDv.
32801 Zip Code

Call Me Today!

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Testimonials

Scott H.: Very Professional and one of the most responsive people I've ever met. Day or night, weekday or weekend, Rob would respond and always had my best interests at heart (he even apologized one time for taking 65 minutes to respond to my text!!). The selling process for me was not an easy one due to several factors (shady buyers, (buyers) agents, delays and a failed contract, etc.) but Rob maintained his poise and calm and helped me through it all with flying colors! I would recommend him to anyone and everyone!!

Wael Y: Rob was extremely professional and very knowledgeable. He answered phone calls and text messages immediately. He made sure that all of our questions were answered. Thank you Rob for your excellent service!

Brittany M: Rob was my Realtor several years ago. He helped me through the short sale process, which seemed scary at first, but Rob took care of just about everything! I never had to work and Rob was incredibly communicative through the whole sale. He got me the sale price I was hoping for. Rob is a great resource and I highly recommend him.

Janina C: His professionalism is par excellent. Robert was there for me all the way. He sold my home after two days of listing! I can best describe him as "ethical" Thank you very much for all your hard work. We are all very grateful. From the family Estate of Efigenia Marcum Inghram.

Kristi R: Simplicity is an excellent real estate brokerage company that makes the buying/selling of real estate a wonderful experience. The real estate process has always been a bit challenging to me and I viewed working with real estate agents as I did working with a "used car salesman". However, with the help of the owner/president, Rob Sassos, his compassion for the industry, the time he dedicated to working with me in finding my perfect home and his excellent customer service skills, the purchase of my new home ended up being a very pleasant and informative experience. In addition, simplicityre.com has an amazing tool to utilize while searching for a new home. It is very easy to use as well as informative. Another added bonus were the emails sent to me to update me daily on new listings in my area as well as price reductions on currently listed homes. I would recommend Simplicity to anyone and everyone looking to purchase or sell real estate. This is the first time I have had such a great experience and will definitely use them in the future. Thank you!

Brad & Valentina J: Robert Sassos assisted us with the shortsale of our townhome back in 2010. The service and assistance we received was way above expectations. Rob was very assertive and proactive and the whole process took a relatively short time. We were extrememly satisfied and thankful! We will defintely contact him again in the future for any assistance in the field.

Vince & Erin P: Rob was a huge help to us when we were trying to sell our house during the housing slump. He continued to find perspective buyers and we were able to sell the home when nothing much was selling in the area. I would highly recommend him!

Amy L: Robert was great to work with, we had a limited time frame so we had to look at several houses in a short amount of time. We finally found our new home, and are very happy!

Ron & Paola H: The best in the biz hands down. Would not use anyone else. Extremely knowledgeable. Would definitely use Rob for buying or selling any type of property and recommend him to anyone. .