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

555 N Fern Creek Avenue Unit 1, Orlando image

555 N Fern Creek Avenue Unit 1, Orlando — 1 $625,000

Just half a mile from Lake Eola and steps from the energy of downtown Orlando, this craftsman-style residence places you in the heart of it all. Stroll to Publix or the b...

3 Beds
4 Baths
Concord Place SubDv.
32803 Zip Code

260 S Osceola Avenue Unit 1602, Orlando image

260 S Osceola Avenue Unit 1602, Orlando — Star Tower $559,000

Virtually Staged. High above Downtown Orlando on the 16th floor of Star Tower, #1602 offers something that immediately sets it apart—a high-floor location with wide-open ...

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

636 Mariposa Street, Orlando — 636 $870,000

Welcome to the Brownstones at Thornton Park, where downtown living meets elevated style and privacy. This prime end-unit offers abundant natural light, a private setting,...

3 Beds
4 Baths
Brownstone/Thornton Park SubDv.
32801 Zip Code

828 E Washington Street, Orlando — 828 $575,000

Discover a rare opportunity to own a unique live-work townhome in the heart of Thornton Park, just a few blocks from the iconic Lake Eola Park and close to Downtown Orlan...

3 Beds
3 Baths
Thornton Place Twnhms SubDv.
32801 Zip Code

759 Lake Baldwin Lane, Orlando — Lake Baldwin 5 $555,000

IMMERSIVE AND INTERACTIVE 3D WALKTHROUGH — EXPLORE BEFORE YOU SCHEDULE A SHOWING. Click the VIRTUAL LINKS and step inside. This is the townhome that finally answers the q...

3 Beds
3 Baths
Lake Baldwin 5 SubDv.
32803 Zip Code

1012 E Marks Street, Orlando — 1012 $615,000

1012 E Marks Street. Located in the desirable Lake Highland Park neighborhood, Orlando’s Park Lake/Highland, one of Orlando's most desirable neighborhoods, this exception...

3 Beds
4 Baths
Park Lake Hlnd SubDv.
32803 Zip Code

1606 Park Lake Street Unit 9, Orlando image

1606 Park Lake Street Unit 9, Orlando — Park Lake 9 $634,900 ▼

Private Elevator | No HOA | Luxury 2023-Built Contemporary Townhome | Attached 2-Car Garage with EV Charger. Discover elevated living in this luxury contemporary townh...

3 Beds
4 Baths
Ferncreek 20 SubDv.
32803 Zip Code

1607 Woodward Street Unit 11, Orlando image

1607 Woodward Street Unit 11, Orlando — 11 $625,000 ▲

Seller is now offering $10,000.00 towards closing costs/rate buy downs! Welcome to 1607 Woodward Street, Unit11. This oasis is a true standout, offering a perfect blend o...

3 Beds
4 Baths
Ferncreek 20 SubDv.
32803 Zip Code

858 N Thornton Avenue, Orlando — Na $599,000 ▼

Urban living at its best in the heart of Orlando! This 3-story Nantucket model by David Weekley Homes offers 3 bedrooms, 3.5 baths, a 2-car attached garage, and a smart l...

3 Beds
4 Baths
Park Lake Hlnd SubDv.
32803 Zip Code

548 S Osceola Avenue, Orlando — 548 $619,900 ▼

One or more photo(s) has been virtually staged. Nestled among the brick-lined streets of the highly sought-after Lake Cherokee Historic District, this stunning corner-uni...

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

1010 E Robinson Street, Orlando — Jordan Homes $1,095,000

BRAND NEW! NOW AVAILABLE! Over $65k of complimentary upgrades of elevator, upgraded cabinetry, modern wine wall staircase lighting for the first sales. Units professional...

3 Beds
4 Baths
Vilasa Thornton Park SubDv.
32801 Zip Code

665 Jackson Street, Orlando — Brownstones Atthornton Park $819,000 ▼

BUYER INCENTIVES BUYER INCENTIVES BUYER INCENTIVES BUYER INCENTIVES BUYER INCENTIVES BUYER INCENTIVES Seller is offering a $10,000 buyer incentive that can be used ho...

3 Beds
4 Baths
Brownstones Of Thorton Park SubDv.
32801 Zip Code

525 E Jackson Street Unit 301, Orlando image

525 E Jackson Street Unit 301, Orlando — The Jackson $715,000

Welcome to Unit 301 at The Jackson Condominium, a fully furnished boutique residence in the heart of Orlando. This corner unit offers a turnkey luxury lifestyle with des...

3 Beds
2 Baths
Jackson SubDv.
32801 Zip Code

525 E Jackson Street Unit 401, Orlando image

525 E Jackson Street Unit 401, Orlando — The Jackson $740,000

Welcome to Unit 401 at The Jackson Condominium, a fully furnished boutique residence in the heart of Orlando. This corner unit offers a turnkey luxury lifestyle with des...

3 Beds
2 Baths
Jackson SubDv.
32801 Zip Code

530 E Central Boulevard Unit 1901, Orlando image

530 E Central Boulevard Unit 1901, Orlando — 530 $1,099,000 ▼

High above Lake Eola in the heart of Downtown Orlando, this ultra-luxury two-story penthouse offers an unparalleled living experience for those who value privacy, sophist...

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

460 E Jackson Street Unit 2, Orlando image

460 E Jackson Street Unit 2, Orlando — 460 $589,900 ▼

Executive living right in the middle of Downtown Orlando. PRIVATE GARAGE This 2 bedroom, 2.5 bath is a rare find, completely renovated: new paint, NEW ac, totally new k...

2 Beds
3 Baths
Osceola Brownstones SubDv.
32801 Zip Code

525 E Jackson Street Unit 402, Orlando image

525 E Jackson Street Unit 402, Orlando — Jackson/402 $879,900

Experience refined urban living at The Jackson, an exclusive boutique condominium residence nestled in the heart of South Eola / Thornton Park in Downtown Orlando. This e...

3 Beds
2 Baths
Jackson SubDv.
32801 Zip Code

1004 E Robinson, Orlando — Vilasa Thornton Park $980,000 ▼

BRAND NEW! NOW AVAILABLE! 3 bed/3.5-bathroom residence featuring an open loft-style living and kitchen design. An exceptional entry level opportunity enhanced by upgraded...

3 Beds
4 Baths
Vilasa Thornton Park SubDv.
32801 Zip Code

1008 E Robinson, Orlando — Jordan Homes $997,000

BRAND NEW! NOW AVAILABLE! 3 bed/3.5-bathroom residence featuring an open loft-style living and kitchen design. An exceptional entry level opportunity enhanced by upgraded...

3 Beds
4 Baths
Vilasa Thornton Park SubDv.
32801 Zip Code

155 S Court Avenue Unit P-2901, Orlando image

155 S Court Avenue Unit P-2901, Orlando — Solaire At The Plaza $1,190,000 ▲

Luxury High-Rise Living Above Downtown Orlando Discover elevated downtown living in this stunning high-rise residence at the acclaimed Solaire at the Plaza. Unit 2901 ...

2 Beds
2 Baths
Solaire/Plaza Condo 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. .