• Main House

  • Second House

  • Both Homes

  • A wonderful, treed oasis in the middle of town

  • Spacious deck, main house

  • Living area, main house

  • Kitchen, main house

  • Master bedroom, main house

  • Bedroom 2 (of 3), main house

  • Spacious deck, second home

  • Kitchen, second home

  • Living area, second home

  • Bedroom 2 (of 2), second home

  • Garage, second home

  • Drive leading into the estate


I think I’m in love! Tell me more about this home!

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2365 and 2355 Rolling Hills Drive

Broker Sean Hess did the photography, video, and marketing for this home that brought multiple offers. Meet Sean Hess.

Green space is at a premium in this town, especially close in, and I don’t need to tell you about affordability. But here’s something really fantastic that you may never see again: Two fantastic homes, for one price, with five glorious acres of tall trees, and it’s all within five minutes of downtown St. Augustine (give or take a few minutes if the traffic is heavy). The main home has 3 bedrooms and 2 baths, and the second home has 2 bedrooms and 2 baths. BOTH homes include an ADDITIONAL mother in law suite on ground floor (they are both two-story homes), and both are modern homes (build date is 2003). The homes each have large and covered decks, and they each have oversized 2+ car garages with 9-foot doors (!) and 10 foot ceilings (plenty of room for boats, trailers, vans – you name it). The homes have 220 feet of road frontage on Rolling Hills Drive. Approximately 4 acres could be developed … could be … but my guess is that you never will. Why? Because you’re going to live large here in this intoxicating oasis of green, close to all the beauty and history St. Augustine has to offer, and you just can’t get this anywhere. Buyer to verify all measurements. SOLD: $460,000

Find out More

Use the contact form at bottom of the page or contact Sean Hess at Sean@StAugTeam.com

Size & Price

The main house is 1,568 square feet (does not include square footage downstairs or mother in law suite). The second home is 1,352 square feet (also does not include downstairs or mother in law suite). These homes are offered together for $469,000.

Main House, Bedrooms and Baths

The main house has 3 bedrooms and 2 baths (this does not include the downstairs mother in law suite).

Kitchen and Dining, Main House

The 12 x 10 kitchen includes a wonderful breakfast bar, and opens to the the living and dining areas, which is fabulous when you have a large gathering and want to stay in the middle of things. The dining area is 10 x 10.

Living Area, Main House

The 26 x 14 living room is a big, big area that opens to the kitchen and dining room, keeping everything inviting when you have a large gathering.

Master Bedroom and Master Bath, Main House

The 17 x 13 master bedroom looks out onto the patio, has a pretty attached bath, and a big walk-in closet.

Guest Bedrooms (2) and Guest Bath, Main House

There are two guest bedrooms in addition to the master. The bedrooms are approximately 12 x 11 and 14 x 10 respectively.

Second Home, Bedrooms and Baths

The second home has 2 bedrooms and 2 baths, which does not include the extra suite and bath downstairs.

Kitchen and Dining, Second Home

The second home has a 12 x 10 kitchen that opens into the living and dining areas. The dining area is approximately 10 x 10.

Living Area, Second Home

The second home has a spacious 23 x 14 living area. Like the main home, the living area opens to the kitchen and dining areas.

Master and Guest Bedrooms, Second Home

The master bedroom is a large 14 x 10 space, while the guest bedroom measures 11 x 10.

Patios and Decks

Oh, you will so entertain here! The main home includes a 40 x 14 covered deck, while the deck for the second home is a shade smaller at 35 x 14. Can’t you just imagine the possibilities?


I sure hope you have race cars, or boats, or something else big and impressive, because each home has a gigantic garage. Each has twin 9-foot high doors, and each has 10-foot ceilings. You could probably put a dozen four-wheelers in those spaces. Or a casino. Just sayin’.


This home is currently zoned for Osceola Elementary, R.J. Murray Middle School, and Pedro Menendez High School.

Lot Size and Acreage

This wonderful oasis in the middle of St Augustine is approximately 220 feet wide by 768 feet deep, working out to roughly 5.11 acres.

Room Sizes
Main home: 3 bedrooms, 2 baths, 1568 square feet (upstairs square footage only)Main home: Kitchen 12 x 10
Main home: Dining Room 10 x 10 Main home: Living Room 26 x 14
Main home: Master Bedroom 17 x 13Main home: Bedroom 2, 12 x 11
Main home: Bedroom 3, 14 x 10Main home: 40 x 14 covered patio
Second home: 2 bedrooms, 2 baths, 1352 square feet (upstairs square footage only)Second home: Kitchen, 12 x 10
Second home: Dining, 10 x 10Second home: Living Area, 23 x 14
Second home: Master Bedroom, 14 x 10Second home: Bedroom 2, 11 x 10
Second home: Patio, 35 x 14, coveredBOTH HOMES: Parking, 2 car garage each, with 9′ doors and 10′ ceilings
BOTH HOMES: Each are 2-storiesBOTH HOMES: Each has a separate suite downstairs, not included in the square footages
Lot is 220 wide by 768 deep and 5.11 acres approximately.Buyer to verify all measurements