Great Expectations Realty - St. Augustine & Jacksonville

Great Expectations Realty - St. Augustine & Jacksonville This Local Family Owned Real Estate Brokerage specializes in Traditional Listings as well as Auction Augustine.
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Searching for your dream home isn’t always a seamless journey on your own, but one thing’s certain: A professional team can make a dream-home miracle happen. As market analysts and negotiation experts, we at Great Expectations are only the most dedicated realty professionals in St. With decades of combined broker experience and passionate problem solving, our growing team meets every new client with the answers they need to feel confident about the next big step. From empty-nesters and first-timers to retirees and high-end sellers, we are there to help you navigate the market without ever compromising the needs that make your journey unique. Each of their partnerships extends beyond a transaction -- it’s our promise to help you invest in a future that exceeds your expectations.

🏖️VILANO BEACH 🏖️ $699,000 📍503 22nd StSaint Augustine, FL 320843 bedrooms2 bathrooms2,521 sq ft 📲Jena Dennis 904-877-43...
09/28/2026

🏖️VILANO BEACH 🏖️ $699,000

📍503 22nd St
Saint Augustine, FL 32084

3 bedrooms
2 bathrooms
2,521 sq ft

📲Jena Dennis
904-877-4352

Welcome to 503 Twenty-Second Street, a beautifully maintained coastal retreat located in the highly desirable Vilano Beach/North Beach area of St. Augustine. Situated on an oversized lot just moments from the Atlantic Ocean, this spacious home offers the perfect combination of beachside living, comfort, and functionality. Built in 1994 and lovingly cared for by the same owners for more than two decades, the residence features an inviting floor plan designed for both everyday living and entertaining.

Upon entering, you are greeted by a dramatic two-story foyer and staircase that creates an impressive first impression. The main level offers multiple gathering spaces, including a spacious living room, formal dining room, formal sitting room, an eat-in kitchen, and a convenient half-bath powder room for guests. Large windows throughout fill the interior with natural light, creating a bright and welcoming atmosphere.

Upstairs, you’ll find three generously sized bedrooms, two full bathrooms, and a dedicated office or den, providing flexibility for remote work, hobbies, a reading room, or additional guest space. The spacious primary suite offers a comfortable retreat, while the additional bedrooms provide ample room for family and guests. Outdoor living is equally inviting with a rear deck that is perfect for relaxing, entertaining, grilling, or enjoying the coastal breeze.

🎃🧡EVENTS THIS FIRST WEEK OF OCTOBER in St. Augustine & St. Johns County, Florida: 🧡🎃Sept 28-Oct 30: River of Life United...
09/28/2026

🎃🧡EVENTS THIS FIRST WEEK OF OCTOBER in St. Augustine & St. Johns County, Florida:

🧡🎃Sept 28-Oct 30: River of Life United Methodist Church Pumpkin Patch, M-F 2-8 PM, Sat 10-8 PM, Sun 11-8 PM
📍2600 Race Track Rd
St. Johns, Florida

🎸🎶Sept 30: Music & Art by the Sea at the St. Augustine Beach Pavilion. Jim Stafford and The All Stars will perform from 7-9 PM

👻📺 Sept 30-Nov 2: Boat Drinks Haunted Hideaway with classic horror films and themed cocktails
📍123 San Marco Ave

🎤🎸 Oct 1-29: STA Songwriter Competition at Spinster Abbott’s, hosted by Amy Hendrickson. 20 Top Contestants will comptwe hit Best Singer-Songwriter in St. Augustine. Oct 1, 8, 22 & 29
📍61 San Marco Ave

☕️🕷️ Oct 1-31: The Haunted Coffee Shop at St. Augustine Coffee House with spooky decor and Halloween themed coffee, matcha and sweet treats
📍6 St. George St

🦇🍸 Oct 1-31: Forgotten Tonic Halloween pop-up with seasonal cocktails in spooky mugs and decor
📍6 Aviles St

🎨🖼️ Oct 2: First Friday Art Walk from 5-9 PM on 30+ galleries

🎭🍽️ Oct 2-3 and Oct 30: The Gilded Cage Supper Club: A Murder Mystery Theatre Experience at The Venue in Hastings
RSVP: https://www.hastingsfl.org/event/the-gilded-cage-murder-mystery-dinner/

🪦🕯️Oct 2-31: Mortality & Mourning: Women in Black — Candlelight Tours at the Ximenez-Fatio House Museum 📍20 Aviles St
RSVP: https://ximenezfatiohouse.org/tours/

🎀🏃‍♂️Oct 3: Pink up the Pace 5K Run/Walk
REGISTER: https://runsignup.com/Race/FL/StAugustine/PinkUpThePace5kWalkRun

🐊🍺 Oct 3: Croctober Fest Brew at the Zoo at the St. Augustine Alligator Farm
TICKETS: https://alligatorfarm.com/events-programs/community-events/croctoberfest/

🎃Oct 3-31: Happy Haunts pumpkin patch in Ponte Vedra
M-F 3-7; Sat 11-9; Sun 11-7
📍895 Palm Valley Rd

🌽🚜 Oct 3-Nov 1: Crop Maze at Sykes Family Farms
— nice acres of fall family fun. TICKETS:
https://sycofarms.com

🌮🥗💃🏽Oct 4: Taste of Latino Festival at Francis Field from 12-6 PM with live music by the Mambo LeBron Orchestra, salsa and Zumba dancing, and a Top Latino Chef contest. Food vendors will have empanadas, Cuban sandwiches, pinchos, and other Latin foods. Free admission

🛍️🥕Oct 4: North City Farmers Market 9 -1 behind Schooner’s

🍎🍊Oct 4: St. Augustine Farmers Market 9-1 at the Classic Car Museum

🌴PRICE DROP🌴 $464,000 ⬇️$14K272 Deer Crossing RdSaint Augustine, FL 320864 bedroom, 3 bathroom 📲 The Fearing Team Rachae...
09/25/2026

🌴PRICE DROP🌴 $464,000
⬇️$14K

272 Deer Crossing Rd
Saint Augustine, FL 32086
4 bedroom, 3 bathroom

📲 The Fearing Team
Rachael & Pete Fearing
904-352-9318

Welcome to the largest home in the neighborhood which gives you a split floorplan with 4 bedrooms, 3 full bathrooms, and a HUGE 3 car garage. High ceilings and open concept central common areas are ideal for family time and entertaining guests. Granite counters and stainless steel appliances throughout. Enjoy lots of natural light with a water view through the large 3 panel glass sliders really make this home stand out. Large Florida room shares the water view and faces North keeping the sun out of your eyes while enjoying your morning coffee on the porch. Enjoy a community pool, fitness center with workout room, basketball court soccer field and a playground all with a low HOA fee. Sidewalks make this neighborhood walkable, and a perfect location minutes from I-95, historic downtown St Augustine and our beautiful beaches!

09/24/2026

🗝️JUST SOLD 🗝️$2,400,000

📍268 Saint George Street
Saint Augustine, FL 32084

7 beds
5 baths
5,800 sq ft

📲 Jena Dennis, representing the buyers
904-877-4352

Step into the enchanting embrace of the notable Upham Winter Cottage, a captivating Queen Anne Victorian nestled on a quarter-acre lot within the heart of St. Augustine’s cherished historic preservation district and listed on the National Register ofHistoric Places. This world-class historic mansion has recently been renovated from top to bottom to perfection with soft coastal hues in mind ~ enjoy the well-designed balance of rich historic beauty and modern luxury. With 5800 sq ft of living space, 5 bedrooms and 3.5 bathrooms in the main house and a 2 bedroom, 1 bath apartment with private entrance, a full kitchen, living and dining room - this home is ideal for multigenerational living or additional income. Located on historic St.George Street, the shops, restaurants, landmarks and culture of the Nation’s Oldest City are only steps away. Listed by Kate Mitchell.

🍺🍖🍹JACK’S BBQ & BREWERY FOR SALE! $7,200,000691 A1A Beach BlvdSt. Augustine Beach, Florida 32080📲 Jena Dennis904-877-435...
09/23/2026

🍺🍖🍹JACK’S BBQ & BREWERY FOR SALE! $7,200,000

691 A1A Beach Blvd
St. Augustine Beach, Florida 32080

📲 Jena Dennis
904-877-4352

Prime Commercial Opportunity positioned just 500 feet from beach access in the heart of St. Augustine Beach. This rare offering consists of two distinct parcels with frontage along A1A Beach Boulevard.

🍽 The first parcel is home to the beloved Jack’s Bar-B-Que, a local landmark since the 1940s, featuring four detached buildings, a spacious deck, a pool, and multiple bar areas that create a lively dining and entertainment destination.

🍻 The second parcel, The Brewery at Jacks Bar-B-Que, was built in 2022 and includes a fully equipped brewery with a 7 BBL boiler system, a bar overlooking the brewing hall, and an upstairs office space. The brewery seamlessly supplies fresh craft beer to Jack’s, enhancing the overall customer experience.

🍷Both parcels benefit from an invaluable 4COP Quota license with 3M & CMBP modifiers, which is transferable should a buyer choose to redevelop the property.

🚗 Spanning approximately 25,000+ sq ft (.60 acres), the property boasts 200 feet of visible frontage along A1A Beach Boulevard and 150 feet along A Street, with direct access to a city-owned public parking lot and additional on-site parking.

🚦Positioned at a busy, signalized intersection, the site enjoys excellent visibility and high traffic exposure, benefiting from the area’s mix of commercial, residential, retail, and dining establishments.

🐖 Jack’s Bar-B-Que consists of four buildings, including the original restaurant structure rewired and re-plumbed in 2001, a pool for patrons to enjoy, a second bar with an 800-square-foot wooden deck, an entertainment space with billiards, and a back-of-house area with a rebuilt BBQ pit and storage facilities.

🍺 The brewery, located next door at 681 A1A Beach Blvd, features a deck with poolside seating, a well-appointed interior bar, and a second-floor office.

🔥 This exceptional investment opportunity offers unmatched potential in a high-demand coastal location, whether maintaining the established businesses, expanding operations, or exploring redevelopment possibilities.

  ☕️🌹🥐 NEW CAFÉ! La Roseta Cafe opened earlier this month in St. Augustine’s historic district! Fresh pastries, gourmet ...
09/23/2026

☕️🌹🥐 NEW CAFÉ! La Roseta Cafe opened earlier this month in St. Augustine’s historic district! Fresh pastries, gourmet coffee, sandwiches and stunningly decorated sweets are on the menu.

📍210 St. George Street
St. Augustine, Florida

Locally owned by the same couple that brought our community The Roost • Rotisserie Chicken & Latin Cuisine on State Road 16. 💕

The best part: Collaboration events will be happening throughout fall with other local businesses! A true community connection.

FOLLOW: LA ROSETA CAFÉ | ST. AUGUSTINE

Address

105 S Ponce De Leon Boulevard
Saint Augustine, FL
32084

Opening Hours

Monday 9am - 6pm
Tuesday 9am - 6pm
Wednesday 9am - 6pm
Thursday 9am - 6pm
Friday 9am - 6pm
Saturday 9am - 6pm
Sunday 9am - 6pm

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