Imagine owning a slice of Florida’s finest, where luxury meets privacy across diverse landscapes. From Winter Park’s historic, tree-lined streets to Saint Cloud’s sprawling no-HOA estates and Gulf Breeze’s secluded retreats, these five properties, ranging from $1,250,000 to $1,395,000, redefine indoor-outdoor living. With resort-style pools, spacious layouts, and unique features like tennis courts and workshops, each home offers versatility and charm. Nestled on large lots with natural surroundings, they promise space for personalization and endless enjoyment in some of Florida’s most coveted and emerging locations.
Welcome To Private Paradise | $1,300,000


Monica Mortara

Monica Mortara
Tucked away on 1.4 acres of serene countryside, this rural estate offers a harmonious blend of privacy and modern comfort. Surrounded by majestic oaks and meticulously landscaped grounds, the property features a beautifully updated home with new hardwood oak floors, fresh paint, and a stunning marble kitchen with a spacious island. The open floor plan seamlessly connects the kitchen to a grand great room, where a gas fireplace adorned with Italian herringbone tile creates a warm focal point. Outside, a custom lap pool and jacuzzi, installed in 2023, invite relaxation, while a Har-Tru clay tennis court and over 600 square feet of screened porch with a wood-burning fireplace elevate outdoor living. Additional highlights include a detached 200-square-foot dwelling for guests or an office, an oversized two-car garage, and space for an RV or boat. With no HOA and proximity to boat ramps, shopping, and top schools, this estate embodies tranquil versatility.
- Price:
- $1,300,000
- Size:
- 2,719 sq ft
- Contact:
- Monica Mortara, LPT Realty, 850.565.7600
Charming Winter Park Pool Home – A Rare Opportunity | $1,395,000


Jackie Swisher

Jackie Swisher
Rising above the picturesque landscape of Winter Park’s coveted 32789 zip code, this 4-bedroom, 3-bathroom pool home exudes timeless charm and boundless potential. Positioned on a sprawling corner lot, the residence is mere steps from Phelps Park, enveloped by tree-lined streets, and just moments from the vibrant retail and dining of Winter Park. Inside, a gracious foyer opens to formal living and dining areas, where oversized windows bathe the spaces in natural light. The expansive kitchen, complete with wood cabinetry, a pantry, and a wine fridge, seamlessly blends functionality with style. French doors reveal a charming courtyard walkway leading to a tranquil pool, ideal for relaxation or gatherings. The primary suite, with direct pool access, boasts an updated ensuite featuring a soaking tub and dual sinks. With a detached 2-car garage and freshly painted interiors and exteriors in 2025, this home offers a canvas for your vision in a truly exceptional location.
- Price:
- $1,395,000
- Size:
- 2,841 sq ft
- Contact:
- Jackie Swisher, Trust Equity Group Real Estate, 615.473.9071
LaidBack Luxury On 3 Acres | $1,350,000


Allison Day

Allison Day
Set against the serene backdrop of waterfront beauty, this custom-built estate on 3.15 acres offers a harmonious blend of space and tranquility. The main residence captivates with an open, light-filled layout, featuring luxury vinyl plank flooring and floor-to-ceiling windows that frame stunning views. A chef’s kitchen, complete with double islands and stainless steel appliances, anchors the heart of the home. Upstairs, the primary suite and loft open to private balconies overlooking a resort-style pool and heated spa. Four of the five bedrooms boast en-suite baths, while a separate in-law suite—with two bedrooms, a full kitchen, and pool access—provides ideal flexibility for guests or family. A covered courtyard seamlessly connects indoor and outdoor spaces, enhancing the flow to the screened pool area. With an oversized workshop garage and a golf cart-friendly locale near Lake Nona, this estate embodies relaxed, versatile living.
- Price:
- $1,350,000
- Size:
- 3,439 sq ft
- Contact:
- Allison Day, RE/MAX Town & Country Realty, 407.617.2881
Investment Property Potential | $1,250,000


Miguel Kaled

Miguel Kaled
Situated in the heart of Kissimmee, this prime urban property offers a remarkable canvas for visionary developers. Positioned just moments from Downtown Kissimmee, Poinciana, and major attractions, it ensures seamless connectivity with easy access to I-4 and the Turnpike. The location strikes a perfect balance between convenience and opportunity, with the nearby Route 192 Walmart Superstore adding everyday practicality for future residents. This versatile parcel presents exciting potential, accommodating plans for either a 32-unit townhouse community or a 44-unit condominium or apartment complex. Its strategic setting caters to a vibrant urban lifestyle, where proximity to shopping, entertainment, and key transit routes enhances daily living. Ideal for those looking to shape a thriving residential hub, this property embodies the pulse of city life while offering the flexibility to create a tailored development in a sought-after area.
Size: 7.95 acres
- Price:
- $1,250,000
- Contact:
- Miguel Kaled, J-Mark Realty Collection, 407.467.9446
Coastal Luxury In Ocean Hammock | $1,250,000


Teresa Brown & Anita Crocker

Teresa Brown & Anita Crocker
Set against the serene backdrop of Ocean Hammock, one of Florida’s premier oceanfront communities, this custom-designed pool home embodies timeless elegance. Overlooking a tranquil lake and the renowned Jack Nicklaus Signature Ocean Course, the residence features three bedrooms, two and a half baths, a dedicated office, and a formal dining room. Grand double doors reveal a striking two-story great room, where soaring ceilings and expansive glass walls seamlessly blend indoor and outdoor beauty. The gourmet kitchen, with its large island, custom cabinetry, and walk-in pantry, caters to both casual meals and lavish gatherings. Unwind by the private pool, take a short stroll to nearby beach access, or explore scenic A1A’s dining and attractions. Optional Hammock Beach Club memberships unlock access to championship golf, oceanfront pools, tennis, and a luxurious spa, enhancing the coastal lifestyle in this exceptional retreat.
- Price:
- $1,250,000
- Size:
- 3,121 sq ft
- Contact:
- Teresa Brown & Anita Crocker, Realty Executives Oceanside, 386.864.3599 , 386.503.0221












