Southern Pines Homes with Rain Gutters Exterior Features

Welcome to Southern Pines, a picturesque subdivision nestled in the heart of Winter Garden, Florida. This charming community, located in Orange County, offers a perfect blend of suburban tranquility and modern convenience, making it an ideal place for families, professionals, and retirees alike.

Southern Pines boasts an array of beautifully designed homes, each featuring exquisite exterior details that enhance both aesthetics and functionality. One standout feature of many homes in this community is the inclusion of rain gutters. These practical additions not only protect your investment by directing water away from the foundation but also help maintain the beauty of your landscaping. With the sunny Florida weather, having rain gutters is essential in ensuring your home remains in pristine condition, especially during those summer showers.

The subdivision is surrounded by lush greenery and serene landscapes, providing residents with a peaceful retreat from the hustle and bustle of city life. Families will appreciate the proximity to top-rated schools, parks, and recreational facilities, while outdoor enthusiasts can enjoy nearby trails and lakes for hiking, biking, and fishing.

Southern Pines is also conveniently located near shopping centers, dining options, and entertainment venues, making it easy to enjoy all that Winter Garden has to offer. With its welcoming atmosphere, beautiful homes, and a strong sense of community, Southern Pines is not just a place to live; it’s a place to call home. Come discover why so many are choosing to settle in this delightful neighborhood!

Newest Southern Pines Homes with Rain Gutters Exterior Features

$1,550,000

4 Beds ⋅ 3 Baths ⋅ Southern Pines SubDv. ⋅ 33609 Zip Code

A rare South Tampa gem! This beautifully maintained 1927 Traditional home seamlessly blends timeless historic charm with thoughtful modern updates and exceptional indoor-outdoor living. The 2,804-square-foot main residence offers 4 bedrooms and 3 baths, along with a sparkling heated pool, beautifully landscaped and newly turfed backyard, and a detached 437-square-foot, 1-bedroom, 1-bath guest house. This truly special property offers a unique combination of character, flexibility, and functionality. The main home showcases gorgeous original hardwood floors, high ceilings, beamed ceilings, detailed millwork, and an inviting open layout filled with natural light. The updated kitchen features quartz countertops and stainless steel appliances and flows seamlessly into the spacious family room, where a wall of windows provides beautiful views of the backyard and pool. A first-floor bedroom and full bath offer excellent flexibility for guests, an office, or additional living space. Upstairs, the spacious primary suite features a beautifully appointed bath with dual sinks and a walk-in shower, while two additional bedrooms share a convenient Jack-and-Jill bath. A large second-floor terrace overlooks the backyard and pool, creating a wonderful space to enjoy your morning coffee or relax and entertain. Recent improvements provide peace of mind and modern comfort, including new roofs installed in 2024, new water heaters installed in 2024 and 2025, and all-new ductwork. The backyard has been newly turfed, creating a fresh, low-maintenance outdoor setting, while the pool heater was replaced in 2024, allowing for year-round enjoyment of the sparkling heated pool. The detached guest house adds even more versatility and includes a living area, bedroom, full bath with an original claw-foot tub, and kitchenette—ideal for guests, extended family, a private office, studio, or additional living accommodations. Beneath the guest house, an additional workshop/storage area provides abundant storage and incredible potential for a pool room, office, hobby space, or future finished area. Situated in a desirable South Tampa neighborhood with A-rated schools and convenient access to shopping, dining, parks, and all that South Tampa has to offer, this exceptional property is a rare opportunity to own a home where history, character, thoughtful updates, and modern living come together beautifully.

208 S Matanzas Avenue, Tampa

$290,000

3 Beds ⋅ 2 Baths ⋅ Southern Pines SubDv. ⋅ 34787 Zip Code

**Click the Virtual Tour Link for 3-D walk-through tour** Welcome home to this well maintained FIRST FLOOR 3-bedroom, 2-bath condominium in Winter Garden, ideally located near shopping, dining, and with easy access to major roadways for trips to the airport and theme parks. This corner unit condo offers convenience to parking and features an open floor plan with spacious living room plus a den - perfect for a home office or flex space. The kitchen includes a breakfast bar, pantry, and convenient laundry room just through the kitchen. The split floor plan provides privacy to the primary suite with walk-in closet, linen closet, and en-suite bathroom. Additional bedrooms also feature walk-in closets and the hallway bathroom has an extended vanity for extra space and storage. Residents of Southern Pines Condos enjoy an exceptional array of amenities such as a pool and spa, outdoor kitchen, clubhouse with theater, office space and billiards, indoor basketball and racquetball courts, fitness center, playroom, covered outdoor playground, tennis and beach volleyball courts, and a car wash station. The gated community's HOA fee includes cable, internet, water, sewer, trash, and exterior maintenance, making for a truly low-maintenance lifestyle. Call for a showing today!

200 Southern Pecan Circle Unit 104, Winter Garden

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