Hillsborough Homes with Deed Restrictions Community Features

Hillsborough Homes with Deed Restrictions Community Features

Welcome to Hillsborough County, Florida, a vibrant and diverse region that perfectly blends the charm of suburban living with the excitement of urban amenities. Nestled on the west coast of Florida, Hillsborough County is home to bustling cities like Tampa and Plant City, along with beautiful natural landscapes, making it an ideal place for families, professionals, and retirees alike.

One of the standout features of Hillsborough County is its array of homes within deed-restricted communities. These neighborhoods often provide a sense of security and community pride, with established guidelines that help maintain property values and enhance the overall aesthetic of the area. Residents can enjoy beautifully landscaped surroundings, well-maintained common areas, and a variety of recreational facilities, including parks, playgrounds, and community pools.

Living in a deed-restricted community in Hillsborough means you can take advantage of the numerous local amenities, such as shopping centers, restaurants, and entertainment venues, all while enjoying the peace of mind that comes from living in a well-regulated neighborhood. These communities often host events and activities that foster a strong sense of camaraderie among residents, making it easy to form lasting friendships and connections.

Whether you’re looking for a cozy single-family home, a modern townhouse, or a spacious estate, Hillsborough County has something to offer everyone. Experience the perfect blend of community, convenience, and natural beauty in this enchanting corner of Florida. Discover your dream home in Hillsborough County today!

Newest Hillsborough Homes with Deed Restrictions Community Features

$299,000
2 Beds 2 Baths Del Webbs Sun City Florida Un SubDv. 33573 Zip Code
Designed for elevated comfort and effortless modern living, this fully updated 2-bedroom, 2-bath, 1,402 sq ft home is located in the heart of Sun City Center’s premier 55+ Del Webb community. Complete with key 2026 systems updates, this residence offers an exceptional move-in-ready lifestyle in one of the best 55+ Communities in the USA! From the fresh interior and exterior paint to the sun-lit, open-concept design, every detail reflects a clean, contemporary aesthetic. The heart of the home features a chef-inspired kitchen anchored by a large central island, perfect for entertaining or casual dining. Featuring a seamless open-concept living and dining area plus a massive additional family room, this layout provides exceptional space for entertaining and hosting family and friends. The primary suite serves as a luxurious retreat, featuring a custom built-in makeup vanity and an elegant ensuite bath. Outdoor living is made easy with a spacious backyard enclosed by a brand-new 2026 vinyl privacy fence. Functionality meets convenience in the two-car attached garage, which includes a dedicated built-in workshop room ideal for projects, storage, crafts, or hobby space. Capital improvements provide complete peace of mind, featuring a brand-new roof (2026), new A/C system (2026), new water heater (2026), and a new privacy fence (2026). Sun City Center residents enjoy an active adult lifestyle with access to fitness centers, indoor and outdoor pools, golf courses, pickleball and tennis courts, vegetable garden, dog parks, a woodworking shop, arts and crafts studios, and nearly 200 social clubs. Golf carts are the preferred mode of transit to local shopping, dining, and daily conveniences, with easy access to I-75 for simple trips to Tampa, Sarasota, and Gulf Coast beaches. This turn-key home blends modern design, structural updates, and prime Florida living—schedule your private tour today!

1406 Seton Hall Drive, Sun City Center

$369,900
4 Beds 3 Baths Summerfield Village 1 Tr 28 SubDv. 33579 Zip Code
Virtually Staged. Welcome home to 12914 Longcrest Drive! This beautifully updated Riverview home offers a bright, open layout with plenty of space to spread out and enjoy. Step inside to soaring ceilings, abundant natural light, fresh neutral finishes, and easy-care flooring that flows throughout the main living areas. The updated kitchen features white shaker-style cabinetry, granite countertops, tile backsplash, stainless steel appliances, generous cabinet and counter space, and a light-filled dining area overlooking the backyard. Multiple living and dining spaces provide flexibility for everyday living, entertaining, a home office, or additional gathering space. The spacious primary suite offers plenty of room to unwind, while the home's functional floor plan provides comfortable separation of living and sleeping areas. Additional features include an interior laundry room, updated lighting, ceiling fans, a two-car garage, and a screened outdoor living area perfect for enjoying Florida living year-round. Outside, mature trees provide shade and character, creating an established setting that is increasingly hard to find. Conveniently located in Riverview with easy access to shopping, dining, schools, recreation, major roadways, I-75, and everything the growing SouthShore area has to offer. Clean, updated, spacious, and ready for its next owner — schedule your private showing today!

12914 Longcrest Drive, Riverview

$299,000
2 Beds 2 Baths Medley At Southshore Bay SubDv. 33598 Zip Code
WELCOME TO MEDLEY AT SOUTHSHORE BAY — WHERE THE FLORIDA LIFESTYLE COMES WITH THE KEYS… AND THE GOLF CART! Offered at an incredible $299,000, this beautifully upgraded villa at 17319 Hollywell Avenue delivers style, comfort, and exceptional value in one of the area’s most sought-after 55+ communities — and YES, the golf cart conveys with the home! Step inside and immediately see why this villa stands apart. Thoughtful upgrades and designer touches create a home that feels anything but ordinary. The beautifully reimagined kitchen is a showstopper, featuring quartz countertops, custom cabinetry, a dedicated coffee bar, and a THOR induction cooktop — combining sophisticated style with everyday functionality. The open and inviting floor plan offers 2 bedrooms, 2 full baths, plus a versatile bonus/flex room perfect for a home office, den, hobby space, or additional sitting area. Upgraded flooring flows throughout the living areas, creating a polished, cohesive look with easy Florida living in mind. Step outside to the screened lanai, complete with convenient roll-down screens, and enjoy your own private space for morning coffee, evening cocktails, or simply relaxing after a day enjoying everything Medley has to offer. Additional features include smart-home technology and a tankless water heater, adding both convenience and efficiency. And then there’s THE LIFESTYLE. Medley at Southshore Bay is a gated, golf-cart-friendly 55+ community designed for residents who want more than just a beautiful home. Enjoy resort-style amenities including the spectacular Crystal Lagoon, clubhouse, resort-style pool, fitness center, pickleball, dining, social activities and events, and miles of opportunities to enjoy the Florida sunshine. HOA benefits also include lawn maintenance, cable and internet for truly low-maintenance living. Best of all? Your golf cart is already waiting for you! Hop in and head to the clubhouse, meet friends for dinner, enjoy an afternoon at the lagoon, or cruise the neighborhood in true Medley style. At $299,000, with extensive upgrades AND the golf cart conveying, this villa presents an outstanding opportunity to start enjoying the Medley lifestyle from DAY ONE. Beautifully upgraded. Exceptionally priced. Golf cart included. Welcome home to 17319 Hollywell Avenue!

17319 Holly Well Avenue, Wimauma

$389,000
3 Beds 3 Baths Forest Brooke Active Adult Phs SubDv. 33598 Zip Code
Exceptional 3-bedroom, 2.5-bath home featuring the highly sought-after Dawning floor plan in the gated 55+ community of Medley at Southshore Bay. This thoughtfully designed home offers a rare private suite layout along with a 2-car garage and a separate golf cart/storage garage. Attractive curb appeal begins with a paver driveway, manicured landscaping, and a covered front entry. Inside, the tiled foyer leads to a versatile flex room with custom lighting, perfect for a home office, den, or hobby room, along with a convenient half bath for guests. The gourmet kitchen is beautifully appointed with 42-inch cabinets with crown molding, quartz countertops, under-cabinet lighting, a large center island, walk-in pantry, gas range and premium KitchenAid refrigerator, and dishwasher. The kitchen opens to an expansive dining and living area with soaring ceilings, abundant natural light, and sliding glass doors leading to the covered screened lanai overlooking peaceful wooded views with no rear neighbors. The spacious owner's suite also enjoys the private wooded setting and features a large walk-in closet, dual vanities, and a walk-in shower. Two additional bedrooms and a full bath are positioned to create a private guest suite with convenient access to the garage, making it ideal for visitors. Additional upgrades include light wood-look tile flooring throughout the main living areas, 8-foot interior doors, custom lighting, a mudroom off the garage, natural gas heat and cooking, and a private backyard. Residents of Medley at Southshore Bay enjoy an exceptional active adult lifestyle with a resort-style clubhouse, fitness center, pickleball courts, swimming pools, walking trails, social events, and exclusive access to the Southshore Bay Lagoon. Conveniently located near US-301 and I-75, this home provides easy access to Tampa, St. Petersburg, Sarasota, Gulf Coast beaches, shopping, dining, grocery stores, and top-rated medical facilities including St. Joseph's Hospital-South and HCA Florida South Shore Hospital. Enjoy luxury, convenience, and low-maintenance living in one of the area's most desirable active adult communities.

5231 Windy Grove Drive, Wimauma

$329,500
3 Beds 2 Baths Sun City Center Unit 162 Ph SubDv. 33573 Zip Code
This charming and very popular St. Thomas Model offers 3 bedrooms, 2 baths, a split floor plan, and freshly painted interior. Step inside and take in the vaulted ceilings, abundant natural light, and an inviting view through the great room to the spacious tiled lanai overlooking the peaceful conservation and pond. The home features plantation shutters, tile flooring in wet areas and living areas, and laminate in the bedrooms. The spacious owner’s suite includes two walk-in closets, a garden tub, walk-in shower, double vanities and enclosed water closet for added privacy. The recently updated guest bath boasts a modern walk-in shower, while the versatile third bedroom (or office) has two closets for extra storage. The chef’s kitchen is designed for both function and charm with stainless appliances, plentiful cabinets with pull-outs, a center island, and cozy eat-in area with a cushioned window bench overlooking the pond and wildlife. Adjacent to the kitchen is a formal dining room perfect for gatherings. Additional highlights include: fresh interior paint, laundry room with sink, washer and dryer, extended 2-car garage with storage cabinets, attic access, keypad entry, screen, hurricane shutters, irrigation system, water softener, and newer freezer included. Also note the brick paver driveway, screened front porch, and colorful landscaping for great curb appeal. The tiled lanai is ideal for entertaining or simply enjoying the tranquil outdoor setting. All of this is located in the quiet, highly sought-after Caloosa neighborhood of Sun City Center. This 55+ golf cart–friendly community is designed with an active lifestyle in mind. Residents enjoy a wide variety of amenities including clubhouse, fitness center, indoor and outdoor pools, tennis and pickleball courts, and over 200 clubs and activities for every interest. Sun City Center is located between Tampa and Sarasota and so accessible to major airports, sporting events, amusement parks, and of course, beautiful Florida beaches. Schedule your showing today and see why this property presents one of the best values in Sun City Center!

739 Winterbrooke Way, Sun City Center

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