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$425,000
4 Beds ⋅ 2 Baths ⋅ Sterling Park Unit 04 SubDv. ⋅ 32707 Zip Code
Some homes simply check the boxes. Others invite you to slow down, settle in, and imagine the life waiting for you inside. Welcome to 304 Shadow Oak Drive—a thoughtfully designed single-story, 4-bedroom, 2-bathroom pool home nestled in one of Casselberry's established communities, where abundant natural light, generous living spaces, and timeless character come together. As you step through the front door, you're welcomed by an open, airy atmosphere filled with sunshine streaming through oversized windows. The spacious living room draws you in with its warm gas fireplace, creating an inviting focal point for cozy evenings, gatherings, or quiet moments of relaxation. Designed with a desirable split-bedroom floor plan, the home offers a functional layout that balances openness with privacy. The expansive dining area provides exceptional flexibility for everyday dining, entertaining, or special occasions, while the adjoining living spaces flow seamlessly, creating an inviting environment for both everyday living and hosting guests. Tucked away for added privacy, the spacious primary suite serves as a peaceful retreat at the end of the day—a comfortable space to relax, recharge, and make your own. The additional bedrooms offer flexibility for a variety of needs, while the thoughtful floor plan makes the home feel both spacious and connected. Step outside and discover what truly makes this property shine. The backyard unfolds into your own private Florida oasis, where the sparkling in-ground swimming pool and attached spa invite you to unwind beneath the Florida sunshine. Surrounded by a fully fenced backyard, this outdoor space offers the perfect setting for entertaining, relaxing, gardening, or simply enjoying the year-round Florida lifestyle. Whether you're hosting weekend barbecues, gathering around the pool, or savoring a quiet morning outdoors, this backyard was designed to be enjoyed. A large driveway provides ample parking for multiple vehicles and guests, while the low HOA adds convenience within this well-established neighborhood. Ideally located in the heart of Casselberry, Florida, this home offers convenient access to Red Bug Lake Road, State Road 436, US Highway 17-92, Interstate 4, and SR-417, placing you just minutes from Winter Park, Altamonte Springs, Longwood, Lake Mary, Downtown Orlando, Orlando Sanford International Airport, shopping, dining, parks, recreation, grocery stores and everyday conveniences. If you've been searching for a single-story pool home in Casselberry with 4 bedrooms, 2 bathrooms, a split floor plan, a gas fireplace, a fully fenced backyard, low HOA, and generous living spaces, 304 Shadow Oak Drive offers the perfect opportunity to add your own personal style while enjoying all the comfort, space, and convenience this Central Florida location has to offer. Schedule your private showing today and experience everything 304 Shadow Oak Drive has to offer today.

304 Shadow Oak Drive, Casselberry
$949,900
4 Beds ⋅ 6 Baths ⋅ Crystal Bowl Add SubDv. ⋅ 32707 Zip Code
Welcome to a truly one-of-a-kind waterfront estate where the tranquility of country living meets the convenience of city life. Nestled on nearly one acre of private lakefront property in the heart of Casselberry, this exceptional multigenerational home is an incredibly rare opportunity to own a custom-built retreat unlike anything else on the market. Designed with both everyday living and unforgettable entertaining in mind, this expansive residence offers incredible flexibility with multiple living areas and up to three potential primary suites, making it ideal for extended families, guests, or those seeking dedicated work-from-home space. Rich Brazilian hardwood floors add warmth and elegance to the formal living and dining rooms, while the spacious kitchen features a generous island with abundant prep space, creating the perfect gathering place for family and friends. The oversized bonus room offers endless possibilities as a home theater, fitness studio, game room, or creative space. Just outside, an elevated deck overlooks the sparkling pool, creating a seamless connection to the beautifully renovated detached guest residence. The detached suite is a true highlight, offering approximately 864 square feet of beautifully updated living space complete with one bedroom, one and a half bathrooms, & private accommodations ideal for multigenerational living, long-term guests, a home office, or gym. The convenient half bath also provides direct access from the pool area, making outdoor entertaining effortless. Mature trees provide a peaceful canopy over the nearly one-acre homesite. Whether you enjoy gardening, relaxing with a morning coffee, or simply taking in the serene surroundings, this property offers an outdoor lifestyle that is difficult to find. A spacious workshop shed provides the perfect space for hobbies, woodworking, storage, or DIY projects, complementing the detached two-car garage with additional parking for a boat, RV, trailer, and ample guest parking courtesy of the circular driveway. Enjoy private access to Lake Crystal Bowl, where fishing, kayaking, paddle boarding, and other non-gas-powered boating activities await. It's a peaceful waterfront setting that feels miles away from the city, yet places you in one of Central Florida's most convenient locations. Thoughtfully updated throughout, the home features six beautifully remodeled bathrooms, four air conditioning systems, three of which have been replaced within the last five years, new roof, new electrical panels & outlets, new garage door, updated knockdown ceilings, energy-efficient LED recessed lighting, a new sprinkler system, updated main primary bathroom, new windows, and so much more! Perfectly situated in a quiet, established neighborhood within the sought-after Winter Springs High School district, this extraordinary property is within walking distance to quality schools and just minutes from shopping, dining, major highways, two golf courses, scenic bike trails, and Butterfly Park directly across the street. Rarely does a property combine nearly an acre of waterfront, a detached guest home, extensive updates, exceptional parking, workshop space, beautiful gardens, and an unbeatable location into one extraordinary offering. This is more than a home—it's a legacy property designed to bring generations together while offering the privacy, flexibility, and lifestyle today's buyers are searching for.

1048 Crystal Bowl Circle, Casselberry
$405,000
3 Beds ⋅ 2 Baths ⋅ Wil O' Wik SubDv. ⋅ 32707 Zip Code
Don’t miss this beautifully updated 3-bedroom, 2-bathroom home located in the highly desirable Wil O Wik neighborhood of Seminole County with $25K in UPGRADES! Tucked away on a quiet dead-end street and zoned for top-rated schools, this charming property offers the perfect blend of comfort, convenience, and style. The welcoming living room offers a cozy space to relax and unwind, while the sleek eat-in kitchen centrally located at the heart of the home boasts a newly renovated kitchen (2024) with soft close white shaker cabinets, granite countertops, a large deep stainless-steel sink & a spacious island with built-in storage ideal for cooking, dining and entertaining. Natural light fills the space through large windows, French doors, and sliding glass doors, creating a fresh and airy atmosphere throughout the main living areas. A generous dining space easily accommodates a large table, perfect for family meals or entertaining guests. The spacious primary suite boasts vaulted ceilings, views of the backyard, two walk-in closets, and a private en-suite bathroom with a walk-in shower. On the opposite side of the home are two additional bedrooms, a full guest bathroom, and a convenient laundry closet. The guest bathroom provides access to the screened-in lanai already “pool planned” and full of backyard potential. Step outside and enjoy Florida living year-round on the lanai, overlooking a fully fenced backyard with mature landscaping and plenty of room to relax, garden, or play. Recent updates include the freshly painted interior (2025), original Spanish tile flooring revealed and restored in living areas (2024), NEW waterproof luxury vinyl installed in the bedrooms (2024), Roof (2018) with NEW gutters (2024), and a NEW HVAC (2024). This home combines classic Florida charm with modern updates in a prime location just minutes from everything Orlando has to offer!

818 Wil O Wik Drive, Casselberry
$439,900
3 Beds ⋅ 2 Baths ⋅ Buttons Sub Amd SubDv. ⋅ 32707 Zip Code
BACK ON THE MARKET! Due to financing. Welcome to your beautifully remodeled pool home in the heart of Casselberry! Situated on an oversized 1/3-acre lot, this 3-bedroom, 2-bath residence offers the perfect blend of comfort, style, and privacy—with NO HOA. Step inside to find Pergo TimberCraft flooring flowing throughout the home, complemented by a warm and inviting family room featuring a wood-burning fireplace, rustic shiplap ceilings, surround sound speakers, and recessed lighting. French doors open seamlessly to your outdoor oasis, creating the perfect indoor-outdoor living experience. The updated kitchen is a true centerpiece, complete with a large island, quartz countertops, and sleek Samsung appliances—ideal for both everyday living and entertaining. The spacious primary suite includes a walk-in closet and a beautifully updated en suite bathroom, providing a private retreat. Enjoy Florida living at its finest with a screened-in pool, covered patios in both the front and back, and a fully fenced yard with a private entrance gate. The backyard also features a cozy fire pit area, perfect for relaxing or hosting gatherings. Additional highlights include a 2-car garage and ample outdoor space for recreation or storage. This move-in ready home checks all the boxes—modern updates, generous lot size, new roof in 2019, and a prime location close to shops, boutiques, restaurants, and entertainment. Don’t miss this opportunity!

1404 Beverly Lane, Casselberry
$459,000
4 Beds ⋅ 2 Baths ⋅ Sterling Oaks SubDv. ⋅ 32707 Zip Code
Just Reduced 10K! OPEN and spacious, this thoughtfully designed floor plan is perfect for entertaining. Brand NEW Energy Efficient 3.5 ton AC installed 6-26. with NEW Duct work. THIS IS A 4 BEDROOM HOME THAT WAS CONVERTED TO A 3 BEDROOM. IT CAN EASILY BE CONVERTED BACK. Volume ceilings and skylights fill the home with abundant natural light, while ceiling fans throughout provide comfort year-round. Elegant arched doorways add architectural charm and depth to each space. The large, chef-inspired kitchen is ideal for cooking and gathering, complemented by a gas range and gas water heater. Cozy evenings by the fireplace create a warm, inviting atmosphere. The home offers spacious bedrooms and updated master and guest bathrooms. Tile flooring runs throughout, and energy-efficient dual-pane windows provide added comfort and savings. Step outside to your private outdoor retreat featuring an extra-large screened-in porch, a fully fenced backyard, and a relaxing hot tub on the patio. Beautiful stone pavers enhance both the backyard and portions of the front exterior, adding style and durability. Additional features include a garage with a workbench and enclosed storage, with an oversized parking area, plus a full-size high-efficiency washer and dryer that convey with the home. NO HOA! This well-maintained property is a must-see—schedule your showing today.

1616 E Sandpiper Trail, Casselberry
$499,000
4 Beds ⋅ 3 Baths ⋅ A Rep Of A Pt Of Blk D Crystal Bowl Add SubDv. ⋅ 32707 Zip Code
Beautifully renovated and fully furnished, this versatile property presents a rare opportunity for those looking to establish an assisted living facility, group home, or residential care business — or, with simple modifications, can be converted back into a single-family residence. Set on an oversized 0.36-acre lot in a well-established Casselberry golf community, the home also offers a convenient Seminole County location for prospective clients and their families. Inside, the 4-bedroom, 3-bath layout delivers a bright, open feel with a functional split-bedroom floor plan built for comfort and privacy — a configuration equally suited to assisted living, group home use, residential care, or traditional single-family living. The updated kitchen shines with stainless steel appliances, abundant cabinetry, generous pantry storage, and expansive granite countertops — ideal for daily care operations or, just as easily, a busy family kitchen. Additional interior highlights include updated fixtures, generously sized living and dining areas, and a cozy fireplace in the main family room. The primary suite offers a private en-suite bath with granite vanity countertops and a double closet. Outside, the massive circular driveway provides ample parking, as well as a large screened patio, and spacious backyard offering room to relax, entertain, or expand. Just minutes from shopping, dining, parks, AdventHealth ER, and Oviedo Medical Center, this move-in-ready, turnkey property offers exceptional flexibility — whether as an income-ready care facility or a comfortable single-family home in one of Central Florida's most accessible and desirable areas.

78 S Winter Park Drive, Casselberry
$650,000
6 Beds ⋅ 5 Baths ⋅ Crystal Bowl Add SubDv. ⋅ 32707 Zip Code
Set on .79 acres with 75 feet of frontage on a peaceful non-motorized lake, this no-HOA property offers a private backyard setting with a swimming pool, oversized covered patio, and space for multigenerational living or rental potential. The main residence features 4 bedrooms, 3 full bathrooms, and approximately 2,300 square feet of living space designed around the lake and pool views. The remodeled kitchen opens to the dining and living areas and includes granite countertops, 42-inch cabinetry, built-in oven, and breakfast bar seating, creating a functional layout for both daily living and entertaining. Luxury vinyl flooring runs throughout the main living areas, with ceramic tile in bedrooms 3 and 4. The primary suite includes two walk-in closets, a garden bath, granite countertops, and a walk-in shower with multiple shower heads and rain shower feature. Bedroom 2 includes a private en suite bath with walk-in shower and granite countertop. Large sliding doors lead to the covered patio overlooking the pool and water. The detached two-story Additional Dwelling Unit (ADU) has its own private entrance and offers approximately 1,216 square feet of living space. Downstairs features a living area, open bedroom space, full bath with shower, and real hardwood flooring. Upstairs includes a second living area, full kitchen, bedroom, and half bath. The flexible layout is well suited for guests, extended family, home office space, or income-producing opportunities. Call today for your private showing!

1050 Crystal Bowl Circle, Casselberry
$464,900
3 Beds ⋅ 2 Baths ⋅ Howell Cove 4th Sec SubDv. ⋅ 32707 Zip Code
One or more photo(s) has been virtually staged. WELCOME-BIENVENIDO to HOWELL COVE! Do you have an RV or boat? This home offers a dedicated side parking area with a concrete pad and an accessible fence gate for extra convenience. This property features a NEW A/C (2026).Beautiful 3-bedroom, 2-bathroom home located in the Seminole County area!, fresh interior paint, and sits on a spacious 0.96-acre lot the property extends beyond the fence line and backs up to a conservation area and no rear neighbors, offering extra privacy, comfort, and peaceful views. The semi-circle driveway creates an elegant entrance while providing convenient easy-in/easy-out access without the need to reverse. As soon as you enter the home, you will notice the tile flooring throughout the entire house. The spacious living room features French doors leading to a screened patio and a huge deck overlooking the beautiful backyard. The fully remodeled kitchen with wood cabinets is perfect for hosting amazing dinners with family and friends. The garage has been freshly painted, including the floor. There is also a storage shed already waiting for you! Don’t wait too long! Schedule your private showing or tour today.

3633 Jericho Drive, Casselberry
$560,000
5 Beds ⋅ 3 Baths ⋅ Oakhurst Reserve Unit One SubDv. ⋅ 32707 Zip Code
Inside the gated community of Oakhurst Reserve, step into this inviting single-story home to discover a spacious open living-room and dining-room combo. The first hallway to the right leads to a large primary bedroom, with an attached bathroom and a large walk-in closet! Past the well-appointed kitchen, with ample cabinet space and modern appliances, is a second hallway to the right. This hallway leads down to three more rooms (two carpeted bedrooms, and the third bonus room), as well as a second full bathroom. Toward the back of the house is an additional entertainment room, which shares an open concept with the kitchen. Beyond that is a third hallway, with an additional two bedrooms and a third full bathroom. This addition makes the house ideal for multi-generational living. This home has many updates, including new windows throughout, flooring and screened in lanai all done in 2024. As well as a water heater installed in 2022, a roof in 2021, and a Lennox 23 SEER HVAC system in 2020, ensuring worry-free living for years to come. The fenced backyard offers privacy and space for outdoor activities, making it ideal for entertaining guests or simply relaxing in the sunshine. Furthermore, the property includes an 8x12 storage shed, offering 100sq/ft of storage space to keep all your lawn equipment neatly organized, ensuring that your garage remains free for parking your cars. The Rainsoft EC5 water treatment system, valued at approximately $7500, will remain with the house. This system provides added value and convenience for the new homeowners, ensuring clean and fresh water throughout the home. The home is only a few houses down the street from the beautiful community pool and playground.

1737 Setting Sun Loop, Casselberry