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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

$495,000
4 Beds 3 Baths Deer Run Unit 9a SubDv. 32707 Zip Code
The updates you'll notice are great. The ones you won't have to think about are even better. Here, the big-ticket items have already been taken care of. Roof replaced in 2024. Brand new HVAC in 2025. Renovated bathrooms. Updated kitchen. Fresh interior paint. And to top it off, the seller is paying off the solar panels at closing, so you'll get the benefit of lower electric bills without taking on a solar payment. Inside, you'll find four bedrooms, two and a half bathrooms, and over 2,100 square feet. The split-bedroom floor plan gives the primary suite a little separation from the secondary bedrooms, while the flex room near the front of the home can easily become a home office, playroom, workout space, or whatever fits your life. The kitchen opens to the main living areas, making it easy to stay connected whether you're cooking dinner, helping with homework, or catching up with friends. The primary suite is bigger than most, with sliding glass doors leading straight to the lanai, a beautifully updated bathroom with a large walk-in shower, and dual closets, giving you plenty of room without having to share every inch of storage. Out back is where this home really shines. The covered lanai is the kind of space you'll actually use, with skylights, ceiling fans, and a full outdoor kitchen complete with a built-in grill, refrigerator, prep space, and bar seating. Whether it's football on the TV, burgers on the grill, or everyone ending up outside after dinner, this is where people naturally gather. The pool screen enclosure was completely replaced including new hardware in 2025, giving the entire outdoor space a fresh, updated feel. There's plenty of deck space around the pool, and there's still fenced backyard beyond the enclosure, plus a storage shed for all the extras. Deer Run has been one of Casselberry's favorite neighborhoods for years, with mature trees, a low HOA, and nearly 140 acres of green space that's becoming a public park with walking trails. The neighborhood also provides direct access to the Casselberry Greenway Trail, giving you miles of paved trails right in your backyard. Just around the corner, you'll find the recently renovated Dew Drop Park with basketball, pickleball and tennis courts, a fishing dock, playground, and park. The elementary school is also just half a mile away. You're just minutes from Winter Park, Altamonte Springs, the 417, shopping, restaurants, and everything else that makes day-to-day life a little easier.

1539 Elf Stone Drive, Casselberry

$477,000
4 Beds 2 Baths Camelot Unit 2 SubDv. 32707 Zip Code
Welcome to this lovingly maintained, one-owner home offering an exceptional combination of quality updates, thoughtful features, and an unbeatable location in the heart of Casselberry. Major improvements provide peace of mind, including a new HVAC system (2025), new gas water heater (2026), new range, dishwasher, microwave, and garbage disposal (2026), roof replaced (2017), and exterior painted (2022). The home also features replacement windows with a lifetime warranty, hurricane shutters, a transferable termite bond, irrigation with reclaimed water, security system wiring, and natural gas service with a gas heat pump, gas water heater, and range. Inside, you'll find a cozy wood-burning fireplace and a versatile enclosed garage that could easily serve as a fifth bedroom, home office, or bonus room. One of the bathrooms offers direct access to the back porch, making it ideal as a future pool bath. The fully vinyl-fenced backyard includes a private rear gate providing direct access to the newly renovated Dew Drop Park, where you'll enjoy basketball and tennis courts, a playground, pavilion, dock, and open green space just steps from your backyard. This rare opportunity combines decades of meticulous ownership with outstanding updates and an incredible park-side setting that is difficult to find.

1391 Avalon Boulevard, 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

$340,000
4 Beds 3 Baths Seminole Sites SubDv. 32707 Zip Code
Welcome to this hidden gem in the heart of Casselberry! This charming 4-bedroom, 3-bathroom home offers a versatile layout designed for comfortable living. The private fourth bedroom features its own full bathroom, making it an ideal in-law suite, guest retreat, or private home office. The kitchen is equipped with beautiful granite countertops and provides a functional space for preparing meals and entertaining family and friends. Enjoy the added benefit of fully paid-off solar panels, helping reduce energy costs while increasing efficiency. Step outside to a spacious backyard with plenty of room for gardening, pets, play, or future outdoor entertaining. The covered back porch is the perfect place to unwind after a long day, enjoy your morning coffee, or relax on peaceful Florida evenings. Located in a desirable area with no HOA, this home offers the freedom and flexibility many buyers are looking for. Outdoor enthusiasts will appreciate being within walking distance of several Casselberry parks, including the popular skate park, playgrounds, walking trails, and recreational facilities. Conveniently situated just minutes from shopping centers, restaurants, schools, and major roadways, this home combines a quiet neighborhood feel with easy access to everything Central Florida has to offer. Don't miss this wonderful opportunity to own a move-in-ready home in one of Casselberry's most convenient locations. Schedule your private showing today!

825 Turtle Mound Drive, Casselberry

$295,000
3 Beds 3 Baths Summerhill Ph 2 SubDv. 32707 Zip Code
Virtually Staged. Welcome to this beautifully maintained 1,406-square-foot townhouse with 3 bedrooms and 2.5 bathrooms. Both bathrooms have been remodeled. Experience serene living with a truly low-maintenance lifestyle in the heart of Casselberry! Comfortable and Flexible are the words that best describe the layout. Located just a short walk to Red Bug Lake Park with tennis/basketball courts, soccer/baseball fields, and playgrounds, and zoned for top-rated Seminole County schools. Community amenities include a pool, a clubhouse, and well-maintained landscaping. Recent community upgrades include newly paved roads and an updated pool & clubhouse. Convenient to major roads, restaurants, and shopping. Centrally located near top-rated schools, Red Bug Lake Park, Altamonte & Oviedo Malls, I-4, 417, and more. Don’t miss this great opportunity—schedule your showing today!

2901 Wareham Court, Casselberry

$159,000
2 Beds 1 Baths Cabana Key A Condo SubDv. 32707 Zip Code
Enjoy living in this charming 2-bedroom, 1-bath first-floor condominium located in the desirable Cabana Key community. This well-maintained unit offers a screened patio perfect for relaxing, an interior laundry area, a spacious primary bedroom with a walk-in closet and separate vanity, plus an additional storage room for added convenience. Recent updates include newer windows, a new front door, a replaced patio screen, and updated flooring installed approximately one year ago. Residents of Cabana Key enjoy access to a community pool, spa, and clubhouse, creating the perfect setting for both relaxation and recreation. This home also offers convenient access to shopping, dining, and everyday essentials. Whether you're looking for a primary residence, vacation getaway, or investment opportunity, this move-in-ready condo offers comfort, and convenience.

3756 Idlebrook Circle Unit 108, Casselberry

$269,900
2 Beds 3 Baths Summerhill Ph 2 SubDv. 32707 Zip Code
Virtually Staged. Welcome to 2889 Wareham Court, a beautifully updated townhome offering modern finishes, spacious living areas, and an exceptional location. This move-in ready home has been completely renovated with new kitchen cabinetry, quartz countertops, stainless steel appliances including a stove, dishwasher, disposal, and refrigerator, as well as new sinks and faucets throughout. Additional updates include remodeled bathrooms with quartz-topped vanities, luxury vinyl plank flooring, new carpet, and a new water heater. The open-concept floor plan features a large living room, dining area, convenient downstairs powder room, and a fully remodeled kitchen with an inside laundry closet for added convenience. Sliding glass doors lead from the dining area to a private patio and oversized backyard space, a rare benefit in townhome living. An exterior storage closet provides additional room for seasonal items and outdoor equipment. Upstairs, you'll find two generously sized bedrooms, each with its own full bathroom and large closet, making either room an ideal primary suite. Residents enjoy access to a community pool and beautifully landscaped grounds. Located in the heart of Seminole County, this home is zoned for top-rated Seminole County schools and is conveniently close to shopping, restaurants, parks, and major roadways. Don't miss this opportunity to own a fully updated townhome in one of Central Florida's most desirable locations. Some photos have been Virtually Staged.

2889 Wareham Court, Casselberry

$405,000
4 Beds 2 Baths Sterling Park SubDv. 32707 Zip Code
This is a rare opportunity to own a Large 4 bedroom 2 bath home inside the quiet neighborhood of Deer Run / Sterling Park Community, only minutes to Maitland, Altamonte Springs Winter Park and downtown Orlando. As you enter, you'll immediately notice the soaring ceilings in the spacious living and dining areas, along with the oversized pass-through breakfast bar that connects the kitchen to the formal dining room. All bedrooms are generously sized, especially the primary suite, which features a large vanity and a separate glass-enclosed shower. Newer luxury vinyl plank flooring extends throughout several of the bedrooms, while tile flooring leads from the entryway through the kitchen and informal dining area—meaning there is no carpet anywhere in the home. The kitchen offers abundant cabinet and counter space, a large walk-in pantry, and newer stainless steel appliances. Just beyond the Living room, a 20-foot screened porch provides the perfect setting for morning coffee, outdoor dining, and weekend grilling. Storage is plentiful with an attic access stairwell, built-in garage shelving plus workbench and a 12' x 10' aluminum shed that can easily accommodate tools, equipment, and outdoor gear. Recent updates include: * High-efficiency Carrier A/C system (less than 5 years old) * Side-by-side refrigerator with ice and water dispenser in the door (less than 2 years old) * Newer shingle roof (2021) * Luxury vinyl flooring (2022) * All new exterior paint (2026) * Washer and Dryer * Paddle fans throughout Residents of Sterling Park enjoy access to a community picnic and playground area, a secure swimming pool, and a basketball court. Future recreational opportunities are on the horizon as the former Deer Run Golf Course is being transformed into The Deer Run Community Park. Planned amenities include more than four miles of trails and boardwalks, along with a renovated community center, creating an exceptional outdoor destination within Seminole County's natural landscape. All schools are close by and Sterling Park Elementary is inside the neighborhood for easy access. Make your appointment to see this today!

298 Quail Court, Casselberry

$285,000
3 Beds 1 Baths Heftler Homes Orlando Section One SubDv. 32707 Zip Code
This cozy updated home is back on the market! Previous Buyer’s Inspection and appraisal went well — they had to cancel due to personal reasons. This CONCRETE BLOCK single family home on a SPACIOUS 0.18 ACRE LOT in a truly central location! The home features a carport for convenient covered parking, which also doubles as a covered porch space to enjoy the outdoors. The covered carport is an excellent set up for enclosing it in the future to add additional flex space! With NO HOA, you’ll appreciate the freedom to make the property work for your lifestyle, along with plenty of flexible parking. The comfortable interior layout flows easily from the living space into the dining area and the fully UPDATED KITCHEN with newer appliances. Down the hallway, you’ll find 3 bedrooms and a RENOVATED BATHROOM with a fresh, modern design that ties the home together. Main systems are already taken care of with UPDATED ELECTRICAL, NEWER HVAC (2022), WATER HEATER (2020), and RAIN GUTTERS upgraded with leaf filters. Roof (2013) is still in great shape. SLIDING GLASS DOOR in the living room was replaced in 2023, plus Washer and Dryer are included! Enjoy the LARGE BACKYARD equipped with a spacious STORAGE SHED. With a PRIME LOCATION, you’re just a 10–15 minute drive to Winter Park, Maitland, Tuskawilla, Winter Springs, and Altamonte Springs, with quick access to shopping, dining, parks, and everyday conveniences. TO SEE MORE OF THE HOUSE, WATCH THE VIDEO/VIRTUAL TOUR!

205 Wilshire Drive, Casselberry

$375,000
3 Beds 2 Baths Sterling Park SubDv. 32707 Zip Code
WELCOME HOME to this charming single-family house in the desirable Sterling Park Community which is centrally located close to UCF, Full Sail, Rollins College and Winter Park. This home offers 3 bedrooms and 2 bathrooms. A large spacious eat-in kitchen, along with a sizable Great Room with vaulted ceilings! The Great Room includes a wood burning fireplace as a focal point, ranging the full height of the vaulted ceiling. Ceramic tile covers the living area, kitchen and bathrooms. There is new carpet in the bedrooms. The entire inside of the home has been freshly painted a nice neutral color for its new owners! Newer Roof was installed in 2018. New Garage Door motor 2025. There is a screened in porch to enjoy fresh air with your morning coffee! The large backyard is a clean slate! You have plenty of room! In fact, you have room to add a pool and will still have yard available for your family and/or pets to play! This home is a clean slate! You have the opportunity to put your own stamp on it, making it your own! It is located just minutes from shopping, dining and major highways! No matter what you need, it is close by!

309 Redwing Way, Casselberry

$499,000
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

$230,000
2 Beds 2 Baths Deer Run Unit 14a SubDv. 32707 Zip Code
Discover this beautifully maintained 2-bedroom, 2-bath Townhouse with a spacious loft, perfectly located at 4004 Crosswords Place in Casselberry, Florida. This inviting property features an updated kitchen and stunning brand-new luxury vinyl flooring throughout, offering a modern and move-in-ready feel. Nestled in a quiet, established neighborhood, residents enjoy access to fantastic community amenities including a swimming pool, tennis courts, and relaxing outdoor patio area—perfect for both everyday living and entertaining or just relaxing. Conveniently located near medical facilities, shopping and the Orlando International airport. this home combines comfort, convenience, and lifestyle in one ideal package. Whether you are a first homebuyer or just looking to retire and enjoy a great neighborhood. Don’t miss your opportunity to call this home—schedule your showing today! some of the pictures are virtually staged, to provide you with an awesome perspective

4004 Crossroads Place, Casselberry

$169,900
2 Beds 2 Baths Oxford Square Condo SubDv. 32707 Zip Code
Virtually Staged. Special incentive of $5000 closing costs for buyers—ask for more info! Beautifully maintained and thoughtfully updated 2-bedroom, 2-bath first-floor condo in the Oxford Square community of Casselberry. This move-in-ready unit features a highly functional layout with both bedrooms offering en-suite bathrooms, creating two private suites—ideal for roommates, guests, or flexible living arrangements. This unit also features convenient IN-UNIT LAUNDRY. The interior has been extensively updated with quartz countertops, washed-oak luxury flooring, updated carpet, refreshed bathroom cabinetry, and modern light and plumbing fixtures throughout. Both toilets have been replaced, and the home has been meticulously cared for. Enjoy a private porch, comfortable living space, and added peace of mind with a SimpliSafe security system. A major exterior upgrade includes a brand-new roof installed by the association in late 2025, contributing to long-term value and reduced maintenance concerns. With a low-maintenance lifestyle, functional layout, and versatility for different living needs, this property is well-suited for both personal use and long-term ownership goals.

612 Kenwick Circle Unit 103, Casselberry