Homes for Sale Near Winter Springs High in Casselberry - 22 homes

Remarks: NEWLY UPDATED 1 BEDROOM 1 BATH IN CASSELBERRY, MOVE-IN READY. BUILDINGS ARE ALL ONE STORY WITH NO NEIGHBORS ABOVE. NEWER A/C. ROOF WAS PUT ON 2022. HOME IS IN LAKE KATHRYN VILLAGE CONDOS ON LAKE KATHRYN. ALL NEW WINDOWS AND NEW DOORS. LAKE ACCESS WITH A PRIVATE DOCK AND BOAT LAUNCH. HOA IS 370.00 A MONTH INCLUDES WATER/SEWER, GARBAGE AND WASHER & DRYER. LAUNDRY IS ONLY SHARED BY 4 UNITS RIGHT OUTSIDE YOUR BACK DOOR. PARKING IN FRONT OF UNIT AND VISTOR PARKING IS AROUND THE CORNER. COMMON RECREATIONAL AREA FOR PARTIES AND GRILLING OUT. BUYER MUST BE APPROVED BY THE HOA. GREAT FOR HOMEOWNERSHIP OR INVESTMENT AS LEASING IS ALLOWED. SELLER WILL ASSIST WITH CLOSING COSTS.

Listing is courtesy of: RICHLAND PROPERTIES (352-516-4574)

Listing Agent: Stacey Richard (352-516-4574)

Remarks: One or more photo(s) has been virtually staged. Short Sale. Short Sale – Stunning Turn-Key Home in Desirable Seminole County Don’t miss this incredible opportunity to own a beautifully maintained 4-bedroom, 3.5-bath home built in 2013, offering 2,148 heated square feet and 2,768 total square feet of thoughtfully designed living space. From the moment you enter, you’ll appreciate the open and inviting layout complemented by elegant tile flooring throughout the main living areas. The spacious primary suite is a true retreat, featuring a custom-built closet designed for both style and functionality. The two-story floor plan provides 940 square feet on the first level and 1,208 square feet upstairs, creating a seamless flow with ample room for everyday living and entertaining. Enjoy outdoor relaxation on the finished/open porch, plus the convenience of a 400 sq ft attached garage. Situated on a 5,724 sq ft lot in highly sought-after Seminole County, this home offers comfort, quality, and location all in one. Short sale – lender approval required. A rare chance to secure exceptional value in a prime area.

Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)

Listing Agent: Fina Perez (407-780-6680)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. **Seller may consider buyer concessions if made in an offer**Welcome to this BEAUTIFULLY UPDATED 4-bedroom, 3.5-bath townhome in the desirable Legacy Park community of Casselberry, offering over 2,200 SQUARE FEET of thoughtfully designed living space—an incredible value for the size and location. From the moment you arrive, the home impresses with its CHARMING CURB APPEAL, manicured landscaping, and a brick paver walkway that leads to the inviting front entrance. Inside, you’ll find LUXURY VINYL PLANK FLOORING throughout all three levels, creating a cohesive and modern feel. The first floor features a private bedroom with its own EN SUITE BATH, making it ideal for guests, a home office, or a COMFORTABLE IN-LAW SUITE. Upstairs on the second level, the main living space is BRIGHT, OPEN, and perfect for both everyday living and entertaining. The Living Room, Dining area, and Kitchen flow seamlessly together, enhanced by ABUNDANT NATURAL LIGHT. The Kitchen is well-appointed with 42” cabinetry, STONE COUNTERTOPS, stainless steel appliances, a tile backsplash, a pantry closet, and a breakfast bar, along with a PASS-THROUGH to the Dining Room for added convenience. From the Dining area, step out through a glass-paneled door that opens to a PRIVATE BALCONY, offering a lovely spot to enjoy fresh air and quiet moments. The third floor is dedicated to restful retreats, including the SPACIOUS Primary Suite with a large walk-in closet and an EN SUITE BATH featuring dual sinks, stone countertops, and a garden tub/shower combination. Two additional bedrooms, a full bath, and a convenient LAUNDRY CLOSET complete the upper level. Additional highlights include a 2-car rear-entry garage, a NEWER ROOF (4 years old), and recent HOA-COMPLETED BUILDING REPAIRS, offering peace of mind and long-term value. Residents of Legacy Park enjoy access to COMMUNITY AMENITIES including a sparkling pool and playground, all within a WELL-MAINTAINED NEIGHBORHOOD. Ideally located in Casselberry, this home offers CONVENIENT ACCESS to shopping, dining, and outdoor recreation. Enjoy NEARBY DESTINATIONS like Secret Lake Park and Lake Concord Park, or explore the shops and restaurants of WINTER PARK. With easy access to major roadways and a short drive to Orlando, commuting and entertainment are always within reach. Its GENEROUS LIVING SPACE, modern updates, and PRIME LOCATION make this Legacy Park townhome the perfect blend of space, style, and LOW-MAINTENANCE LIVING. Make this one yours before its gone!

Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)

Listing Agent: Jenny Wemert (407-809-1193)

Remarks: Excellent investment opportunity in Casselberry. This well-maintained 1-bedroom, 1-bath property is currently leased month-to-month, providing immediate and flexible rental income. With a functional layout, solid condition, and strong demand in the area, it offers dependable performance and long-term appreciation potential. A great addition to any investment portfolio.

Listing is courtesy of: LA ROSA REALTY KISSIMMEE (407-930-3530)

Listing Agent: Barbas Barbastefano (347-575-5536)

Remarks: *NEW CONSTRUCTION* - Welcome to the CARLISLE FLOOR PLAN, a *4 BED / 2 FULL BATH / 1 HALF BATH* Single Family Home located in the sought after community GREENVILLE COMMONS, in Casselberry - FL, served by Seminole County great schools. THIS HOME is part of the 2nd and final phase of the community development. Greenville Commons consists of a total of 41 single family homes and it's on its last phase to completion. Filled with natural light, the CARLISLE FLOOR PLAN offers over 2,300 heated SqFt of ample spaces in an open and modern design, tile floorings throughout all living spaces on MAIN LEVEL is a pre-selected UPGRADE, already included on listing price. The KITCHEN will feature QUARTZ COUNTERTOPS, 42" UPPER CABINETRY, APPLIANCES such as refrigerator, microwave, dishwasher and range, dual sink island and backsplash. The Kitchen is adjacent to the DINNING AREA and flows into the family/gathering room, with sliding doors to the covered oversized LANAI. Going up to the second floor, the OWNER'S SUITE features 2 spacious walk-in closets, dual vanity and stand-up shower with enclosure. BEDROOMS 2, 3 and 4 share BATHROOM 2, featuring dual vanity, quartz countertops and bath tub. Laundry is conveniently located on the second floor. The community is located almost across from The Geneva School, a prime location in Casselberry, within minutes from DOWNTOWN ORLANDO and all major roads, highways, shoppings, restaurants and entertainment. The community offers a playground, dog park and pond view.

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Emidio Dias Carvalho Neto, Llc (407-341-6611)

Remarks: Welcome to the CARLISLE FLOOR PLAN, a *4 BED / 2 FULL BATH / 1 HALF BATH* Single Family Home located in the sought after community GREENVILLE COMMONS, in Casselberry - FL, served by Seminole County great schools. THIS HOME is part of the 2nd and final phase of the community development. Greenville Commons consists of a total of 41 single family homes and it's on its last phase to completion. Filled with natural light, the CARLISLE FLOOR PLAN offers over 2,300 heated SqFt of ample spaces in an open and modern design, tile floorings throughout all living spaces on MAIN LEVEL is a pre-selected UPGRADE, already included on listing price. The KITCHEN will feature QUARTZ COUNTERTOPS, 42" UPPER CABINETRY, APPLIANCES such as refrigerator, microwave, dishwasher and range, dual sink island and backsplash. The Kitchen is adjacent to the DINNING AREA and flows into the family/gathering room, with sliding doors to the covered oversized LANAI. Going up to the second floor, the OWNER'S SUITE features 2 spacious walk-in closets, dual vanity and stand-up shower with enclosure. BEDROOMS 2, 3 and 4 share BATHROOM 2, featuring dual vanity, quartz countertops and bath tub. Laundry is conveniently located on the second floor. The community is located almost across from The Geneva School, a prime location in Casselberry, within minutes from DOWNTOWN ORLANDO and all major roads, highways, shoppings, restaurants and entertainment. The community offers a playground, dog park and pond view.

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Emidio Dias Carvalho Neto, Llc (407-341-6611)

Remarks: Welcome to the CARLISLE FLOOR PLAN, a *4 BED / 2 FULL BATH / 1 HALF BATH* Single Family Home located in the sought after community GREENVILLE COMMONS, in Casselberry - FL, served by Seminole County great schools. THIS HOME is part of the 2nd and final phase of the community development. Greenville Commons consists of a total of 41 single family homes and it's on its last phase to completion. Filled with natural light, the CARLISLE FLOOR PLAN offers over 2,300 heated SqFt of ample spaces in an open and modern design, tile floorings throughout all living spaces on MAIN LEVEL is a pre-selected UPGRADE, already included on listing price. The KITCHEN will feature QUARTZ COUNTERTOPS, 42" UPPER CABINETRY, APPLIANCES such as refrigerator, microwave, dishwasher and range, dual sink island and backsplash. The Kitchen is adjacent to the DINNING AREA and flows into the family/gathering room, with sliding doors to the covered oversized LANAI. Going up to the second floor, the OWNER'S SUITE features 2 spacious walk-in closets, dual vanity and stand-up shower with enclosure. BEDROOMS 2, 3 and 4 share BATHROOM 2, featuring dual vanity, quartz countertops and bath tub. Laundry is conveniently located on the second floor. The community is located almost across from The Geneva School, a prime location in Casselberry, within minutes from DOWNTOWN ORLANDO and all major roads, highways, shoppings, restaurants and entertainment. The community offers a playground, dog park and pond view.

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Emidio Dias Carvalho Neto, Llc (407-341-6611)

Remarks: Welcome home to this beautifully maintained 3-bedroom, 2.5-bathroom townhome located in the desirable Legacy Park community! From the moment you step through the front door, you’ll appreciate the warm and inviting layout designed to make you feel right at home. The first floor features a spacious living area that flows seamlessly into the kitchen, complete with a breakfast bar perfect for bar stools and gathering with family and friends. The kitchen offers granite countertops, stainless steel appliances, dark wood cabinetry, a pantry, and direct access to the spacious 2-car garage. Upstairs, you’re welcomed by a versatile landing area ideal for a cozy reading nook or small flex space, leading into the thoughtfully designed split floor plan. The spacious primary suite features a walk-in closet and a private ensuite bathroom with a soaking tub, separate stand-up shower, and double sink vanity. Across the landing, you’ll find two generously sized guest bedrooms along with a full guest bathroom. The rear-entry 2-car garage provides plenty of parking, while additional designated guest parking is conveniently located nearby. Residents of Legacy Park enjoy access to community amenities including a pool, playground, walking trail, and scenic lake just minutes from your front door. Ideally situated with easy access to major highways, shopping, dining, and top-rated Seminole County Public Schools, this home offers both comfort and convenience. Schedule your private showing today!

Listing is courtesy of: MARKET CONNECT REALTY LLC (407-250-4708)

Listing Agent: Ayoub Seffari (407-497-4015)

Remarks: Welcome to this inviting 3-bedroom, 2.5-bath home in the heart of Casselberry. Nestled in a charming, quiet neighborhood, this property offers the perfect blend of comfort, convenience, and location. Enjoy being just a short walk to Foxtail Coffee Co. and only minutes from everyday essentials like Publix, with quick access to 434 and the 417 for easy commuting throughout Central Florida. Inside, you’ll find a functional, well-designed layout with spacious living areas, comfortable bedrooms, and plenty of room for both relaxing and entertaining. Offering low-maintenance living in a well-connected area, this home has been consistently occupied by tenants since it was built—making it not only a solid investment opportunity but also an excellent choice for your next home.

Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)

Listing Agent: Allie George (407-457-4815)

Remarks: Welcome to this beautifully maintained 4-bedroom, 3.5-bathroom home in the heart of Casselberry. Built in 2021, this two-story residence offers modern finishes, thoughtful design, and an abundance of space for comfortable living. Nestled in a charming and quiet neighborhood, it’s just a short walk to Foxtail Coffee Co. and minutes from popular shopping and dining options like Publix, with convenient access to 434 and the 417. Inside, you’ll enjoy spacious living areas, a functional two-story layout, and generously sized bedrooms. With consistent tenant occupancy since its construction, this property presents a fantastic investment opportunity—or the perfect place to make your next home.

Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)

Listing Agent: Allie George (407-457-4815)

Remarks: Under contract-accepting backup offers. Welcome to 1375 Lake Drive in Casselberry, a beautifully fully remodeled 4-bedroom, 3-bathroom, plus a office home that is truly move-in ready from top to bottom. Thoughtfully updated with modern finishes and a functional layout, this home offers the perfect opportunity for first-time buyers or anyone looking for a stylish, turnkey property. Perfect for a growing family with a specific budget in mind or an investor looking for a pad-split. Inside, you’ll find a bright and inviting interior with fresh paint throughout, recessed lighting, and a spacious layout designed for comfortable everyday living. The main living room flows effortlessly into the dining area and kitchen, creating a natural gathering space for family and friends. The completely redesigned kitchen features all-new stainless steel appliances, sleek new cabinetry, new countertops, and elegant brass finishes that give the space a modern, polished look. The home offers two separate living rooms, providing flexibility for entertaining, relaxing, or creating a dedicated media or play space. In addition to the three bedrooms and three full bathrooms, there are two bonus rooms that can easily serve as a home office, study, gym, or hobby space depending on your needs. Located in the heart of Casselberry, this home places you close to everything that makes the area special. Enjoy nearby outdoor destinations such as Secret Lake Park, Lake Concord Park, and the Casselberry Greenway Trail for walking, biking, and weekend recreation. The home is also conveniently located near Red Bug Lake Park, local shopping centers, restaurants, and entertainment options, with easy access to SR 436, SR 17-92, and nearby Winter Park and Altamonte Springs. With its modern, professional renovation done by Iron House Florida LLC, a local Central Florida investor, flexible layout, and convenient location, 1375 Lake Drive is an ideal starter home that allows you to move in, settle down, and start enjoying your new space immediately.

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Abby Greenberg (407-484-2689)

Remarks: Under contract-accepting backup offers. Under contract-accepting backup offers. Multiple Offers..Highest and best by 5:00p.m. Mon. May 18th Discover and enjoy this GREAT VALUE at 1434 Lakeshore Drive, Casselberry! This spacious 4-Bedroom, 2-Bath Pool Home sits on quarter-acre lot with NO HOA, giving you the freedom to bring all your toys: Boats, Jet Skis, Trailers, RVs, and more! Property also has Walk-In Storage Shed/Shop, extra Concrete Parking Areas, Wood Fenced Yard with Access Gates, Fire Pit Area and New Air Conditioning System. Enjoy Florida living with your own Above-ground Pool and Screened Patio; perfect for relaxing and entertaining. Inside, you'll find large Wood Kitchen with Stainless Steel Appliances & Sink, comfortable living spaces with Cathedral Ceilings & Luxury Vinyl and laminate Floors with plenty of room for family and guests. Located in a highly desired school district and close to dining, shopping and major roadways, this home offers the perfect combination of space, convenience, and flexibility. Don't miss this unusual opportunity to have it all at a GREAT PRICE.

Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)

Listing Agent: Dawn Taylor (407-929-1958)

Remarks: One or more photo(s) has been virtually staged. Welcome to this Casselberry home offering a comfortable layout and a convenient Central Florida location. Inside, you’ll find spacious living areas, well-sized bedrooms, and a functional kitchen with ample cabinet and counter space. The home features a natural flow throughout with plenty of room for everyday living, relaxing, or entertaining guests. Enjoy the outdoor space ideal for gatherings, gardening, or creating your own private retreat. Conveniently located near shopping, dining, parks, major roadways, and local attractions, this property provides easy access to both Orlando and the surrounding communities.

Listing is courtesy of: MAINSTAY BROKERAGE LLC (800-583-2914)

Listing Agent: Raquel Littlejohn (470-279-6333)

Remarks: One or more photo(s) has been virtually staged. Stunning 4 Bed rooms and 3 Baths, home in beautiful Gated Community Near Geneva School in Casselberry. Welcome to this beautifully maintained single-family home featuring 4 spacious bedrooms and 3 full bathrooms and spacious Patio, perfectly located in one of the area’s most desirable gated communities — just behind Geneva School. One of the home’s most desirable features is the convenient first-floor bedroom and full bathroom, making it ideal for elderly family members, guests, or families with small children. Designed for both comfort and entertaining, this home offers: Spacious 2-car garage Expansive 30x15 covered patio with a fully built-in outdoor kitchen Private backyard oasis filled with mature fruit trees including mango, sapodilla, fig, peach, lemon, sugar apple, and moringa Enjoy peaceful mornings and relaxing evenings in a community known for its beauty and family-friendly atmosphere. Residents love the scenic lake with walking paths, resort-style pool, playground, and dog park. Additional highlights: Excellent schools nearby Convenient access to Hwy 17-92 and State Road 434 Close to shopping, dining, and everyday conveniences Secure gated entrance and beautifully maintained surroundings This home offers the perfect combination of privacy, comfort, nature, and convenience. Whether you love entertaining outdoors, gardening, or simply enjoying a peaceful neighborhood, this property has it all. Showings are done by appointments only as the property is occupied by Tenants. Furniture is not included in the sale. Reach out to the agent if you have any questions. Come & see this exceptional home today — you will fall in love!

Listing is courtesy of: BLISSFUL REAL ESTATE LLC (407-867-0007)

Listing Agent: Radhakrishna Yerra (689-291-5072)

Remarks: One or more photo(s) has been virtually staged. Welcome to 1262 Seminola Blvd. , a beautifully renovated home featuring modern finishes throughout. This move in ready home offers a brand new kitchen with NEW APPLIANCE, stylish new bathrooms, new LVP flooring, freshly painted inside and out, and even a brand new ROOF, brand new HVAC and brand new WATER HEATHER! Every detail has been thoughtfully updated for comfort and style. This home is ready for the pickiest buyer and easy to show.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Betul Akman (737-500-2120)

Remarks: Under contract-accepting backup offers. Welcome to this meticulously kept three-story townhome located in the desirable Legacy Park community in Casselberry! Offering the perfect blend of space, style, and convenience, this home features a flexible floorplan with a spacious guest suite on the main level — ideal for visitors, a home office, or multigenerational living. Upstairs, you’ll love the open-concept living spaces accented by newer engineered hardwood floors and abundant natural light. The kitchen has been thoughtfully refreshed with appliances replaced in 2024, creating a modern and functional space for everyday living and entertaining. A standout feature is the custom built-in bar area, adding character and the perfect spot to host friends and family. Step outside to the oversized balcony, ideal for enjoying your morning coffee or relaxing in the evenings. This meticulously maintained home also offers valuable updates including a 2022 roof and 2023 A/C for added peace of mind. The spacious two-car garage provides ample parking and storage space. Legacy Park residents enjoy access to wonderful community amenities including a resort-style pool and neighborhood park/playground area. Conveniently located near shopping, dining, Seminole County parks, and major roadways including 17-92 and SR-417, this location makes commuting to Orlando, Winter Park, and surrounding areas a breeze. This move-in ready home truly offers low-maintenance living with all the space and upgrades you’ve been looking for!

Listing is courtesy of: ALL REAL ESTATE & INVESTMENTS (407-917-8206)

Listing Agent: Amy Miller (407-917-8206)

Remarks: 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!

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Jenn Carlisle (407-617-5597)

Remarks: This well-maintained single-family home offers comfortable, low-maintenance living with 3 bedrooms and 2 full baths in a functional split-bedroom floor plan. Lovingly cared for by the same owner for 51 years, the home reflects true pride of ownership throughout. Enjoy a large fenced yard with plenty of space to relax, garden, or entertain—all with no HOA restrictions. Major updates include a 2021 roof, 2018 AC, and 2023 water heater, providing peace of mind for the next owner. Additional features include an inside laundry room and access to highly regarded Seminole County schools. Move-in ready as is, with the opportunity to make simple updates over time to suit your style. A great option for first-time buyers or those looking to downsize and enjoy a more relaxed lifestyle.

Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)

Listing Agent: Brad Merrell (407-920-7800)

Remarks: Under contract-accepting backup offers. Rare affordability! Introducing Antigua Bay, a small desirable community in desirable Casselberry, with easy access to shopping and all major highways tucked between Winter Park and Longwood. This large 3 bedroom 2 1/2 bath townhome offers a 2-car attached garage with remote opener for easy access. Brick paver driveway and decorator paint interior, Carpet replaced last year and all appliances to include a full size washer and dryer conveniently located on the 2nd floor. Double door entry into a large primary suite with a generous walk-in closet and private en-suite bath. Two other large bedrooms share a 2nd bath plus a powder room on the first level. Formal dining room and living room with sliding glass doors to your patio. You'll want to see this before it is gone.

Listing is courtesy of: CLAIRE SCHWARTZ & ASSOCIATES (407-352-5244)

Listing Agent: Claire Schwartz (321-439-6995)

Remarks: Welcome to 800 Diane Dr. — a beautifully updated corner-lot home perfect for families and first-time buyers. This warm and inviting property features a brand-new kitchen with modern finishes, new flooring throughout, and updated windows that fill the home with natural light. Three majestic live oak trees frame the property, adding timeless beauty, shade, and curb appeal. The open layout provides plenty of space for gathering and everyday living, while the large corner lot offers room for play, pets, or outdoor entertaining. Conveniently located near parks, schools, shopping, and dining, this move-in-ready Casselberry home is the perfect place to start your next chapter.

Listing is courtesy of: WESTIN REALTY GROUP (407-782-7799)

Listing Agent: Michael Mullvain (407-782-7799)