Homes for Sale Near Winter Springs High in Casselberry - 11 homes

Remarks: Welcome to this move-in ready four bedroom, three full bathroom residence situated in the highly sought-after Legacy Park community of Seminole County. The interior offers a spacious open concept floor plan that seamlessly connects the living and dining areas to a well-appointed kitchen featuring 42-inch cabinetry, granite countertops, tile backsplash, closet pantry, and a convenient breakfast bar. The main level includes a generous secondary bedroom and a full bathroom, providing flexibility for guests or a home office. Upstairs you will find a versatile loft space alongside three additional bedrooms and a large laundry room. The entire upper level is finished with luxury vinyl plank flooring, ensuring a carpet-free environment throughout the home. The primary suite serves as a private retreat with its own en-suite bathroom and a sizeable walk-in closet. Outside, the lush backyard is fully fenced and features a manicured lawn and a custom fire pit area designed for relaxation. Recent mechanical upgrades include an HVAC system replaced within the last two years, and the property will feature a brand-new roof installed prior to closing. This home is located just minutes from premium shopping and dining districts, offering a perfect blend of comfort and convenience in a premier Central Florida location.

Listing is courtesy of: BHHS FLORIDA REALTY (407-406-5300)

Listing Agent: Troy Hensley (407-406-5300)

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. This Casselberry home has been thoughtfully updated and is truly turn-key! 3 bedrooms, 2.5 bathrooms, over 1800sqft of living space, a loft upstairs, and a screened-in patio overlooking your fully fenced-in backyard with gorgeous oak trees. Legacy Park is a newer neighborhood known for its community atmosphere and amenities, including a beautiful pool. Casselberry is backed by the highly rated Seminole County School District and this home sits directly across the street from The Geneva School. The first floor features upgraded tile throughout, an open floor plan, a half bathroom for guests, and laundry room. The kitchen features a wine cooler, granite counter tops, backsplash, and solid wood cabinetry. The home is equipped with a Nest thermostat, helping maximize energy efficiency and reduce utility costs. Upstairs you'll find the Master Bedroom with tray ceilings, his and hers sinks, and a spacious walk-in closet with upgraded shelving. There are two additional bedrooms- one with a charming accent wall, the other a clean canvas. The two bedrooms share a full-bathroom. The loft area is flexible and could make for a great office or play space. You’ll be just minutes from the desirable Winter Springs, Casselberry’s well loved Secret Lake Park, and the city's newest addition Wheels Park, a world-class public skate park. No detail has been missed in this home from the floors, the lighting, and bathrooms. Don't miss your opportunity to make this tastefully updated Casselberry home yours!

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Ken Pozek (407-813-2773)

Remarks: Under contract-accepting backup offers. Welcome to 1044 Osceola Trail — a spacious 3 bedroom, 2 bath, 1,512 sq ft double-wide manufactured home offering a rare combination of space, upgrades, and functionality in a prime Casselberry location that is convenient to Altamonte Springs, Maitland, and I-4. Step inside to an inviting open-concept layout featuring tray ceilings in both the living and dining areas, enhanced with crown molding that continues through the living room, kitchen, and dining space. Luxury vinyl plank flooring flows throughout the living room, kitchen, laundry room, dining area, and hallways, creating a modern and cohesive feel. The kitchen is designed for both function and style with a large 4x7 center island that offers plenty of storage, and a hidden walk-in pantry, providing additional ,exceptional storage. The Frigidaire refrigerator and Whirlpool microwave are both less than one year old. The split floor plan offers added privacy, with a spacious primary suite featuring dual vanities, a corner garden tub with a large window for natural light, a separate shower stall with rain shower head, and additional built-in storage cabinetry. Accessible from both the primary bathroom and kitchen is the laundry room that features included washer, dryer, shelving , and an additional wall mounted cabinet for even more storage! The laundry room also features an access door leading to the large, screened back porch and can act as mudroom as well. Outdoor living is a standout feature with a large screened-in back porch boasting 10-foot ceilings and a summer sink, perfect for entertaining. The backyard includes an additional concrete patio pad, storage shed, and is fully fenced. The front yard is accented by a white picket fence for added curb appeal. Additional features include a new A/C unit with heat pump installed approximately 2 months ago, roof and water heater both 2018, attic exhaust fan, irrigation system, storm glass front door, Ring Doorbell, washer and dryer included, and window blinds throughout. The property also offers a single car carport with an extended driveway that can accommodate up to four vehicles. Conveniently located near shopping, dining, and major roadways, with easy access to Winter Springs and Altamonte Springs. Seller offering a $10,000 buyer credit — significantly reducing out-of-pocket costs and creating an opportunity to buy down your interest rate, cover closing costs, or customize the home to your liking. Move-in ready with major systems already updated, this home offers exceptional value and functionality

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

Listing Agent: Victoria Mccray (407-342-3807)

Remarks: 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: This offering presents a rare opportunity to acquire a 4-unit income-producing property in the highly sought-after Casselberry submarket of the Orlando MSA. Situated on an expansive 0.85-acre parcel, the property consists of four detached rental homes with durable masonry construction, newer roofs (approximately 4 years old), and a strong history of occupancy. The asset provides stable in-place income with a current rent roll of approximately $71K annually, while offering clear value-add potential through rent growth. Current average rents are below market at approximately $1,650 per unit, with comparable properties supporting higher rent rate per unit, creating a straightforward path to increase income and overall asset value. Operationally, the property benefits from favorable insurance costs (~$6K/year) and minimal near-term capital expenditure requirements, making it a low-risk, easy-to-manage investment. The combination of strong fundamentals, below-market rents, and a large land component positions this asset as an ideal opportunity for investors seeking stable cash flow with upside in a high-growth Central Florida market.

Listing is courtesy of: JULIAN PROPERTIES, INC. (407-291-4900)

Listing Agent: Bo Julian (407-694-5843)

Remarks: Tucked inside the gated community of The Parke at Hanover Place, this move-in ready, end-unit townhome offers a great combination of space, privacy and low-maintenance living. Located in a super convenient Seminole County location, this townhome has three bedrooms, 2.5-baths, and a one-car garage, giving you plenty of space for all your needs. When you arrive, you'll notice the oversized brick-paver driveway and an inviting front entry. Inside, the layout is open and comfortable. New luxury vinyl plank flooring has been installed throughout the lower level, giving it a clean, modern feel that is also super durable. The main living space is open and flows naturally into the kitchen. Not only do you have a breakfast bar, but also a dining area that could also be a flex space for work, or even a play area. The half bath is conveniently located downstairs. The kitchen offers plenty of cabinet space and room to spread out, making everyday use simple and functional without feeling cramped. Upstairs, the primary suite is spacious with a walk-in closet and an ensuite bath featuring dual vanities and a large shower. The additional two bedrooms have great natural light and share a full bathroom in the hallway area. There is also a laundry closet upstairs, which is very convenient. Being an end-unit really makes a difference here, featuring more privacy, extra windows and a spacious feel overall. The community itself is well-kept with a community pool to enjoy and walking areas to get out and stay active. The HOA takes care of the exterior, which makes day-to-day living that much easier. This location is super convenient with a super quick walk to the grocery store, smoothie spot, and more. You're in the heart of Casselberry close to shopping, dining and major roads, yet hidden away from the busyness. This is a small, intimate community with low turnover. Schedule your private showing today, so you don't miss out on the opportunity to call this home.

Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-333-1900)

Listing Agent: Melissa Flores (407-399-2650)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Great Opportunity, Great Location! Looking for a quiet, peaceful neighborhood with plenty of space to relax, this may be your next home! Located in Casselberry, this Wil O’ Wik home offers a large 80X125 lot with room for a pool in the rear yard. No Rear Neighbors, this home backs up to Gee Creek and a wooded tree line for extra privacy! The home features 3 bedrooms in a split design with vaulted ceilings throughout. L-Shape Living/Dining rooms, spacious kitchen featuring a breakfast bar, breakfast nook, lots of countertop and cabinet space, flowing into the family room, great for entertaining. The primary suite features vaulted ceilings, en-suite bath with DUAL WALK-IN-Closets. The guest rooms are split from the primary suite with a guest bath close by. The family room/kitchen area are light and bright due to the dual sliding glass doors which spill onto the over-sized rear screened porch and rear yard. New water heater installed February, 2026. The rear yard is extremely large with room for a pool and is extremely private as it backs up to Gee Creek and a treeline. Roof is 18 years old, Cash or Conventional financing only.

Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)

Listing Agent: Chris Brown (407-327-6997)

Remarks: One or more photo(s) has been virtually staged. SPECTACULAR 1.18-ACRE PRIVATE ESTATE IN THE HEART OF THE CITY! A rare and unparalleled opportunity to own a massive 1.18-acre private compound with NO HOA. This property offers the perfect balance of country-style space and urban convenience. Accessible through an exclusive 16-foot wide commercial gated entry, this estate is a standout find for those seeking ultimate privacy, multi-generational living, and top-tier infrastructure. THE RESIDENCES & EXPANSIVE LIVING SPACE: The main residence features a modern open-concept design with new flooring and fully remodeled bathrooms. A major highlight of this home is the additional 442 sq. ft. Florida Room, which is fully integrated into the home’s floor plan. This space features premium finishes and full climate control (A/C), providing a seamless transition from the main living areas. With this addition, the estate boasts a grand total of 3,351 sq. ft. of functional living space. The heart of the home is a gourmet kitchen with a stunning oversized island and premium stainless steel appliances, flowing into a spacious family room with a classic wood-burning fireplace. Key upgrades include: Full Repipe (2020), New Septic Tank (2018), New Roof, and a complete HVAC system replacement (2020) including all new ductwork for maximum efficiency. INCOME & MULTI-GENERATIONAL LIVING: A beautiful, custom-covered walkway connects the main home to a fully permitted Detached Guest House (2 Bed / 1 Bath + Full Kitchen & Laundry), ideal for extended family, a home office, or potential rental income. PREMIUM STORAGE & WORKSHOPS: Designed for enthusiasts! This estate features a massive, fully enclosed RV/Boat Shelter with full hookups. Additionally, find a huge Detached Climatized Workshop ("Man Cave") with dedicated electrical, a 3-car carport, and multiple storage units. VERSATILE BARN & UTILITY STRUCTURES: The property includes a professional-grade Barn with multiple stalls and a covered grooming station. These versatile structures are perfect for agricultural storage, hobbyist workshops, or animal enthusiasts. (Note: Buyer to verify specific zoning ordinances and livestock permits with local authorities). A private WELL dedicated to the irrigation system ensures a lush landscape with zero water costs. ELITE ENERGY EFFICIENCY: Experience massive utility savings with an impressive 26 kW Professional Solar Power System (Original $90,000+ investment), drastically reducing monthly overhead. This is a one-of-a-kind "lifestyle compound" that combines luxury, utility, and modern efficiency. Don’t miss this rare gem. Schedule your private tour today!

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

Listing Agent: Julian Carvajal, Llc (407-454-2632)

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: *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)