Homes for Sale Near Tuskawilla Middle in Winter Park - 70 homes

Remarks: Quiet Living in the Desirable Lazy Oaks Community of Winter Park. Welcome to the peaceful, well-established community of Lazy Oaks in highly sought-after Winter Park. This hidden gem offers beautifully landscaped grounds, meticulous maintenance, and the added benefit of a low HOA. This lovingly maintained 2-bedroom, 2-bath home features a spacious, thoughtfully designed floor plan with an attached garage. The home is ideally located near top-rated schools, shopping, dining, and provides convenient access to major highways. Inside, you’ll find a neutral color palette complemented by ceramic tile and wood laminate flooring throughout. The efficient kitchen boasts gleaming white countertops, rich wood cabinetry, and a large pantry for ample storage. The expansive great room offers flexible space for both dining and living areas, complete with a cozy wood-burning fireplace—perfect for relaxing or entertaining. Sliding glass doors open to a large, screened private lanai, ideal for morning coffee or evening unwinding. The spacious primary suite features an en suite bath with dual sinks, a large vanity, walk-in shower, and a generous closet. A split-bedroom layout provides added privacy, with a secondary bedroom and additional full bath. Additional highlight: HVAC replaced in 2021. Don’t miss this opportunity to make your home in one of Winter Park’s most charming and convenient communities!

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)

Listing Agent: Mindy Machock (407-461-1866)

Remarks: Been looking for a 4 bedroom home? Well, you have found it!!! This one owner home definitely shows pride of ownership! The attention to detail is obvious! Some of the upgrades include a 10 KW solar panel system, double pane gas insulated windows throughout the house and the enclosed lanai. The kitchen has LG appliances and granite countertops. Both bathrooms have updates as well. The house has ceramic tile throughout and bamboo flooring in the master bedroom. More updates include Trane A/C system, newer water heater, roof in 2021, and electrical panel in 2017. Also included are a garage door opener that has battery backup for power outages, ring door sensors on all main windows and doors, motion activated lights at night on all 4 sides of home, a water softener, and an I-Flo system on the A/C. All that, and a desirable neighborhood with highly rated schools! You don't want to miss this one! Make your appointment today!!!

Listing is courtesy of: OPTIMA REAL ESTATE (407-366-4500)

Listing Agent: Deborah Morgan (407-314-8610)

Remarks: Welcome to this beautifully maintained 3-bedroom, 2-bathroom corner-unit townhome located in the heart of Winter Park. Offering 1,743 square feet of thoughtfully designed living space, this home combines comfort, style, and an unbeatable location just minutes from shopping, dining, parks, and top-rated schools. The desirable corner-unit placement provides added privacy, extra natural light, and a spacious feel throughout. Inside, you’ll find luxury vinyl plank flooring flowing seamlessly throughout the home and a stunning vaulted ceiling that creates an airy, open atmosphere in the living room. The beautifully updated kitchen is truly the centerpiece of the home, featuring gorgeous wood countertops, ample cabinet space, and an open-concept layout perfect for entertaining family and friends. Step outside to the rear screened-in patio and enjoy peaceful pond views in your own private outdoor retreat. Whether you’re sipping your morning coffee or unwinding after a long day, this tranquil space offers the perfect setting to relax and enjoy Florida living year-round. This exceptional Winter Park townhome is a rare opportunity you won’t want to miss.

Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)

Listing Agent: Joseph Sipp (407-820-7016)

Remarks: Welcome to this beautifully updated home located in the Winter Park area with a Private Mother in Law Suite! This property has been thoughtfully upgraded throughout, offering peace of mind and modern living at its finest. Major system updates include a roof replaced in 2019, solar installed in 2020 (paid off at closing), new electric water heater (2026), and both AC units replaced, providing efficiency and long-term savings. The home also features some brand-new windows (2026), fresh interior and exterior paint, and enhanced curb appeal with stone accents (2016), pavers (2021), and a professionally installed retaining wall with French drainage (2021). Inside, you’ll find a fully remodeled kitchen (2023) equipped with a double oven (2025) and newer refrigerator (2022), perfect for everyday living and entertaining. The home has two fully remodeled bathrooms (2026) and updated vinyl flooring upstairs (2024) for a clean, modern look. Additional upgrades include a laundry sink (2019) and washer and dryer (2019). A standout feature of this home is the private mother-in-law suite, offering incredible flexibility for multigenerational living or potential rental income. This suite includes freshly painted walls, a full kitchen, stackable washer and dryer, spacious bedroom, and a full bathroom with walk-in shower. This move-in ready home combines major upgrades, functional space, and versatility all in a great location near shopping, dining, and all other needs. Close to UCF, Disney, I-4 and anywhere else you want to go in Central Florida! Don’t miss your opportunity to own this exceptional property, schedule your private showing today!

Listing is courtesy of: THE WILKINS WAY LLC (407-874-0230)

Listing Agent: Jeremy Toro (928-503-5659)

Remarks: Location truly matters—and this Winter Park gem delivers. This beautifully maintained 2-bedroom, 2-bath townhouse offers charm, functionality, and a rare bonus: a spacious screened-in lanai and private yard. Tucked within a well-established neighborhood, the home provides a peaceful residential setting while keeping you just minutes from everything Winter Park has to offer. Inside, you’ll find a stunning kitchen with stainless steel appliances, upgraded flooring, and modern countertops—making this home completely move-in ready. Whether you're searching for a primary residence or a smart investment, this property offers the perfect blend of comfort, flexibility, and convenience. Ideally located near Downtown Winter Park, Park Avenue, Rollins College, AdventHealth Winter Park, major highways, shopping, dining, and entertainment. You’ll also enjoy easy access to Downtown Orlando, Baldwin Park, Full Sail University, and Orlando International Airport. Opportunities like this are rare—schedule your private showing today.

Listing is courtesy of: GLOBAL PROPERTIES SALES/MGMT (352-383-4175)

Listing Agent: Joe Pietzyk (352-383-4175)

Remarks: Under contract-accepting backup offers. Welcome to Carolyn Estates in highly desirable Winter Park—a charming enclave of just 63 homes ideally located near Lake Howell High School. This beautifully renovated residence offers a truly unique floor plan—the only one of its kind in the community. Featuring 4 bedrooms, 2 bathrooms, and a spacious 2-car garage, this home blends comfort with functionality. Enjoy cozy evenings by the wood-burning fireplace or unwind in the screened-in patio, perfect for relaxing or entertaining. Step inside to an inviting open-concept layout highlighted by soaring ceilings and abundant natural light. Renovated in April 2026, this home showcases numerous upgrades, including fresh interior and exterior paint, new sod and lush landscaping, a fully remodeled second bathroom, new convection range and microwave, updated interior door hardware, a complete electrical update, and new lighting and ceiling fans throughout. Additional major improvements include newer windows and hot water heater (2019) and full home replumbing (2022), providing added peace of mind. Seller will provide a $10,000 credit towards a new roof with Full Price Offer. This move-in-ready home combines modern updates with a prime location—schedule your private showing today!

Listing is courtesy of: SELECTIVE REALTY GROUP LLC (407-627-1727)

Listing Agent: Shanon Luiz (407-247-2241)

Remarks: Under contract-accepting backup offers. SWIM WHENEVER YOU LIKE! Discover a new dimension of living - Sparkling pool awaits you, so come and dip your toes here! Pool party ideas come naturally in this proud-to-show huge fenced-in backyard with lots of entertaining space. Oversized pool deck and large rock patio, plus huge screened in porch, make a great space for Florida living. This rock-solid ranch offers 4 bedrooms and 2 baths set in over 1700+ sf. Great curb appeal with cool rock trimming and freshly landscaped beds. Roomy formal living room greets you as you enter. The primary bedroom is split from the other 3 bedrooms and lies off the living room. This primary suite offers closet space galore. Plus, pretty double vanity, separated from the shower area. Terrific, updated kitchen with neat rustic tile, quartz counters, tile backsplash, stainless appliances, cool single bowl sink and faucet, shiplap wall and closet pantry round out this kitchen space. The family room is a great size, and the kitchen quartz counter/bar also serves as a gathering place flowing into the family room, which features a shiplap TV wall and blind-inside sliders to the screened in porch. The other 3 bedrooms and 2nd bath are off the family room. All are nice sized and the bath with nifty vintage tile, has an access door to outside/pool area. Pretty luxury vinyl plank flooring through living areas. All set in Winter Park on a .23 acre lot and Cul-De-Sac street. Conveniently close to schools, hospital, shopping, Costco and restaurants. Plus, easy access to highway 436 and straight shot to the Orlando International Airport. Don’t wait on this rock-solid ranch in desirable Winter Park...it’s ready for its new owners!

Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)

Listing Agent: Teresa Jones (407-376-2130)

Remarks: Price reduced!! Spacious Winter Park home on over a half acre with no rear neighbors!. In Bear Gully Forest community and has over 2,000 s/f- with a Living Room, Dining Room, Eat-in Kitchen and more. The home's fully-equipped kitchen has excellent cabinet space and appliances that include a stove, microwave, and dishwasher. An inside laundry room has a washer/dryer combination for your convenience. Bedroom with 1/2 bath upstairs. Roof new in 2018 with a 10 year full warranty.

Listing is courtesy of: ADVANCE REALTY & MANAGEMENT LLC (407-901-3636)

Listing Agent: Craig Swetnam (407-802-0405)

Remarks: PRICE REDUCED!! Welcome to your dream home! This beautifully renovated single-story residence features 3 spacious bedrooms and 2 baths, all set on an expansive .42-acre lot in the desirable Howell Estates community. Brand New Roof (2024) Replumbed (2024) New HVAC System, Gourmet Kitchen: Brand new upgraded white cabinets, stunning quartz countertops, and new stainless steel appliances. Luxurious Bathrooms: Both completely renovated, featuring modern finishes Oversized Bedrooms: Including a primary suite with his-and-hers closets and an ensuite bath with a gorgeous walk-in shower. In the Family Room: Spacious layout with a cozy wood-burning fireplace, Oversized Garage: Perfect for larger vehicles, including SUVs. The backyard has a: New Fence, New Pergola and New Extended Porch. This home is move-in ready and waiting for your family to create lasting memories. Don’t miss out on this exceptional opportunity in Winter Park!

Listing is courtesy of: FLORIDA INVESTMENT REALTY GRP (407-937-8450)

Listing Agent: Yuleisy Marquez (407-937-8450)

Remarks: Exceptional Single-Family Home in Winter Park, FL This beautifully maintained 3-bedroom, 2.5-bathroom residence offers an impressive open floor plan with elegant laminate flooring throughout, updated just two years ago. The renovated kitchen (2019) features granite countertops and comes fully equipped with all appliances. Major capital improvements include a new roof (2019) and a new HVAC system (2023), new water heater (2026), providing peace of mind for years to come. Enjoy Florida living at its finest on the private screened patio - perfect for relaxing or entertaining. Ideally situated 25 minutes from Downtown Orlando, 30 min from OIA, and 40 min from world-class attractions, this home is also just 6 minutes from Full Sail University, 12 minutes from the prominent Rollins College, and 19 minutes from UCF - making it an ideal choice for families and investors alike. A true must-see - schedule your showing today.

Listing is courtesy of: EXIT GLOBAL REALTY (407-725-7180)

Listing Agent: Hugo Hernandez (407-716-5594)

Remarks: Beautifully renovated 3 bedroom 2.5 bath pool home located in the lake-centric community of Country Lane in Winter Park. Residents enjoy exclusive access to Lake Florence, offering kayaking, fishing, and scenic outdoor recreation just moments from home. Perfectly positioned on a premium lot with ample space, this property combines privacy, modern upgrades, and exceptional indoor-outdoor living. Recently renovated, the home features brand-new interior paint and a stunning designer kitchen complete with quartz countertops, white shaker cabinetry, and stainless steel appliances. The oversized pool and expansive paver deck create the ideal setting for entertaining, relaxing, and sunbathing year-round. Additional updates include a 2022 roof for added peace of mind. Inside, rich wood flooring flows throughout the home, complemented by soaring ceilings and a cozy fireplace in the family room. The oversized primary suite offers ample space for a king-sized bed, seating area, dresser, and more, while custom built-in closet organizers provide exceptional storage. A secondary upstairs bedroom also features custom closet systems. The screened lanai seamlessly blends indoor and outdoor living and has been thoughtfully upgraded with elegant wood plank ceilings, creating a warm and inviting atmosphere overlooking the pool. Conveniently located with easy access to SR-426 and SR-436, this home is less than five minutes from shopping, dining, entertainment, Trinity Preparatory School, Costco, Target, and vibrant downtown Winter Park.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Daniel Hsieh (813-313-0010)

Remarks: Under contract-accepting backup offers. BELOW APPRAISAL GEM IN WINTER PARK. Welcome to this beautifully and luxuriously updated 4-bedroom, 4-bath pool home located in the highly desirable Kings Cove community of Winter Park. Offering over 3,000 square feet of living space on a spacious 0.31-acre lot, this home blends comfort, functionality, and major system upgrades. The kitchen is designed for both everyday living and entertaining, featuring a gas stove, double oven, warming drawer, extra-large refrigerator, and custom pull-out cabinetry. The oversized island includes an additional sink, built-in microwave, and new (2025) under-counter ice maker. Recent upgrades and improvements include: New roof (2021) New first-floor A/C system (2021) New septic tank (2023) New hot water heater (2025) The primary suite has been thoughtfully updated in 2026, featuring a fully renovated bathroom with dual sinks and in-drawer electrical outlets, along with a custom-designed closet system completed in March 2026. New carpet was installed in April 2026. Additional highlights include a dedicated laundry room with sink and wine storage, a custom pantry with oversized pull-out drawers, built-in entertainment center, and a ceiling-mounted audio system controlled by phone. Step outside to enjoy your private in-ground pool and a quiet, established neighborhood close to top-rated schools, shopping, dining, and major highways. This is a move-in-ready home with major systems already updated and high-end functional upgrades throughout—don’t miss this opportunity.

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

Listing Agent: Renata Dove (407-923-8216)

Remarks: Under contract-accepting backup offers. Great investment opportunity. Ideal for a growing family or investor. Well established neighborhood of Goldenrod Villas, 3 bedroom, 2 full bathrooms, 1,230 square feet of living area. Exterior of the home is concrete block and stucco. The eat-in-kitchen sits in the heart of the home which creates a warm and social atmosphere. Nice covered patio with back yard great for relaxing and entertaining family and friends. Come and make it your own. The HOA maintains building exterior, roof, and exterior landscape maintenance. The Community features enjoyable sparkling swimming pool and clubhouse. Great location! Conveniently located to nearby shopping, schools, banks, medical centers, and restaurants as well as easy access to major highways. Don't miss it. Priced to sell. Will Not Last!

Listing is courtesy of: REALTY TECH INC (407-332-9757)

Listing Agent: Carmen Vazquez (407-617-9045)

Remarks: Under contract-accepting backup offers. BRAND NEW ROOF 2026 to be installed next week. Beautifully updated and move-in ready home in Winter Park featuring a BRAND NEW 2026 A/C system and water heater from 2009. This 4-bedroom, 2.5-bath home with a 2-car garage offers waterproof luxury vinyl flooring, recessed lighting, updated fixtures, fireplace, screened patio, and a bright, functional layout filled with natural light. The upgraded kitchen and bathrooms are a must-see. The fully renovated kitchen features custom green cabinetry, quartz countertops, farmhouse sink, gold hardware, pantry, and new stainless steel appliances. The oversized primary suite includes a spa-style bathroom with soaking tub, double vanity, rainfall shower, and dual closets. Located in a community with a community pool and low HOA of only $39 x month. Conveniently located near Downtown Winter Park, Park Avenue, Rollins College, AdventHealth Winter Park, major highways, shopping, dining, and entertainment. Easy access to Downtown Orlando, Baldwin Park, Full Sail University, and Orlando International Airport makes this location ideal for both convenience and lifestyle.

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)

Listing Agent: Alexa Monasterio Flores (786-915-9294)

Remarks: Welcome to 1174 Wildmeadow Run in Winter Park’s gated Hawk’s Crest community. Situated on a quiet non-thru street, this SINGLE-STORY residence offers modern construction, refined finishes, and a thoughtfully designed layout for everyday living and easy entertaining. The open-concept design feels light and inviting, featuring WOOD-LOOK TILE FLOORING, crown molding, recessed lighting, CUSTOM PLANTATION SHUTTERS, and ENERGY-EFFICIENT DOUBLE-PANE WINDOWS throughout the main living areas. At the center of the home, the kitchen is both functional and inviting, showcasing quartz countertops, stainless steel appliances, white cabinetry with crown molding, a custom backsplash, a PREP ISLAND, and a SECOND LARGE ISLAND WITH SEATING that seamlessly connects to the living and dining spaces. A FRENCH-DOOR FLEX ROOM provides a versatile space for a home office, formal dining room, or additional living area. The private primary suite offers a TRAY CEILING, generous walk-in closet, and a well-appointed en-suite bath with dual-sink quartz vanity, upgraded cabinetry, and a GLASS-ENCLOSED WALK-IN SHOWER. Two additional bedrooms are thoughtfully positioned in this split plan and share a FULL BATH WITH TUB AND SHOWER COMBINATION and QUARTZ VANITY, while a SEPARATE HALF BATH is conveniently located for guests. A TRIPLE SLIDING GLASS DOOR opens to a COVERED REAR LANAI overlooking a FULLY FENCED BACKYARD with room to accommodate a FUTURE POOL, creating a seamless indoor-outdoor lifestyle. Additional features include a two-car garage with built-in storage, BRICK PAVER DRIVEWAY, TERRACOTTA TILE ROOF, GUTTERS, smart-home pre-wiring, and an HVAC SYSTEM WITH IONIZATION FEATURE designed to help improve air quality. Residents of Hawk’s Crest enjoy RESORT-STYLE AMENITIES including a lakeside pool, fitness center, clubhouse, splash pad, playgrounds, walking trails, BBQ areas, and scenic docks and boardwalks, with lawn care included. Ideally located near Winter Park dining, shopping, and everyday conveniences. Seller relocation timeline presents a compelling opportunity to secure a move-in ready home in one of the area’s most desirable gated communities.

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

Listing Agent: Kara Lushear (321-663-5550)

Remarks: Come and see your new home in the sought after Vistas at Howell Branch community. This two story townhouse has 3 bedrooms, 2.5 baths, and open first floor, floor plan. Relax in the evening on your screened in porch. The master bedroom has a walk in closet and large master bath. Your washer and dryer are on the second floor centrally located to all the bedrooms. You will find yourself within walking distance of restaurants, grocery stores, and other retail outlets. It's central location puts within minutes of 436 and 417. Schedule your showing today!

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

Listing Agent: Ashley Fisak (407-848-7975)

Remarks: Under contract-accepting backup offers. A house in Winter Park under $500K?! No way! Let's not forget, everything was fully gutted and remodeled in 2023. New roof, water heater, AC, electrical wiring and panel, plumbing, double pane windows, water softener, flooring, exterior paint, bathrooms, kitchen, outdoor french drains, garage door, screened-in lanai — ALL ONLY THREE YEARS OLD. This home is the absolute definition of MOVE-IN READY. Situated on a 1/4 acre oversized lot, there's plenty of room for you to add a pool, park your boat, or create that true backyard oasis you've been dreaming of. Fully fenced-in and NO HOA. The kitchen features high-end quartzite countertops with a built-in pantry and newer stainless steel appliances. Open floor plan with high ceilings and tons of natural light. Almost 2,000 sqft of living area with an inside utility room that houses your washer/dryer (which are included with the purchase!). Master bedroom is equipped with a massive 8'x11' walk-in closet and a show-stopping en-suite bathroom! Conveniently located 10 minutes from Park Avenue, 15 minutes from Valencia and/or UCF, and right around the corner from highway ramps making commuting a breeze. Homes like this don't come often. Don't miss your chance to live in Winter Park!

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

Listing Agent: Angie Kollcaku (407-454-4078)

Remarks: One or more photo(s) has been virtually staged. Set within the serene gated community of Hawks Crest in Winter Park, this beautifully designed single-story home combines modern comfort with resort-style living. Featuring 4 bedrooms, 2 baths, and 1,920 sq. ft. of thoughtfully crafted space, it’s the perfect blend of style and function. Inside, an open-concept layout creates seamless flow between the spacious family room, dining area, and gourmet kitchen—ideal for entertaining and everyday living. The kitchen offers granite countertops, large island seating, and stainless-steel appliances. The private owner’s suite is a relaxing retreat with a walk-in closet and spa-inspired bath, while three additional bedrooms provide flexibility for family, guests, or a home office. Step outside to a covered patio and low-maintenance yard designed for year-round Florida living, and pond view. Hawks Crest residents enjoy exclusive amenities including a clubhouse with fitness center, resort-style pool, splash pad, dog park, playgrounds, and private access to Lake Howell for kayaking and paddle boarding. The neighborhood is also minutes from local favorites like Kelly’s Ice Cream and Foxtail Coffee, with downtown Maitland, Park Avenue, and top-rated schools just minutes away. This home delivers not just a place to live, but a lifestyle defined by convenience, community, and charm. Don’t miss your chance to own in one of Winter Park’s most desirable neighborhoods—schedule your private showing today.

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

Listing Agent: Brian Rotenberger (407-948-8478)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Back on the market and better than ever! New water heater and minor repairs addressed and ready for the new owner! Come see this newly renovated home in the Eastbrook neighborhood of Winter Park. Offering 3 bedrooms and 2 full baths it’s the perfect sanctuary for families and entertainers alike. You will enjoy the bright, airy feel of the open floor plan accentuated by the vaulted ceilings that flood the space with natural light. The stylish interior includes luxury vinyl plank flooring throughout, complemented by elegant tile in the bathrooms and laundry room. Relax in not one, but two generous living areas, perfect for family gatherings, entertaining or cozy nights in. Cook like a pro in your eat-in kitchen featuring brand new ENERGY STAR stainless steel appliances, ample cabinetry, and convenient carport access for effortless unloading. The generous backyard provides a private oasis for outdoor activities, barbecues, and gardening enthusiasts. Plus, the expansive driveway and two-car carport ensure plenty of parking for your guests. Recent upgrades include ceiling fans, blinds, fresh paint, stainless steel appliances, a newer roof (2017) and a well-maintained air conditioner (only 4 years old) ensuring peace of mind for years to come. Located in Seminole County, known for great schools and in a community with NO HOA fees, giving you the freedom to enjoy your space. Plus, you're just moments away from shopping, dining, and parks!

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

Listing Agent: Brenda Feliciani (407-405-0931)

Remarks: Tucked into one of Winter Park's most convenient pockets, this thoughtfully updated residence offers a seamless blend of comfort, style, and convenience. With three bedrooms and two bathrooms, the layout provides flexibility for a variety of living arrangements while maintaining a warm, welcoming feel throughout. The updated kitchen is both functional and inviting, featuring a gas stove and a dedicated coffee bar that adds a touch of everyday luxury. Living spaces flow effortlessly to the outdoors, where a large screened-in porch invites year-round enjoyment, complemented by a paved patio with a firepit that's ideal for relaxed evenings. The yard is perfectly sized for easy maintenance and enjoyment, complete with built-in swings that add a unique and playful detail. Positioned in a highly desirable location, this home is just moments from Interlachen Country Club, Full Sail University, and AdventHealth Winter Park, with everyday essentials like Costco nearby. Enjoy quick access to the shopping and dining of Park Avenue, just 15 minutes away. A rare opportunity to enjoy a move-in-ready home in one of Winter Park’s most convenient and connected areas. Recent updates include a 2021 roof, offering peace of mind and move-in ready convenience.

Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)

Listing Agent: Hannah True (407-923-9330)