Homes for Sale Near Glenridge Middle in Winter Park - 71 homes

Remarks: Welcome to this stylishly renovated ranch-style pool home in Kenilworth Terrace, a special Winter Park neighborhood known for its connected community, central location, and easy access to everything people love about Winter Park. This beautifully renovated 3-bedroom, 2-bath home sits on nearly a quarter-acre lot and offers the perfect blend of style, comfort, and outdoor living. Step inside and you'll immediately feel the warmth of the home. The renovated kitchen is truly the heart of the space, beautifully designed with stylish tile backsplash, stainless steel appliances, mission style cabinetry, bar seating, and an additional coffee or wine bar area that makes the space feel both functional and elevated. Open to the living room, the kitchen creates an easy flow for everyday living and entertaining. The home has been thoughtfully updated throughout with new flooring, plantation shutters, renovated bathrooms, and designer touches that give the home a fresh, modern feel while still keeping all the charm of a classic Winter Park ranch. A dining room along the back of the home offers views of the yard and access to the covered lanai and custom pergola overlooking the pool. This is truly a backyard retreat! The sparkling pool is surrounded by pavers, lush landscaping, bamboo for privacy, and a fully fenced yard. The covered lanai and custom pergola create the perfect setting for morning coffee, quiet evenings, or hosting friends by the pool. This is the kind of backyard that makes Florida living feel easy. A large storage area and laundry room provide extra space for bikes and yard tools just off the carport. The bedrooms are tucked together along the hall, with the primary bedroom positioned on the back of the home for privacy, with an additional bathroom featuring an updated vanity and shower and a door to the pool area. The additional bedrooms share the hall bathroom with stylish modern updates including all new tile, a frameless glass shower, vanity, and fixtures. The thoughtfully designed spaces feel modern while also remaining timeless and classic. Additional features include a metal roof and newer windows and doors. Other notable additions over the years include irrigation, lush landscaping, and a refinished pool with tile surround. The 2-car carport provides plenty of covered parking for rainy days! Located in the City of Winter Park, this home offers incredible access to Park Avenue shopping and dining, Audubon Park with Michelin-star restaurants and local favorites, Sprouts Market, Lake Baldwin Dog Park, nearby parks, coffee shops, boutiques, and more. Zoned for Brookshire Elementary, Glenridge Middle, and Winter Park High. Cady Way Park is nearby with a community pool, baseball fields, a playground, pickleball courts, and miles of recreational and bike trails. Style, location, privacy, sparkling pool! This Winter Park home checks all the boxes. Schedule your private showing today!

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

Listing Agent: Kathryn Stelljes (407-982-7240)

Remarks: Nestled within the highly sought-after Windsong community in Winter Park, this thoughtfully designed residence presents the perfect balance of functionality, comfort, and elevated indoor-outdoor living. This move-in ready home is sure to check all the boxes with 2 NEW HVAC units (2025), a downstairs Primary Suite, a convenient 1st floor private office/flex room, 2nd floor loft & bonus room, plus a private backyard oasis complete with a full summer kitchen, covered rear lanai, and saltwater pool with a heated spa. The large, covered front porch welcomes guests into a foyer that opens to a spacious and well-orchestrated floorplan. Just off the entry sits a versatile office/flex space, providing the perfect setting for a private workspace or playroom, while a conveniently located powder bath serves visitors with ease. The foyer unfolds with effortless flow into the heart of the home, where an expansive living room is designed for both everyday living and entertaining. The open-concept kitchen is both functional and refined, featuring a natural gas cooktop, built-in double ovens, and adjacent sunny dinette that overlooks the backyard and pool, creating a casual dining space filled with natural light. On the opposite end of the kitchen, a large walk-in pantry offers tons of storage, and a butler’s pantry/dry bar seamlessly adjoins the large dining room—ideal for hosting gatherings with a polished, intentional flow. At the rear of the living space, expansive stacking glass sliders open to the rear covered lanai, extending the living space outdoors. Enjoy space for dining, lounging, and entertaining with a full summer kitchen that includes a large gas grill, double gas burners, a sink, beverage fridge, and storage cabinets. The backyard beyond creates a true retreat that embodies the Florida lifestyle, where a heated spa overflows into a beautifully designed saltwater pool complete with a sun shelf, all wrapped in travertine decking, tropical landscaping, and a masonry wall for enhanced privacy. Situated at the rear of the home, the well-appointed primary suite offers a quiet escape with generous proportions, dual walk-in closets, and a sensible primary bath with split vanities, a soaking tub, separate shower, and private water closet. The main level continues with exceptional functionality, including a spacious laundry room lined with built-in cabinets for storage, and a 2-car garage with direct access to the side yard and overhead racks for additional storage capacity. Upstairs, a thoughtfully designed 2nd level provides incredible flexibility, featuring a central loft for a reading or study area, a large bonus room that's perfect for a game room or secondary living area, three additional bedrooms - each with walk-in closets, two full bathrooms, and a linen closet, plus an additional storage/media closet. This home is not just a residence—it’s a lifestyle. Windsong residents enjoy access to premier amenities, including multiple community pools, a splash pad, playgrounds, a clubhouse, and 2 community docks providing access to the Winter Park Chain of Lakes via Lake Berry & Lake Mizell. Ideally located just minutes from Park Avenue, Baldwin Park, and the vibrant Corrine Drive corridor, this property offers tranquility and convenience in one of Winter Park’s most desirable neighborhoods.

Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)

Listing Agent: Marystuart Day (407-620-8683)

Remarks: Under contract-accepting backup offers. *MULTIPLE OFFERS! FINAL AND BEST OFFERS BY 10 PM 06/01/26* Welcome home to this beautifully maintained 3-bedroom, 2-bath *POOL* home in desirable Winter Park! Offering 1,678 square feet of single-story living, this home features an open floor plan with a spacious kitchen/family room combination. The open kitchen features 36” oak cabinetry, upgraded SS appliances, a garden window, and a kitchen island overlooking the dinette and family room. You’ll find laminate and tile flooring throughout the home, updated bedroom light fixtures (2026), and a converted 2-car garage offering flexible bonus space if you desire. Owners can escape to their primary suite with a walk-in closet, en-suite bathroom, and private French doors leading out to the HEATED SALTWATER POOL. Step outside to your own private backyard featuring an oversized covered patio with screened-in pool and a built-in spa, plenty of yard space to enjoy, a backyard shed for additional storage, a swing set, and a playhouse perfect for outdoor fun. With NO HOA, you’ll have the freedom to truly make this space your own! Major updates provide peace of mind, including a NEW water heater (2026), electrical panel replacement (2023), salinator replacement (2023), pool heater replacement (2024), roof (2019), and AC (2025). Conveniently located near shopping, dining, parks, and top-rated Seminole County schools, this move-in-ready home is the perfect blend of comfort, functionality, and Florida living!

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)

Listing Agent: Jadel Patterson, Llc (407-922-5936)

Remarks: Welcome to your dream home in the highly sought-after community of Winter Park Pines! This beautifully maintained 4-bedroom, 3-bathroom residence offers 2,312 square feet of comfortable and stylish living space ideally designed for modern and multigenerational lifestyles. The recently remodeled primary suite is a true retreat, featuring new carpeting and tile flooring, dual granite vanities, an oversized walk-in shower with modern, upgraded fixtures, a new water closet, and thoughtful contemporary finishes throughout. Inside, you’ll find timeless architectural charm which includes a formal dining room, three spacious living areas, plantation style shutters, and elegant hardwood flooring. One of the living spaces is highlighted by a stunning brick fireplace overlooking the beautiful private pool area and fully fenced backyard — creating the perfect setting for entertaining, family gatherings, or simply unwinding in your own backyard oasis. In addition, this spectacular residence also boasts tasteful landscaping touches for exceptional curb appeal, a large two-car garage with electric opener, a newer shingle roof replaced in late 2023, and fresh interior paint throughout the home. Ideally located near Winter Park Pines Golf Club, Cady Way Trail, Ward Park, Showalter Field, tennis and pickleball courts, top-rated schools, and the many shopping and dining destinations of Park Avenue and historic downtown Winter Park. Don’t miss this rare opportunity to own a true Winter Park gem — schedule your private showing today!

Listing is courtesy of: DAHLIA REALTY GROUP (689-777-4111)

Listing Agent: Chuck Tolfa (407-782-3518)

Remarks: One or more photo(s) has been virtually staged. Located in the highly desirable Winter Park area, 1944 Natalen Rd offers the perfect balance of tranquility, convenience, and lifestyle. This property enjoys deeded access to serene Lake Berry while being just minutes from top-rated schools, the vibrant dining and boutique shopping of both Baldwin Park and downtown Winter Park, and everyday conveniences including nearby grocery stores and the renowned Winter Park Farmers’ Market. Residents will appreciate exceptional healthcare access with both AdventHealth Winter Park and the Orlando VA Medical Center at Lake Baldwin close by. Centrally located with easy access to UCF, Orlando International Airport, and Central Florida’s world-famous theme parks and attractions, this home provides an ideal combination of peaceful living and connectivity to everything Orlando has to offer.

Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)

Listing Agent: Trevor Thomas (407-337-8738)

Remarks: Elegant 1922 Mission Revival home, located in popular College Quarter is a registered historic place in Winter Park, FL. Lifestyle is neighborly/relaxed/pet friendly/enhanced by proximity to Lake Virginia/lakeshore sidewalks/Rollins College campus/downtown Winter Park/Central Park/museums/shops/restaurants/cultural events, most walking distance. College Quarter residents enjoy exclusive use of Park/Dock on Lake Virginia to kayak/paddleboard/motor through Chain of Lakes or meet up for holiday fireworks/once-in-a-lifetime or yearly celestial events. College Quarter is one of the oldest/most architecturally diverse neighborhoods. This 1922 home represents the Florida Mission Revival vernacular through a timeless blend of stucco exterior walls/asymmetrical façade/prominent arches above doors/large windows/a flat roof/barrel red tiles/a distinctive parapet and walled courtyard with wrought-iron gate designed by local master ironworker. True to Mission Revival style, home connects to nature and surrounding College Quarter landscape through above architectural details that embody poetics of Mission Revival style. Builder used sensitive siting, placed home at highest elevation on street & it remains responsive to prevailing lake breezes/paths of rising sun & moon 104 years later. Lake light/sunlight/moonlight take centerstage in every room. Whether through window or door, each part of house has relationship with its surroundings. Mission Revival style accomplishes what homeowners often seek—a home’s ability to surprise. Airiness/lightness, beautiful atmosphere/ambience that Mission Revival architecture creates is notable that way. Mission Revival layout is key to that effect. Home’s modified Great Room layout combines roles of several traditional rooms--family/kitchen/living/dining rooms into 1 expansive space ideal for families/entertaining guests/enjoying natural light/views. Open layout in house is conducive to spending quality time together/socializing/entertaining. Proximity of kitchen/dining/living & outdoor spaces allow for easy interaction/conversation & creates sense of togetherness. Great Room dominates first floor living/dining room areas. One interior archway frames foyer, another leads to family room. Left of fireplace in Great Room are French Doors to enclosed porch/walled courtyard/plunge pool. Ceiling is 10 ft exposed rafters, 2 large, arched windows, one on East wall, one on West, face each other across 4 interior spaces. Changing light seen through handblown windowpanes in Great Room illuminate first floor & exterior environment. When moon rises over lake's cypress trees it appears in Great Room east window, travels thru sky, peeps into 2nd floor windows before moving ever higher in the sky. Kitchen’s center island is gleaming butcher block & divides food prep area from pantry/laundry/guest bathroom/living/dining areas. Kitchen counter imported tile/oak cabinets/small eat-in breakfast nook. French Doors open to brick courtyard/garden area/plunge pool. Kitchen/Pantry/Guest Bathroom have heart of pine floors. Laundry new ceramic tile, built-in wood cabinets/shelves, new washer/dryer, stainless-steel sink. Great Room floors original oak. Staircase/second story floors original heart of pine. Bedroom 1 ensuite Bathroom/Linen Closet/Balcony. Bedroom 2 beautiful views/2 closets/built-in drawers/. Bedroom 3 best water views during day. Single-family ownership 45 years. Roof & 2 balconies 5 yrs old. Major renovations 2021- to present

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

Listing Agent: Wendy Brandon (407-435-9009)

Remarks: What better value! Accepting offers. Clean, Crisp and Fresh! Welcome home! NEWLY RENOVATED BATHROOM on deck. Is Winter Park your destination or desire? Investment Potential, Student Sanctuary or just a long-awaited life. Centrally located at your fingertips. Location, Lifestyle, Luxurious Zip Code, Friends, Culture and Community. Discover an unparalleled opportunity to own a piece of prime real estate in the heart of Winter Park, Florida. This beautifully appointed condo apartment is located within a vibrant, amenity-rich HOA community offering a perfect blend of convenience and value. Whether you're a first-time buyer, a savvy investor seeking strong rental return, a student prioritizing location and community or a loving and supportive parent wanting to be closer to your excelling child, this unit checks every box, all at an exceptional, reasonable price point. The very best luxury boutiques, fine dining, sidewalk cafes, and vibrant art festivals. Instant access to top tier schools and hospitals. Directly across from Full Sail University, minutes to Rollins College, UCF, Valencia College and major medical centers like AdventHealth and Orlando Health facilities, making it ideal for any resident, and or faculty. Transportation is easily accessible to Downtown Orlando where the famous Lake Eola Park is, Winter Springs, Oviedo, The Orlando International Airport, Cady Way Trail, biking, hiking, swimming, volleyball, pickleball, tennis and painting at The Crealde School of Art. There's just so much within reach. Explore local gatherings, social events and community connections. For all investors, strong rental income potential and appreciation value. There's low maintenance and worry-free ownership opportunities. Let's build a portfolio together or get you owning immediately. Let's get your private tour scheduled.

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

Listing Agent: Cassandra Kelly Flores (347-723-4649)

Remarks: One or more photo(s) has been virtually staged. Under Construction. Under construction. Experience approachable luxury combined with wellness-focused living in this newly crafted masterpiece by Urban Perch, a boutique home builder. In downtown Winter Park, this stunning new construction home offers 3,421 square feet of elegant, efficient living area. The primary residence features four bedrooms plus a generous flex space, the perfect office, home gym or playroom and 4.5 baths with designer fixtures and finishes. A separate casita with a full bath provides additional space for multigenerational living or as a private guesthouse. Upon entering, you are greeted by an expansive open-plan living area with soaring ceilings that effortlessly blends sophisticated style with indulging comfort. The kitchen is a culinary dream, equipped with Le Cornue and Monogram appliances, marble and quartzite countertops and a separate scullery with plenty of storage and ample prep space. The kitchen opens to one of the main living areas, featuring a precast concrete fireplace surround with exquisite millwork details, forming a focal point leading up to the angular ceiling and overhead beams. Engineered hardwood floors throughout and curated specialty tiles in wet spaces ensure the home maintains a clean, classic and modern feel. Floor-to-ceiling French doors and oversized sliders invite natural light and offer views of the beautifully landscaped grounds, including a sparkling heated saltwater pool and fully equipped outdoor kitchen. This wellness home incorporates advanced features to ensure a healthy living environment, from air and water purification systems to specialty lighting, all designed to promote a balanced lifestyle. Just moments from charming parks, highly rated restaurants and boutique shopping, 1627 Mizell Avenue is more than just a home, it’s a sanctuary. With excellent accessibility and a vibrant community, this is an ideal setting for those seeking a blend of suburban tranquility and urban convenience.

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Bianca Khoury (407-797-1121)

Remarks: Welcome home to this stunningly updated two-story condo that perfectly combines modern elegance with everyday comfort. Featuring 2 spacious bedrooms and 2.5 baths, this home has been thoughtfully updated with high-end designer finishes throughout. The first floor showcases stunning new tile flooring in a striking neutral pattern, creating a modern and inviting living space, while the second floor features durable and stylish vinyl flooring for added comfort. The fully renovated bathrooms boast contemporary designs and quality craftsmanship, and a brand-new AC system ensures year-round efficiency and peace of mind. Natural light pours into every corner of the home, enhancing the open layout and highlighting the elegant upgrades. Ideally located just minutes from shopping, dining, and top-rated schools, this condo offers both luxury living and everyday convenience. Don’t miss the opportunity to own this move-in-ready gem in a prime location!

Listing is courtesy of: STIRLING INTERNATIONAL REAL ES (407-250-1000)

Listing Agent: Rosa Rodriguez (407-832-1185)

Remarks: Step into this beautifully renovated two-story condo offering the perfect blend of modern style and everyday comfort. Featuring 2 spacious bedrooms and 2.5 updated bathrooms, this home has been thoughtfully upgraded from top to bottom. The first floor showcases elegant marble-look tile flooring, creating a sleek and durable living space ideal for both relaxing and entertaining. Upstairs, you’ll find stylish and low-maintenance vinyl flooring throughout, adding warmth and continuity to the private living quarters. The fully renovated bathrooms boast contemporary finishes and fixtures, delivering a fresh, spa-like feel. A brand-new AC system ensures year-round comfort and energy efficiency. With its modern upgrades, functional layout, and move-in-ready condition, this condo is a perfect choice for buyers seeking both style and convenience.

Listing is courtesy of: STIRLING INTERNATIONAL REAL ES (407-250-1000)

Listing Agent: Rosa Rodriguez (407-832-1185)

Remarks: Discover refined living in the heart of Winter Park, where timeless luxury meets an unmatched lifestyle. This beautifully designed single-story residence offers three spacious bedrooms, a private office, two elegantly appointed baths and over 2,000 square feet of living space complete with a two-car garage and no HOA. Thoughtfully curated with sleek tile flooring throughout and no carpeting, the home exudes both style and comfort. The well-equipped kitchen features granite countertops, a pantry, and a charming breakfast area, flowing effortlessly into the expansive family and dining rooms. French doors open to a generous screened lanai and a private fenced backyard, creating the perfect setting for seamless indoor-outdoor entertaining. Designed with a desirable split floor plan, the luxurious primary suite offers private backyard access, dual walk-in closets plus an additional storage closet and a private bath with a spacious walk-in shower. Two additional guest bedrooms share a beautifully appointed bath with shower/tub, while one bedroom enjoys direct access to a dedicated office space, ideal for guests or working from home. Winter Park is celebrated for its distinctive blend of arts and culture, charming sidewalk cafés, acclaimed museums, upscale accessible neighborhoods, scenic lakes, outdoor recreation and year-round festivals. Surrounded by top-rated schools and picturesque tree-lined streets, this exceptional location offers premier conveniences. The residence is near AdventHealth Winter Park, Cady Way Trail and recreational parks, YMCA of Central Florida, public golf courses, Rollins College, Full Sail University and University of Central Florida. From vibrant farmers markets and outdoor concerts to nationally recognized art festivals and lakeside recreation, Winter Park offers a lifestyle that is deeply connected to community. Schedule your private showing today. The roof was updated in 2018, and the air conditioner was updated in 2015.

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Farah Novin (407-234-0501)

Remarks: Located in Winter Park Pines, this 4-bedroom, 2-bath home offers a warm, flexible layout with comfortable living spaces and everyday functionality throughout. With 1,596 square feet, the home provides room to gather, relax, entertain, and adapt to changing needs over time. Inside, the floor plan includes both a living room and a separate family room, creating useful separation for daily life. One of the bedrooms has been converted into a large closet and dressing room, offering generous storage while still allowing the option to easily convert the space back into a traditional fourth bedroom if desired. The backyard extends the home outdoors with a patio and cobblestone brick area that is well suited for entertaining, outdoor dining, or quiet evenings at home. Set within the established Winter Park Pines community, the home offers sidewalks for excellent walkability, with Cady Way Trail just steps from your door for morning runs, bike rides, and everything in between. Nearby, Cady Way Park adds even more to the neighborhood lifestyle with its pool, tennis and pickleball courts, playground, and beach volleyball, while Park Avenue offers boutique shopping and exceptional dining just minutes away. UCF, Rollins College, and Full Sail University are all within easy reach, along with AdventHealth Winter Park and Orlando International Airport. Zoned for top-rated Winter Park schools, this home combines comfort, convenience, and the everyday appeal that continues to make Winter Park Pines one of Winter Park’s most established neighborhoods.

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

Listing Agent: Melissa Johnson (407-681-4393)

Remarks: Welcome to this beautifully updated four-bedroom, two-bathroom pool home offering 1,813 square feet of thoughtfully designed living space in one of Winter Park’s most desirable locations. Perfectly positioned on a spacious lot backing up to the scenic Cady Way Trail, this residence seamlessly blends modern updates, timeless charm, and exceptional outdoor living. Inside, the versatile floor plan includes a dedicated den, office, or playroom, ideal for today’s flexible lifestyle needs. Engineered hardwood flooring flows throughout the home and is complemented by recessed lighting, crown molding, plantation shutters, ceiling fans, and elegant French doors that add warmth and character to every space. A spacious laundry/utility room offers additional storage and convenience, complete with a washer and dryer replaced in 2024. The beautifully remodeled kitchen, updated in 2020, serves as the heart of the home and showcases white shaker-style cabinetry, sleek black granite countertops, matte grey stainless steel appliances, a striking herringbone tile backsplash, and a charming exposed wood beam feature that adds architectural interest. A breakfast bar with seating for three creates the perfect gathering space for casual dining and entertaining, while the spacious dining room easily accommodates sit-down meals and larger gatherings. The private primary suite offers a relaxing retreat featuring a shiplap accent wall, ceiling fan, and an updated ensuite bathroom remodeled in 2020 with a single vanity and beautifully tiled shower with a glass partition. The secondary bedrooms are generously sized and share an updated hall bathroom featuring a tiled tub and shower combination along with a contemporary single vanity. Step outside into your own backyard oasis where a screened, heated, salt-generated pool installed in 2022 creates the ultimate setting for year-round enjoyment. The fully fenced backyard, updated in 2022, offers privacy and plenty of room for pets, play, and entertaining while overlooking the picturesque Cady Way Trail. A private gate provides direct access to the trail, allowing for convenient access to Brookshire Elementary and nearby community amenities. Additional exterior highlights include a spacious two-car carport, whole-house generator hookup, and two included storage sheds providing excellent functionality and additional storage space. This exceptional location places you just minutes from some of Central Florida’s most sought-after amenities including the Winter Park Pines Golf Course, the Cady Way Trail, and the popular Cady Way recreational amenities featuring a community pool, playground, beach volleyball courts, tennis courts, and pickleball courts. Conveniently located near University of Central Florida, Rollins College, and Full Sail University, this home also offers quick access to AdventHealth Winter Park and the Crosby Wellness Center, both less than five minutes away, while Orlando International Airport is approximately 25 minutes from home. Zoned for top-rated Brookshire Elementary, Glenridge Middle School, and Winter Park High School, this property offers an incredible opportunity to enjoy the very best of Winter Park living. ROOF - 2014 HVAC - 2023 ELECTRICAL - 2021(new panel)

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

Listing Agent: Amy Turner (407-803-3885)

Remarks: Beautifully renovated solid block home on a quiet street in highly desirable Winter Park Pines! This property features fresh exterior paint, updated lighting, a newly paved courtyard, and a bright open floor plan. The stunning kitchen offers modern cabinetry, quartz countertops, and brand-new stainless steel appliances, flowing seamlessly into the dining and family rooms. The sun-drenched Florida room is lined with windows that brighten the entire living space. Complete with a dry bar and its own mini-split AC unit, it offers flexible space for entertaining, relaxing, or creating your dream retreat. The split floor plan includes three generously sized bedrooms and three full renovated bathrooms, with a private primary suite with walk-in closet off the family room and the additional bedrooms and bath located on the opposite side of the home. The attached two-car garage offers excellent potential to be converted into a fourth bedroom, utilizing the existing full bathroom to create a private mother-in-law suite or guest quarters. Additional upgrades include new flooring, trim, doors, fixtures, and fresh interior paint. Create your own outdoor oasis with a newly paved patio and large fenced backyard with room for a pool. Ideally located near downtown Winter Park, Park Avenue shopping and dining, Cady Way Trail, and zoned for top-rated schools. Schedule your showing today!

Listing is courtesy of: SOTERA LIVING (407-725-9660)

Listing Agent: Lisa D'Orazio Llc (813-493-5383)

Remarks: ***MUST SEE WINTER PARK POOL HOME*** Explore the virtual tours to fully appreciate the beauty of this completely renovated 3 bedroom/2 bath solid block pool home nestled in the highly desirable Kenilworth Shores community in Winter Park. This move-in-ready home features an open layout with vaulted ceilings and an abundance of natural light, highlighted by a large free-flowing kitchen with all the amenities... new stainless-steel GE appliances, elegant quartz countertops, sturdy oversized soft-close shaker cabinets and two large built-in wall pantries. The open living area includes a cozy formal dining room with additional countertop seating, and a picturesque sliding glass door opens to an extra-large 40 x 12 outdoor covered porch that provides additional casual outdoor living space. The spacious primary bedroom has a vaulted ceiling and his/her closets, with private access to the backyard covered porch, and features a fully renovated en-suite bath. The secondary bathroom has been tastefully upgraded, as well. Freshly painted inside and out, this immaculate home has new waterproof LVP flooring throughout, new light fixtures and ceiling fans, and stylish window shade coverings on every window. With an indoor laundry room and a two-car carport, this worry-free home features a new AC unit installed in 2025, a new electrical panel and updated plumbing, and a roof that was replaced in 2018. Setting this home apart is your private outdoor private backyard oasis, showcasing a gorgeous 32 ft long/10 ft deep in- ground pool plus a unique outdoor kitchen . . . perfect for family gatherings or hosting a Bar-b-que pool party . . . and with a generously sized 10’ x 18’ shed with full electric providing additional storage solutions or living options, this fully fenced-in backyard is truly a tranquil outdoor haven. Zoned for excellent Winter Park schools, this home is located four blocks from Winter Park High and less than a mile from Brookshire Elementary and Glenridge Middle. It comes with deeded access to the boat ramp and fishing dock at Lake Berry. Blue Jacket Park and Cady Way Park are just down the street, showcasing great bike trails for walking and jogging. The well-known shopping and restaurants of downtown Park Avenue and Baldwin Park are just minutes away. Rollins College, UCF, Full Sail University, and Winter Pines Golf Course are all close by. And Advent Health/Winter Park Hospital is less than a mile down the street. This is a quiet, family-friendly community known for its tranquility and peaceful living. Don’t miss this opportunity to make this wonderful home your very own. Schedule your showing today.

Listing is courtesy of: JAMIESON PROPERTIES, INC. (407-876-2730)

Listing Agent: Joseph Cosgrove (407-470-0892)

Remarks: Located in the heart of Winter Park, Winter Park Pines is a well-established neighborhood known for its convenience, school zoning, and access to outdoor living. A place to slow down, where evening walks feel like something out of a storybook, and the Cady Way Trail is just steps from your back door for morning runs, bike rides, and everything in between. One of the standout features is having the Cady Way pool, pickleball courts, and beach volleyball courts all just a short walk away. The home is zoned for Brookshire Elementary School, Glenridge Middle School, and Winter Park High School, making this location a consistent choice for buyers prioritizing long-term value. In addition to the location, the home benefits from key updates already completed, including a 2022 roof, 2021 HVAC system, updated windows installed in 2017, along with an updated kitchen and bathrooms, offering peace of mind and modern functionality for the next owner. Ideally positioned to enjoy the Winter Park lifestyle. Close proximity to Park Avenue’s boutique shopping and exceptional dining, while the University of Central Florida, Rollins College, and Full Sail University are all within easy reach. AdventHealth Winter Park and Orlando International Airport are also close by, making both daily routines and travel simple. This is a home that delivers on every level, location, lifestyle, and lasting quality.

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

Listing Agent: Melissa Johnson (407-681-4393)

Remarks: One or more photo(s) has been virtually staged. Move-in ready Sylvan Heights Mid-Century Bungalow, with no renovations needed. As you approach, you will notice the wonderfully cared for home with mature landscaping and a unique style. A charming, three-bedroom two-bath home has updated Kitchen and Bathrooms, there is even a large formal dining space with a built-in serving bar and wine fridge. The floors were upgraded with engineered hardwood throughout with tile in both bathrooms. Situated on a larger lot with a fully fenced in backyard that also has a 12x15 brick patio and room to add a swimming pool if desired. Sylvan Heights is one of Winter Park's Primer residential communities, that is close to Advent Health's Winter Park Hospital and top-Rated Rollins College. Just a short bike ride to Park Avenue in Downtown Winter Park with tons of shops and restaurants so you won’t have to go far for fun. Also, just minutes to downtown Orlando, and all of the Central Florida attractions so get the guest room ready for visitors... Sound like a home you would like to see. Schedule a private showing today.

Listing is courtesy of: SUMMERPARK HOMES REALTY LLC (407-603-6320)

Listing Agent: Buddy Jerome, Iii (407-579-9356)

Remarks: Brand new construction luxury home in the heart of Winter Park! This stunning two-story custom residence offers nearly 3,000 sq ft of heated living space with 5 bedrooms and 4 1/2 bathrooms. A soaring two-story foyer creates a dramatic first impression and opens into an expansive great room featuring 12-foot ceilings, wide-plank flooring, and abundant natural light. The family room showcases a custom paneled feature wall with a sleek built-in electric fireplace, creating a striking focal point for the space. The gourmet kitchen is designed for both everyday living and entertaining, highlighted by a large center island with seating, European slab cabinetry, premium hardware, designer countertops, and high-end appliances. Ample storage and a clean modern aesthetic make this kitchen as functional as it is beautiful. Tucked beneath the staircase is a custom wine storage feature, adding a unique luxury detail. The first floor also includes a private guest suite with its own en suite bathroom, perfect for visitors or multi-generational living. A dedicated home office provides a quiet workspace, while the main-floor laundry room adds convenience. Outside, a professionally designed outdoor kitchen extends the living space and creates the perfect setting for year-round entertaining under the Florida sky. Upstairs, the luxurious primary suite serves as a private retreat. The spacious walk-in closet features a fully custom organization system, while the spa-inspired primary bathroom includes a dual-sink vanity, elegant freestanding soaking tub, and oversized walk-in shower with premium tile work. Three additional bedrooms complete the second floor. Two share a beautifully appointed Jack-and-Jill bathroom, while the fourth bedroom features its own private en suite bath, offering flexibility for guests or family members. Located at 240 N. Phelps Avenue, this home places you just minutes from Winter Park’s iconic Park Avenue — a vibrant destination known for its boutique shopping, award-winning restaurants, art galleries, and charming sidewalk cafés. Residents enjoy access to top-rated schools, including Winter Park High School, as well as renowned cultural destinations such as the Morse Museum of American Art and the Polasek Museum. Outdoor lovers will appreciate nearby Central Park, Mead Garden, and the scenic Winter Park Chain of Lakes. Conveniently located near I-4, SR-417, downtown Orlando, Lake Nona Medical City, UCF, and Orlando International Airport, this home offers the perfect balance of luxury, convenience, and the timeless charm that makes Winter Park one of Central Florida’s most sought-after communities. Schedule your private showing today.

Listing is courtesy of: GOLDEN GROUP REALTY LLC (407-990-5905)

Listing Agent: Milena Fernandes (407-990-5905)

Remarks: Under contract-accepting backup offers. Freshly painted 2 Bedroom/2 Bath townhouse-style condo with no neighbors above or below, backing up to a peaceful pond & community amenities. The upstairs/downstairs split-bedroom floor plan offers privacy - ideal for roommates or families. The bright living area features soaring cathedral ceilings, a corner fireplace, and access to a partially covered patio, perfect for entertaining or BBQs. There's abundant storage throughout, including coat, linen, patio, and under-stair space that could be converted into a small office or workout nook. The kitchen comes fully equipped with all appliances, ample cabinet space, and a breakfast bar, while the dining area overlooks the pond and opens to the patio with an additional storage closet. Upstairs, the primary suite includes an en-suite bath, a large walk-in closet, and corner windows that brings in great natural light. The second bedroom is located downstairs and offers dual closets and a ceiling fan. Updated luxury vinyl flooring runs through most of the home, and there is also an in-unit washer/dryer for convenience. Located in the highly desirable Winter Park Villas community, residents enjoy a wide array of amenities including a sparkling pool, clubhouse with fitness center, tennis courts, car wash station, scenic ponds, pet stations. The HOA provides exceptional value by covering roof & exterior maintenance, lawn service, water, trash, sewer, pest control—ensuring truly low-maintenance living. Conveniently located just minutes from Full Sail University, Rollins & Valencia Colleges, approximately 10 minutes from downtown Winter Park. Top-rated schools nearby, this property is an excellent opportunity for both homeowners & investors. Outdoor enthusiasts will also appreciate easy access to the nearby Cady Way Trail, perfect for walking, jogging, or cycling.

Listing is courtesy of: PLATINUM REALTY GROUP FLORIDA INC (407-270-7378)

Listing Agent: Adam Eisen (407-808-6967)

Remarks: Welcome to 1750 Carollee Lane, where timeless charm meets modern luxury. Set on a homesite with desirable southern exposure in the heart of Winter Park, this four-bedroom, 3.5-bath, custom pool and spa residence offers more than 3,200 square feet of thoughtfully updated living space near Park Avenue, the Chain of Lakes and top-rated schools. The fully renovated 2025 kitchen serves as the centerpiece of the home, featuring quartzite countertops, a custom wood hood, Zellige-style backsplash, induction cooktop, oversized workstation sink and an expansive island designed for gathering and entertaining. The first-floor primary suite offers a private retreat with a completely reimagined spa-inspired bath showcasing marble flooring, quartzite surfaces, custom solid wood cabinetry, a freestanding soaking tub and upgraded walk-in shower. Designed for comfort and entertaining, the home also features a dedicated office and an upstairs loft with a custom dry bar and beverage refrigerator. Outdoors, the backyard lives like a private resort-style oasis, complete with a saltwater pool and spa, sun shelf, travertine decking, electronic roll-down screens and a fully equipped outdoor kitchen designed for year-round enjoyment. Lush new backyard landscaping completed in May 2026, including enhanced privacy elements, creates an intimate outdoor setting rarely found this close to the heart of Winter Park. Additional highlights include updated irrigation supported by a private well, a new downstairs HVAC system and a home warranty provided for the buyer at closing. Move-in ready and impeccably maintained, this residence offers refined living in one of Winter Park’s desirable settings.

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Michelle Hochfelder (407-221-5073)