Homes for Sale Near Winter Park High in Winter Park - 217 homes

Remarks: Beautifully built in 2022 by Lonnie Richardson, this custom one-story home sits on a quiet cul-de-sac in the heart of Winter Park. Designed with a modern, timeless style, it offers luxury finishes paired with a warm, comfortable feel. The home features 4,060 square feet, including four en-suite bedrooms, five full bathrooms, a powder bath, and a bonus room with a built-in office. The spacious gourmet kitchen overlooks the main living areas and pool, and is equipped with premium Wolf appliances and a separate chef’s kitchen for added convenience. Enjoy seamless indoor-outdoor living with a covered lanai featuring motorized screens, heaters, and a mosquito misting system. The outdoor space also includes a summer kitchen, gas fire pit, and a pool equipped with a swim jet system that creates a continuous current, effectively transforming it into an endless lap pool. A detached fitness studio with a steam shower provides a private wellness retreat. Additional highlights include custom built-ins, engineered hardwood floors and surround sound throughout. The oversized two-car garage offers epoxy flooring, custom storage, and a dog wash station. Irrigation is supplied by a private well, and the home also features underground utilities and a full security system. The exterior is designed for both beauty and low maintenance, with manicured landscaping and artificial turf that stays lush year-round. With no HOA, added privacy, and exceptional attention to detail throughout, this home offers a rare opportunity to experience luxury living at its finest. This home is conveniently located near the Enzian Theater and less than a mile from Winter Park Village, with top-rated schools nearby, this home combines comfort, style and an unbeatable location. Schedule your private showing today.

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

Listing Agent: Damian Bergler (650-398-5968)

Remarks: Park Hill is one of Winter Park's most coveted addresses, a distinguished collection of luxury brownstones situated at the northern end of Park Avenue, moments from the city's finest boutiques, restaurants, cultural landmarks and the historic Winter Park Golf Course. Within this exclusive enclave, residence 649 occupies one of the community's most private settings. Beyond the stately brick courtyard and gas lantern-adorned entrance, this three-story home with a private elevator is thoughtfully scaled for refined living. Not oversized, but extraordinarily well-appointed. Ten-foot ceilings, intricate millwork and moldings and generous windows establish an ambiance of quiet elegance, while hardwood floors and designer fixtures carry that standard throughout. The open-concept main living area is built for effortless entertaining. The chef's kitchen features Wolf and Sub-Zero appliances, custom wood cabinetry, marble accents, a center island with bar seating and a wet bar with a beverage refrigerator and ice maker. The space opens directly to a private courtyard with a summer kitchen and dedicated alfresco dining area, creating a genuinely tranquil retreat that feels removed from the energy of the avenue. Upstairs, two guest suites each offer walk-in closets and en-suite baths. A dedicated laundry room and a covered terrace with a fireplace, wet bar and half bath complete the level. The third-floor primary suite provides a true sense of retreat, with two custom walk-in closets, a private balcony and a spa bath filled with natural light from windows and skylights. Dual vanities, a glass-enclosed steam shower and a soaking tub are finished throughout in premium materials. Constructed of Old Carolina brick with three-story block construction, precast exterior trim and a slate mansard roof, the residence features a two-car air-conditioned garage, ample storage and soundproof hollow core floors. With exterior maintenance managed by the association, the lifestyle here is genuinely lock-and-leave. This is a rare opportunity to own in one of Central Florida's most prestigious communities, in a location that simply cannot be replicated.

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

Listing Agent: Drew Henner (407-406-0662)

Remarks: Under contract-accepting backup offers. Built for long-term ownership rather than short-term resale, this custom-built Brookshire Heights residence offers a rare combination of thoughtful design, exceptional construction quality, and nearly 4,000 square feet of living space in one of Winter Park's most beloved neighborhoods. Unlike many homes that have been renovated or recently built for resale, 2465 Banchory Road was designed from the ground up with intention, combining timeless architecture, functional luxury, and quality craftsmanship throughout. Set on one of the most beautiful streets in Winter Park, where evening walks feel like something out of a storybook and the Cady Way Trail is just steps from your front door, this home offers the lifestyle buyers dream about and the quality they rarely find. A grand mahogany front door welcomes you inside, where soaring ceilings, oversized interior and exterior doors, and spacious living areas create a sense of elegance and comfort from the moment you enter. The thoughtfully designed floor plan offers nearly 4,000 square feet of living space, including four bedrooms, four full en-suite bathrooms, and a dedicated pool bath. One of the home's most unique features is its dual primary suites, with one located on the first floor and another upstairs. This flexible layout is ideal for multigenerational living, long-term guests, private retreats, or evolving lifestyle needs. Two additional bedrooms each feature their own private en-suite bathroom, while a generous upstairs flex space offers endless possibilities as a media room, playroom, home office, gym, or potential fifth bedroom. The kitchen was designed for both everyday living and entertaining, featuring premium cabinetry, a gas cooktop, double ovens, a built-in coffee system, and a built-in steamer. Every detail was selected to combine beauty, functionality, and convenience. Step outside to a resort-style backyard where the pool becomes the centerpiece of outdoor living. The dark pebble finish, sun shelf with bubblers, color lighting, natural gas heater, automated controls, and expansive outdoor entertaining space create an experience that feels more like a private resort than a backyard. Beyond what you can see, the home's construction quality truly sets it apart. Dual 19-SEER HVAC systems with independent WiFi controls, natural gas service, insulated floor systems between levels, a whole-home instant hot water system, insulated low-E windows, and a hurricane-rated insulated garage door reflect the level of planning and investment rarely found in today's market. These are the kinds of features that enhance comfort, efficiency, and long-term value for years to come. Perfectly positioned for the Winter Park lifestyle, you'll enjoy easy access to Cady Way Park, tennis and pickleball courts, playgrounds, Park Avenue's boutiques and dining, Rollins College, Full Sail University, UCF, AdventHealth Winter Park, and Orlando International Airport. Zoned for top-rated Winter Park schools. This is more than a beautiful home. It is a true custom residence built with intention, designed for living well, and positioned in one of Winter Park's most desirable neighborhoods.

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

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

Remarks: Attention Students & Parents! Updated First-Floor Corner Condo directly across the street from the Full Sail campus! Why rent when you can buy! 2 Bed | 2 Bath | 1,105 Sq. Ft., an updated first-floor northwest corner condo. -Brand-New Kitchen Appliances: Convection oven, refrigerator, dishwasher, and microwave -Interior Laundry Room with new LG stackable washer & dryer -New Air Conditioning System -Updated Kitchen Cabinets -Updated Plumbing & Electrical -New Ceiling Fans Throughout -Fresh Interior Paint -New Carpet in Bedrooms Community Features: Private screened patio Community pool and hot tub Beautifully maintained grounds Pet-friendly and fenced dog park Winter Park School District, zoned for A-rated schools, approximately 1 mile away.

Listing is courtesy of: FLATFEE.COM (954-965-3990)

Listing Agent: Cliff Glansen

Remarks: Under contract-accepting backup offers. 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: Under contract-accepting backup offers. ***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: Nestled along one of Winter Park's most cherished brick-lined streets, this elegantly appointed two-bedroom, two-bath residence at the prestigious Alabama offers a rare opportunity to experience the very best of lakeside luxury living. With 1,574 square feet of thoughtfully designed interior space, this exceptional unit captures the timeless charm and sophistication that have made the Alabama one of the most coveted addresses in the heart of Winter Park. From the moment you step through the gracious foyer entry, complete with a coat closet, you are welcomed by an atmosphere of warmth and refined taste. Reclaimed wood floors flow seamlessly throughout the entire residence, lending an organic richness that perfectly complements the grass cloth covered walls and classic crown molding found in every room. Recessed lighting adds a soft, curated ambiance, while the expansive living and dining area serves as the heart of the home, offering sweeping views of the beautifully maintained gardens and the shimmering waters of Lake Maitland just beyond. The well-appointed kitchen is a chef's delight, featuring stainless steel appliances, an induction range, a Subzero refrigerator, stone countertops, a charming penny tile backsplash, and a central island ideal for both casual dining and entertaining. A dedicated interior laundry room adds a layer of everyday convenience that is rarely found in residences of this era and character. The primary bedroom is a true retreat, featuring double built-in closets and a beautifully finished en suite bath with a walk-in shower. The second bedroom is comfortably proportioned and well-suited for guests, a home office, or whatever lifestyle demands require. The hall bath offers a classic tub and shower combination to serve residents and visitors alike. One reserved covered parking space is included, and monthly HOA dues of $1,600 cover the care and maintenance that keep this distinguished property in impeccable condition. The location is simply unmatched. Kraft Azalea Park, one of Central Florida's most scenic and beloved green spaces along the shores of Lake Maitland, is just moments away, offering a tranquil setting for morning walks and golden-hour evenings. The legendary shops, restaurants, and galleries of Park Avenue are easily accessible, placing world-class dining and boutique retail practically at your doorstep. Tennis enthusiasts will appreciate the proximity to the Winter Park Racquet Club, while golf aficionados will find the storied Interlachen Country Club well within reach, rounding out a lifestyle that is as active as it is refined. This is Winter Park living at its most authentic, offering history, elegance, and an unbeatable sense of place in one of the most desirable communities in all of Central Florida.

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

Listing Agent: Kelly Price (407-645-4321)

Remarks: Tremendous value in the land. Well cared for vintage Winter Park home that has 3 BEDROOM and two bath rooms. Potential to remodel, improve and expand or simply tear down to build a new custom home. However, this home is move in ready! There is not an HOA. 1343 total square feet and 1186 heated square feet. Newer DUAL-PANE WINDOWS! New HVAC system in NOvember 2025. Home was replumbed in 2024. SEPTIC PUMP OUT, OCT 2025. No carpeting instead there is SOLID FLOORING THROUGHOUT: WOOD PARQUET, TILE, LUXURY VINYL PLANK. The kitchen has been updated with SOLID WOOD KITCHEN CABINETS + GRANITE COUNTER TOPS and newer MATCHING APPLIANCES. The home has INDOOR WASHER/DRYER and a working fireplace. The back yard is FULLY FENCED. Local top rated CITY OF WINTER PARK SCHOOLS. And CITY OF WINTER PARK UTILITIES. The land, the lot have a fantastic upside. BOTH NEXT DOOR (WEST SIDE) AND REAR (NORTH SIDE) NEIGHBORING LOTS HAVE BEEN EMPTY FOR SEVERAL YEARS. This is a great investment and the property itself offers excellent rental income. Think "down the road" value + immediate return value.

Listing is courtesy of: GALLOWAY REAL ESTATE (407-421-9990)

Listing Agent: Sidney Galloway (407-421-9990)

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: Welcome to easy living in the heart of Winter Park. Located just two blocks from Park Avenue, this studio condo puts you right in the center of it all—award-winning restaurants, boutique shopping, coffee shops, museums, and the iconic Winter Park boat tour are all just steps away. Situated on the third floor of Building 6 with convenient elevator access, this light-filled unit offers a surprisingly flexible layout. The current owner has creatively configured the space with separate living and dining areas, while the enclosed porch serves as a bedroom. The updated kitchen features decorative tile flooring, stainless steel appliances, and solid wood cabinetry. Sliding glass doors lead to a bonus room that can easily function as a home office, guest space, workout room, or additional living area. The bathroom includes a single vanity and tub/shower combination, and you'll appreciate the abundance of storage throughout the unit. One of the biggest advantages of this property is the peace of mind that comes with a monthly HOA fee that covers nearly everything—including electric, water, sewer, trash, building insurance, landscaping, pool maintenance, and on-site management. . Whispering Waters recently passed its structural integrity inspection and reserve study with excellent results, reflecting the care and quality of this well-managed community. Residents also enjoy access to beautiful Lake Osceola, where you can launch a kayak, relax by the water, or take in breathtaking sunset views. Whether you're looking for a full-time residence or a seasonal retreat this condo offers an unbeatable Winter Park location and true lock-and-leave convenience.

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

Listing Agent: Andrea Parra Chopite, Pa (407-515-0097)

Remarks: Positioned on a quiet canal, this exceptional property features a covered boat dock with lift, offering effortless access to the renowned Winter Park Chain of Lakes. This home, built by Liberty Development, with 4-bedrooms plus two bonus rooms blends elegance with comfortable everyday living. The main level offers a dedicated office area, formal dining room, and an inviting gathering room with gas fireplace, all flowing seamlessly into the stunning chef’s kitchen. Designed for entertaining, the kitchen features two large islands, exotic granite countertops, under-cabinet lighting, and premium Thermador appliances including a 6-burner gas range with griddle. The walk-in butler’s pantry has a beverage cooler and ice maker adds both style and functionality. The adjoining breakfast area is framed by grand windows overlooking the pool, cabana, and canal. The luxurious downstairs primary suite enjoys tranquil water views and a spa-inspired bath with travertine stone floors, marble counters, custom cabinetry, soaking tub, walk-in shower with steam and generous closet space. Upstairs you’ll find three additional bedrooms and a spacious bonus room, while a separate bonus suite above the garage provides future space for a media room, gym or guest retreat. The interior of the home is highlighted by hardwood floors, plantation shutters, decorative moldings and designer lighting throughout. The outdoor living area is equally impressive. French doors open to a covered porch with classic Old Winter Park brick, leading to a travertine-surrounded pool and private cabana with a wood-burning fireplace. Exterior highlights include a metal roof, durable cement board siding and wooden shutters. Don’t miss this limited opportunity to have immediate and easy access to the coveted Winter Park Chain of Lakes. *Some photos have been virtually staged*

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

Listing Agent: Johnny Hurlburt (407-579-3168)

Remarks: Welcome to this stylishly renovated ranch-style pool home in Kenilworth Shores, 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. Other notable additions over the years include a metal roof, irrigation on well, 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: Built in 2018, this beautifully designed 4-bedroom, 3.5-bath home offers 2,843 square feet of refined living in a prime Winter Park location, walking distance to Park Avenue and the renowned Winter Park 9 golf course. Thoughtful architectural details set it apart, including shiplap ceilings in the living room and kitchen, decorative ceiling finishes in the bedrooms, and a striking tile staircase wall enhanced by natural light. The open-concept layout centers around a chef’s kitchen with Wolf and Sub-Zero appliances, custom cabinetry, and Kohler fixtures—perfect for everyday living and entertaining. The primary suite features a spa-inspired bath with a marble shower, while secondary baths include Kohler and Rohl fixtures. An upstairs bonus room adds flexible living space. Enjoy a private pool, oversized two-car garage with storage, and an extended driveway for ample guest parking. Additional features include dual Carrier HVAC systems, custom window treatments, and elegant Bevolo gas lanterns that create a warm, upscale presence at night. This home offers a rare combination of style, comfort, and walkable convenience in one of Winter Park’s most desirable areas.

Listing is courtesy of: FLORIDA CAPITAL REALTY (786-953-5870)

Listing Agent: Jacob Theisen (407-908-1735)

Remarks: Rare opportunity to own a beautifully upgraded lakefront property on half acre in one of Winter Park's most desirable locations. This homesite offers the perfect setting to enjoy the current residence or build your future dream home! When you step inside you'll find a thoughtfully updated kitchen featuring high-end appliances, custom cabinetry, and designer finishes. The home boasts new windows that fill the space with natural light and frame serene lake views, as well as a brand new roof and AC offering peace of mind for years to come. Split floor plan with 3 large bedrooms and each has a walk-in closet. Step outside and take in the beautifully landscaped yard, complete with mature trees and plenty of space and privacy. Whether you’re sipping coffee by the water or hosting friends for a sunset BBQ, this home is made for living the good life! Zoned for A rated schools. Situated on a quiet street yet just minutes from Winter Park and Baldwin Park dining, shopping, parks and culture. Call today before it's gone!

Listing is courtesy of: TAL BUSIDAN PA (407-227-3001)

Listing Agent: Tal Busidan (407-227-3001)

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: Under contract-accepting backup offers. 3 bedrooms PLUS an office (or 4th bedroom) AND a "flex space". Easy access to all of Winter Park, UCF, and south Seminole County from this convenient, central location! If you've been searching for a spacious pool home with plenty of space for playing, entertaining, or even working from home -- you've found it here! When you walk in, you'll appreciate the intuitive flow of living space into the kitchen, with built-in eating space. Off of the kitchen, you'll find a bonus space (perfect for an office or home gym) as well as a large indoor laundry room/mudroom, and the converted garage which is ideal for a playroom or secondary living space. On the other side of the home, 2 secondary bedrooms, an oversized hall bathroom, and a primary with en suite bath. There are additional touches that go a long way, too, including the custom plantation shutters throughout the home and updated countertops in the kitchen. Much of your time will be spent in the backyard, enjoying a fenced in pool, screened porch, new custom shed (2025), and fully fenced yard with turf play area. Systems in the home have been well maintained: roof (2017), HVAC (2017), tankless gas water heater (2018), and brand new electrical updates (2026). The home was also re-plumbed in 2008.

Listing is courtesy of: MILLER GRANT AND COMPANY (407-399-6031)

Listing Agent: Courtney Pelfrey (407-454-0538)

Remarks: Remodeled pool home located in the highly sought after desirable Winter Park school district. This property has a.27 acre corner lot with room to expand and a pool/spa perfect for relaxing or entertaining guest.Inside the living room features vaulted ceilings that create a bright open feeling and a huge screened in patio for outdoor entertaining. The bathrooms have been beautifully remodeled, there are new windows, new electric outlets throughout, new light fixtures, roof replaced in 2022,kitchen beautifully redone 2020 with new cabinets and Granite counter tops. Additional upgrades throughout the home include new luxury vinyl flooring, new vanity in master bath, new enhanced pool liner, new robot pool vacuum, new garage door house has been painted inside and out. The location is close to shopping, Costco and other stores also located near by. Full Sale, Rollins College and downtown Winter Park to the west and UCF to the East within close proximity. This is a must see. Owner is realtor.Buyer to verify room measurements.

Listing is courtesy of: JC FLORIDA REALTY LLC (407-257-8265)

Listing Agent: Eva Firios (321-662-1501)

Remarks: Experience elevated living in this fully transformed luxury residence in the heart of Winter Park, where design, premium finishes, and effortless functionality come together seamlessly. This 3-bedroom, 3.5-bath pool home offers approximately 2,400 square feet of impeccably curated living space, designed for those who appreciate both style and substance. Expertly designed by Morrone Interiors, every detail reflects a refined, cohesive aesthetic. Step inside to warm oak wood floors and a light-filled open-concept layout ideal for both everyday living and upscale entertaining. The chef’s kitchen is a true statement, featuring custom oak cabinetry, sleek quartz countertops with a dramatic waterfall island, and an expansive breakfast bar. Top-of-the-line appliances include a Sub-Zero refrigerator, Wolf 6-burner gas professional range with grill and double ovens, Wolf microwave, Miele dishwasher with PowerDisk system, and a built-in Miele coffee station. The kitchen flows effortlessly into both a breakfast nook and a separate dining area, while the designer bar serves as a stunning focal point—complete with two Sub-Zero dual zone wine refrigerators accommodating more than 200 bottles, along with additional Sub-Zero refrigerator and freezer drawers. Downstairs all blinds are motorized and have gorgeous custom drapes. Upstairs, all three bedrooms are en suite, offering a private retreat for family and guests. A versatile loft area features a custom-designed laundry space concealed behind built-in cabinetry for a clean, streamlined aesthetic. One bedroom has been thoughtfully designed as a home office with a built-in Murphy bed, providing flexibility without compromising luxury. The outdoor space is equally refined, featuring low-maintenance turf, a beautifully designed pool, and a covered lanai perfect for relaxing or entertaining. A built-in grill area and lush privacy hedging create a serene backyard oasis, with landscaping professionally designed and maintained by Signature Landscaping. Additional highlights include a 2-car garage and a Sonos sound system in the living room and lanai, enhancing the home’s elevated lifestyle experience. Most furnishings are available for purchase separately, offering a truly turnkey, designer-furnished opportunity. Ideally located just minutes from Park Avenue, top-rated schools,Rollins College, fine dining, and boutique shopping, this exceptional home represents the very best of Winter Park luxury living. Perfect lock and leave home with the perfect location!

Listing is courtesy of: OLDE TOWN BROKERS INC (407-425-5069)

Listing Agent: Noelle Leblanc (407-491-2744)