Homes for Sale Near Winter Park High in Winter Park - 207 homes

Remarks: Tucked inside one of Winter Park's most sought-after zip codes, this FULLY RENOVATED two-story condo lives like a townhome — and feels like new construction. The main floor flows from a beautifully updated kitchen with new stainless appliances, contemporary finishes, and butcher block bar top into a bright open living space, with a convenient half bath for guests. Upstairs, both bedrooms are true primary suites — each with its own private en-suite bath, large closet, and oversized window. Major systems have all been replaced: new roof, new plumbing, new hot water heater, and new in-unit Maytag washer and dryer. Step outside to your screened patio just steps from the community pool. Walk to Park Avenue's celebrated restaurants, shops, and cafés. Zoned for Dommerich Elementary (9/10 GreatSchools) and Winter Park High School. This one is genuinely move-in ready — nothing to do but move in.

Listing is courtesy of: NOELKE REALTY (407-607-7166)

Listing Agent: Tom Noelke (407-607-7166)

Remarks: Welcome to one of Winter Park's most impressive move-in-ready homes, where luxury, comfort, and location come together seamlessly. Completely reimagined and renovated, this stunning 4-bedroom, 4-bath residence offers the rare combination of modern construction quality and an established Winter Park location just minutes from Baldwin Park, Park Avenue, Rollins College, and top-rated schools. From the moment you arrive, the circular driveway, modern architecture, and professional landscaping create a memorable first impression. Inside, soaring natural light and oversized porcelain tile floors lead you through an open-concept floor plan designed for both everyday living and entertaining. The heart of the home is an extraordinary chef's kitchen featuring premium Bosch appliances, an oversized quartz island, custom cabinetry, a walk-in pantry, and a stylish wet bar. Whether hosting holiday gatherings or enjoying a quiet morning coffee, this space was designed to bring family together. The private owner's retreat feels like a luxury resort, offering direct pool access, a spa-inspired bathroom, soaking tub, oversized walk-in shower, custom closet, and a private beverage station for added convenience. Step outside and discover what truly sets this property apart. The backyard was designed for Florida living at its finest, featuring a sparkling pool, expansive covered lanai, outdoor dining area, and a fully equipped summer kitchen complete with grill, refrigeration, storage, and sink. It's the perfect setting for family gatherings, weekend entertaining, or relaxing after a long day. A dedicated office, versatile flex room, pool bath, and guest suite provide the flexibility today's buyers demand for work, fitness, hobbies, multigenerational living, or media space. Beyond the home itself, you'll enjoy a lifestyle few locations can match. Walk or bike to nearby parks and trails, spend evenings dining on Park Avenue, explore Baldwin Park's restaurants and shops, and enjoy quick access to Downtown Orlando and Orlando International Airport. With luxury finishes, smart-home upgrades, resort-style outdoor living, and a premier Winter Park address, this is more than a home—it's a lifestyle opportunity rarely available in Kenilworth Shores. Schedule your private showing today and experience the difference for yourself.

Listing is courtesy of: UNITED REAL ESTATE PREFERRED (407-243-8840)

Listing Agent: Courtney Lindsay (206-486-5015)

Remarks: Some homes are updated. Others are completely reimagined. At 2774 Banchory Road, the transformation started with a bold decision: remove the walls and rethink how the home lives. The result is a light-filled great room where the kitchen, dining, and living spaces flow together effortlessly—creating the kind of open, connected lifestyle today's buyers are searching for. The kitchen was designed to be the heart of the home, featuring a dramatic waterfall island, farmhouse sink, quartz countertops, and all-new stainless appliances. Wide-plank flooring runs throughout, while thoughtfully selected RH-inspired lighting adds warmth and character at every turn. Beautifully renovated baths, designer finishes, and thoughtful updates make this home feel both timeless and fresh. Beyond the beautiful finishes, nearly every major component has been improved—from new windows and doors to a new paver driveway, irrigation system, and a recently replaced roof—giving buyers the rare combination of style and peace of mind. Located in Winter Park Pines, one of Winter Park's most beloved neighborhoods, this home offers more than just a beautiful renovation. Residents enjoy zoning for highly regarded Aloma Elementary, Glenridge Middle School, and Winter Park High School, along with a location that's just minutes from Park Avenue, Rollins College, and downtown Winter Park. With easy access to downtown Orlando, you can enjoy the best of both worlds: a charming neighborhood setting with the city's dining, culture, and employment centers just a short drive away. This is what happens when a renovation focuses not just on how a home looks, but on how it lives. Reimagined. Refined. Ready for what's next.

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

Listing Agent: Shelley Dawson (407-492-1900)

Remarks: Discover luxury living in this exquisitely renovated two-story condominium, ideally situated on the third floor of the highly sought-after Douglas Grand in the heart of Winter Park. This elegant three-bedroom, three-and-one-half-bath residence seamlessly blends sophisticated design with everyday comfort. Immediately captivating, the light-filled open floor plan showcases stunning new wide-plank white oak flooring, high ceilings, detailed crown molding, and all-new designer lighting throughout. The chef’s kitchen is a showpiece, featuring crisp white cabinetry, luxurious white quartz countertops, a spacious breakfast bar island, elegant gold hardware, and a built-in desk. A charming breakfast nook offers the perfect setting for morning coffee or casual dining. French doors open to a private enclosed atrium, creating a versatile outdoor retreat ideal for alfresco dining, relaxing, or entertaining guests in style. The expansive living and dining spaces flow effortlessly, while a private first-floor bedroom with en suite bath and walkout balcony provides an ideal space for guests, multigenerational living, or a home office. Upstairs, the primary suite serves as a peaceful sanctuary, complete with an indulgent soaking tub, dual vanities, an oversized walk-in closet, and French doors leading to a large private balcony with sweeping views of Winter Park's iconic Park Avenue—perfect for enjoying sunrise coffee or evening sunsets. A second upstairs en suite bedroom offers its own private bath and generous walk-in closet. Thoughtful features include an upstairs laundry room, a spacious storage closet with potential elevator conversion for future accessibility, and a secure gated garage with two reserved parking spaces. Perfectly positioned in the heart of Winter Park, Douglas Grand places you just steps from Park Avenue, the Winter Park Farmers’ Market, Rollins College, Hannibal Square, Winter Park Golf Course, the Winter Park Tennis Center, Winter Park Village, and an array of renowned dining, shopping, and cultural attractions. Enjoy an unparalleled walkable lifestyle in one of Central Florida's most desirable communities. Notable improvements include an interior renovation (2026), front elevation windows and French doors (2024), interior paint (2024), and HVAC system (2022).

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

Listing Agent: Tiffany Grindstaff (407-252-0927)

Remarks: Virtually Staged. Nestled in the heart of Winter Park, just blocks from Park Avenue and Winter Park Village, this exceptional residence delivers the walkable lifestyle that defines one of Central Florida’s most coveted communities. Leave the car behind and enjoy easy access to award-winning restaurants, boutique shopping, coffee shops, art galleries, Rollins College, the Winter Park Farmers’ Market, and the Chain of Lakes, all just moments from your front door. Built in 2017 by David Weekley, this thoughtfully designed home combines modern luxury with effortless everyday living. Soaring ceilings, oversized windows, and an open-concept floor plan fill the home with natural light and create an inviting atmosphere throughout. The first-floor primary suite offers a private retreat complete with a spa-inspired bath and spacious walk-in closet, while two additional bedrooms, a full bath, and a dedicated laundry room provide flexibility and convenience. Upstairs, the expansive living and entertaining space serves as the heart of the home. The chef’s kitchen is outfitted with custom cabinetry, granite countertops, premium stainless-steel appliances, a large center island, and a natural gas cooktop—perfect for everything from weeknight dinners to hosting friends and family. Sliding glass doors lead to a spacious balcony with new Trex decking, creating the ideal setting for morning coffee, outdoor dining, or evening cocktails overlooking the neighborhood. With professional landscaping maintained by the HOA, this home offers the ultimate low-maintenance, lock-and-leave lifestyle without sacrificing location or luxury. Opportunities to own in such a highly walkable, centrally located Winter Park setting are exceptionally rare. Experience the convenience, charm, and energy of Park Avenue living while enjoying the privacy and comfort of a beautifully appointed residence. This is Winter Park at its finest.

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

Listing Agent: Brandon Geers (941-928-5152)

Remarks: Welcome to 1421 Chapman Circle, an elegant Spanish-Mediterranean home nestled within the highly coveted Windsong community in the heart of Winter Park. From the moment you arrive, the classic barrel tile roof and timeless architectural character set the tone for what awaits inside — a home with enduring style, gracious proportions, and tremendous potential to be personalized for its next chapter. Spanning over 3,500 square feet, this 4-bedroom, 3.5-bath residence offers a formal, well-appointed layout with soaring high ceilings, rich crown molding, and a thoughtful floor plan designed for both comfortable daily living and effortless entertaining. A dedicated first-floor office provides the ideal work-from-home space, while the separate formal dining room adds an air of sophistication perfect for hosting family and friends. The gourmet kitchen is the heart of the home, featuring granite countertops, premium Thermador appliances, and bartop seating — a space equally suited for casual mornings and lively gatherings. The living room opens through French doors to a generous wrap-around screened patio, seamlessly blending indoor and outdoor living in true Florida fashion. The first-floor primary suite is a private retreat, complete with French door access to the patio, a spacious walk-in closet, and a well-appointed en suite bath featuring a double sink vanity, a separate soaking tub, and a walk-in shower. Upstairs, three generously sized guest bedrooms share a hall bath, and a large bonus room and landing offer flexible space for a playroom, media room, or additional lounge area. A large upstairs utility room and additional walk-in storage beneath the stairs ensure that function is never sacrificed. The home is served by two HVAC units, both dated 2017. Beyond the front door, the Windsong community is nothing short of exceptional. Residents enjoy access to two resort-style pools, a splash pad for the little ones, scenic parks, a fishing dock, and coveted chain-of-lakes access complete with use of a community boat — a lifestyle that truly sets Windsong apart. Zoned for A-rated schools and ideally situated just minutes from the vibrant energy of Baldwin Park, Audubon Park, the Mills District, Downtown Orlando, and all that Winter Park has to offer, this address places you at the center of everything. Whether you're drawn to its classic architecture, its unmatched community amenities, or the incredible opportunity to update and truly make it your own, 1421 Chapman Circle is a rare find in one of Central Florida's most beloved neighborhoods.

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

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

Remarks: A striking expression of modern luxury, this brand-new residence offers nearly 3,000 square feet of thoughtfully designed living space in one of Winter Park's most desirable locations. From the moment you step inside, a dramatic two-story foyer and soaring ceilings set the tone for a home that seamlessly blends sophisticated design with everyday comfort. The open-concept living areas are filled with natural light and anchored by a stunning feature wall with a sleek fireplace, creating an inviting space for both intimate gatherings and large-scale entertaining. At the heart of the home, the kitchen showcases a statement island, European-style cabinetry, premium finishes, and quality appliances, while a custom wine display tucked beneath the staircase adds a distinctive architectural touch. Designed with flexibility in mind, the first floor features a private guest suite with en-suite bath, a dedicated home office, and convenient laundry room. Expansive sliding doors open to a fully equipped outdoor kitchen, creating a seamless indoor-outdoor lifestyle perfectly suited to Florida living. Upstairs, the primary suite serves as a private retreat, complete with a custom walk-in closet and spa-inspired bath featuring a freestanding soaking tub, oversized walk-in shower, and elegant finishes throughout. Three additional bedrooms provide exceptional accommodations, including a Jack-and-Jill layout and an additional en-suite bedroom. Ideally positioned just minutes from Park Avenue, residents enjoy effortless access to Winter Park's renowned dining, boutique shopping, cultural attractions, parks, and top-rated schools. Combining exceptional craftsmanship, modern design, and an unbeatable location, this is a rare opportunity to own a brand-new luxury home in the heart of Winter Park.

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

Listing Agent: Nick Mckee (407-913-0171)

Remarks: Culture, Convenience, Community! 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. Near AdventHealth, Cady Way Trail and recreational parks, YMCA of Central Florida, public golf courses, Rollins College, Full Sail University and UCF. Whether you're seeking outdoor adventure, cultural enrichment, or everyday convenience, this location delivers it all. Schedule your private showing today and discover the best of Winter Park living. Roof - 2018, AC - 2015.

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

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

Remarks: Welcome to your fully reimagined Florida home. Among tree-canopied streets in the desired Kenilworth Shores neighborhood, this mid-century modern ranch home was completely transformed in 2005. The redesign added substantial square footage and created a completely unique, functional floor plan that separates it from any other home in the area. Spanning 2,638 square feet of seamless indoor-outdoor living, the property features four bedrooms, 4.5 baths, including three complete en-suite setups that offer maximum privacy for family or guests, plus a dedicated 130-square-foot office. Key property features include elegant design. Step onto gorgeous, rich Brazilian cherry wood flooring that flows beautifully through the open living spaces. Work from home where a dedicated, quiet office space provides an environment for remote work, study or creative projects. Spacious kitchen allows you to enjoy an open-concept floor plan, an eating space in the kitchen, solid wood cabinetry, Silestone countertops and coordinating GE Profile appliances, including a convection oven microwave, giving the kitchen dual oven capacity. Indoor laundry room is a convenient, separate indoor laundry room that keeps household chores organized, quiet and out of sight. Private saltwater oasis allows you to relax in your fully fenced, private backyard featuring an in-ground saltwater pool with spa jets and solar heat. Turnkey infrastructure where peace of mind comes built-in with a new roof (2022), fresh exterior paint and trim (2022), and an updated 200-amp electrical panel. Smart home and systems, equipped with an app-controlled smart security system covering all doors and windows, an EcoBee thermostat and energy-efficient LED recessed lighting. Location and lifestyle benefits include top-tier education, zoned for premier Orange County schools, including Brookshire Elementary, Glenridge Middle School and Winter Park High School (home to a globally recognized International Baccalaureate program). Active recreation to Cady Way Park to enjoy the community pool, playground, sports fields and extensive bike trails. Unbeatable convenience just minutes away from Winter Park Pines Golf Course, two Publix grocery stores, and the upscale dining, boutique shopping, and museums of Park Avenue and Baldwin Park Town Center. This exceptional property blends classic Winter Park lifestyle with the modern infrastructure you demand.

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

Listing Agent: Alison Mosley (407-304-6458)

Remarks: Situated on arguably the finest brick street in Winter Park, beneath a canopy of live oaks, this fully renovated 4-bedroom, 4-bath home delivers the rarest combination: the soul of an established neighborhood, unique charm and character, and the bones of new construction. Gutted to the studs and rebuilt with intention, every major system is new — electrical, Carrier ACs, roof, ductwork, drywall, Pella windows +++. With elevated finishes, like designer tile and quartz countertops as well as floors and beautifully reimagined kitchen and baths. A second-floor addition adds a sprawling 21 x 24 foot private primary suite and home office, one of the many reasons this an ideal setup for MULTIGENERATIONAL families and those who work from home. A welcoming fireplace, lush mature landscaping, butler's pantry, numerous built ins, custom tile work, and an address minutes from Park Avenue make this one of Winter Park's most compelling offerings. Come imagine the possibilities.

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

Listing Agent: Olivia Maxwell (407-222-4440)

Remarks: Newly completed and selected as a showcase residence in the 2026 Parade of Homes, Casa Noir is a custom-built statement home located within one of Winter Park's most desirable pockets and zoned for Audubon Park K-8. From the moment of arrival, the home's striking blend of natural stone, warm white oak, rich textures, and beautifully composed architectural lines creates an unforgettable first impression. Step inside and you're immediately greeted by soaring ceilings, exposed oak beams, wide-plank white oak flooring, and expansive walls of glass that fill the home with natural light. The great room serves as the heart of the residence, anchored by a floor-to-ceiling natural stone fireplace with illuminated built-ins and expansive sliders that seamlessly connect indoor and outdoor living. At the center of the home, you'll find a beautifully executed kitchen designed for both entertaining and everyday living, featuring floor-to-ceiling custom white oak cabinetry, designer stone surfaces, a substantial center island, illuminated wine display, a 48-inch gas range, and abundant storage. Nearby, a walk-in pantry, fully built-out laundry room, and mudroom enhance functionality while maintaining the home's refined design language. Privately positioned on the main level, the dedicated office provides an inspiring setting for work, study, or creativity, while the primary suite serves as a true retreat. The spa-inspired bath is finished with floating oak vanities, rich stone surfaces, a freestanding soaking tub, and an expansive wet room that feels more like a luxurious resort. It's the kind of retreat you'll appreciate every morning and look forward to returning to at the end of each day. Upstairs, a versatile loft creates the perfect setting for a media room, playroom, study space, or secondary gathering area. One bedroom enjoys the privacy of its own ensuite bath and walk-in closet, while two additional bedrooms are connected by a beautifully appointed Jack-and-Jill bath. Step outside and you'll find yourself lingering a little longer than planned. A custom PebbleTec pool, covered tongue-and-groove lanai, fully integrated outdoor kitchen, and private backyard setting create an environment designed for effortless entertaining and low-maintenance enjoyment. Built by Structure Redevelopment, a boutique builder known for delivering thoughtfully crafted custom residences throughout Central Florida. Just minutes from Park Avenue, Rollins College, East End Market, Audubon Park, and Downtown Orlando, Casa Noir brings together exceptional architecture, thoughtful design, and everyday livability in one of Winter Park's most desirable locations - Schedule your tour today.

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

Listing Agent: Ahmad Hassan, Pa (718-641-9358)

Remarks: This new residence, thoughtfully designed by Michael Wenrich, captures the timeless elegance and refined simplicity reminiscent of the iconic coastal architecture of Alys Beach. Clean architectural lines, graceful curves, and abundant natural light combine to create a home that feels sophisticated and inviting. Inside, gorgeous chevron-patterned wood floors flow throughout the main living areas, setting a warm and elegant tone. The open-concept floor plan is designed for everyday living and effortless entertaining, with expansive windows allowing natural sunlight to pour into every space. At the heart of the home is a beautifully designed kitchen that blends classic style with modern functionality. A stunning quartz waterfall island anchors the space, complemented by custom cabinetry and a suite of high-end appliances including an ILVE induction range with six elements and Café French door refrigerator, dishwasher and microwave. Designer-grade lighting and refined finishes elevate the kitchen into a centerpiece of the home. The dining room is filled with light and character, featuring three sets of French doors that open to a charming private front and side courtyard, an ideal setting for morning coffee or intimate outdoor dining. In the living room, a dramatic wall of sliding glass doors connects the interior to the brick patio and backyard, creating a seamless indoor-outdoor lifestyle. The first-floor primary suite offers a peaceful retreat, complete with a spacious walk-in closet and a spa-inspired bath featuring a large glass-enclosed shower, separate soaking tub and dual vanities. Additional conveniences on the main level include a beautifully appointed powder bath, a dedicated laundry room and a generous storage room tucked neatly beneath the staircase. Upstairs, a versatile loft provides additional living space ideal for a media area, office or lounge. Two additional bedrooms are also on the second floor, each featuring custom built-in closets, beautiful designer lighting and abundant natural light. Built with quality and efficiency in mind, the home includes numerous upgrades such as a slate roof, Trane air-conditioning system, Rheem tankless water heater and a two-car attached garage. Ideally just minutes from the renowned shopping and dining of Park Avenue and charm of downtown Winter Park, this exceptional home also offers convenient access to major roadways, Orlando International Airport, leading hospitals, and top-rated public and private schools, bringing together style, comfort and location in one remarkable new construction opportunity.

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

Listing Agent: Mick Night (407-629-4446)

Remarks: In the heart of Winter Park, 1150 Via Salerno is a newly completed Mediterranean-minimalist residence that blends architectural refinement w/ organic warmth. Now offered at a newly adjusted price, the home presents a compelling opportunity to experience design-forward new construction in the Vias neighborhood. Developed and designed by Steve & Jodie Warrick Konold of Scout & Co., the 3,850-sf layout offers 4 bedrooms & 5.5 baths, wrapped in the intentional privacy of a luxury retreat. Beyond its terraced walkway & garden courtyard—envisioned in collaboration w/ architect Cynde Norris—French antique gates open to a native-planted entry garden, creating a soft transition to the interior. A glass foyer introduces a tongue-and-groove ceiling & woven rattan chandelier, sourced & designed in London, leading to a sculptural stairwell positioned just off the main living spaces. The great room features soaring ceilings, a sleek fireplace & walls of glass windows & doors that blur the boundary between inside & out. Ten-inch baseboards meet level 5 drywall in a clean reveal, paired w/ micro-crete flooring on the main level & wide-plank European oak upstairs. In the kitchen, materials w/ function are elevated w/ a Thermadore dual-fuel range, custom plaster hood, full refrigerator & freezer columns & a large island topped in honed black quartzite. The surrounding cabinetry is crafted from hand-carved V-groove panels w/ soft-close hardware & integrated pullout storage. Caesarstone surfaces run along the perimeter while steel-and-glass open shelving w/ a sculptural black sconce balance the composition. A vintage chandelier from Prize Home & Garden sourced in Round Top completes the room. The primary suite occupies a private wing on the main floor accessed via antique gallery doors that lead to the rear courtyard. Vaulted ceilings, a custom walk-in closet w/ a spa-like bath provide a luxurious retreat. Features include a long double vanity, matte black Kohler fixtures, a freestanding tub, walk-in shower w/ built-in bench & separate water closet. On the mezzanine level, the powder bath makes a dramatic statement w/ a floating black quartzite trough sink w/ handwoven mirror. Across the hall, the laundry room blends beauty w/ utility w/ custom cabinetry, matching quartzite surfaces, matte black fixtures & a side-by-side front-load washer & dryer. A nearby guest suite is marked by an antique door entry. The en-suite bath features a hand-painted tile threshold & suede-framed mirror. Two upstairs bedroom suites feature en-suite baths, designer lighting, distinctive mirrors & continuous European oak flooring. Positioned at the front of the home, the rooftop terrace is accessible via the upper hallway. The detached casita opens to the pool courtyard through accordion glass doors & features micro-crete floors, a woven rattan chandelier & a full bath—ideal as a studio, gym or office. Outdoor spaces include two garden courtyards, a fully fenced backyard, a heated saltwater pool & a rooftop terrace, all enclosed by masonry walls & a board-on-board privacy fence. Additional features include a lower-level two-car garage, storage closet, 3 HVAC systems, Rinnai tankless water heater, Sierra Pacific windows, customized closets, solid core interior doors, 6” round gutters & a Barcelona barrel tile roof. Thoughtfully designed & beautifully executed, 1150 Via Salerno offers a refined lifestyle tucked within one of Winter Park’s most exclusive enclaves.

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

Listing Agent: Padgett Mccormick (407-645-4321)

Remarks: Resort Style Pool Home in KENILWORTH ESTATES! Conveniently located in Winter Park with a walking distance to Baldwin Park, Advent Health, Cody trail park! A short drive to Rollin College, Park Ave, Full Sail University, downtown Orlando, theme parks, and UCF! Close to restaurants, shopping centers, bars, Publix, CVS and gas stations. Welcome Home! through the main door, you will be amazed by its modern and spacious floor plan! A lovely living room with a fireplace, an extra room for home gym or office, on the right, a sparkling pool in front of your eyesight through a modern glass sliding door, sitting under porch, enjoying family gathering in this resort style garden! There are plenty closet spaces for storage! Spacious kitchen cabinets for cooking supplies. Be ready to live in a luxury and breath-taking Winter Park Pool home, while enjoying all Florida sunshine and outdoor biking, jogging and golfing at Winter Park Pine. House was repiped in 2021, Brand-new roof in 2023, Newer AC, like-new hot water heater! Entire home was renovated, new paints, new pool filter, new cabinets and appliances. Are you ready living in your dream home! Move in KENILWORTH ESTATES home today!

Listing is courtesy of: EXPLORE FLORIDA REALTY SERVICES LLC (407-982-9709)

Listing Agent: Shannon Lee (407-982-9709)

Remarks: Vilasa Homes — Winter Park’s Expression of Modern Luxury. Perfectly positioned just steps from Park Avenue, this architecturally stunning residence blends refined design with the effortless elegance of Winter Park living. Crafted by Nasrallah Architectural Group, Ted Maines Interiors, and Jordan Builders, this home showcases an Alys Beach–inspired aesthetic with warm wood accents, wrought iron detailing, and two-story block construction for enduring quality. Interiors exude sophistication: soaring 13' ceilings on the main level, 10' upstairs, level-four wall finishes, all-wood flooring, Pella double pain windows and curated designer lighting. The chef’s kitchen is a showpiece— high-end flat panel cabinetry, quartz surfaces, Thermador appliances, and an expansive quartz waterfall island overlooking lush greenery. A private in-unit elevator provides effortless access to the second-floor, enhancing both convenience and sophistication. The second-floor primary retreat offers a serene escape with a loft for office or wellness space, a spa-caliber bath with soaking tub and oversized shower, and generous closet options. Two additional bedrooms provide versatile accommodation for guests, a private office, or fitness space, complemented by a thoughtfully designed shared bath. Outdoor living is exceptional with an expansive 40' x 20' private fenced-in backyard, including a covered patio which extends from the sliding glass doors. A 2-car garage with insulated doors completes the residence. Moments from Winter Park’s finest dining, boutiques, museums, lakes, Hannibal Square and Rollins College. Vilasa Homes offers a rare opportunity to live at the center of it all—wrapped in luxury, design, and timeless style.

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

Listing Agent: Carmen Quintana (407-340-3932)

Remarks: Nestled on one of Winter Park’s most exclusive streets, this exceptional residence is located within Park Place—the only gated neighborhood in the coveted 32789 ZIP code—and is zoned for highly sought-after Audubon Park K–8 School. From the moment you arrive, you'll appreciate the rare combination of privacy, charm, and convenience that defines this remarkable home. Designed with both everyday living and effortless entertaining in mind, the versatile floor plan features elegant formal living and dining rooms, creating a welcoming setting for gatherings both large and small. The spacious primary suite is conveniently located on the first floor, along with a secondary bedroom ideal for guests or multigenerational living. Upstairs, you'll find two additional bedrooms, a full bath, and a generous bonus room perfect for a home office, media room, playroom, or fitness space. At the heart of the home is a beautifully appointed kitchen featuring granite countertops, crisp white cabinetry, a center island, and a sunlit breakfast nook surrounded by windows. The kitchen flows seamlessly into the inviting family room, where custom built-ins, a cozy fireplace, and French doors create the perfect blend of comfort and sophistication. Step outside to your own private Florida oasis. The covered paver lanai, summer kitchen, and sparkling saltwater pool provide an ideal backdrop for year-round entertaining, weekend gatherings, or peaceful evenings at home. Rich hardwood floors extend throughout the entire residence—there’s not a stitch of carpet anywhere. Architectural details such as crown molding, plantation shutters, 10-foot ceilings, and 8-foot doors enhance the home’s timeless elegance and spacious feel. Additional conveniences include a first-floor laundry room with pantry storage and a guest powder bath. A standout feature is the oversized detached two-car garage, complete with a private upstairs studio and full bath—perfect for a home office, guest suite or creative space. Surrounded by lush professional landscaping and shaded by magnificent mature oak trees, the fully fenced backyard offers beauty, privacy, and natural cooling throughout Florida’s warmer months. Tucked away on a quiet cul-de-sac, the property also benefits from added privacy provided by the neighborhood’s surrounding brick wall and direct access to a nearby open field. Park Place is more than a neighborhood—it’s a rare opportunity to enjoy a secure, friendly lifestyle.

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

Listing Agent: John Mcdade (407-721-7275)

Remarks: Winter Park lakefront home! A rare opportunity to own a thoughtfully renovated mid century lakefront residence in Winter Park. This three bedroom four bath home offers stunning views, high ceilings and abundant natural light. The open layout flows effortlessly for everyday living and gatherings with friends and family. As you walk through the front door, you will be drawn to the large living area and a wall of windows and doors leading to the lake. The island kitchen is a cook's dream with abundant workspace and welcoming island seating. Imagine waking up every morning to yet another amazing view- The primary suite is spacious and private with newer bath and large walk- in closet. Nicely appointed secondary bedrooms and updated baths. In addition to the main living area, there is a separate oversized family room with a full bath adjacent. This home was completely renovated and expanded in 2013 creating a perfect blend of timeless architecture and carefully designed updates. Other features include two car garage with "glass" overhead doors and mini-split HVAC, metal roof, generous closets & storage throughout and recently installed sod. What makes this house truly special is the setting on Lake Spier- a ski lake tucked away in a secluded part of Old Winter Park . There are no homes across the lake- so spending time on the patio and dock offers an expansive view of water and trees and a remarkable sense of privacy. Inside and out, every space feels connected to the natural beauty. Great location to enjoy Winter Park living. Ideally situated near top rated schools - Baldwin Park, Glenridge and Winter Park High School. Enjoy close proximity to walking trails, restaurants and shopping. This home is truly special!

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

Listing Agent: Nicole Seybold (407-808-9374)

Remarks: Situated in the heart of Winter Park, this custom-built Mediterranean-style estate offers an exquisite living experience that marries timeless architecture with modern innovation. A dramatic grand foyer introduces a residence where every finish has been meticulously curated, from Turkish travertine stone and rich wood flooring to Brizo hardware in Brilliance Polished Gold. At the heart of the home, the chef’s kitchen blends elegance and function with gleaming stainless steel appliances, crisp white cabinetry, granite countertops, and a well-appointed Butler’s pantry with a dedicated bar, creating a sophisticated setting for effortless entertaining. Integrated smart features further elevate daily living, including an intercom system for seamless communication, electronic blackout curtains for instant privacy and ambiance, and thoughtful, layered lighting throughout. The magazine-worthy primary bath—featured in Florida Home—feels like a private spa retreat, with floor-to-ceiling back-lit mirrors, a self-cleaning smart toilet with bidet, a custom Barclay soaking tub with black matte exterior, and Calcutta gold marble countertops and backsplash. These luxe finishes are anchored by an oversized chevron pattern tile by Crossville in Ice White, a throwback diamond-pattern shower floor, and a sculptural Kuzco LED chandelier that completes the space with dramatic flair. Expansive living areas open to resort-inspired outdoor spaces where a heated saltwater pool and spa, private mini-golf green, and a summer kitchen with tongue-and-groove wood ceiling create a true indoor-outdoor sanctuary. Velux solar-powered skylights with acoustic rain sensors that automatically close at the first sign of rain, a Mosquito NIX misting system, comprehensive surveillance, and electronic private gated access provide both comfort and peace of mind. Natural gas service and a dedicated hook-up for a whole-house generator underscore the home’s emphasis on performance and preparedness. Crafted for those who expect uncompromising quality, this Winter Park residence is more than a home—it is a refined sanctuary where architectural presence, rich materiality, and thoughtful technology converge in one coveted address.

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

Listing Agent: Robyn Brehne-Glass (407-474-4038)

Remarks: Virtually Staged. *** JUST REDUCED TO $625,000 | 1830 Edwin Blvd, Winter Park, FL 32789*** This is your moment. One of Winter Park's most beautifully RENOVATED and MOVE-IN READY homes has just been repriced, and at $625,000, it will not last long. From the moment you step inside, you are welcomed by an open, airy layout with soaring VAULTED CEILINGS that make the home feel expansive and inviting. Gorgeous TILE FLOORING flows seamlessly throughout every room, while natural light floods the space through DOUBLE-PANED WINDOWS (2018) and remote-controlled German Velux SKYLIGHTS (2021), creating an atmosphere that simply feels good to be in. The thoughtfully designed floor plan connects the living, dining, and kitchen areas in a way that is as functional as it is beautiful, making it ideal for everyday living and effortless entertaining. At the heart of the home, the stunning CUSTOM EUROPEAN-STYLE KITCHEN is a true showpiece, featuring premium Cambria quartz countertops (2025) and top-of-the-line appliances including a NEW refrigerator (2025), BOSCH dishwasher (2024), and Maytag microwave (2022). This kitchen was designed to impress and built to perform. Both bathrooms have been FULLY REMODELED with sleek modern finishes and NEW VANITIES (2025). All interior doors were replaced (2017), and every detail has been carefully considered to deliver a home that feels truly turnkey from top to bottom. For peace of mind, major systems have all been upgraded. A high-efficiency Amana AC with smart thermostat (2024), a tankless water heater (2025), a complete PEX plumbing upgrade to the city connection (2025), modernized PVC drain lines in the bathrooms, laundry and kitchen (2025), new sinks and faucets (2025), and updated kitchen electrical wiring to current code (2025) mean you can move in with complete confidence. NEW ROOF (2021). Step outside to your own private retreat. A fenced backyard (2018) and screened patio (2022) create the perfect space for relaxing or entertaining year-round. Driveway pavers (2024), a carport (2024), and an OVERSIZED Tuff Shed (2024) round out an exterior that is just as polished as the interior. Smart home features including electronic front door locks (2023), a smart ceiling fan (2023), and smart kitchen lighting (2025) add a layer of modern convenience that ties it all together beautifully. And the location? Simply unbeatable. Just minutes from the legendary Park Avenue, and within walking distance to premier shopping, dining, parks, and everyday conveniences, this home places you right in the heart of everything Winter Park has to offer. Location. Layout. Quality. This home has it all, and now at a price that reflects real value in today's market. Opportunities like this do not come around often. *** SCHEDULE YOUR SHOWING TODAY BEFORE IT IS GONE! ***

Listing is courtesy of: ZEN LIVING HOMES LLC (407-800-2717)

Listing Agent: Nydia Marrero (407-620-6221)

Remarks: Virtually Staged. **Price Improvement** Welcome home to this beautifully updated two-story end-unit, ideally located just steps from Michelin-star dining, local boutiques, and the vibrant East End Market. On weekends, enjoy leisurely strolls to the area’s popular farmers markets and neighborhood events. Situated in the heart of Winter Park, this residence offers the perfect blend of lifestyle, convenience, and charm in one of Orlando’s most sought-after communities. Designed for both everyday comfort and effortless entertaining, the first floor features an open-concept kitchen and living area filled with abundant natural light, along with a convenient half bath—ideal for hosting guests. Upstairs, the spacious primary suite boasts a private ensuite bathroom, walk-in closet, and a newly refinished balcony—perfect for morning coffee or evening cocktails. Two additional bedrooms provide generous space and share access to a second balcony, creating a seamless indoor-outdoor living experience. Recent upgrades include a new dishwasher and smart refrigerator (2022), new water heater (2025), refinished front balcony (2025), new roof, and new carpet upstairs (2026). Updated light fixtures and primary bedroom flooring within the last five years add a modern touch throughout. The $400 monthly HOA fee includes landscaping and insurance, offering low-maintenance living and added peace of mind. Zoned for some of Orlando’s top-rated schools and walking distance from the new Audubon Park K-8 School, this home presents a rare opportunity to enjoy the very best of Winter Park living. Don’t miss your chance to call this exceptional property home.

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

Listing Agent: Courtney Dietch (407-952-3779)