Homes for Sale Near Maitland Middle in Winter Park - 75 homes

Remarks: Masterclass in Modern Luxury on Alabama Drive 3 Beds | 3 Baths | Premier Corner Lot | Winter Park, FL Nestled on a premier corner lot at the intersection of Alabama Drive and Palmer Avenue, this fully renovated 3-bedroom, 3-bathroom residence stands as a masterclass in modern luxury. Located in one of Winter Park’s most highly sought-after areas, the property is beautifully framed by the iconic tree-lined brick streets of the Chain of Lakes district and surrounded by historic estate homes. The Lifestyle: Central Florida's Premier Luxury Destination Living at 1110 Alabama Drive means immersing yourself in the rich culture and timeless elegance of Winter Park. This historic city is celebrated for its deep canopy oak trees, world-class amenities, and a laid-back atmosphere. A Walker's & Boater's Paradise: You are just a short, scenic stroll from the exclusive boutiques, acclaimed sidewalk cafes, and Michelin-starred dining lining Park Avenue. Spend your weekends grabbing fresh produce at the famous local farmers' market or launching a boat onto the stunning interconnected freshwater Chain of Lakes. Surrounded by Beauty: This home places you moments from the breathtaking, massive cypress trees and vibrant blooms of Kraft Azalea Gardens, as well as the private, historic Winter Park Racquet Club. The Residence: Fully Renovated & Refined No detail has been spared in this total home transformation, seamlessly blending a classic, highly coveted location with cutting-edge modern amenities. Gourmet Kitchen: Discover a massive chef’s footprint appointed with premium granite countertops and high-end finishes, making it the focal point for both daily living and grand entertaining. Designer Upgrades: Rich hardwood flooring flows effortlessly throughout the home, beautifully complemented by high-efficiency upgraded Pella windows that provide enhanced aesthetics and excellent energy savings. Modern Infrastructure: Enjoy total peace of mind with meticulously updated systems, including a 5-year-old tankless water heater, a custom-designed garage door, and a well-maintained 12-year-old roof. The Ultimate Outdoor Oasis Designed intentionally for the true Florida lifestyle, the exterior of this property serves as a completely private sanctuary. Signature Screened Porch: Step out into an expansive outdoor living space anchored by a cozy gas fireplace—serving as the ultimate venue for year-round entertaining. The Grounds: Relax by the private, open-air pool surrounded by lush, tropical landscaping and a fully irrigated lot, capturing resort-style living in your own backyard. Whether you are searching for a turnkey luxury residence or looking to secure a rare, premier canvas in Central Florida’s most coveted zip code, this estate has it all.

Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)

Listing Agent: Omar Albaba (813-951-7475)

Remarks: Winter Park 1964 Charmer! This wonderful ranch is located just minutes to Downtown Orlando as well as Park Ave. With over 4300 sq ft of living space, this, 4 bed/5.5 bath home is in the prime location. Upon entering you'll notice just how light and bright this home shows, to your right you will find a home office space. Rich dark wood, custom cabinetry and dramatic lighting provide the perfect space to start your morning or end your day. To the left of the entry, you will find the large formal living room with 1 of 2 gas fires places located in this home. The bay window lets you take in views of your lush landscaped front yard and fills the space with tons of sunlight. Stepping off the entry you are greeted with a large formal dining room space. Sliders lead to the patio and the unique courtyard patio gives you views of your pool from not only the dining but the primary and family room all with sliders making this the perfect patio for parties, social gatherings and events. Just off the dining room you will find the great room including the breakfast area with built in cabinetry, the family room and the kitchen. The heart of the home is your kitchen, and this space has been designed for the chef of the home. White cabinetry, island, solid surface counter tops, lighting, and a huge walk-in pantry are just a few of the special touches you will find. Stainless steel appliances: Sub-Zero refrigerator, Bosh dishwasher, double oven, and microwave all the tools needs to create amazing meals. The family room's jewelry is the barrel ceiling a special touch you won't find often. Gas fireplace, spacious, Sliders leading to the patio as well as a screened patio area. The family room also includes a wet bar with ice market and wine frig. Just off the living room is the half bath. A separate area off the living could be a mother-in-law suite, she or he cave or the options are endless. a large bonus room includes a full bath which also doubles as the pool bath, sliders leading to a private yard space and a sink area. Upstairs in this area you will also find a full bedroom with vaulted ceilings and a full bath. To the right of the dining room, you will find 2 additional rooms and 2 full baths. The primary suite includes a sitting room with double doors leading to the bedroom, massive suite with bay window and views of the pool. not 1 but 2 full baths and 2 walk in closet because why share when you can have your own. This home also includes 2 tankless heaters, newer roof, well for sprinklers, home generator, skylights, dog run circular driveway custom drapes, auto blinds, freshly painted, artificial turf and so much more. So what are you waiting for?

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

Listing Agent: Steven Looper (321-662-3582)

Remarks: Under Construction. Opportunities like this rarely present themself, just a eight-minute walk from the iconic shops, restaurants, and cafés of Park Avenue, 40 Palmer represents a rare convergence of architectural significance, uncompromising craftsmanship, and premier Winter Park location. Built by Vimaro Homes, this extraordinary new construction estate is a statement piece that redefines what luxury living looks like in the heart of Winter Park. The exterior architecture is refined yet commanding, with classical influences interpreted through a modern lens, setting the tone for the exceptional level of design and finishes found inside. One of the most remarkable features, and an offering rarely found in Winter Park, is the underground four-car garage. Designed to discreetly accommodate an impressive vehicle collection, the garage is complemented by a striking spiral staircase that rises from the basement through the main living level and continues to the second floor. The family room is nothing short of breathtaking, featuring bespoke millwork with integrated shelving, soft architectural lighting, and a dramatic fireplace wrapped entirely in marble. The kitchen is a culinary showpiece designed for those who expect nothing less than perfection. Calcutta marble countertops cascade across the space, paired with stunning custom cabinetry, and a professional-grade Thermador appliance suite. A dedicated dirty kitchen allows for discreet preparation, while an expansive walk-in pantry ensures effortless hosting and immaculate presentation. The primary bedroom wing features a spa-inspired bathroom finished in rich marble, featuring dual vanities, a freestanding soaking tub and an enormous walk-in closet with a separate washer and dryer. Upstairs, a dedicated laundry room and a spacious secondary living area provide flexibility for family living, guests, or relaxation. The lower level extends the home’s versatility, offering a workshop, dedicated holiday and seasonal storage, and seamless elevator access to the main level of the home. Outdoor living is equally impressive. A large covered exterior lanai with a pool bath and full summer kitchen creates a seamless indoor-outdoor lifestyle, ideal for entertaining year-round. The backyard is truly resort-inspired, featuring a large swimming pool, sunken fire pit, and spa, all set within a private, beautifully secluded outdoor setting. What ultimately sets 40 Palmer apart is not just its design or finishes, but its unmatched combination of luxury and location. Just minutes from Park Ave shopping and restaurants, moments from the famous Winter Park Golf Course, yet privately tucked away, this home offers a lifestyle that is both vibrant and exclusive. A truly rare opportunity to own a part of the exceptional standard of living delivered by Vimaro Homes.

Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)

Listing Agent: Julie Christensen (407-592-2055)

Remarks: Exquisite Waterfront Estate in the Heart of Winter Park - Welcome to 2211 Azalea Place, a rare and remarkable waterfront estate nestled on a quiet street in one of Winter Park’s most prestigious neighborhoods—just moments from the exclusive Winter Park Racquet Club. This extraordinary residence offers the perfect blend of timeless architecture, refined finishes, and state-of-the-art updates, all set on almost 3/4 acre of beautifully landscaped canal-front lot with direct access to the coveted Lake Maitland and Winter Park Chain of Lakes. Spanning an impressive 7,278 square feet, this two-story masterpiece rises 40 feet and is designed for both grand-scale entertaining and luxurious everyday living. Upon entry, you're greeted by soaring ceilings and elegant architectural details that set the tone for the home’s sophisticated style. With five expansive bedrooms—all featuring en-suite bathrooms—and six full baths plus a powder room, the home offers both comfort and privacy for family and guests. Two bedroom suites are located on the main level, ideal for multigenerational living or hosting overnight visitors, while the upper level includes three additional bedroom suites, a fully equipped theater room, a study room and a spacious game or playroom. The heart of the home is the gourmet kitchen, where solid wood cabinetry, rich granite countertops, and Viking appliances come together to create a true culinary haven. The adjacent family room features one of the home’s three fireplaces and invites cozy gatherings or relaxed evenings overlooking the lush outdoor living space. The formal living and dining areas are equally impressive, offering elegant backdrops for holiday celebrations or intimate dinner parties. Step outside to discover a true private oasis. The resort-style backyard boasts a saltwater heated pool and spa with all-new equipment, a summer kitchen, and a dedicated pool bathroom—perfect for effortless indoor-outdoor living. The entire property is fenced with newly installed gates, ensuring both privacy and security. From the manicured landscaping to the serene waterfront setting, every detail has been thoughtfully curated to elevate the experience of lakeside living. For boating enthusiasts, the property includes a private boathouse, a dock with an automatic lift, and a 2 jetski dock—all providing seamless access to Lake Maitland and the entire Winter Park Chain of Lakes. Whether you're setting off for an early morning paddle, an afternoon on the water, or simply enjoying the sunset from your dock, this home offers an unrivaled connection to the natural beauty. Additional features include a 5-car garage, 2 laundry rooms, dual staircases, all-new AC units, a comprehensive security system, and three wood-burning fireplaces that add charm and warmth throughout the home. Every inch of this residence has been impeccably maintained and thoughtfully updated, offering peace of mind and modern convenience without sacrificing its classic elegance. 2211 Azalea Place is more than just a home—it’s a lifestyle. This is a rare opportunity to own a one-of-a-kind estate in one of Winter Park’s most sought-after locations, where quiet sophistication meets waterfront luxury.

Listing is courtesy of: FORTUNE INTERNATIONAL REALTY (305-400-6393)

Listing Agent: Maggie Walas (407-701-0144)

Remarks: Welcome to this fully remodeled, move-in ready home in the highly sought-after Winter Park area! This beautifully updated single-story residence features 4 bedrooms and 2 bathrooms, offering comfortable living with a bright and inviting layout. Step inside to discover a bright, open floor plan with modern finishes and thoughtfully updated living spaces, designed for both comfort and functionality. The home offers spacious bedrooms, stylish upgrades, and a fresh contemporary feel throughout, making it perfect for families, first-time buyers, or anyone seeking a turnkey property. Step outside to an expansive backyard featuring a beautiful pool, creating the perfect space for relaxing, entertaining, and enjoying Florida living year-round. The large outdoor space offers endless possibilities to customize the backyard your way—whether it’s adding an outdoor kitchen, lounge area, garden, or entertainment space to create your dream outdoor oasis. Located in a quiet, established neighborhood within an A+ rated school zone, this home also offers convenient access to top shopping, dining, parks, and major highways, making commuting and daily errands a breeze. Don’t miss this incredible opportunity to own a fully remodeled home with a pool in one of the most desirable areas of Winter Park.

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

Listing Agent: Bernardo Carrasquel (407-920-4973)

Remarks: Timeless elegance meets boutique craftsmanship at 541 W Canton Ave., an exceptional new construction home by Urban Perch, proudly featured in the 2025 Parade of Homes Orlando. Near Winter Park’s iconic Park Avenue, this French Quarter-inspired residence blends historic charm and rich character with elevated modern living and a refined sense of calm. From its dormer windows and custom-carved wood entry door, to its charming striped awnings and the flicker of gas lanterns, every detail of the exterior is carefully curated. Classic marble-paved patios frame the home, and a courtyard-style pool with fountain and sandblasted marble decking invites quiet relaxation or festive gatherings. Inside, soaring ceilings, beautiful hardwood floors and immersive color-drenched rooms create an inviting space that is luxurious but unpretentious, bold yet serene. The stunning staircase features a custom wrought-iron railing with an antique finish, offering a striking architectural focal point. The chef’s kitchen, a culinary sanctuary and social hub, is complete with graphite La Cornue range and pot filler, Monogram paneled refrigerator, custom plaster hood, quartzite countertops and backsplash, and grand center island that opens to a gathering room with a gas fireplace. This more relaxed living area flows effortlessly through French doors to the pool and patios, creating an ideal indoor-outdoor lifestyle. A butler’s pantry with a second refrigerator, cabinetry and prep space adds functionality, while the formal dining room, living room, and bar area with sink and built-in beverage cooler are ideal for entertaining. A beautiful downstairs powder bath features designer wallpaper, elegant sconces and custom cabinetry. The upstairs primary suite offers spa-like serenity, including a wet room complete with soaking tub framed by a picture window. Three additional bedrooms include one with an en-suite bath, while the other two share a hallway-accessible bath with double vanity and walk-in tiled shower. This masterpiece set in the heart of Winter Park, thoughtfully surrounded by lush landscaping and carefully placed privacy screens, offers polish and presence in an ideal location.

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

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

Remarks: Under contract-accepting backup offers. Location, Location, Location! Charming first floor 1 bedroom, 1 bath condo ideally located on North Park Avenue in the retro-chic Park Aire complex. Beautifully overhauled in 2018 with quartz counters, new cabinetry, new appliances, custom mosaic kitchen detail, new flooring, new lighting, updated electrical, with picturesque views of the Winter Park Golf Course and Casa Feliz. Enjoy a large walk-in closet, one assigned carport space, and a private storage room. The community offers a sparkling saltwater pool, two third-floor outdoor patios, laundry facility, elevator, and a guest-quarters efficiency available to owners for a nominal fee. Just steps from Park Avenue shopping and dining, cafes, churches, Winter Park Golf Club, Rollins College and more. No pets.

Listing is courtesy of: PARK TOWN REAL ESTATE LLC (561-801-9199)

Listing Agent: David Auerbach (407-619-5250)

Remarks: Under contract-accepting backup offers. Location, location, location. Sought after location on the North end of Park Avenue. Avoid the traffic in and out of Downtown Winter Park while being minutes away from everything on the Avenue. One of the very few single level homes of this quality in Winter Park 32789. Single story ranch on a lovely, private, large corner lot. 2306 heated and cooled square feet. Primary bedroom en-suite with 3 additional bedrooms and 2 additional bathrooms, 15,000 sq ft large corner lot with oversized side-entry garage and over-sized laundry room. Magnificent, private back yard oasis with pool and covered veranda. Freshly painted inside and outside. New lovely oak wood floors, newer roof and windows, new hardware and updated lighting. Oversized two car garage with storage. This home is move-in ready and all the model-home furniture is available to purchase as well.

Listing is courtesy of: PHIL KEAN REAL ESTATE LLC (407-982-2265)

Listing Agent: Brad Grosberg (321-439-1494)

Remarks: Pre-Construction. To be built. This home is under construction proposed completion March 2027. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneath mature oak canopies being built by FG Schaub Custom Homes. A short walk to Phelps Park, YMCA, dinner and shopping.  Surrounded by natural beauty and designed with intention, The Enclave offers a rare opportunity to enjoy a private, residential setting while remaining connected to the area’s finest dining, shopping, and cultural amenities just minutes away in downtown Winter Park.. With a limited collection of custom homes, this community delivers an elevated lifestyle defined by architecture, walkability, and enduring charm. This custom single-family home is thoughtfully designed with exceptional craftsmanship and upscale finishes throughout. Each residence features high-performance, low-E double-pane windows, 8-foot solid core interior doors, and tankless gas water heaters for modern efficiency and comfort. Homes are appointed with premium Wolf and Sub-Zero appliances, designer-selected finishes, and a curated palette of colors and materials. These homes have it all; summer kitchens well equipped with fridge and grill and a sparkling pool.  Spacious layouts, refined detailing, and quality construction create an elevated yet livable environment, all set within a beautifully landscaped and private setting. Please inquire for details and customization options.

Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)

Listing Agent: Laura Earl (443-994-9441)

Remarks: Timeless Elegance Meets Modern Luxury in Winter Park's Most Coveted Location Discover an extraordinary residence where exceptional craftsmanship and sophisticated design converge at 948 Poinciana Lane. This meticulously reimagined estate represents the pinnacle of refined living in one of Winter Park's most prestigious neighborhoods, offering an effortless blend of classic architecture and contemporary luxury. From the moment you step through the elegant foyer, you're greeted by sun-drenched interiors showcasing gleaming hardwood floors, soaring coffered ceilings, and designer details at every turn. The thoughtful floor plan reveals a private home office with custom built-ins and fireplace to the right, and a gracious formal dining room to the left—perfect for hosting memorable gatherings. The heart of this home is the spectacular kitchen, a true chef's masterpiece featuring custom cabinetry, pristine marble countertops, statement pendant lighting, and top-tier appliances. This culinary haven flows seamlessly into the light-filled family room, where expansive windows frame views of your private outdoor sanctuary. The first-floor primary retreat is a haven of tranquility, featuring an expansive walk-in dressing room with exceptional storage and a spa-inspired ensuite bath. Luxuriate in the freestanding soaking tub, refresh in the walk-in shower, or prepare for your day at the generous double vanity—all appointed with elegant finishes befitting this caliber of home. Three generously proportioned guest bedrooms upstairs offer optimal comfort and privacy, complemented by a Jack-and-Jill bath and additional hall bath. A spacious bonus room with backyard views provides versatility for a media room, playroom, or home gym. Above the garage, an additional 260-square-foot bonus room with wet bar and wine fridge creates the ideal entertainer's lounge or game room. Step through French doors to your private resort-style backyard—a meticulously landscaped oasis featuring a sparkling pool and spa surrounded by lush greenery, stately palms, and thoughtful lighting. Whether gathering around the firepit, lounging poolside, or dining alfresco under the stars, this outdoor retreat elevates everyday living to an art form. No detail has been overlooked in this complete renovation: designer light fixtures and custom window treatments throughout, first-floor laundry convenience, elevated trim and baseboard, fresh paint, recessed lighting, and three HVAC units ensuring year-round comfort. The location is simply unparalleled—a leisurely stroll to the Winter Park Racquet Club, zoned for A-rated public schools, and just moments from the world-renowned shops and restaurants of Park Avenue. This is more than a home; it's a lifestyle of distinction in Central Florida's most desirable address.

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

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

Remarks: Modern Luxury in the Heart of Winter Park! Welcome to this stunning modern residence, thoughtfully constructed in 2023 by the original owner/builder, located in one of Winter Park’s most sought-after neighborhoods. Designed with sleek sophistication and functional elegance, this fabulous home offers 4 bedrooms, 3 full baths, and a flexible layout perfect for today’s lifestyle. The open-concept main floor features a beautifully appointed kitchen, a spacious dining area, and a light-filled living room complete with a designer fireplace and custom built-in shelving. The stunning kitchen boasts quartz counters, spacious cabinetry, KitchenAid appliances, and designer lighting. A fourth bedroom (currently used as a study) is also located on the main level. From the great room, expansive sliding glass doors lead out to the covered lanai, where you'll find an in-ground pool, a fully fenced yard, tongue-in-groove wood ceiling, and pre-plumbing in place for your dream summer kitchen—ideal for entertaining year-round. Upstairs, the luxurious primary suite provides a peaceful retreat with an oversized balcony overlooking the pool and rear yard. Two additional bedrooms are also featured on the second level, along with a second full bath. The first-floor office doubles as a fourth bedroom, with an adjacent full bath for guests or multi-generational living. The side entry two-car garage was once converted into a 425 sq ft air-conditioned bonus room—perfect as a media room, home gym, or additional living space. This could easily be converted back if the next owner requires more living space. This home boasts well-thought-out upgrades, including beautiful wood inlays in niches, open shelving, quartz countertops, slat wall features, and stunning light fixtures throughout. The work has been done for you in this like-new home! Located just steps from Phelps Park, and minutes from the shops and dining of Park Avenue and the Winter Park Chain of Lakes, this home offers the perfect blend of modern design, comfort, and convenience. Don't miss your chance to own this exceptional home in the heart of Winter Park!

Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)

Listing Agent: Sue Silberbusch (407-252-3157)

Remarks: Pre-Construction. To be built. Welcome to The Enclave at Winter Park—an exclusive collection of architecturally distinctive residences crafted by FG Schaub Custom Homes, blending timeless character with modern luxury. 901 Enclave Place (Lot1) is a thoughtfully designed courtyard home offering an elegant yet functional layout centered around private outdoor living. A charming covered front porch and welcoming foyer lead into an expansive open-concept gathering and dining space, seamlessly connected to a designer kitchen featuring a large center island, walk-in pantry, and effortless flow for entertaining. At the heart of the home, a covered lanai and courtyard create a true indoor-outdoor lifestyle—perfect for year-round enjoyment and intimate gatherings. The first-floor primary suite is a private retreat with a spacious walk-in closet and spa-inspired bath, complemented by a convenient powder bath and laundry/pantry area. Upstairs, you’ll find a well-appointed layout including an second primary suite with a luxurious bath and oversized closet, a additional bedroom, full bath, and a versatile gathering loft—ideal as a media room, office, or flex space. Designed with both comfort and sophistication in mind, this residence showcases clean architectural lines, abundant natural light, and carefully curated indoor and outdoor living spaces. Located within a boutique enclave of just a limited number of homes, residents will enjoy a serene setting surrounded by mature trees and thoughtfully designed community green space. Experience the best of Winter Park living with close proximity to renowned dining, shopping, and top-rated schools—all within one of the area’s most sought-after new communities. Design book is available upon request. Please inquire for details and customization options.

Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)

Listing Agent: Laura Earl (443-994-9441)

Remarks: Pre-Construction. To be built. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneath mature oak canopies, being built by FG Schaub Custom Homes. Ideally located within walking distance to Park Avenue and historic Old Winter Park, this exclusive neighborhood blends timeless character with modern luxury. The courtyard homes at The Enclave offer a distinctive design centered around light, openness, and indoor-outdoor living. These four-bedroom residences feature thoughtfully designed floor plans with a first-floor primary suite and expansive living spaces that flow seamlessly to private outdoor areas. Large windows and two unique entry design options allow for abundant natural light, enhancing the open-concept layouts. Each home is finished with high-end selections, including Wolf and Sub-Zero appliances, high-performance double-pane windows, and elevated interior finishes throughout. Blending modern design with comfort and functionality, these homes provide a unique opportunity to enjoy a private courtyard lifestyle in one of Winter Park’s most desirable locations. Design book is available upon request. Please inquire for details and customization options.

Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)

Listing Agent: Matthew Burks (407-257-5347)

Remarks: Exquisite new construction in the Heart of Winter Park perfectly positioned on an oversized lot just steps from Park Avenue’s renowned shops, fine dining, and the iconic Winter Park 9-hole golf course, this extraordinary custom residence is a showcase of timeless design and modern luxury. Conceived by acclaimed architect Dan Delong of Origins Residential Design and brought to life by Sean Wulff of Native Homes, every detail has been thoughtfully curated to impress even the most discerning buyer. The expansive floor plan encompasses 5 bedrooms, 6 full baths, and 1 half bath, blending sophistication and comfort across multiple living spaces. Highlights include a dramatic great room, inviting family room, private study, downstairs guest suite, a full bar featuring a 56-bottle wine refrigerator, and an upstairs game room ideal for both everyday living and elegant entertaining. A grand entry reveals the great room with soaring floor-to-ceiling windows and elegant Italian porcelain tile, all overlooking the serene pool and patio. The chef’s kitchen seamlessly connects to the family room and features Canadian-crafted European-style cabinetry, Wolf, Sub-Zero & Fisher & Paykel appliances (dual ovens, dual dishwashers, built-in coffee maker, wine cooler, and beverage center), quartzite countertops, a large island with bar seating, hidden walk-in pantry, plus whole house water softener and filtration systems for premium convenience. The first-floor primary suite is a true retreat with spa-inspired amenities and a custom-built walk-in closet complete with cabinetry and a spacious island. Also on the main level: a private guest suite and dedicated home office/study. Upstairs, a generous game room and three additional en suite bedrooms provide comfort and privacy for family and guests alike. Designed for seamless indoor-outdoor living, the residence boasts two covered lanais finished in Turkish Marble, disappearing screens, a summer kitchen with Urban Bonfire Cabinetry, refrigerator, and ice maker, along with a freestanding fire pit and lush tropical landscaping. The saltwater pool with sun shelf and heated gas spa ensures year-round enjoyment. Built to the highest standards, the home features R-14 block walls with core 500 insulation, open cell foam insulation in attic, Andersen windows, a flat concrete tile roof, and tongue-and-groove ceilings on all lanais. Additional luxuries include: Select European white oak wood floors and Italian porcelain flooring throughout 12’ ceilings on the main level, 10’ ceilings upstairs Cutting-edge construction for efficiency and durability

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

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

Remarks: Pre-Construction. To be built. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneath mature oak canopies, being built by FG Schaub Custom Homes. A short walk to Phelps Park, YMCA, dinner and shopping.  Surrounded by natural beauty and designed with intention, The Enclave offers a rare opportunity to enjoy a private, residential setting while remaining connected to the area’s finest dining, shopping, and cultural amenities just minutes away in downtown Winter Park.. With a limited collection of custom homes, this community delivers an elevated lifestyle defined by architecture, walkability, and enduring charm. This custom single-family home is thoughtfully designed with exceptional craftsmanship and upscale finishes throughout. Each residence features high-performance, low-E double-pane windows, 8-foot solid core interior doors, and tankless gas water heaters for modern efficiency and comfort. Homes are appointed with premium Wolf and Sub-Zero appliances, designer-selected finishes, and a curated palette of colors and materials. These homes have it all; summer kitchens well equipped with fridge and grill and a sparkling pool.  Spacious layouts, refined detailing, and quality construction create a elevated yet livable environment, all set within a beautifully landscaped and private setting. Please inquire for details and customization options.

Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)

Listing Agent: Matthew Burks (407-257-5347)

Remarks: Nestled behind gates in the heart of Winter park, this enchanting 1930's residence blends historic charm with many recent upgrades. The beautifully renovated kitchen anchors the home, while the downstairs primary suite offers privacy and comfort with an elegant spa inspired bath. The detached one bedroom guest house is perfect for houseguests, a home office or multi-generational living. The main house has a flexible floor plan that includes four bedrooms and four and one half baths, a sunroom ideal for home office, formal dining room, oversized family room and charming sitting area with fireplace. The kitchen is a chef's delight with six burner gas range, large center island, plentiful l space for gatherings and a separate breakfast room. Other notable features include gleaming wood floors, double pane windows offering abundant natural light, adorable laundry room/mud room. French doors from many rooms open to a classic front porch that is a perfect place for relaxing and enjoying picturesque grounds with towering oaks. Step outside to a private heated pool. Detached garage includes Tesla charging station. This gated compound situated on .42 acres is one block from Lake Osceola and a easy walk to Park Avenue.

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

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

Remarks: Move right into this beautifully two-bedroom, two-bath condominium located in desirable East Winter Park. The thoughtfully designed floor plan offers two spacious bedrooms, and bathrooms—one featuring a tub and the other a shower—providing comfort and privacy. The light-filled great room showcases attractive laminate wood flooring and sliding glass doors that open to a private, screened-in porch overlooking a sunny, landscaped courtyard—perfect for relaxing. Recent upgrades include a new AC system (May 2021), a new roof (2022), exterior paint 2025, updated bathrooms, upgraded laminate wood flooring throughout. The primary bathroom has been enhanced with a luxurious walk-in shower featuring upgraded stone and tile finishes. This unit is quietly situated in a private location within the well-maintained Wrenwood Condominiums community, offering assigned parking directly in front of the unit and access to a sparkling community swimming pool. Ideally located in East Winter Park, this community offers easy access to Park Avenue shopping and dining, Winter Park Village, Full Sail University, and nearby parks and lakes. Enjoy a vibrant lifestyle with museums, farmers markets, scenic walking areas, and the renowned Winter Park Chain of Lakes just minutes away, all while remaining close to major roadways and downtown Orlando. Schedule your private showing today.

Listing is courtesy of: SUNSHINE BROKERAGE, LLC (407-509-7961)

Listing Agent: Sonny Manku (407-509-7961)

Remarks: Timeless Olde Winter Park charm meets relaxed Florida living at 823 Granville Drive, a true Park Grove gem on an expansive 100' x 135' lot. Nestled among tree-lined streets in this coveted, well-established neighborhood, this single-story residence offers 4 bedrooms, 3.5 baths, and effortless indoor-outdoor living. Thoughtfully designed for entertaining, the home features two fireplaces that anchor inviting living and family spaces, creating a warm, elegant backdrop for gatherings large and small. The open, flowing layout keeps daily living convenient on one level while offering plenty of separation for guests or multi-generational living. Step outside to your own private retreat: a screened, enclosed pool area that feels like an outdoor living room, perfect for morning laps, weekend barbecues, or evening cocktails. The generous lot provides room to play, garden, or simply enjoy the lush surroundings and privacy Park Grove is known for. Practical features include a two-car garage, ample storage, and the rare opportunity to own a pool home in one of Winter Park’s most sought-after neighborhoods, just minutes to Park Avenue shopping, dining, lakes, and cultural venues. This is the Park Grove lifestyle—single-story, pool, charm, and location—all in one compelling property.

Listing is courtesy of: FLORIDA ONE REAL ESTATE LLC (407-599-7070)

Listing Agent: Anthony Consalvo (407-599-7070)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to one of the most affordable opportunities to own in the highly sought-after Winter Park High School district. This well-maintained community is tucked into a beautiful setting and is extremely convenient to everything that makes Winter Park one of Central Florida's top lifestyle destinations. This end-unit two bedroom / two-and-a-half bath condo in Sandlewood Creek combines a hip retro-classic style with comfort, functionality, and peace of mind with a long list of recent improvements. Solid knotty-pine wood accent paneling is featured throughout and compliments the freshly painted walls in designer colors. The kitchen has been partially renovated and has a nice clean and modern vibe, complemented by granite countertops and updated bathrooms for a clean, modern feel. The roof was replaced in 2021. Major system upgrades include an A/C (2019) and a brand-new water heater (2026), while the entire interior has just been freshly painted, carpets professionally cleaned, and a final detailed cleaning completed—making this home truly move-in ready. Whether you're looking for a primary residence, a low-maintenance lifestyle, or a smart investment in one of Central Florida’s most consistently in-demand areas, this property checks all the boxes. Enjoy easy living in a quiet, established community just minutes from everything that makes Winter Park special—top-rated schools, dining, shopping, and parks. Pre-approved for FHA financing and recent updates that your insurance company will like - this is a rare opportunity in this market. Don't miss it!. Sellers have this priced to sell, so don't delay. Call today to make your appointment for your private viewing.

Listing is courtesy of: DERENTHAL REALTY (321-662-8014)

Listing Agent: Mike Derenthal (321-662-8014)

Remarks: 3 bedroom 3 bathroom pool home. Enjoy the large backyard. Schedule your showing today!

Listing is courtesy of: ALFA REAL ESTATE LLC (407-545-9562)

Listing Agent: Thai Nguyen (407-545-9562)