Winter Park Single Family Homes For Sale - 308 homes

Remarks: Ideally on a quiet residential street just near Park Avenue, this custom-built transitional residence offers the best of Winter Park living, accessible, refined and thoughtfully designed from the ground up. Built in 2018 by Carlos Posada, the home delivers 2,653 square feet of living space across two floors, with an additional 365 square feet walk-up attic, four bedrooms and four full baths. From the moment you enter, the home makes an impression. French clay tile flooring anchors the defined foyer, opening into an expansive great room where Bolivian rosewood built-ins frame a gas fireplace and oversized windows draw the eye toward the pool and lanai beyond. The living, dining and kitchen spaces connect seamlessly, designed for everyday ease and effortless entertaining. The kitchen is equipped for the serious home cook, anchored by a full Thermador appliance package and thoughtfully appointed beyond the expected. The large island integrates a sink, microwave drawer, ice maker and refrigeration drawers alongside generous seating, while a walk-in pantry, concealed outlets and a warming drawer round out a workspace as purposeful as it is refined. Outdoor living is equally deliberate. A covered lanai with fireplace and space for a mounted television flows to an open-air terrace and dedicated grilling area, all overlooking a linear pool with water feature and professionally designed landscaping with evening lighting. Upstairs, the primary suite is positioned at rear of the home for added privacy, with abundant natural light, a generous walk-in closet and an en-suite bath. Two additional bedrooms each offer their en-suite baths and built-in closets. A well-appointed laundry room, along with a linen closet and dedicated storage closet in the hall, complete the second floor. On the main level, a fourth bedroom is finished as a library with custom white oak built-ins and French doors opening to the exterior of the home, offering flexible living or professional workspace. Throughout, Panaget engineered hardwood flooring, decorative crown molding, Sierra Pacific windows and doors, cast stone accents, and integrated stair lighting reflect the home's elevated attention to detail. Additional highlights include a detached two-car garage, extensive storage throughout and an infrastructure designed for future elevator conversion. A rare opportunity to own a newer custom home in one of Winter Park's accessible and beloved neighborhoods.

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

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

Remarks: Welcome to an exceptional opportunity in the highly desirable Park Grove community, an impeccably updated one-story residence ideally situated just moments from the vibrant shops and dining of Park Avenue and all that downtown Winter Park has to offer. With charming curb appeal, pristine landscaping and timeless architectural appeal, this home makes a stunning first impression. Inside, a thoughtfully designed floor plan offers seamless flow, perfectly suited for both everyday living and effortless entertaining. Beautiful wood flooring spans the main living areas, while the Florida room showcases distinctive Mexican tile, adding warmth and character. Designer lighting, curated tile selections and stylish wallpaper accents create a bright, inviting aesthetic throughout. The formal sitting room, complete with custom built-ins and an elegant dining room provide refined gathering spaces. At the heart of the home, a light-filled kitchen opens to the spacious family room, where a cozy wood-burning fireplace serves as a focal point. The adjacent Florida room is lined with windows, offering serene views of the sparkling pool and lush, private backyard. The generously sized primary suite is thoughtfully positioned for privacy, featuring its own wood-burning fireplace, a large walk-in closet and a beautifully appointed ensuite bath with dual vanities and an oversized walk-in shower. Four additional bedrooms are located on the opposite side of the home, two of which include ensuite baths, ideal for guests or multi-generational living. Outdoor living is equally impressive, with a beautifully paved lanai overlooking the pool and ample space for alfresco dining, entertaining and relaxing poolside. Tucked away in one of Winter Park’s sought-after neighborhoods, this home offers tranquility and convenience, with easy access to downtown Orlando, major hospitals, top-rated public and private schools and key roadways. A rare blend of style, comfort and location; this is Florida living at its finest.

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

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

Remarks: Under contract-accepting backup offers. TRANSFERABLE TERMITE BOND INCLUDED. Welcome home to the charm and character of the bygone days. This 3-bedroom, 2-bathroom home offers 2,556 square feet, with the historic main home originally built in 1922. Featuring original antique wood floors, a classic fireplace, and a one of a kind upstairs loft, there's nothing quite like it! A charming front porch welcomes you into the living room with a fireplace. A front room currently used as a formal parlor or sitting room doubles as the third bedroom, also ideal for entertaining or reading. Two additional bedrooms and full baths are located down the hall. The dining room sits just off the main living space, with French doors opening into the hallway. The kitchen is positioned toward the back of the home with a tucked away laundry closet. Accessed by an interior staircase off the kitchen, the HIGHLIGHT of the home is the handcrafted upstairs loft with design in a class of itself. Currently used as an exquisite billiards room and library, this flexible space can serve as a library, office, or creative retreat, and features a balcony with views of Lake Killarney. Additional features include 42-inch kitchen cabinets, stone countertops, a roof replaced in 2018, AC replaced in 2019. Wind mitigation passed April 2024, septic pumped October 2025, and on top of it all, no HOA! Conveniently located minutes from Downtown Winter Park, Park Avenue, Rollins College, and just minutes from I-4, this is a truly unique property offering craftsmanship and character rarely found today.

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

Listing Agent: Veronica Figueroa (407-519-3980)

Remarks: Under contract-accepting backup offers. Walk in and feel instantly at home in this stunning 5-bedroom, 3-bath POOL home with a 3-car garage, offering over 3,600 square feet of living space on more than ¾ of an acre in the highly desirable Sevilla neighborhood of Winter Park. Backing directly to Howell Creek and Mead Gardens, this property offers the rare luxury of no rear neighbors and exceptional privacy. Upon entry, you’re welcomed by beautiful wood floors and versatile spaces to the left that can serve as a formal living room, dining room, office, or playroom. Continue into the impressive family room, featuring vaulted ceilings, skylights, and a wood-burning fireplace, creating a light-filled and inviting atmosphere. To the right wing of the home are four bedrooms and two bathrooms, including the primary suite. One secondary bedroom connects to the primary, making it ideal for a nursery, home office, or sitting room. The spacious primary retreat offers large walk-in closets, dual vanities, a soaking tub, separate shower, and French doors that open directly to the pool and backyard oasis. The kitchen, located just off the family room, features travertine flooring and flows seamlessly into a huge pantry, oversized laundry room, drop zone, and a second primary suite with ensuite bath—perfect for guests or multigenerational living. Outside, the home has been meticulously maintained, showcasing a new roof (2023), exterior paint (2018), pavered circular driveway, well, and lush tropical landscaping that enhances the home’s curb appeal. Additional features include a three-car side-entry garage, pool heater, designer lighting, engineered hardwood floors, and crown molding throughout. Located within the highly sought-after Winter Park School District (Audubon K-8 and Winter Park High School) and just minutes from Park Avenue, Central Park, Rollins College, SunRail, the Winter Park Farmer’s Market, and world-class shopping and dining. Schedule your private showing today—this exceptional home won’t last long!

Listing is courtesy of: VOSS REALTY INC (407-456-0777)

Listing Agent: Lindsay Kaye Voss (407-456-0777)

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: SELLER MOTIVATED!! Potential of an extra one percent for closing costs, just ask your agent!! A FULLY MODERNIZED 5-bedroom, 3-bathroom home offering Modern style, flexibility, and comfort and its own ATTACHED 2bed/1 Bath IN-LAW SUITE!!! Step inside to an open and airy layout featuring Luxury vinyl plank flooring, fresh neutral paint, and large windows that fill the home with natural light. The upgraded kitchen is a true showstopper — boasting shaker cabinets, quartz countertops, subway tile backsplash, and stainless steel appliances with stylish hardware accents. Located just a 10 minute walk to Lake Killarney and a 3 minute walk to Killarney Elementary School! What is even more fantastic is the distance to I-4 is literally just 2 minutes away for fast and convenient travel to and from downtown Orlando and just 10 minutes from Park Avenue Winter Park!! So many restaurants, parks, local shops and family activities, Especially during the holidays!! Come see this home with potential income and your own private 3/2 as well. This home includes a versatile 2-bedroom, 1-bath in-law suite with its own private entrance, perfect for extended family, guests, or rental potential. Enjoy extra living space in the spacious Florida room, ideal for entertaining, relaxing, or creating the perfect indoor-outdoor flow. With its thoughtful upgrades and multi-generational layout, this home blends functionality with timeless design — truly move-in ready and waiting for you to make it your own!

Listing is courtesy of: EXP REALTY LLC (407-846-0940)

Listing Agent: Laura Mcadams (954-268-5421)

Remarks: SELLER MOTIVATED!! Potential of an extra one percent for closing costs, just ask your agent!! Come view this NEXTGEN Home FULLY MODERNIZED 5-bedroom, 3-bathroom home offering flexibility, and comfort that Includes an Attached 2 Bed/1 Bath IN- LAW SUITE!! Step inside to an open and airy layout featuring Luxury plank flooring, fresh neutral paint, and large windows that fill the home with natural light. The upgraded kitchen is a true showstopper — boasting shaker cabinets, quartz countertops, subway tile backsplash, and stainless steel appliances with stylish hardware accents. Located just a 10 minute walk to Lake Killarney and a 3 minute walk to Killarney Elementary School! What is even more fantastic is the distance to I-4 is literally just 2 minutes away for fast and convenient travel to and from downtown Orlando and just 10 minutes from Park Avenue Winter Park!! So many restaurants, parks, local shops and family activities, Especially during the holidays!! Come see this home with potential income and your own private 3/2 as well. This home includes a versatile 2-bedroom, 1-bath in-law suite with its own private entrance, perfect for extended family, guests, or rental potential. Enjoy extra living space in the spacious Florida room, ideal for entertaining, relaxing, or creating the perfect indoor-outdoor flow. With its thoughtful upgrades and multi-generational layout, this home blends functionality with timeless design — truly move-in ready and waiting for you to make it your own!

Listing is courtesy of: EXP REALTY LLC (407-846-0940)

Listing Agent: Laura Mcadams (954-268-5421)

Remarks: Under contract-accepting backup offers. Rare opportunity in the heart of Winter Park! This property sits on a double lot (0.29 acres) — a true rarity in this highly desirable location. The existing 1953 concrete-block home (3 bed / 2 bath) with an attached garage apartment (studio + bath) and shared 2-car carport offers little to no current value and would require a complete renovation. Property will be sold as-is with no repairs. Furniture removal prior to closing is negotiable. The real value is in the land. With privacy at the end of a quiet street, and a doctor’s office next door, the property is ideally located steps from AdventHealth Winter Park Hospital, Lakemont Center, and just 5 minutes from Rollins College and Park Avenue’s shopping and dining. The property features a large tree-lined backyard, city water and sewer, cable, and electricity already available. Whether you choose to restore a solid 1950s block home or tear down and build your dream estate while saving on impact fees, this is a prime investment opportunity in one of Central Florida’s most sought-after areas.

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

Listing Agent: Cliff Glansen

Remarks: Under contract-accepting backup offers. Welcome to Timberlane Shores—one of Winter Park’s most desirable neighborhoods! This beautiful 4-bedroom, 4.5-bath home sits on over a third of an acre in a quiet, tucked-away location with gorgeous updated landscaping. Inside, you’ll find wide-plank hardwood floors throughout and a thoughtfully designed floor plan with separate living and dining rooms plus a spacious family room. The bright kitchen features white cabinetry with pull-out drawers, marble countertops, subway tile backsplash, and newer appliances (2018), including a Sub-Zero refrigerator and Wolf gas 4 burner range. The kitchen opens to a bright sunroom with beautiful wood-like tile floors laid in a herringbone pattern (2018). Such a great space that is filled with natural light—perfect as a casual gathering space or playroom, making this an ideal home for entertaining. The sunroom overlooks the enormous backyard space and large pool area with custom designed pavers (2023). A downstairs guest suite with full bath provides comfort and privacy, while a dedicated office with built-in desks and brand new carpet adds functionality. Upstairs, the oversized primary suite boasts a beautifully appointed bathroom with dual sinks, marble countertops, soaking tub, and separate walk-in shower, along with a custom walk-in closet. Two additional upstairs bedrooms each offer en-suite baths, including one renovated in 2021. Recent updates include new windows (2017), solid wood front door (2021), renovated bath (2021), two new AC units and duct cleaning (2024), and a new roof (2024). This exceptional home offers the perfect blend of style, comfort, and location—truly a must-see.

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

Listing Agent: Lisa Fleming (321-228-8341)

Remarks: Welcome to refined Florida living in the highly sought-after gated community of Lakeside Estates, one of Winter Park’s most exclusive neighborhoods, where homes rarely come to market. With only 39 residences, this intimate lakefront community offers a level of privacy, prestige, and curb appeal that is increasingly difficult to find. From the moment you pass through the impressive gated entrance framed by a beautifully designed pond, elegant stone wall, and striking fountain, you immediately sense that Lakeside Estates is something special. This Mediterranean-inspired residence showcases timeless architectural design with a stunning stone-accented tower entry, graceful arched architecture, and a classic barrel tile roof, all complemented by a beautifully maintained paver driveway and a welcoming 8-foot front door. Inside, thoughtful craftsmanship is evident throughout, with colonial-style crown molding, designer finishes, and wood-look porcelain plank tile flooring that delivers the warmth of hardwood with exceptional durability. At the heart of the home, the chef’s kitchen is designed for both everyday living and entertaining, featuring white shaker cabinetry with crown molding, quartz countertops with elegant marble-inspired veining, stainless steel appliances, and a double oven. A beautifully appointed butler’s pantry with a built-in wine rack enhances both convenience and sophistication. The versatile floor plan includes a dedicated office, four bedrooms, spacious living areas, and generously sized rooms, creating flexibility for modern lifestyles. The primary suite provides a private retreat with spa-inspired features and ample storage. Step outside to your own backyard oasis featuring an enclosed saltwater pool, peaceful water views, and pre-plumbing for a future outdoor kitchen, making this outdoor space ideal for year-round entertaining. A convenient full pool bath provides easy access for guests while enjoying the outdoor living areas. Additional highlights include wall-mounted garage storage, kayak storage, and thoughtful design details throughout. Residents of Lakeside Estates enjoy access to a community dock where fishing and kayaking are possible, along with a playground and beautifully maintained common areas, all supported by an HOA that maintains the entrance and shared spaces. Ideally located in Winter Park and zoned for highly regarded schools, this home offers a rare opportunity to own within a private gated community where availability is limited, and demand remains strong.

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

Listing Agent: Brian Diaz (386-837-2386)

Remarks: Under contract-accepting backup offers. Welcome to a rare gem in one of Winter Park’s most sought-after neighborhoods, Brookshire Heights—where trees line the street and the mailman still delivers right to your front door. Perfectly positioned with the scenic and wooded Cady Way Trail in your backyard, this custom-built 2022 residence offers over 2,100 square feet of thoughtfully designed single-story living, where refined style meets everyday ease. A desirable open-concept floor plan showcases three bedrooms and two bathrooms, enhanced by wood-look plank tile flooring, soaring ceilings and doorways, crown molding, and recessed lighting throughout. Expansive sliding glass doors with electric retractable blinds and transom windows flood the home with natural light, creating a seamless connection to the covered, screened lanai—perfect for effortless indoor-outdoor living and sophisticated entertaining. The beautifully appointed kitchen is both striking and functional, featuring crisp white shaker cabinetry complemented by a contrasting gray island with seating for four, all topped with sleek white quartz countertops. A dedicated wine and beverage bar with a built-in refrigerator adds an elevated touch, while stainless steel appliances and a spacious pantry ensure everyday convenience. Bathed in natural light, the dining area offers an inviting and elegant setting for both intimate gatherings and larger-scale entertaining, with expansive windows that bring the outdoors in. The primary suite serves as a serene retreat, complete with private lanai access for a tranquil indoor-outdoor connection. A generously sized custom closet provides ample storage, while the spa-inspired bathroom features a timeless clawfoot soaking tub, honeycomb tile flooring, an expansive walk-in shower, and a dual quartz vanity—creating a luxurious, resort-style experience. Two additional bedrooms offer flexibility for guests, family, or workspace, including one with stylish built-in shelving. A beautifully finished hall bath reflects the same elevated design and attention to detail found throughout the home. Designed with functionality in mind, the well-appointed laundry room features built-in cabinetry and a hanging bar, provides convenient access to both the primary suite and main living areas. A spacious 2.5 car garage allows plenty of room for storage, a golf cart or other toys. Ideally located, this residence offers convenient access to premier institutions including University of Central Florida, Rollins College, and Full Sail University. Enjoy nearby recreation at Winter Park Pines Golf Club and Cady Way Park, featuring a pool, playground, tennis and pickleball courts, and beach volleyball. Spend weekends boating from Dinky Dock Park onto the renowned Winter Park Chain of Lakes, or explore the charm of Park Avenue with its boutique shopping and fine dining. Everyday convenience is enhanced with close proximity to AdventHealth Winter Park and the Crosby Wellness Center, along with easy access to Orlando International Airport. Zoned for top-rated schools including Brookshire Elementary School, Glenridge Middle School, and Winter Park High School, this exceptional property seamlessly blends lifestyle, location, and lasting value. Roof - 2022, HVAC - 2022, Electrical - 2022, Plumbing - 2022, Water Heater - 2022

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

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

Remarks: Charming 3-bedroom, 2-bath home in the heart of desirable Winter Park. Bright and inviting layout with comfortable living spaces and plenty of natural light. Enjoy a private backyard perfect for relaxing or enteraining. Conveniently located near shopping and dinning.

Listing is courtesy of: INT'L PROFESSIONAL REALTY INC (407-699-7718)

Listing Agent: Lorena Ortega (407-256-3631)

Remarks: Seller may consider buyer concessions if made in an offer ~ Beautiful upgrades, a versatile layout, and the best of Winter Park at your doorstep! With Dubsdread Golf Course just around the corner and Fairbanks Avenue minutes away, this 4-bedroom, 3.5-bath CUSTOM BUILT HOME puts you in the center of it all – NO HOA required! Major systems have been well maintained; including a NEW A/C UNIT with UV lights (2025), FRESH INTERIOR PAINT, NEWER WATER HEATER (2021), double-pane windows, and the aerobic septic system was recently serviced (2022). All that is left is to move in and enjoy the lifestyle! This home’s flexible floor plan delivers TWO PRIMARY SUITES – one on the first floor and another upstairs – making it ideal for multi-generational living, in-laws, long-term guests, or simply room to grow. The downstairs suite features a spa-like en-suite bath with dual sinks, a SOAKING TUB, large glass shower, and a WALK-IN/THROUGH CLOSET that connects directly to the main floor laundry. Upstairs, the second suite offers a private bath and direct access to a balcony. The SECOND LAUNDRY ROOM upstairs and huge 30x11 BONUS/UTILITY ROOM provide even more convenience and space. At the heart of the home you will find a GOURMET KITCHEN, crafted with the home chef in mind offering an LG STUDIO REFRIGERATOR, INDUCTION COOKTOP, DOUBLE WALL OVEN, sleek stone counters and a complementary backsplash, upgraded cabinetry, and a large ISLAND with bar seating and chic pendant lighting. The kitchen flows seamlessly into the OPEN LIVING AND DINING AREAS, making everyday living or hosting family and friends a breeze. The LOFT at the top of the stairs delivers additional flexible living space and includes a wet bar with fridge, perfect for a casual hangout space, movie room, office space or anything else you or your family might need. TILE AND WOOD FLOORS, crown molding, and an abundance of natural light give the interior a modern yet timeless feel. Outside you will enjoy stylish curb appeal with a paver driveway – plus a COVERED LANAI overlooking a FENCED BACKYARD, and the spacious lot offers plenty of room for outdoor living. From golf, fine and casual dining to shopping, top-rated schools like Princeton Elementary, and easy access to I-4, 426, and 436, everything you love about Winter Park is right at your fingertips! This home offers the upgrades, the space, and the location you have been waiting for. Call today to schedule a tour and fall in love with your new HOME SWEET HOME!

Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)

Listing Agent: Jenny Wemert (407-809-1193)

Remarks: Charming MOVE-IN Ready Solid Block 3 bedroom, 2 bath Winter Park home. This home features updated kitchen and baths, newer flooring, newer Roof- 2021, Water heater-2023, AC-2016. The home has been re-plumbed and offers newer windows-2018. Beautiful Tongue-N-Grove Woodwork covers the ceiling & walls Bonus room/Den. The home offers a split floor plan and is constructed with plaster walls, its solid and energy efficient. The home is zoned for Top-Rated, sought after Winter Park High School, Maitland Middle and Lakemont Elementary. The very best location. This one won't last long..............

Listing is courtesy of: A+ REALTY PROFESSIONALS, INC (407-702-5243)

Listing Agent: Darlene Chance (407-247-2307)

Remarks: Pre-Construction. To be built. Discover a rare opportunity to build a fully custom residence in the highly sought-after Killarney Shores neighborhood of Winter Park—one of the last areas where new construction at this level remains attainable below $1.3M. Exclusively curated by The Hope Group, this offering pairs premier design with a seamless build experience alongside Deep Roots Construction, MJS Designers, and Collins & Co. From concept to completion, every detail is thoughtfully orchestrated, allowing the future owner to tailor finishes, layout, and architectural style to match their vision. Ideally positioned just minutes from Park Avenue’s renowned dining, boutique shopping, and vibrant lifestyle, the property also offers convenient access to I-4, College Park, and Downtown Orlando—delivering both prestige and connectivity. The proposed residence spans approximately 2,500 square feet and is designed with intentional flow, abundant natural light, and refined modern finishes. The layout allows for elevated indoor-outdoor living, with the option to incorporate a private pool and outdoor entertaining space. Located within close proximity to major medical centers, including AdventHealth Winter Park (approximately 2.5 miles), AdventHealth Orlando (approximately 4 miles), and Orlando Health Orlando Regional Medical Center (approximately 5 miles), this location offers both lifestyle and practical convenience for medical professionals and those seeking proximity to top-tier healthcare. Opportunities like this are increasingly limited in Winter Park—secure your homesite and begin designing a one-of-a-kind residence in one of Central Florida’s most desirable zip codes.

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

Listing Agent: Vinny Lay (407-756-4255)

Remarks: Under contract-accepting backup offers. Under Construction. In the heart of Winter Parks highly coveted Tree Streets, where quiet tree-lined roads and timeless charm define the neighborhood, this stunning new construction by LUIH Homes offers a refined blend of modern architecture. The home immediately captivates with its bold contemporary façade and thoughtfully designed floor plan. Inside, elegant living spaces unfold intentionally, beginning with a sophisticated dining room accented by a custom wine bar and wine cooler. The main living room serves as a dramatic focal point of the home, featuring a stunning statement accent wall anchored by a sleek electric fireplace. At the heart of the residence, the chef's kitchen is designed to impress. Outfitted with Calacatta quartz countertops, custom cabinetry, a hidden walk-in pantry, and a full suite of Thermador appliances, the space delivers both performance and beauty. The first-floor primary suite is a true private retreat, thoughtfully positioned for comfort and tranquility. Generous in scale, it features a spa-inspired bathroom with a freestanding soaking tub, dual vanities, an expansive walk-in shower, and a large custom walk-in closet designed for both style and functionality. Also located on the first floor is an additional guest bedroom, providing flexibility for visitors, multi-generational living, or a private office. Upstairs, a spacious loft offers an additional living area perfect for relaxing or gathering, while a cleverly designed hidden homework room adds a unique and practical touch ideal for work or study. Three additional bedrooms complete the upper level, each offering generous proportions and beautifully finished spaces. Outdoors, the home transitions into a private backyard retreat designed for year-round Florida living. A covered lanai with a fully equipped summer kitchen, complete with grill and sink, sets the stage for effortless outdoor entertaining. The expansive backyard features a resort-style pool and spa, surrounded by ample space for lounging, dining, and enjoying the serene setting. The location further elevates this exceptional residence. Nestled within Winter Park's beloved Tree Streets, the home offers the rare combination of quiet neighborhood charm with incredible convenience, just a short walk to Phelps Park, The YMCA, and only minutes from the boutiques, dining, and vibrant lifestyle of Park Avenue. Don't miss this rare opportunity to own a home that truly has it all.

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

Listing Agent: Christopher Christensen (407-312-8003)

Remarks: Completely Remodeled Winter Park Home – Prime Location Beautifully updated single-family home located in the heart of Winter Park. This residence was fully remodeled in 2019, offering peace of mind with new kitchen and appliances, updated bathrooms, new flooring, HVAC system, electrical, and plumbing. Ideally situated directly across from Advent Health Winter Park Hospital, this property provides exceptional convenience while remaining tucked into an established residential neighborhood. The functional floor plan offers comfortable living spaces filled with natural light, along with modern finishes throughout. Zoned for Winter Park’s highly regarded public schools, this home is well-suited for a primary residence or long-term investment. Easy access to major roadways, shopping, dining, and downtown Winter Park amenities. Move-in ready and centrally located — a rare opportunity in one of Orange County’s most desirable areas. Owner owns the house next door as well. Both properties for sale.

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

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

Remarks: Completely Remodeled Winter Park Home – Prime Location Beautifully updated single-family home located in the heart of Winter Park. This residence was fully remodeled in 2019, offering peace of mind with new kitchen and appliances, updated bathrooms, new flooring, HVAC system, electrical, and plumbing. Ideally situated directly across from Advent Health Winter Park Hospital, this property provides exceptional convenience while remaining tucked into an established residential neighborhood. The functional floor plan offers comfortable living spaces filled with natural light, along with modern finishes throughout. Zoned for Winter Park’s highly regarded public schools, this home is well-suited for a primary residence or long-term investment. Easy access to major roadways, shopping, dining, and downtown Winter Park amenities. Move-in ready and centrally located — a rare opportunity in one of Orange County’s most desirable areas. Owner owns the house next door as well. Both properties for sale.

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

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

Remarks: Welcome to 2423 Via Sienna, gracefully positioned on a quiet cul-de-sac in the heart of Winter Park. This charming, established enclave is just moments from the Winter Park Racquet Club, Phelps Park, the YMCA, and the renowned boutiques and dining of Park Avenue. This exceptional four-bedroom, three-and-a-half-bath pool residence has been taken to the studs and masterfully reimagined with timeless finishes and thoughtful design throughout. Upon entry, soaring ceilings and expansive windows create a light-filled, open interior ideal for both everyday living and elegant entertaining. The living and dining spaces are accented by tongue-and-groove ceilings, a gas fireplace, and bespoke built-ins, flowing seamlessly into a sun-drenched sunroom destined to become a favorite retreat. Chicago brick flooring, fixed glass windows, and accordion doors frame serene views of the private backyard oasis. The gourmet kitchen is both stunning and functional, featuring custom soft-close cabinetry, quartz countertops, floating shelving, exquisite millwork, and a full suite of Thermador appliances. A generous 4.9-by-10-foot island with storage on both sides anchors the space, complemented by a cozy breakfast nook and built-in bar. French doors provide effortless indoor-outdoor connection. Just beyond, a thoughtfully designed mudroom and pool bath with Chicago brick flooring offers convenient access to the pool area. A spacious first-floor bedroom—ideal as a guest suite, office, or den—along with a full bath completes the main level. Upstairs, the luxurious primary suite offers a private sanctuary with dual walk-in closets and a spa-inspired bath featuring separate vanities, soaking tub, steam shower, and private water closet. Two additional bedrooms share a well-appointed Jack-and-Jill bath with individual vanity areas for comfort and privacy. The expansive laundry room adds charm and practicality with a retro sink, built-in ironing board, and abundant storage. The tranquil backyard is designed for quintessential Florida living, showcasing a beautifully resurfaced pool surrounded by lush landscaping—perfect for entertaining or quiet relaxation. Additional highlights include engineered hardwood flooring throughout, designer lighting, a wrought-iron staircase, new baseboards and crown molding, fresh interior and exterior paint, newer roof (2023), two HVAC systems (2022 & 2023), and an oversized two-car garage with dedicated workshop space. Located within highly regarded A-rated schools.

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

Listing Agent: Wendy Williams Crumit (321-356-8590)

Remarks: Set on an oversized corner lot in one of the most desirable pockets of Winter Park, this 3-bedroom, 2-bath pool home blends character, location, and opportunity. The backyard is a standout feature, with a resurfaced pool finished in Tahoe Blue PebbleTec and positioned for open sky views, a rare find in a neighborhood known for its mature tree canopy. It creates a bright, inviting outdoor space that feels both private and expansive. Inside, the home has been thoughtfully updated while still leaving room for your own design vision. The layout offers comfortable living spaces with plenty of natural light and flexibility for everyday living or entertaining. Convenience is a major highlight. Located near top-rated schools, including Lakemont Elementary School, Maitland Middle School, Winter Park High School, and just minutes from local favorites like Park Avenue, Rollins College, and the Cady Way Trail. Nearby access to the SunRail adds another layer of accessibility. This location delivers a strong mix of lifestyle and connectivity, with dining, shopping, parks, and daily essentials all close by. Offered with clear motivation due to relocation, this is a rare chance to secure a well-located pool home with long-term upside in one of Central Florida’s most established communities.

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

Listing Agent: David Plasencia, Llc (407-579-9369)