5-Bedroom Houses for Sale in Winter Park

One of the most coveted neighborhoods in all of Winter Park! This custom-built 5-bedroom, 5.5-bath residence was completed in 2017 and first sold in 2018. Lovingly maintained by the original owner and elevated with high-end designer finishes, the home showcases the impeccable vision of renowned designer Ted Maines, who reimagined much of the interior with timeless sophistication. Perfectly

Brian Scanlon SCANLON REALTY GROUP LLC

You have arrived to 1560 Woodland Avenue, a beautiful home in a prime location inside the Winter Park municipality, situated on a peaceful brick-paved street. There are five bedrooms and four and a half bathrooms spread out over 3,800 square feet in this stunning property. Featuring a welcoming pool and relaxing spa. A separate suite with its own entrance is available for use by the mother-in-law

Manny Alvarez LOKATION

Step into elevated Winter Park living with this exceptional Mediterranean-inspired estate. Built in 2020, every inch of this home was thoughtfully crafted with timeless architecture and sophisticated, high-end finishes. From the rounded stone entry feature and custom iron double doors to the soaring ceilings and designer lighting, this home instantly impresses. The spacious great room opens to a

Joe Devlin DEVLIN INVESTORS & ASSOCIATES

Experience the perfect blend of luxury, lifestyle, and location in this completely custom 2017 Lundev build, just one mile from the boutiques and dining of Park Avenue and less than 100 feet from access to Lake Osceola, perfect for paddleboarding or launching a canoe.Tucked away on a quiet, tree-lined street, this residence makes a striking first impression with it's stunning elevation

Brandon Geers COMPASS FLORIDA LLC

Discover luxury living in this custom Austin Homes 5 bedroom, 5 and one half bath transitional style home that offers a blend of modern and traditional elements coupled with a highly desirable Winter Park location. This residence boasts a sought-after open floor plan with 12-foot ceilings, wide plank wood flooring and truly exceptional detailed finishes throughout. You will feel instantly at home

Julie Bettosini STOCKWORTH REALTY GROUP

An exceptional custom home by award-winning Davila Homes, perfectly blending modern design and functionality. Located in sought-after Conwill Estates, just minutes from Park Avenue, this 5-bed, 4.5-bath residence features volume ceilings, floor-to-ceiling bronze sliding doors, and a seamless indoor-outdoor living experience.The chef’s kitchen showcases waterfall quartz countertops,

Mulcy Tenorio FLORIDA CONNEXION PROPERTIES

Award-winning Phil Kean design on a prominent corner lot in the heart of Winter Park, just minutes from Baldwin Park, Park Avenue, and East End Market—home to Michelin-rated dining and upscale retail. This 5-bed, 5.5-bath residence delivers clean lines, smart design, and seamless indoor-outdoor flow. Recognized with multiple honors, including the 2015 Parade of Homes 1st Place Award for Custom

David Hung KELLER WILLIAMS ADVANTAGE III

On one of Winter Park’s most scenic brick-lined streets, this exceptional two-story residence commands attention on a spacious corner lot, blending timeless architectural elegance with modern luxury. Built in 2016 by the highly regarded Rex-Tibbs Development & Construction, the home showcases quality craftsmanship throughout, from its striking curb appeal to its impeccably appointed interiors. A

Mick Night PREMIER SOTHEBY'S INTL. REALTY

Custom estate 5 bedroom pool home now available that exudes meticulous detail, luxury and designed for entertaining. The kitchen was completely renovated less than two years ago along with new solid hardwood floors now installed throughout the home. The kitchen features high end stainless steel Bosch appliances, natural gas cooktop, beautiful white timeless cabinets and quartz counter tops. A

Vonda Fields CHARLES RUTENBERG REALTY ORLANDO

Step into your dream home in Winter Park! This stunning 7,000 SF residence, nestled on a peaceful street in the coveted Vias neighborhood, offers ample space across three levels, making it an ideal choice for those who crave both room to spread out and a welcoming atmosphere. Gorgeous hardwood floors flow throughout the main living areas, enhancing the home's inviting, warm ambiance. The

Sylvester Harding SIERRA REALTY GROUP LLC

Custom Winter Park home completed in 2019 by FG Schaub Custom Home Builder. Contemporary Florida living awaits in this newly built home, boasting a spacious open floor plan spanning over 4,000 square feet with five bedrooms and five-and-a-half baths. Delight in the stunning gourmet kitchen, gas cooktop, oversized island and an extended walk-in pantry with cabinets. Distinctive features include

Michelle Hochfelder PREMIER SOTHEBY'S INTL. REALTY

An architectural tour de force in the heart of Winter Park. Designed by a premier builder of boutique homes and crafted with no detail spared, this 5-bedroom, 6.5-bathroom estate offers over 4,500 square feet of bold yet elegant living. A soaring 28-foot foyer sets the tone with dramatic scale, introducing the home through double-height French doors into expansive interiors showcasing

Ahmad Hassan COMPASS FLORIDA LLC

Vintage original 5-Bed, 3-Bath pool home with new roof on an estate-size lot adorned with mature landscaping and breathtaking views that overlook a natural wooded area in desirable Virginia Heights. This fabulous property could have a full renovation to make best use of the existing home, or the 16,000+ square foot lot offers the perfect opportunity to build the new home of your dreams and

Frank Ferrell FERRELL REALTY, INC.

Stunning 2020 Mediterranean Pool Home by M. Lahr Custom Homes in one of the sought-after neighborhoods of Winter Park. Experience unparalleled luxury in this breathtaking exquisite 5-bedroom, 4.5-bathroom home with bonus room that offers a perfect blend of comfort, and functionality. This exceptional residence features high-end designer finishes and exceptional craftsmanship throughout for modern

Rhonda Chesmore KELLY PRICE & COMPANY LLC

An Award-Winning Architectural Masterpiece built by Chris Salhab with Valdara Custom HomesCompleted 2024Parade of Homes Showcase Home – Grand Award WinnerAurora Awards – Custom Home Grand Award5,164 Sq Ft | 5 Bedrooms | 6 Bathrooms | Deeded Lake AccessWelcome to 1221 Richmond Rd, an extraordinary custom residence located in the coveted Virginia Heights neighborhood of

Audra Wilks KELLER WILLIAMS WINTER PARK

Discover luxurious living in the heart of Winter Park! Crafted with exquisite attention to detail, this 5-bedroom, 4.5-bathroom pool residence showcases absolute perfection and modern elegance. Built in 2018 by David Weekley Homes, the property boasts a captivating stone facade and a private backyard oasis featuring a saltwater, heated pool and spa with water feature, and ambient lighting — an

Kelly Price KELLY PRICE & COMPANY LLC

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

Maggie Walas FORTUNE INTERNATIONAL REALTY

Presenting 1112 Preserve Point Drive, Winter Park, FL! Offered at $8,500,000 this very rare and private, nearly 2-acre lakefront estate, is absolutely gorgeous and is available for the first time! Custom built by Phil Kean Design Group and located within Windsong's Preserve Point, this extraordinary Lake Berry home has it all including 1.97 acres of land adjacent to the historic Genius Preserve

Kelly Price KELLY PRICE & COMPANY LLC

One or more photo(s) has been virtually staged. Welcome to 1361 Palmer Avenue, a beautifully updated five-bedroom, 3.5-bath residence in the heart of Winter Park, Florida, 32789. This exceptional home has been meticulously maintained and extensively renovated, blending classic charm with modern design. Inside, you'll find a reimagined designer kitchen with premium finishes, ideal for everyday

Michelle Hochfelder PREMIER SOTHEBY'S INTL. REALTY

One or more photo(s) has been virtually staged. Experience the Charm of Winter Park in This Renovated Corner HomeWelcome to the beautifully updated gem of Winter Park!Located on a prime corner lot just three short blocks from the famous Park Avenue, this stunning residence spans over 2,200 square feet and has been completely transformed to blend style, comfort, and an unbeatable

Andres Ospina Rivera LPT REALTY, LLC

Discover this exceptional custom-designed modern pool home, ideally situated on a quiet street in Winter Park. This spacious residence offers 5 bedrooms, 4.5 bathrooms, and a large upstairs loft—providing the perfect blend of luxury, comfort, and functionality. From the moment you enter, you'll be captivated by the abundance of natural light and stunning hardwood floors that flow throughout the

Lisa Fleming FANNIE HILLMAN & ASSOCIATES

OPPORTUNITY AWAITS – PURE POTENTIAL IN WINTER PARK’S SEVILLA NEIGHBORHOOD! Rare, Tudor-style estate sits on an oversized 0.44 acre lot (19,217 SF) at the end of a quiet cul-de-sac and offers elevated views of Lake Sue. Originally built in the 1970’s, this well-built, concrete block home, offers a very spacious interior layout with 5-bedrooms, 5 full baths, 2 half baths, formal living & dining

Kelly Price KELLY PRICE & COMPANY LLC

This home is the perfect blend of resort luxury and farmhouse charm, with high-end finishes and features that cater to both relaxation and entertaining. From the resort-style backyard with a magnificent Saltwater Pool, lovely green space around the koi pond to the HGTV-worthy Interior with an entertainer’s dream kitchen, this has it all. The spacious split-bedroom floor plan, luxurious primary

Eileen Winfrey LPT REALTY, LLC

Nestled in peaceful Winter Park, your new contemporary home boasts expansive open living areas featuring 12-foot ceilings, five en-suite bedrooms, and outdoor living spaces spanning two levels.The semi-circular driveway and landscaped courtyard lead you to the front entry, adorned with frosted-glass double doors. Inside, the sweeping view of the spacious open living, dining, and kitchen spaces

Anthony Consalvo FLORIDA ONE REAL ESTATE LLC

Just Listed ~ Stunning lakefront home in Winter Park that has been completely remodeled and offers 4 bedrooms, a bonus room, and guest apartment! This home is exquisite from top to bottom and features elevated ceilings, crown moldings, designer fixtures and wall coverings. Large picture windows overlook Lake Sue from the living room, dining room, and kitchen. The kitchen is gorgeous and offers

Leah Bonich KELLY PRICE & COMPANY LLC

Custom Waterfront Estate located in the heart of Winter Park with a covered Boat Dock on Lake Maitland, the largest of the Winter Park Chain of Lakes, and walking distance to historic Park Avenue. A timeless Neoclassical Italian home that exudes luxury and sophistication, spanning a total of 7,916 square feet. Built by Charles Clayton. Designed by Marc Michaels. The main house boasts over 7,100

Rachel Peters THE AGENCY ORLANDO

Welcome to this rare Winter Park gem offering unmatched flexibility and investment potential. Whether you’re looking for a turnkey rental property, a multigenerational living solution, or a home with a private in-law or student suite, this property delivers! Each spacious unit boasts 3 bedrooms and 2 bathrooms, designed with a modern, elegant aesthetic. With dual living areas, kitchens, and

Dominick Florio RE/MAX TOWN & COUNTRY REALTY

New Home Nestled in the esteemed The Vias area and near the WPRC. Situated on a secluded street, it occupies an approximately 0.58-acre lot with an expansive backyard landscape that is truly captivating. This exquisite home encompasses five bedrooms and six-and-a-half bathrooms with a four-car garage. An indomitable presence is seen in its immense and grand pivoting iron door which directs you to

Marcio Tannus LA ROSA REALTY HORIZONS LLC

**Luxurious Winter Park Estate with Detached TWO bedroom Guest House** RENOVATED POOL HOME with NO HOA! TWO Primary Bedrooms located on the main floor! Welcome to a world of unparalleled luxury and elegance in the heart of historic Winter Park, FL. This exquisitely renovated two-story pool home, set on a sprawling corner lot, offers a rare opportunity to experience the pinnacle of

Christopher Soucy REALTY ONE GROUP MVP

One or more photo(s) has been virtually staged. NEW IMPROVED PRICING! Newly Renovated Partially Furnished Home in the Beautiful Via’s of Winter Park! Privately located on a large wrap around corner lot. It is meticulously maintained with eye-catching curb appeal with mature magnolia trees and beautiful landscaping with newly installed lighting to illuminate at night. This stunning 6 bedroom and

Iram Hashmi LOKATION

Welcome to your dream home—a masterfully designed, Dutch West Indies-inspired custom residence that blends timeless elegance with modern luxury. Built by FG Schaub Custom Homes, this home features five bedrooms, five full bathrooms, two half bathrooms, and a dedicated home office, all thoughtfully designed for comfort and sophistication within 4,055sqft. of living space.Stepping into the

Laura Earl CORCORAN PREMIER REALTY

Under Construction. Brand-New 2025 Mediterranean Luxury in Historic Winter ParkIntroducing 1473 Berkshire Avenue — a just-completed luxury residence nestled on one of Winter Park’s most peaceful, tree-lined, and century-old streets. This two-story Mediterranean masterpiece delivers the perfect blend of timeless architecture and contemporary design, offering 5 bedrooms, 4 bathrooms, and nearly

Milena Fernandes GOLDEN GROUP REALTY LLC

Under Construction. Scheduled completion March 2026. New construction in the City of Winter Park! There is still time to make personalized finish selections. This deep 56 x 157 lot is Winter Park's best kept secret, located in a quiet pocket of 32789. This property is centrally located, less than 10 minutes to Park Ave, and zoned for Orange County schools: Dommerich Elementary, Maitland Middle,

Kristen Hamilton LOMBARDO TEAM REAL ESTATE LLC

Under Construction. UNDER CONSTURCTION.....Step into this stunning West-Indies inspired luxury home crafted by Nautilus Homes, where tropical charm meets timeless elegance. An architectural masterpiece in the heart of City of Winter Park. Exquisite Interior Features that are offered starts with entering the grand foyer with 10ft high ceiling and the flex room and formal dining to your left and

Prentice Williams EXP REALTY LLC

New Hamptons-style residence offering a seamless blend of elegance and modern sophistication. A gated entrance opening to a circular driveway and motor court, set the stage for enjoying this exceptional estate. As you enter home, an impressive 2-story foyer with a glass-paneled staircase wraps around a temperature-controlled wine room and a transparent glass elevator, effortlessly connecting all

Mick Night PREMIER SOTHEBY'S INTL. REALTY

Under Construction. Completion September 2025, Nestled in the heart of Winter Park, this luxurious custom-built home seamlessly blends elegance, functionality, and thoughtful design. Boasting 5 bedrooms, 4.5 bathrooms, and 2,964 sq/ft of unparalleled living space, every detail has been meticulously crafted for modern living. From the moment you step inside, an elegant gallery entrance welcomes

Leighton Hope COMPASS FLORIDA LLC

Pre-Construction. To be built. Price Improvement!!! Your Dream Home Is Ready To Be Built!! Pre-Construction Opportunity! Build-to-Suit! Buyers who act now can still pick finishes and style! Build your custom dream home with renowned Konkol Homes in one of Central Florida’s most desirable areas! This nearly 1/4-acre lot is perfectly situated near Baldwin Park, East End Market, Audubon Park K-8,

Farah Bloom KELLER WILLIAMS WINTER PARK