5-Bedroom Homes for Sale in Maitland, FL

The Winter Park Chain is the context; the shoreline of Lake Minnehaha is the setting. A three-story, columned home opens with an honest, crafted tone: new low-profile concrete tile roof, operable cypress shutters with hand-forged hardware, Chippendale balustrades, and a beveled front door offering almost 6,200 sq. ft. curated for light, views, and everyday lake living. Inside, the home is bright

Brad Young HOMEVEST REALTY

Private setting within the exclusive Lake Maitland Owl Preserve, this spectacular five-bedroom contemporary residence was masterfully built in 2019 by award-winning E2 Homes. A dramatic 12-foot-tall wooden pivot-door makes a striking first impression, opening into a light-filled foyer, gathering, dining, and kitchen wide-open everyday living area with soaring two-story ceilings. A floating

Mick Night PREMIER SOTHEBY'S INTL. REALTY

Under Construction. Just steps from the boutiques and fine dining of Park Avenue, this brand-new bespoke estate by acclaimed builder Vimaro Homes delivers a rare combination of architectural sophistication and thoughtful design. Perfectly positioned on an oversized 0.34-acre lot, the residence encompasses over 5,200 square feet of refined living space, crafted with the finest materials and an

Julie Christensen COMPASS FLORIDA LLC

Pre-Construction. To be built. This is that house. Location, Architecture and Layout. Designed on one level on an oversized corner lot on the North side of Winter Park which allows an ease of in and out on a quiet and lovely location. This mid-century Frank Lloyd Wright inspired home could be one of Phil Kean’s best work yet, and certainly a unique addition to the Old Winter Park landscape.

Brad Grosberg PHIL KEAN REAL ESTATE LLC

Discover a rare opportunity in Dommerich Woods, a distinguished and established Maitland neighborhood celebrated for its rich heritage. Situated on .33 acre of lushly landscaped grounds, this remarkable property welcomes with paver drive and enjoys a tranquil setting along apeaceful creek connecting Lake Minnehaha and Lake of the Woods - creating an atmosphere of natural elegance and

David Van Wormer VANWORMER REALTY & DEVELOPMENT

Showpiece Charles Clayton Home in Gated Lake Colony EstatesEvery detail of this 5-bedroom, 4.5-bath plus office residence was designed to impress, including a full in-law apartment and an outdoor living space that feels like a private resort.Set on a prime corner lot, this home combines timeless craftsmanship with modern finishes: tile roof, travertine downstairs, hardwood upstairs, sleek

David Plasencia COLDWELL BANKER RESIDENTIAL RE

Nestled on a spacious corner lot in the highly sought-after Dommerich/Highland Park neighborhood, this distinctive two-story Mid-Century home offers both character and flexibility. With 5 bedrooms and 3 full baths, the layout is ideal for multigenerational living or accommodating guests with ease. Upstairs, the 5th bedroom serves as a private in-law suite, complete with a walk-in closet, full

John Forrester KELLER WILLIAMS REALTY AT THE PARKS

Behind private gates along the shores of Lake Maitland, this elegant Mizner-style Mediterranean estate offers an extraordinary opportunity to own a timeless lakefront masterpiece on the Winter Park Chain of Lakes. Encompassing approximately two acres of meticulously manicured grounds framed by soaring palms and mature live oaks, this exceptional property blends classic architecture with

Mick Night PREMIER SOTHEBY'S INTL. REALTY

One or more photo(s) has been virtually staged. Welcome to a private oasis in the heart of Maitland. tucked away on a quiet cul-de-sac in an exclusive gated community of just 19 custom homes. This one-owner estate offers a blend of elegance, space and serenity between picturesque Lake Sybelia and Lake Catherine. This five-bedroom, four-and-a-half-bath pool home with a three-car garage sits on an

Jo-Ann Lamar PREMIER SOTHEBY'S INTL. REALTY

Welcome to Maison du Lac – a breathtaking lakefront estate that epitomizes unrivaled luxury, timeless elegance, and an extraordinary lifestyle. Situated on an expansive 2.7-acre lot along the prestigious Winter Park Chain of Lakes, this extraordinary residence showcases over 120 feet of pristine lakefront with sweeping panoramic views of the longest stretch of Lake Maitland.Blending classic

Maggie Walas FORTUNE INTERNATIONAL REALTY

Experience the blend of timeless elegance and modern luxury in this Maitland estate a block away from Lake Sybelia. Completely renovated in 2007, every detail of this home exudes sophistication. A spacious paver driveway leads to a two-car garage, framed by lush tropical landscaping, decorative stone accents, and a charming fountain, creating an inviting first impression. The grand foyer welcomes

Peter Luu REAL BROKER, LLC

ACTIVE on the Market – Enhanced and Priced to Sell!Custom built in 2003 and secluded in an exclusive enclave of only six exquisite luxury homes, this 5-bedroom, 4.5-bath Mediterranean-style residence offers privacy, elegance, and an exceptional indoor-outdoor lifestyle. Designed around a stunning courtyard with sparkling pool, tropical landscaping, and outdoor lighting, almost every room on

Sandi Peery RE/MAX TOWN & COUNTRY REALTY

Welcome to this updated and architecturally unique 5-bedroom, 3.5-bathroom custom home, offering 3,292 square feet of luxury living in the heart of Winter Park. Step inside and you’re immediately greeted by gleaming porcelain tile floors, smooth modern non-textured walls, and soaring ceilings that create a light and airy feel. The spacious living room features custom wall details, crown molding,

Tiffany Pantozzi ALIGN REAL ESTATE 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