Recently Sold in Maitland, FL

6 Beds ⋅ 10 Baths ⋅ Lake Maitland Manor SubDv. ⋅ 32751 Zip Code

Welcome to Maison Du Lac, nestled within the sought after Winter Park chain of lakes, this magnificent 11,668 sq ft estate presents an unparalleled living experience on 2.73 lush acres. With meticulous attention to detail and an expansive layout, this home offers 5 suites plus an opulent master wing, complete with its own office, sauna, and gym, ensuring privacy and luxury at every turn. Enter through the 14-foot custom iron front door, a statement piece valued over $50K, to discover a world of refined elegance. The main great room, illuminated by a "luxury hotel" crystal chandelier worth over $100K, sets the tone for an interior professionally designed with custom artwork. State-of-the-art energy-saving windows bathe the space in natural light, highlighting the exquisite craftsmanship and state-of-the-art appliances that adorn the home. The master wing is a sanctuary of tranquility, featuring a secret safe room within the master bathroom for ultimate privacy. His and hers massive walk-in closets offer lavish conveniences, including a built-in watch winder and a special shoe closet for her, catering to the most discerning tastes. This estate is an entertainer’s paradise, boasting a summer kitchen, a bar, and entertainment areas designed for hosting memorable gatherings. The brand new, completely rebuilt dock invites leisurely days by the lake, while the 6-car garage accommodates any automotive enthusiast. This residence combines modern convenience with peace of mind, equipped with a state-of-the-art smart home system and an alarm monitoring system. The privacy gates ensure a secluded retreat, making this home a secure haven of luxury. Over $3 million in renovations, including a brand new $350K roof and landscaping exceeding $400K, have transformed this estate into a masterpiece of design and comfort. The enormous walk-in butler pantry and professional interior design elevate the home’s functionality and aesthetic appeal. This estate is more than a home; it’s a lifestyle offering, professional interior designed by MAX Home Design crafted for those who seek the ultimate in luxury, privacy, and lakeside living. Welcome to your exclusive retreat on Lake Maitland, where every detail reflects your desire for the extraordinary. Bedroom Closet Type: Walk-in Closet (Primary Bedroom).

570 Manor Road, Maitland

$8,925,000

5 Beds ⋅ 8 Baths ⋅ Adams Grove SubDv. ⋅ 32751 Zip Code

Villa Serenata, a lakefront legacy on Lake Maitland. Behind private iron gates along the storied shores of Lake Maitland, Villa Serenata presents a rare opportunity to own a distinguished Mediterranean estate on the renowned Winter Park Chain of Lakes. On approximately two acres of meticulously curated grounds, this extraordinary residence feels less like a home and more like a private resort, crafted for those who appreciate timeless architecture, thoughtful design and elevated lakefront living. A sweeping circular driveway welcomes you beneath a canopy of soaring royal palms and majestic live oaks, immediately setting the tone for what lies beyond. As the automated gate opens, the property reveals itself as a serene sanctuary where elegance and privacy coexist in harmony. The 6,634-square-foot main residence showcases interiors by acclaimed designer Ted Maines, unfolding across two levels of refined sophistication. The Mizner-inspired living room commands attention with dramatic 24-foot wood-beamed ceilings and twin walls of arched French doors, one framing sweeping views of Lake Maitland’s shimmering waters, the other opening to a sun-dappled courtyard where mornings naturally begin with coffee and quiet reflection. The upper level is devoted entirely to the primary suite, creating a private retreat complete with a heatless gas fireplace, spa-caliber bath with soaking tub and steam shower, a bespoke dressing room with custom built-ins, and a rooftop terrace with glass railings offering remarkable lake views. Three additional bedroom suites, each with an en-suite bath and generous walk-in closet, provide comfort and privacy for family and guests alike. At the heart of the home, the chef’s kitchen is equipped with Sub-Zero and Wolf appliances, custom cabinetry, and an expansive prep island designed to transition seamlessly from intimate family meals to catered gatherings of 50. The formal dining room features a dramatic curved wall of windows, turning every meal into a lakefront experience, while the richly paneled library and office offer a quiet space for focused work or relaxed reading. Complementing the main residence is a thoughtfully designed guest compound totaling 1,540 square feet. A private media pavilion delivers a state-of-the-art theater and listening room for film enthusiasts and audiophiles, while the one-bedroom guest apartment above provides a fully appointed living space with kitchen, living area and private entry, ideal for extended family, visiting guests or live-in staff. Outdoor living is equally exceptional. Resort-style travertine surrounds the pool amid lush tropical landscaping, creating a tranquil setting for sun-filled afternoons. A covered lanai with full summer kitchen flows effortlessly from the family room, while an expansive open-air terrace extends from the great room, an inviting backdrop for sunset cocktails overlooking the lake. Villa Serenata is more than a residence, it is a legacy estate, offering privacy, architectural distinction, and a lifestyle centered on one of Winter Park’s treasured waterfront settings.

1640 E Adams Drive, Maitland

$6,650,000

4 Beds ⋅ 6 Baths ⋅ Hollieanna Shores 1st Add SubDv. ⋅ 32751 Zip Code

Sold data entry.

119 Whitecaps Circle, Maitland

$6,000,000

4 Beds ⋅ 6 Baths ⋅ Hollieanna Shores 1st Add SubDv. ⋅ 32751 Zip Code

Truly magnificent estate on Lake Maitland — part of the Chain of Lakes with 100 feet of water frontage. Tastefully designed interior with over 6,400 square feet of living space, four bedrooms, five-and-a-half baths, a bonus room, a home office, a kitchen, and a wine cellar. Elegant formal living room with fireplace and formal dining room. Spacious gourmet kitchen comes with Sub-Zero appliances, gas range, granite countertops, access to the back patio, and water views. The formal dining area is just off the living room, which features a beautiful fireplace and built-in cabinetry. Beautiful travertine flooring, vaulted ceilings, crown molding, and custom built-ins. The most spectacular view of the lake was assigned to the primary suite upstairs. The home office or additional bedroom connects to the primary suite for added convenience for working or infant care. Three additional bedrooms with en-suites and plenty of closet space are upstairs. Private backyard, screened-in patio, gorgeous swimming pool, and a hot tub — all overlooking the lake. Meticulous landscaping where every inch is accounted for. Elegant details, natural stone flooring, 12-foot wood-beamed ceilings, and recessed lighting throughout. Three-car garage and a private gate for extra privacy. Home includes a covered boat dock with a lift. New roof, AC units, and copper gutters. Enjoy lake living on the Winter Park Chain of Lakes with amazing sunrise and sunset views.

119 Whitecaps Circle, Maitland

$4,075,000

4 Beds ⋅ 7 Baths ⋅ Lake Maitland Manor SubDv. ⋅ 32751 Zip Code

Embrace the epitome of luxury living with this extraordinary lakefront estate located in the heart of Maitland, where endless possibilities await. This expansive custom-built residence, spanning nearly 6,000 square feet, presents the rarest of opportunities. Whether you envision moving right in, updating the existing custom residence, or building anew on this coveted 2-acre high-and-dry lakefront lot, the potential is limitless. The maturely landscaped driveway meanders to a circular paver roundabout leading you to the custom leaded glass entry doors. The foyer makes way to the expansive light filled formal living room boasting high ceilings, a wall of windows, a gas fireplace, and spectacular views of the lush backyard rolling gently down to unobstructed views of Lake Maitland. The chef’s kitchen, equipped with custom cabinetry, a stunning copper stove hood, double ovens, and spacious countertops, makes way to the open glass breakfast nook inviting you to create a culinary haven tailored to your every desire. Adjacent to the kitchen, lies the formal dining room, complete with slate tile and majestic front garden vistas! The first-floor primary bedroom, with its panoramic water views, dual walk-in closets, and spa-inspired bathroom, presents an opportunity to enjoy a luxurious retreat that exceeds your expectations. Just outside the primary bedroom is a stately office with custom wood paneling, a morning bar, and two-story bookshelves complete with a sliding ladder and French doors that lead to the covered porch with stunning lake views. Downstairs, two additional bedrooms and a Jack and Jill bathroom offers ample space for family and guests, while the upstairs in-law suite, complete with a private balcony overlooking the lake provides a spacious family room area, and full kitchenette, making it the perfect retreat for your most coveted guests, they'll never want to leave their very own sanctuary! The media and game room is second to none boasting an oversized wet bar with counter seating, an additional full bath and a generous closet behind hidden glass doors. The oversized 4-car garage with a spacious storage room ensures that your vehicle and hobby needs will all be met. The nearby oversized laundry area and mudroom, complete with an additional full bathroom is beyond practical. Relish in early morning sunrises and daily duck visits from your massive screened-in rear patio, and private composite dock with a covered boat lift assures you appreciate the extraordinary views of Dog Island, Isle of Sicily, and the Winter Park Racquet Club. The original regulation-size tennis court, partly shaded by an abundance of Florida citrus trees, has the potential for pickleball courts, basketball or multi-sports court, offering a blank slate for creating your ultimate recreational space. Situated walking distance from famed Luke's Kitchen and Bar, Antonio’s, and other fine restaurants, and with Winter Park’s--Park Avenue Boutiques and restaurants only 2.5 miles away, this extraordinary lakefront estate presents a once-in-a-lifetime opportunity to build or update your dream home in one of Central Florida’s most sought-after locations. Seize this chance to make your mark on luxury waterfront living and create a legacy that will endure for generations to come!

580 Manor Road, Maitland

$3,950,000

5 Beds ⋅ 5 Baths ⋅ Maitland Shores SubDv. ⋅ 32751 Zip Code

Exquisite contemporary waterfront retreat in Maitland. Experience modern luxury and serene waterfront living in this breathtaking five-bedroom, 5.5-bath canal-front home, newly built in 2024. Positioned on a quiet dead-end street in Maitland, this architectural masterpiece offers an unparalleled lifestyle on the Winter Park Chain of Lakes. Enter through the stunning 10-foot glass pivot door into a soaring foyer where a floating wood and glass staircase sets a dramatic tone. The expansive great room boasts a two-story ceiling and a wall of glass doors that seamlessly blend indoor and outdoor living. Go outside to your private oasis featuring a covered lanai with remote-controlled screens, a summer kitchen, gas fireplace, resort-style pool and spa, putting green, and a covered boat dock with a lift and jet ski platform, all overlooking tranquil Howell Branch Creek with direct access to Lake Maitland. The heart of the home is the chef-inspired kitchen, complete with dual oversized islands, sleek high-gloss custom cabinetry, integrated refrigerator and freezer columns, a wine refrigerator, built-in coffee maker, and a striking hood vent above a six-burner gas range. Adjacent is a stylish dining room framed by a floor-to-ceiling glass wall offering captivating water views. The main-level primary suite is a sanctuary with a private sitting area, dual walk-in closets, and a spa-style marble wet room with combined soaking tub and rainfall shower. A home office with lush front yard views, an elegant guest suite, a full bath, and the first of two laundry rooms complete the first floor. Take the elevator or statement staircase to the second level, where you'll find two additional bedrooms with en suites and walk-in closets, a fifth bedroom, a full bath, a second laundry room, and a 24-by-14-foot game room with wet bar, ideal for entertaining. Additional highlights include a three-car side-entry garage, an outdoor shower, a storage room, and verdant landscaping adorned with majestic cypress and oak trees draped in Spanish moss. Just minutes from the boutiques and fine dining of Winter Park’s Park Avenue, with easy access to major highways, hospitals, and both international and executive airports. This is Florida luxury redefined, private, peaceful and perfectly appointed.

33 Eastwind Lane, Maitland

$3,495,000

4 Beds ⋅ 5 Baths ⋅ Adams Grove SubDv. ⋅ 32751 Zip Code

Home is Sold as is. Septic Tank on property. Septic tank works in conjunction with the city sewer system.

1740 E Adams Drive, Maitland

$3,385,000

4 Beds ⋅ 5 Baths ⋅ Ravndals Rep SubDv. ⋅ 32751 Zip Code

Tucked away at the end of a quiet cul-de-sac, this serene lakefront retreat is sited on a lush 1.21-acre lot w/ 187 feet of shoreline on tranquil Lake Nina—part of the Winter Park Chain of Lakes—this 4-bedroom, 4.5-bathroom, 4,997-square-foot estate blends Santa Barbara-style charm w/ modern sophistication in one of Central Florida’s most desirable settings. A meandering drive leads you to a semi-circular paver driveway that welcomes you home. A deep, covered front porch provides a gracious entry, setting the tone for the calm, understated elegance found throughout. Once inside, nearly floor-to-ceiling windows span the entire rear elevation, offering breathtaking lake views from every angle & filling the home w/ natural light. To the right of the foyer, a cozy formal living room w/ a wood-burning fireplace invites quiet conversations or evening relaxation. To the left, the spacious dining room features a built-in buffet designed to preserve unobstructed views of the water. Just beyond, the newly renovated kitchen is a standout including a La Cornue French gas range, Monogram appliances, a concrete farmhouse sink, wide-plank oak flooring, luxury lighting & striking marble counters. A hidden scullery/laundry area offers practical overflow, connecting the kitchen to the oversized, air-conditioned 2-car, side-facing garage w/ built-in storage & a dedicated gym or flex room. Moving through the heart of the home, a large family room awaits—framed by soaring ceilings with cedar beam accents & outfitted w/ automated shades for comfort & privacy. The primary suite occupies its own wing & features a gas fireplace, dual walk-in closets, a spa-style bath, & 2 separate flex rooms currently used as an office & art studio. On the opposite side of the home, a tucked-away powder bath conveniently serves both guests & the pool area, while an additional en-suite bedroom downstairs offers privacy for guests or multi-generational living. Upstairs, two more bedrooms w/ en suite baths flank a generous loft w/ amazing lake views. Step outside & the setting is nothing short of spectacular. The resort-style backyard was designed for entertaining & unwinding alike, w/ multiple fire pits, a sparkling pool & raised spa & an outdoor kitchen complete with grill, pizza oven, built-in space for Green Egg, sink & refrigerator. The expansive lawn gently slopes toward the lake, leading to a rare, fully outfitted dock w/ a covered boathouse, lift, dual jet ski slips & utilities for water & electric—perfect for sunset cocktails or launching into the larger chain of lakes. Architectural details throughout the home include Mexican tile, natural wood & stone finishes, vaulted ceilings, metal accents, & custom lighting—thoughtfully layered to create a warm & inviting atmosphere. Major improvements include a home repipe (2020), updated electrical (2019), 3 new HVAC systems (2022), new garage doors (2021), & recently installed paver hardscape designed to accommodate ample parking for family & guests. In a sought-after Maitland lakefront enclave, this home pairs top schools w/ rare privacy & convenience. Lake Nina provides a quiet, scenic backdrop, yet a short, easily navigable canal offers direct access to the expansive waters of Lake Maitland & the greater Winter Park Chain—making it as ideal for tranquil mornings as it is for adventurous afternoons on the water. More than a home, this property is a lifestyle, a legacy & a front-row seat to the best of lakefront living.

645 Manor Road, Maitland

$3,359,000

5 Beds ⋅ 6 Baths ⋅ Oaks Maitland SubDv. ⋅ 32751 Zip Code

Welcome to this exceptional Phil Kean built home that offers luxurious features and ample space for comfortable living. With 5 bedrooms, 5.5 bathrooms, and an impressive 5013 square feet, this home is ideal for a large family or those who love to entertain. Situated on an elevated lakefront view, you'll enjoy breathtaking scenery and a tranquil atmosphere. As you step inside, you'll be greeted by the elegance and craftsmanship that defines this residence. The home boasts a two-car garage, providing convenient parking for your vehicles. The interior is adorned with high-end finishes and luxury appliances that will make everyday living a pleasure. One of the highlights of this home is the outdoor living space. Imagine hosting memorable gatherings with family and friends in the expansive outdoor kitchen, complete with all the amenities you need for al fresco dining. The saltwater pool with a sun deck offers a refreshing retreat during hot summer days, while the massive Lani with roll-down screens provides a comfortable space to relax and enjoy the view. For those who love boating and water activities, this home is a dream come true. It features a private boat dock with Trex decking, allowing easy access to the Winter Park Chain of Lakes. The massive lot provides ample parking space for your guests, ensuring that everyone feels welcome. Inside, you'll find a loft area that can serve as a versatile space for guests or additional entertainment. The loft is complemented by a massive guestroom, providing privacy and comfort for visitors. Additionally, the whole house generator ensures uninterrupted power supply, and the new AC installed in 2023 keeps the home cool and comfortable year-round. In the evenings, gather around the gas fire pit and enjoy cozy conversations under the starlit sky. This energy-efficient home and its features ensure that you can enjoy modern amenities while being mindful of the environment. Don't miss out on the opportunity to own this extraordinary Phil Kean built home. With its spacious layout, stunning lakefront view, and abundance of amenities, it offers the perfect blend of comfort, style, and functionality. Contact us today to schedule a private tour and make this dream home your own!

1504 The Oaks Drive, Maitland

$3,200,000

4 Beds ⋅ 3 Baths ⋅ Hollieanna Shores 1st Add SubDv. ⋅ 32751 Zip Code

One of a kind and once in a lifetime opportunity! A stunning lakefront peninsula with panoramic views off the north shore of Lake Maitland, the largest lake on the famed Winter Park Chain of Lakes, is now available. The estate is surrounded on 2 sides with approximately 300ft of lake frontage, 1.54 acres total and .7 acre dry. The home was designed by Nils Schweizer, a student and representative of Frank Lloyd Wright in Central Florida. Was later renovated adding a pitched roof and screened lanai with a pool/spa overlooking the lake! The 4 bedroom, 2.5 bath and 3 car-garage home with workshop has an abundance of windows and viewing areas to capture the beauty of central Florida lakes. This unmatched property has sunrise and sunset views looking out to Dog Island, Summerland Avenue tip, and the Isle of Sicily. The paver-drive and walkway lined with crepe myrtles, plumeria trees and hanging stag horn ferns welcome guests to the covered front porch and the dramatic foyer. Steps lead to the upper living room with wood floors, fireplace and 3 walls of glass and a balcony for breathtaking views of Lake Maitland. Nearby is an office with built-ins, ceiling fans and French doors opening to the immaculate landscape. The east wing leads to the primary bedroom having gorgeous views of sunsets, built-ins, fireplace and spacious contemporary bath: oversized walk-in shower, whirlpool tub, dual vanities and closets. Nearby is the dining room and custom kitchen. The dining room has built-ins and glass sliders to covered pool lanai - perfect for al fresco dining with pool and lake views. The kitchen has designer cabinets, granite counters, butcher block island and pass-through window to the pool wet bar. The kitchen sitting bar opens to the family room with wood floors, a breakfast nook and sliders to the screened pool lanai with 270 degree views of water! The north wing has 3 additional bedrooms and a full bath. The bonus room with vaulted ceilings, fans and glass sliders is ideal for a personal gym, theatre, or large den: it opens to either the 3-car garage or paver walkway to the workshop and backyard. A year-round personal resort with noteworthy plants for the gardener, dedicated workshop, hot tub and large pool overlooking the lake The partially enclosed boat house with a sitting deck is a special spot to enjoy sunrises and sunsets! Home’s generator and 250 gallon propane tank assure you of power! Renovate the current home or start fresh to build your dream home! This property is being sold as-is. The adjacent cleared lot on 125 Whitecaps Circle is also for sale. Purchasing both properties would give the new owner a very unique and stunning peninsula parcel on Lake Maitland on the famed Winter Park Chain of Lakes! See MLS#O6279215

127 Whitecaps Circle, Maitland

$3,193,000

5 Beds ⋅ 5 Baths ⋅ Northshore Estates SubDv. ⋅ 32751 Zip Code

Welcome to this charming stately lakefront estate, a true gem straight from the pages of Southern Living—just minutes from Winter Park and the finest dining in Maitland, all on the serene shores of Lake Sybelia. From the moment you arrive, the large, inviting porch with it's charming swing beckons you into a home flooded with natural light and warm wood floors and a thoughtfully designed layout. The heart of this home is the expansive kitchen, seamlessly flowing into the family room and offering French doors that lead to a picturesque backyard. The downstairs primary suite provides a luxurious retreat, featuring large walk-in closets and a beautifully remodeled bathroom with a soaking tub and dual vanities. A private guest suite is conveniently located off the family room, offering its own entrance and separation from the rest of the home. Upstairs, you'll discover three generously-sized secondary bedrooms, a dedicated theater room, a private study, and a spacious bonus room complete with custom built-ins—perfect for play, work, or relaxation. Move right in as this home has not only been freshly repainted but all bathrooms have been remodeled and refreshed. Step outside to your personal private oasis, with no rear neighbors, where a newly remodeled pool with a sun shelf, stunning decking, and fire bowls set the perfect ambiance for both relaxation and entertaining. The lush side yard enhances the home's charm, while the boat dock provides the perfect spot to watch breathtaking sunsets or enjoy water sports on Lake Sybelia. This exceptional property offers the perfect blend of comfort, style, and lakeside living. Don’t miss the opportunity to make it your own!

571 N Lake Sybelia Drive, Maitland

$3,150,000

3 Beds ⋅ 2 Baths ⋅ N/A SubDv. ⋅ 32751 Zip Code

Welcome home to your recently remodeled lakefront oasis located on approximately 119’ of waterfront on the shores of Lake Minnehaha on the Winter Park Chain of Lakes. Everything you have been looking for is finally here. In late 2021, this home went through an extensive renovation from the ground up, the entire interior was completely gutted with all new drywall, electric, plumbing, lighting new 3 zone AC, home automation and so much more. Tucked away off a quiet street, this home features incredible panoramic views of the lake, meticulous landscaping and large oaks that create a canopy-like entrance. Entering the house, you immediately take in the picturesque views of Lake Minnehaha- the views from the living room and kitchen are simply incredible. The interior layout was thoughtfully changed to make the spaces open and grand. The completely brand-new kitchen has custom cabinets and all new appliances, as well as a butler’s pantry that features an ice maker and plenty of room for all the extra appliances. The Calcutta gold quartz counter tops accent the solid wood cabinets and the amount of light that comes in the home is simply stunning. The redesigned master bedroom and bath has everything you need, including sliding doors that lead out to the deck and salt water pool that was put in late 2022. On the opposite side of the home, you will find two nicely appointed bedrooms that share a brand new bathroom. The den/office is the perfect spot to kick back and enjoy views of the backyard. As you walk outside to your large screened-in back porch, you will notice how quiet and serene this location really is. The new heated salt water pool is elevated and provides a great spot to hang out with family and friends. When it’s time to get out on the boat, simply walk down your private path to your very own boat dock. If taking out the jet ski is more your thing, simply hop on and cruise the 6 lakes that make up the Winter Park Chain of lakes. With landscape lighting throughout, this property is unique and will be hard to replicate. If you need garage space this has it too- with 3 air conditioned spaces you will have plenty of space to park your toys. Current owner has drawings to recreate the garage and have space above that can be additional bedrooms or home gym - providing an additional 1500+ square feet of living space. Home is zoned for A-rated public schools, and you are just minutes from award-winning restaurants and boutique shops along Winter Park’s famed Park Avenue, the Racquet Club and Interlachen Golf & Country Club.

644 Bentley Ln, Maitland

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