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570 Manor Road, Maitland
$11,300,000
6 Beds ⋅ 10 Baths ⋅ Lake Maitland Manor SubDv. ⋅ 32751 Zip Code
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 Mediterranean architecture with state-of-the-art modern enhancements, Maison du Lac is a stunning fusion of enduring charm and contemporary sophistication. Originally constructed with timeless materials – including stucco exteriors and expansive windows – the home has been meticulously transformed into an 11,668-square-foot architectural masterpiece. Clean lines and open-concept living harmonize with rich textures and refined details, resulting in an environment that is both stately and smart. Upon entering through the grand 14-foot custom iron door, you are greeted by soaring dual staircases and exquisite finishes in marble, granite, and intricate moldings that reflect the home’s bespoke craftsmanship. A showstopping, $250,000 crystal chandelier—custom-designed and operable at the touch of a button—crowns the expansive great room, setting a dazzling tone for the professionally curated interiors. A private elevator adds convenience and accessibility across all levels of the home. The fully reimagined kitchen is a culinary showpiece, featuring top-of-the-line Wolf appliances, gleaming Cambria countertops, a large walk-in pantry, and expansive prep space ideal for entertaining at any scale. Whether hosting a lavish dinner or a relaxed brunch, the kitchen delivers both impeccable style and everyday functionality. The private master wing is an indulgent retreat, complete with a cozy fireplace, executive office, sauna, fitness room, and dual custom walk-in closets. Five additional en-suite bedrooms are thoughtfully positioned for maximum privacy, offering luxurious accommodations for family and guests. With seven full bathrooms and three half baths, the residence is ideally equipped for both refined daily living and grand-scale entertaining. For effortless indoor-outdoor living, multiple entertainment spaces flow seamlessly onto a sprawling lakefront patio. The outdoor summer kitchen, complete with a powered screen enclosure, provides the perfect setting for alfresco dining while enjoying sunset views over the water. A brand-new dock with a boat lift invites leisurely days spent boating, fishing, or simply relaxing on the lake. Outside, the estate continues to impress. Two serene fishponds with fountains create a tranquil sense of arrival, while the fully fenced and gated grounds ensure ultimate privacy. The residence is equipped with a full-home LUTRON smart system, offering intuitive control of lighting, ambiance, and automation. Additional features include a six-car garage, a resort-style swimming pool, newly updated landscaping, and custom exterior lighting. Maison du Lac is more than a home, it’s a lifestyle of distinction, privacy, and effortless sophistication. This is the lakefront living at its finest.

570 Manor Road, Maitland

570 Manor Road, Maitland
$10,300,000
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

1640 E Adams Drive, 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

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

580 Manor Road, 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

33 Eastwind Lane, 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

645 Manor Road, 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

127 Whitecaps Circle, 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

571 N Lake Sybelia Drive, 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

644 Bentley Ln, 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

1011 N Lake Sybelia Drive, Maitland
$2,875,000
5 Beds ⋅ 6 Baths ⋅ Backus & Gunion Add SubDv. ⋅ 32751 Zip Code
Stunning boat/ski lakefront home w 5,697sf on 1.5+- upland acres. 5 bed 4.5 bath w detached 1,100sf guest house over 3 car garage. Minutes from downtown Winter Park/Park Ave upscale shopping & dining. 10-minute drive to downtown Orlando. Features: gourmet kitchen, pool/spa, summer kitchen, expansive storage, lakefront views. The open concept kitchen is a true chef's delight featuring every accoutrement your heart would desire. A state-of-the-art refrigerator and freezer, double ovens, Ice maker, 2 wine/beverage fridges with a gourmet cook top, massive granite island and walk in pantry. This lovely kitchen is adjacent to the large family room and bonus room that each look out on to beautiful lake Sybelia. The downstairs flooring is a warm wide planked wood while the entrance and hall includes stunning large travertine tiles. The downstairs primary bedroom provides a private retreat of tranquility with breathtaking lake views as well as a large primary bathroom and walk in closet. You’ll find four substantial sized bedrooms and 2.5 baths upstairs with a bonus gamer room, study area and upstairs 2nd laundry room. The large front yard and lake views aren’t the only outdoor highlights the expansive property has to offer. You’ll enjoy entertaining and grilling in the large, covered summer kitchen or enjoy swimming in the beautiful crystal blue pool. It’s a gardeners delight with three large garden boxes and huge storage shed. There is also a large courtyard, half-court basketball court in addition to the shady large, grassed back yard. It’s truly a family home with tons of wonderful, usable and thoughtfully designed spaces with something for everyone to enjoy. Even your cars will be delighted with the oversized three car garage with extra space for a home gym as well. Come discover what living in Maitland is all about. This private and secluded street is a true gem as it offers privacy and an escape from bustling Orlando, yet minutes away from fine dining, top rated schools, parks and boutique shopping. This special home will provide the backdrop for many wonderful family memories to come. Schedule your private tour today and you’ll quickly see just what the epitome of luxury family living in gorgeous Maitland is all about.

1011 N Lake Sybelia Drive, Maitland

350 Northwind Road, Maitland
$2,850,000
5 Beds ⋅ 5 Baths ⋅ Lake Maitland Owl Preserve SubDv. ⋅ 32751 Zip Code
Nestled within the 9-acre Lake Maitland Owl Preserve, this striking contemporary residence—crafted by acclaimed green builder E2 Homes offers a rare blend of architectural distinction, privacy, and natural beauty. Surrounded by protected conservation land, the home delivers a serene retreat just minutes from the vibrant lifestyle of Winter Park. Designed by internationally recognized architect Jose Vengas, the home showcases dramatic ceiling heights, clean modern lines, and expansive glass walls that flood the interiors with natural light while blurring the line between indoor and outdoor living. The thoughtfully designed open-concept floor plan centers around a show-stopping chef’s kitchen featuring custom cabinetry, a statement marble backsplash, and a full suite of premium Sub-Zero and Wolf appliances perfect for both elevated entertaining and everyday living. Living and dining spaces flow effortlessly to a covered outdoor lounge with a fully equipped summer kitchen, overlooking a resort-style pool and spa designed for year-round enjoyment. Whether hosting guests or unwinding in private, this outdoor sanctuary is truly exceptional. All five bedrooms are generously sized private suites, each offering spa-inspired bathrooms with refined finishes and custom detailing. The primary suite is a true retreat, featuring a luxurious bath experience and expansive walk-in closets designed for both beauty and function. A first-floor owner’s suite provides exceptional flexibility for multi-generational living or guest accommodations, while the upper level reveals gallery-style walkways and an elegant terrace that highlights the home’s architectural artistry. With nearly 5,000 square feet of meticulously curated living space, this exceptional estate delivers modern sophistication in one of Central Florida’s most exclusive and private enclaves—just moments from Winter Park’s renowned dining, boutiques, and cultural destinations.

350 Northwind Road, Maitland

640 Old Horatio Avenue, Maitland
$2,850,000
5 Beds ⋅ 4 Baths ⋅ Long Branch Sub SubDv. ⋅ 32751 Zip Code
PRICE IMPROVEMENT!! New Construction with Winter Park Chain of Lakes Access!! You'll be stunned by this gorgeous coastal style home on a private canal that leads to Lake Maitland. This magnificent residence features 5 bedrooms, a bonus room, pool with a relaxing spa and brand new covered boat dock. Your journey begins in the grand two-story foyer featuring elegant lighting choices which are sure to impress. On the left is your study or flex space which can be used as a an additional bedroom as well. As you step into the generous and open grand room to your left is the elegant wine room. The open kitchen is a chef's dream featuring GE Cafe appliances , including a 36" freestanding range as well an Advantium oven and convection wall oven. Elegant slim shaker cabinetry and a large gathering island for entertaining complete this wonderful space. Off the kitchen is a scullery and laundry area with additional dishwasher and refrigerator for preparing grand holiday spreads. The dining room features an additional bar area with beverage refrigeration and overlooks the pool and canal so you can enjoy the views as you share a meal. Summers by the pool will be filled with grilling on the porch as you enjoy the lanai and days on the famed chain of lakes to beat the heat. The primary suite is off the living area and includes a sizable custom closet with everything you could need along with a spa-like bathroom to enjoy a relaxing evening before bed. Upstairs are the additional bedrooms which are generously sized for all of your occupants needs including a large bonus room. There's also a second laundry up to for extra convenience! This wonderful home also included a 12 x 30 Boat dock and sling style lift as well as landscape lighting. Energy savings will be yours with LED Lighting, tankless hot water heaters and spray foam insulation. You also have top rated schools and access to all the shopping, dining and entertainment this wonderful neighborhood offers. This beautiful home is completed and ready to move in- so make an appointment today to view this stunning new home and make it yours.

640 Old Horatio Avenue, Maitland

130 Minnehaha Circle, Maitland
$2,836,000
4 Beds ⋅ 4 Baths ⋅ Minnehaha Shores SubDv. ⋅ 32751 Zip Code
Located directly on the WINTER PARK CHAIN OF LAKES, this house was built in 2007 and COMPLETELY REMODELED in 2014, presenting this stunning contemporary home located ON LAKE MINNEHAHA. Featuring 4 bedrooms, 3.5 bathrooms, a flex room, laundry room, heated pool/spa, summer kitchen, covered boat dock with lift, a grandfathered-in boat house and a 2-car garage for a total of 4,868 sqft! The kitchen is appointed for a chef with THERMADORE INDUCTION RANGE, DOUBLE OVENS, SUB ZERO refrigerator and freezer, WINE CHILLER, THERMADORE dishwasher, an in-drawer microwave and built-in custom cabinets. The kitchen also features a beautiful full-size ISLAND with QUARTZ countertops with space for stools and a breakfast nook perfect for a round table and 8 chairs overlooking the pool. Just off the kitchen resides the laundry room, UPGRADED IN 2019 with built-in cabinetry by Walka Wood Co, an LG washer/dryer and an additional Whirlpool fridge/freezer. The dining room opens to the kitchen with room to hold a dining room table that seats 12 with a custom built-in buffet, cabinetry for storage and custom lighting. The living room located off the dining room, features a FLOOR-TO-CEILING WOOD BURNING FIREPLACE with mirrored DOUBLE MARBLE SLABS and has sliding glass doors opening to the SUMMER KITCHEN and outdoor area. On the opposite side of the kitchen and perfect for entertainment, is a PROFESSIONAL MOVIE THEATER/FAMILY ROOM with floor to ceiling windows and 22 ft high ceilings! The Owner’s Suite is DOWNSTAIRS with beautiful lake views, custom cabinetry, 2 closets and a large master bath. Upstairs there are 3 bedrooms /2 bathrooms and a flex space with beautiful lake views perfect for an office, playroom, or gym. The upstairs gives access to a 1,600 square foot balcony with panoramic lake views that was just RENOVATED IN 2023. Don’t forget the backyard! This is where you will want to spend your time with your family and friends. As you travel to the lake, you pass the heated pool, spa and summer kitchen continuing to the lake you walk through the lush grounds to your sanded beach area and 133+ FEET OF LAKEFRONT on LAKE MINNEHAHA including a grandfathered in 600 SQUARE FOOT BOATHOUSE! There is a COVERED BOAT SLIP, with an automated lift, that will accommodate a Nautique g21 (21 foot+, 5800 lbs.+.) The DOCK WAS RESURFACED IN 2015 with trex composite decking boards, installed with no surface nails. Freshly painted in 2023 - no detail was missed in this exquisite property! Centrally located to Winter Park, Park Ave, I-4 and great shops and restaurants. Call today to see 130 Minnehaha Circle in-person or virtually! <a href='https://www.zillow.com/view-3d-home/94654f0a-5608-47e8-9e61-e1fec6bd93fd?setAttribution=mls&wl=true&utm_source=dashboard'>https://www.zillow.com/view-3d-home/94654f0a-5608-47e8-9e61-e1fec6bd93fd?setAttribution=mls&wl=true&utm_source=dashboard</a>

130 Minnehaha Circle, Maitland

216 N Lake Sybelia Drive, Maitland
$2,770,000
5 Beds ⋅ 6 Baths ⋅ Poors Add SubDv. ⋅ 32751 Zip Code
Exquisite Lakeview pool home, built in 2021, combines modern elegance and timeless style. Located in the heart of Maitland, with front-row seats to unforgettable sunsets over Lake Sybelia! This Five bedroom, Five and a half bath residence boasts 4,697 square feet of tastefully designed living space. Inside you’re met by a grand foyer and airy layout flooded with natural light, soaring ceilings, wide-plank hardwood floors, custom window treatments, and designer finishes throughout. The gourmet kitchen is an entertainer's delight-equipped with top-of-the-line Wolf and Sub-zero appliances, Taj Mahal quartzite, stunning 12-foot waterfall island, 48” 8 burner gas range with pot filler, large walk-in pantry, with butler’s pantry adjoining the kitchen and dining— the open concept design is perfect for both entertaining and every day living. The living room’s quartz-accented fireplace and sleek glass folding doors provide a seamless flow between indoor and outdoor living. Retreat to the primary suite's spa-inspired bathroom with custom designed walk-in closet, dual vanities, soaking tub and double walk-through shower. A sleek cable railing staircase leads to four generously sized Bedrooms-three with ensuite baths, four bathrooms, a designated Office and versatile Loft/Flex space. Enjoy breathtaking lake views whether working or unwinding! Equally impressive is the beautifully landscaped outdoor living space, with expansive covered lanai, multiple lounge areas, fully equipped summer kitchen, gas fire pit and luxurious salt-water pool and spa. Property features smart home technology, custom closets systems, remote controlled window treatments, surround sound, full-house generator, 500 lb propane tank, 3 car garage with epoxy flooring and so much more! A short walk to Lake Lily and the Maitland Farmers Market, and minutes to Winter Park and I-4. This exceptional home combines refined luxury with an unbeatable location. Don’t miss out on this rare find!

216 N Lake Sybelia Drive, Maitland

591 Dommerich Drive, Maitland
$2,650,000
5 Beds ⋅ 5 Baths ⋅ Dommerich Estates 2nd Add SubDv. ⋅ 32751 Zip Code
Stunning waterfront residence on Lake Minnehaha, part of the celebrated Winter Park Chain of Lakes! This spacious 5-bedroom, 4.5-bath home is designed for luxurious lakefront living and effortless entertaining. The gourmet kitchen is a chef’s dream, featuring a Thermador 6-burner gas range, GE Monogram side-by-side refrigerator and freezer, Bosch dishwasher, wine refrigerator, and a separate prep area with additional GE oven and dishwasher. The expansive first-floor primary suite offers lake views, a spa-style bath with custom cabinetry, an oversized shower, and a dedicated shoe closet. An additional first-floor bedroom with a private ensuite bath is ideal for guests or in-laws. Upstairs, you’ll find three additional bedrooms, two full baths, and a private office with serene views. Enjoy Florida living year-round with a resort-style outdoor space that includes a covered lanai, sparkling pool and spa, fire pit, and a covered boat dock. Bring your ski boat and jet skis — your backyard is a waterfront playground. Plantation shutters throughout add a classic touch to the interior. Zoned for top-rated Dommerich Elementary, Maitland Middle, and Winter Park High. Rare opportunity to live on the water in one of Central Florida’s most sought-after communities!

591 Dommerich Drive, Maitland

656 Bentley Lane, Maitland
$2,650,000
6 Beds ⋅ 7 Baths ⋅ Maitland Forest SubDv. ⋅ 32751 Zip Code
Pre-Construction. To be built. Stunning modern estate perfectly positioned along the shores of the Winter Park Chain of Lakes. This architectural masterpiece, designed and built by Vimaro Homes is sure to be a showstopper. As you pull up the elegant circular driveway you’re greeted by lush landscaping, and an oversized three car garage. Stepping though the front doors, your eyes are immediately drawn to the bright open floor plan and exquisite architectural details. From the custom three-story staircase to the double sided fireplace and wall of windows overlooking the lake this is truly a bespoke property. The chef in the family will love the open kitchen with its top-of-the-line appliances, custom cabinetry, porcelain counter tops, oversized pantry, and massive center island overlooking the great room. The primary bedroom suite features a bird’s eye view of the lake, an exquisite bathroom that will rival even the most prominent spas, and a huge walk-in closet to house even the largest show collection. Additional features include a home office, two laundry rooms, a guest suite on the first floor, 4 additional bedrooms on the second floor, and a game room with a powder bath on the lower level. For entertaining, simply lower the retractable screens on the covered lanai and open the entire back of the home bringing the outdoors in. Exterior amenities include a summer kitchen, oversized outdoor patio with glass railings, and an amazing pool with a double-sided infinity edge. Last but not least, there is an impressive staircase leading down to the back yard and your own private boat dock. The massive peninsula lot steals the show with one-of-a-kind lake views and plenty of room for a detached guest house or additional garages for the car enthusiast. Don’t miss this opportunity to enjoy living on the Winter Park Chain of lakes for a fraction of typical the cost.

656 Bentley Lane, Maitland

928 Versailles Circle, Maitland
$2,550,000
6 Beds ⋅ 6 Baths ⋅ Versailles SubDv. ⋅ 32751 Zip Code
Exquisite Estate on Lake Minnehaha! This stunning residence features over 5,000 square feet of living space and is perfectly positioned along the shores of Lake Minnehaha on the famed Winter Park Chain of Lakes. This 6 bedroom, 5 full bath plus 1 half-bath home offers the perfect setting for relaxation and enjoying the sunshine. As you enter, you are greeted by the grand staircase and the soaring two-story ceilings. Off the foyer, there is a den/office, half bath for guests, and a large dining room to host all the holiday gatherings. The main living areas and the owner's retreat offer breathtaking views of the lake from the oversize lot, providing added privacy. The home is beautifully appointed with a spacious kitchen featuring stainless steel appliances, granite countertops, large island, a vegetable sink, and a walk-in pantry. The kitchen overlooks the family room which includes a tranquil gas fireplace. The open floor plan, with vaulted ceilings, includes wood floors downstairs and wood flooring throughout most of the home. The master bedroom, located on the 1st floor, overlooks pool and lake to watch the sunrises. There are 4 bedrooms upstairs with 2 Jack & Jill bathrooms. Additionally upstairs, there is a loft area and a bonus/play room. Ample storage and closets throughout the house. 3-car oversized garage with ample space for a workbench and toy storage. The property features a lovely pool, spa and a dock, where you can soak in the beautiful views. Cook meals in the summer kitchen and enjoy breakfast the lanai watching the most amazing sunrises. With over 170 feet of shoreline and a private boat dock with a boat lift, there is sure to be endless hours of fun on the water. Circle driveway and ample onsite parking. Note* APROX. 1 acre of dry land.

928 Versailles Circle, Maitland

705 N Lake Sybelia Drive, Maitland
$2,535,000
5 Beds ⋅ 4 Baths ⋅ Sybelia Shores Second Add SubDv. ⋅ 32751 Zip Code
Completed New Construction 2024 | Lakefront Luxury | Below Appraised Value: This extraordinary custom lakefront residence was built by Dave Konkol & is elevated on a 0.56-acre corner lot w/ approximately 112’ of lake frontage. Featuring a crisp stucco exterior, impact windows & remote-operated screened porches, the home is surrounded by professionally designed native landscaping & butterfly gardens which set the stage for a lifestyle defined by natural beauty, enduring materials, timeless design & everyday comfort. Once inside, the open floor plan showcases wide-plank, white oak engineered wood flooring & is filled w/ natural light from the large format windows that frame views of the backyard pool & serene Lake Sybelia out front. A formal dining space connects to a wet bar & opens to a functional yet casually elegant kitchen. Quartz countertops, custom soft-close cabinetry with pull-outs & a full suite of premium appliances lend functionality & refinement to the kitchen. A large walk-in pantry & adjacent drop zone add quality of life to the beautifully tailored design. The main-level primary suite is a sanctuary w/ lake views, remote-controlled blackout shades, decorative wood ceiling beams, a customized walk-in closet & a spa-like bathroom featuring Frank Lloyd Wright Brizo plumbing fixtures, a long vanity stained to match the fixtures, dual sinks, an oversized glass-enclosed shower with 21” rainhead, soaking tub & private water closet. A guest bedroom w/ adjacent full bath also functions as a pool and powder bath. The large laundry room w/ quartz countertops, GE Profile front-loading washer and dryer & a Laundry Jet Swift pneumatic laundry chute—connected to the primary suite & upstairs bedrooms and complete the main floor. Upstairs, two additional bedrooms with wide water views include customized closets & designer baths. The cozy loft and Bonus spaces flex easily for work, wellness, or play. Other interior features include built-in speakers, custom millwork, motorized blinds & smart-home wiring to enhance comfort and livability. Seamless indoor-outdoor transitions define the rear living experience, where a deep covered lanai includes recessed lighting, fans, speakers & motorized screens opening to a 7’ deep, heated, saltwater pool w/ sunshelf, outdoor shower & direct access to a full bathroom. The fenced backyard offers ample space for play, relaxation & a dog run. A custom dock w/ composite decking & covered boat lift sits on Lake Sybelia—offering year-round opportunities for boating, paddle-boarding, swimming & fishing on waters with no public access. Efficiency abounds thanks to a PES Solar system featuring 58 REC panels, four Enphase battery backups & real-time energy monitoring. Additional features include Trane HVAC systems, a commercial-grade water heater w/ recirculating pump & a new irrigation system w/ pump fed by lake water. The three-car garage includes modern paneled doors w/ openers and extra storage. Now unexpectedly available due to a change in the owners’ plans, this is a rare opportunity to purchase an almost-new custom home—combining advanced systems with timeless design—in one of Maitland’s most beloved neighborhoods, just minutes from Lake Lily Park, downtown Maitland, major thoroughfares and Winter Park’s shops and restaurants.

705 N Lake Sybelia Drive, Maitland

604 Minnehaha Lane, Maitland
$2,475,000
6 Beds ⋅ 6 Baths ⋅ Packwoods Plan/Maitland SubDv. ⋅ 32751 Zip Code
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 and airy—sunlight does the work here. A direct foyer sightline leads you to a rear wall of French doors that draw in a calm, even glow of natural light across heart-of-pine floors and disciplined millwork: raised-panel wainscot, multi-step crown molding, and architectural beams. Those doors open to a full-length covered lanai; beyond, a heated saltwater pool and spa step down to a deep backyard and a private dock with a covered boat slip and adjoining lounge deck. The kitchen is built to perform so life feels easy. Morning coffee, weeknight pasta, Saturday crowds, it handles all of it. Sub-Zero refrigeration with additional refrigerator drawers, a Thermador six-burner gas range, two dishwashers, and a warming drawer. Granite counters surround a prep island with rinse sink; the peninsula takes the laptops and late plates. A dry bar with wine cooler ties to the dining room for effortless pours and keeps glassware close at hand. Just off the family room, the primary suite claims a quiet corner and opens to the lanai; coffee at sunrise, warm light at day’s end. A large custom walk-in closet answers storage; the bath finishes the suite with tumbled marble, Kohler fixtures, and a cast-iron vintage tub. At the center of the first floor, a deliberate service run keeps daily life organized: powder bath, temperature-controlled wine cellar, a straight sightline to the first of two laundry rooms and the garage entry ending at a private interior stair to a secluded in-law/guest suite with its own full bath. It’s independent, quiet, and ideal for long stays or live-in support. The main stair brings you to a second level arranged with intent. One wing holds three bedrooms around a shared bath. An office corridor carries you to the lake-view great room under a coffered ceiling; triple French doors open to the full-length upper veranda. Another bedroom on this wing enjoys its own veranda access with a full bath close by. Above it all, the third floor is a generous, flexible loft fit for a screening room, billiards or game lounge, studio, gym, or a collector’s library with practical storage tucked to the edges. Quiet systems match the craft: Cat-5 wiring, surround sound, central vacuum, and two laundry rooms. Recent updates keep the essentials current: new HVACs (2020, 2021) and a new dock (2024). Zoned for Maitland Middle and Winter Park High, this home is tuned to everyday rhythm: water out back, light throughout, spaces that work the way you live. From lanai shade to the last light on the lake, it delivers on its promise—an honest, crafted place where the architecture serves the life it keeps.

604 Minnehaha Lane, Maitland

1321 Magnolia Bay Court, Maitland
$2,350,000
5 Beds ⋅ 4 Baths ⋅ Magnolia Bay SubDv. ⋅ 32751 Zip Code
Welcome to your dream home nestled in the sought-after prestigious gated community in a Winter Park/Maitland blended neighborhood with deeded boat slips on Lake Maitland, providing boating access to the six-lake Chain of Lakes! This exquisite, one-owner, custom-built true five-bedroom traditional Charleston-style residence, built in 2001, boasts unparalleled elegance and pride of ownership. Lovingly cared for by one family over the years, the home offers a rare opportunity to purchase in this unique gated community with only eight residences. As you step through the front door, you'll be greeted by the charm of the formal library and dining rooms, creating a perfect setting for entertaining guests. There are numerous amenities beyond the gated entrance, including a walkway to Lake Maitland, individual boat slips, and an oversized community lawn that creates a park-like setting to enjoy by the lake. The main gathering room, sunroom, and bonus room offer versatile spaces for relaxation and recreation, while the dedicated fitness room caters to your active lifestyle. The first-floor primary suite is a true retreat, featuring views of the 45 by 10-foot lap pool and a meticulously landscaped backyard. The spacious island kitchen with a breakfast area provides a welcoming space for culinary creations, with easy access to a covered outdoor living area for al fresco dining. Step outside and discover your own private oasis – an outdoor cabana complete with a fireplace and TV, perfect for outdoor entertaining with a lushly landscaped perimeter. Roof was replaced in 2022. Both air conditioning units were replaced in 2015, newer appliances. This residence offers tranquility and exclusivity that is rare to find. Embrace the great outdoors and create lasting memories by the water. Beyond the gated community, this home is ideally situated for convenience to local area restaurants, Park Maitland School, and the famed Enzian Theatre. A short bike ride takes you to the renowned Winter Park's Park Avenue, offering upscale shopping, dining, and cultural experiences. With top-notch schools and easy access to major roadways, this location seamlessly combines luxury living with practicality. Don't miss the chance to make this exquisite property your own – where elegance meets comfort, and every day feels like a vacation. Room Feature: Linen Closet In Bath (Primary Bedroom).

1321 Magnolia Bay Court, Maitland

734 Terra Place, Maitland
$2,250,000
6 Beds ⋅ 8 Baths ⋅ Terra Place SubDv. ⋅ 32751 Zip Code
Presenting a stunning new construction residence located on a quiet cul-de-sac offering a seamless blend of luxury, functionality and modern design. The main home features four spacious bedroom suites, a dedicated office and a bonus/flex area, 4 full baths and 2 half baths, while the property also includes a rare-to-find one-level detached 1,143 sf 2BE/2BA guest house that includes a kitchen and a living area... *** ideal for for multi-generational living, spacious home office, live-ins or long term guests… Beautiful wood floors extend throughout the main house living spaces, complemented by designer porcelain tile in all baths. The open floor plan showcases soaring 21-foot ceilings in the great room and dining area, anchored by a beautiful chef’s kitchen complete with a dual-fuel range, quartz waterfall island, custom blended cabinetry and an adjacent walk-in pantry. A wall of sliding glass doors in the great room opens to the expansive covered lanai and new Pebble Tec pool with autofill and auto-drain features, all surrounded by travertine decking and a masonry and aluminum privacy fence. The first-floor primary suite offers a serene retreat with private pool courtyard views, a custom walk-in closet and a spa-inspired bath with marble floors, a spacious walk-in shower and a separate soaking tub. Upstairs, there are three additional bedroom suites and a versatile loft to provide ideal space for relaxation lounge area. The side-entry two-car garage includes epoxy floors, EV charging readiness and direct access to the mudroom, laundry, pantry and kitchen for everyday convenience. Designed for year-round entertainment, the covered lanai is stubbed and ready for a summer kitchen, with additional outdoor space available for expanded amenities. Both main and guest houses are bathed in natural light thanks to generous architecturally enhancing windows and glass doors. Modern comforts include smart lighting, exterior security cameras and a built-in audio system. On a quiet cul-de-sac, this property is within visiting or biking distance to Maitland Community Park, a 25-acre wooded park with tennis courts, basketball, playgrounds, trails and pavilions! Enjoy easy access to other downtown Maitland amenities, 7-10 minute drive to Park Avenue in downtown Winter Park, quick access to major roadways & I-4, downtown Orlando, area hospitals, and both executive and international airports... Zoned for regarded Lake Sybelia Elementary, Maitland Middle and Winter Park High School, this exceptional home is a rare offering in a secluded, wonderful neighborhood.

734 Terra Place, Maitland

180 Shell Point W, Maitland
$2,200,000
5 Beds ⋅ 4 Baths ⋅ Maitland Isle SubDv. ⋅ 32751 Zip Code
One or more photo(s) has been virtually staged. Nestled on a meticulously landscaped canal-front property with direct access to Lake Maitland and the Winter Park Chain of lakes, this renovated five-bedroom, four-bath home by Parkland Homes offers a perfect blend of sophistication and comfort. Boasting a thoughtful design with many recent updates, this residence presents a warm and inviting ambiance, complete with private boat house. The open and expansive living spaces create an ideal setting for seamless entertaining, with a chef-inspired open kitchen serving as the heart of the home. Revel in culinary delights with updated cabinets, stainless steel appliances, gas range, warming drawer, granite countertops, and reverse osmosis. The adjacent dining area sets the stage for both formal and informal gatherings, while a new gas fireplace with added mantel in the family room provides a tranquil retreat. The newly painted stairway and railings lead to a spacious and versatile game room complete with bar that opens up a world of possibilities. Step outside onto the new open deck for stunning views of the backyard, pool area, and waterfront. Two bedroom suites grace the first floor, including a main primary suite with generous walk-in closet and luxurious master bath featuring a large soaking tub, separate shower, and dual vanities with granite countertops. Another first-floor suite caters to in-law accommodations or visiting guests. The second floor hosts three bedrooms and two full baths, one of which is en-suite. Your outdoor entertaining begins as you step out onto a breathtaking 600-square foot lanai through pocket sliding doors. This private oasis features retractable screens, a saltwater pool, heated spa (2018), and ample space for hosting family and friends. The meticulously landscaped backyard provides a serene setting, complemented by mature landscaping, lower firepit area, and lush artificial turf. This home boasts a plethora of updated features including: fresh exterior paint, new front door, landscaping, landscape lighting, wood plantation shutters, custom built-ins, closet storage systems, and two new Trane 4-ton 19.5 seer units (2020) air conditioners, and new roof (2021). The 2016/17 remodel saw the entire house replumbed, upgraded flooring, replacement of door hardware, and additional canned lights. All baths underwent a complete overhaul with new showers, tubs, sinks, fixtures, and granite countertops. Electrical outlets and switches were upgraded, and three custom built-ins were incorporated. Outdoor enhancements include a new cement driveway, revamped pool area with new heater, plaster, coping, and pavers, conversion to a saltwater pool with a continuous monitoring system, and the addition of a child safety fence in 2019. The side yard was fenced, and a carport was added to the driveway. The newly improved boat house boasts new siding, painted and sealed roof, lift hardware, new straps, and the lift motor was replaced in 2020. With access to Lake Maitland and the Winter Park Chain of Lakes, this residence offers an exceptional waterfront lifestyle in a very sought after neighborhood. Zoned for A-rated Maitland Middle School and Winter Park High School, this home exemplifies the epitome of luxury living.

180 Shell Point W, Maitland

641 Lake Catherine Drive, Maitland
$2,150,000
5 Beds ⋅ 6 Baths ⋅ Sheridan Place SubDv. ⋅ 32751 Zip Code
This stunning contemporary lakefront residence, completed in 2019, offers almost 6,000 square feet of refined living space with magnificent elevated views of Lake Catherine. Thoughtfully designed with elegant finishes, this two-story, five-bedroom, 5.5-bath residence, plus office/media room and open flex/lounge area that showcases a bright/open floor plan enjoying expansive walls of glass windows/doors that frame the serene waterfront setting. The main level features sleek porcelain tile flooring, soaring ceilings, and sun-drenched interiors. Two separate back-to-back fireplaces connect the formal dining area and living room, while the spacious family room is bathed in natural light. The modern kitchen boasts a large island, high-end appliances, a hidden pantry and laundry room, and a built-in coffee maker. The first-floor primary suite offers lake views, a custom walk-in closet and a spa-like bath with dual sinks, a walk-in shower and a jetted soaking tub. A versatile flex space adjacent to the suite is ideal for a fitness area, office or private retreat. A floating staircase leads to the second level, where a generous bonus room/game room, two additional bedroom suites with walk-in closets and en-suite baths, and another flex room await. The expansive second-floor balcony overlooks the sleek glass-railed pool and provides uninterrupted lake views. A separate parcel across the street includes a private covered dock on the 21-acre Lake Catherine, ideal for kayaking and paddleboarding. The two-car garage, accessed through a gated rear entry, adds convenience and security. In a tranquil, private setting, yet minutes from Maitland’s cultural corridor as well as the vibrant shopping and dining of Park Avenue, this exceptional property seamlessly blends contemporary luxury with lakeside tranquility.

641 Lake Catherine Drive, Maitland

451 Northwind Road, Maitland
$2,150,000
3 Beds ⋅ 3 Baths ⋅ Lake Maitland Point X/8 Lot 1 SubDv. ⋅ 32751 Zip Code
Discover a once-in-a-lifetime chance to own nearly a half acre of prime lakefront property on Lake Maitland, the largest of the Winter Park Chain of Lakes. Nestled in a serene alcove, this secluded setting is surrounded by multimillion-dollar homes and new custom construction, offering endless possibilities for creating your dream estate. The value of this property lies in the land, making it the perfect canvas for designing the ultimate lakefront retreat. Renovate the existing home or start fresh to craft a residence that meets your every desire. A covered boat dock with lift ensures easy access to the Chain of Lakes, where you can enjoy boating, waterskiing, wakeboarding, paddleboarding, and fishing. The property also features a lakeside pool with spa and a concrete seawall to protect and enhance your waterfront experience. This tranquil neighborhood is graced with towering oak trees and winding roads that create a picturesque setting. Located just minutes from downtown Winter Park, you’ll enjoy fine dining, boutique shopping, and cultural experiences along Park Avenue. The property is zoned for top-rated public schools and conveniently close to everyday necessities. Lake Maitland is not just a home — it’s a lifestyle. A short boat ride takes you to the Winter Park Racquet Club, a premier destination for dining and social events. Don’t miss this extraordinary opportunity to embrace the luxury and leisure of lakefront living on the prestigious Winter Park Chain of Lakes.

451 Northwind Road, Maitland

771 Dommerich Drive, Maitland
$2,150,000
4 Beds ⋅ 4 Baths ⋅ Oaks Of Maitland SubDv. ⋅ 32751 Zip Code
Presenting a magnificent lakefront retreat boasting timeless elegance, captivating sunset views, and glorious water vistas, perched along the pristine shores of Lake Minnehaha and the Winter Park Chain of Lakes. This classic home is a showplace of lakefront living with open water views from almost every room. Tucked within The Oaks section of Dommerich Estates, where peaceful mornings and tranquil nights offer a haven from the hustle and bustle, this grand home exudes style and class. Enter through a rich mahogany door to a foyer with beautiful rich wood flooring. The eye is instantly drawn to the picturesque windows lining the Great Room-style Living Room with cathedral ceilings and an expansive Florida room beyond, bathed in sunshine and showcasing sweeping lake views. A sparkling lap pool is perfectly suited to provide a refreshing break. The chef’s kitchen with center island cooktop, breakfast nook, custom cabinetry, beverage cooler, and stainless appliances is generous in size and serves as a gathering place for all. A wood-paneled Family Room is easily accessible and offers a cozy escape. On the opposite side of the house on the first floor sits the primary bedroom and den lined with bookshelves. The master suite features sliding glass doors, a large walk-in closet, double vanities, garden tub, and separate shower. Upstairs are three additional bedrooms including one ensuite and two bedrooms with lakefront balconies. A boathouse with pier stands ready to host watersport toys of all kinds. The cleared lakefront provides direct sandy beach access to the lake. Neighborhood features boardwalk access to Maitland Community Park with a playground and tennis courts. Zoned for highly sought-after Dommerich Elementary, Maitland Middle, and Winter Park High. Come experience living on the Winter Park Chain of Lakes from one of the most desirable locations in Central Florida.

771 Dommerich Drive, Maitland

103 Whitecaps Circle, Maitland
$2,000,000
5 Beds ⋅ 5 Baths ⋅ Hollieanna Shores 1st Add SubDv. ⋅ 32751 Zip Code
Under Construction. A striking blend of refined luxury and sleek contemporary architecture, this exceptional new construction residence is set to be completed in July 2026. Designed for effortless living and elevated entertaining, the home showcases 5 well-proportioned bedrooms, 4.5 designer bathrooms, and approximately 3,695 square feet of thoughtfully curated interiors. From the moment you enter, you’ll experience a bright, open layout that flows seamlessly from one space to the next. At the heart of the home is a culinary-inspired kitchen, complete with premium appliances, custom cabinetry, quartz surfaces, and a generous island that invites gathering and conversation. The living and dining areas are ideal for hosting, framed by expansive windows that capture views of the outdoor retreat. The private primary suite feels like a personal spa, featuring a serene bath with dual vanities, a freestanding soaking tub, a walk-in shower, and a spacious wardrobe closet. Each additional bedroom offers comfort, style, and ample storage—perfect for family, guests, or a dedicated office. Outside, the property transforms into an outdoor sanctuary with a shimmering pool, a covered lanai designed for year-round enjoyment, and a fully equipped summer kitchen ready for unforgettable weekends. A rare opportunity to own a remarkable residence where modern design meets everyday livability—a home you’ll never want to leave.

103 Whitecaps Circle, Maitland

190 Shell Point W, Maitland
$2,000,000
5 Beds ⋅ 3 Baths ⋅ Maitland Isle SubDv. ⋅ 32751 Zip Code
Perfectly placed on a meticulously manicured Lake Maitland canal-front lot, this five-bedroom, three-bath home offers 3,881 square feet of living area with a total of 5,157 square footage located in Maitland Isle community. Warm, welcoming and adorned with fine modern finishes, the open and light-filled living spaces ensure effortless entertaining. A chef-inspired kitchen with stainless steel appliances, gas range, warming drawer, wood cabinets, large pantry and granite countertops will ignite countless culinary creations, while an adjacent dining area facilitates intimate gatherings. A cozy gas fireplace in the living area provides a quiet and comfortable haven. There are four bedrooms located on the first floor with two full baths, one of which is an en suite and the other a Jack and Jill. The large main suite is on the second floor offering views of Lake Maitland, two walk-in closets and is accompanied by a lavish master bath that includes a large soaking tub, ample separate shower and dual vanities with granite countertops. Serenity abounds in the home’s private outdoor space when you open to this 50 ft canal front home that includes a saltwater pool, heated spa (2018), new pavers (2018), coping (2018), outdoor shower and plenty of room to host family and friends. The backyard is an oasis with a private setting, and the yard is beautifully landscaped with mature landscaping and zoysia grass. This home offers endless updated features. The appointments include wood plantation shutters, custom built-ins throughout, closet storage systems, water heater (2019), A/C System (2017) with humidity control, gas dryer, gas water heater, repainted inside, rebuilt in 2000. Outside, this home offers a beautiful brick drive with a 3 car garage and additional boat storage. The home offers a beautiful boathouse, with lift and a large wood deck for fishing, as well as experiencing peace and relaxation with the serene canal. With access to Lake Maitland and the Winter Park Chain of Lakes, this exquisite residence presents an exceptional waterfront lifestyle. Zoned for A-rated and highly sought-after Maitland Middle School and Winter Park High School. Discover the epitome of waterfront luxury living in Maitland Isle. Embrace the Florida dream lifestyle, perfectly balancing luxury, convenience, and natural beauty. Schedule a viewing today and explore the endless possibilities that await you in this extraordinary property.

190 Shell Point W, Maitland

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