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$3,894,945
6 Beds ⋅ 7 Baths ⋅ Briley Farm - Phase 1b SubDv. ⋅ 34787 Zip Code
Pre-Construction. To be built. Briley Farm rests comfortably on 111 acres of lush landscape in the beautiful town of Oakland, Florida. The property is a seamless blend of charming Old Florida and modern-day luxury living, designed to provide the ultimate retreat for you, your family, and friends. Welcome to a world of luxury, craftsmanship, and design excellence! Each residence will be meticulously designed to complement its natural surroundings, with spacious floor plans that flow from room to room, planned to be airy yet cozy and ready for your personal touch. At Briley Farm, you'll find a seamless combination of residential luxury and convenience, with homes built for enjoying the best of indoor and outdoor living. Briley Farm boasts serene scenery as a picturesque back drop for new home construction, while still near shopping, restaurants, and major highways. At Briley Farm you'll discover comfortable countryside living under a canopy of welcoming trees, set to embody the lifestyle for which you've been searching, all nestled away from life's demands.

517 N Pollard Street, Oakland
$1,225,000
5 Beds ⋅ 7 Baths ⋅ Canopy Oaks Ph 1 SubDv. ⋅ 34787 Zip Code
Within the gated community of Canopy Oaks in Winter Garden, Parade of Homes award-winning Delray model by renowned builder A.R. Bailey Homes combines timeless architecture with curated upgrades rarely found in today’s market. Within an intimate enclave of only 49 homesites, this meticulously maintained home offers over 4,000 square feet of flexible multigenerational living, entertaining spaces and seamless indoor-outdoor Florida living. Ideally just minutes from Historic Downtown Winter Garden, Winter Garden Village, Orlando Health, the Roper YMCA, shopping, dining, recreation and major roadways including Florida’s Turnpike, SR 429, SR 408 and Interstate 4. A paver driveway, concrete tile roof, stone-accented exterior, wood-look garage doors, three-car garage and grand solid wood double-entry doors create a striking first impression. Inside, 10-foot ceilings in the great room, architectural details, abundant natural light, elegant finishes, and wood-look porcelain tile flooring throughout the first floor create a sophisticated yet welcoming atmosphere. The chef’s kitchen serves as the heart of the home, designed for everyday living and entertaining. Highlights include a natural gas cooktop with exterior vent, built-in wall oven, upgraded appliances, pot filler, oversized center island, 42-inch cabinetry with crown molding, under-cabinet lighting, designer tile backsplash and an expansive walk-in pantry overlooking the coffered-ceiling great room. A gated wine cellar adds a distinctive feature rarely found at this price point. The luxurious first-floor primary suite was designed as a spa-inspired retreat, featuring a beautifully appointed primary bath with premium finishes, dual vanities, an oversized walk-in shower, freestanding soaking tub and a spacious walk-in closet. A separate first-floor en-suite bedroom provides flexibility for guests, extended family, multigenerational living or a private home office. Upstairs, a second primary suite is complemented by two additional en-suite bedrooms, a spacious loft, guest powder bath and covered balcony, providing privacy and versatility for family and guests. Designed to embrace Florida’s indoor-outdoor lifestyle, dramatic corner-opening glass doors and expansive stacking sliders open to the covered lanai with a motorized retractable screen, creating effortless entertaining year-round. The backyard, accented by a stucco privacy wall, offers ample space for a custom pool, outdoor kitchen and additional outdoor living areas. The three-car garage provides generous space for vehicles, golf carts, storage and recreational equipment. Additional highlights include dual tankless water heaters, dual HVAC systems with zoned climate control, motorized roller shades, decorative iron stair railings, mudroom, reading nook and generous storage throughout. Residents of Canopy Oaks enjoy scenic recreational trails, a community playground and an exceptional Winter Garden location near shopping, dining, healthcare, recreation and everyday conveniences. Offering five en-suite bedrooms, seven baths, dual primary suites, a spa-inspired first-floor primary suite, wood-look porcelain tile throughout the first floor, a three-car garage, natural gas, award-winning design and an exceptional location within Canopy Oaks, this beautifully maintained residence presents an outstanding opportunity to experience refined Winter Garden living. Also available for lease (MLS #O6416527).

706 Canopy Estates Drive, Winter Garden
$1,499,999
5 Beds ⋅ 7 Baths ⋅ Canopy Oaks Ph I SubDv. ⋅ 34787 Zip Code
BOM. Buyer decided against stairs. There is a specific kind of silence that exists only within the gated sanctuary of Canopy Oaks. It is the sound of ancient oak leaves stirring in a gentle breeze & the distant, rhythmic splash of a stone fountain. Here, the recipient of the Parade of Homes Grand Award stands as a magnificent testament to what happens when timeless Italian architecture is reimagined for a modern lifestyle. This is not merely a residence. It is a legacy of vertical liberation, a home that breathes with you, scales with your ambitions, and cradles your quietest moments in an embrace of stone and iron. Your journey begins at the threshold of 8-foot, solid double-entry doors. As they swing open, the frantic pace of Central Florida fades, replaced by a two-story foyer that commands immediate respect. A hand forged iron staircase sweeps upward in a graceful arc, mirrored by the delicate charm of a Juliette balcony that suggests a life lived with a touch of Mediterranean flair. Every inch of this grand entrance is a curated experience, designed to transition you into a realm of meticulously crafted prestige where every shadow and light well has been considered. For those who view cooking as a performance art, the professional-grade kitchen is your stage. High-end Kitchen Aid appliances and a natural gas cooktop meet the warmth of artisanal design. The 42-inch upper cabinetry and a hidden walk-in pantry ensure the visual continuity remains unbroken. At the center sits a massive prep island with integrated beverage refrigeration, designed specifically for the art of hosting. Here, the boundary between chef & guest is delightfully blurred. Nearby, the home reveals its most enchanting secret, the drop-down wine cellar. Behind a hand-forged iron gate lies a space that transports you directly to a cobblestone alleyway in Tuscany. With label-forward shelving casting a museum-quality glow & a quaint bistro table within, it evokes the feeling of a private corner in a centuries-old Italian eatery. It is the ultimate setting for an evening pour, a space where time slows down & the modern world feels a thousand miles away. The first-floor owner’s suite is a masterclass in personal seclusion. By design, this space serves as a dedicated haven of quietude, featuring soaring tray ceilings & an atmosphere of total stillness. The spa-inspired bath, featuring a frameless glass walk-through shower & a free-standing soaking tub, offers a daily ritual of total restoration. As you ascend, the lifestyle shifts toward entertainment. The dedicated theater room stands ready for premiere nights, offering a dark, immersive escape. Adjacent, the versatile gathering room opens onto a private balcony overlooking the shimmering resort-style pool & the vast, permanent conservation area. With no rear neighbors, your view is an unbroken tapestry of natural beauty. The outdoor living area features a resort-style pool & spa framed by water/fire bowls & a rainfall pergola. With a full summer kitchen & a backyard that merges into conservation, your privacy is absolute. Enjoy the nightly glow of nearby fireworks from your peaceful terrace, surrounded by the scent of night-blooming jasmine. Strategically along the medical corridor, you are minutes from AdventHealth, Orlando Health & the soul of Winter Garden. Backed by a whole-house natural gas generator & water purification, this home offers security & beauty. Welcome home. Check out the video tour!

743 Canopy Estates Drive, Winter Garden
$2,775,000
5 Beds ⋅ 6 Baths ⋅ Signature Lakes, Independence SubDv. ⋅ 34787 Zip Code
One or more photo(s) has been virtually staged. Independence ** Rare 1.39-acre LAKEFRONT cul-de-sac pie-shaped lot with 300 feet of Lake Hancock frontage ** Truly exceptional outdoor living with a heated resort-style pool and spa, LED lighting, swim-out bar, outdoor kitchen, and incredible views of Disney fireworks ** 320sf trex dock extends to a covered boathouse with water, electric, boat lift and double jet ski lift ** Stunning 2019 custom home by Sorenson Construction offers exceptional craftsmanship and breathtaking lake views and Disney firework views ** Interior highlights include 30’ soaring atrium ceilings with wood beams and Velux skylights, a striking double-sided precast travertine fireplace, wood flooring in main living areas, solid wood cabinetry, 9’ solid wood doors, crown molding, and custom closet systems throughout ** The French Provincial chef’s kitchen features stone countertops, farmhouse sink, expansive mahogany island with gas cooktop, Monogram Advantium appliances, and a light-filled breakfast area overlooking the lake. The family room showcases tongue-and-groove beam ceiling, built-ins, and triple sliding glass doors opening to the outdoor living space ** Entertainment spaces include a tiered theatre/media room with screen, speakers and equipment included, plus a game room with lake views and access to the 3-tier patio. A first-floor guest/in-law suite with private entrance provides added flexibility ** Upstairs, the primary suite offers a tray ceiling, Juliet balcony with retractable screen, and spectacular lake views, along with a luxurious bath featuring a round soaking tub, glass shower with designer tile, and custom walk-in closet. A second-floor library/office with French doors and shared wet bar connects to the primary suite. Additional features include Anderson windows, 4.5-car garage with epoxy floors and custom storage, EV charger, whole-home water softeners, reverse osmosis, HVAC UV light and dehumidifier ** Located in the sought-after Independence community with low HOA fees including cable and internet, plus community pools, parks, playgrounds, 2 clubhouses, community events, 10' biking/walk path and +/-2 miles from the 429 entrance and great newer stores, restaurants and businesses ** Buyer to verify square footage-All rm measuremts approx from Builders flr plan. All of these convey - Bookcases in den/library, TV on back patio, TV in great rm, murphy bed 1st flr bdrm, pool table, refrig in garage, wine refrig, media equipment.

6621 Point Hancock Drive, Winter Garden
$1,320,000
4 Beds ⋅ 5 Baths ⋅ Canopy Oaks Ph 1 SubDv. ⋅ 34787 Zip Code
One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Enter a home that feels like a quiet triumph. Every curve, every beam, every room of this award-winning Sanibel model defines timeless luxury and refined design. Known as The Castle, this French Country–inspired masterpiece earned Best Model Home in Florida and the Parade of Homes Grand Award, captivating those who appreciate fine architecture and superior craftsmanship. Step through arched double metal doors into a bright, elegant foyer that unfolds into a stunning great room filled with natural light. Pocket corner sliding glass doors open completely to a heated travertine pool deck—resort-style living at its finest. The gourmet kitchen is a chef’s dream with a hidden pantry, natural gas range, pot filler, and stainless KitchenAid suite. From the beamed dining area to the covered terrace and lanai, every space invites relaxed sophistication and seamless entertaining. The lanai includes hookups for a high-end summer kitchen, ideal for those who love to host. Details throughout reflect custom design—coffered ceilings, wrought-iron railings, crown moldings, and hand-finished touches that elevate every room. The first-floor guest or in-law suite includes direct pool access and a full bath for comfort and privacy. Upstairs, the owner’s retreat is a private sanctuary with a round spa bath, large walk-in closet, and a private balcony perfect for morning coffee or evening sunsets. A third bedroom also offers a balcony constructed of Trex for maintenance-free living. This residence balances grandeur with intimacy, artistry with function. A rare opportunity to own one of Florida’s most celebrated luxury homes—where every detail is crafted for those who live beautifully.

624 Canopy Estates Drive, Winter Garden
$975,000
4 Beds ⋅ 3 Baths ⋅ Deer Island Ph 02 SubDv. ⋅ 34787 Zip Code
Bring your ideas to a truly exceptional custom home, perfectly situated in a private, gated community on the shores of breathtaking John’s Lake. Set on over an acre of a beautifully updated landscaped property with panoramic water views throughout the island, this 4-bedroom estate offers the ultimate Florida lifestyle — complete with resort-style amenities and convenient access to Historic Downtown Winter Garden, as well as Downtown Orlando and major attractions just 30 minutes or less away. Your ideas await as charm and craftsmanship are evident in every detail. Step through the front door into an inviting floor plan that seamlessly blends elegance with functionality. The spacious living room is anchored by a cozy wood-burning fireplace, enhanced by warm canned lighting and plantation shutters that frame every window. Wood flooring flows throughout the main living areas, setting a tone of timeless sophistication. The kitchen features granite countertops, KraftMaid cabinetry, Sub-Zero refrigerator, cooktop, double ovens, and a large pantry. The open design keeps the heart of the home connected to the main living space — ideal for entertaining and family gatherings but separate enough to hide the meal prep! The primary suite is a peaceful retreat, with serene views of the pool, dual walk-in closets, garden tub, separate shower, and a cleverly designed storage area. The home's split-bedroom layout ensures privacy for guests and family alike and are all thoughtfully located on the first floor. Upstairs, two large bonus rooms offer endless possibilities — from a playroom to a home theater — and includes a hidden safe room / office with skylights and easy attic access for extra security and utility. The 3 car garage features extra width for additional storage and Gladiator garage organizational wall units. Step outside into your private backyard paradise, where a sparkling saltwater pool and attached hot tub await, surrounded by pavers and an outdoor grilling station. Whether hosting a summer barbecue or enjoying a quiet evening under the stars, this backyard fenced-in space delivers year-round relaxation. Eight outdoor security cameras offer peace of mind, while a three-car garage and spacious driveway provide ample storage and parking. An in-wall pest control system, central vacuum, built-in wine bar, hidden storage and closet organization are examples of many upgrades throughout the home. This home also boasts a well water system with a full purification setup, and a laundry room inside with washer, dryer and utility sink included. Beyond the home itself and its many additional upgrades, the Deer Island community offers unparalleled amenities, including a community boat ramp for direct access to John’s Lake — perfect for boating, fishing, and water sports — as well as two catch and release fishponds, basketball courts, tennis courts, pickleball facilities and easy access to the West Orange bike trails. With stunning lake views, lush surroundings, and a true sense of privacy, this is a place where families grow, memories are made, and every day feels like a getaway. Don’t miss the opportunity to own this fabulous home, where elegance meets comfort and lifestyle meets location.

17608 Deer Isle Circle, Winter Garden
$890,000
4 Beds ⋅ 5 Baths ⋅ Bay Isle 48 17 SubDv. ⋅ 34787 Zip Code
Absolutely Stunning 4BR/3 full bath/2 half bath, Pool Home on Corner Lot with 3-Car Garage! New Roof 2021, New AC unit 2024, New Hot Water Heater March 2025. Located in a sought-after gated neighborhood, this elegant and spacious home features a grand entry, soaring vaulted ceilings, and oversized windows for abundant natural light. The open floor plan includes a cozy family room, dinette, and a chef’s kitchen with stainless steel appliances, double islands, built-in desk, and a separate bar area with sink and cabinetry. The downstairs primary suite offers a luxurious retreat with a large bathroom featuring a separate tub, walk-in shower, and dual vanities. Upstairs includes a second primary suite with full private bath, a Jack-and-Jill bedroom setup, loft, and a media room with theater seating. Enjoy outdoor living in the screened-in lanai with a heated pool and a huge side yard perfect for play or entertaining. Additional highlights: community access to Black Lake with fishing pier, minutes to Winter Garden Village, Stoneybrook Golf Club, and easy access to 429. This home has it all—style, space, and location. Priced to sell—don’t miss out!

14003 Hampshire Bay Circle, Winter Garden
$2,098,500
5 Beds ⋅ 6 Baths ⋅ The Grove SubDv. ⋅ 34787 Zip Code
Pre-Construction. To be built. Discover the perfect blend of old-world charm and modern luxury in this stunning custom French Farmhouse to be built by the renowned Pioneer Builders. Nestled in a picturesque setting, this home will feature classic European-inspired architecture, upscale design, and superior craftsmanship. Step through an arched entryway into an inviting open floor plan adorned with vaulted ceilings, rich wood flooring, glass enclosed wine display and gas fireplace. The gourmet kitchen will be a chef’s dream, boasting custom cabinetry, premium appliances, an oversized island, and a walk-in pantry. The primary suite offers a spa-like retreat, complete with a luxurious ensuite bath, freestanding soaking tub, and spacious walk-in closet. Additional bedrooms provide ample space and can be tailored to your lifestyle. Enjoy indoor-outdoor living with a covered patio, lush landscaping, and sparkling pool, creating the perfect setting for relaxation and entertaining. The Grove is situated within Oakland’s most sought-after neighborhood known for its upscale charm and ideal location . Access to modern amenities, including walking trails, parks, and recreational areas. Close proximity to top-rated schools, shopping, dining, and entertainment. Easy access to major highways, ensuring seamless connectivity to Orlando and surrounding areas. This home is your chance to become part of a vibrant and growing community while enjoying the privacy and comfort of a custom-built home tailored to your lifestyle. Don’t miss this opportunity to secure your spot in one of Oakland’s most desirable locations. Contact us today to schedule a tour and start planning your dream home!

1112 Sarah Mathews Drive, Oakland
$1,425,000
5 Beds ⋅ 7 Baths ⋅ Canopy Oaks Ph I SubDv. ⋅ 34787 Zip Code
BIG PRICE DROP! Welcome to the PARADE OF HOMES 1ST PLACE WINNER and OVERALL GRAND AWARD recipient! This former model home features Authentic French County architecture and a range of impressive amenities. With 5 bedrooms and 5.5 baths, this sanctuary offers refined opulence and individuality. The 2-story foyer with a Juliette balcony sets the tone for the elegance within. The Great Room opens to the lanai and pool area, providing panoramic vistas. The Kitchen boasts Viking appliances and a gas cooktop, perfect for culinary enthusiasts. A hidden wine cellar lies beneath the wood staircase. The lanai and back yard offer a seamless blend of indoor and outdoor living. The Summer Kitchen caters to epicureans, while the pool and pergola provide space to relax and create lasting memories. A natural gas, whole-house generator ensures convenience and security. The first-floor Owner's suite offers spaciousness and privacy. Luxurious amenities include a shower, soaking tub, and a walk-in closet. The second floor features a Gathering Room with a balcony offering sweeping views. The Theater Room with a 120-inch TV and wet bar promises cinematic excellence for all the movie buffs. Three en-suite bedrooms on the second floor provide comfort and style. The DELRAY model spans 4,375 square feet, with a total of 5,531 square feet of pure magnificence. Located in the gated enclave of Canopy Oaks in Winter Garden, this home embodies modern living and exquisite design.

770 Canopy Estates Drive, Winter Garden
$1,650,000
5 Beds ⋅ 4 Baths ⋅ Deer Island SubDv. ⋅ 34787 Zip Code
Under contract- accepting back up offers. Luxury GATED LAKEFRONT community of Deer Island offers 1+ acre estate homes, panoramic views of Johns Lake, and unrivaled privacy. This 1.06-acre single-level home is an ENTERTAINER’S DREAM inside and out. Entering the decorative glass doors is an impressive open-concept floor plan which is framed by panoramic floor-to-ceiling windows highlighting the custom 55’ infinity edge pool and unobstructed lake views. Inside expansive European travertine stone floors and designer finishes adorn the central living areas. The gourmet kitchen is detailed with unique hide-a-ways, and custom lighting with the focal point being an oversized 11.6’ granite island with a 36” Thor 6 burner gas stove and oven and custom wood hood. There is generous room for seating for 12 in the adjacent dining area. Utilize your bonus room for entertainment or relaxation. It is suitable for a pool table and has a full bath that can be accessed from the outdoor deck. Through the spectacular arched solid wood doors lies the owner's suite. Brazilian cherry flooring and cathedral ceilings of solid cherry are impressive. The 10’ accordion impact glass doors lead you to your private upper deck. You’ll enjoy a second fireplace as you soak in the lake views and the serenity of the outdoors. The owner's suite remodel includes dual cedar walk-in closets with temperature-controlled storage above, marble flooring with heated floor system, chandelier, water closet, dual vanities on each side, and a glass-enclosed walk-in steam shower with 2 person jacuzzi tub with heater. Rounding out the main living floor off the front is an office/flex room plus guest bedroom ensuite with travertine walk-in rain shower, wand, jets, specialty lighting and Bluetooth connection. 3 additional Bedrooms on the other side of the home share a travertine stone bath with a double vanity and tub-shower combo, rain shower head, specialty lighting and Bluetooth connection. One guest room has ensuite access to the shared bath, cedar walk-in closet, and a bonus loft. A full-size laundry room and custom pantry with soft close pull-outs located just off the kitchen with matching cabinets and counter space and utility sink. 3-car garage with attic storage. A wide variety of trees on the property include papaya and avocado as well as pineapple. Lakefront you will find a boathouse with a new dock, patio, and large fire-pit enhancing all the lakeside fun! Johns Lake is renowned for its trophy bass fishing, watersports, and 2 ski slalom courses. Deer Island is located just off Highway 50 with easy access to the Turnpike/429. You are only a short drive to Downtown Winter Garden, Disney/ Theme Parks, incredible shopping, dining, and the West Orange Bike Trail.

17509 Deer Isle Circle, Winter Garden
$1,515,000
6 Beds ⋅ 6 Baths ⋅ Canopy Oaks SubDv. ⋅ 34787 Zip Code
BACK ON MARKET! Authentic French County architecture and luxury appointments make this 6 BR, 5 Bath home special and unique. It's why this model won the coveted Parade of Homes award! The soaring 2-story foyer with its charming Juliette balcony provide a hint of the excitement of this home's design. Enter into the Great Room and enjoy the spaciousness and views to the lanai and pool area as well as the pond with fountain that lights at night. A magnificent Kitchen includes Kitchen Aid appliances and a gas cooktop, plus ample space for two chefs, with two islands and an additional prep-sink. The lanai and back yard are designed as additional living space, featuring a Summer Kitchen, large pool, gas firepit and incredible views of the water. The house also has a new water softener and gutters. The first floor Owner's suite is both spacious and private, with a luxurious shower, soaking tub and premium walk-in closet. The wood staircase near the Family Room leads to an incredible second floor with a huge Gathering Room that opens to a 22-foot balcony. Relax and enjoy friendly conversation, or move into the nearby Theater Room with a riser for theater seating and wet bar. The second floor also includes three en-suite bedrooms. The DELRAY encompasses 4,503 SF under air (5,531 total SF). Experience "the new look for the dream home" at Canopy Oaks, a small gated enclave of luxury homes in Winter Garden. This is the largest lot (1/4 acre) with the most gorgeous views in the community! This won't last!

725 Canopy Estates Drive, Winter Garden