Features & Amenities

Interior

  • Other Interior Features

    Crown Molding, Eat-in Kitchen, High Ceilings, Stone Counters

  • Total Bedrooms

    5

  • Bathrooms

    4

  • 1/2 Bathrooms

    1

  • Cooling YN

    YES

  • Cooling

    Central Air, Zoned

  • Fireplace YN

    YES

  • Heating YN

    YES

  • Heating

    Central, Zoned

  • Pet friendly

    Yes

Exterior

  • Garage

    No

  • Construction Materials

    Vinyl Siding, Frame

  • Other Exterior Features

    Rain Gutters

  • Parking

    Circular Driveway, Driveway, Parking Pad

  • Patio and Porch Features

    Covered, Patio, Rear Porch, Wrap Around

  • Pool

    No

  • Waterfront YN

    NO

Area & Lot

  • Lot Features

    Corner Lot, Landscaped, Level

  • Lot Size(acres)

    0.41

  • Property Type

    Residential

  • Property Sub Type

    Single Family Residence

  • Architectural Style

    Traditional

Price

  • Sales Price

    $3,100,000

  • Tax Amount

    $3,875.98

  • Sq. Footage

    3, 896

  • Price/SqFt

    $795

HOA

  • Association

    No

School District

  • Elementary School

    Audubon Park K8

  • Middle School

    Audubon Park K-8

  • High School

    Winter Park High

Property Features

  • Stories

    2

  • Ownership

    Fee Simple

  • Senior Community YN

    NO

  • Sewer

    Public Sewer

  • Tax Lot

    1

  • Water Source

    Public

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Location

County

Orange

Elementary School

Audubon Park K8

Middle School

Audubon Park K-8

High School

Winter Park High

Listing Courtesy of Mick Night , PREMIER SOTHEBY'S INTL. REALTY

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Nestled in the heart of downtown Winter Park, this beautifully maintained 1920s traditional residence captures the essence of Old Florida charm while offering the comfort of modern amenities. From the moment you arrive, the wraparound porch and circular drive create a welcoming first impression, setting the tone for the timeless character found throughout. Step inside to a gracious foyer accented by a cozy fireplace, leading into the spacious formal living room with its own gas fireplace and the elegant formal dining room. Gorgeous heart-of-pine floors run throughout the first floor, adding warmth and authenticity. The kitchen has been thoughtfully updated with top-of-the-line Thermador and Sub-Zero appliances, including a 72-bottle Sub-Zero wine tower and refrigerated drawers, making it as functional as it is beautiful. Open to the family room, complete with rich woodwork and a third gas fireplace, this space is ideal for gathering and entertaining. The primary suite is conveniently located on the first floor and features an updated ensuite bath. Upstairs, three additional bedrooms and two renovated baths provide comfortable accommodations for family and guests. A charming “sleeping room,” now used as a light-filled office, overlooks picturesque New England Avenue. Adding to the property’s appeal is a detached two-story guest house offering a full bedroom, full bath, sitting area, and kitchen—perfect for extended stays or as a private retreat. Outdoor living is equally inviting, with a back porch for grilling, a separate patio for lounging and mature landscaping that enhances the home’s curb appeal. Architectural details available for adding an oversize two-car garage, if desired. Perfectly positioned on the same block as The Alfond Inn and just two short blocks from the renowned Park Avenue district, this home offers not just refined living, but a downtown walkable lifestyle that is truly unmatched. Park Avenue is the cultural heart of Winter Park—a tree-lined promenade alive with award-winning restaurants, boutique shopping, art galleries and historic landmarks. Residents enjoy a vibrant calendar of events, from the Winter Park Farmers’ Market and seasonal art festivals to beloved holiday parades and outdoor movies under the stars. Here, every day is an invitation to experience the best of Central Florida living—whether it’s sipping coffee at a charming café, strolling to or after dinner surrounded by beautiful ambience, or embracing the timeless traditions that make Winter Park so treasured.

457 E NEW ENGLAND AVENUE

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#O6386920

WINTER PARK

2040 RANDALL CIRCLE

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4 Baths

4,636 Sq.Ft.

$3,450,000

MLS#: O6386920

New on site 1 day ago
Artistry and exquisite style are brilliantly showcased in this renovated Winter Park masterpiece. Located in the coveted neighborhood of Park Grove, this magical home is sure to take your breath away, with stunning surprises around every corner. Since 2022, the home has undergone an extraordinary transformation, with more than $700,000 invested in thoughtful renovations, upgrades, and enhancements throughout. Highlights include refinished and new hardwood floors extended across the entire first floor and continued onto the second level with sound-reducing underlayment, renovated bathrooms with designer plumbing fixtures, and new door hardware throughout for a cohesive, high-end finish. A dramatic 16-foot sliding glass door was added by removing the former wall, opening the living spaces to the outdoors with a sleek modern system. Elevated by designer lighting, sophisticated wall coverings, and custom window treatments, the thoughtful floor plan leaves nothing to be desired. At the center of the home, the open family room seamlessly converges with a polished kitchen, separated by an expansive breakfast bar. Sub-Zero, Wolf, and Bosch stainless steel appliances, including a gas cooktop and built-in dual convection ovens, surround a separate prep island. A sun-filled dinette with pool views sits at the far end. Ample storage, a walk-in pantry, built-in workstation, and wet bar/butler’s area with icemaker enhance functionality and entertaining. Lounge or dine beneath two covered lanai areas with electronic screens, or enjoy the newly redesigned & resurfaced pool and deck completed in 2023. Improvements include an expansive sun shelf with bubbler and umbrella sleeve, conversion to a saltwater system, and updated marble pool deck, all surrounded by a newer vinyl fence and block walls lined with tall hedges for privacy. Defined front living and dining rooms feature floor-to-ceiling windows with custom window treatments, while a perfectly placed powder room and coat closet are off the grand foyer. The spacious laundry room, with a laundry chute, is bursting with natural sunlight. The floor plan further enhances functionality with a downstairs Primary Suite featuring French doors that provide direct access to both covered lanais and the backyard. The newly renovated primary bath offers an LED-lit glass shower, soaking tub beneath a window, water closet, and large custom boutique-style walk-in closet. Tucked behind the dinette is the secondary guest bedroom wing currently used as a private office, with French doors, and a renovated full bath accessible from the pool deck. Upstairs features three large bedrooms, two full bathrooms, and a gym equipped with a built-in mini fridge, all centered around an enormous bonus room with built-in cabinetry. The oversized side-facing two-car garage sits off Summerland Avenue’s charming brick street and includes epoxy floors, workshop space or room for bikes & strollers, a second refrigerator, storage cabinets, and extensive hanging storage. The westside lawn was designed with a trellis over the garden area, perfect for homegrown produce. The garden area includes dedicated irrigation lines that feed from the well irrigation system. Other luxury elevated features include a home audio system (inside and out), a whole-house generator, whole-home water filtration system, and integrated security system with hard-wired cameras. This home truly has it all.
#O6387016

WINTER PARK

611 WILLIAMS DRIVE

5 Beds

4 Baths

4,686 Sq.Ft.

$2,995,000

MLS#: O6387016

New on site 2 days ago
Welcome to 1760 Alabama Drive, an architectural standout in Winter Park’s coveted Golden Triangle, known locally as The Vias. Positioned just houses away from some of the most valuable real estate in 32789 and steps from Kraft Azalea Park, this 2,841 sqft mid-century residence sits in one of Winter Park’s most exclusive and tightly held enclaves. Lakefront sunsets, shaded walking paths, and the serenity of the Chain of Lakes lifestyle are at your doorstep with a respected local racquet club just minutes away for those who value both community and an active lifestyle. This is authentic mid-century architecture, thoughtfully modernized without compromising its soul. Clean lines. Intentional geometry. Expansive walls of glass. Natural light floods nearly every room through oversized windows, while dramatic 20 foot hedges on both sides create an extraordinary sense of privacy. You experience openness without exposure a rare and highly desirable balance. At the heart of the home is a true chef’s kitchen featuring completely custom cabinetry and restaurant quality appliances. This is a serious culinary space built for performance and designed with craftsmanship in mind. It flows seamlessly into the main living areas, supporting both elevated entertaining and everyday living. The home offers (4) four bedrooms and (2.5) two and a half baths, including an impressively scaled primary suite that feels like a private retreat. A massive great room anchored by a functional fireplace provides architectural presence and flexibility currently styled as a study or office, but equally suited as a dramatic living space. Step outside and the lifestyle expands. The backyard is designed for gathering, centered around a fully realized outdoor gourmet kitchen and expansive entertaining area made for long evenings and effortless hosting. There remains generous room for a future pool without compromising the integrity of the space, a rare blend of finished outdoor luxury and future optionality in this neighborhood. A private rear driveway and (2) two-car garage add convenience and discretion rarely found in this pocket of Winter Park. In this market, location drives value. This address is not just a location, it’s a strategic position. Architectural distinction, immediate park access, privacy, and proximity to the very best of Winter Park define its enduring appeal.
#O6386409

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4 Beds

2 Baths

2,841 Sq.Ft.

$2,498,000

MLS#: O6386409

Under Construction. Under Construction. Welcome to a brand-new luxury residence coming to one of Winter Park’s most desirable locations. This thoughtfully designed home blends modern elegance with functional living, offering a refined layout, quality craftsmanship, and a lifestyle tailored for comfort and entertaining.

Planned features include an open-concept floor plan with spacious living and dining areas, a designer kitchen with custom cabinetry, premium appliances, and stone countertops, along with carefully curated finishes throughout. The primary suite is designed as a private retreat with a well-appointed bathroom and generous closet space, while additional bedrooms provide flexibility for guests, office space, or multi-generational living. Expansive windows and sliding glass doors are intended to create a seamless connection between indoor and outdoor living areas, ideal for enjoying Florida’s year-round lifestyle.

Outdoor plans may include a covered lanai, pool, and landscaped grounds designed for both relaxation and entertaining. A garage and ample storage further enhance everyday functionality.

This home is currently under construction. All renderings, floor plans, features, and specifications are subject to change without notice. Builder reserves the right to modify plans, materials, and finishes. Qualified buyers may have the opportunity to customize certain design selections and finishes depending on construction stage and builder approval.

Conveniently located near Park Avenue, local dining, shopping, parks, and top-rated schools, this property offers the opportunity to own a new construction home in the heart of Winter Park. Buyers are encouraged to verify all information, including dimensions, features, school zoning, and completion timelines.
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5 Beds

4 Baths

3,800 Sq.Ft.

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If you’re searching for a Winter Park luxury home with quartz countertops, Thermador, engineered hardwood floors, a summer kitchen, automatic screened lanai, and a saltwater pool/spa, 151 Oakwood Way checks every box.


Winter Park FL luxury home, 32789, new construction, custom built, LunDev, open concept, quartz countertops, Thermador appliances, engineered hardwood flooring, resort style backyard, saltwater pool, separate spa hot tub, outdoor kitchen, summer kitchen, automatic screen, covered lanai, flex space, office, game room, plumbing prepped for bedroom conversion.
#O6380037

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151 OAKWOOD WAY

4 Beds

4 Baths

4,129 Sq.Ft.

$3,180,000

MLS#: O6380037

A New Standard of Modern Sophistication in Winter Park
In a city known for its heritage, this ground-up architectural renovation emerges as a bold statement of modern luxury. Located within one of Winter Park’s most coveted enclaves, this four-bedroom, five-bathroom residence is not merely a place to live, but a meticulously crafted experience where high-design meets intuitive living.
Step through the striking 10-foot glass pivot doors into a world defined by light and scale. The soaring foyer gives way to an expansive open-concept floor plan, where the boundary between indoors and out begins to blur. Sleek Italian wood flooring guides you through the main level to the heart of the home: a grand living area anchored by a statement fireplace. It is a space designed for the quiet morning coffee just as much as the vibrant evening gala.
A Symphony of Intelligence. This home lives and breathes with you. Equipped with a fully integrated Control4 automation system, the environment responds to your touch. From your device, you can orchestrate the perfect atmosphere—adjusting custom lighting scenes, streaming high-fidelity music, or setting the climate before you even arrive. This "invisible concierge" extends to the water’s edge, allowing you to manage pool temperatures and lighting with effortless precision.
The kitchen is a masterclass in culinary elegance, blending European minimalism with professional-grade power. Light-toned cabinetry hides clever storage solutions, while premium Sub-Zero and Wolf appliances sit beneath striking Neolith double countertops. It is a space that invites creativity, whether you are hosting an intimate chef-led dinner or enjoying a slow Sunday brunch.
The commitment to "pride of ownership" is felt most deeply in the private quarters. Each of the four bedrooms is a dedicated en suite retreat, featuring voluminous walk-in closets and spa-inspired baths. Custom vanities, Neolith surfaces, and soft, indirect lighting create a hotel-level sense of calm, ensuring every guest or family member feels a sense of total seclusion.
The Backyard Resort. The transition to the outdoors is seamless, revealing a private oasis designed for the quintessential Florida lifestyle. A Brazilian IPE wood deck surrounds a shimmering, heated mini-pebble pool in French gray. Beyond the water, the lushly landscaped grounds lead to a premier summer kitchen clad in sintered stone. Here, under the Florida stars, the integrated grill and sink provide the ultimate setting for al-fresco entertaining.
Experience the pinnacle of Winter Park living. You are situated just moments from the refined energy of Park Avenue, the prestigious Interlachen Country Club, and the scenic beauty of Phelps Park. With zoning for the area’s top-rated schools the location is as strategic as it is beautiful.
Notable Refinements:
• Whole-home generator ensuring absolute peace of mind.
• Finished garage floors and a circular driveway accented with salt and pepper gravel.
• Full-home Control4 integration for music, light, and climate.
Experience the art of living well—connect with us today for an exclusive private tour
**Unique financial opportunities available: The seller is open to owner financing and Bitcoin (Digital Asset/ Crypto) as a medium of exchange. Please reach out to discuss how we can facilitate a transaction tailored to your needs.**
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4 Beds

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3,658 Sq.Ft.

$3,549,995

MLS#: O6378905

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Welcome to 147 Interlachen Place, Enjoy Winter Park's most desirable location! One block from Historic Park Avenue/Central Park. Spacious, bright and all on ONE FLOOR. The buildings second floor offers privacy and easy access. The Southwest corner provides direct natural light throughout the day. Private elevator access with secured underground parking. This beautiful home offers a short walk to everything Winter Park, a pedestrian village of delight! Natural light fills the central courtyard which features an iron water fountain. Private pool with heated spa and outdoor grilling and entertaining area. Interior features include fireplaces in living room, 2 Southwest facing covered outdoor walkout balconies, accessed by living room, den, master bedroom and one directly over looking the pool. Master bathroom includes separate tub and shower, dual closets, split vanities and plenty of storage space. 4 full bath- 1 half bath (5). Two specified parking spaces also have large storage closets with security gate and elevator access to your floor. K-8 Audubon School district! Unit / building “horseshoe” configuration provides no neighbors on any of the 4 sides, courtyard interior, Private Luxury Living all on ONE floor!
#L4959060

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147 S INTERLACHEN AVENUE 202

3 Beds

4 Baths

3,272 Sq.Ft.

$2,550,000

MLS#: L4959060

This stunning custom residence built by respected Winter Park Builder Charles Clayton blends classic elegance with refined modern comfort, offering seamless indoor–outdoor living and impeccable craftsmanship throughout. From the manicured lawn and stately traditional exterior to the welcoming front porch with old Detroit brick, the home’s curb appeal sets a tone of understated luxury, all wrapped in an elegant exterior. A foyer with extensive custom molding immediately captures attention, with sightlines extending to the private backyard and pool which creates a natural flow between interior living spaces and the outdoor retreat. Flanking the foyer, a richly detailed private study features custom millwork and a built-in bookcase, while the formal dining room provides an elegant space for entertaining. Expansive family room/dining area offers extensive molding, a gas fireplace, surround sound, and a wall of French doors which open to a covered Detroit Brick porch, creating a natural flow between interior living spaces and the outdoor retreat including a porch and pool. The space easily accommodates a large casual dining area and opens seamlessly to the kitchen. The light-filled chef’s kitchen showcases extensive marble surfaces, a Sub-Zero refrigerator, large farmhouse sink, and an open layout ideal for gathering. The main-level primary suite is a private retreat with direct porch access, dual walk-in closets. The primary bath features marble finishes, a glass-enclosed shower, pedestal soaking tub, and dual vanities. A spacious mudroom, large laundry room, and pantry area sit just off the kitchen, complete with a half bath and convenient access to the garage and porch. The two-car garage includes additional storage, complemented by a brick driveway. Upstairs, a central stair hall opens to an upstairs Family/Kid’s Gathering/Game Area. Bedroom 2 functions as a second primary-style suite, while bedroom 3 is a private suite with its own sitting area. Bedrooms 4 and 5 share a Jack-and-Jill bath, providing flexible space for family or guests. There is an upstairs storage room. Outdoor open pool with living is equally impressive. This exceptional home offers the ideal balance of architectural character, luxury finishes, engineered wood floor  and a floor plan designed for comfort, privacy, and unforgettable gatherings.
#O6376953

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670 WILLIAMS DRIVE

5 Beds

4 Baths

4,091 Sq.Ft.

$3,190,000

MLS#: O6376953

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Discover an extraordinary residence where exceptional craftsmanship and sophisticated design converge at 948 Poinciana Lane. This meticulously reimagined estate represents the pinnacle of refined living in one of Winter Park's most prestigious neighborhoods, offering an effortless blend of classic architecture and contemporary luxury.
From the moment you step through the elegant foyer, you're greeted by sun-drenched interiors showcasing gleaming hardwood floors, soaring coffered ceilings, and designer details at every turn. The thoughtful floor plan reveals a private home office with custom built-ins and fireplace to the right, and a gracious formal dining room to the left—perfect for hosting memorable gatherings.
The heart of this home is the spectacular kitchen, a true chef's masterpiece featuring custom cabinetry, pristine marble countertops, statement pendant lighting, and top-tier appliances. This culinary haven flows seamlessly into the light-filled family room, where expansive windows frame views of your private outdoor sanctuary.
The first-floor primary retreat is a haven of tranquility, featuring an expansive walk-in dressing room with exceptional storage and a spa-inspired ensuite bath. Luxuriate in the freestanding soaking tub, refresh in the walk-in shower, or prepare for your day at the generous double vanity—all appointed with elegant finishes befitting this caliber of home.
Three generously proportioned guest bedrooms upstairs offer optimal comfort and privacy, complemented by a Jack-and-Jill bath and additional hall bath. A spacious bonus room with backyard views provides versatility for a media room, playroom, or home gym. Above the garage, an additional 260-square-foot bonus room with wet bar and wine fridge creates the ideal entertainer's lounge or game room.
Step through French doors to your private resort-style backyard—a meticulously landscaped oasis featuring a sparkling pool and spa surrounded by lush greenery, stately palms, and thoughtful lighting. Whether gathering around the firepit, lounging poolside, or dining alfresco under the stars, this outdoor retreat elevates everyday living to an art form.
No detail has been overlooked in this complete renovation: designer light fixtures and custom window treatments throughout, first-floor laundry convenience, elevated trim and baseboard, fresh paint, recessed lighting, and three HVAC units ensuring year-round comfort.
The location is simply unparalleled—a leisurely stroll to the Winter Park Racquet Club, zoned for A-rated public schools, and just moments from the world-renowned shops and restaurants of Park Avenue. This is more than a home; it's a lifestyle of distinction in Central Florida's most desirable address.
#O6372165

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948 POINCIANA LANE

4 Beds

3 Baths

3,676 Sq.Ft.

$3,599,000

MLS#: O6372165

Under Construction. Designed with intention and built with precision, this brand-new LUIH Luxury home exemplifies the elegance and livability Winter Park is known for. Every inch of this residence has been curated for those who demand extraordinary design, flawless craftsmanship, and a lifestyle that feels both elevated and effortless. Step through the front door and into a grand two-story foyer where natural light cascades from above, illuminating the level of detail that unfolds in every direction. The main living space is an elegant composition of scale, comfort, and style. A dramatic fireplace anchors the room, while expansive glass sliders dissolve the boundary between indoors and outdoors, creating a seamless entertaining experience. The kitchen is a chef’s dream, featuring custom cabinetry, integrated LED underlighting, quartz countertops, a full Thermador appliance suite, and an oversized walk-in pantry designed for true culinary enthusiasts. The primary suite is a private wing of its own featuring a dedicated office that allows you to work in complete quiet, and a spacious owners suite with large sliders that open directly to the pool and spa. The spa-inspired bathroom features a freestanding tub, an expansive walk-in shower, dual vanities with floating illuminated mirrors, and a large walk-in closet.  Outdoors, the home feels like a private resort, crafted with the same attention to detail and luxury as the interiors. Step through the sliding glass doors and you’re greeted with an expansive covered lanai designed for year-round entertaining, complete with generous dining spaces and a full summer kitchen that feels like an extension of the home. Beyond the lanai this home features a spacious backyard with a large pool and spa. Located in the highly sought-after Kenilworth Shores neighborhood, you’re surrounded by quiet tree-lined streets while being just a golf-cart ride from the boutiques, cafés, and fine dining of Park Avenue. You’re also just minutes from Winter Park High School and the vibrant Cady Way Park, where tennis courts, soccer fields, and baseball fields create an unmatched hub for outdoor recreation.
#O6360737

WINTER PARK

426 WORTHINGTON DRIVE

5 Beds

4 Baths

3,520 Sq.Ft.

$2,679,000

MLS#: O6360737

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