Winter Park Homes with Two Story Property Description

Winter Park Homes with Two Story Property Description

Welcome to Winter Park, Florida—a picturesque city that beautifully blends small-town charm with vibrant urban living. Nestled just north of Orlando, Winter Park is renowned for its stunning lakes, lush parks, and a rich cultural scene that includes art galleries, museums, and the famous Winter Park Farmers’ Market. The city is also home to Rollins College, which adds a youthful energy to the community and hosts various events throughout the year.

One of the most sought-after features in Winter Park’s real estate market is the stunning collection of two-story homes. These properties not only provide ample living space but also offer a unique architectural charm that complements the area's aesthetic. Imagine waking up in a spacious master suite on the second floor, sipping your morning coffee while enjoying breathtaking views of the tree-lined streets or your beautifully landscaped backyard. With expansive open floor plans, these two-story homes are perfect for families, providing room for everyone to thrive.

Many of these homes boast modern amenities, including gourmet kitchens, luxurious bathrooms, and cozy family rooms, all while retaining that classic Florida style. Outdoor living is a highlight in Winter Park, and many two-story homes feature inviting patios or balconies, ideal for entertaining friends or enjoying quiet evenings under the stars.

Whether you’re seeking a vibrant community with excellent schools, beautiful parks, or a home that offers both comfort and elegance, Winter Park’s two-story properties are sure to impress. Discover your dream home in this enchanting city today!

Newest Winter Park Homes with Two Story Property Description

2 Beds ⋅ 2 Baths ⋅ Whisperwood Condo SubDv. ⋅ 32792 Zip Code

This charming 2-bedroom, 1.5-bath condo offers a desirable townhome-style layout with spacious living areas and thoughtful storage throughout. The community features deluxe vinyl fencing installed by the HOA, along with a clubhouse and a community pool, providing great amenities for residents to enjoy. Inside, you’ll find the convenience of an in-unit washer and dryer combo, ample storage under the stairs, and a large carport with an attached storage shed. The spacious primary bedroom opens directly to a generous private balcony—perfect for relaxing or unwinding after a long day. Ideally located just 15 minutes or less from UCF, Rollins College, Valencia East, and Full Sail University, and only 20 minutes from Orlando International Airport. Whether you’re a first-time homebuyer, student, investor, or looking to make your move into Winter Park, this home delivers affordability, convenience, and excellent potential.

7468 Canford Court Unit 24, Winter Park

4 Beds ⋅ 4 Baths ⋅ Meadows At Hawks Crest SubDv. ⋅ 32792 Zip Code

Welcome to 1246 Verdant Glade Place in The Meadows at Hawk’s Crest, where luxury, thoughtful design, and resort-style living come together! This beautifully maintained original-owner 4-bedroom, 3.5-bath home showcases exceptional upgrades, including LVP flooring on both levels, plantation shutters, 8-foot first-floor doors, 5.25-inch baseboards, upgraded cabinetry, custom woodwork, and updated black iron stair railing. The impressive kitchen features quartz countertops, wall oven and microwave, stainless steel appliances, externally vented hood, marble tile backsplash, above- and under-cabinet lighting, and crown molding in the kitchen, dining room, foyer, and half bath. A stunning two-story custom built-in with electric fireplace, display shelving, and storage creates a dramatic focal point in the living area. The first-floor primary suite offers a tray ceiling and custom closet cabinetry, while one upstairs bedroom also features a custom closet. A private office/bonus space and upgraded laundry cabinetry add flexibility and function. Step outside to your own private resort featuring a spectacular saltwater pool and spa with sunshelf, pebble finish, fountains, and bubbler, all within a screened enclosure. Additional highlights include an epoxy-coated garage floor and overhead storage racks. The Meadows includes lawn care, a community pool, splash pad, fitness center, and gated entry. Conveniently located near shopping, dining, major roadways, Winter Park, parks, and trails. This is the Florida lifestyle you’ve been waiting for—come see it now!

1246 Verdant Glade Place, Winter Park

4 Beds ⋅ 2 Baths ⋅ Olympia Heights Annex SubDv. ⋅ 32789 Zip Code

Income Producing Duplex in Winter Park, Florida! Great investment opportunity in a desirable location! This duplex features two 2-bedroom, 1-bath units, each approximately 600 square feet, with private entrances, central AC, and a private screened patio area. Both units are currently leased, providing established rental income and long-term occupancy. Each unit offers a spacious living area and a functional kitchen, with a shared laundry room equipped with a washer and dryer for added convenience. Both units include a full bath with updated showers. Enjoy all of Downtown Winter Park, including the shops and restaurants along Park Avenue, Winter Park Village, and an abundance of entertainment and recreational options such as Mead Botanical Garden, Winter Park Tennis Center, Winter Park Golf Course, and much more. The property also offers easy access to major highways and is just minutes from Rollins College. Don't miss this opportunity to own an income-producing property in one of Central Florida's most desirable areas with no HOA. Pictures were taken prior to occupancy.

2183 Crandon Avenue, Winter Park

4 Beds ⋅ 5 Baths ⋅ Maitland Shores First Add SubDv. ⋅ 32789 Zip Code

Virtually Staged. Beautifully updated and thoughtfully designed, this four-bedroom, three-and-one-half-bath residence blends sophisticated interiors, inviting living spaces and an impressive outdoor setting. Gorgeous curb appeal and meticulously maintained landscaping create a welcoming first impression, while extensive recent improvements bring a fresh, refined feel throughout. Just off the entry, a stately office/den with a wood-burning fireplace offers a handsome, versatile space for a home office, library or sitting room, while a formal dining room provides an elegant setting for entertaining. At the heart of the home is the beautifully updated kitchen, featuring new cabinetry and hardware, marble countertops and an expansive center island with generous seating. Luxury appliances include a striking induction range, integrated refrigerator and convenient beverage refrigeration drawer, while a dedicated coffee bar adds function and style. A sunny breakfast nook provides casual dining space, and the kitchen opens seamlessly to the spacious great room, where French doors lead to the covered lanai and fill the interiors with natural light. A cleverly concealed doorway in the kitchen provides access to the garage and a large bonus room above, complete with a custom wet bar and under-counter beverage refrigerator—an exceptional space for entertaining, recreation or media. Privately positioned on the first floor, the primary suite offers direct access to the covered lanai, an ample custom walk-in closet and spa-inspired bath with dual vanities, soaking tub and glass-enclosed shower. A laundry room with custom cabinetry and powder bath with outdoor access complete the main level. Upstairs, a bright and spacious family room accompanies three additional bedrooms. One features a private en-suite bath, while the remaining two share a Jack-and-Jill bath. All closets feature custom organizational systems. Outdoor living is equally impressive. Accessible from both the great room and primary suite, the covered lanai overlooks the newly refinished heated saltwater pool and spa, surrounded by new non-slip pool deck pavers. Wi-Fi-enabled pool and spa equipment provides convenient app-based control. Redesigned by Signature Landscape, the backyard features a turf area for loungers, dedicated firepit space and new fence installed in 2023, creating a wonderful setting for outdoor entertaining. A professionally installed Mist and More mosquito misting system adds another level of comfort, while a gas line from the street supplies the pool and firepit. Extensive upgrades include three HVAC systems installed in 2024 and 2025, a new water heater, whole-home water filtration system and Ecobee smart thermostats. The interior and exterior were repainted in 2025, complemented by new flooring, baseboards and crown molding, custom window treatments, wallpaper and carefully selected designer finishes. Interiors by nationally recognized designer Jaime Garnet of WYC Designs create a polished, cohesive aesthetic throughout. Ideally located just minutes from downtown Winter Park, the home offers convenient access to exceptional dining, shopping and cultural amenities, along with major roadways for easy connectivity throughout Central Florida. With extensive updates, flexible living spaces, sophisticated interiors and a beautifully redesigned outdoor setting, this exceptional residence is truly move-in ready.

948 Poinciana Lane, Winter Park

5 Beds ⋅ 5 Baths ⋅ Kenilworth Shores Sec 06 SubDv. ⋅ 32789 Zip Code

Under Construction. Located in the Kenilworth Shores neighborhood, this stunning new residence brings an elevated level of new construction to an increasingly desirable pocket of Winter Park. A sophisticated modern farmhouse façade creates an impressive first impression, framed by a sweeping double-entry curved driveway that gives the home a commanding yet welcoming presence. Inside, the open-concept design is both polished and remarkably livable. A dedicated home office sits just off the entry, while the expansive main living space is anchored by a statement entertainment wall with an electric fireplace. Pocketing sliders disappear to create a seamless connection to the covered lanai and backyard, extending the home’s entertaining spaces outdoors. At the center of it all, the chef’s kitchen features Taj Mahal countertops, an oversized island, custom cabinetry, and a complete suite of Stainless steel appliances. A generous dining area and large walk-in pantry add to the home’s effortless functionality. One of the floor plan’s greatest advantages is the inclusion of two bedrooms on the main level, a rarity in Winter Park. The primary suite is particularly impressive, offering a true sense of retreat with a spa-inspired bath featuring dual vanities, a freestanding soaking tub, an oversized walk-in shower, and an expansive custom closet with a center island. The additional downstairs bedroom provides flexibility for guests or multigenerational living. Upstairs, three additional generously sized bedrooms are served by two full baths and a dedicated laundry room, along with an air-conditioned bonus room that easily functions as a sixth bedroom, theater, game room, or fitness studio. In all, the home offers five bedrooms, four and a half baths, a private office, and a climate-controlled bonus space, giving families room to spread out without compromise. The backyard was designed to feel like a private resort. A covered lanai and dedicated cabana with a full summer kitchen overlook the large pool and spa, while generous lawn space provides something increasingly difficult to find in newer Winter Park construction. Located minutes from Park Avenue's shops, cafes, and restaurants and close to Advent Health Winter Park, Cady Way Park, and the YMCA, this home offers an exceptional location. For those seeking new construction without compromising on space, location, or lifestyle, this is a Winter Park home that checks the boxes that matter.

648 Worthington Drive, Winter Park

4 Beds ⋅ 4 Baths ⋅ Fontainebleau SubDv. ⋅ 32789 Zip Code

Built in 2017 and thoughtfully enhanced with over $130K in recent improvements, this modern and sleek Winter Park residence is tucked along a quiet dead-end street, offering a functional, open floorplan in an exceptional location. Recent upgrades make this home feel wonderfully fresh and new, including a Mosquito Nix misting system for year-round outdoor pest control, Culligan whole-home water filtration system, fresh paint throughout the entire home, a beautifully remodeled spa-inspired Primary bathroom, renovated powder room, Lutron smart dimmer switches with upgraded LED lighting, a custom-built marble fireplace wall…and the list goes on! Offering 4 bedrooms and 3.5 bathrooms, with a dedicated office, upstairs loft area, and the potential for two laundry rooms, this home masterfully pairs modern design with comfortable everyday living. A soaring 20-foot foyer makes for an impressive introduction, with a private home office just off the entry. The open-concept living spaces center around a sleek chef’s kitchen with an oversized 8.5-foot island, quartz countertops, Thermador appliances, a 6-burner gas range with stainless steel hood, wine refrigerator, and large pantry. The adjoining dining and living areas enjoy views of the pool and spacious backyard, while a newly added electric fireplace with a custom marble wall creates a stunning focal point. The enormous 1st floor Primary Suite has undergone an extensive remodel, including new dual custom walk-in closets with a built-in wall safe, a new floating dual vanity with an anti-fog LED mirror, and an upgraded walk-in shower with a new privacy/glass combination wall, multiple shower heads, and a new freestanding soaking tub. Upstairs, a loft area offers tremendous versatility and connects 3 additional bedrooms, all with new modern LVP flooring (NO carpet) and walk-in closets. Two bedrooms share an updated hall bath with new marble flooring. The 4th bedroom is privately positioned on the opposite side of the home with an en-suite bath and French doors leading to a private balcony. The former upstairs utility space has been thoughtfully transformed into a kitchenette with custom cabinetry, new countertops, a utility sink, and a built-in microwave. This area is especially valuable for extended stays or a secondary living arrangement. A custom work/study area was also added to the rear bedroom for added flexibility. Outside, the fully fenced backyard is lined with a lush bamboo wall and majestic palms, creating a private retreat with a saltwater pool, covered lanai, and ample remaining space for pets or outdoor entertaining. The covered lanai and pool area provide convenient access to the powder bath, recently renovated with gorgeous, marbled floor-to-ceiling tile. The 2-car garage features wall-mounted shelving, multiple overhead storage racks, and durable flooring, plus glass doors for natural light and a sleek appearance. The sellers partnered with Terra Energy to install solar panels on the roof, providing significant savings on their electric bill. (This fantastic subscription service is $186/month with the solar panel company, and additional information will be provided!) With its contemporary architecture, flexible floorplan, substantial recent investments, and highly coveted location, 2343 Versailles Avenue offers the rare combination of newer construction and extensive upgrades in the heart of Winter Park.

2343 Versailles Avenue, Winter Park

6 Beds ⋅ 5 Baths ⋅ Timberlane Shores SubDv. ⋅ 32789 Zip Code

Under Construction. Beautifully composed from every angle, this extraordinary residence captures something increasingly rare in new construction: a genuine sense of character, permanence, and architectural identity. Designed by Gary Hancock and meticulously executed by Vimaro Homes, this home features extraordinary materials, bespoke details, and spaces that feel equally refined and inviting. Set on a large corner homesite in Timberlane Shores, the residence enjoys an uncommon sense of openness, complemented by beautiful lake views from its upper levels. Inside, a striking marble mosaic foyer introduces interiors where every finish has been carefully considered. The main living room is a showpiece, featuring illuminated tray ceilings, extensive custom millwork, a bespoke built-in feature wall, and a fireplace wrapped in Calacatta marble. Expansive pocketing sliders disappear to seamlessly connect the living space with the covered lanai, creating an effortless transition between indoor and outdoor entertaining. At the heart of the home is a chef's kitchen designed to be a true showpiece. Calacatta marble countertops, custom inset cabinetry, a statement ILVE range, paneled built-in refrigerator, and a full suite of Thermador appliances establish an exceptional level of finishes. Just beyond, a large secondary prep kitchen provides plenty of additional storage. A charming breakfast nook offers a more intimate setting for everyday dining, while the formal dining room has been designed for memorable evenings, complemented by a sophisticated bar and glass-enclosed wine display. The first-floor primary suite is a true retreat with direct access to the lanai, custom millwork, illuminated tray ceilings, and an impressive sense of scale. Its spa-inspired bath is finished with marble flooring, Perrin & Rowe fixtures, dual vanities, a freestanding soaking tub, and an oversized walk-in shower. Completing the suite are designated his-and-hers closets, providing an exceptional amount of storage and functionality. An additional main-level bedroom can be used as a guest suite, private office, or library. Upstairs, the home continues to impress with four additional bedrooms and a spacious second living area. Above, a third-floor bonus space provides yet another dimension of flexibility and can be transformed into a private gym, game room, media room, or secluded retreat. From the upper levels, glimpses of the nearby lake further reinforce the home's special setting. Outdoors, the residence was created to embrace the Central Florida lifestyle. The outdoor spaces were conceived as a true extension of the home, with a covered terrace that creates an inviting setting for everything from relaxed afternoons to evening gatherings. Retractable screens allow the space to be enjoyed throughout the year, while a beautifully appointed summer kitchen makes outdoor dining effortless. Beyond, the pool is framed by an oversized patio, manicured grounds, and thoughtfully layered landscaping. This home offers a location that is difficult to replicate. Tucked within the peaceful enclave of Timberlane Shores, the home is just minutes from Park Avenue's shopping and dining, while remaining within walking distance of Blue Jacket Park and the dining, shopping, and lifestyle of Baldwin Park. The property is also zoned for the highly desirable Audubon Park K-8 School. IF PURCHASED EARLY, THE INTERIOR OF THIS HOME CAN BE CUSTOMIZED TO THE NEW OWNERS PERSONAL TASTE. CALL FOR ADDITIONAL DETAILS.

620 Virginia Drive, Winter Park

3 Beds ⋅ 3 Baths ⋅ Enclave At Hawks Crest SubDv. ⋅ 32792 Zip Code

This exceptional 3-bedroom, 2.5-bathroom end unit townhome is in pristine, move-in ready condition, combining low-maintenance living with the privacy of an end unit and the convenience of an attached 2-car garage. At the heart of the home, the impressive kitchen comes fully outfitted with elegant granite countertops and a sleek suite of stainless steel appliances, offering a stylish, high-performing hub for daily cooking and entertaining. Designed with comfort and quiet transition in mind, soft carpets on the stairs and second floor bring warmth and noise reduction to the private upstairs sleeping quarters. Spotlessly prepared and meticulously maintained from top to bottom, this turnkey residence is completely ready for a stress-free transition into a comfortable lifestyle.

1427 Broad Wing Lane, Winter Park

4 Beds ⋅ 4 Baths ⋅ Lake Forest Park SubDv. ⋅ 32789 Zip Code

Under Construction. In a coveted Winter Park enclave, this masterful LUIH residence balances contemporary grandeur with effortless livability. Spanning 2,500 square feet of open-concept living space, the home features four bedrooms and three-and-a-half lavish bathrooms. Framed by hand-selected architectural stone, the elegant entryway reveals a luminous interior anchored by wide-plank light oak flooring that flows seamlessly across both levels. At the heart of the home, the chef’s kitchen boasts a premium Thermador appliance suite, custom Fabuwood shaker cabinetry, vein-matched quartz countertops, a custom pot-filler, and a wine refrigerator. The main-level primary suite offers a true private sanctuary, highlighted by a spa-inspired bath with a freestanding soaking tub, gold-brushed hardware, and a frameless glass walk-in shower. Dissolving the boundaries between indoors and out, the main living area opens to an expansive covered lanai complete with a summer kitchen and a built-in grill. This alfresco retreat overlooks a private, resort-style backyard centered around a saltwater pool, perfectly designed for relaxation or grand-scale entertaining. Zoned for Audubon K-8 and Winter Park High School, and located just minutes from Park Avenue, Trinity Prep, and Lake Highland, this residence presents an unparalleled opportunity for elevated luxury in one of Central Florida’s most exclusive locations.

2308 Mulbry Drive, Winter Park

2 Beds ⋅ 3 Baths ⋅ Temple Trail Village SubDv. ⋅ 32789 Zip Code

A rare opportunity in Winter Park’s coveted 32789! This stunning fee-simple townhome offers the feel of a private retreat with the architectural pedigree of Fugelberg Koch (FK Architecture), the freedom of NO HOA FEES, and an extraordinary setting overlooking the 80-acre Howell Creek Preserve. Tucked away in a highly desirable Winter Park location, this 2-story end-unit lives much larger than its 1,701 square feet and delivers a lifestyle that is truly hard to replicate. The heart of this home may just be its incredible outdoor living space. Step through the living area and onto the expansive deck, where a covered canopy creates a year-round outdoor room overlooking the lush Howell Creek Preserve. With a firepit, market lighting, and treetop views stretching across the native Florida landscape, this is the kind of space that begs you to linger—morning coffee surrounded by nature, afternoon cocktails with friends, or evenings gathered around the fire under the lights. The elevated vantage point places you virtually eye-level with the cypress canopy, creating a dreamy sense of privacy and connection to nature that is rarely found in townhome living. And perhaps best of all, this is a view that cannot be renovated into another home. Inside, soaring 14-foot ceilings and dramatic picture windows fill the living room with an abundance of natural light while framing beautiful views of the preserve. The open, airy design makes the home feel exceptionally spacious and brings the outdoors in. The stunning kitchen features gorgeous Spanish tile flooring, solid wood cabinetry, granite countertops, and a new backsplash. The dining room adds character with built-in cabinetry and French doors, while the spacious indoor laundry room provides exceptional everyday convenience. Upstairs, two generously sized bedrooms and two full bathrooms provide a comfortable private retreat. A convenient powder room is located downstairs for guests. The coveted end-unit location also offers additional outdoor space along the side of the home, beautifully enhanced with brick hardscaping and room for relaxing, grilling, entertaining, or overflow parking. Parking is another standout feature, with a one-car garage plus two designated parking spaces—a rare convenience in this setting. And then there is the location. Situated in the prestigious 32789 zip code, this home puts you within walking distance of the Winter Park Racquet Club, the Winter Park Chain of Lakes, and surrounded by some of Central Florida’s most sought-after real estate. Enjoy the best of Winter Park while coming home to your own private perch above the trees. Fee-simple ownership. No HOA fees. Exceptional architecture. Preserve views. Incredible outdoor living. Coveted Winter Park location. This is far more than a townhome—it is a lifestyle.

2881 Temple Trail, Winter Park

5 Beds ⋅ 5 Baths ⋅ Fontainebleau SubDv. ⋅ 32789 Zip Code

Discover this exceptional custom-designed modern pool home, ideally situated in one of Winter Park's most sought-after neighborhoods. Located on a quiet street, this spacious residence offers 5 bedrooms, 4.5 bathrooms, and a large upstairs loft—providing the perfect blend of luxury, comfort, and functionality. From the moment you enter, you'll be captivated by the abundance of natural light and stunning hardwood floors that flow throughout the main level and continue upstairs into the loft and primary suite. The thoughtfully designed floor plan includes a downstairs bedroom and full bath, ideal for guests, in-laws, or a private home office. Designed with the entertainer in mind, the gourmet kitchen is a true showstopper—featuring quartz countertops, an oversized island, Jenn Air appliances including a double oven, and generous cabinet space. A large butler’s pantry with an additional sink offers even more storage and prep space. Seamlessly transition from indoor to outdoor living with the sliding glass doors that open to a covered lanai, private pool, and expansive fenced in backyard—perfect for relaxing or hosting gatherings year-round. Upstairs, the luxurious primary suite includes a walk-in closet and a spa-like bathroom with dual sinks, a soaking tub, and a separate walk-in shower. Three additional bedrooms, two full bathrooms, and a spacious laundry room with more storage complete the upper level. Additional features include a dedicated mudroom with built-in bench seating and storage, and an air-conditioned two-car garage with insulated doors and epoxy floors. All of this, just minutes from the Winter Park Racquet Club, Park Avenue’s boutique shopping and dining, and top-rated schools: Dommerich Elementary, Maitland Middle, and Winter Park High. Don’t miss this rare opportunity to own a one-of-a-kind home in one of Winter Park's premier neighborhoods.

2407 Lafayette Avenue, Winter Park

5 Beds ⋅ 6 Baths ⋅ Park Grove SubDv. ⋅ 32789 Zip Code

Under Construction. Designed to capture the timeless character of Olde Winter Park while delivering an extraordinary level of modern luxury, this is a truly one-of-a-kind residence by Vimaro Homes. Set within the highly sought-after Park Grove neighborhood and designed by renowned architect Gary Hancock, the home makes an unforgettable first impression with a stately front façade, manicured grounds, dual porte cochere’s, and a motor court leading to a two-car garage. Every element has been thoughtfully considered to create a residence that feels as though it has always belonged in Winter Park. Inside, exceptional craftsmanship takes center stage. A marble mosaic entry introduces interiors defined by chevron-pattern hardwood flooring, refined millwork, natural stone, and carefully curated finishes. The floor plan is equally impressive, balancing grand entertaining spaces with an effortless sense of livability. The main level features a dedicated library/home office, formal dining room, and expansive gathering room overlooking the private courtyard. At the heart of the home, the chef’s kitchen pairs Calacatta marble countertops with a full suite of Thermador appliances, a statement ILVE range, and an oversized butler’s pantry offering exceptional prep and storage space. The first-floor primary suite is a private retreat with direct access to the courtyard and an incredible spa-inspired bath finished in marble. Dual vanities, Perrin & Rowe fixtures, a freestanding soaking tub, walk-in shower, and an expansive dressing room elevate the suite to another level. Upstairs, four generously proportioned bedrooms each feature an ensuite bath and walk-in closet, surrounding a spacious central loft ideal for an additional living or entertaining space. Continuing to the third level, a fully finished attic space provides an unexpected bonus room perfectly suited for a private gym or a game room. The outdoor living experience is just as remarkable. At the center of the home is a spectacular courtyard-style pool, creating a private resort atmosphere framed by the residence and lush landscaping. An expansive covered cabana provides multiple areas for dining and lounging, complemented by a fireplace and full summer kitchen for year-round entertaining. Beyond the courtyard, ample yard space adds another layer of usability rarely found with such an intimate outdoor design. This home also offers the rare opportunity to enjoy one of Winter Park’s most desirable residential settings while remaining within walking distance of the boutiques, acclaimed restaurants, cafés, and vibrant atmosphere of Park Avenue. Hannibal Square and Winter Park Village are also just moments away, placing some of the city’s best dining, shopping, and entertainment within effortless reach. Timeless in its architecture and uncompromising in its execution, this home is destined to become one of Winter Park’s most distinguished residences. Renderings are artistic interpretations. Features and finishes may vary from final construction.

857 Brock Street, Winter Park

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