Winter Park Homes with Cathedral Ceiling(s) Interior Features

Winter Park Homes with Cathedral Ceiling(s) Interior Features

Welcome to Winter Park, Florida, a charming city known for its picturesque landscapes, vibrant arts scene, and a welcoming community spirit. Nestled just north of Orlando, Winter Park boasts a rich history and a blend of old-world charm with modern amenities. With its tree-lined streets, serene lakes, and beautiful parks, this city offers a perfect backdrop for those looking to settle down in a tranquil yet lively environment.

One of the most captivating features of homes in Winter Park is the stunning cathedral ceilings that grace many interiors. These soaring ceilings not only create an expansive sense of space but also allow natural light to flood the rooms, enhancing the warm and inviting ambiance. Imagine hosting gatherings in a living room where the height of the ceilings draws the eye upward, creating an atmosphere of elegance and grandeur.

Homes with cathedral ceilings often come with open floor plans, giving you the flexibility to design your living space to suit your lifestyle. Whether you’re entertaining friends or enjoying a quiet evening at home, these architectural details elevate everyday living, making your home feel both spacious and intimate.

Winter Park is not just about beautiful homes; it’s a lifestyle. With a plethora of boutique shops, gourmet restaurants, and cultural events, residents enjoy a vibrant community that celebrates the arts and outdoor activities. From the enchanting Winter Park Chain of Lakes to the renowned Morse Museum of American Art, there’s always something to explore.

Discover your dream home in Winter Park, where stunning architecture meets a lifestyle of leisure and culture. Experience the magic of cathedral ceilings and the warmth of a community that feels like home.

Newest Winter Park Homes with Cathedral Ceiling(s) Interior Features

617 N Interlachen Avenue, Winter Park
$4,695,000
11 Beds ⋅ 8 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code
Designed by renowned architect James Gamble Rogers II, 617 N Interlachen Ave presents a rare opportunity to own and thoughtfully reimagine a distinctive Spanish Revival estate in the heart of Winter Park. Built in 1929, renovated in 1981, and featuring extensive roof updates completed in 2020 and 2021, this character-filled property reflects the timeless architectural appeal that makes Winter Park so special. Situated on approximately half an acre, the estate includes a main residence plus three accessory buildings encompassing approximately 6,354 square feet combined, providing an exceptional amount of space and flexibility to create a property tailored to your lifestyle and vision. From the moment you arrive, the classic Spanish Revival influence and established setting offer a sense of history and individuality rarely found in newer construction. The multiple buildings create exciting possibilities for guest accommodations, private home offices, studios, hobby spaces, entertaining areas, or other uses permitted by applicable zoning and regulations. The residence offers an opportunity to preserve its distinctive architectural character while updating and personalizing the interiors and amenities for today's lifestyle. For buyers who appreciate homes with a story, architectural distinction, and the potential to make a property uniquely their own, this estate stands apart from the typical Winter Park offering. Even more compelling is the location. The property is within walking distance of Winter Park's famous Park Avenue, renowned for its restaurants, boutiques, cafes, galleries, cultural attractions, and unmistakable charm. Enjoy the rare opportunity to leave the car at home and stroll to one of Central Florida's most celebrated dining, shopping, and entertainment destinations. Rollins College is also nearby, while convenient access to downtown Orlando combines the charm and sophistication of Winter Park with easy connectivity to the greater Orlando area. The property is not individually listed on the Winter Park Register of Historic Places and is not located within a locally designated historic district, an important consideration for buyers exploring future renovation and personalization plans. Buyers should independently verify applicable zoning, permitting, building, and preservation requirements for any intended improvements or uses. With its James Gamble Rogers II design, 1929 origins, Spanish Revival character, approximately half-acre setting, substantial combined square footage, three accessory buildings, and an outstanding location within walking distance of famous Park Avenue, 617 N Interlachen Ave is far more than a conventional home purchase. It is an opportunity to take a distinctive piece of Winter Park architecture and shape its next chapter. Bring your vision and discover the possibilities where history, architecture, location, and potential come together in a truly one-of-a-kind Winter Park estate.

617 N Interlachen Avenue, Winter Park
148 Oak Grove Rd, Winter Park
$320,000
3 Beds ⋅ 2 Baths ⋅ Winter Park Oaks SubDv. ⋅ 32789 Zip Code
Virtually Staged. Winter Park living, without the Winter Park price tag! This 3 bed, 2 bath block home has already done the big stuff for you: 2020 roof, 2020 HVAC, 2023 water heater, and updated plumbing. That means your weekends are for enjoying life where you call home. Fresh paint inside and out sets the tone the moment you pull up. Step inside to a bright, open floor plan where the kitchen, dining, and living spaces flow together for easy weeknight dinners and lazy Saturday mornings. The kitchen and bathrooms have been updated with a clean, modern feel, so all that’s left is to unpack. Out back, a fully fenced vinyl yard gives you privacy and room to play, garden, or host the cookout. A one-car garage adds plenty of storage. And the location? It’s hard to beat. You’re minutes from everything Winter Park has to offer, tucked right behind the new LifeTime fitness club, with exciting new development planned for the area. Homes this updated in this location don’t come around often. Schedule your showing today!

148 Oak Grove Rd, Winter Park
1660 Orange Avenue, Winter Park
$479,900
3 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code
Don’t miss this wonderful opportunity to own a 3-bedroom, 2-bath home in the desirable Orwin Manor area of Winter Park, conveniently located just minutes from AdventHealth, Park Avenue, Downtown Orlando, and I-4. This spacious two-story home features a flexible layout with a two-car garage, remodeled bathrooms, and plenty of living space. The first floor offers a large bedroom, a beautifully remodeled full bathroom, a laundry area and access to the enclosed/screened patio and backyard. Upstairs, you’ll find an open kitchen with stainless steel appliances, a dining area, and a spacious living room. The second floor also features two bedrooms, including the primary bedroom with a remodeled bathroom. Wood flooring and carpet are featured throughout the home. Additional improvements include a roof approximately 5 years old, completely refreshed landscaping and outside power washed. Sliding doors off the kitchen and dining area lead to a new outdoor deck, creating an ideal space for outdoor dining, entertaining, and enjoying the Florida lifestyle. The convenient location provides easy access to major roads, shopping, dining, entertainment, and all that Winter Park and Downtown Orlando have to offer. This home offers a great combination of location, space, and recent updates. Schedule your showing today!

1660 Orange Avenue, Winter Park
7348 Grand Avenue, Winter Park
$285,000
3 Beds ⋅ 2 Baths ⋅ Oakcrest-516 SubDv. ⋅ 32792 Zip Code
Welcome! This three-bedroom, two-bathroom home in Winter Park presents a genuine opportunity for buyers ready to reimagine this one-story residence. The open floor plan creates a flexible living space, and the thoughtful layout gives you a solid foundation to work with. Inside, the cathedral ceiling in the main living area draws the eye upward and enhances the sense of openness throughout the home. The covered rear lanai extends your entertaining and living space outdoors, perfect for relaxation or gatherings. The location delivers great convenience, with proximity to Publix-anchored shopping and Walmart for everyday needs, Red Bug Lake for outdoor recreation activities, grade schools, and the Winter Park Village for shopping and dining. Schools are nearby, making this neighborhood accessible for residents. The central location means you're less than 30 minutes from Orlando International Airport, Universal, Downtown Orlando, and UCF, offering both lifestyle flexibility and strong rental demand drivers for those considering income-producing use. Convenient access to major roadways makes commuting and daily needs straightforward. Schedule your private showing today and bring your vision for what this home can become.

7348 Grand Avenue, Winter Park
2383 Sun Valley Circle Unit 2383, Winter Park
$234,900
2 Beds ⋅ 2 Baths ⋅ Cedarwood Village SubDv. ⋅ 32792 Zip Code
Don't miss your opportunity on this super clean 2 bed 2 bath Winter Park condo! Updated kitchen with White shaker cabinets, granite counters complete with all the appliances including washer and dryer. Formal dining room and family room with vaulted ceilings, skylights, along with a wet bar and cabinetry complimented by a centerpiece wood burning fireplace. Master bedroom features hardwood flooring along with updated vanity with granite counters along with a separate tub and shower. Secondary bedroom has laminate flooring along with updated vanity and granite countertops. Ceramic tile throughout the rest of the home as there is no carpet. French doors leading out to the oversized screen enclosed covered patio overlooking lush landscaping with no direct rear neighbor.  2 assigned parking spaces directly in front of the unit.There is also a small courtyard just outside the kitchen. Community features a recently remodeled pool, clubhouse and tennis courts. Winter Park location benefits include easy access to Full Sail University, UCF, Valencia College, Park Avenue filled with famous restaurants and boutique shopping.

2383 Sun Valley Circle Unit 2383, Winter Park
7506 Cranes Creek Court Unit 30, Winter Park
$365,000
3 Beds ⋅ 3 Baths ⋅ Cranes Creek SubDv. ⋅ 32792 Zip Code
Beautiful, move in ready townhouse located in the highly desirable area of Winter Park. This well-maintained home provides confort, convenience and a versatile layout perfect for modern living. Featuring a spacious 2 car garage and a flexible 4th room on the first floor, ideal for a home an office, guest bedroom or additional living space. Enjoy being just minutes from shopping, dining and everyday essentials, all while living in a quiet and attractive community. This home is the perfect blend of style, functionality and location. Ready for its next owner.

7506 Cranes Creek Court Unit 30, Winter Park
3302 Royal Street, Winter Park
$269,900
3 Beds ⋅ 2 Baths ⋅ Coronation Add SubDv. ⋅ 32792 Zip Code
Come see this 3 bedroom 2 bath split plan home. All tile throughout home. Granite kitchen countertops. Eat in area in kitchen. Kitchen bar opens to great room. Huge corner lot great for handyman with trailer, boat, RV or truck to park in backyard. Easy access to add on garage in backyard. Cathedral ceilings great room. NO HOA.

3302 Royal Street, Winter Park
2308 Mulbry Drive, Winter Park
$1,699,000
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
1840 Bryan Avenue, Winter Park
$1,725,000
4 Beds ⋅ 4 Baths ⋅ Lakeview Terrace SubDv. ⋅ 32789 Zip Code
Welcome to modern luxury in the heart of Winter Park! This custom 2014-built estate rests on an expansive double lot in the highly sought-after Lakeview Terrace community. Offering nearly 3,800 sq. ft. of sophisticated yet comfortable living space, this 4-bedroom, 3.5-bath residence combines timeless architectural details—including soaring vaulted ceilings, crown molding, and dark hardwood floors—with the ultimate layout for functional living. An inviting foyer with volume ceilings and a large transom window fills the home with natural light, leading into a spacious family room anchored by a marble-wrapped electric fireplace with custom lighting and a media niche. The chef’s kitchen is open, bright, and ideal for entertaining, featuring 42-inch shaker double-stacked cabinetry, premium Bosch stainless steel appliances, granite countertops, a designer backsplash, a large pantry, and peninsula bar seating alongside an eat-in breakfast nook. Seamlessly connected, the formal dining room shines with a tray ceiling, custom wallpaper, and designer fixtures. Convenience continues in the oversized laundry room, equipped with a second refrigerator and secondary pantry. Designed for total flexibility, the main level features a dedicated executive office, a media room, a secondary guest suite, and a lavish primary retreat. The primary suite boasts custom built-ins, a massive walk-in closet, direct outdoor access, and a spa-inspired bath with double vanities, a soaking tub, and a large dual-head shower. Upstairs, you’ll find two additional spacious bedrooms, a full bath, and a versatile bonus loft. Outside, a private resort oasis awaits with an open-air lanai and covered porch for alfresco dining, surrounded by lush mature landscaping, pathways trimmed with turf grass, and professional landscape lighting. The heated pool and spa feature a sun shelf with a fountain feature and linear fire elements along the edge that transform the backyard at night. Completing the estate is a 3-car total garage layout, featuring an attached 2-car garage plus a separate detached structure with guest house, studio, or private office potential. Located just one mile from historic Park Avenue, zoned for top-rated schools (Lakemont Elementary, Glenridge Middle, Winter Park High), and walkable to Phelps Park, the YMCA, and local dining.

1840 Bryan Avenue, Winter Park
2450 Grand Teton Circle Unit 2450, Winter Park
$250,000
3 Beds ⋅ 2 Baths ⋅ Cedarwood Village 1 SubDv. ⋅ 32792 Zip Code
Rare end units like this don't come around often! Welcome to 2450 Grand Teton Circle, tucked away in the well-maintained, established community of Cedarwood Village in Winter Park. This 3-bedroom, 2-bath home is filled with natural light thanks to its end-unit location, and the open layout makes it easy to relax, entertain and enjoy everyday living. The spacious living and dining areas flow together nicely, while the kitchen offers plenty of room to cook, gather, and stay connected with family and friends. Over the past several years, this home has been thoughtfully updated, giving the next owner peace of mind. Major improvements include a new roof, skylights, HVAC system, water heater, kitchen appliances, washer and dryer, updated LED lighting, and fresh interior paint. Both bathrooms have been beautifully remodeled, the home has been replumbed by the HOA, and the primary closet has been enhanced with custom shelving. Additional updates include new flooring in the secondary bedrooms, updated window blinds, and thoughtful finishing touches throughout. The private screened lanai has been transformed into a cozy outdoor retreat with fresh paint, a ceiling fan, new screens and screen door, string lighting, and decorative greenery—making it the perfect place to enjoy your morning coffee or unwind after a long day. Life here is easy. Cedarwood Village is a beautifully maintained, established community featuring a community pool and Clubhouse for your special events, tennis courts, and pickleball courts. The HOA has also recently repainted the exterior of the buildings, helping keep the neighborhood looking fresh and inviting. Best of all, this home is value priced, giving you an incredible opportunity to own in desirable Winter Park without the premium price tag. You're just minutes from Winter Park's shopping and dining, Full Sail University, UCF, major employers, and convenient access to SR-417 and downtown Orlando. If you've been looking for a move-in-ready home in a fantastic location with years of thoughtful updates already completed, this rare end unit is definitely worth a look!

2450 Grand Teton Circle Unit 2450, Winter Park
2228 Azalea Place, Winter Park
$5,600,000
5 Beds ⋅ 6 Baths ⋅ Maitland Shores First Add SubDv. ⋅ 32789 Zip Code
Virtually Staged. This elegant transitional French Provincial residence was the feature home in the Orlando Museum of Art's 2022 "mystery home tour" and is located on a large, elevated corner lot in a quiet and secluded area in the Via’s of Winter Park. This residence has been significantly enhanced inside and out by the current owner. The home features 5,200 square feet of living space and 800+ square feet of outdoor space with 5 bedrooms, 5 bathrooms ensuite, 1 half bathroom, 3 car garage, pool, patio and professionally landscaped yard and lighting. Upon entry, you are welcomed through the exquisite foyer where you instantly notice the craftsmanship and expert care that went into the custom carpentry and crown molding details throughout. To the left of the foyer is an elegant and intimate parlor with grass cloth wallpaper, a gas vented fireplace and built-in bookshelves. To the right of the foyer is the formal dining room with beautiful hand painted wallpaper and an adjacent butler’s pantry. Past the foyer you are led to a spacious and grand formal living room with 6 new French iron doors that flow out to a covered brick porch and picturesque back yard & pool. Designed with entertainment in mind, the adjoining chef’s kitchen includes newly painted custom cabinetry, a Sub-Zero/Wolf appliance package, a grand center island and a walk-in pantry. Built in desk and casual dining area all open to the adjoining beamed ceiling family room with gas vented fireplace and additional French doors that lead to street side patio with new awnings. First floor master retreat overlooks the pool & yard and features 14-foot wood beam vaulted ceilings. The oversized master bath with double custom lacquered vanities made in Palm Beach, mosaic marble shower and a Waterworks free standing tub, brushed brass fixtures, and walk in closet. The second-floor features nine-foot ceilings with four bedrooms (one which was converted to a beautiful women’s dressing room) and four ensuite bathrooms, covered balcony adjoining two bedrooms, two built in desks and bookshelves for office/study time and large media room with big screen tv and wet-bar. There are also two laundry rooms, one upstairs and one downstairs. Attic space inside the home and inside the garage. Recent upgrades include slate roof/swooped decorative copper roof with chimney caps, complete chimney rebuild, nine iron French doors, white oak tongue and grove hardwood floors, renovated master bath and two ensuite baths, two new HVAC home units and a new garage mini-split air conditioner. This home offers boat access to the Winter Park chain of lakes and is within short distance of the Winter Park Racquet Club. It’s also a bike ride away and a short drive to the Interlachen Country Club and Park Avenue shopping and dining district. The property is zoned for Dommerich Elementary, Maitland Middle School, and Winter Park High School. One or more rooms virtually staged

2228 Azalea Place, Winter Park
1571 Woodland Avenue, Winter Park
$6,000,000
5 Beds ⋅ 8 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code
Experience timeless elegance and deliberate craftsmanship in the heart of prestigious Winter Park. This one-of- a-kind exceptional estate offers more than 7,300 square feet across three beautifully designed levels, blending refined luxury with modern comfort. Rich architectural details include solid red oak flooring with a walnut finish, nearly 10-foot ceilings, stacked crown moldings, custom ironwork, designer lighting, and extensive millwork throughout. The gourmet kitchen is thoughtfully appointed with Viking and GE Monogram appliances, custom Busby cabinetry, an oversized island, and a butler’s pantry. It also includes multiple filtered water and ice zones designed for effortless entertaining. The spacious primary suite offers a true retreat with spa-inspired marble finishes, an oversized walk-in shower, a jetted soaking tub, and exceptional custom closet space. Additional features include a private elevator, Control4 automation, integrated audio/video/security systems, five HVAC systems, a central vacuum system, and a Generac whole-home generator. A fully finished and expansive basement level serves as a unique and exceptional extension of the home’s living and entertaining space. Designed for both relaxation and recreation, it features a game and arcade room, a full beverage center with a dishwasher, microwave, and Scotsman ice machine, a fitness area with a sauna and steam room, an additional laundry room, a creative storage center, and a private 4K theater with seating for multiple guests. Outdoors, resort-style living awaits with a saltwater pool and spa, a summer kitchen with a custom copper hood, an electric gated entry, landscape lighting, lush cascading bougainvillea, and ten mature magnolia trees creating exceptional beauty and privacy. The property also features a dog run with artificial turf. Three ventless gas fireplaces, including one on the private covered porch, add warmth and ambiance throughout the home. This home also features a whole-house water softener system. Top-rated A+ public schools are within a short walk or bike ride. Nearby highly regarded private schools include Park Maitland School, The Christ School, The First Academy, Trinity Preparatory School, Lake Highland Preparatory School, and Bishop Moore Catholic High School. Perfectly positioned within walking distance of the boutiques and dining of Park Avenue, and just minutes from the Winter Park Golf Course, Rollins College, and Advent Health Winter Park, this is a rare opportunity to own an exceptional custom estate in one of Central Florida’s most sought-after communities.

1571 Woodland Avenue, Winter Park
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