Winter Park Homes with Cathedral Ceiling(s) Interior features

Winter Park Homes with Cathedral Ceiling(s) Interior features

Welcome to Winter Park, Florida—a picturesque city renowned for its enchanting landscapes, vibrant arts scene, and historic charm. Nestled just north of Orlando, Winter Park is a haven for those who appreciate a blend of natural beauty and urban sophistication. With its tree-lined streets, sparkling lakes, and a delightful array of boutiques and cafes, this community offers a lifestyle that is both relaxed and refined.

One of the standout features of homes in Winter Park is the stunning cathedral ceilings that grace many of the interiors. These soaring ceilings not only create an expansive sense of space but also invite an abundance of natural light, making each room feel airy and open. Imagine entertaining friends or simply enjoying a quiet evening at home beneath the grandeur of these architectural marvels. The combination of high ceilings with thoughtfully designed layouts enhances the overall aesthetic, creating a perfect backdrop for your personal style.

In Winter Park, you’ll find a diverse selection of homes that showcase these impressive cathedral ceilings, from charming bungalows to luxurious estates. Each property offers a unique character while maintaining the city’s signature elegance. Whether you’re drawn to the historic districts or the modern developments, the allure of cathedral ceilings adds a touch of sophistication to your living experience.

Discover the magic of Winter Park, where stunning homes with cathedral ceilings await you. Embrace a lifestyle filled with culture, nature, and the warmth of a close-knit community, all while enjoying the comforts of your dream home.

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

$2,390,000
4 Beds ⋅ 5 Baths ⋅ Villa View Park SubDv. ⋅ 32789 Zip Code
Custom-built Santa Barbara-style estate set on one of Winter Park's most coveted brick-paved streets, just moments from Park Avenue's boutiques, galleries, and celebrated restaurants, Winter Park Golf Course, Winter Park Racquet Club, historic Rollins College, and vibrant Winter Park Village. Built in 2010, this 4BR/4.5BA residence spans 3,661 SF across two floors, with cathedral ceilings, a cozy fireplace, plus colonial windows and French doors which frame the resort-style pool retreat. A gracious main-floor primary suite offers dual vanities and a large walk-in closet. The double island chef's kitchen features a gas range and premium Thermador appliances, anchoring an open-plan living, dining, and kitchen design, modeled for everyday ease and effortless entertaining. A flexible bonus space is ideal for a home office, formal dining, or gym. Upstairs, three additional spacious bedrooms each offer their own en-suite bathroom and walk-in closet. The home wraps around a covered courtyard leading to the heated saltwater pool and spa, creating a private outdoor enclave. Parking is a breeze with an oversized two-car garage, additional golf cart parking plus utility pad. Ample storage and workspace complete the rear of the property, which is also wired for a future whole-home generator. A rare offering in the heart of Winter Park, where timeless design meets an unmatched lifestyle.

645 Pansy Avenue, Winter Park
$569,000
3 Beds ⋅ 3 Baths ⋅ Fairshores Place SubDv. ⋅ 32789 Zip Code
Life in Winter Park is about more than just where you live—it's about how you live. At 2803 Riddle Drive, that lifestyle comes together with an inviting open floor plan, a private full fenced backyard with a pool designed for year-round enjoyment, and a location that's just minutes from everything that makes Winter Park one of Central Florida's most desirable communities. The heart of the home is a bright, open living space where the kitchen, dining, and living areas flow effortlessly together around a wood-burning fireplace. Filled with natural light and designed for connection, it's a space that feels equally suited for lively gatherings, holiday celebrations, or quiet evenings at home. Step outside and discover what truly sets this property apart. A sparkling private pool and a fully fenced quarter-acre yard that creates an outdoor retreat that's increasingly hard to find. Whether you're entertaining friends, watching children or pets play, or simply enjoying a peaceful morning by the pool, this backyard offers the space and privacy to enjoy Florida living the way it was meant to be. Thoughtful updates—including a new roof (2022), HVAC system (2022), fresh interior paint, and updated lighting—provide peace of mind while leaving opportunities for the next owner to make the home uniquely their own. Ideally located just minutes from Park Avenue's dining and boutiques, Lake Killarney, Hillstone, College Park and major commuter routes, this home offers exceptional convenience without sacrificing the character and charm that make Winter Park so special. With a private pool, two-car garage, generous outdoor space, and an open floor plan that truly lives for entertaining, 2803 Riddle Drive offers a rare opportunity to enjoy the Winter Park lifestyle at an exceptional value.

2803 Riddle Drive, Winter Park
$255,000
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
$575,000
3 Beds ⋅ 2 Baths ⋅ Kenilworth Shores Sec 07 SubDv. ⋅ 32792 Zip Code
Welcome to this beautifully maintained and thoughtfully updated home in the desirable City of Winter Park, offering an exceptional blend of comfort, space, and convenience. From the moment you arrive, the freshly installed, vibrant green front lawn and attractive landscaping create an inviting first impression. Inside, the cathedral ceiling enhances the spacious feel of the open floor plan, complemented by luxury vinyl flooring and ceramic tile throughout. The well-appointed kitchen features white cabinetry, granite countertops, and a new stainless steel appliance package that adds a modern touch. The home's versatile layout offers plenty of room for everyday living and entertaining, including a separate family room, a bright Florida Room, and a dedicated office or exercise room equipped with an energy-efficient mini-split system and convenient access to the carport. The inside utility room includes a full-size washer and dryer, as well as a second side-by-side refrigerator for added storage and convenience. The spacious primary bedroom provides a comfortable retreat with a private bath featuring maple cabinetry, ample vanity storage, and a roomy walk-in shower. The guest bath offers a tub/shower combination. Step outside to enjoy the spacious, fully fenced backyard—perfect for relaxing, entertaining, gardening, or enjoying the Florida sunshine. Additional features include a storage shed, sprinkler system supplied by a separate well, and a one-car carport with parking for up to three additional vehicles. Major updates include an AC system replaced in 2017, a new roof and electrical panel in 2019, and replumbing completed in 2019. Best of all, you are walking distance to Winter Park High School and just minutes from local dining, shopping, and everyday conveniences. With its spacious floor plan, flexible living areas, attractive updates, generous outdoor space, and prime Winter Park location, this home is a must-see. Schedule your private showing today! Buyer/buyer's agent to verify all schools and room measurements. Appliances convey as is. Brio Management LLC, Seller, is owned by 2 Florida Licensed Real Estate Brokers.

2010 Summerfield Road, Winter Park
$5,600,000
5 Beds ⋅ 6 Baths ⋅ Maitland Shores First Add SubDv. ⋅ 32789 Zip Code
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
$465,000
3 Beds ⋅ 2 Baths ⋅ Garden Lake Estates Unit 1 SubDv. ⋅ 32792 Zip Code
Welcome to this beautifully maintained 3-bedroom, 2-bathroom home nestled in the highly desirable Winter Park area. Combining comfort, style, and an unbeatable location, this charming residence offers the perfect opportunity for homeowners seeking a move-in-ready property in one of Central Florida's most sought-after communities. Step inside to discover a bright and inviting floor plan designed for both everyday living and entertaining. The well-appointed kitchen features stainless steel appliances, granite countertops, and ample cabinetry, creating a functional and stylish space for preparing meals and gathering with family and friends. The home's well-maintained interior reflects pride of ownership throughout, offering a warm and welcoming atmosphere from the moment you arrive. The spacious living areas and comfortable bedrooms provide plenty of room to relax and unwind, while the thoughtful layout maximizes both comfort and convenience. Whether you're hosting guests, working from home, or simply enjoying a quiet evening in, this home is designed to fit a variety of lifestyles. Located in the heart of Winter Park, you'll enjoy easy access to the area's renowned dining, shopping, parks, and cultural attractions. Spend weekends exploring the boutiques and cafés along Park Avenue, enjoying a scenic boat tour through Winter Park's picturesque lakes, or visiting nearby gardens, museums, and recreational trails. With convenient access to Downtown Orlando, major employers, top-rated schools, and world-famous attractions, this location offers the perfect balance of suburban charm and urban convenience. Don't miss this opportunity to own a well-cared-for home in one of Central Florida's premier neighborhoods. Schedule your private showing today and discover everything this wonderful Winter Park property has to offer!

3641 Hawthorne Lane, 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
$399,000
3 Beds ⋅ 2 Baths ⋅ Eastbrook Sub SubDv. ⋅ 32792 Zip Code
Remodeled pool home located in the highly sought after desirable Winter Park school district. This property has a.27 acre corner lot with room to expand and a pool/spa perfect for relaxing or entertaining guest.Inside the living room features vaulted ceilings that create a bright open feeling and a huge screened in patio for outdoor entertaining. The bathrooms have been beautifully remodeled, there are new windows, new electric outlets throughout, new light fixtures, roof replaced in 2022,kitchen beautifully redone 2020 with new cabinets and Granite counter tops. Additional upgrades throughout the home include new luxury vinyl flooring, new vanity in master bath, new enhanced pool liner, new robot pool vacuum, new garage door house has been painted inside and out. The location is close to shopping, Costco and other stores also located near by. Full Sale, Rollins College and downtown Winter Park to the west and UCF to the East within close proximity. This is a must see. Owner is realtor.Buyer to verify room measurements.

1092 Eastbrook Boulevard, Winter Park
$2,500,000
5 Beds ⋅ 6 Baths ⋅ Osceola Shores Sec 03 SubDv. ⋅ 32789 Zip Code
Sophisticated Lakeside Living in the Heart of Winter Park! Experience the pinnacle of Florida luxury in this meticulously renovated estate, perfectly situated within walking distance of the world-class dining and boutiques of Park Avenue, views of Lake Osceola with easy lake access, with a coveted Winter Park location and top notch schools. This 5-bedroom, 4-full and 2-half-bath pool home residence offers an enviable blend of timeless architecture and modern refinement. The interior has been updated and maintained to the highest standards. The home’s open-concept floor plan is anchored by rich, newer solid wood flooring and elegant plantation shutters throughout. At the heart of the home, the chef’s kitchen is a culinary masterpiece featuring, pristine quartz countertops, high-end stainless steel Bosch appliances, natural gas range, double ovens, and a walk-in pantry. A sophisticated entertainer’s bar area off the kitchen is equipped with a 100+ bottle dual-zone wine cooler, beverage cooler, ice maker, and service sink. This area is open to the kitchen an living areas for easy entertaining or catering. The newly reimagined primary retreat is a spa-like sanctuary, showcasing white marble tile, a frameless glass shower with dual rainfall heads, a deep garden soaking tub, double vanity areas with new quartz counter tops, new mirrors and lighting and a bespoke walk-in closet. The primary walk in closet was just updated with a top of the line shelving and storage system for easy organization. The home's floor plan is thoughtfully designed for flexibility, featuring a second primary suite on the main level. Back upstairs, you will find three additional guest bedrooms and two additional full bathrooms, a versatile bonus/flex room over the garage and a private balcony offering serene lake views. The bonus room has endless possibilities and can be used as a recreation room, movie theatre, exercise room, play room, or in-law/nanny quarters as the second back staircase could be a private entry. Outdoor Oasis & Infrastructure Designed for seamless indoor-outdoor living, the rear grounds feature a covered lanai over looking the pool. The covered lanai offers a living and dining area, a newly built-in outdoor kitchen with a professional grill, and a paver-lined patio surrounding a sparkling pool and gas fire pit gazebo sitting area on the other side of pool area. Plenty of yard space to throw the football, practice soccer skills or throw the frisbee with fido!! Exceptional Features Include: Mechanical Integrity: Roof replaced in 2020; updated A/C systems (2016/2019); Rinnai tankless natural gas water heater, brand new primary bathroom, all bathrooms have been refreshed, recently updated kitchen, newer solid wood floors throughout. Storage & Utility: 3-car garage with extended bays for extra storage, oversized closets throughout, and two convenient staircases. Cozy Accents: 2 fireplaces with one being wood-burning and one gas. Three distinct breakfast/dining areas within the kitchen plus formal dining. This is more than a home; it is an invitation to the quintessential Winter Park lifestyle you have been dreaming of living!

450 Lakewood Drive, Winter Park
$825,000
4 Beds ⋅ 4 Baths ⋅ Meadows At Hawks Crest SubDv. ⋅ 32792 Zip Code
Winter Park - Located in the gated community of Hawks Crest, this 4-bedroom, 3.5-bath home offers 2,589 square feet of well-designed living space on a premium pond-view lot. Built in 2020, the home features a downstairs primary suite, open-concept living area, and a versatile upstairs loft. Additional highlights include a tile roof, modern finishes, a screened-in patio for outdoor living, and access to community amenities. This home combines location, layout, and value in a beautiful Winter Park gated communities.

1131 Wildmeadow Run, Winter Park
$685,000
4 Beds ⋅ 3 Baths ⋅ Lost Creek SubDv. ⋅ 32792 Zip Code
Tucked away on a rare and breathtaking .96-acre homesite, this one-of-a-kind property in Lost Creek offers a setting that feels more like a private nature retreat than a suburban neighborhood. Surrounded by protected wooded conservation land and stretching back to the serene Howell Creek, this home delivers unmatched privacy, beauty, and a daily connection to nature. From the moment you arrive, you’ll notice the peaceful ambiance—towering trees, lush greenery, and the soothing backdrop of untouched landscape. Inside, the home features a spacious and inviting layout with approximately 4 bedrooms and 3 bathrooms, designed for both comfortable living and effortless entertaining. Large windows frame picturesque views of the wooded backdrop, filling the home with natural light and bringing the outdoors in. The kitchen flows seamlessly into the main living areas, while the split floor plan offers privacy for the primary suite, complete with tranquil views of the conservation area. Step outside to your backyard oasis where you can unwind, host gatherings, or simply enjoy the sights and sounds of nature along Howell Creek. Opportunities like this are incredibly rare—nearly an acre of protected land, no rear neighbors, and a location just minutes from everything Winter Park has to offer. Experience the perfect balance of privacy, space, and convenience in this truly special home.

3114 Heartleaf Place, Winter Park
$1,725,000
4 Beds ⋅ 4 Baths ⋅ Lakeview Terrace SubDv. ⋅ 32789 Zip Code
This custom 2014-built Winter Park residence is stretched over a double lot with a backyard resort style retreat yet close to all Winter Park offers. A home with function and flexibility with a separate guest house, office or studio based on your needs. This thoughtfully designed home is sophisticated with casual comfort and showcases four bedrooms, 3.5 baths and nearly 3,800 square feet, downstairs main and additional guest suite, and upstairs includes remaining beds and baths. An inviting foyer welcomes you with volume ceilings, wood floors and a large transom window that allows beautiful natural light in. The family room is spacious with a marble wrap electric fireplace with lighting detail and niche for a flat screen TV. Clear glass doors across the back of the house lead you to the outside covered porch for ease of entertainment. The kitchen is open, light and bright with 42-inch shaker double stack cabinetry, large pantry and great workspace, a peninsula with bar seating as well as an eat-in kitchen area for large gatherings. Stainless appliances, granite counters and creative backsplash round it all out. The oversized laundry room includes an extra refrigerator and a second pantry for added convenience. The dining with tray ceiling, designer fixture and textured wallpaper add to the style of the home as well as dedicated office or flex space. Luxury continues into a primary suite with built-ins, large spa-like bath with sleek finishes, soaking tub, large dual-head shower and spacious walk-in closet. The primary suite overlooks backyard and opens to an outdoor oasis with open-air lanai with generous covered porch to gather or enjoy a night of alfresco dining. State-of-the-art modern resort-style pool with heated spa, sun shelf with fountain feature, a fire feature runs along edge of pool and transforms the backyard into a luxurious tropical oasis particularly at night. Hardscaping elements include pathways trimmed with turf grass, professional landscape lighting that enhances and elevates the home. Don’t wait to tour this special home in the heart of Winter Park, close to the best schools with Lakemont Elementary, Glenridge Middle and Winter Park High. A mile from Park Avenue, close to hospital and walkable to the YMCA, Phelps Park and fantastic restaurants.

1840 Bryan Avenue, Winter Park
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