Winter Park Homes with Private Mailbox Exterior Features

2 Beds ⋅ 2 Baths ⋅ Morseland Sub SubDv. ⋅ 32789 Zip Code

Luxury Meets Timeless Design in the Heart of Winter Park. Welcome to this beautifully renovated 2-bedroom, 2-bath residence where thoughtful design and exceptional craftsmanship come together to create a truly move-in ready home. Located just minutes from the shops and restaurants of Park Avenue, this home offers a rare combination of modern luxury and classic Winter Park charm. The light-filled open floor plan is anchored by a stunning chef's kitchen featuring Taj Mahal quartz countertops, custom cabinetry, premium stainless steel appliances, and a dramatic waterfall island that serves as the centerpiece of the home. Wide-plank wood flooring flows throughout, while recessed lighting, designer fixtures, and carefully selected finishes add warmth and sophistication to every room. The spacious primary suite is designed as a private retreat with custom-built closet systems and a beautifully appointed en-suite bath showcasing dual vanities, designer tile, quartz countertops, and a custom frameless glass shower. The guest bedroom also features custom closet cabinetry and easy access to an equally impressive second bathroom finished with high-end materials and elegant fixtures. From the welcoming covered front porch to the abundance of natural light throughout the home, every detail has been carefully considered to create a space that is both inviting and functional. Whether you're looking for a full-time residence or a low-maintenance luxury home in one of Central Florida's premier communities, this exceptional Winter Park property delivers style, quality, and an unbeatable location.

531 W Swoope Avenue, Winter Park

$4,750,000

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

There are luxury homes, and then there are homes that redefine luxury altogether. Crafted by renowned luxury builder Vimaro Homes, this extraordinary residence is the product of meticulous vision, extraordinary craftsmanship, and an unwavering commitment to quality. Every space has been curated to create one of the most refined and meticulously executed homes to ever come to market in Winter Park. Situated on an expansive 15,000-square-foot homesite in the coveted Park Grove neighborhood, just moments from the boutiques and acclaimed dining of Park Avenue, the home immediately captivates with its striking architectural presence and a sweeping double-entry driveway. Beyond the front doors, a breathtaking foyer unfolds beneath soaring 22-foot ceilings, where an elegant, curved staircase, intricate marble mosaic flooring, oversized windows, and meticulous millwork establish a level of craftsmanship rarely found in today's market. Chevron-pattern engineered hardwood flooring extends throughout, complemented by exquisite natural marble and thoughtfully curated designer finishes at every turn. Designed to impress while remaining effortlessly livable, the grand living room features illuminated tray ceilings, a custom-built entertainment wall, and a sleek electric fireplace. The chef's kitchen is a true showpiece, anchored by dramatic Calacatta Viola marble countertops and backsplash, a complete Thermador appliance suite with paneled refrigerator and freezer, and a stunning ILVE range. An expansive butler's pantry with a second sink, double oven, warming drawer, dishwasher, and abundant preparation space elevates both entertaining and everyday functionality, while formal and casual dining spaces provide the perfect setting for gatherings of any scale. The primary suite is a private sanctuary designed for ultimate comfort, featuring its own coffee bar, an extraordinary custom dressing room. The primary also features a spa-caliber bath appointed with striking marble finishes, a dramatic illuminated walk-in shower, freestanding soaking tub, and Perrin & Rowe fixtures. A first-floor guest suite or dedicated office offers exceptional flexibility, while upstairs, three spacious en-suite bedrooms with walk-in closets are complemented by a hidden bonus room. Pocketing glass doors create a seamless transition to an exceptional outdoor retreat complete with a covered lanai featuring retractable screens, a fully equipped summer kitchen, resort-style pool and spa, expansive backyard, and professionally curated landscaping. Located just minutes from Park Avenue and surrounded by top-rated schools, this residence is more than a luxury home, it is a statement of artistry, craftsmanship, and timeless design that redefines what luxury new construction can be in Winter Park.

1525 Granville Drive, Winter Park

$429,000

4 Beds ⋅ 2 Baths ⋅ Glencoe Sub SubDv. ⋅ 32789 Zip Code

Rare opportunity in Winter Park's 32789! Located on a quiet cul-de-sac in one of Central Florida's most sought-after ZIP codes, this spacious 4-bedroom, 2-bath home offers approximately 2,400 square feet of living space, a brand new roof (2025), water heater (2021), and is situated on a generous lot with no HOA. Whether you're dreaming of creating your forever home, searching for your next renovation project, or looking to add a prime rental property to your portfolio, this is one you won't want to miss. With a little vision and updating, this property can truly shine in a neighborhood where beautifully renovated homes and stunning new construction continue to elevate property values. The location is exceptional—minutes from Park Avenue, Winter Park Village, top-rated schools, Rollins College, AdventHealth, downtown Orlando, and convenient access to I-4 and SR 408. Enjoy some of Central Florida's finest dining, boutique shopping, parks, museums, and entertainment, all just moments from your doorstep. Families will also appreciate Killarney Elementary School is just one street away. With endless possibilities to reimagine, renovate, or invest, opportunities to purchase a home like this seldom come along. If you're looking to build equity, generate rental income, or create the home you've always envisioned, this exceptional property is ready for its next chapter.

2323 Devon Court, Winter Park

$310,000

2 Beds ⋅ 1 Baths ⋅ Dubsdread Heights SubDv. ⋅ 32789 Zip Code

Roof 2018 | HVAC 2020| Set on a deep, tree-canopied lot in one of Winter Park's most desirable established neighborhoods, this charming single-story concrete-block home blends timeless character with everyday convenience. A grand oak shades the front lawn, helping cool the home and lower energy costs, while durable masonry construction, a dimensional-shingle roof, and a full-length driveway leading to a covered carport deliver lasting value and practical, protected parking with an attached workshop & storage room. A generous screened front porch offers a breezy, bug-free spot for morning coffee or evening relaxation before you step inside to a spacious living room featuring gleaming refinished hardwood floors and a wood-burning fireplace framed by a classic white mantel with fluted columns. A large picture window floods the room with natural light, and a graceful curved archway, one of the home's most distinctive architectural details, leads you deeper into the thoughtfully connected floor plan. The kitchen is efficiently designed with cabinetry lining both walls for ample storage, laminate counters, under-cabinet lighting, and a full stainless-steel appliance suite. A double sink offers plenty of room to work and a large window overlooks the lush backyard, with a rear door providing easy access for grilling and entertaining. The adjacent, light-filled dining room offers flexible space that works well for family meals, a home office, or a quiet reading nook. Two comfortable bedrooms feature hardwood floors, ceiling fans with lights, and built-in closets, one with built-in shelving, while the bright corner primary enjoys windows on two walls for excellent light and cross-ventilation. A full bathroom is finished with a tiled tub-and-shower combination, a wood vanity, and a frosted privacy window that brings in daylight while maintaining seclusion. Out back, a large, fully fenced yard framed by mature oaks, palms, and established privacy hedges creates a secluded, park-like retreat with ample room to garden, play, entertain, or add a pool. Just minutes from historic Park Avenue, residents enjoy boutique shopping, award-winning restaurants, sidewalk cafés, museums, and year-round community events, with nearby College Park adding popular dining, breweries, and specialty shops. Outdoor recreation abounds with Dubsdread Golf Course, Mead Botanical Garden, Kraft Azalea Garden, and numerous parks close by, plus easy access to Winter Park's scenic chain of lakes and walking trails, all without requiring waterfront ownership. Commuting is effortless thanks to convenient access to Interstate 4, Fairbanks Avenue, Lee Road, SR 426, and SR 436, providing quick connections throughout Central Florida. Downtown Orlando, the Orlando Health and AdventHealth medical campuses, and major employment centers are all within easy reach. With excellent shopping, grocery stores, entertainment, and cultural attractions nearby, this sought-after location offers the perfect balance of quiet residential living and close proximity to everything Central Florida has to offer. This listing is for a single home and lot at 846 Driver Ave, but the owner would also consider selling the adjacent home next door to the North at 844 Driver Ave. If you are interested in purchasing both homes simultaneously, contact listing agent for more details.

846 Driver Avenue, Winter Park

$1,600,000

4 Beds ⋅ 4 Baths ⋅ Killarney Estates SubDv. ⋅ 32789 Zip Code

This home is an adorable 4 Bed 3.5 Bath Home in the heart of Winter Park. You will feel right at home the moment you step in. lovely kitchen showcases gorgeous cabinets, stainless steel appliances, ample amount of cabinetry and counter space, and a breakfast bar, great for entertaining family and friends. Open floor plan. Home features a separate dining area off the kitchen. Spacious living space and bedrooms. Spend your evenings and weekends relaxing on the beautiful lakefront of Lake Killarney, enjoying the incredible sunsets under the shade of huge cypress trees OR poolside in the private fenced in backyard.

250 Killarney, Winter Park

$2,569,999

5 Beds ⋅ 5 Baths ⋅ Orange Grove Sub SubDv. ⋅ 32789 Zip Code

Under Construction. Experience the very best of Winter Park living with this stunning new construction home, where sophisticated design, luxury finishes, and an incredible location come together on a quiet tree-lined street. Ideally positioned just a short golf cart ride from Park Avenue, the YMCA, and Interlachen Country Club, this home offers the perfect combination of privacy, convenience, and refined Winter Park living. From the moment you step inside, an impressive foyer greets you, showcasing intricate marble mosaic tile that sets the tone for the craftsmanship found throughout. The open-concept floor plan flows effortlessly into the main living spaces, where the spacious living room serves as the centerpiece of the home with elegant archways, custom shelving with LED underlighting, warm wood beam accents, and a stunning stone-wrapped fireplace creating the perfect balance of sophistication and comfort. Designed for both everyday living and entertaining, the dining room features a beautiful dry bar complete with a wine refrigerator, while the chef’s kitchen is truly the heart of the home. Outfitted with Calacatta quartz countertops, a paneled built-in refrigerator, a full suite of Thermador appliances, and a spacious walk-in pantry, every detail has been thoughtfully selected to deliver both style and functionality. The first-floor primary suite provides a private retreat with generous proportions and a spa-inspired bathroom featuring marble mosaic tile, dual vanities, a freestanding soaking tub, an expansive walk-in shower, and a large walk-in closet. A rare additional first-floor guest suite adds incredible flexibility for family and visitors. Upstairs, the home continues to impress with a spacious loft, a conveniently located laundry room, and three additional bedrooms, offering plenty of room for everyone. Step outside and experience your personal outdoor oasis with a spacious covered lanai featuring a full summer kitchen overlooking the sparkling pool and spa. The oversized backyard provides an abundance of green space, creating the perfect setting for relaxing, entertaining, or enjoying time with family. Additional highlights include impact-rated windows and doors, premium finishes throughout, and an unbeatable location surrounded by some of Winter Park’s most desirable amenities. This is a rare opportunity to own a brand-new home combining thoughtful design, exceptional craftsmanship, and one of Central Florida’s most sought-after lifestyles.

1754 Taylor Avenue, Winter Park

$2,549,000

5 Beds ⋅ 5 Baths ⋅ Lake Knowles Terrace Add 02 SubDv. ⋅ 32789 Zip Code

Under Construction. Nestled along a quiet street in Winter Park’s coveted Tree Streets, this stunning coastal farmhouse new build delivers the perfect combination of timeless architecture, luxury finishes, and an unbeatable location. From the moment you arrive, the home captivates with its warm and inviting facade, charming architectural details, and exceptional curb appeal. Step inside to an impressive open layout where natural light, designer finishes, and meticulous craftsmanship set the tone. The spacious living room serves as the heart of the home, showcasing a sleek electric fireplace, custom built-in bookshelves with LED accent lighting, and expansive pocketed glass sliding doors that create a seamless connection to the outdoor living space. The chef’s kitchen is a true centerpiece, beautifully appointed with Taj Mahal countertops, custom cabinetry with LED underlighting, a premium Thermador appliance package, and a hidden walk-in pantry that blends functionality with luxury. Flowing effortlessly from the kitchen, the dining area offers the perfect setting for hosting, complete with a custom dry bar, additional cabinetry, and a dedicated wine fridge. Designed with a highly desirable layout rarely found in Winter Park, the first-floor features both the primary suite and an additional guest suite. The primary retreat offers generous proportions, beautiful natural light, and private sliders opening directly to its own lanai. The spa-inspired bathroom provides a true escape with marble mosaic flooring, dual vanities, and an elegant wet room featuring a spacious walk-in shower and freestanding soaking tub. Completing the suite is an expansive walk-in closet with its own stackable washer and dryer for ultimate convenience. Upstairs, a spacious loft creates an additional living area accompanied by a full laundry room and three generously sized bedrooms, providing flexibility for family, guests, or additional workspace. Step outside and experience Florida living at its finest. The covered lanai is designed for year-round enjoyment with a fully equipped summer kitchen overlooking the sparkling pool and spa, along with additional green space perfect for relaxing or entertaining. Located in the heart of Winter Park’s iconic Tree Streets, this residence offers one of the area’s most desirable lifestyles. Enjoy the ability to walk to Phelps Park while being just minutes from the Winter Park YMCA, Park Avenue’s renowned shopping and dining, and everything that makes this community one of Central Florida’s most sought-after destinations. Don’t miss this rare opportunity to own a brand-new construction residence in Winter Park’s highly coveted Tree Streets!

1823 Sunset Drive, Winter Park

$1,099,000

4 Beds ⋅ 3 Baths ⋅ Northwood Terrace SubDv. ⋅ 32789 Zip Code

Reinvented from the ground up for modern living while honoring its 1953 mid-century modern roots, this 4-bedroom, 3-bath Winter Park home blends authentic MCM character with all-new finishes and systems. An open living, dining, and kitchen core opens to a light-filled sitting area, with white oak floors and designer lighting and ceiling fans throughout. The kitchen stuns with Taj Mahal quartzite counters and KitchenAid stainless appliances. Out back, an expanded patio overlooks a private, fenced yard built for gathering. Everything is new: roof, windows, 200-amp electrical, plumbing with new water heater, HVAC ductwork, and Nest thermostat. Best of all, you can live it on foot: walk to East End Market, Kelly's Homemade Ice Cream, Redlight Redlight, Sushi Lola's, and top-rated Audubon Park K-8. Zoned for Winter Park High, and minutes to Park Avenue and Rollins College. A turnkey classic in one of Winter Park's most established, walkable neighborhoods.

3006 Northwood Boulevard, Winter Park

$1,450,000

4 Beds ⋅ 4 Baths ⋅ Windsong Elizabeths Walk 43/81 SubDv. ⋅ 32789 Zip Code

Welcome to 1421 Chapman Circle, an elegant Spanish-Mediterranean home nestled within the highly coveted Windsong community in the heart of Winter Park. From the moment you arrive, the classic barrel tile roof and timeless architectural character set the tone for what awaits inside — a home with enduring style, gracious proportions, and tremendous potential to be personalized for its next chapter. Spanning over 3,500 square feet, this 4-bedroom, 3.5-bath residence offers a formal, well-appointed layout with soaring high ceilings, rich crown molding, and a thoughtful floor plan designed for both comfortable daily living and effortless entertaining. A dedicated first-floor office provides the ideal work-from-home space, while the separate formal dining room adds an air of sophistication perfect for hosting family and friends. The gourmet kitchen is the heart of the home, featuring granite countertops, premium Thermador appliances, and bartop seating — a space equally suited for casual mornings and lively gatherings. The living room opens through French doors to a generous wrap-around screened patio, seamlessly blending indoor and outdoor living in true Florida fashion. The first-floor primary suite is a private retreat, complete with French door access to the patio, a spacious walk-in closet, and a well-appointed en suite bath featuring a double sink vanity, a separate soaking tub, and a walk-in shower. Upstairs, three generously sized guest bedrooms share a hall bath, and a large bonus room and landing offer flexible space for a playroom, media room, or additional lounge area. A large upstairs utility room and additional walk-in storage beneath the stairs ensure that function is never sacrificed. The home is served by two HVAC units, both dated 2017. Beyond the front door, the Windsong community is nothing short of exceptional. Residents enjoy access to two resort-style pools, a splash pad for the little ones, scenic parks, a fishing dock, and coveted chain-of-lakes access complete with use of a community boat — a lifestyle that truly sets Windsong apart. Zoned for A-rated schools and ideally situated just minutes from the vibrant energy of Baldwin Park, Audubon Park, the Mills District, Downtown Orlando, and all that Winter Park has to offer, this address places you at the center of everything. Whether you're drawn to its classic architecture, its unmatched community amenities, or the incredible opportunity to update and truly make it your own, 1421 Chapman Circle is a rare find in one of Central Florida's most beloved neighborhoods.

1421 Chapman Circle, Winter Park

$199,900

1 Beds ⋅ 1 Baths ⋅ Lake Killarney Condominium Assn Inc. SubDv. ⋅ 32789 Zip Code

**Lakeside Living Meets Urban Convenience in the Heart of Winter Park!** Welcome home to this beautifully updated, turn-key 1-bedroom, 1-bathroom first-floor condominium located in the highly desirable Lake Killarney Condominiums community. Offering the perfect blend of modern interior updates, stress-free maintenance, and an unbeatable location, this unit is an absolute gem for first-time buyers, downsizers, or savvy investors looking to capture the ultimate Winter Park lifestyle. Step inside to an open, inviting living space featuring brand-new, modern Luxury Vinyl Plank (LVP) flooring running seamlessly throughout for a sophisticated look and maximum durability. The kitchen is freshly upgraded with brand-new, gleaming appliances and plenty of counter space. As a coveted first-floor unit, you will enjoy the ultimate convenience of easy, stair-free access, dual private entry points, and a private, screened-in patio perfect for sipping your morning coffee or winding down. One of the standout features of this property is its accessibility. **Great news for buyers shopping with FHA financing: the community is under the limit for single-unit approvals, making this an incredible opportunity to purchase with an FHA loan.** Additionally, the fairly low monthly HOA fee covers water, sewer, trash, pest control, and exterior/grounds maintenance. As a resident of Lake Killarney Condominiums, you will enjoy premium lakeside community amenities: **Sparkling Lakeside Pool** with stunning views over the water. **Private Community Boat Dock & Boat Ramp Access**, ideal for paddleboarding or sunset strolls. **On-site Fitness Room & Laundry Facilities** located steps from your door. **Clubhouse, Shuffleboard Courts, and Picnic Areas** with grills for effortless entertaining. Location is everything, and this address boasts an incredible walkability factor. You are quite literally around the corner from some of Central Florida’s finest dining, shopping, and entertainment: **Walk to Grocery & Dining:** Step next door or take a quick stroll to Trader Joe’s, the iconic Hillstone Restaurant overlooking the lake, and the completely revitalized Winter Park Village, which features a luxury movie theater, boutique shopping, and endless cafes. **Park Avenue District:** Just minutes away is Park Avenue, Winter Park’s historic cobblestone main street, renowned for its upscale boutiques, award-winning sidewalk dining, local art galleries, and the Saturday Farmers Market. **Commuter’s Dream:** The property offers lightning-fast access to Interstate 4 (I-4), putting downtown Orlando, Maitland Center, and major employment hubs just minutes away. The Winter Park SunRail Station is also less than a mile down the road for a stress-free commute. Don't miss out on this rare opportunity to own a fully updated, low-maintenance slice of paradise in one of Winter Park's most vibrant, lakeside neighborhoods. Schedule your private showing today!

151 North Orlando Avenue Unit 142, Winter Park

$1,249,900

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

Pre-Construction. To be built. NEW CONSTRUCTION! Introducing an exquisite new construction home in Winter Park Grove, Winter Park's newest community! This residence is carefully curated by SGC Development, a highly respected local builder known for their dedication to quality and craftsmanship. This residence combines luxury living with the utmost convenience, located within walking distance to Publix and a variety of restaurants, and just minutes from vibrant Park Avenue. This light-filled, open-concept design showcases high-end finishes throughout. The chef’s kitchen is a true centerpiece, featuring premium Bosch appliances, a 36-inch gas range, a built-in coffee bar, and a spacious island with ample storage, creating a perfect culinary haven. The main level includes an ensuite bedroom, ideal for guests or a home office. Upstairs, discover two additional guest bedrooms, along with a luxurious primary suite that boasts a large walk-in closet and a spa-inspired bathroom. A versatile media/bonus room completes the upper level, perfect for entertainment or relaxation. Enjoy seamless outdoor living on the covered lanai with a fully equipped summer kitchen—ideal for gatherings and enjoying the Florida sunshine. Don’t miss this rare opportunity to own a thoughtfully designed home in Winter Park Grove, where modern elegance meets an unbeatable location. Schedule your private showing today! The pictures are of a model home with similar features- you can still customize to suit your needs!

Winter Park

$495,900

3 Beds ⋅ 3 Baths ⋅ Killarney Circle SubDv. ⋅ 32789 Zip Code

Back on market. Previous contract was canceled due to buyer circumstances. Seller is motivated and ready to move forward. Fully renovated and carefully reimagined, this 3 bedroom, 3 bath residence in the heart of Winter Park offers a compelling combination of quality, functionality, and long term value. Designed with intention and attention to detail, the property presents a refreshed, modern interior that is both visually appealing and highly practical for everyday living. The home features a completely updated kitchen with new cabinetry, brand new appliances, and a clean, contemporary design that integrates seamlessly with the main living areas. All bathrooms have been renovated, and new flooring has been installed throughout the home, creating a cohesive and polished environment. The layout has been optimized to provide comfort, flow, and usability, making the space feel open while still maintaining defined living areas. Additional improvements include updated front facing windows that enhance natural light, a new main entry door that strengthens curb appeal, and two A/C units offering efficient and flexible climate control. A detached storage structure adds valuable extra functionality, providing additional space for storage or utility use. Situated on a 0.21-acre lot, the property offers a balanced outdoor area with room for enjoyment, customization, or future enhancements. The lot configuration, which includes a portion of an adjacent lot, provides a sense of added space and flexibility not commonly found in similar properties within the area. Located in a well-established Winter Park neighborhood with consistent demand, the home benefits from convenient access to major roadways, shopping centers, dining, and key destinations. Its positioning makes it attractive for both owner occupants seeking a move-in ready home and investors looking for a well located asset with strong fundamentals. This is a property that delivers on both presentation and practicality an opportunity for buyers who recognize the value of thoughtful renovations, a strategic location and a home that is ready to be enjoyed from day one while maintaining long term upside

525 Ololu Drive, Winter Park

Winter Park Homes with Private Mailbox Exterior Features

Newest Winter Park Homes with Private Mailbox Exterior Features