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$1,849,900
3 Beds ⋅ 4 Baths ⋅ Winter Park Residential SubDv. ⋅ 32789 Zip Code
Discover luxury living in this exquisitely renovated two-story condominium, ideally situated on the third floor of the highly sought-after Douglas Grand in the heart of Winter Park. This elegant three-bedroom, three-and-one-half-bath residence seamlessly blends sophisticated design with everyday comfort. Immediately captivating, the light-filled open floor plan showcases stunning new wide-plank white oak flooring, high ceilings, detailed crown molding, and all-new designer lighting throughout. The chef’s kitchen is a showpiece, featuring crisp white cabinetry, luxurious white quartz countertops, a spacious breakfast bar island, elegant gold hardware, and a built-in desk. A charming breakfast nook offers the perfect setting for morning coffee or casual dining. French doors open to a private enclosed atrium, creating a versatile outdoor retreat ideal for alfresco dining, relaxing, or entertaining guests in style. The expansive living and dining spaces flow effortlessly, while a private first-floor bedroom with en suite bath and walkout balcony provides an ideal space for guests, multigenerational living, or a home office. Upstairs, the primary suite serves as a peaceful sanctuary, complete with an indulgent soaking tub, dual vanities, an oversized walk-in closet, and French doors leading to a large private balcony with sweeping views of Winter Park's iconic Park Avenue—perfect for enjoying sunrise coffee or evening sunsets. A second upstairs en suite bedroom offers its own private bath and generous walk-in closet. Thoughtful features include an upstairs laundry room, a spacious storage closet with potential elevator conversion for future accessibility, and a secure gated garage with two reserved parking spaces. Perfectly positioned in the heart of Winter Park, Douglas Grand places you just steps from Park Avenue, the Winter Park Farmers’ Market, Rollins College, Hannibal Square, Winter Park Golf Course, the Winter Park Tennis Center, Winter Park Village, and an array of renowned dining, shopping, and cultural attractions. Enjoy an unparalleled walkable lifestyle in one of Central Florida's most desirable communities. Notable improvements include an interior renovation (2026), front elevation windows and French doors (2024), interior paint (2024), and HVAC system (2022).

101 S New York Avenue Unit 311, Winter Park
$2,350,000
3 Beds ⋅ 3 Baths ⋅ Landmark Winter Park Condo SubDv. ⋅ 32789 Zip Code
Discover an exceptional opportunity to own a penthouse residence at The Landmark, one of downtown Winter Park's exclusive addresses. Directly along the desired brick streets of Park Avenue, this boutique condominium community consists of only 13 residences and offers an unparalleled blend of privacy, sophistication and accessible convenience. Just outside your door, enjoy acclaimed dining, boutique shopping, art galleries, sidewalk cafés, Central Park and the year-round events that have made Winter Park one of Central Florida's sought-after destinations. Behind The Landmark's secure wrought-iron gates, residents are welcomed into a beautifully landscaped courtyard centered around a timeless fountain and illuminated by dozens of gas lanterns, creating a warm and elegant atmosphere reminiscent of a European enclave. Impeccably maintained and thoughtfully designed, the community provides a peaceful retreat while remaining moments from the vibrant energy of Park Avenue. Residence J occupies a premier penthouse position and is filled with natural light, enhanced by soaring ceilings, expansive windows, and multiple French doors that open to private terraces overlooking Morse Boulevard and the surrounding downtown streetscape. The spacious floor plan is designed for comfortable daily living and effortless entertaining. The living and dining areas are anchored by a gas fireplace and flow seamlessly into the kitchen, where integrated appliances, a gas cooktop, generous workspace, and a charming breakfast area create a functional and inviting gathering space. The primary suite serves as a private sanctuary, featuring dual vanities, separate water closets, an oversized walk-in shower and a custom-designed walk-in closet. Two additional guest bedrooms provide flexibility for family and visitors. One bedroom is connected to a Jack-and-Jill bath, while the third enjoys a private en-suite bath and a Juliet balcony that captures the charm and character of downtown Winter Park from above. Additional amenities include two deeded underground parking spaces, a private climate-controlled storage room, and access to the community's shared outdoor entertaining area, complete with a summer kitchen and courtyard gathering space. Whether enjoyed as a full-time residence or a lock-and-leave retreat, this penthouse offers a rare combination of luxury, security and an unmatched Park Avenue lifestyle in the heart of Winter Park.

140 E Morse Boulevard Unit J, Winter Park
$1,300,000
3 Beds ⋅ 3 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code
Set on a rare double lot in one of Winter Park's most coveted locations, this charming 1940 Craftsman-style residence presents an extraordinary opportunity to enjoy one of Central Florida's most celebrated lifestyles while envisioning the future. Just moments from the Winter Park Chain of Lakes, the boutiques and acclaimed dining of Park Avenue, and the timeless beauty of Rollins College, the property offers a setting that few locations can rival. The existing residence features approximately three bedrooms, two-and-a-half bathrooms, and generously proportioned living spaces filled with warmth and character. Lovingly maintained over the years, the home provides a comfortable foundation for renovation, restoration, or reimagination. Outdoors, a screened pool creates a private retreat for year-round enjoyment, while a detached two-car garage and separate studio shed offer exceptional flexibility for hobbies, creative pursuits, a home office, fitness space, or guest accommodations. What truly distinguishes this offering is the double lot itself. Opportunities of this scale within the heart of Winter Park are increasingly rare, providing the space and flexibility to construct a custom estate tailored to your vision while preserving ample room for outdoor living, gardens, and recreation. Life here extends far beyond the property lines. Enjoy morning walks beneath majestic oak canopies, afternoons on the Chain of Lakes, outdoor concerts, art festivals, sidewalk cafés, and some of Florida's most picturesque streetscapes. Whether renovating the existing residence or creating the home of your dreams, this exceptional property represents a rare chance to secure a legacy homesite in one of the most desirable addresses in Central Florida.

321 Sylvan Boulevard, Winter Park
$5,500,000
4 Beds ⋅ 5 Baths ⋅ Sylvan Park SubDv. ⋅ 32789 Zip Code
Pre-Construction. To be built. This extraordinary lakefront residence on beautiful Lake Sylvan, set on a .37-acre (16,603± square foot) homesite, presents a rare opportunity to own a thoughtfully curated custom home by renowned builder Floridian Custom Homes, brought to life in collaboration with Winter Park Design, Brianna Michelle Interior Design and Signature Landscape. Offering 4,775 heated square feet of expertly crafted living space, this four-bedroom plus office, four-and-one-half-bath home blends timeless architecture, elevated finishes and effortless lakefront living. Designed with an open-concept floor plan ideal for everyday living and entertaining, the home showcases stunning European white oak hardwood flooring throughout all main living areas and bedrooms. The heart of the home is the spectacular chef’s kitchen, featuring two oversized islands, custom-designed wood cabinetry, an expansive walk-in pantry, and a premium Sub-Zero and Wolf appliance package highlighted by a 48-inch, eight-burner range. The private first-floor primary suite serves as a luxurious retreat, complete with an expansive walk-in closet and a spa-inspired bath adorned with marble tile shower walls and flooring. Also on the main level is a versatile office/den with a built-in closet. Upstairs, an expansive media/family room provides additional gathering space, accompanied by a dedicated office and three generously sized secondary bedrooms, each featuring en-suite baths and walk-in closets. The fourth bedroom offers exceptional flexibility and may easily serve as a secondary primary suite, ideal for guests or multigenerational living. Designed to embrace seamless indoor-outdoor living, expansive glass sliders extend from the gathering and dining rooms to a covered lanai overlooking the resort-style custom pool. Retractable screens create a setting for year-round enjoyment, while the fully equipped summer kitchen and generous lounge and dining areas make entertaining effortless. Expertly designed by Signature Landscape, the pool features a sun shelf, LED lighting and elegant travertine limestone decking, all surrounded by lush professional landscaping, Zoysia grass and privacy hedging for a serene outdoor setting. Additional notable features include a Brava slate tile roof and a striking custom glass front entry door, further elevating the home’s exceptional curb appeal. Ideally just minutes from the vibrant shops and dining of Park Avenue, this remarkable residence also offers convenient access to major roadways, leading area hospitals and top private schools, all within an A-rated school district. An exceptional opportunity to enjoy luxury lakefront living in one of Central Florida’s desirable settings.

313 Sylvan Drive, Winter Park
$845,000
3 Beds ⋅ 2 Baths ⋅ Timberlane SubDv. ⋅ 32789 Zip Code
Sold data entry.

2208 Howard Drive, Winter Park
$849,000
3 Beds ⋅ 3 Baths ⋅ Canton Ave Cottages 1 SubDv. ⋅ 32789 Zip Code
Virtually Staged. Nestled in the heart of Winter Park, just blocks from Park Avenue and Winter Park Village, this exceptional residence delivers the walkable lifestyle that defines one of Central Florida’s most coveted communities. Leave the car behind and enjoy easy access to award-winning restaurants, boutique shopping, coffee shops, art galleries, Rollins College, the Winter Park Farmers’ Market, and the Chain of Lakes, all just moments from your front door. Built in 2017 by David Weekley, this thoughtfully designed home combines modern luxury with effortless everyday living. Soaring ceilings, oversized windows, and an open-concept floor plan fill the home with natural light and create an inviting atmosphere throughout. The first-floor primary suite offers a private retreat complete with a spa-inspired bath and spacious walk-in closet, while two additional bedrooms, a full bath, and a dedicated laundry room provide flexibility and convenience. Upstairs, the expansive living and entertaining space serves as the heart of the home. The chef’s kitchen is outfitted with custom cabinetry, granite countertops, premium stainless-steel appliances, a large center island, and a natural gas cooktop—perfect for everything from weeknight dinners to hosting friends and family. Sliding glass doors lead to a spacious balcony with new Trex decking, creating the ideal setting for morning coffee, outdoor dining, or evening cocktails overlooking the neighborhood. With professional landscaping maintained by the HOA, this home offers the ultimate low-maintenance, lock-and-leave lifestyle without sacrificing location or luxury. Opportunities to own in such a highly walkable, centrally located Winter Park setting are exceptionally rare. Experience the convenience, charm, and energy of Park Avenue living while enjoying the privacy and comfort of a beautifully appointed residence. This is Winter Park at its finest.

437 N Capen Avenue, Winter Park
$3,500,000
5 Beds ⋅ 7 Baths ⋅ Kenilworth Shores Sec 06 SubDv. ⋅ 32789 Zip Code
Experience resort-style living at 1836 Whitehall Drive! Inspired by the warm breeze and seaside elegance of a tranquil island paradise, this new custom home by Urban Perch, A Boutique Home Builder, offers a timeless front elevation, exquisite finishes inside and out, and unobstructed views of the beautiful outdoors from almost every room. Totaling 4,168 square feet, this five-bedroom, five-bath residence (and casita!) features a unique U-shaped floor plan ensuring natural light shines through every gathering space. Channeling the natural sands of a sunny retreat, the kitchen features white marble countertops and backsplash with blush pink undertones. A custom plaster hood, La Cornue gas range, a wall of cabinets with paneled GE Monogram appliances and a scullery with additional prep space create a kitchen ideal for entertaining. The marble island overlooks one of the main living rooms, where white oak trim highlights the precast stone surrounding the gas fireplace. A vaulted ceiling with natural wooden beams accentuates the bubble chandelier and level 5 drywall finish. Full-height sliding glass doors invite you to soak in the saltwater pool, summer kitchen, landscaped grounds and detached casita beyond. With accordion-style doors and a side entrance, the casita can serve as a pool house, personal home gym or additional bedroom with full bath. Sightlines from the main entrance lead you to the outdoors but also serve as observation points for the color-drenched first floor bedroom and primary suite with arched entry. A freestanding tub with smart glass window, zero-entry shower and extra thick Taj Mahal quartzite countertops elevate the primary bath to pure relaxation. Outside the primary suite, a concealed under-stairs laundry closet appears elegant, as impeccable millwork provides seamless transitions to the adjacent accent wall. Completing the first floor is a formal living room and dining room, a bold powder room, and a charming mudroom with custom cabinets. Follow the wrought-iron railing and engineered wood flooring to the expansive second floor. A flex room, three additional bedrooms and baths, a large laundry room, and built-in closets and benches keep everything organized and beautiful. This exceptional Winter Park home, crafted with intention and experience from award-winning local custom home builder, Urban Perch, elevates everyday living to approachable luxury.

1836 Whitehall Drive, 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
$1,400,000
4 Beds ⋅ 4 Baths ⋅ Woodmere Terrace Rep SubDv. ⋅ 32789 Zip Code
Welcome to 1220 Woodmere Drive, where timeless elegance and modern luxury come together in one of Winter Park’s most coveted neighborhoods. This exceptional 4-bedroom, 3.5-bath residence offers 2,815 square feet of thoughtfully designed living space, blending classic charm with today’s most desirable comforts. The spacious first-floor primary suite serves as a private retreat, complete with dual walk-in closets and a spa-inspired bath designed for relaxation. Rich solid hardwood floors flow throughout the main downstairs living areas, creating warmth and sophistication at every turn. Upstairs, a smart split-bedroom layout provides three additional bedrooms and two full baths, offering privacy and flexibility for family and guests alike. A detached two-car garage adds even more versatility, featuring an expansive bonus room above—perfect as a home office, fitness studio, creative space, or hobby room. Ideally positioned on one of Winter Park’s most sought-after streets, this home places you just moments from the Winter Park Racquet Club, the scenic Chain of Lakes, and the vibrant shops and dining of downtown Winter Park. With top-rated public schools nearby and an unbeatable location, this is a rare opportunity to enjoy the very best of Winter Park living. 1220 Woodmere Drive isn't just a home—it's a lifestyle.

1220 Woodmere Drive, Winter Park
$1,595,000
Tuscany Terrace SubDv. ⋅ 32789 Zip Code
Exceptional opportunity in the heart of Winter Park - a truly premier and irreplaceable homesite offering rare scale, privacy, and extraordinary future build potential. The primary value is in the land, presenting an unparalleled canvas for a custom luxury residence, with virtually no comparable vacant land available in the immediate vicinity. Set on a tranquil small lake that provides remarkable serenity and picturesque water views, this property combines peaceful natural surroundings with unbeatable walkability. Ideally positioned just steps from the Racquet Club, moments to Park Avenue's renowned dining, boutiques, and cultural venues, and within easy reach of the Winter Park Chain of Lakes. The location also offers the distinct prestige of residing within the coveted "Vias" of Winter Park, a collection of streets long regarded as one of the city's most established and desirable residential enclaves. Whether envisioned as a modern architectural statement or an elegant estate home, this site delivers the location, setting, and versatility sought by discerning builders, investors, and end users alike - a rare chance to secure one of winter Park's most desirable land offerings in a highly established neighborhood.

1113 Via Del Mar, Winter Park
$849,900
3 Beds ⋅ 4 Baths ⋅ Virginia Hgts Rep SubDv. ⋅ 32789 Zip Code
Virtually Staged. Welcome to 1265 Arlington Place, a beautifully appointed townhome nestled in the heart of Winter Park's coveted College Quarter - just steps from Rollins College, Park Avenue, and all the dining, shopping, and culture that downtown Winter Park provides. The main level features an open living area flowing into a well-equipped kitchen with granite countertops and solid wood cabinetry, a wet bar for effortless entertaining, a dining room, and a convenient half bath - all finished with rich hardwood floors. French doors lead to a private, fenced yard with two deck spaces, one covered with an awning, perfect for outdoor entertaining or quiet mornings outside. Also on the main level, the spacious primary suite offers an oversized walk-in closet and direct yard access. The luxurious primary bath features double vanities, a soaking tub, and a separate standing shower. Upstairs, a generous bonus living space is flanked by two additional bedrooms, one of which includes an en-suite bath and two walk-in closets - ideal for guests or a home office setup. A full hall bath completes the upper level. Throughout the home, storage has been thoughtfully considered, with generous closet space at every turn. Smart home features including remote-controlled outdoor lighting, garage door, irrigation, and alarm system make this the ultimate lock-and-leave lifestyle home. Residents also enjoy exclusive access to Virginia Heights Park, a private lakefront park reserved for neighborhood use only - a rare amenity in the heart of Winter Park. Come see what makes this property so special!

1265 Arlington Pl, Winter Park
$470,000
2 Beds ⋅ 1 Baths ⋅ Orwin Manor Westminster SubDv. ⋅ 32789 Zip Code
Under contract-accepting backup offers. Virtually Staged. Located in the heart of Orwin Manor, one of Winter Park’s most beloved historic neighborhoods, 1521 Cavendish Road is a beautifully renovated 2-bedroom, 1-bath home offering 1,042 square feet of thoughtfully updated living space. Positioned between Winter Park, College Park, and Downtown Orlando, residents enjoy convenient access to AdventHealth, Loch Haven Park, the Orlando Museum of Art, Orlando Science Center, Park Avenue, Ivanhoe Village, and some of the area's most celebrated dining, shopping, and cultural destinations. Surrounded by mature landscaping, manicured hedges, colorful garden beds, and stately palms, the home's curb appeal reflects the character and pride of ownership found throughout the neighborhood. French front doors open to a spacious foyer that leads into a bright family and dining room combination, where new pine laminate flooring, crown molding, plantation shutters, and updated lighting blend historic character with modern comfort. The renovated kitchen features shaker cabinetry, Silestone countertops, stainless steel appliances, abundant storage, and natural light. Both bedrooms have been thoughtfully updated with new flooring, LED recessed lighting, ceiling fans, and plantation shutters, while the recently renovated bathroom pairs basketweave tile flooring, subway tile, quartz countertops, and classic finishes that honor the home's original style. Outside, the large backyard has been transformed into a private retreat featuring a composite deck, new fencing, mature palms, raised garden beds, steel-edged landscaping, and a paver walkway. Thoughtfully updated while preserving its architectural charm, this home offers a rare opportunity to enjoy historic character in a neighborhood that continues to benefit from the growth, investment, and enduring appeal of Winter Park and Downtown Orlando. Schedule your private tour today.

1521 Cavendish Rd, Winter Park
$2,150,000
5 Beds ⋅ 5 Baths ⋅ Sylvan Heights SubDv. ⋅ 32789 Zip Code
A striking expression of modern luxury, this brand-new residence offers nearly 3,000 square feet of thoughtfully designed living space in one of Winter Park's most desirable locations. From the moment you step inside, a dramatic two-story foyer and soaring ceilings set the tone for a home that seamlessly blends sophisticated design with everyday comfort. The open-concept living areas are filled with natural light and anchored by a stunning feature wall with a sleek fireplace, creating an inviting space for both intimate gatherings and large-scale entertaining. At the heart of the home, the kitchen showcases a statement island, European-style cabinetry, premium finishes, and quality appliances, while a custom wine display tucked beneath the staircase adds a distinctive architectural touch. Designed with flexibility in mind, the first floor features a private guest suite with en-suite bath, a dedicated home office, and convenient laundry room. Expansive sliding doors open to a fully equipped outdoor kitchen, creating a seamless indoor-outdoor lifestyle perfectly suited to Florida living. Upstairs, the primary suite serves as a private retreat, complete with a custom walk-in closet and spa-inspired bath featuring a freestanding soaking tub, oversized walk-in shower, and elegant finishes throughout. Three additional bedrooms provide exceptional accommodations, including a Jack-and-Jill layout and an additional en-suite bedroom. Ideally positioned just minutes from Park Avenue, residents enjoy effortless access to Winter Park's renowned dining, boutique shopping, cultural attractions, parks, and top-rated schools. Combining exceptional craftsmanship, modern design, and an unbeatable location, this is a rare opportunity to own a brand-new luxury home in the heart of Winter Park.

240 N Phelps Avenue, Winter Park
$622,000
3 Beds ⋅ 3 Baths ⋅ Dubsdread Heights SubDv. ⋅ 32789 Zip Code
Super Location! Close to Urban Bike trail, Winter Park Village, Dubsdread Golf Course, Advent Health. This home was custom built with large white wood window casing, formal dining room with plenty of natural light, 10 foot ceilings, crown molding, 8 ft doors, upgraded tile, 3 sets of French Doors open to back and so much more. Gas fireplace in the family room with high-top bar seating in the kitchen also featuring upgraded granite countertops, stainless steel appliances including a gas range, and plenty of storage space with 42 cabinets. Oversized laundry room with extra storage space. Downstairs also features a spacious half bath with a new countertop.All 3 bedrooms are Upstairs. Bathrooms all have new Quartz counters from recent renovations. All bedrooms come with large closets. 2nd and 3rd bedrooms are connected with "Jack and Jill' bathroom with 2 separate sinks. Master Bathroom has large walk-in shower and separate Jetted Tub.Long driveway provides access to detached oversized garage in the back. Wrought iron fencing in backyard adds to a wonderfully landscaped yard.Nearby is Rollins College, the Charles Hosmer Morse Museum of American Art, Mead Botanical Garden, Albin Polasek Museum and Sculpture Gardens, the Enzian Theater, and so much more.Winter Park is also home to over 70 parks, all home to various events, festivals and celebrations throughout the year.A quick ride to almost anywhere in central Florida, minutes to Downtown Orlando, Winter Park Village, College Park, and Park Ave, 20 min to Disney World, and plenty of shopping and award-winning restaurants just minutes away! Pictures taken January 2024

685 Overspin Drive, Winter Park
$4,950,000
4 Beds ⋅ 7 Baths ⋅ Forest Hills SubDv. ⋅ 32789 Zip Code
Residing among the treelined streets of Winter Park, this stunning, contemporary pool home, designed and built by renowned Phil Kean, truly captures the essence of luxury living. Showcasing his signature aesthetic, the home emphasizes sleek architectural lines, refined finishes, and a seamless connection between indoor and outdoor spaces. Expansive walls of glass flood the interior with natural light and create a striking façade that embodies its contemporary elegance. The main living areas are designed for both entertaining and everyday living. A dramatic two-story living room is anchored by designer furnishings, which extend throughout the home, while the spacious dining area comfortably accommodates large gatherings. The adjacent family room continues the modern aesthetic with a built-in media wall, sleek fireplace, textured design elements, and a triple sliding door connecting the indoor and outdoor spaces. Ready for any caliber of chef, the kitchen boasts Thermador appliances, along with extensive cabinetry and countertop space, soft-close drawers, a waterfall edge island, generously sized pantry, and reverse osmosis water filtration. A private home theater on the main level offers a true cinematic experience with surround sound, custom seating, and blackout shades, along with a stylish wet bar, providing additional space for entertaining. The home’s Crestron automation system is discreetly integrated, allowing full control of lighting, climate, and technology from a single interface. Upstairs, a striking floating staircase leads to a gallery-style landing overlooking the living space below. For those exhausting days, you can instead take a ride on the elevator. The expansive primary suite features a sitting area, a custom closet, and terrace access. The spa-inspired primary bath includes dual rain showers with body sprays, a soaking tub, and dual vanities with elegant finishes. Additional second-floor amenities include a fitness room with steam shower and sauna, an additional en-suite bedroom, one of the two laundry rooms, and access to an upper-level terrace overlooking the landscaped grounds and pool. Two en-suite guest bedrooms are conveniently tucked away on the first floor for maximum privacy. Offering four bedrooms, five full bathrooms, and two half baths, the home delivers both comfort and sophistication at every turn. Thoughtfully integrated automated shades provide effortless privacy, while the advanced air purification systems and whole-home water softener complement the home's advanced smart features. This residence is offered fully furnished with curated Restoration Hardware pieces, including custom-selected furniture, lighting, rugs, and artwork that enhance its cohesive design. Outdoor living is equally impressive, with covered lanai spaces enhanced by automated roll-down screens, designer furnishings, a summer kitchen with gas grill and ventilation, and tranquil poolside views. The property also includes a split, three-car garage with a large driveway protected by a gated entrance. Completing this extraordinary dwelling is its location in the heart of Winter Park. This lakeside residence sits minutes from Park Ave Shopping, Rollins College, AdventHealth, multiple Botanical Gardens and Museums, well-rated grade schools, and highway access. Schedule your private showing today and experience the Winter Park lifestyle firsthand.

231 Chelton Circle, Winter Park
$249,900
2 Beds ⋅ 2 Baths ⋅ Lakeside Manor Apts Condo SubDv. ⋅ 32789 Zip Code
At under $250,000, this renovated 2-bedroom, 2-bath condominium is truly move-in ready. The heart of the home is the custom kitchen (2025), which features soft-close cabinetry with a built-in refrigerator surround, matching energy-efficient appliances, quartzite countertops, white granite sink, and antique brass hardware. Additional updates include vinyl flooring throughout, renovated primary shower (2026) with Italian porcelain tile, tankless water heater (2025), renovated hallway bathroom (2024), fresh interior paint (2026), and a new A/C system (2024), which was most recently serviced in June 2026. Enjoy an exceptional HOA package including water, trash, high-speed internet, cable television (150+ channels), and popular streaming services. Set along scenic Lake Killarney, the community features a private dock, boating and kayaking access, abundant guest parking, and new landscaping, with community paving scheduled for August 2026. Schedule your tour today!

2500 Lee Road Unit 104, 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
$199,900
2 Beds ⋅ 1 Baths ⋅ Lakeside Manor Apts Condo SubDv. ⋅ 32789 Zip Code
**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 2500 Lee Road, Unit 220, in Winter Park, a beautifully maintained condominium offering stylish, low-maintenance living in one of Central Florida's most convenient locations. Inside, the condo features 2 bedrooms and 1 bathroom with a functional layout suited for everyday living. Thoughtfully updated throughout, this unit features a modern kitchen with stainless steel appliances, charcoal quartz countertops, and a spacious island with ample storage. The bathroom has also been updated with contemporary finishes, while the unit's clean, modern design creates an inviting atmosphere throughout. A new A/C installed in 2025 provides added comfort and peace of mind. The floorplan includes comfortable living and dining areas, while the secondary bedroom offers flexibility for guests, a home office, or additional storage. The unit overlooks a beautifully landscaped courtyard and is conveniently located near designated parking. Residents enjoy access to a variety of community amenities, including a clubhouse, pool, laundry facilities, park areas, and dock access on Lake Killarney. The lakefront setting provides a peaceful environment and an opportunity to enjoy the surrounding natural beauty. Located in the heart of Winter Park, the condo is close to shopping, dining, parks, and popular destinations such as Winter Park Village, Park Avenue, College Park, Maitland, and Downtown Orlando. With its desirable community amenities and prime Winter Park location, this move-in-ready condo offers exceptional value and convenience.

2500 Lee Road Unit 220, Winter Park
$1,429,000
5 Beds ⋅ 4 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code
LOCATION LOCATION LOCATION. Discover exceptional new construction in the heart of Winter Park. Completed in 2025, this stunning Mediterranean-inspired residence offers 5 bedrooms, 4 bathrooms, and nearly 2,900 square feet of thoughtfully designed living space. Situated on a charming, tree-lined street, the home combines timeless elegance with modern luxury. The open-concept floor plan features 10-foot ceilings, 8-foot doors, luxury vinyl plank flooring throughout, and an expansive great room with an electric fireplace. The gourmet kitchen is designed to impress with quartz countertops, custom cabinetry, stainless steel appliances, a large center island, and abundant storage. A unique under-stair wine cellar adds character and sophistication, while a first-floor guest suite provides privacy and flexibility. Upstairs, the spacious primary suite overlooks the backyard and pool area and includes a spa-inspired bathroom with dual vanities, a soaking tub, walk-in shower, and generous walk-in closet. Three additional bedrooms comfortable accommodations, including a Jack-and-Jill layout and a private In-suite bedroom. A conveniently located upstairs laundry room completes the second level. Step outside to your private outdoor retreat featuring a beautifully landscaped backyard, sparkling in-ground pool, covered lanai, and summer kitchen with built-in grill—perfect for entertaining year-round. Ideally located just minutes from Winter Park’s renowned shopping, dining, parks, and cultural attractions, this exceptional home offers the rare opportunity to enjoy the benefits of brand-new construction in one of Central Florida’s most sought-after communities. Schedule your private showing today.

1473 Berkshire Avenue, Winter Park
$245,000
1 Beds ⋅ 1 Baths ⋅ Winter Park Gardens Condo SubDv. ⋅ 32789 Zip Code
Bright, beautifully updated 1-bed/1-bath condo with floor-to-ceiling views and a prime walkable location in the heart of Winter Park. The renovated kitchen and bath shine with modern finishes, while expansive windows frame serene, ever-changing views of the lushly landscaped grounds. Set within the sought-after Winter Park Gardens, residents enjoy 8 acres of private tropical gardens, peaceful walking paths, and a resort-style pool — all just steps from Park Avenue's dining, boutiques, and culture. A rare combination of tranquil garden living and unbeatable urban convenience. This is a 55+ community with room for younger owners. Call list agents for details.

700 Melrose Avenue Unit K25, Winter Park
$735,000
3 Beds ⋅ 2 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code
Experience the pinnacle of the Winter Park lifestyle in this enchanting historic cottage, offering an unbeatable, highly walkable location just a 2-minute stroll from the pristine campus of Rollins College, a 4-minute walk to the neighborhood coffee shop, and approximately 11 minutes on foot to the boutique shops, world-class dining, and scenic shores of the Winter Park Chain of Lakes along Park Avenue. Families will secure unparalleled long-term educational value with zoning for highly rated schools including Audubon Park K-8 and Winter Park High School. Stepping inside, the home's authentic character is immediately felt, anchored by beautiful real heart of pine wood flooring that flows seamlessly throughout the entire 1,739-square-foot livable layout. The private primary suite serves as a true retreat, complete with a walk-in closet and a sunlit office/flex space ideal for a remote work setup. The home also features an indoor wood-burning fire pit, adding warmth and character to the living space. Natural gas is available on-site, adding efficiency and flexibility for future upgrades, and the home benefits from a new roof installed in 2023. Situated on a rare, sweeping 9,525-square-foot lot that holds substantial land value on its own, the property offers a massive backyard oasis with ample space for a future pool and endless possibilities for outdoor living. A detached garage provides valuable storage and presents excellent potential for conversion into an accessory dwelling unit (ADU), guest house, home office, or income-producing space, subject to buyer verification and local regulations. Adding even more flexibility, an incredible attic space/storage within the home offers the opportunity to create a unique bonus room, studio, office, or creative retreat. Whether you're seeking a charming historic residence, a highly walkable lifestyle, or a property with exceptional long-term upside, this rare Winter Park offering combines character, location, land value, and future potential in a way that is increasingly difficult to find.

738 S Pennsylvania Avenue, Winter Park
$550,000
3 Beds ⋅ 2 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code
Welcome to 650 Douglas Avenue, a beautifully updated 3-bedroom, 2-bath home ideally situated in one of Winter Park’s most desirable locations. This move-in-ready residence features luxury vinyl plank flooring throughout, quartz countertops, updated bathrooms with upgraded tile, modern lighting and plumbing fixtures, fresh interior paint, and a complete appliance package including washer and dryer. Beyond the home’s tasteful updates, the location truly sets it apart. Enjoy being just minutes from the vibrant shops, restaurants, and community events of Hannibal Square and renowned Park Avenue. Spend weekends exploring Winter Park’s award-winning dining, boutique shopping, farmers markets, museums, and picturesque parks, all just moments from your doorstep. This home offers the perfect combination of modern updates, walkable convenience, and the unmatched Winter Park lifestyle. Schedule your private showing today.

650 Douglas Avenue, Winter Park
$5,125,000
5 Beds ⋅ 6 Baths ⋅ Virginia Heights Rep SubDv. ⋅ 32789 Zip Code
Owner/Agent - Properties of this caliber are exceptionally rare in Winter Park — in a neighborhood defined by its walkability to Park Avenue, top-rated schools, and exclusive deeded access to the Winter Park Chain of Lakes. While new construction continues to emerge throughout Winter Park, few can approach the level of intention, artistry and personal investment found here. Named best custom home in the entire Southeast, this grand award-winning residence was conceived and executed by Master Custom Homebuilder Chris Salhab of Valdara Custom Homes as his own family home. Every element of this home reflects a standard of craftsmanship and care that is immediately felt upon entry and discovered anew in every room. The open-concept floor plan flows effortlessly between interior and exterior living spaces, where a summer kitchen, covered entertaining areas and a signature rain curtain that doubles as an outdoor movie screen create an experience unlike anything else on the market. Intelligent design, smart home integration and refined finishes complete a residence that is as functional as it is extraordinary. Offered with the added benefit of premium lease income through early 2027, this is a rare chance to secure one of Winter Park's finest homes as both a trophy asset and an immediate income-producing investment. Private showings by appointment only.

1221 Richmond Road, Winter Park
$655,000
4 Beds ⋅ 3 Baths ⋅ Orangewood Park SubDv. ⋅ 32789 Zip Code
Just Reduced by $20,000! This is your chance to own a beautifully updated Winter Park home at an even better value. Come see it before it’s gone! Rare opportunity to own on one of the most desirable streets in Audubon Park with a coveted Winter Park address. Just a few blocks from East End Market and surrounded by many of Orlando’s Michelin-recognized restaurants, this location offers an unbeatable combination of walkability, lifestyle, and top-rated schools. Zoned for Audubon Park K-8 and Winter Park High School, you’ll enjoy the best of both worlds: the character and community of Audubon Park with the prestige and convenience of Winter Park. This thoughtfully updated home features a 2024 roof, tankless water heater, new carpet, fresh interior and exterior paint, newer insulation, solid-core interior doors, Rain Bird irrigation with well, Vivint security system with cameras, and an Ecobee smart thermostat. The sunken living room creates a unique space for entertaining (it can provide stadium seating or be a conversation pit), while the detached mother-in-law suite adds flexibility for guests, multigenerational living, or rental income. Tucked away from the noise of Corrine Drive yet only blocks from East End Market, neighborhood parks, coffee shops, and dining, this is a rare chance to own in one of Orlando’s most sought-after neighborhoods. Front door does not convey and will be replaced with a similar refinished wood door prior to closing.

2831 Mulford Avenue, Winter Park
$2,695,000
3 Beds ⋅ 4 Baths ⋅ Town Of Winter Park SubDv. ⋅ 32789 Zip Code
LUXURIOUS LIVING WITH FANTASTIC LOCATION This Winter Park three story townhouse is within walking distance to all the fun amenities of the city- the many restaurants, boutique shops, banks, post office, farmers market, Central Park and Rollins College. Designed by architect Phil Kean and built in 2017 the owners have embellished this townhome with custom millwork and finishes, wood floors, sound system, full house generator and a private elevator to all floors. The first floor has a two car garage with storage lift above, large laundry room/home office and a downstairs guest suite. The second floor features a stylish and comfortable living room with lovely custom ceiling detail and moldings, gas fireplace, a sophisticated powder bath, and a beautiful dining room that opens to an eat-in chef's kitchen with Subzero, Wolfe and Bosch appliances and light Taj Mahal quartzite countertops. The third floor offers the spacious master bedroom and bath and also has the additional guest bedroom suite. Take the elevator to the roof top for great views of the city and here find even more potential space for fun entertaining. If your dream is to own a townhome in the heart of Winter Park, here is a stunning one for you!

413 W Morse Boulevard, Winter Park
$500,000
3 Beds ⋅ 2 Baths ⋅ Winter Park Manor SubDv. ⋅ 32789 Zip Code
One or more photo(s) has been virtually staged. WINTER PARK 32789 in the highly sought-after Dommerich Elementary, Maitland Middle, and Winter Park High school district. This is the kind of home buyers hope to find but rarely do — a beautifully updated mid-century modern with the character of the 1960s and the peace of mind that comes from extensive major improvements already being completed. From the moment you arrive, the oversized 76x133 lot, inviting front porch, and clean curb appeal set the tone. Inside, original terrazzo floors, vaulted ceilings, and a bright open great room create warmth, charm, and livability. French doors open to a screened porch overlooking the spacious backyard. The split-bedroom floor plan features two renovated bathrooms, while the redesigned kitchen offers brand-new appliances, cabinetry, and quartz countertops. A spacious 19x12 family room with tile flooring connects to a large inside laundry room with abundant storage and flexible workspace options. Beyond the visible updates, this home stands apart because so many of the expensive and often-overlooked improvements have already been done, including roof, plumbing re-pipe, electrical updates and full-house rewire, hurricane-impact windows, impact front and rear doors, new mini-split HVAC systems, cast iron drain replacement, interior and exterior paint, and more. A rare opportunity to own a thoughtfully improved home in one of Winter Park’s most desirable locations — with no HOA. WELCOME HOME!

2974 Chantilly Avenue, Winter Park
$2,875,000
3 Beds ⋅ 5 Baths ⋅ Conwill Estates SubDv. ⋅ 32789 Zip Code
Beautifully renovated and thoughtfully designed, this exceptional residence is nestled in the heart of Winter Park’s sought-after Tree Streets neighborhood. Privately behind entry gates, the home welcomes you with a picturesque front courtyard highlighted by a tranquil water feature, setting the tone for the sophisticated living experience that awaits. Expansive walls of glass and disappearing sliders flood the interiors with natural light while creating a seamless connection between indoor and outdoor living spaces, all while maintaining a remarkable sense of privacy. Designed for both everyday living and effortless entertaining, the open-concept floor plan showcases a spectacular custom entertainment bar featuring a stunning stone countertop, handcrafted cabinetry, an ice maker, a wine tower and a beverage cooler. The great room, dining area and kitchen flow together in one expansive space, framed by pocketing glass doors on both sides that open completely to the front courtyard and the rear lanai, pool and backyard beyond. The chef’s kitchen is a true centerpiece, outfitted with an impressive suite of Wi-Fi-enabled Thermador appliances, including a six-burner gas range with a steam oven and warming drawer and an integrated refrigerator with freezer drawers and additional refrigerated storage drawers. Thoughtfully designed for both functionality and style, the kitchen also features an appliance garage, a dedicated coffee bar, custom cabinetry and a large pass-through window that pockets into the wall, providing convenient service access to the covered lanai. A fully equipped secondary kitchen and butler’s pantry offers abundant storage, a built-in oven, a microwave and an additional refrigerator, making entertaining on any scale effortless. Privately situated on the first floor, the luxurious primary suite serves as a peaceful retreat with direct access to the lanai and outdoor living areas. The spa-inspired primary bath features a sculptural stone soaking tub, an oversized shower with multiple rain shower heads and a secluded outdoor patio complete with an open-air shower. A beautifully customized walk-in closet completes the suite. Additional first-floor amenities include a dedicated office, an elegant powder bath, and a unique dog room. A versatile flex space currently utilized as a spa room with laundry offers endless possibilities as a fitness room, expansive mudroom, storage area or wellness retreat, with direct access to one of the garage bays. The second level features a spacious family room along with two generously sized bedroom suites, each offering walk-in closets and private ensuite baths. One of the home's most remarkable features is the expansive rooftop balcony, complete with a gas fireplace and panoramic views overlooking both the front courtyard and backyard. Whether hosting guests or enjoying a quiet evening sunset, this elevated outdoor living space provides an unforgettable setting. Situated on a sprawling half-acre lot, the property offers exceptional outdoor space with room for future expansion or simply enjoying the privacy and beauty of the backyard, pool and lanai. Ideally located just minutes from vibrant Park Avenue, residents enjoy convenient access to Winter Park’s renowned dining, shopping, parks and cultural amenities, while major roadways provide easy commutes to downtown Orlando, Orlando Executive Airport and Orlando International Airport.

1724 Pine Avenue, Winter Park
$3,500,000
4 Beds ⋅ 4 Baths ⋅ Maitland Shores 1st Add SubDv. ⋅ 32789 Zip Code
Virtually Staged. Positioned on a quiet canal, this exceptional property features a covered boat dock with lift, offering effortless access to the renowned Winter Park Chain of Lakes. This home, built by Liberty Development, with 4-bedrooms plus two bonus rooms blends elegance with comfortable everyday living. The main level offers a dedicated office area, formal dining room, and an inviting gathering room with gas fireplace, all flowing seamlessly into the stunning chef’s kitchen. Designed for entertaining, the kitchen features two large islands, exotic granite countertops, under-cabinet lighting, and premium Thermador appliances including a 6-burner gas range with griddle. The walk-in butler’s pantry has a beverage cooler and ice maker adds both style and functionality. The adjoining breakfast area is framed by grand windows overlooking the pool, cabana, and canal. The luxurious downstairs primary suite enjoys tranquil water views and a spa-inspired bath with travertine stone floors, marble counters, custom cabinetry, soaking tub, walk-in shower with steam and generous closet space. Upstairs you’ll find three additional bedrooms and a spacious bonus room, while a separate bonus suite above the garage provides future space for a media room, gym or guest retreat. The interior of the home is highlighted by hardwood floors, plantation shutters, decorative moldings and designer lighting throughout. The outdoor living area is equally impressive. French doors open to a covered porch with classic Old Winter Park brick, leading to a travertine-surrounded pool and private cabana with a wood-burning fireplace. Exterior highlights include a metal roof, durable cement board siding and wooden shutters. Don’t miss this limited opportunity to have immediate and easy access to the coveted Winter Park Chain of Lakes. *Some photos have been virtually staged*

2240 Venetian Way, Winter Park
$215,000
1 Beds ⋅ 1 Baths ⋅ Winter Park Gdns Condo SubDv. ⋅ 32789 Zip Code
Click on virtual tour link. Floor-to-ceiling dazzling views, of sparkling pond, sweepiing oaks, towering cypress trees, and lush gardens — in the center of esteemed Winter Park. This beautifully updated upstairs unit sits within the serene Winter Park Gardens complex, where your views of the shimmering pond and pool anchor a lush sprawling landscape of live oaks draped in Spanish moss, mature manicured gardens, and lighted walkways- perfect for evening strolls. The unit itself has been thoughtfully renovated with brand-new luxury vinyl plank flooring, an open kitchen, updated granite countertops, and a fully renovated bathroom — all combining to deliver exceptional value in one of Central Florida's most coveted zip codes. This is a 55+ community with room for younger owners.

700 Melrose Avenue Unit F 21, Winter Park
$739,000
2 Beds ⋅ 2 Baths ⋅ Park West Condo SubDv. ⋅ 32789 Zip Code
Under contract-accepting backup offers. Enjoy the best of living in this beautifully renovated well maintained 2-bedroom, 2-bath condominium located in the highly desirable gated Park West Condominiums. Perfectly positioned just steps from the renowned Park Avenue, this exceptional residence offers walking distance access to award-winning restaurants, charming boutiques, sidewalk cafés, and the popular weekly farmer’s market. This rare 3rd-floor corner unit which enhances privacy was completely remodeled in 2019 with quality upgrades throughout. The interior features are engineered wood flooring, updated tile, modern ceiling lighting, and a bright open-concept floor plan filled with natural light from expansive sliding glass doors leading to three private walk-out balconies. The redesigned kitchen in 2019 includes new cabinetry, countertops, a complete suite of kitchen appliances, including washer and dryer. Both bathrooms have also been tastefully renovated, creating a clean and contemporary feel throughout the home. Additional improvements include a brand-new HVAC system installed in July 2024, offering peace of mind and energy efficiency for years to come. Spacious bedrooms, generous storage, and seamless indoor-outdoor living make this condo ideal for both everyday living and entertaining. Park West residents enjoy beautifully maintained grounds along with community amenities including a sparkling swimming pool and tennis courts. The community is also conveniently located to Rollins College and Full Sail College. Whether you are searching for a full-time residence or seasonal retreat, this exceptional condo combines timeless Winter Park charm with modern updates and an unbeatable location.

300 Carolina Avenue Unit 301, Winter Park