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Browse All Winter Park FL Single Family Properties for Sale

$1,850,000
4 Beds 4 Baths O6352857 MLS
Under contract-accepting backup offers. Ideally on a quiet residential street just near Park Avenue, this custom-built transitional residence offers the best of Winter Park living, accessible, refined and thoughtfully designed from the ground up. Built in 2018 by Carlos Posada, the home delivers 2,653 square feet of living space across two floors, with an additional 365 square feet walk-up attic, four bedrooms and four full baths. From the moment you enter, the home makes an impression. French clay tile flooring anchors the defined foyer, opening into an expansive great room where Bolivian rosewood built-ins frame a gas fireplace and oversized windows draw the eye toward the pool and lanai beyond. The living, dining and kitchen spaces connect seamlessly, designed for everyday ease and effortless entertaining. The kitchen is equipped for the serious home cook, anchored by a full Thermador appliance package and thoughtfully appointed beyond the expected. The large island integrates a sink, microwave drawer, ice maker and refrigeration drawers alongside generous seating, while a walk-in pantry, concealed outlets and a warming drawer round out a workspace as purposeful as it is refined. Outdoor living is equally deliberate. A covered lanai with fireplace and space for a mounted television flows to an open-air terrace and dedicated grilling area, all overlooking a linear pool with water feature and professionally designed landscaping with evening lighting. Upstairs, the primary suite is positioned at rear of the home for added privacy, with abundant natural light, a generous walk-in closet and an en-suite bath. Two additional bedrooms each offer their en-suite baths and built-in closets. A well-appointed laundry room, along with a linen closet and dedicated storage closet in the hall, complete the second floor. On the main level, a fourth bedroom is finished as a library with custom white oak built-ins and French doors opening to the exterior of the home, offering flexible living or professional workspace. Throughout, Panaget engineered hardwood flooring, decorative crown molding, Sierra Pacific windows and doors, cast stone accents, and integrated stair lighting reflect the home's elevated attention to detail. Additional highlights include a detached two-car garage, extensive storage throughout and an infrastructure designed for future elevator conversion. A rare opportunity to own a newer custom home in one of Winter Park's accessible and beloved neighborhoods.

721 Pansy Avenue, Winter Park

$1,695,000
4 Beds 4 Baths O6375766 MLS
Completed in 2020, this beautifully designed contemporary residence on North Park Avenue offers refined finishes and seamless indoor-outdoor living just minutes from Park Avenue’s famed shopping and restaurant district as well as the vibrant retail and dining of Winter Park Village and Mills50. Positioned on a prominent corner lot with dual access from N Park Ave and N Denning Drive, the home features floor-to-ceiling glass, a wraparound terrace, and a bold two-story façade. The quartz river rock and concrete drive leads to dual frosted glass garage doors, pre-wired for an EV charger. Inside, a dramatic floating staircase is framed by a 17’ window, anchoring the open-concept living space with views of the private backyard. The modern kitchen includes light gray touch-open cabinetry, soft-close drawers, black stainless appliances, and a Calacatta quartz waterfall island. The outdoor space is designed for entertaining, with a covered lanai, expansive marble terrace, and a mini-pebble pool with sun shelf and water features. Lush podocarpus hedging and a masonry wall provide privacy. The first floor offers a dedicated office and full pool bath. Upstairs features four bedrooms with Italian frameless doors and three European-inspired bathrooms. The primary suite includes a custom walk-in closet and private access to the wraparound terrace overlooking the pool. Surrounded by beautiful tree-lined streets ideal for strolling and golf-cart rides to nearby shops, restaurants, and friends’ homes, this property offers the best of the Winter Park lifestyle. The home is also zoned for top-rated Winter Park schools. A rare modern home in one of Winter Park’s most desirable locations. Call today for your private showing.

1903 N Park Avenue, Winter Park

$404,900
3 Beds 2 Baths O6390301 MLS
Under contract-accepting backup offers. Virtually Staged. NOW $404,900! Highest and Best Offers to Be Reviewed Tuesday Morning. Pool Home • No HOA • Paid-Off Solar Panels • Roof (2018) Welcome to this well-maintained 3-bedroom, 2-bathroom home offering approximately 1,770 square feet, a 2-car garage, private pool, Roof (2018), Water Heater (2019), and fully paid-off solar panels for added energy savings. The renovated kitchen features quartz countertops, stainless steel appliances, modern cabinetry, an oversized island with an induction cooktop, and an open layout that flows seamlessly into the main living areas. The spacious Florida Room is one of the home's highlights, featuring soaring wood ceilings, exposed beams, a built-in serving area, and direct access to the pool. It's the perfect space to relax, entertain, enjoy your morning coffee, or watch the big game. The primary suite offers a flexible bonus area that can be used as a reading nook, home office, vanity, workout space, or additional storage. The primary bathroom also provides direct access to the pool. Step outside and enjoy a backyard that's hard to find in many pool homes. In addition to the private pool, you'll still have plenty of green space to enjoy, plus a barbecue connection already in place for outdoor cooking. Whether you're hosting friends, grilling on the weekend, or simply unwinding by the pool after work, this backyard is ready to enjoy. Conveniently located just minutes from Park Avenue, Rollins College, Full Sail University, UCF, shopping, dining, and major highways. Zoned for highly rated Seminole County schools.

3463 Arnel Drive, Winter Park

$994,000
4 Beds 3 Baths NS1087637 MLS
Virtually Staged. NEW CONCRETE CIRCULAR DRIVE AND NEW CONCRETE SIDEWALKS JULY 2026! PRICE IMPROVEMENT! NO HOA! Experience refined living in this renovated custom designed home on a corner lot in one of the area’s most peaceful and private neighborhoods. Tucked away at the end of a quiet dead-end street, this residence offers an exceptional blend of craftsmanship, sophistication, and modern comfort. With soaring 10-foot ceilings throughout and a stately wood-burning fireplace which sets a welcoming feeling in the family room. The fully reimagined chef’s kitchen is a true showpiece, featuring solid maple cabinetry, quartz countertops, programmable Bosch stainless steel range and refrigerator and a striking brick backsplash—an elevated space designed for both culinary creativity and effortless entertaining. All three bathrooms have been luxuriously renovated, and new carpeting adds a soft, refined touch throughout all four bedrooms. French doors from the master suite, formal living room, and family room open to a breathtaking screened-in pool retreat. Surrounded by lush tropical landscaping, this private oasis has been thoughtfully upgraded with a new pool pump, a conversion to a sparkling saltwater system, and a beautifully refinished pool deck. An outdoor shower with both hot and cold water adds a resort-level convenience, perfect after a swim or a day in the sun. Every major system has been meticulously updated for peace of mind, including a new programmable HVAC system, a complete replumb of the entire home, all new ductwork, and an upgraded water heater. Additional enhancements—such as fresh interior and exterior paint, a new garage door opener in the over-sized garage, irrigation system and refreshed landscaping — ensure a truly turnkey experience. With its luxurious finishes and meticulous improvements, this residence is ready for the next family to make it their own. This property is located just 2 miles to AdventHealth Winter Park Hospital, less than 10 minutes to Park Ave, and zoned for top-rated schools: Dommerich Elementary, Maitland Middle, and Winter Park High School. Just minutes from Winter Park’s boutiques, acclaimed restaurants, and the cultural charm of Park Avenue, this home offers a rare opportunity to enjoy elevated living in a setting that’s both secluded and connected. A truly private sanctuary designed for comfort, style, and the best of Florida living.

1800 Magnolia Avenue, Winter Park

$2,385,000
5 Beds 5 Baths O6388606 MLS
Under contract-accepting backup offers. Under Construction. In the heart of Winter Parks highly coveted Tree Streets, where quiet tree-lined roads and timeless charm define the neighborhood, this stunning new construction by LUIH Homes offers a refined blend of modern architecture. The home immediately captivates with its bold contemporary façade and thoughtfully designed floor plan. Inside, elegant living spaces unfold intentionally, beginning with a sophisticated dining room accented by a custom wine bar and wine cooler. The main living room serves as a dramatic focal point of the home, featuring a stunning statement accent wall anchored by a sleek electric fireplace. At the heart of the residence, the chef's kitchen is designed to impress. Outfitted with Calacatta quartz countertops, custom cabinetry, a hidden walk-in pantry, and a full suite of Thermador appliances, the space delivers both performance and beauty. The first-floor primary suite is a true private retreat, thoughtfully positioned for comfort and tranquility. Generous in scale, it features a spa-inspired bathroom with a freestanding soaking tub, dual vanities, an expansive walk-in shower, and a large custom walk-in closet designed for both style and functionality. Also located on the first floor is an additional guest bedroom, providing flexibility for visitors, multi-generational living, or a private office. Upstairs, a spacious loft offers an additional living area perfect for relaxing or gathering, while a cleverly designed hidden homework room adds a unique and practical touch ideal for work or study. Three additional bedrooms complete the upper level, each offering generous proportions and beautifully finished spaces. Outdoors, the home transitions into a private backyard retreat designed for year-round Florida living. A covered lanai with a fully equipped summer kitchen, complete with grill and sink, sets the stage for effortless outdoor entertaining. The expansive backyard features a resort-style pool and spa, surrounded by ample space for lounging, dining, and enjoying the serene setting. The location further elevates this exceptional residence. Nestled within Winter Park's beloved Tree Streets, the home offers the rare combination of quiet neighborhood charm with incredible convenience, just a short walk to Phelps Park, The YMCA, and only minutes from the boutiques, dining, and vibrant lifestyle of Park Avenue. Don't miss this rare opportunity to own a home that truly has it all.

1630 Elm Avenue, Winter Park

$1,199,000
3 Beds 3 Baths O6390504 MLS
This new residence, thoughtfully designed by Michael Wenrich, captures the timeless elegance and refined simplicity reminiscent of the iconic coastal architecture of Alys Beach. Clean architectural lines, graceful curves, and abundant natural light combine to create a home that feels sophisticated and inviting. Inside, gorgeous chevron-patterned wood floors flow throughout the main living areas, setting a warm and elegant tone. The open-concept floor plan is designed for everyday living and effortless entertaining, with expansive windows allowing natural sunlight to pour into every space. At the heart of the home is a beautifully designed kitchen that blends classic style with modern functionality. A stunning quartz waterfall island anchors the space, complemented by custom cabinetry and a suite of high-end appliances including an ILVE induction range with six elements and Café French door refrigerator, dishwasher and microwave. Designer-grade lighting and refined finishes elevate the kitchen into a centerpiece of the home. The dining room is filled with light and character, featuring three sets of French doors that open to a charming private front and side courtyard, an ideal setting for morning coffee or intimate outdoor dining. In the living room, a dramatic wall of sliding glass doors connects the interior to the brick patio and backyard, creating a seamless indoor-outdoor lifestyle. The first-floor primary suite offers a peaceful retreat, complete with a spacious walk-in closet and a spa-inspired bath featuring a large glass-enclosed shower, separate soaking tub and dual vanities. Additional conveniences on the main level include a beautifully appointed powder bath, a dedicated laundry room and a generous storage room tucked neatly beneath the staircase. Upstairs, a versatile loft provides additional living space ideal for a media area, office or lounge. Two additional bedrooms are also on the second floor, each featuring custom built-in closets, beautiful designer lighting and abundant natural light. Built with quality and efficiency in mind, the home includes numerous upgrades such as a slate roof, Trane air-conditioning system, Rheem tankless water heater and a two-car attached garage. Ideally just minutes from the renowned shopping and dining of Park Avenue and charm of downtown Winter Park, this exceptional home also offers convenient access to major roadways, Orlando International Airport, leading hospitals, and top-rated public and private schools, bringing together style, comfort and location in one remarkable new construction opportunity.

1870 Walker Avenue, Winter Park

$918,000
4 Beds 3 Baths O6387812 MLS
Pre-Construction. To be built. This is your final opportunity to build a custom home in one of Winter Park’s most sought-after pockets. Set on a 6,748 sq ft lot, this brand-new 4-bedroom, 3.5-bath residence offers 2,662 sq ft of thoughtfully designed living space, blending clean modern architecture with the comfort and functionality today’s buyers expect. Crisp lines, open-concept living, and intentional design create a home that feels both elevated and livable. What makes this opportunity truly unique: this is the last remaining homesite within a curated collection of three custom builds—each thoughtfully designed with its own architectural identity, yet unified in creating a refined, cohesive streetscape. The other two homes are already underway, making this your only chance to secure a position in this limited offering. Located just 6 minutes from Park Avenue, you’re moments from Winter Park’s best—boutique shopping, award-winning dining, and everyday conveniences—while also being close to top-rated hospitals and major thoroughfares. Offered as a custom build, this home allows you to tailor finishes, selections, and details to match your vision. Pricing reflects the base build, with upgrade options available to create a fully personalized end product. With new construction opportunities in 32789 at this price point becoming increasingly scarce, offerings like this are few and far between—especially with the ability to fully customize your home from the ground up.

Lot #21 Karolina Ave, Winter Park

$3,275,000
4 Beds 6 Baths O6382377 MLS
This exceptional Winter Park residence offers a floor plan rarely found in the area, with nearly all living spaces thoughtfully positioned on a single level for effortless everyday living. Completely rebuilt in 2018 by renowned custom builder Posada Homes, a member of the elite Master Custom Builders Council, the home blends modern design, crisp architectural lines, and timeless elegance across an expansive 0.39-acre lot along one of Winter Park’s most picturesque tree-lined streets. The home immediately captivates with its refined architecture and beautifully manicured grounds. Inside, sunlight streams through expansive windows, illuminating hardwood flooring, intricate millwork, and thoughtfully curated finishes that reflect the craftsmanship of a true custom build. Just off the foyer, a hidden wine room provides a sophisticated surprise, perfect for those who love to entertain. At the center of the home is the chef’s kitchen designed for both beauty and functionality. Outfitted with premium Thermador appliances, sleek quartz countertops, a generous center island, and custom cabinetry, the kitchen flows effortlessly into the expansive great room where high ceilings, designer lighting, and elegant architectural details create an atmosphere that is both inviting and refined. Tucked away for privacy, the primary suite is positioned just off a luxurious family room featuring custom built-ins and a gas fireplace. The primary suite itself is a true sanctuary, complete with a sitting area, private coffee bar, and a spa-inspired bath featuring dual vanities, a soaking tub, and an oversized walk-in shower. Rarely found in Winter Park, all bedrooms are conveniently located on one level, including two primary suites, allowing the home to deliver seamless livability without sacrificing architectural interest or sophistication. Upstairs, a private office, half bath, and bonus room provide the perfect space for work, media, recreation, or relaxation. Outdoors, the home transforms into a private resort-style retreat. A covered lanai overlooks the sparkling pool and expansive grounds, creating the ideal setting for entertaining or quiet evenings at home. Adding even more flexibility, a 252-square-foot detached studio currently functions as a gym but could easily become a summer kitchen cabana, guest retreat, or art studio. Located within walking distance of Park Avenue’s boutiques, restaurants, and cafés, and just moments from Rollins College and the Winter Park Chain of Lakes, this residence embodies luxury living at its finest. Don’t miss this rare opportunity to own one of Winter Park’s most outstanding homes. The current flooring offers a rich look, and for those who prefer a lighter palette, the seller is open to providing a credit toward flooring updates and coordinating the installation of new flooring if desired.

1581 Forest Avenue, Winter Park

$324,000
3 Beds 2 Baths A4685217 MLS
NEW PRICE OFFERING IN EASTBROOK! Significant $15,000 price drop, placing it well below recent neighborhood comparables. Welcome to Winter Park's best-keep secret. Quiet, safe, family-oriented, with almost zero traffic and zero HOA restrictions and fees – Eastbrook is 32792’s hidden gem. This 3-bedroom, 2-bath home provides unmatched market value and instant equity, pairing mid-century charm with a long list of mechanical updates. Aside from the 7-year windows and electrical panels, and an 8-year, thoroughly-serviced and well-maintained AC unit inside and out, the water heater, exterior paint and window blinds are under a year old. PLUS the brand-new ceiling fans, light fixtures, gutter screens, smoke detectors, interior paint - and all conveying appliances in perfect working order - give you a worry-free, move-in-ready home. Now, let’s talk about that massive backyard oasis! Lush mature trees, a “grass-covered” patio, and a large concrete firepit all conspire to provide a perfect spot for entertaining and room for kids and pets to romp. The house's bonus features include a covered carport, huge separate, air-conditioned laundry room, tons of storage space inside and out, and a separate cross-fenced side yard for vehicles and other large items. To round out these stellar amenities, potential buyers will have peace of mind knowing the roof, electrical, and plumbing systems have all been recently inspected and found in tip-top shape! What’s not to love about this adorable, cozy house?

1760 Peruvian Lane, Winter Park

$1,649,000
5 Beds 4 Baths O6384756 MLS
PRICED BELOW APPRAISAL, CUSTOM BAREFOOT BROTHERS HOME IN WINTER PARK. Finding a truly CUSTOM-BUILT home in Winter Park is rare. Finding one built this recently—with this level of craftsmanship, infrastructure, and thoughtful design—is even rarer. Built by Barefoot Brothers in 2014 and thoughtfully designed for an active family that values entertaining, work-from-home flexibility, and elevated everyday living, this exceptional 5-bedroom, 3.5-bath residence (currently configured as 4 bedrooms + dedicated office) offers a level of quality that simply cannot be replicated at this price point. Just minutes from Park Avenue, Audubon Park, dining, shopping, and top Winter Park amenities, the location is as compelling as the home itself. This residence delivers the rare combination of TIMELESS ARCHITECTURE + MODERN CONSTRUCTION. Built using INSULATED CONCRETE FORM (ICF) CONSTRUCTION, the home offers exceptional durability, energy efficiency, and a remarkably quiet interior—creating a true retreat from outside noise and Florida heat. Average summer utility bills are approximately $185/month. The exterior was freshly repainted in 2023, further enhancing the home’s curb appeal and long-term maintenance appeal. The floor plan was intentionally designed for real life. The FIRST-FLOOR PRIMARY SUITE serves as a private retreat with an attached office, custom walk-in closet with hidden under-stair storage, and a spa-like bath featuring dual sinks, marble vanity, freestanding cast iron soaking tub, marble floors, and an oversized walk-in shower with dual shower heads. A separate downstairs office easily functions as a fifth bedroom if desired. At the center of the home, the chef’s kitchen was built to perform as beautifully as it looks with MARBLE COUNTERTOPS, WALNUT ISLAND, GE CAFÉ GAS RANGE, BOSCH DISHWASHER, BRAND-NEW SAMSUNG REFRIGERATOR, and an oversized walk-in pantry/butler’s pantry. The adjacent living room is equally impressive with extensive custom built-ins, gas fireplace, library shelving, surround sound wiring, and French doors opening seamlessly to outdoor entertaining spaces. Designed with entertaining in mind, the outdoor spaces feel like an extension of the home with a spacious river rock patio, covered breezeway with tongue-and-groove ceiling, natural gas hookup for grilling, detached rear-entry two-car garage, circular front drive, and additional rear parking—an uncommon luxury in this highly sought-after location. Upstairs, soaring ceilings frame a large bonus/playroom alongside three additional bedrooms and two baths, including a Jack-and-Jill layout. A climate-controlled attic space under AC offers valuable bonus storage not included in the home’s stated square footage. Additional upgrades include NATURAL GAS (range, fireplace, dryer & grill), TANKLESS WATER HEATERS, CAT 6 ETHERNET WIRING, QUANTUM FIBER READINESS, and LOW-E DOUBLE PANE WINDOWS. Every inch of this home was intentionally designed with longevity, comfort, and function in mind. Try building this level of fully custom home in Winter Park today—on this timeline, with these finishes, this infrastructure, and this location—at this price point. It’s nearly impossible. Homes of this caliber rarely become available, especially PRICED BELOW APPRAISAL. Schedule your private showing and experience firsthand what makes this Winter Park home so exceptional.

2501 Winter Park Road, Winter Park

$6,900,000
6 Beds 7 Baths O6387200 MLS
Rarely does a property of this caliber grace the Winter Park market. Nestled along the coveted Venetian Canal with 95 feet of pristine waterfrontage, this magnificent masonry estate is the pinnacle of refined Florida living — offering 6,396 square feet of meticulously crafted space, a private boathouse, resort-style grounds, and an address mere steps from the best of Park Avenue. From the moment you arrive, the circular driveway, porte-cochère, and motor court signal that something extraordinary awaits. Solid brick construction and lush, manicured landscaping frame a grand entrance that sets the tone for every detail within. Step through the dramatic grand foyer into a home defined by elevated ceilings, rich hardwood floors, and exquisite crown moldings throughout. The formal living and dining rooms offer elegant spaces for entertaining, while a beautifully appointed wine room with stunning glass doors adds an unmistakable touch of sophistication. A chef's kitchen that truly inspires — outfitted with professional WOLF, Sub-Zero, and Miele appliances, dual islands with breathtaking countertops, a prep sink, built-in nugget ice machine, and a butler's hallway with floor-to-ceiling storage — flows effortlessly into the warm and inviting family room (complete with fireplace) and informal dining area. Bright, sun-drenched interiors and French doors open to a spectacular covered outdoor kitchen and a beautifully landscaped turf backyard, where a stunning saltwater pool and spa invite you to unwind in style. The first-floor primary suite is a sanctuary unto itself — featuring a private office, den, or sitting room anchored by a stunning double-sided fireplace, and a spa-caliber en suite with double vanities, jetted soaking tub, walk-in shower, and an oversized custom-built walk-in closet. A true retreat from the world. Upstairs, four generously sized bedrooms offer comfort and privacy for family and guests alike. One bedroom enjoys its own private en suite and a delightful secret bonus room — a magical hideaway perfect for children. Two bedrooms share a beautifully appointed Jack-and-Jill bath, each with its own private vanity area, and the fourth bedroom is spacious and well-served by the hall bath. The pièce de résistance of the upper level is a state-of-the-art home theater, complete with projector and screen, ceiling surround sound speakers, and a built-in dry bar with wine fridge — the ultimate in at-home entertainment. A detached guest casita with a full bath and wet bar provides ideal accommodations for visitors, while a detached three-car garage offers ample space for vehicles and storage. Two laundry rooms — one per floor — add everyday convenience, and custom storage solutions are found throughout. The whole-house Lutron lighting system and full-house generator ensure comfort, security, and seamless living at every turn. And then there is the water. The private boathouse along the Venetian Canal, with 95 feet of serene waterfront, offers a lifestyle that simply cannot be replicated — direct access to Winter Park's legendary chain of lakes, all from your own backyard. Located just a short stroll to the boutiques and dining of Park Avenue, the beauty of Kraft Azalea Gardens, and the Winter Park Racquet Club, this estate offers not just a home — but a way of life that the most discerning buyers have only dreamed of.

1260 Alabama Drive, Winter Park

$2,394,500
5 Beds 7 Baths O6381552 MLS
Exceptional design meets refined luxury in this brand-new architectural masterpiece by DaVinci. This 5 bedroom, 6.5 bath home offers over 4,500 square feet of bright, open living space designed for both comfort and functionality. Enter through your custom glass front door into the foyer leading to your main living area featuring a fireplace and sliding glass walls for indoor-outdoor living. This flows effortlessly into a gorgeous gourmet kitchen with high-end appliances featuring a Wolf range, Sub-Zero refrigerator, Euro-style cabinetry, oversized island, and walk-in pantry. The downstairs primary suite overlooks the pool and includes a spa-like bath with soaking tub and rain showers. An additional ensuite bedroom on the first floor works perfectly as a guest room or office. Upstairs you’ll find a large loft and media area with private balcony, along with three ensuite bedrooms including walk-in closets. Step outside and enjoy year-round living under the covered lanai featuring a summer kitchen overlooking the saltwater pool surrounded by mature landscaping. An outdoor bath adds extra convenience, and the oversized lot provides abundant space to relax, entertain or dine al fresco. This home comes complete with a spacious three-car garage with EV charging. Minutes to Interlachen Country Club, Winter Park Racquet Club, and Park Ave shopping. Don’t miss this beautiful custom modern home in one of Winter Park’s most sought-after neighborhoods! Ask about the new landscaping package, and driveway installation.

2412 Chantilly Avenue, Winter Park

$820,000
5 Beds 3 Baths O6381009 MLS
*Ask about a lender provided credit up to $12,500 on this home!*1927 Eland Avenue is a rare single family home for sale in Winter Park FL 32789, located on a quiet dead end street with no rear neighbors. This Winter Park home features a main residence plus a detached in law suite ADU built in 2022, offering exceptional flexibility for multi generational living, guest accommodations, or rental income potential. The main home offers three bedrooms and two bathrooms with real wood floors, Spanish Colonial architectural details, abundant natural light, and a functional open living layout. The primary bedroom and bathroom offer the opportunity to be expanded, allowing a future owner to customize and enhance the suite to their needs. Interior features include a wood beamed dining room, fireplace, and a built in bar with mini fridge, making this home ideal for entertaining and everyday living. Major updates include a 2015 roof, 2018 windows, and a 2022 HVAC system, providing added peace of mind for buyers seeking an updated home in Winter Park Florida. The detached in law suite cottage includes two bedrooms and one bathroom, along with a modern eat in kitchen featuring white cabinetry, butcher block countertops, and contemporary finishes. The guest house also offers its own laundry area and skylights that enhance the bright, open feel. A private brick paver patio creates a separate outdoor living space exclusively for the ADU. This ADU has the ability to be separately metered from the main house and can have its own independent address if desired. The main home’s outdoor living area includes an outdoor kitchen, brick paver patio, and a private backyard designed for relaxing and gatherings. Conveniently located near Lee Road, State Road 17-92, and Interstate 4, this property provides easy access to Winter Park, Maitland, College Park, and downtown Orlando. Buyers searching for a Winter Park home near Park Avenue, Rollins College, Winter Park Village, Trader Joe’s, SunRail, and the Winter Park Farmers Market will appreciate the central location and walkable lifestyle. This is a rare opportunity to own a versatile single family home with an in law suite ADU in one of the most desirable neighborhoods in Winter Park FL.

1927 Eland Avenue, Winter Park

$7,250,000
5 Beds 6 Baths O6380444 MLS
Under Construction. Opportunities like this rarely present themself, just a eight-minute walk from the iconic shops, restaurants, and cafés of Park Avenue, 40 Palmer represents a rare convergence of architectural significance, uncompromising craftsmanship, and premier Winter Park location. Built by Vimaro Homes, this extraordinary new construction estate is a statement piece that redefines what luxury living looks like in the heart of Winter Park. The exterior architecture is refined yet commanding, with classical influences interpreted through a modern lens, setting the tone for the exceptional level of design and finishes found inside. One of the most remarkable features, and an offering rarely found in Winter Park, is the underground four-car garage. Designed to discreetly accommodate an impressive vehicle collection, the garage is complemented by a striking spiral staircase that rises from the basement through the main living level and continues to the second floor. The family room is nothing short of breathtaking, featuring bespoke millwork with integrated shelving, soft architectural lighting, and a dramatic fireplace wrapped entirely in marble. The kitchen is a culinary showpiece designed for those who expect nothing less than perfection. Calcutta marble countertops cascade across the space, paired with stunning custom cabinetry, and a professional-grade Thermador appliance suite. A dedicated dirty kitchen allows for discreet preparation, while an expansive walk-in pantry ensures effortless hosting and immaculate presentation. The primary bedroom wing features a spa-inspired bathroom finished in rich marble, featuring dual vanities, a freestanding soaking tub and an enormous walk-in closet with a separate washer and dryer. Upstairs, a dedicated laundry room and a spacious secondary living area provide flexibility for family living, guests, or relaxation. The lower level extends the home’s versatility, offering a workshop, dedicated holiday and seasonal storage, and seamless elevator access to the main level of the home. Outdoor living is equally impressive. A large covered exterior lanai with a pool bath and full summer kitchen creates a seamless indoor-outdoor lifestyle, ideal for entertaining year-round. The backyard is truly resort-inspired, featuring a large swimming pool, sunken fire pit, and spa, all set within a private, beautifully secluded outdoor setting. What ultimately sets 40 Palmer apart is not just its design or finishes, but its unmatched combination of luxury and location. Just minutes from Park Ave shopping and restaurants, moments from the famous Winter Park Golf Course, yet privately tucked away, this home offers a lifestyle that is both vibrant and exclusive. A truly rare opportunity to own a part of the exceptional standard of living delivered by Vimaro Homes.

40 Palmer Avenue, Winter Park

$1,799,999
5 Beds 5 Baths O6375415 MLS
Private, gated lakefront living on Bear Gully Lake one of Winter Park’s most desirable spring-fed ski lakes. Set on an expansive 137-acre body of water, this custom residence offers a rare combination of privacy, scale, and true Florida waterfront lifestyle. A circular driveway behind a private gate welcomes you to a thoughtfully renovated home designed to capture sweeping lake views. Bear Gully Lake is spring-fed and open to water vehicles, making it ideal for boating, water skiing, wakeboarding, tubing, fishing, and year-round enjoyment. The lakefront experience is exceptional, featuring a fully equipped dock with power, covered boat lift, and sun deck, perfectly positioned for enjoying stunning sunsets. Outdoor living is a highlight of the property. The expansive lanai and pool area overlook the lake and are ideal for entertaining, complete with a renovated summer kitchen featuring a grill, sink, mini refrigerator, and granite countertops. The oversized backyard provides ample space for gatherings, recreation, and pets. Inside, the home opens to a dramatic great room with vaulted ceilings, a striking stacked-stone feature wall with custom built-ins, and large sliding glass doors that fully retract to create seamless indoor-outdoor living. The space was reimagined during extensive renovations to maximize natural light and lake views. The chef’s kitchen, redesigned by award-winning designer Sandra Agurto of CCI, features all-wood cabinetry, quartz countertops, contemporary backsplash, oversized island with beverage and wine refrigerators, induction cooktop, convection ovens, and a separate full refrigerator and freezer, with abundant custom storage throughout. The primary suite is privately located in its own wing and offers serene lake views, high ceilings, and a spa-style en-suite bath renovated in 2022 with soaking tub, walk-in shower, expansive custom vanity, upgraded lighting, and private water closet with bidet. A large walk-in closet with custom built-ins completes the suite. All bedrooms feature their own bathrooms and walk-in closets, providing exceptional privacy and flexibility, with three full en-suite bedrooms ideal for guests or multigenerational living. Additional flexible spaces include a gym or bonus room suitable for formal living, dining, or a game room. Recent upgrades include a new roof (2018), new hot water heater (2024), fully fenced yard, Russound sound system, updated security system, new pool deck pavers, and a rebuilt dock with Trex decking and updated boat lift components. The home is part of a lake association with no mandatory dues, providing community updates and seasonal events such as the holiday boat parade. Conveniently located near SR-417, UCF, downtown Winter Park, and Trinity Prep, this is a rare opportunity to own a true spring-fed lakefront home on one of Winter Park’s most coveted lakes.

4469 Old Bear Run, Winter Park

$1,595,000
3 Beds 2 Baths O6379697 MLS
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. The existing residence is perfectly livable and has benefited from numerous upgrades, offering flexibility for immediate occupancy while planning a future custom build. The home also presents excellent rental potential. Please note the interior is currently being utilized for storage and does not reflect its full presentation potential, providing an opportunity for cosmetic refresh or personalization. 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

$1,380,000
4 Beds 4 Baths O6377936 MLS
Welcome to 1751 Goodrich Ave, a beautifully designed residence in the heart of Winter Park! This 4-bedroom, 3.5-bath home showcases thoughtful contemporary architecture with 10' ceilings on both floors, and an open-concept layout that effortlessly blends style and function. With large double paned windows throughout, this home is drenched with an abundance of natural light. High-end finishes continue through the home with a level 5 finish on all walls, spray foam insulation, solid-wood doors, designer shades on every window, and custom closet systems. The showstopping chef-inspired kitchen was designed to entertain with an expansive island, seating 6, and premium finishes- including custom cabinetry, quartz countertops, soft close cabinets and drawers, a concealed Bosh dishwasher, a 48" Thermidor 6-burner gas range, and a Viking Refrigerator. The kitchen seamlessly flows into the living room and dinning space, and also offers easy access for indoor/outdoor entertaining with the telescoping sliding glass door. Outside, you will find the extended patio with plenty of room for hosting friends and family under the bistro-lighting while cooking at the summer kitchen (grill, fridge, range hood). Back inside, you will find a laundry room, half bathroom, and downstairs bedroom with an ensuite offering flexibility to the first floor. Upstairs, you are greeted with a small loft space, 2 bedrooms with a Jack-and-Jill bathroom, and an exquisite primary suite. The primary suite is a true retreat with a large balcony, his and her walk-in closets, and a spacious primary ensuite, featuring a beautiful soaking tub, designer tile, quartz countertops, and great natural light. All upstairs bedrooms are also equipped with motorized black-out shades. This residence is modern, refined, and impeccably curated, offering elevated indoor-outdoor living just minutes from Park Avenue, AdventHealth Winter Park, Rollins College, museums, dining, shopping, and all that Winter Park has to offer! Reach out to schedule your private tour today.

1751 Goodrich Avenue, Winter Park

$1,449,999
5 Beds 4 Baths O6371649 MLS
BRAND NEW CONSTRUCTION COMPLETED APRIL 2026, MOVE-IN READY. 2-year builders' warranty! This 3,164 sqft home at 1523 Miller Ave, Winter Park, FL 32789 combines modern design, high-end finishes, and an unbeatable central location. Featuring 5 bedrooms, 4 full bathrooms, and a private salt-water pool, the home is designed for both everyday comfort and effortless entertaining. The open L-shaped living, kitchen, and dining area is filled with natural light and anchored by a 4-panel grand pocket slider that fully retracts, opening the entire living space to the covered patio for true indoor-outdoor living. The chef’s kitchen overlooks the main living area and flows seamlessly outside to a fully equipped outdoor kitchen with grill, sink, and fridge, complemented by a spacious seating area and pool—ideal for hosting year-round. Additional highlights include a shingle roof with metal accents, a pergola accenting the front of the garage, and clean architectural lines that elevate the curb appeal. The floor plan offers flexibility with generous bedroom sizes and well-appointed full baths, while the backyard retreat centers around the sparkling salt-water pool. Location is a major advantage—2 minutes to I-4, 4 minutes to Mills Avenue, 5 minutes to Park Avenue, 10 minutes to Downtown Orlando, and approximately 20 minutes to Disney, placing dining, shopping, nightlife, and major employers all within easy reach. A rare opportunity to own a brand-new construction home in one of Winter Park’s most connected neighborhoods.

1523 Miller Avenue, Winter Park

$499,000
4 Beds 2 Baths O6362648 MLS
Under contract-accepting backup offers. PRICE REDUCED!!! ROOF 4 yrs. old, newer A/C, In-ground Pool. Enclosed Patio — a beautifully maintained turnkey home nestled in the heart of Winter Park, one of Central Florida’s most sought-after communities. Surrounded by renowned golf courses, top-rated Seminole County schools, lush parks, and family-friendly neighborhoods, this exceptional residence offers the perfect blend of comfort, convenience, and the elevated Winter Park lifestyle buyers are searching for. This spacious 4-bedroom + office home is completely move-in ready and vacant — just bring your furniture and clothes and start living! From the moment you walk through the front door, you’ll love the bright open-concept layout filled with natural light, updated finishes, granite countertops, modern appliances, and an inviting wood-burning fireplace that creates the perfect family gathering space. Designed for entertaining and Florida living, the oversized Florida room/lanai overlooks a stunning private pool and beautifully landscaped fenced backyard, creating the ultimate indoor-outdoor experience. Whether hosting weekend BBQs, pool parties, holiday gatherings, or simply relaxing after work, this home was built for making memories. Additional highlights include: • 2,092 square feet of living space • 4 bedrooms plus dedicated office/bonus room • Large open kitchen with granite countertops and abundant cabinet space • Spacious primary suite with pool views • Huge covered Florida room perfect for entertaining • Private in-ground pool • Full irrigation system and landscaped yard • Wood-burning fireplace • NO HOA • Attached 2-car garage plus additional parking • Fully fenced backyard for privacy and pets • Move-in ready condition Located in the highly desirable Winter Woods/Lake Howell area, this home is centrally positioned near major highways including SR-417, I-4, Howell Branch Road, and SR-436, making commuting to Downtown Orlando, Winter Park Village, UCF, Orlando International Airport, beaches, shopping, dining, and all Central Florida attractions incredibly convenient. Winter Park is known for its charm, tree-lined streets, upscale dining, boutique shopping, beautiful golf communities, and strong sense of community. Families love the area for its excellent schools, nearby parks, recreational amenities, and safe neighborhood atmosphere. This is more than just a home — it’s a lifestyle opportunity in one of Florida’s premier communities.

2217 Sussex Road, Winter Park

$2,195,000
5 Beds 4 Baths O6359471 MLS
Located in highly desirable Lugano Terrace just steps from the shores of Lake Knowles, this stunning all new interiors, 5-bedroom, 3.5-bath brick home effortlessly blends timeless charm with extensive modern updates. Set on a beautifully oversized landscaped lot with a roundabout driveway. Winter Park’s most sought-after neighborhoods adjacent to the Vias, Winter Park Racquet Club and Dommerich Elementary. Inside, wide-plank engineered white pine flooring flows throughout, complementing vaulted ceilings, wood-burning fireplace in the living room, and a spacious open layout ideal for entertaining. The informal dining room overlooks the private backyard and resurfaced PebbleTec pool, while the chef’s kitchen impresses with dual islands, quartz countertops and full-height quartz backsplash, custom hood, Thermador appliances including a 48” six-burner gas range and French door refrigerator. The gorgeous, light filled family room showcases gas fireplace and a built-in bar with wine fridge. The expansive upstairs primary suite is a luxurious retreat, featuring a spa-like bath with a dual-entry shower with Infrared sauna, soaking tub, dual vanities with LED mirrors, expanded closets, and a sitting area. Also upstairs is a flexible loft or library space, an office/nursery with a private balcony, and a bonus exercise room or third closet. Three spacious bedrooms are located downstairs, including a second primary or guest suite with its own en-suite bath and pool access. Notable upgrades include a new roof (2021), PEX plumbing and water heater (2025), updated electrical panels, new propane tank, new AC supply grills and a new second AC system (2025). Additional features include Level 4 smooth drywall, custom trim and moldings, 8’ metal front and double back doors, custom wood interior doors, upgraded light switches and plugs, all-new designer light fixtures ( Regina Andrew, Visual Comfort, etc. ), fireplace surrounds, and custom metal and wood staircase. Black interior and exterior Anderson windows: Dual Pane Low-E Smart Sun Standard Argon Fill Simulated Divided Light (SDL). Outside, enjoy a fully fenced and gated backyard with turf and paver landscaping, updated pool coping, and a covered porch ideal for entertaining, new exterior paint and gas lanterns. The 2-car garage includes custom paneled doors, painted floor and workshop area. Located within walking distance to top-rated Dommerich Elementary, Maitland Middle, and Winter Park High, and just minutes from Park Avenue and the Winter Park Racquet Club and Interlachen Country Club, this home offers exceptional quality, location, and lifestyle. NEW April 2026 Black Steel doors windows with low e-dual pane glass ($150k value!).

1885 Temple Drive, Winter Park

$630,000
5 Beds 3 Baths S5137596 MLS
SELLER MOTIVATED!! Potential of an extra one percent for closing costs, just ask your agent!! Come view this NEXTGEN Home FULLY MODERNIZED 5-bedroom, 3-bathroom home offering flexibility, and comfort that Includes an Attached 2 Bed/1 Bath IN- LAW SUITE!! Step inside to an open and airy layout featuring Luxury plank flooring, fresh neutral paint, and large windows that fill the home with natural light. The upgraded kitchen is a true showstopper — boasting shaker cabinets, quartz countertops, subway tile backsplash, and stainless steel appliances with stylish hardware accents. Located just a 10 minute walk to Lake Killarney and a 3 minute walk to Killarney Elementary School! What is even more fantastic is the distance to I-4 is literally just 2 minutes away for fast and convenient travel to and from downtown Orlando and just 10 minutes from Park Avenue Winter Park!! So many restaurants, parks, local shops and family activities, Especially during the holidays!! Come see this home with potential income and your own private 3/2 as well. This home includes a versatile 2-bedroom, 1-bath in-law suite with its own private entrance, perfect for extended family, guests, or rental potential. Enjoy extra living space in the spacious Florida room, ideal for entertaining, relaxing, or creating the perfect indoor-outdoor flow. With its thoughtful upgrades and multi-generational layout, this home blends functionality with timeless design — truly move-in ready and waiting for you to make it your own!

2612 Roxbury Road, Winter Park

$6,495,000
5 Beds 7 Baths O6349188 MLS
Exquisite new construction with 5 Bedrooms 6.5 Baths and a 3 car garage, in the Heart of Winter Park perfectly positioned on an oversized lot just steps from Park Avenue’s renowned shops, fine dining, and the iconic Winter Park 9-hole golf course, this extraordinary custom residence is a showcase of timeless design and modern luxury. Conceived by acclaimed architect Dan Delong of Origins Residential Design and brought to life by Sean Wulff of Native Homes, every detail has been thoughtfully curated to impress even the most discerning buyer. The expansive floor plan encompasses 5 bedrooms, 6 full baths, and 1 half bath, blending sophistication and comfort across multiple living spaces. Highlights include a dramatic great room, inviting family room, private study, downstairs guest suite, a full bar featuring a 56-bottle wine refrigerator, and an upstairs game room ideal for both everyday living and elegant entertaining. A grand entry reveals the great room with soaring floor-to-ceiling windows and elegant Italian porcelain tile, all overlooking the serene pool and patio. The chef’s kitchen seamlessly connects to the family room and features Canadian-crafted European-style cabinetry, Wolf, Sub-Zero & Fisher & Paykel appliances (dual ovens, dual dishwashers, built-in coffee maker, wine cooler, and beverage center), quartzite countertops, a large island with bar seating, hidden walk-in pantry, plus whole house water softener and filtration systems for premium convenience. The first-floor primary suite is a true retreat with spa-inspired amenities and a custom-built walk-in closet complete with cabinetry and a spacious island. Also on the main level: a private guest suite and dedicated home office/study. Upstairs, a generous game room and three additional en suite bedrooms provide comfort and privacy for family and guests alike. Designed for seamless indoor-outdoor living, the residence boasts two covered lanais finished in Turkish Marble, disappearing screens, a summer kitchen with Urban Bonfire Cabinetry, refrigerator, and ice maker, along with a freestanding fire pit and lush tropical landscaping. The saltwater pool with sun shelf and heated gas spa ensures year-round enjoyment. Built to the highest standards, the home features R-14 block walls with core 500 insulation, open cell foam insulation in attic, Andersen windows, a flat concrete tile roof, and tongue-and-groove ceilings on all lanais. Additional luxuries include: Select European white oak wood floors and Italian porcelain flooring throughout 12’ ceilings on the main level, 10’ ceilings upstairs Cutting-edge construction for efficiency and durability

550 Palmer Avenue, Winter Park

$1,389,500
4 Beds 5 Baths O6354269 MLS
GORGEOUS NEW CONSTRUCTION IN WINTER PARK! Discover sophisticated modern living at 607 Ellen Drive — a brand-new construction masterpiece by the acclaimed Lazarus Homes, perfectly positioned in the heart of Winter Park. At this new price, it's simply unmatched value for new construction in this location. This impeccably designed 2,812-square-foot residence showcases striking contemporary architecture with clean lines, soaring ceilings, and natural light pouring in from every angle. The open floor plan flows effortlessly from space to space, creating the ultimate backdrop for everyday living and unforgettable entertaining. The chef's kitchen is nothing short of a showstopper — outfitted with top-of-the-line Monogram appliances, a sleek Ruvati sink, built-in oven and microwave, and a professional gas range. Show-stopping Taj Mahal Quartzite countertops bring both drama and durability, and you'll have the flexibility to add a full-height wine refrigerator or extra cabinetry to make the space truly your own. The living room delivers modern warmth with an electric fireplace and walls of glass sliders that open wide to a covered lanai and your own private pool — Florida indoor-outdoor living at its absolute best. Love to entertain? The home comes pre-stubbed for an optional outdoor kitchen, ready when you are. Retreat to the luxurious first-floor primary suite, a true private sanctuary with a spa-inspired en suite bath — double sink vanity, walk-in shower, soaking tub, and an oversized walk-in closet with custom built-ins and washer/dryer hookups. Upstairs, the impressive layout continues with a spacious bonus room, a striking loft framed in glass walls, three more bedrooms, two full baths, and a second laundry area for effortless convenience. A dedicated pool bath rounds things out for easy poolside enjoyment. Tucked into the sought-after Lake Killarney Shores community, this home is the ultimate blend of peaceful retreat and unbeatable location. Enjoy a low HOA, private boat launch access to Lake Killarney, and a walkable stroll to Winter Park's best restaurants, boutiques, and cultural hotspots. New construction, lake access, unbeatable location, and a brand-new price — this move-in-ready modern luxury home won't last long!

607 Ellen Drive, Winter Park

$3,650,000
5 Beds 5 Baths O6337304 MLS
Under Construction. Step into a world where the timeless charm of Old Winter Park meets the pinnacle of modern luxury designed by Winter Park Design and masterfully crafted by renowned builder Vimaro Homes. Nestled on one of Winter Park’s most coveted tree-lined streets, this stately home immediately commands attention with its double-entry driveway, framed by manicured landscaping and a sense of grandeur like no other. Inside, the home unfolds across more than 3,600 square feet of impeccably designed living space, with every room telling a story of quality, craftsmanship, and comfort. Rich herringbone hardwood floors stretch throughout the residence, complemented by bespoke millwork, and soaring ceilings. At the core of the home, the designer chef’s kitchen is a true showpiece, crafted for culinary excellence and effortless entertaining. Outfitted with top-of-the-line stainless steel appliances, custom cabinetry with designer hardware, and striking quartz countertops, the space is as functional as it is beautiful. A large island provides a natural gathering place, while an adjacent walk-in pantry offers seamless storage and prep. The primary suite is a retreat unto itself; a serene oasis tucked away for ultimate privacy. The spa-inspired en-suite bathroom rivals the finest resorts, featuring a soaking tub, walk-in shower with rainfall fixtures, designer lighting, dual vanities with custom cabinetry, and luxurious stone finishes throughout. A large, custom walk-in closet completes this elegant retreat. Beyond the main living areas, this home offers unique and thoughtfully designed spaces that elevate everyday living including a dedicated home office, a spacious loft, and a grand 3rd floor bonus room. Outdoors, a resort-style pool, covered lanai, and fully equipped summer kitchen create a private haven for year-round entertaining under the Florida sun. For the car enthusiast, this home offers a perfect fusion of elegance and functionality with a stately porte-cochere, a detached garage connected to the home by a breezeway, and an expansive motor court ideal for guest parking or showcasing a prized collection. Every element of this home speaks to impeccable taste and thoughtful design, from the curated finishes and luxury fixtures to the breathtaking architecture and designer lighting. Located just moments from Park Avenue, Rollins College, and Winter Park’s finest shopping and dining, you are truly in the heart of it all. More than a residence, this is a rare architectural masterpiece by Vimaro offering an unmatched lifestyle in the heart of one of Central Florida’s most coveted neighborhoods.

207 E Kings Way, Winter Park

$3,235,000
5 Beds 6 Baths O6345085 MLS
This stunning new contemporary residence, a five-bedroom, five-and-a-half bath home by the renowned Rex-Tibbs Development, a custom builder for over 40 years, continues to set the standard for luxury living. Perfectly situated on a premium, quiet, charming brick street, the home blends clean architectural lines with timeless finishes and thoughtful design details. An elegant foyer immediately introduces the home’s refined aesthetic, offering a direct line of sight to the gorgeous herringbone white oak floors in the great room and the sparkling pool just beyond the full glass doors. Anchored by a sleek linear gas fireplace with custom built-ins and floating shelves, the great room provides an inviting yet sophisticated gathering space. The open-concept chef’s kitchen is a showpiece in both form and function. Outfitted with Wolf and Sub-Zero appliances, it boasts an eight-burner range with one-and-a-half ovens, an oversized Sub-Zero French door refrigerator with a freezer drawer, a built-in microwave drawer, and a walk-in pantry featuring a wine and beverage tower. Marble counters in all baths continue the home’s commitment to refined finishes. The main level primary suite is a serene retreat with a spa-inspired bath featuring a large glass-enclosed shower, separate soaking tub framed by dramatic four-by-ten-foot porcelain slabs, a custom walk-in closet, and a private water closet. A flexible fifth bedroom with an ensuite bath offers the perfect option for an office or den. A striking glass-railed staircase leads to the second level, where a spacious lounge area opens to a private covered patio. Three additional ensuite bedrooms, each with custom closet systems, complete the upstairs living quarters. Designed for indoor-outdoor living, the expansive covered lanai includes a summer kitchen with a grill, hood vent, refrigerator, sink, and a dedicated half bath. Overlooking lush landscaping with tropical Clusia hedges and Foxtail palms, the brand-new pool is finished with designer tile that lends a stylish, resort-quality flair. Additional highlights include a spacious storage closet under the staircase, oversized two-car garage, 500-gallon propane tank for easy generator connection, stone paver driveway and durable metal roof. Wonderfully located in a picturesque neighborhood, the property is just minutes from the boutiques and dining of Park Avenue, top-rated public and private schools and offers convenient access to downtown Orlando, the attractions, as well as area airports. A rare opportunity to own a newly constructed home of such quality and craftsmanship in one of Winter Park’s most sought-after neighborhoods.

1821 Englewood Road, Winter Park

$640,000
3 Beds 3 Baths O6329628 MLS
Charming Pool Home in Prime Winter Park Location Welcome to 2758 Banchory Road — a true gem nestled in the heart of the desirable Winter Park Pines community. This beautifully maintained 3-bedroom, 2-bath ranch-style home offers the ideal combination of comfort, privacy, and location. With a private swimming pool, lush landscaping, and no direct front neighbors on a quiet cul-de-sac street, this home is perfect for families or anyone seeking tranquility just minutes from city conveniences. Property Highlights Spacious backyard featuring a private pool—perfect for Florida living and entertaining. Fully fenced yard with a storage shed and dedicated area for pets or gardening. Open-concept layout with natural light, mature trees, and charming curb appeal. Located steps from the Cady Way Trail, ideal for biking, jogging, or weekend strolls. Unbeatable Location Just minutes to Downtown Winter Park with boutiques, restaurants, Rollins College, and Park Avenue. Close to Winter Pines Golf Club, Cady Way Park, and public tennis courts. Easy access to Baldwin Park, Full Sail University, Advent Health Winter Park, and the 417 expressway. Top-Rated School Zone Located within the Orange County Public Schools district, this home is zoned for: Aloma Elementary School (PK–5) ~ 0.7 miles Glenridge Middle School (6–8) ~ 1.6 miles Winter Park High School (9–12) ~ 0.6 miles Highly rated with International Baccalaureate (IB) and Advanced Placement (AP) programs Private schools nearby include Trinity Prep, Geneva School, Chesterton Academy, and St. Margaret Mary K–8. Why You’ll Love It Relax and entertain year-round with your private pool and covered patio. Walkable to trails and parks, bikeable to schools, and 10 minutes to Park Avenue. Family-friendly neighborhood with strong community feel and no HOA. A rare combination of location, schools, and lifestyle opportunities. Solar panel included. Whether you’re relocating, downsizing, or looking for the perfect place to raise a family, this Winter Park beauty has it all. Schedule your private tour today!

2758 Banchory Road, Winter Park

$1,390,000
4 Beds 5 Baths O6325192 MLS
Under contract-accepting backup offers. MOVE-IN READY! Construction Completed! Brand-new custom construction on coveted Lakeview Avenue marries classic Winter Park charm with crisp, contemporary living. Behind its inviting façade you’ll find an airy two-story layout featuring four bedrooms and 4 ½ baths, including a full en-suite guest retreat on the main level. Three additional bedrooms share the upper floor with a bright loft that easily flexes as a playroom, office, or second lounge. The heart of the home is a chef-ready kitchen outfitted for serious cooking—double wall ovens, a dedicated cooktop, and generous countertop space—anchored by a spacious walk-in pantry and a convenient mudroom drop zone to keep daily life organized. Just beyond, a soaring great room centers on a built-in fireplace, while wide sliders open to a covered rear porch perfect for year-round alfresco dining. Upstairs, every bedroom enjoys direct or semi-private bath access, giving the residence the feel of four private suites, and a dedicated laundry room means no hauling baskets downstairs. Practical perks abound: an oversized two-car garage for gear and golf carts, impact-rated construction engineered to the latest Florida wind code, and full pre-wire rough-ins ready for your preferred appliance and lighting packages. All this sits minutes from Park Avenue’s dining and boutique shopping, Rollins College, and Winter Park’s famous chain of lakes. Schedule your private tour and discover the fresh, low-maintenance lifestyle waiting for you in one of Central Florida’s most sought-after neighborhoods. There is a pool company the buyers my call on directly if the buyer requires a pool Mike Inspire Pools

501 Lakeview Avenue, Winter Park

$3,975,000
4 Beds 6 Baths O6321143 MLS
In the heart of Winter Park, 1150 Via Salerno is a newly completed Mediterranean-minimalist residence that blends architectural refinement with organic warmth. Now offered at a compelling new price, the home presents a rare opportunity to experience architecturally distinctive new construction in the Vias neighborhood. Conceived, developed & designed by Steve & Jodie Konold of Scout & Co., the 3,850-sf residence offers 4 beds & 5.5 baths, w/ a layout thoughtfully arranged to provide the intentional privacy of a luxury retreat. Beyond its terraced walkway—envisioned in collaboration w/ architect Cynde Norris—French antique gates open to a native-planted entry garden, creating a soft transition to the interior. A glass foyer featuring a woven rattan chandelier, sourced & designed in London, leads to a sculptural stairwell positioned just off the main living spaces. The great room includes soaring ceilings, a sleek, custom plaster fireplace & walls of glass doors & windows. Ten-inch baseboards meet level 5 drywall in a clean reveal, paired w/ micro-crete flooring on the main level & wide-plank European oak upstairs. The kitchen is appointed w/ a Thermador dual-fuel range, matching plaster hood, full refrigerator & freezer columns & a large island with seating topped in honed black quartzite. The surrounding cabinetry features hand-carved V-groove panels w/ soft-close hardware & integrated pullout storage. Caesarstone surfaces line the perimeter while steel-and-glass open shelving w/ a sculptural black sconce balances the composition. A vintage chandelier from Prize Home & Garden sourced in Round Top completes the room. The main floor primary suite is accessed through antique doors that open to a light-filled gallery overlooking the rear courtyard & pool. The primary bath features an extended vanity w/ dual sinks, matte black fixtures, a freestanding tub, walk-in shower w/ built-in bench & separate water closet. On the mezzanine level, the powder bath makes a dramatic statement w/ a floating black quartzite trough sink paired w/ a handwoven mirror. Across the hall, the laundry room blends beauty w/ utility w/ custom cabinetry, matching quartzite surfaces, matte black fixtures & a side-by-side front-load washer & dryer. A nearby bedroom suite is marked by an antique door entry. Each guest bedroom features an en-suite bath introduced by a hand-painted tile threshold, complemented by designer lighting, distinctive mirrors & continuous European oak flooring. The rooftop terrace is accessed from the second-floor hallway. The detached casita opens to the pool courtyard through accordion glass doors on two walls & includes a woven rattan chandelier & a full bath—ideal as a studio, gym or office. Other outdoor spaces include 2 garden courtyards, a heated saltwater pool & a newly constructed outdoor kitchen designed to accommodate a built-in grill & Big Green Egg. A spacious gravel courtyard is ideal for dining or relaxing and is enveloped by mature bamboo that creates exceptional privacy. Additional features include a lower-level two-car garage, storage closet, 3 HVAC systems, Rinnai tankless water heater, Sierra Pacific windows, customized closets, solid core doors, 6” round gutters & a Barcelona barrel tile roof. Thoughtfully designed & beautifully executed, 1150 Via Salerno offers a refined lifestyle within one of Winter Park’s most exclusive enclaves.

1150 Via Salerno, Winter Park

$1,050,000
3 Beds 2 Baths O6250417 MLS
Experience lakeside living in Winter Park, FL with this custom LAKEFRONT PROPERTY on the shores of Lake Killarney, a 234 acre PRIVATE LAKE. There are a limited number of lakefront properties within the City, especially on skiable lakes, so this home presents a unique opportunity. Boasting an EXPANSIVE DOCK, one that’s grander than current building standards allow (but is grandfathered in), this backyard provides an ideal place to launch your water adventures, soak up scenic sunsets, and travel by lake to Hillstone for a meal. The CUSTOM POOL is waiting to be enjoyed! It features a custom waterfall, grotto, built-in seating/table and adjacent koi pond, all with a lake view. Recent updates to the home include: shingled roof (2018), DOUBLE PANE WINDOWS (2015), and HVAC (2016). Travertine and tile floors cover the entire home, there is no carpet. The back family room has multiple French doors and offers an expansive view of the lake. Fireplaces are featured in both the office and living room. The convenience of 632 Country Club is unmatched. It is approximately .6 miles from grocery shopping like Whole Foods and Publix or the Winter Park Village - a vast outdoor mall featuring a 20-screen Regal Cinema, Ruth's Chris Steakhouse and Bar Italia, to name a few. For everyday errands like HomeGoods, or workouts at LA Fitness, there is an even closer shopping plaza. An Interstate 4 (I-4) onramp is approximately 2 miles away. Winter Park is bursting with Old Florida charm and was named #38 historic world destinations in 2008 by National Geographic Magazine. At its heart is Park Avenue, famed for its cobblestoned and tree-lined streets with over 140 boutiques, museums, a train station, and world-class dining. 632 Country Club is approximately 1.5 miles from luxurious Park Avenue and 5 miles from downtown Orlando.

632 Country Club Drive, Winter Park

$562,000
4 Beds 3 Baths O6137445 MLS
Under contract-accepting backup offers. NO HOA. Dual Master Suites. One main, and one mother-in-law or guest suite. All single story, no stairs. NEW POOL DECK. NEW POOL PUMP. POOL RESURFACED.NEW ROOF (installation in progress). Totally renovated. NEW HOT WATER HEATER. NEW FLOORS. POOL RESURFACED. NEW POOL DECK. NEW POOL PUMP. NEW ALL TURF BACK LAWN (NO Mowing). NEW PUTTING GREEN (for your backyard golfer). Full Security system. Get ready to relax & have fun enjoying your new home!! Accessible and convenient, with a fabulous all-turf backyard to unwind, entertain, or make fantastic memories with those you love. Your deepwater private pool (that used to have a diving board) is the highlight of this sunny Florida oasis, including a Mini-golf putting green, outdoor dining, and plenty of space to lounge and relax when you're not on the go. Just 14 miles (30 mins) from Orlando International Airport. 20 mins to the Amway Center, Exploria Stadium, and the Dr. Philips Performing Arts Center for MLS soccer games, concerts, conferences, ballet, theater, NBA basketball games, and more. With both the University of Central Florida (UCF) and Valencia Campuses at similar proximity, this property is close to everywhere you want to be. Take the dogs for a walk around Lake Baldwin, just south, or enjoy the beachside dog park there. Ideal for a brisk run, a rejuvenating bike ride, or an invigorating rollerblade the Cady Way Train connects to the Lake Baldwin path, so you can expand your adventurous outings an additional 13 miles, beyond the 2.5 miles that wrap around the quaint peaceful lake. Baldwin Park is the best place to gather or getaway on your day-to-day. Visit the Winter Park Farmers Markets every Saturday, and take a stroll up Park Ave or take a world-class boat tour of the Winter Park Chain of Lakes after a fantastic Sunday Brunch at any of the local restaurants you know and love. Whether you're gathered around the dining room table laughing and playing board games after dinner, or cuddled up on the sofa in your open great room, watching the flickering fire on a brisk winter day, or streaming your favorite binge-worthy show, there is plenty of room for you to live your life in the best possible way. The split-floor plan gifts privacy from the master wing located off the kitchen and convenient to the backyard oasis/pool. The ensuite guest bath is a rare treat for company and residents alike. Kissed with glowing natural light in every room, this well-laid-out functional flow makes it easy to enjoy every tranquil moment your new home offers you. Turn these moments into memories and live your best life daily! POOL RESURFACED. TURN-KEY OPTIONAL (furniture optional in separate private purchase). Ring Camera. Security System. Updated/Renovated Bathrooms. Bright. Open. Airy. Comfortable. Welcoming. Fun. Cozy. Entertaining. Easy. Relaxing. Refreshing. Peaceful. Happy. Inviting. Private. Convenient.

5233 Lake Howell Road, Winter Park

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