Homes for Sale Near Maitland Middle in Winter Park - 75 homes

Remarks: Tremendous value in the land. Well cared for vintage Winter Park home that has 3 BEDROOM and two bath rooms. Potential to remodel, improve and expand or simply tear down to build a new custom home. However, this home is move in ready! There is not an HOA. 1343 total square feet and 1186 heated square feet. Newer DUAL-PANE WINDOWS! New HVAC system in NOvember 2025. Home was replumbed in 2024. SEPTIC PUMP OUT, OCT 2025. No carpeting instead there is SOLID FLOORING THROUGHOUT: WOOD PARQUET, TILE, LUXURY VINYL PLANK. The kitchen has been updated with SOLID WOOD KITCHEN CABINETS + GRANITE COUNTER TOPS and newer MATCHING APPLIANCES. The home has INDOOR WASHER/DRYER and a working fireplace. The back yard is FULLY FENCED. Local top rated CITY OF WINTER PARK SCHOOLS. And CITY OF WINTER PARK UTILITIES. The land, the lot have a fantastic upside. BOTH NEXT DOOR (WEST SIDE) AND REAR (NORTH SIDE) NEIGHBORING LOTS HAVE BEEN EMPTY FOR SEVERAL YEARS. This is a great investment and the property itself offers excellent rental income. Think "down the road" value + immediate return value.

Listing is courtesy of: GALLOWAY REAL ESTATE (407-421-9990)

Listing Agent: Sidney Galloway (407-421-9990)

Remarks: Located on a quiet cul-de-sac in the heart of Winter Park, this traditional two-story home offers a functional, well-designed floorplan for both everyday living and entertaining. From the moment you step inside, the home has an inviting warmth that you can immediately feel. The main level features a spacious primary suite along with connected living spaces that flow easily from room to room. The primary suite and family room both feature tall ceilings and an abundance of natural light, creating a bright and inviting wing of the home. The kitchen opens to the casual dining area and family room, creating a central gathering space. French doors from the family room lead to a peaceful, southern-inspired screened patio overlooking a spacious yard on nearly half an acre. At the front of the home, a separate living room provides a quieter setting, while the formal dining room is complemented by a butler’s kitchen for added functionality when hosting. Upstairs includes four additional bedrooms with classic charm, featuring original hardwood floors and generously sized rooms, offering flexibility for guests, family, or office space. Just steps from Park Avenue and the Winter Park 9, this home offers an ideal location with easy access to shopping, dining, and golf.

Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)

Listing Agent: Jennifer King (407-595-3272)

Remarks: Built in 2018, this beautifully designed 4-bedroom, 3.5-bath home offers 2,843 square feet of refined living in a prime Winter Park location, walking distance to Park Avenue and the renowned Winter Park 9 golf course. Thoughtful architectural details set it apart, including shiplap ceilings in the living room and kitchen, decorative ceiling finishes in the bedrooms, and a striking tile staircase wall enhanced by natural light. The open-concept layout centers around a chef’s kitchen with Wolf and Sub-Zero appliances, custom cabinetry, and Kohler fixtures—perfect for everyday living and entertaining. The primary suite features a spa-inspired bath with a marble shower, while secondary baths include Kohler and Rohl fixtures. An upstairs bonus room adds flexible living space. Enjoy a private pool, oversized two-car garage with storage, and an extended driveway for ample guest parking. Additional features include dual Carrier HVAC systems, custom window treatments, and elegant Bevolo gas lanterns that create a warm, upscale presence at night. This home offers a rare combination of style, comfort, and walkable convenience in one of Winter Park’s most desirable areas.

Listing is courtesy of: FLORIDA CAPITAL REALTY (786-953-5870)

Listing Agent: Jacob Theisen (407-908-1735)

Remarks: One or more photo(s) has been virtually staged. This home can be purchased with NO INCOME VERIFICATION needed! Welcome to 720 W Webster Avenue, a beautifully renovated home in the heart of historic Carver Town in Winter Park—one of the most sought-after locations in Central Florida. Just a short walk to downtown Winter Park, this charming residence blends modern updates with timeless character while offering the lifestyle people move here for. This 3-bedroom, 2-bathroom home contains 1,356 square feet of thoughtfully updated living space designed for both comfort and style. From the moment you step inside, you'll notice the clean, modern feel created by zero carpet throughout the entire home, giving every room a fresh, cohesive look while making maintenance simple and practical. At the center of the home is the fully updated kitchen, featuring beautiful granite countertops, ample cabinetry, and a functional layout perfect for everyday living or entertaining guests. The kitchen serves as the heart of the home, separating the spacious living room from the formal dining room, creating a natural flow between gathering spaces while maintaining distinct areas for relaxing and hosting. Both bathrooms have been fully renovated, showcasing modern finishes that complement the home's updated aesthetic. Each bedroom offers comfortable space, natural light, and flexibility for a primary suite, guest room, or home office. Convenience continues with the laundry closet featuring a newer stackable washer and dryer, maximizing space while keeping everyday tasks simple and efficient. Step outside and you'll find a fully fenced backyard, providing privacy and plenty of room for pets, outdoor gatherings, or simply enjoying Florida’s beautiful weather. The property also includes an oversized covered carport, offering generous parking and protection from the elements. For electric vehicle owners, the carport is already equipped with a Tesla charger, making daily charging effortless and future-ready. What truly sets this property apart is its unbeatable location. Situated in historic Carver Town, you're just minutes from the charm and vibrancy of downtown Winter Park. Enjoy easy access to Park Avenue’s award-winning restaurants, boutique shopping, art galleries, and cultural attractions. Spend weekends exploring the Winter Park Farmers Market, taking a scenic boat tour on the Winter Park Chain of Lakes, or strolling through Central Park’s shaded oak-lined paths. Whether you're looking for a primary residence, a stylish Winter Park retreat, or a home close to everything that makes this city special, 720 W Webster Avenue delivers the perfect combination of location, updates, and lifestyle. Opportunities to own a fully renovated home this close to downtown Winter Park are rare. Schedule your private showing today and experience everything this exceptional property and location can provide!

Listing is courtesy of: SERHANT (646-480-7665)

Listing Agent: Vincent Cordaro (631-834-0816)

Remarks: 3 bedrooms PLUS an office (or 4th bedroom) AND a "flex space". Easy access to all of Winter Park, UCF, and south Seminole County from this convenient, central location! If you've been searching for a spacious pool home with plenty of space for playing, entertaining, or even working from home -- you've found it here! When you walk in, you'll appreciate the intuitive flow of living space into the kitchen, with built-in eating space. Off of the kitchen, you'll find a bonus space (perfect for an office or home gym) as well as a large indoor laundry room/mudroom, and the converted garage which is ideal for a playroom or secondary living space. On the other side of the home, 2 secondary bedrooms, an oversized hall bathroom, and a primary with en suite bath. There are additional touches that go a long way, too, including the custom plantation shutters throughout the home and updated countertops in the kitchen. Much of your time will be spent in the backyard, enjoying a fenced in pool, screened porch, new custom shed (2025), and fully fenced yard with turf play area. Systems in the home have been well maintained: roof (2017), HVAC (2017), tankless gas water heater (2018), and brand new electrical updates (2026). The home was also re-plumbed in 2008.

Listing is courtesy of: MILLER GRANT AND COMPANY (407-399-6031)

Listing Agent: Courtney Pelfrey (407-454-0538)

Remarks: Under Construction. One of Winter Park's largest new construction homesites — 13,519 square feet, over a third of an acre — anchors this signature build, a three-story luxury residence on Oneco Avenue where scale, privacy, and architectural distinction rarely coexist at this price point. This home carries the mark of a builder renowned for delivering Winter Park's most trend-setting luxury residences — homes that don't follow the market, they define it. At over 4,500 square feet across three levels, the 5-bedroom, 5.5-bath layout with a three-car garage is finished to a standard rarely found in new construction — every bedroom commanding its own private en suite bath. Main Level — Primary suite with spa-caliber bath and dual walk-in closets. Second en suite bedroom. Kitchen, dining, and great room open seamlessly to a covered rear porch. End-of-street privacy, natural seclusion, and the full depth of an oversized lot. Second Level — Three en suite bedrooms surrounding a generous game loft. A private, self-contained zone for family or guests. Third Level — Air-conditioned bonus loft ready for a theater, fitness studio, or private retreat. The Homesite — End-of-street quiet, resort pool potential, and true backyard privacy on one of Winter Park's most coveted streets. Location — Minutes from Park Avenue, top-rated schools, Rollins College, and Central Florida's finest dining and retail. Signature design. Proven builder. Irreplaceable location. Estimated completion July 2026 — inquire today.

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Ahmad Hassan, Pa (718-641-9358)

Remarks: Welcome to your private slice of paradise, perfectly positioned on a charming brick-lined street in the heart of historic Winter Park. This custom-built estate exudes casual elegance from the moment you step through the grand double door entry, where soaring 12-foot ceilings, rich architectural details, and exceptional craftsmanship immediately set the tone. Thoughtfully designed with a well-balanced and highly functional floor plan, the home offers a seamless blend of formal and informal living spaces ideal for both everyday living and elevated entertaining. At the heart of the home, the pristine chef’s kitchen opens effortlessly to the family room and is outfitted with a built-in Thermador French door refrigerator, custom lighted cabinetry, granite countertops, a six-burner gas range with pot filler, double ovens with warming drawer, and an oversized island designed for gathering. A beautifully appointed butler’s pantry with wine fridge and wet bar creates the perfect transition to the formal dining space. Tucked away for privacy, a dedicated home office or library offers a quiet retreat for work or study. The first-floor primary suite is a true sanctuary, featuring intricate ceiling detail, expansive windows, and private French door access to the outdoor living space. The spa-inspired primary bath includes a jetted tub, dual vanities, and two oversized walk-in closets. Upstairs, three generously sized secondary bedrooms and two additional baths—including a private en suite—provide comfortable accommodations, while a charming Juliet balcony offers picturesque views of the tree-lined street below. Step outside to an exceptional outdoor living experience designed for year-round enjoyment. The covered lanai features a fully equipped summer kitchen with built-in grill, custom copper hood, and beverage fridge for the warmest Florida days. The saltwater pool creates a resort-style setting, surrounded by lush landscaping and enhanced by upgraded lighting and smart technology. This meticulously maintained home has been extensively upgraded, including new HVAC systems for both levels, on-demand water heater, whole-house surge protection, updated LED lighting with dimmer controls, smart home integrations for pool, irrigation, security, and climate, as well as complete interior and exterior repainting with premium finishes. High-end reclaimed maple and beech wood flooring has been installed and is complemented by refined architectural details such as curved archways, custom millwork, and elevated designer fixtures. Additional highlights include a newly created wine room, epoxy-coated garage flooring, central vacuum system, and enhanced exterior features with added awnings and detailed craftsmanship. Situated on a gorgeous lot with added privacy and with garage doors thoughtfully positioned away from the street, this home offers both presence and practicality. Just a short stroll to Lake Mizell and minutes from the renowned dining, shopping, and cultural experiences of Park Avenue, this exceptional property combines timeless design, modern upgrades, and an unbeatable location.

Listing is courtesy of: ORANGE SLICE PROPERTIES (863-632-9765)

Listing Agent: Liz Jones (407-619-6345)

Remarks: Conveniently situated near the Winter Park Country Club, this contemporary masterpiece, built by premier builder Z Properties, offers the ideal mix of style, comfort, and modern living. Completed in 2021, the residence has 4,181 square feet of thoughtfully designed living space, including four bedrooms each with a private ensuite bath and an additional powder room. A 412-square-foot casita with a wet bar and private entrance completes its functionality by providing extra flexibility, perfect for guests, extended family, workspace or workout area. The interiors showcase timeless design with high ceilings, glass walls, and carefully curated finishes. The chef’s kitchen and butler’s pantry pair handcrafted cabinetry and stone surfaces with professional-grade appliances, flowing seamlessly into open living and dining spaces designed for both everyday living and entertaining. Outdoors, a 65-foot lap pool anchors the private backyard retreat, complemented by a covered lanai, marine-grade summer kitchen, fireplace lounge, tree garden and lush landscaping. Solid block construction, advanced state-of-the-art home systems, and a climate-controlled two-car garage with an extended hidden driveway highlight the home’s privacy, quality, and convenience. With a distinct European vibe under canopy trees and cobblestone streets in the desirable Valencia Terrace neighborhood, this home is just moments from Park Avenue’s boutiques, fine dining, Rollins College, the Farmers’ Market, and the Morse Museum. Zoned for top-rated Winter Park schools, it offers both luxury and practicality in one of Central Florida’s most sought-after communities.

Listing is courtesy of: THE REAL ESTATE COLLECTION LLC (407-656-7814)

Listing Agent: Lisa Mahjoub (321-217-9965)

Remarks: Welcome to this beautifully designed and thoughtfully upgraded home that perfectly blends comfort, style, and location. From the moment you step inside, you’ll feel the difference, this is more than a home, it’s an experience. Featuring VAULTED CEILINGS THROUGHOUT, the space feels open, airy, and expansive in a way that’s both inviting and unexpected. Natural light pours in from multiple SKYLIGHTS WITH SOLAR-POWERED BLINDS, creating a warm and uplifting atmosphere from morning to evening while allowing you to set the mood with ease. The heart of the home is the FULLY REMODELED EUROPEAN-INSPIRED KITCHEN, showcasing clean lines, intentional design, and LUXURIOUS CAMBRIA QUARTZ COUNTERTOPS, perfect for both everyday living and entertaining. Enjoy peace of mind with recent upgrades including a 2024 SILENT AMANA AC UNIT, 2025 REFRIGERATOR, 2024 DISHWASHER, and 2023 MICROWAVE, offering modern convenience and efficiency. The home also features DOUBLE PANE WINDOWS, enhancing energy efficiency and comfort year-round, along with ceiling fans in the living room, all bedrooms, and patio for added airflow and ease. Step outside and experience a seamless indoor-outdoor flow, ideal for relaxing or entertaining in your own private retreat. All of this, perfectly positioned in a PRIME LOCATION NEAR SHOPPING, DINING, AND MAJOR HIGHWAYS, while still offering a sense of calm and privacy. This is more than a home… it’s a feeling. Move with Zen. SCHEDULE YOUR SHOWING TODAY!

Listing is courtesy of: ZEN LIVING HOMES LLC (407-800-2717)

Listing Agent: Nydia Marrero (407-620-6221)

Remarks: Under contract-accepting backup offers. Charming Opportunity in Prime Winter Park – 446 Alberta Drive, Winter Park, FL! First time ever on the market and sits on a double lot that is .35 acres. Only a mile stroll to the famous Park Ave shops, dining and entertaining. Home site over looks Lake Osceola and the multi million dollar homes all around!! A neighborhood lot, a few doors down, allows residents to have walking access to Lake Osceola for paddle boarding, fishing, swimming or just to enjoy the view!! This home has only had one owner and is uniquely positioned not to see a next-door neighbor to your left or right!! Embrace the mid century modern style of this home or it is priced to be a tear down to build your dream home around the other multi million dollar homes. Nestled in the heart of highly sought-after Winter Park, this spacious 4-bedroom, 2.5-bath home offers over 3,260 square feet of living space on an oversized .35 acre lot with gorgeous lake views—ideal for enjoying sunsets from a future second-story balcony or out your current kitchen window!! The 4 bedrooms are very generous in size, have ample natural light and each one has oversized closets. The bathrooms have been updated with style in mind. The luxury vinyl floors were recently installed along with new kitchen appliances. Featuring a distinctive Mansard-style roof, this residence boasts strong architectural character and a versatile layout designed for modern living. Inside, you’ll find new luxury plank flooring, large windows that invite abundant natural light, and generously sized rooms with ample closet and storage space. Home offers a lot of character and charm with the present architectural features of a Chicago brick wall, ceiling accent beams and for the art lover a huge paneled art gallery wall!! The home includes two separate living areas, a formal dining room, an eat-in kitchen, and an office area with abundant storage and desk work space —perfect for work-from-home needs, student study session or family organization. The 2-car garage adds both storage and convenience and has a large utility closet inside the garage to stay organized. While the home is ready for your personal touch, it presents a rare chance to customize and elevate a spacious property in a top-rated school district, just minutes from parks, shopping, dining, and lakefront recreation. Whether you're looking to renovate, invest, expand upward, or build your dream home — the potential here is truly exceptional.

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Vonda Fields (321-438-6906)

Remarks: 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.

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Tab Bish Llc (855-450-0442)

Remarks: A high motivation price improvement! Welcome to 2299 Via Tuscany, a remarkable 4-bedroom, 3.5 bathroom residence in the prestigious Winter Park Vias. This 3,986 square foot home, set on a .40-acre private lot, offers a blend of luxury and comfort. The property has seen recent updates in the kitchen and bathrooms and features a new architectural shingle roof (2023), Pebble-tech style pool finish and a manicured landscape. Inside, enjoy the elegance of solid hardwood and modern tile flooring, high ceilings, and two wood burning fireplaces. The chef's kitchen is equipped with premium appliances, including SubZero refrigeration and a Viking 6-burner gas cooktop. The main floor boasts a secluded primary suite, a guest bedroom suite, and a study/library with closet and built-ins. Upstairs, find two additional bedrooms and a full bath. Modern amenities include zoned A/C, a new EV charger and epoxy flooring in the 2-car garage. Conveniently located near parks and the Winter Park Racquet Club, this home offers easy access to downtown Winter Park's shops, dining, and cultural venues, making it ideal for families and active lifestyles. This property also offers deeded lake access to the Winter Park Chain of Lakes by becoming a member of the Maitland Shores Lakefront Preservation Association for an annual fee. The access is very convenient and offers a private ramp to store and launch kayaks, canoes, etc. This location offers effortless access to schools, green parks, fitness centers/trails, cultural venues—an ideal blend of amenities, charm and location for any homebuyer.

Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)

Listing Agent: Vincent Scarlatos (407-718-2378)

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

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Alison Mosley (407-304-6458)

Remarks: 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.

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Mick Night (407-629-4446)

Remarks: Under contract-accepting backup offers. PRESTIGIOUS VIA TUSCANY NEW CONSTRUCTION. If location was a lottery ticket, you just hit the jackpot!!! Welcome to a masterpiece of modern elegance in the heart of the Winter Park Vias. Crafted by the renowned Element Home Builders, this stunning 4,665 sq. ft. estate offers an unparalleled blend of sophistication and comfort. The expansive open-concept floor plan features 5 generous bedrooms, 4.5 luxurious baths, and a dedicated executive office. At the heart of the home, a gourmet chef's kitchen flows seamlessly into a light-filled great room, perfect for grand-scale entertaining. Step outside to your private sanctuary: a brand-new custom pool and a sprawling covered lanai featuring a cozy outdoor fireplace. Situated on a premier corner lot with a brick-lined street, you are just steps away from the Winter Park Racquet Club and minutes from the world-class dining and shopping of Park Avenue. Experience the pinnacle of Winter Park living in a home designed for the most discerning buyer.

Listing is courtesy of: VISTA CAY REALTY COMPANY (407-996-4656)

Listing Agent: Mauro Costa (321-231-6800)

Remarks: One or more photo(s) has been virtually staged. Experience luxury living in this stunning, fully remodeled single-family home located in the heart of Winter Park, where modern sophistication meets exceptional functionality. This spectacular residence features a total of 4 spacious bedrooms and 3 modern bathrooms, boasting sleek laminate flooring throughout and a chef-inspired kitchen fully equipped with premium stainless steel appliances. A standout feature of this property is its versatile layout: one bedroom and one bathroom are completely separate from the main living area, offering the perfect solution for guest privacy, a multi-generational suite, or an opportunity to generate additional rental income. Outside, the massive backyard and sparkling pool provide an ideal setting for family gatherings and outdoor entertainment, all while being nestled in a prime location just minutes from the iconic Park Avenue shopping district, the Winter Park Farmer’s Market, and convenient access to the 436. This home is the ultimate choice for those seeking the perfect blend of suburban tranquility and urban convenience in the very best of Central Florida living.

Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)

Listing Agent: Maria Gomez Arevalo, Pa (407-705-7203)

Remarks: Rare opportunity in the heart of 32789 — priced under $500K, this 3-bedroom, 2-bathroom Winter Park home delivers the location, lot, and bones that buyers in this zip code rarely find at this price point. Zoned for Dommerich Elementary and Winter Park High School and situated on a generous 0.23-acre lot, this is the one worth moving quickly on. Upon entry, a sun-drenched living room leads to a formal dining room, which connects to a secondary living area perfect for entertaining. The open kitchen features granite countertops, stainless steel appliances, and a casual eat-in area, while refinished terrazzo floors run throughout the home adding character and easy-care durability that's quintessentially Florida. 2021 roof and HVAC mean the big-ticket items are already done. Step outside to a large screened-in patio overlooking a spacious backyard with plenty of room to add a pool or expand. Minutes from Park Avenue and Downtown Winter Park's incredible restaurants and fantastic shopping, Rollins College, UCF, AdventHealth Winter Park, Downtown Orlando, and more. At $460,000 in 32789, this one won't last.

Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)

Listing Agent: Caroline Fiore (407-538-2381)

Remarks: One or more photo(s) has been virtually staged. Experience refined living in this exquisitely renovated custom home, positioned on an oversized 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. Inside, soaring 10-foot ceilings and a stately wood-burning fireplace set a welcoming tone 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 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. 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.

Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)

Listing Agent: Kathy Summers (407-832-6986)

Remarks: 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.

Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)

Listing Agent: Kelly Price (407-645-4321)

Remarks: 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!).

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Jennifer Sloan (407-810-8333)