Location: Winter Park
Do Not Show Listings
1923 LINDEN RD, WINTER PARK, FL 32792
$475,00023 Days on yellowkey MLS ID: O6393643
REDUCED by $24,999 (5.0%) on 04/17/2026
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2117 Built: 1955 Tax: $340 (2024)Community: Tanglewood Sec 4Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$340
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: ***WINTER PARK **** 4 BEDROOMS ****3 BATHROOM **** PAID OFF SOLAR ***** WILL HELP BUYER****METAL ROOF ***1/3 ACRE*** Welcome to 1923 Linden Rd, Winter Park—a well-maintained single-story residence offering space, character, and an exceptional location. Built in 1955, this solid masonry and concrete block home features 4 bedrooms, 3 full bathrooms, and approximately 2,117 heated square feet, with 2,281 total building square feet. Located in the highly desirable area of Winter Park, the home provides convenient access to shopping, dining, parks, and top-rated schools, as well as nearby Park Avenue and downtown Orlando. The interior offers a functional layout with multiple living areas, ideal for both everyday living and entertaining. Original character elements such as plaster interior walls and two fireplaces add warmth and timeless appeal. The centrally located kitchen provides ample workspace and flows seamlessly into the main living areas. Situated on a generous 0.315-acre lot (13,717 sq ft) with approximately 117 feet of frontage and 114 feet of depth, the property offers plenty of room for outdoor enjoyment, future enhancements, or expansion. Additional features include Metal Roof that allows for 20 degrees cool, continuous footing foundation, and package cooling system. A strong opportunity for buyers seeking a well-built home with character, space, and long-term value in a prime location.
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Milton James (407-572-4458)
1398 GROVE TER, WINTER PARK, FL 32789
$2,195,0006 Days on yellowkey MLS ID: O6399698
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3450 Built: 2004 Tax: $24,548 (2025)Community: Sylvan Lake ShoresSpa: NoSingle Family
Taxes:$24,548
Elementary School: Brookshire Elem
High School: Winter Park High
Tax Year: 2025
Middle School: Maitland Middle
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)
1161 VALENCIA AVE, WINTER PARK, FL 32789
$4,270,000244 Days on yellowkey MLS ID: O6330736
REDUCED by $25,000 (0.6%) on 04/21/2026
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4181 Built: 2021 Tax: $30,421 (2024)Community: Valencia TerraceSpa: YesSingle Family
Taxes:$30,421
Elementary School: Lakemont Elem
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)
1792 CHILEAN LN, WINTER PARK, FL 32792
$325,00090 Days on yellowkey MLS ID: O6375881
1 Days Off yellowkey (back on 4/21/2026)
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 984 Built: 1959 Tax: $2,677 (2024)Community: Eastbrook Sub Unit 05Single Family
Taxes:$2,677
Elementary School: Eastbrook Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
Remarks: Under contract-accepting backup offers. Welcome home to this darling, move-in-ready Winter Park gem! Perfectly suited as a starter home or investment opportunity, this beautifully remodeled 3-bedroom, 1-bath residence features laminate flooring throughout, a fully remodeled bathroom, and an updated kitchen with granite countertops and stainless steel appliances. Updated plumbing completed in 2014 and a 2017 AC system offer added peace of mind, and tasteful window treatments are already in place. Step outside to a large, fully fenced backyard complete with a fire pit and shed—perfect for entertaining, relaxing, or enjoying Florida evenings. Ideally located in a great area of Winter Park, close to shops, dining, and approximately 30 minutes to everything you want to enjoy in Orlando. One of the best-priced remodeled homes in the area—this charming property is a must-see! NO HOA! Tour this home at
Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)
Listing Agent: Catherine Lambert Pa (407-908-2525)
1830 EDWIN BLVD, WINTER PARK, FL 32789
$679,8006 Days on yellowkey MLS ID: O6400055
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1287 Built: 1957 Tax: $3,955 (2025)Community: Campo BelloSingle Family
Taxes:$3,955
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)
1529 HOLTS GROVE CIR, WINTER PARK, FL 32789
$2,795,00021 Days on yellowkey MLS ID: O6395062
REDUCED by $55,000 (1.9%) on 04/21/2026
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4356 Built: 2005Monthly Fee: $262 Tax: $21,342 (2025)Community: Windsong Lakeside Sec 02 43/71Spa: YesSingle Family
Taxes:$21,342
Middle School: Glenridge Middle
Remarks: Tucked within the prestigious enclave of Windsong Lakeside in Winter Park, this extraordinary estate is a masterclass in refined living—where thoughtful design, cutting-edge technology, and timeless elegance converge. From the moment you arrive, the circular drive and stately presence set a tone of quiet grandeur. Step inside, and the home unfolds with an effortless sense of scale, defined by soaring vaulted ceilings and an abundance of natural light filtering through custom windows. Every detail has been meticulously curated—from the rich new flooring installed in 2025 to the soft glow of Currey & Co. lighting that adds warmth and sophistication to each space. Designed for both comfort and control, the residence is fully integrated with a wireless home automation system, allowing seamless management of lighting, climate, security, and more. Three A/C units ensure optimal comfort, while a new tankless water heater, water softener, and whole-home surround sound system elevate everyday living. A comprehensive security camera system and ADT Home Control provide peace of mind with modern convenience. Each of the four bedrooms is a private sanctuary, complete with its own en-suite bath, offering an elevated sense of privacy for residents and guests alike. The primary suite is a retreat unto itself, featuring custom built-in storage and electric storm shutters with blackout capability. The spa-inspired primary bath showcases a dual Grohe shower system, thermostatic auto tub filler and integrated TV - creating an environment of indulgence and serenity. At the heart of the home lies a newly renovated (2025) chef’s kitchen—an exquisite blend of form and function. Outfitted with premier appliances including a Wolf six-burner gas range, Sub-Zero refrigerator, Monogram built-in microwave, and dual dishwashers, the space is designed for both intimate meals and grand entertaining. Custom cabinetry with integrated lift features, dual sinks, filtered water dispenser, and elegant stone countertops complete this culinary haven. The living room invites relaxation with its newly renovated gas fireplace (2025), while a dedicated office offers bespoke built-in cabinetry with marble surfaces and glass shelving—ideal for sophisticated work-from-home living. Upstairs, the home transforms into an entertainment destination, complete with a projector theatre setup, wet bar, additional powder bath, and extensive storage. A dedicated A/V closet and the potential for an upstairs laundry add both function and flexibility. Outdoors, a private resort-style oasis awaits. The backyard has been completely reimagined, featuring lush turf, a sun deck platform, and even an in-ground trampoline—blending luxury with playfulness. The saltwater pool and spa, enhanced with upgraded LED lighting and a new heater (2025), were fully refinished and redesigned in 2021 to create a serene and visually stunning escape. A fully equipped summer kitchen—complete with a built-in gas grill, dual burners, refrigerator, and screened enclosure—sets the stage for unforgettable gatherings under the Florida sky. The three-car garage is equally impressive, featuring a Wallbox Level 2 electric vehicle charger (2023), seamlessly blending luxury with modern sustainability. This is more than a home—it is a statement of lifestyle, craftsmanship, and elevated living in one of Central Florida’s most sought-after lakefront communities.
Listing is courtesy of: KGV REALTY GROUP (407-474-0844)
Listing Agent: Kristin Vogt Pllc (407-417-7206)
5330 TANGERINE AVE, WINTER PARK, FL 32792
$354,9007 Days on yellowkey MLS ID: O6399019
0 Days Off yellowkey (back on 4/15/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1642 Built: 1976 Tax: $1,296 (2024)Community: WrenwoodSpa: NoSingle Family
Taxes:$1,296
Remarks: You'll love this single-owner gem in Winter Park! Step inside to a traditional foyer, which welcomes you into a formal living room with excellent natural light and great flow into the dining room. Adjacent, you'll find the centrally located, spacious kitchen which overlooks your family room! A true split plan, the primary bedroom and oversized suite are on one side of the home and the two secondary bedrooms and hall bathroom are on the other. Out back, the real "heart of the home" is the generously sized back porch overlooking an original swimming pool! Solidly built block construction on a slab foundation, this 70s home will have you saying "they just don't make them like this anymore"! The major systems have been carefully updated over the years and the next owner will appreciate the peace of mind that a 2019 roof and 2018 HVAC system provide. The laundry is located in the two-car garage.
Listing is courtesy of: MILLER GRANT AND COMPANY (407-399-6031)
Listing Agent: Courtney Pelfrey (407-454-0538)
446 ALBERTA DR, WINTER PARK, FL 32789
$1,675,000307 Days on yellowkey MLS ID: O6319233
0 Days Off yellowkey (back on 3/17/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3263 Built: 1968 Tax: $6,789 (2024)Community: Osceola SummitSingle Family
Taxes:$6,789
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)
2681 FITZHUGH RD, WINTER PARK, FL 32792
$750,00062 Days on yellowkey MLS ID: O6383699
0 Days Off yellowkey (back on 4/20/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2375 Built: 1966 Tax: $5,903 (2024)Community: Winter Park Pines Merrie OaksSingle Family
Taxes:$5,903
Elementary School: Aloma Elem
Remarks: Under contract-accepting backup offers. CALLING FOR HIGHEST AND BEST OFFERS BY MONDAY, APRIL 20th at 9:00 AM. Tucked away on a quiet street in the heart of Winter Park, this fully renovated 4-bedroom, 2.5-bath pool home—enhanced by fully owned solar panels—offers a rare blend of privacy, thoughtful design, and effortless indoor-outdoor living. Set on a generous ¼-acre lot, every detail has been curated to create a home that feels both elevated and family-friendly. Inside, the home opens to a flowing layout ideal for both everyday living and entertaining. Wide-plank luxury vinyl flooring, designer tile, and a soothing, modern palette create a cohesive sense of calm throughout. The kitchen is both a statement and a gathering place, featuring an oversized island wrapped in Taj Mahal quartzite, stainless steel appliances, and a custom wine bar—designed for connection, conversation, and celebration. Adjacent to the kitchen, the sunroom is a showstopper bathed in natural light and enhanced with custom built-ins, this versatile space effortlessly transforms into a home office, playroom, or entertainment lounge. This is where this home comes alive; perfect for large gatherings. The primary suite offers a serene retreat, highlighted by a fully remodeled spa-inspired bathroom with a soaking tub and a sleek, modern shower; inviting you to slow down and unwind. Outside, the newly added 800-square-foot turf play area, side yard, and green space surrounding the pool create room to play, entertain, and relax. The cul de sac and backyard feel exceptionally private, quiet, and peaceful. Just minutes from Park Avenue, you are surrounded by boutique shopping, acclaimed dining, lakeside strolls, and a lifestyle that feels both vibrant and relaxed. From morning coffee runs to evening walks under oak-lined streets, this is the essence of Winter Park living. This home is more than move-in ready—it’s a place to gather, grow and live. ROOF (OCT. 2022) HVAC (2017) WATER HEATER (2016) PLUMBING (2020) ELECTRICAL (UPDATED 2026) POOL PUMP/MOTOR (2020), POOL RESURFACED (2017) DRAIN SYSTEM: FRENCH DRAINS, SUMP PUMPS, GUTTERS (2024)
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Rebecca Bininger Junod (407-230-3650)
1849 VIBURNUM LN, WINTER PARK, FL 32792
$425,000258 Days on yellowkey MLS ID: O6333863
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1627 Built: 1961 Tax: $3,645 (2024)Community: Eastbrook Sub Unit 05Single Family
Taxes:$3,645
Remarks: This beautifully renovated Winter Park home feels warm, inviting, and easy to love. Bright natural light highlights a brand-new kitchen with modern appliances, a waterfall countertop, and soft wood finishes. Both bathrooms have been transformed with elegant marble look tile and spa style showers. You’ll fall in love with the large private backyard, perfect for summer barbecues, outdoor entertaining, play space, or even adding your own backyard oasis. All of this with no HOA and close to top rated Winter Park schools, popular dining, shopping, and parks. This move-in ready home offers lifestyle, comfort, and value you have to see in person, so schedule your showing today before it’s gone!
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Lesly Hijar (321-347-7383)
1905 BONANZA CT, WINTER PARK, FL 32792
$490,0006 Days on yellowkey MLS ID: O6398772
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1774 Built: 1968 Tax: $5,015 (2024)Community: Eastbrook Sub Unit 13Single Family
Taxes:$5,015
Remarks: This beautifully updated 4-bedroom, 2-bath bungalow with a 2-car garage sits on a quiet cul-de-sac and underwent a major renovation in 2023. Nearly every big-ticket item has been replaced, including the roof, A/C, water heater, and double-pane windows-giving you peace of mind for years to come. The home also features a fully updated kitchen with new cabinets, countertops, and a complete appliance package—refrigerator, dishwasher, range, range hood, and microwave—along with new carpeting, ceiling fans, and a new front door. Inside, the spacious family room includes custom built-ins, offering an abundance of storage. Both bathrooms have been tastefully remodeled. The primary bath features a beautiful walk-in shower and dual sinks, while the guest bath offers dual sinks, a jetted tub, a linen closet, and convenient access to the pool area. Step outside to an oversized, fully fenced backyard where you’ll find a sparkling screened-in pool and a large covered patio with an extended overhang—perfect for relaxing or entertaining year-round. And best of all…No HOA! Conveniently located minutes from Downtown Winter Park, key highways, shopping and within an hours drive of all the major theme parks and Orlando International Airport. Welcome Home!
Listing is courtesy of: REAL LIVING R E SOLUTIONS (407-253-1377)
Listing Agent: Lynn Roeder (407-758-8565)
1177 KENWOOD AVE, WINTER PARK, FL 32789
$1,870,00040 Days on yellowkey MLS ID: O6390592
REDUCED by $100,000 (5.1%) on 04/01/2026
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4363 Built: 2007 Tax: $16,206 (2025)Community: Dixie TerraceSpa: NoSingle Family
Taxes:$16,206
Remarks: Welcome to 1177 Kenwood Ave, a home that blends warmth, comfort, and thoughtful design. The inviting living room features a cozy fireplace, creating the perfect space to relax on cooler evenings. The kitchen is designed with both style and function in mind, stainless steel appliances and a center island ideal for meal preparation and gathering. The spacious primary suite serves as a retreat, complete with a walk-in closet and an en-suite bathroom featuring dual sinks, and a separate soaking Jacuzzi. Step outside to enjoy the covered patio—perfect for entertaining or unwinding. The backyard a outdoor escape with a sparkling in-ground pool and a fenced area for added versatility. Inside, the home has been refreshed with new interior paint and partial flooring updates, giving it a clean, updated feel. Don’t miss the opportunity to make this beautiful property your next home. Included 100-Day Home Warranty with buyer activation
Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)
Listing Agent: Karen Albright (480-462-5392)
2299 VIA TUSCANY, WINTER PARK, FL 32789
$2,200,000169 Days on yellowkey MLS ID: O6355858
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3986 Built: 1953 Tax: $26,035 (2025)Community: Maitland ShoresSingle Family
Taxes:$26,035
Elementary School: Dommerich Elem
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)
1840 BRYAN AVE, WINTER PARK, FL 32789
$1,849,00033 Days on yellowkey MLS ID: O6391922
REDUCED by $50,500 (2.7%) on 04/20/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3727 Built: 2014 Tax: $19,607 (2025)Community: Lakeview TerraceSpa: YesSingle Family
Taxes:$19,607
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)
1841 HARLAND PARK DR, WINTER PARK, FL 32789
$1,895,000114 Days on yellowkey MLS ID: O6369653
0 Days Off yellowkey (back on 4/11/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3470 Built: 2014Monthly Fee: $262 Tax: $21,031 (2024)Community: Windsong-Knowles PlaceSingle Family
Taxes:$21,031
Remarks: Price reduction. Motivated seller! Welcome home to the prestigious community of Windsong in Winter Park. Upon entering this Toll Brothers-built home, you will notice no detail has been spared. Soaring ceilings greet you as you enter the foyer with elegant lighting. This 4-bedroom, 3.5-bath home is loaded with upgrades. The office features beautiful wood and detailed, custom bookshelves, complete with a double-door entry for added privacy. The formal dining room features a pass-through to the Butler's Pantry, which leads into a chef's oasis—Wolf stainless steel appliances for the serious chef, and solid surface countertops. The gourmet kitchen opens up to the family room. This home is a Great floor plan for entertaining friends and family. Eat in nook is located off the kitchen for dinners together. The primary suite is located on the first floor with a spa-like ensuite. Double vanity, extra-large shower, large bathtub for when a relaxing bath is just what you need after a long day. Upstairs, you will find a bonus room, as well as the remaining bedrooms. off the bonus room is a bedroom and a full bathroom, great for guests. The other two bedrooms and bathroom are located on the opposite side of the upstairs to create a split floor plan. Large backyard for enjoying the Florida weather. New EV charger in garage, new A/C unit. Home includes surround sound. This home features numerous upgrades, too many to list. Windsong community offers a resort-style pool with lake views, a playground, lake for fishing. Close to restaurants, schools, and shopping.
Listing is courtesy of: SELECTIVE REALTY GROUP LLC (407-627-1727)
Listing Agent: Shanon Luiz (407-247-2241)
5331 OAK CT, WINTER PARK, FL 32792
$460,000280 Days on yellowkey MLS ID: S5130868
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1263 Built: 1976 Tax: $2,311 (2024)Community: Wrenwood Heights Unit 2Spa: NoSingle Family
Taxes:$2,311
Remarks: https://my.matterport.com/show/?m=o2WBZtN1TXm Welcome to Wrenwood Heights Community!! Very well Maintain Pool Home on CUL-DE-SAC LOT!! Great community with no HOA. House located on spacious large lot 0.31 Acre. House features Open Concept with 3 bedroom and 2 bathroom! New Roff 2024. Pool was resurfaced in 2025. Fully Fenced Backyard with upgraded Paver patio and mature landscaping and Fruit trees. Community located in Winter Park close to parks, shopping, dining and main highways. Seminole County schools! Call today to schedule your private showing!
Listing Agent: Nataliya Voroshylo Hylton (407-284-7247)
1052 MANCHESTER CIR, WINTER PARK, FL 32792
$470,00088 Days on yellowkey MLS ID: O6376260
REDUCED by $5,000 (1.1%) on 04/13/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1703 Built: 1983 Tax: $5,216 (2025)Community: Howell Estates 1St AddSingle Family
Taxes:$5,216
Remarks: PRICE REDUCED!! Welcome to your dream home! This beautifully renovated single-story residence features 3 spacious bedrooms and 2 baths, all set on an expansive .42-acre lot in the desirable Howell Estates community. Brand New Roof (2024) Replumbed (2024) New HVAC System, Gourmet Kitchen: Brand new upgraded white cabinets, stunning quartz countertops, and new stainless steel appliances. Luxurious Bathrooms: Both completely renovated, featuring modern finishes Oversized Bedrooms: Including a primary suite with his-and-hers closets and an ensuite bath with a gorgeous walk-in shower. In the Family Room: Spacious layout with a cozy wood-burning fireplace, Oversized Garage: Perfect for larger vehicles, including SUVs. The backyard has a: New Fence, New Pergola and New Extended Porch. This home is move-in ready and waiting for your family to create lasting memories. Don’t miss out on this exceptional opportunity in Winter Park!
Listing is courtesy of: FLORIDA INVESTMENT REALTY GRP (407-937-8450)
Listing Agent: Yuleisy Marquez (407-937-8450)
1870 WALKER AVE, WINTER PARK, FL 32789
$1,399,00040 Days on yellowkey MLS ID: O6390504
REDUCED by $26,000 (1.8%) on 04/19/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2046 Built: 2026 Tax: $3,981 (2025)Community: Osceola HeightsSingle Family
Taxes:$3,981
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 Agent: Mick Night (407-629-4446)
2020 VIA TUSCANY, WINTER PARK, FL 32789
$4,195,0006 Days on yellowkey MLS ID: O6400063
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4665 Built: 2026 Tax: $12,585 (2025)Community: TuscaniaSingle Family
Taxes:$12,585
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)
731 BONGART RD, WINTER PARK, FL 32792
$499,999110 Days on yellowkey MLS ID: S5140952
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1826 Built: 1961 Tax: $5,910 (2025)Community: Winter Park EstatesSingle Family
Taxes:$5,910
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)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.