Location: Winter Park
Do Not Show Listings
2408 LAFAYETTE AVE, WINTER PARK, FL 32789
$1,495,00012 Days on yellowkey MLS ID: O6397694
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2838 Built: 2024 Tax: $3,770 (2024)Community: Winter Park VillageSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,770
Elementary School: Dommerich Elem
High School: Winter Park High
Tax Year: 2024
Middle School: Maitland Middle
Remarks: This custom home is nestled in an up-and-coming neighborhood in Winter Park. This stunning home redefines modern living. Designed with an open floor plan, it seamlessly blends spaces to create a harmonious flow, perfect for both entertaining and everyday life. The abundance of windows bathes the interiors in natural light, creating a bright and airy ambiance. The office/study is set apart for quiet pursuits. The chef’s kitchen opens naturally to the great room and boasts a large island, top-of-the-line Thermador appliances, complemented by the sleek quartz countertops that offer both style and functionality. Conveniently equipped with two sets of washers and dryers, this home ensures efficiency and ease for the busiest of households. Retreat to the master suite, where luxury meets serenity. A massive walk-in closet provides ample storage, while the spa-like master bath invites relaxation with its elegant design and premium features. The indoor outdoor flow is easy with the huge set of glass sliders leading to the covered porch equipped with drop down screens. Enjoy the summer kitchen and sparkling pool while entertaining family and friends. This home is a true gem that combines thoughtful details with sophisticated style.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Matthew Burks (407-257-5347)
405 LAKE FAIR LN, WINTER PARK, FL 32789
$459,99928 Days on yellowkey MLS ID: O6393594
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1491 Built: 1957 Tax: $1,355 (2025)Community: Fairbanks Shores 5Th AddSingle Family
Taxes:$1,355
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: One or more photo(s) has been virtually staged. Fully rebuilt, not just renovated. This Winter Park home at 405 Lake Fair Ln has been completely transformed from top to bottom, with all major systems updated and no detail overlooked, enhanced by custom architectural wood paneling that gives the exterior a modern, high-end presence and standout curb appeal. Positioned on a quiet dead-end street with no side or rear neighbors, this 3 bedroom, 2 bathroom home offers a level of privacy that is rarely found in the area. Inside, a clean, modern layout is complemented by new LVP flooring throughout, large-format designer tile in the bathrooms, fresh knockdown texture, and integrated recessed lighting that creates a bright, cohesive feel from room to room. The kitchen is anchored by an oversized quartz island designed as a central gathering point, paired with modern shaker cabinetry and a full suite of brand new, never-used appliances. The space is built for both everyday functionality and entertaining. Both bathrooms have been fully reimagined with large-format designer tile, a matte black fixture package, and frameless glass shower enclosures, delivering a clean, elevated finish throughout. Beyond the finishes, the true value is in the infrastructure. The home features a new roof, new HVAC system, updated plumbing, and electrical brought to current standards, along with two new water heaters. Additional upgrades include all new interior and exterior doors with coordinated hardware, updated lighting, fresh interior and exterior paint, new blinds, and refined finishes throughout. This is a renovation executed with long-term quality in mind. The location ties everything together. Just minutes from Park Avenue and Winter Park Village, the home offers immediate access to some of the area’s most sought-after dining, shopping, and lifestyle amenities, along with convenient access to I-4 for commuting throughout Orlando. Continued growth in the area adds long-term appeal, including a new Life Time Fitness being developed just minutes away. Education options further strengthen the location. The home is near St. Margaret Mary School, a highly regarded PK–8 private institution, as well as Bishop Moore High School, consistently ranked among the top private schools in Florida and known for strong college preparation and athletics. Edgewater High School is also nearby, offering a well-established public school option within close proximity. Nearby Full Sail University, Rollins College, and AdventHealth Winter Park further support long-term demand and stability in the area. This is a move-in ready home positioned in one of the most stable and steadily growing pockets of Winter Park, offering both lifestyle, privacy, and long-term upside. A full home warranty is included. Seller is motivated and open to strong offers.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Donnamarie Leiba Gough (407-693-6260)
1760 GREENWICH AVE, WINTER PARK, FL 32789
$650,00034 Days on yellowkey MLS ID: O6392001
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1610 Built: 1967 Tax: $2,779 (2025)Community: Golfview HeightsSingle Family
Taxes:$2,779
Elementary School: Brookshire Elem
Middle School: Glenridge Middle
Remarks: Fabulous Winter Park location. This is a 3 bedroom, 2 bath patio home with a great layout, split bedroom plan, high ceilings in the living room, and an eat in kitchen that is open to the family room. A large primary bedroom which has a walk in closet, two additional closets and french doors leading out to the back yard. There is a screened in patio off of the breakfast / dining area and an interior laundry room. Zoned for Winter Park schools, minutes from downtown Park Ave., Rollins College and Advent Health Winter Park. Property is a gem perfect for a renovation or an opportunity to build new.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Meg Dolan (321-948-0701)
240 ORANGE TERRACE DR, WINTER PARK, FL 32789
$484,000258 Days on yellowkey MLS ID: O6330690
REDUCED by $1,000 (0.2%) on 04/15/2026
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1718 Built: 1955 Tax: $6,210 (2024)Community: Orange TerraceSingle Family
Taxes:$6,210
Elementary School: Killarney Elem
High School: Edgewater High
Middle School: Robinswood Middle
Remarks: PRICE IMPROVEMENT - SELLER MOTIVATED - MOVE IN READY - NO HOA, PRIME WINTER PARK LOCATION, CLOSE TO I-4! Nestled in the heart of Winter Park near Lake Killarney, this beautifully updated 4-bedroom, 2-bath home offers the perfect blend of comfort, convenience, and style. Just minutes from Fairbanks and I-4, you’ll enjoy quick access to top shopping, dining, and all that Winter Park has to offer. Fully renovated in 2021—including new roof, electrical, plumbing, fixtures, finishes, and appliances—this home is truly move-in ready. The spacious primary suite is thoughtfully separated from the other bedrooms in a desirable split floor plan, ideal for privacy. Three additional bedrooms provide flexibility for family, guests, or dedicated work-from-home spaces. Enjoy a meticulously maintained yard, a welcoming neighborhood with no HOA, and the charm of one of Winter Park’s most sought-after areas. Don’t miss this gem!
Listing is courtesy of: A+ REALTY PROFESSIONALS, INC (407-702-5243)
Listing Agent: Susan Pinnock (407-435-9125)
1807 MAGNOLIA AVE, WINTER PARK, FL 32789
$1,199,0006 Days on yellowkey MLS ID: O6396616
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2618 Built: 2026 Tax: $4,720 (2025)Community: Temple TerraceSpa: NoSingle Family
Taxes:$4,720
Remarks: Positioned as one of the best values currently available for new construction in Winter Park, this exceptional residence by Hamilton Homes seamlessly blends timeless character with the ease and efficiency of modern living. From the moment you arrive, the home makes a lasting impression with its inviting front porch and classic gas lantern, setting a tone that feels both warm and refined. Inside, the home unfolds into a light-filled, thoughtfully designed interior where every detail has been carefully considered. Just off the entry, a versatile space behind double doors offers the perfect setting for a private home office or an additional bedroom, complemented by a full bath nearby for added convenience. White oak engineered hardwood flooring runs throughout, creating a cohesive and elevated feel, while subtle gold accents at key transitions add a layer of understated sophistication. Designed for both functionality and everyday ease, the main living areas flow effortlessly together. The kitchen serves as the heart of the home, featuring stainless steel appliances, a gas range, abundant cabinetry, and a spacious walk-in pantry. It opens seamlessly to the living and dining areas, creating an ideal environment for both casual living and entertaining. Just beyond, French doors lead to a covered lanai and an oversized backyard, offering a natural extension of the indoor living space. A well-appointed mudroom provides a practical drop zone and connects directly to the oversized two-car garage, enhancing daily convenience. Upstairs, the home continues to impress with a thoughtfully arranged layout that prioritizes both privacy and comfort. The primary suite is a true retreat, offering generous proportions, dual vanities, a large walk-in shower, and custom built-in closet systems. Each additional bedroom is equally well-designed, with all closets throughout the home fully finished for optimal organization. Located in a desirable Winter Park setting, This property is in the heart of it all, 2 miles to AdventHealth Winter Park Hospital, less than 10 minutes to Park Ave, and zoned for top-rated schools such as Dommerich Elementary, Maitland Middle, and Winter Park High. This is a rare opportunity to own a brand new home that delivers both character and quality, all while standing out as one of the most compelling values in today’s Winter Park market.
Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)
Listing Agent: Christopher Christensen (407-312-8003)
785 N PHELPS AVE, WINTER PARK, FL 32789
$2,049,00028 Days on yellowkey MLS ID: O6393117
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2964 Built: 2026 Tax: $9,172 (2025)Community: Comstock ParkSpa: YesSingle Family
Taxes:$9,172
Elementary School: Lakemont Elem
Remarks: Exquisite new construction in the heart of Winter Park, this LUIH Luxury Homes residence distinguishes itself through refined design, thoughtful efficiency, and an elevated level of craftsmanship. From the moment you enter, the home reveals itself with deliberate intention, clean architectural lines and a light-filled, open-concept layout create an effortless flow throughout. The main living space is both sophisticated and inviting, anchored by a sleek electric fireplace and expansive pocketing glass doors that gracefully blur the line between indoor and outdoor living. At the heart of the home, the chef’s kitchen is as striking as it is functional. Adorned with Calacatta quartz countertops and a full suite of premium Thermador appliances, it is designed to accommodate both everyday living and elegant entertaining. The kitchen transitions seamlessly into the dining area, while a walk-in pantry, generously sized mudroom / laundry space, and wine cellar add layers of convenience and luxury rarely found in homes at this price point. The primary bedroom suite offers a true sanctuary with direct access to a secluded outdoor patio that provides a serene extension of the space. The spa-inspired bath showcases a freestanding soaking tub, dual vanities, and an expansive walk-in shower. Upstairs, four additional bedrooms offer generous proportions and versatility, ideal for guests, family, or tailored uses such as a home office or fitness studio. Designed for year-round enjoyment, the outdoor living experience is equally captivating. A sprawling covered lanai features a fully equipped summer kitchen with grill, sink, and beverage refrigerator, overlooking a meticulously designed backyard complete with a resort-style pool and spa, perfect for both intimate evenings and grand entertaining. All of this is ideally located just moments from the boutiques and dining of Park Avenue, with convenient access to Phelps Park and the Winter Park YMCA, placing you at the center of one of Central Florida’s most desirable lifestyles.
3463 ARNEL DR, WINTER PARK, FL 32792
$459,90036 Days on yellowkey MLS ID: O6390301
REDUCED by $20,000 (4.2%) on 04/12/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1770 Built: 1967 Tax: $4,648 (2024)Community: Eastbrook Sub Unit 11Single Family
Taxes:$4,648
Elementary School: Eastbrook Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
Remarks: PRICE IMPROVEMENT!! Your pool home in Winter Park just became an even better opportunity. This home offers 3 bedrooms plus a versatile bonus room, approximately 1,770 sq ft of living space, built in 1967, with a 2-car garage and extended driveway for extra parking — all located in the established Eastbrook community with NO HOA. Major updates already done for you: roof 2018, solar panels 2020 (fully paid off), water heater 2019, and AC replaced in July 2013. A home warranty through First American Home Warranty is included, giving added peace of mind on major systems. Inside, you’ll find a bright and functional layout with comfortable living and dining spaces that flow naturally. The kitchen has been updated with granite countertops and modern cabinetry, and both bathrooms feature clean, updated finishes. The bonus room gives you flexibility — perfect for a home office, gym, playroom, or even a 4th bedroom setup. Step outside to your fully fenced backyard with a private pool — ideal for relaxing, entertaining, and enjoying Florida living year-round, with a great balance of pool deck and green space. Location is key — just minutes to Park Avenue, Rollins College, Full Sail University, and University of Central Florida, plus easy access to major highways and top-rated Seminole County schools. With the new price, this is a strong opportunity in Winter Park — especially for buyers looking for space, a pool, and no HOA.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)
Listing Agent: Alexa Monasterio Flores (786-915-9294)
3131 LOWNDES DR, WINTER PARK, FL 32792
$529,95043 Days on yellowkey MLS ID: O6388846
REDUCED by $4,950 (0.9%) on 04/16/2026
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 2126 Built: 1967 Tax: $1,559 (2024)Community: Georgetown EstatesSingle Family
Taxes:$1,559
Remarks: Enjoy the Winter Park Lifestyle in this Beautiful 4 Bedroom Pool Home! The Entire Interior is New, Furnished and Move-in Ready! Entertain in style with a Large Eat-In Kitchen, Stainless Steel Appliances, Soft-Close Cabinetry and Quartz Countertops. Open Floorplan with Entryway into the Living and Dining area that overlooks your Screen-Enclosed Pool/ outdoor Living Space with a Fenced Yard. Versatile Flex Space perfect for a Home-Office, Entertainment Room, or cozy Family Retreat. Three Bedrooms on one side of the house with a Huge Tranquil Master Suite on the other side. Indulge in the Oversized Walk-In Steam Shower, Custom Double Sinks with Backlit Mirrors and Double Closets in the Dressing Area. Master Suite has a Real Fireplace and Pool access through Sliding Glass Doors. Luxury Vinyl Plank Flooring and Fresh Paint throughout. Elegant Designer Wall and Floor Tiles in the Bathrooms with New Sinks, hardware, and faucets. Newer Roof (2021). Light and bright. This home is a gem. The floorplan must be seen to be appreciated. This home is nestled on a Quiet tree-lined street, near top-tier restaurants, businesses, shopping, parks, recreation, top rated schools, and Park Avenue only 4 miles away. Two Workshop/Sheds for storage and creative projects in the back yard. Schedule your private tour today!
Listing is courtesy of: A +ROI PROPERTY (407-718-7994)
Listing Agent: Rene Fossey (407-718-7994)
1926 NATALEN RD, WINTER PARK, FL 32792
$649,90047 Days on yellowkey MLS ID: O6388308
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1469 Built: 1957 Tax: $7,308 (2024)Community: Kenilworth Shores Sec 07Single Family
Taxes:$7,308
Remarks: ***MUST SEE WINTER PARK POOL HOME*** Explore the virtual tours to fully appreciate the beauty of this completely renovated 3 bedroom/2 bath solid block pool home nestled in the highly desirable Kenilworth Shores community in Winter Park. This move-in-ready home features an open layout with vaulted ceilings and an abundance of natural light, highlighted by a large free-flowing kitchen with all the amenities... new stainless-steel GE appliances, elegant quartz countertops, sturdy oversized soft-close shaker cabinets and two large built-in wall pantries. The open living area includes a cozy formal dining room with additional countertop seating, and a picturesque sliding glass door opens to an extra-large 40 x 12 outdoor covered porch that provides additional casual outdoor living space. The spacious primary bedroom has a vaulted ceiling and his/her closets, with private access to the backyard covered porch, and features a fully renovated en-suite bath. The secondary bathroom has been tastefully upgraded, as well. Freshly painted inside and out, this immaculate home has new waterproof LVP flooring throughout, new light fixtures and ceiling fans, and stylish window shade coverings on every window. With an indoor laundry room and a two-car carport, this worry-free home features a new AC unit installed in 2025, a new electrical panel and updated plumbing, and a roof that was replaced in 2018. Setting this home apart is your private outdoor private backyard oasis, showcasing a gorgeous 32 ft long/10 ft deep in- ground pool plus a unique outdoor kitchen . . . perfect for family gatherings or hosting a Bar-b-que pool party . . . and with a generously sized 10’ x 18’ shed with full electric providing additional storage solutions or living options, this fully fenced-in backyard is truly a tranquil outdoor haven. Zoned for excellent Winter Park schools, this home is located four blocks from Winter Park High and less than a mile from Brookshire Elementary and Glenridge Middle. It comes with deeded access to the boat ramp and fishing dock at Lake Berry. Blue Jacket Park and Cady Way Park are just down the street, showcasing great bike trails for walking and jogging. The well-known shopping and restaurants of downtown Park Avenue and Baldwin Park are just minutes away. Rollins College, UCF, Full Sail University, and Winter Pines Golf Course are all close by. And Advent Health/Winter Park Hospital is less than a mile down the street. This is a quiet, family-friendly community known for its tranquility and peaceful living. Don’t miss this opportunity to make this wonderful home your very own. Schedule your showing today.
Listing is courtesy of: JAMIESON PROPERTIES, INC. (407-876-2730)
Listing Agent: Joseph Cosgrove (407-470-0892)
330 ELKHORN CT, WINTER PARK, FL 32792
$559,90087 Days on yellowkey MLS ID: O6376757
REDUCED by $10,000 (1.8%) on 04/16/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1570 Built: 1965 Tax: $2,086 (2025)Community: Winter Park Pines Merrie OaksSingle Family
Taxes:$2,086
Remarks: 330 Elkhorn Ct is a beautifully renovated home located in the highly desired Winter Park Pines community. Freshly updated with a 2025 electric panel, 2025 A/C system, and a 2024 roof, offering modern efficiency, peace of mind, and big-ticket upgrades already taken care of! Inside, you’ll find a bright, open layout with wide-plank flooring, recessed lighting, and a modern neutral color palette that feels clean and inviting. The kitchen has been thoughtfully updated with shaker-style cabinetry, sleek countertops, stainless steel appliances, and designer finishes—including a farmhouse sink and gold hardware/fixtures that add a high-end touch. The bedrooms offer comfortable space with updated finishes throughout, while the oversized backyard provides plenty of room to relax, entertain, garden, or create your ideal outdoor setup. Conveniently located near shopping, dining, parks, and major roadways—and zoned for top-rated schools including Winter Park High School—this home is a standout opportunity in one of the area’s most sought-after neighborhoods.
Listing is courtesy of: LA ROSA REALTY CW PROPERTIES L (407-910-2168)
Listing Agent: Neil Chetram (407-752-1597)
638 BLAIRSHIRE CIR, WINTER PARK, FL 32792
$639,0004 Days on yellowkey MLS ID: C7524884
0 Days Off yellowkey (back on 4/18/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1701 Built: 1964 Tax: $2,816 (2025)Community: Brookshire Heights 4Th AddSpa: YesSingle Family
Taxes:$2,816
Remarks: Under contract-accepting backup offers. Well-maintained 3 bedroom, 2 bath one story pool home. This home is on a highly desirable street near three high rated schools, parks, shopping, emergency services, Cady Way Trail and Center for Health and Wellbeing. The garage is two car with two built in storage areas. Make your appointment to see this beautiful home!
Listing is courtesy of: REALTY ONE GROUP MVP (800-896-8790)
Listing Agent: Sharon Wainman (239-297-4434)
2007 EDWIN BLVD, WINTER PARK, FL 32792
$369,90016 Days on yellowkey MLS ID: O6396498
REDUCED by $5,100 (1.4%) on 04/15/2026
Bed: 3 Bath: 1.5 Liv Area Sq Ft: 1296 Built: 1955 Tax: $3,535 (2025)Community: Eastgate SubSingle Family
Taxes:$3,535
Remarks: Excellent opportunity to renovate existing home or build your dream home in Winter Park. Mid-Century Modern on 10,278 SqFt corner lot. Home being sold AS-IS. Updated roof & HVAC. Zoned for Lakemont, Maitland Middle, Winter Park High. Centrally located near restaurants, shopping, Winter Park Hospital & a short drive to Park Avenue, Rollins College & many local parks.
Listing Agent: Catherine D'Amico (407-252-3210)
102 BELL PL, WINTER PARK, FL 32792
$1,399,0008 Days on yellowkey MLS ID: O6398118
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2459 Built: 2025 Tax: $4,224 (2025)Community: Eastgate SubSingle Family
Taxes:$4,224
Remarks: Step into elevated Florida living with this stunning brand-new residence, where modern design meets lasting quality. Constructed with solid block and steel framing for superior durability, this home is quietly nestled on a cul-de-sac in one of Winter Park’s most up-and-coming areas—without the restrictions of an HOA. Just moments from Interlachen Country Club and the charming Lakemont Heights neighborhood, the location offers both prestige and convenience. From the moment you enter through the impressive double doors, you’re welcomed by a light-filled, open-concept design. Soaring 10-foot ceilings and elegant 8-foot doors create an airy, expansive feel, while abundant natural light highlights the home’s sleek, contemporary finishes. At the heart of the home, the chef-inspired kitchen truly shines. Outfitted with luxurious quartz countertops, stainless steel appliances, and a custom LED-lit wine display, it’s designed to impress. The seamless flow into the living and dining spaces—along with views of the backyard—makes it perfect for entertaining or everyday connection. The primary suite is a private sanctuary, offering a spa-like escape with dual vanities, a spacious dual-entry shower, and a freestanding soaking tub designed for relaxation. With three additional bedrooms, a dedicated office, and 3.5 beautifully appointed bathrooms, this thoughtfully designed single-story home provides nearly 2,500 square feet of flexible living space. Outdoors, your personal retreat awaits. Enjoy year-round Florida living on the covered lanai, complete with a built-in summer kitchen and a custom-designed pool—ideal for hosting or unwinding. The fully fenced yard features new vinyl fencing, fresh sod, and an automated sprinkler system for effortless maintenance. Perfectly positioned near Phelps Park, the Winter Park YMCA, Lakemont Elementary, and an array of top-tier shopping and dining destinations, this home delivers the ideal blend of privacy, craftsmanship, and everyday luxury.
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Nick Mckee (407-913-0171)
1369 BLUE STEM LN, WINTER PARK, FL 32792
$825,00015 Days on yellowkey MLS ID: O6396971
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2589 Built: 2021Monthly Fee: $413 Tax: $6,074 (2024)Community: Landings At Hawks CrestSingle Family
Taxes:$6,074
Remarks: Nestled in one of the most sought-after neighborhoods in Winter Park, this exceptional gated residence offers the perfect blend of elegance, comfort, and modern efficiency. Ideally located just five minutes from top-rated private schools, this two-story single-family home is designed for both luxurious living and everyday functionality. Upon entry, you are welcomed by a dramatic grand foyer featuring soaring ceilings of nearly 20 feet, creating an impressive and light-filled living space. The open layout seamlessly connects the main living areas, ideal for entertaining and family gatherings. This thoughtfully designed home features 4 spacious bedrooms and 3.5 bathrooms, including dual primary suites—one conveniently located on the main level and another upstairs—providing flexibility for multi-generational living or guest accommodations. A dedicated private office on the first floor offers the perfect work-from-home environment. Step outside to a beautifully maintained backyard with premium artificial turf, fully fenced for privacy, and a screened rear patio—perfect for relaxing or enjoying Florida’s outdoor lifestyle year-round. Extensively upgraded throughout, the home showcases high-quality finishes with no carpet—featuring elegant flooring and tile across all living areas, along with a solid wood staircase that adds warmth and sophistication. The garage is equally well-appointed with a premium epoxy-coated floor, offering both durability and a clean, polished look. Energy efficiency is a standout feature of this home, equipped with a tankless water heater for on-demand hot water and reduced energy consumption, as well as solar panels that help significantly lower utility costs. This is a rare opportunity to own a meticulously upgraded home in a prime Winter Park location—ideal as a primary residence or a high-potential investment property.
Listing is courtesy of: U S GLORY REALTY (407-222-7801)
Listing Agent: He Gao (407-955-0138)
1300 MAYFIELD AVE, WINTER PARK, FL 32789
$2,850,00026 Days on yellowkey MLS ID: O6393777
Bed: 5 Bath: 5.5 Gar: 4 Liv Area Sq Ft: 4389 Built: 1958 Tax: $26,658 (2025)Community: Temple HeightsSpa: NoSingle Family
Taxes:$26,658
Remarks: Tucked behind towering hedges on a coveted brick-lined street, this estate sits on an approximately ½-acre corner lot and has been enhanced with thoughtful improvements, delivering a rare combination of modern functionality, Old World charm, and a fabulous lifestyle. Notable updates include newer HVAC systems (2020 and 2025), a tankless gas water heater, a fully renovated laundry room with new LG stackable washer and dryer, newer kitchen appliances, new copper gutters and downspouts, fresh exterior paint (2025), a newly designed primary bathroom, and much more. The main residence spans over 3,600+ SF with an attached 2-car garage and is complemented by a detached, fully equipped 700+ SF studio apartment located above an additional 2-car garage, as well as an air-conditioned outdoor bar. With two dwellings, a four-car garage, expansive outdoor entertaining space on ½ acre, and surrounded by tall podocarpus hedges, this home is a true private compound. This is not just a home—it’s a destination! Enter the main residence into a dramatic living space featuring 12-foot ceilings, a 30-foot span, a gas fireplace, and walls of windows and doors. With a rear southern exposure, natural light pours in through five sets of French doors, offering views of the brick-paver pool deck and lush, fenced grounds beyond. The family room flows seamlessly into the open kitchen, elevated by newer luxury appliances including a Sub-Zero refrigerator, Wolf gas range, and dual Miele dishwashers. At the center, a copper-topped island anchors the space, complemented by a wood-stained beadboard ceiling and a spacious dinette for casual dining. Just beyond the kitchen, a large dining room and adjacent den (currently used as a library & office) offers flexible living options. A side entrance opens to a covered porch overlooking a generous side yard framed by tall privacy hedges—ideal for a dog run or discreet boat storage. Downstairs, three additional bedrooms feature vaulted ceilings and access to three well-appointed full baths, creating a functional layout for family and guests. Privately positioned upstairs, the expansive primary suite offers a quiet retreat, highlighted by a recent full-scale luxury bathroom renovation with elegant custom finishes. Features include a large glass shower with three showerheads, dual vanities, a Toto washlet, designer mood lighting, and custom cabinetry with linen storage. French doors from both the bedroom and bath open to a covered balcony overlooking the backyard and pool, while three custom walk-in closets create a true dressing room experience with additional flexible space for an office or hobby room. Designed for entertaining, the outdoor living is equally impressive. A sprawling lawn surrounds the large saltwater pool and expansive paver patio for lounging and dining. A covered, air-conditioned bar is outfitted with custom cabinetry, exquisite lighting, a copper sink, dishwasher, wine fridge, and beverage fridge—all secured by an electronic storm shutter. The extended bar seamlessly serves the adjacent tent-covered lounge area, complete with a pool bath and outdoor shower. The detached studio apartment, positioned above the second 2-car garage, features a private entry along with a full kitchen and bath, making it ideal for extended stays or flexible living arrangements. Located just minutes from vibrant Park Avenue, this distinctive Winter Park compound blends curated finishes, meaningful upgrades, and exceptional privacy.
Listing Agent: Marystuart Day (407-620-8683)
418 GILBERT RD, WINTER PARK, FL 32792
$740,00027 Days on yellowkey MLS ID: O6385950
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1680 Built: 1964 Tax: $9,094 (2025)Community: Winter Park Pines Ut 5Single Family
Taxes:$9,094
Remarks: Beautifully renovated solid block home on a quiet street in highly desirable Winter Park Pines! This property features fresh exterior paint, updated lighting, a newly paved courtyard, and a bright open floor plan. The stunning kitchen offers modern cabinetry, quartz countertops, and brand-new stainless steel appliances, flowing seamlessly into the dining and family rooms. The sun-drenched Florida room is lined with windows that brighten the entire living space. Complete with a dry bar and its own mini-split AC unit, it offers flexible space for entertaining, relaxing, or creating your dream retreat. The split floor plan includes three generously sized bedrooms and three full renovated bathrooms, with a private primary suite with walk-in closet off the family room and the additional bedrooms and bath located on the opposite side of the home. The attached two-car garage offers excellent potential to be converted into a fourth bedroom, utilizing the existing full bathroom to create a private mother-in-law suite or guest quarters. Additional upgrades include new flooring, trim, doors, fixtures, and fresh interior paint. Create your own outdoor oasis with a newly paved patio and large fenced backyard with room for a pool. Ideally located near downtown Winter Park, Park Avenue shopping and dining, Cady Way Trail, and zoned for top-rated schools. Schedule your showing today!
Listing is courtesy of: SOTERA LIVING (407-725-9660)
Listing Agent: Lianna Dangelo (321-446-3509)
629 COUNTRY CLUB DR, WINTER PARK, FL 32789
$1,695,00053 Days on yellowkey MLS ID: O6386610
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3031 Built: 2026 Tax: $2,028 (2025)Community: Lords SubSpa: NoSingle Family
Taxes:$2,028
Remarks: Newly built in the heart of Winter Park, this warm modern-industrial residence offers 4 bedrooms, 3.5 baths and 3,031 heated square feet of thoughtfully designed living space (3,674 total including a two-car garage). Soaring 12’8” ceilings downstairs and 10’ ceilings upstairs create volume and light throughout. Oversized black grid windows flood the home with natural light and offer water views from the second level. Designer LED ambient lighting is integrated throughout — including illuminated floating stair treads and custom feature shelving — creating a dramatic yet inviting atmosphere. The kitchen is both refined and functional, featuring an oversized island, premium appliances, expansive prep space, and a generous walk-in pantry. The open layout flows seamlessly into the living and dining areas, anchored by a striking fireplace feature wall and wide-plank wood flooring. The primary suite offers a spa-level retreat with a dedicated wet area and freestanding soaking tub, delivering a luxurious, architectural bathroom experience. Designed for entertaining, the outdoor living space includes a private pool and a fully equipped summer kitchen — ideal for Florida living year-round. Additional features include: • Spray foam insulation for superior efficiency • Deeded access to a private boat ramp on Lake Killarney • No HOA dues Located in one of Central Florida’s most desirable neighborhoods, this home is just a short walk or drive to Park Avenue dining, shopping, and entertainment. A rare opportunity to own new construction with architectural character in Winter Park.
Listing is courtesy of: CLASSIC HOMES (407-493-8553)
Listing Agent: Randy Lazarus (407-247-9337)
151 OAKWOOD WAY, WINTER PARK, FL 32789
$2,950,00076 Days on yellowkey MLS ID: O6380037
REDUCED by $105,000 (3.4%) on 04/01/2026
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4129 Built: 2023 Tax: $34,218 (2025)Community: CharmontSpa: NoSingle Family
Taxes:$34,218
Middle School: Audubon Park K-8
Remarks: Welcome to 151 Oakwood Way, a beautifully executed residence by LunDev Custom Homes, set on a quiet, tree-lined street in the heart of Winter Park. Blending timeless architecture with a clean transitional aesthetic, this newer pool home offers sophisticated design, comfortable livability, and the kind of indoor-outdoor flow today’s buyers are looking for. Inside, the home is filled with natural light and thoughtfully designed for both everyday living and entertaining. Wide-plank engineered hardwood flooring, quartz surfaces, premium Thermador appliances, and well-selected finishes create a refined, elevated feel throughout. The open-concept layout lives effortlessly, with inviting spaces that feel both polished and welcoming. The outdoor setting is a true highlight. A covered lanai with a summer kitchen and automatic screens opens to a beautiful saltwater pool and separate spa, creating a private, resort-style backdrop for relaxing or hosting year-round. A spacious flex room adds valuable versatility and can easily function as an office, game room, media space, or potential future guest suite, with plumbing already in place for added flexibility. Thoughtfully designed and exceptionally well located, 151 Oakwood Way presents a rare opportunity to own a newer luxury home in one of Winter Park’s most desirable settings.
640 ARJAY WAY, WINTER PARK, FL 32789
$1,925,00092 Days on yellowkey MLS ID: O6372947
REDUCED by $49,900 (2.5%) on 04/15/2026
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3953 Built: 1958 Tax: $11,586 (2024)Community: Timberlane ShoresSingle Family
Taxes:$11,586
Elementary School: Audubon Park K8
Remarks: $50,0000 Price Improvement on this amazing oversized lot! Located in one of Winter Park’s most desirable and picturesque neighborhoods, Timberlane Shores! This stunning five-bedroom residence has been recently renovated in an elegant, European style blending timeless character with modern luxury. Situated on over one-third of an acre, the property is accented by majestic oak trees and lush Florida-native landscaping that's creates a private and serene retreat where peacocks often roam freely through your yard. The heart of the home is the beautifully designed chef’s kitchen, featuring quartz countertops, a gas range with custom hood, double built-in convection ovens, stainless steel appliances, a wine refrigerator, and a well-appointed butler’s pantry—perfect for entertaining. The light-filled family room is open to the kitchen and showcases a wood-burning fireplace, custom built-ins, and an original brick accent wall that adds warmth and architectural charm. Engineered hardwood flooring and preserved original terrazzo floors run throughout the home, enhancing its quality designer choices but also an inviting feel. The flexible floor plan offers five spacious bedrooms, three full bathrooms, and two half baths, providing ample space for both everyday living and hosting guests. Expect to be impressed by the elegant owner's suite with a sizable walk-in closet and stunning ensuite bathroom featuring dual vanities, beautiful cabinetry with lots of storage and a generously sized soaking tub. Outdoor living is equally impressive, with a resort-style heated pool complete with a sun shelf, an outdoor kitchen with a built-in grill, sand volleyball court and a large deck featuring built-in seating and a fire pit—ideal for gatherings or relaxing evenings under the stars. Zoned for Winter Park’s top-rated schools, this exceptional home is just a five-minute drive to Park Avenue’s renowned shopping and dining, and walking distance to Baldwin Park’s vibrant downtown, offering shops, restaurants, and a Publix. This is a rare opportunity to own a thoughtfully renovated home in one of Winter Park’s most beautiful and sought-after settings. Experience the rare combination of European-inspired luxury, resort-style outdoor living, and an unparalleled Winter Park location. Be sure to watch the video tour and virtual property walkthrough in the attachments. Better yet, schedule a private showing today and discover a home that truly defines elevated Florida living.
Listing Agent: Farah Bloom (407-873-5222)
2702 PARKLAND DR, WINTER PARK, FL 32789
$1,175,00012 Days on yellowkey MLS ID: O6397997
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2656 Built: 1949 Tax: $5,269 (2025)Community: ParklandoSingle Family
Taxes:$5,269
Remarks: Welcome to this beautifully updated Winter Park home, perfectly positioned on a desirable corner lot and zoned for Audubon Park K-8 and Winter Park High School. With 5 bedrooms and 3 full baths, this spacious residence offers the ideal blend of functionality and style for modern living. Step inside to an open, light filled floor plan featuring luxury vinyl floors and a cozy wood burning fireplace that anchors the main living space. The renovated kitchen is thoughtfully designed with both everyday living and entertaining in mind, flowing seamlessly into the dining and living areas. A dedicated office provides the perfect work from home setup or quiet retreat, while the flexible layout offers plenty of room for guests, growing families, or multi generational living. Outside, enjoy a private backyard with a charming fire pit and rock gathering are deal for relaxing evenings or hosting friends. The oversized lot also offers ample space to add a pool and create your own backyard oasis. Additional highlights include a 2-car garage, roof replaced in 2018, home repiped in 2019, and updated AC for peace of mind. This is a rare opportunity to own a move-in ready home in one of Winter Park’s most sought after neighborhoods, walking distance to the Audubon Park Garden District with amazing dining, and shopping.
Listing is courtesy of: NORDQUIST & COMPANY INC (407-694-0996)
Listing Agent: Elizabeth Nordquist (407-694-0996)
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