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$595,000
3 Beds ⋅ 2 Baths ⋅ Kenilworth Shores Sec 03 SubDv. ⋅ 32792 Zip Code
Welcome to this stylishly renovated ranch-style pool home in Kenilworth Shores, a special Winter Park neighborhood known for its connected community, central location, and easy access to everything people love about Winter Park. This beautifully renovated 3-bedroom, 2-bath home sits on nearly a quarter-acre lot and offers the perfect blend of style, comfort, and outdoor living. Step inside and you'll immediately feel the warmth of the home. The renovated kitchen is truly the heart of the space, beautifully designed with stylish tile backsplash, stainless steel appliances, mission style cabinetry, bar seating, and an additional coffee or wine bar area that makes the space feel both functional and elevated. Open to the living room, the kitchen creates an easy flow for everyday living and entertaining. The home has been thoughtfully updated throughout with new flooring, plantation shutters, renovated bathrooms, and designer touches that give the home a fresh, modern feel while still keeping all the charm of a classic Winter Park ranch. A dining room along the back of the home offers views of the yard and access to the covered lanai and custom pergola overlooking the pool. This is truly a backyard retreat! The sparkling pool is surrounded by pavers, lush landscaping, bamboo for privacy, and a fully fenced yard. The covered lanai and custom pergola create the perfect setting for morning coffee, quiet evenings, or hosting friends by the pool. This is the kind of backyard that makes Florida living feel easy. A large storage area and laundry room provide extra space for bikes and yard tools just off the carport. The bedrooms are tucked together along the hall, with the primary bedroom positioned on the back of the home for privacy, with an additional bathroom featuring an updated vanity and shower and a door to the pool area. The additional bedrooms share the hall bathroom with stylish modern updates including all new tile, a frameless glass shower, vanity, and fixtures. The thoughtfully designed spaces feel modern while also remaining timeless and classic. Other notable additions over the years include a metal roof, irrigation on well, lush landscaping, and a refinished pool with tile surround. The 2-car carport provides plenty of covered parking for rainy days! Located in the City of Winter Park, this home offers incredible access to Park Avenue shopping and dining, Audubon Park with Michelin-star restaurants and local favorites, Sprouts Market, Lake Baldwin Dog Park, nearby parks, coffee shops, boutiques, and more. Zoned for Brookshire Elementary, Glenridge Middle, and Winter Park High. Cady Way Park is nearby with a community pool, baseball fields, a playground, pickleball courts, and miles of recreational and bike trails. Style, location, privacy, sparkling pool! This Winter Park home checks all the boxes. Schedule your private showing today!

508 Dunraven Drive, Winter Park
$766,000
4 Beds ⋅ 5 Baths ⋅ Kings Cove SubDv. ⋅ 32792 Zip Code
BELOW APPRAISAL GEM IN WINTER PARK. Welcome to this beautifully and luxuriously updated 4-bedroom, 4-bath pool home located in the highly desirable Kings Cove community of Winter Park. Offering over 3,000 square feet of living space on a spacious 0.31-acre lot, this home blends comfort, functionality, and major system upgrades. The kitchen is designed for both everyday living and entertaining, featuring a gas stove, double oven, warming drawer, extra-large refrigerator, and custom pull-out cabinetry. The oversized island includes an additional sink, built-in microwave, and new (2025) under-counter ice maker. Recent upgrades and improvements include: New roof (2021) New first-floor A/C system (2021) New septic tank (2023) New hot water heater (2025) The primary suite has been thoughtfully updated in 2026, featuring a fully renovated bathroom with dual sinks and in-drawer electrical outlets, along with a custom-designed closet system completed in March 2026. New carpet was installed in April 2026. Additional highlights include a dedicated laundry room with sink and wine storage, a custom pantry with oversized pull-out drawers, built-in entertainment center, and a ceiling-mounted audio system controlled by phone. Step outside to enjoy your private in-ground pool and a quiet, established neighborhood close to top-rated schools, shopping, dining, and major highways. This is a move-in-ready home with major systems already updated and high-end functional upgrades throughout—don’t miss this opportunity.

4348 Steed Terrace, Winter Park
$650,000
3 Beds ⋅ 2 Baths ⋅ Brookshire Heights 4th Add SubDv. ⋅ 32792 Zip Code
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!

638 Blairshire Circle, Winter Park
$360,000
3 Beds ⋅ 2 Baths ⋅ Oakcrest-516 SubDv. ⋅ 32792 Zip Code
Welcome to this charming 3-bedroom, 2-bath home tucked away on a quiet cul-de-sac in the Oakcrest community of Winter Park. Offering 1,252 square feet of comfortable living space, this single-story ranch sits on a generously sized 0.22-acre lot that provides plenty of room to enjoy outdoor living, entertain guests, or create your own backyard retreat. Inside, the home features a bright and functional layout with high ceilings, ceiling fans, and inviting living and dining areas that create a comfortable space for everyday living. The kitchen offers ample cabinetry and includes a range, refrigerator, and dishwasher, making it both practical and convenient for daily use. Tile and carpet flooring combine durability with comfort throughout the home, while built-in features and window treatments add to the home’s charm and functionality. The split-style layout provides privacy for the primary bedroom while two additional bedrooms offer flexibility for family, guests, or a home office. Outside, the private backyard is fully fenced and includes storage sheds and an irrigation system, giving you the space and versatility to garden, relax, or host gatherings. The home also features a two-car garage for additional storage and parking. The property truly stands out with its beautifully maintained landscaping, where the care and time invested by the owner is evident throughout the yard, creating a welcoming setting and enhancing the home’s curb appeal. Located in desirable Winter Park within Seminole County and zoned for Eastbrook Elementary, Tuskawilla Middle, and Lake Howell High School, this home combines comfort, convenience, and value. With easy access to shopping, dining, parks, and major roadways throughout Central Florida, this property offers a wonderful opportunity to enjoy life in one of the area’s most established communities.

7213 Silver Place, Winter Park
$170,000
2 Beds ⋅ 2 Baths ⋅ Four Seasons Condo SubDv. ⋅ 32792 Zip Code
Welcome to the beautiful community of Four Seasons! This well-established condominium complex is coveted for its fantastic location in Winter Park, excellent schools, proximity to restaurants, grocery stores, shopping and Park Avenue. Four Seasons is a 20-acre, park-style neighborhood featuring tranquil courtyards with mature landscaping and majestic oak trees. Four Seasons amenities include 3 community pools, shuffleboard, clubhouse with a library and onsite management. This first-floor unit has been updated with new interior paint, includes a screened-in patio and a washer and dryer! Monthly HOA fees conveniently include water, trash, sewer and pest control. Walk or bike to Brookshire Elementary, Glenridge Middle and Winter Park High School! Full Sail, Valencia College and UCF are minutes away as well as quick access to major roads and 25 minutes to Orlando International Airport. Nearby conveniences include Advent Health, The Wellness Center, Winter Park Pines 18-hole golf course and restaurant, Ward Park and the Cady Way Pool. Easy show...schedule your showing today before this 2/2 gets snapped up!

200 Saint Andrews Boulevard Unit 2206, Winter Park
$485,000
4 Beds ⋅ 2 Baths ⋅ Winter Woods Unit 04 SubDv. ⋅ 32792 Zip Code
Welcome to 1921 Japonica Rd – Your Winter Park Retreat Awaits Tucked away on a quiet street just minutes from the heart of Winter Park, this beautifully maintained 4-bedroom, 2-bath home offers the perfect blend of comfort, character, and potential. From the moment you arrive, you'll notice how lovingly this home has been cared for, offering peace of mind with newer roof (2021) and a complete HVAC system and ductwork replacement in 2023. Step inside to a thoughtfully designed split floor plan, ideal for privacy and flexibility. The main living areas boast updated flooring, while plush carpet adds comfort to the bedrooms. The kitchen is full of charm, and includes the stove, microwave, and refrigerator, making it immediately enjoyable with plenty of room for personal touches down the road. The home flows seamlessly into a spacious backyard oasis that is fully fenced, beautifully landscaped, and ready for your summer cookouts or weekend gatherings. Dreaming of a pool? The yard was thoughtfully prepared with future plans in mind, perfectly sized and situated for a custom pool addition. Additional features include a leaf filter gutter protection, mature trees, and a garden space just waiting to bloom. Perhaps what truly sets this home apart is its incredible location. Nestled in the sought-after Winter Woods neighborhood in the Seminole County side of Winter Park, you’re just 3.5 miles from the boutiques and bistros of iconic Park Avenue, close to Rollins College, and moments from Winter Park Village, where shopping, dining, and entertainment abound. Whether you're settling into your forever home or making a savvy move into one of Central Florida’s most desirable areas, 1921 Japonica Rd offers the charm, space, and location you've been searching for. Schedule your private showing today and experience the warmth, opportunity, and unbeatable lifestyle this home has to offer. All information provided in this listing, including but not limited to square footage, room dimensions, and property features, is deemed reliable but is not guaranteed. Buyers are advised to conduct their own investigations and due diligence to satisfy themselves regarding the accuracy of all information provided.

1921 Japonica Road, Winter Park
$805,000
3 Beds ⋅ 3 Baths ⋅ Kenilworth Shores Sec 4 SubDv. ⋅ 32792 Zip Code
Welcome to this fabulous Winter Park home tastefully renovated 2022. So inviting from the street -classic front porch with brick accents. From the moment you open the front door, you will notice the thoughtful details- the high ceilings, designer lighting, open floorplan, oversized rooms and beautiful plank floors. The kitchen offers sleek cabinetry, waterfall quartz counters, high end appliances including wine refrigerator. The family room is oversized with wood burning fireplace and French doors leading to backyard. The outdoor space perfect for entertaining with patio with unique turf design, lighting and new vinyl fence for privacy,, Three bedrooms and three renovated baths. All of the bedroom closets have built in cabinetry. There is a seperate 'flex ' space currently used as office. Roof 2022 and water heater new in 2023. Ideal location near sought-after schools , and easy drive to Baldwin Park, downtown Orlando and Park Avenue. This house is a "WOW'-- and truly special.

640 Dunblane Drive, Winter Park
$400,000
3 Beds ⋅ 2 Baths ⋅ Winter Park Estates SubDv. ⋅ 32792 Zip Code
MULTIPLE OFFERS RECEIVED ALL OFFERS DUE SUNDAY 19th 5pm Welcome to your dream home! This charming 3-bedroom, 2-bathroom sanctuary is nestled in a prime location close to the area's finest schools, making it ideal for buyers seeking comfort and convenience. As you step inside, prepare to be captivated by the spaciousness and elegance offered by the vaulted ceilings, creating an airy and inviting atmosphere that sets the tone for relaxation and enjoyment. Recently renovated to perfection, every corner of this home exudes modern sophistication and timeless appeal. The open-concept living area seamlessly blends style and functionality, providing the perfect setting for both intimate gatherings and lively entertaining. Cozy up on chilly evenings beside the electric fireplace, adding warmth and ambiance to your evenings spent indoors. The heart of the home, the kitchen, is a culinary enthusiast's delight, boasting sleek countertops, stainless steel appliances, and ample storage space to inspire your culinary creations. Adjacent to the kitchen, the dining area offers a delightful spot for every meal, bathed in natural light streaming through large windows. The master suite is a private oasis, offering a serene retreat where you can unwind after a long day. Pamper yourself in the luxurious ensuite bathroom, featuring modern fixtures and a spacious shower. Two additional bedrooms provide versatile space for guests, or a home office, ensuring everyone has their own sanctuary to enjoy. Outside, the charm continues with a freshly paved driveway, providing ample parking space for your vehicles. The lush backyard offers endless possibilities for outdoor enjoyment, whether you're hosting summer barbecues, cultivating a garden, or simply relaxing in the sunshine. With its desirable location, impeccable renovations, and thoughtful features throughout, this home is ready and waiting for its new owner to make cherished memories for years to come. Don't miss your chance to make this dream a reality - schedule your showing today!

719 Densmore Drive, Winter Park
$820,000
4 Beds ⋅ 3 Baths ⋅ Preserve At Hawks Crest SubDv. ⋅ 32792 Zip Code
Nestled in the heart of Winter Park's finest gated community awaits your modern masterpiece. Perfectly positioned on a corner lot and spanning over 2,100 square feet of energy-efficient living space, the Pomelo model crafted by Meritage Homes embodies the epitome of contemporary living. Upon entering through the front door, you will be greeted by high ceilings and a beautiful entryway. The expansive kitchen boasts 42-inch cabinets, sleek appliances, Quartz countertops, double ovens, a custom pantry storage system, an elegant kitchen island with luxurious pendant lights and opens up beautifully to your living and dining space. The owner's suite features a large walk-in closet with custom storage, an en-suite bathroom with double vanities, and a glass-enclosed shower with a premium showerhead system. This thoughtfully-designed layout includes three additional bedrooms, two additional full bathrooms, and a generously-sized laundry room equipped with custom built-in features. Step outside onto the covered lanai, featuring a privacy screen and a TV outlet, perfect for hosting gatherings and entertaining guests. Beyond, you'll find lush landscaping with custom lighting, bespoke elements adorned with a magnificent saltwater pool and spa, offering an abundance of outdoor enjoyment. Residents of Hawk's Crest indulge in a thoughtfully planned community featuring a resort-style swimming pool, virtual guard gate, clubhouse, fitness center, splash pad, playgrounds, dog park, and access to Lake Howell. Park Maitland Preschool, Kelly's Ice Cream and Foxtail Coffee shop are located at the front of the neighborhood for added convenience. An exclusive respite, this home exemplifies a refined lifestyle for those who appreciate peaceful and convenient living.

2079 Laurelwood Way, Winter Park
$2,050,000
5 Beds ⋅ 8 Baths ⋅ Talman Mews Ph 2 SubDv. ⋅ 32792 Zip Code
Welcome to the epitome of luxury living in Winter Park, FL, situated within highly rated Seminole County Public school district. This FULLY FURNISHED magnificent multi-generation compound occupies not one, but two expansive lots within a highly sought-after Talman Mews community where it provides unparalleled convenience and lifestyle. The estate boasts an impressive 7762 square feet of exquisitely designed living space, ensuring comfort, style, and absolute grandeur for you and your loved ones. Upon entering, you will be greeted by mature Mediterranean-inspired landscaping that sets a welcoming tone. From the moment you step inside, the sheer grandeur of this palatial residence envelops you. The impressive entrance invites you under the portico, leading into a two-story, oversized foyer adorned with a beautiful staircase. 5 spacious bedrooms all come with en-suite baths and walk-in closets, including a lavish primary suite, everyone will have their own sanctuary to retreat to. For those with a passion for culinary delights, the true Chef's kitchen boasts bespoke cabinetry and state-of-the-art appliances, including a gas range and a convenient Butler's pantry, making hosting and entertaining effortless. The kitchen seamlessly flows into the eat-at bar and the expansive family room, accentuated with custom built-ins, creating the perfect space for strengthening bonds with loved ones. The spacious primary bedroom and its luxurious spa-like en-suite are conveniently situated on the ground floor of the main home, providing the ultimate haven for relaxation and rejuvenation. Another generously sized bedroom with its own en-suite bathroom is also located on the ground floor, with its own private entrance. The formal living and dining spaces exude elegance and are ideal for intimate gatherings. Additionally, a distinguished executive office is located on the main floor, offering a private sanctuary for those who work from home. Upstairs, two additional bedrooms with walk-in closets, and two opulent bathrooms await, ensuring that every family member or guest is treated to the utmost comfort and luxury. The home is equipped with an elevator, providing easy access to the upper floor for guests who require it, ensuring everyone can fully experience the majesty of this residence. The bonus room is a haven of relaxation and leisure, perfect for a pool table, media room, or as a teenager's idyllic retreat. A convenient snack bar, complete with a sub-zero fridge, is already in place, offering easy access to refreshments without needing to leave the comfort of the room. Unwind and soak up the Florida sunshine by the sparkling swim pool and spa, perfect for refreshing dips during warm summer days. Host unforgettable gatherings and create lasting memories as you utilize the convenient outdoor kitchen, complete with appliances and a spacious seating area. From sizzling barbecues to al-fresco dining experiences, this outdoor haven allows you to take full advantage of the year-round favorable climate in Winter Park. The U-shaped lusty green grass area shaped around the compound features gates that can separate it into three separate yards, creating an ideal space for your beloved animals to play and roam freely. The private lanai even includes an outdoor shower/grooming room specifically designed for your furry friends. Don't miss the opportunity to call this extraordinary property yours and elevate your living experience to new heights.

2156 Talman Court, Winter Park
$515,000
4 Beds ⋅ 2 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code
Welcome to this meticulously maintained 4 bedroom 2 bathroom Winter Park gem, lovingly cared for by the same attentive owner for 50 years. Nestled within the coveted Winter Park Pines neighborhood, this residence enjoys a premium location adjacent to the picturesque Cady Way Trail. As you approach the home, the meticulously crafted paver driveway sets the tone for what's to come. Plantation shutters adorn the living spaces. Rich laminate wood flooring & ceramic tile weave a tapestry of elegance throughout that leads to a beautifully upgraded kitchen adorned with granite countertops and modern stainless-steel appliances. The ample size of the bedrooms ensures cozy retreats, while the office features built-in shelving that adds both functionality and charm. This residence follows a smart split plan layout, offering privacy and an efficient use of space. But the location is truly unbeatable. You're just steps from unique neighborhood amenities such as Winter Pines Golf Course, Ward Park, Showalter Field, Cady Way Community Pool, Pickle Ball Courts & Winter Park Advent Health Complex. TOP RATED Winter Park schools, Brookshire Elementary & Winter Park High School, are both located just a few blocks over. In addition the neighborhood amenities, it’s just a short drive from Park Avenue Winter Park, a vibrant shopping and dining district with over 100 stores and restaurants and home to a variety of art galleries, museums, theaters, and outdoor cafes. Twenty minutes from UCF & Downtown Orlando. 35 minutes from Universal & Disney and only an hour from the beach allowing you to enjoy the best of both worlds, luxury living and prime Florida living. Important notable features: NEW ROOF(May 2022), NEW SOD (2020) NEW FENCE ALONG BACK OF HOUSE, UPGRADED SECURITY SYSTEM (2020) NEW FARMHOUSE GARAGE DOOR(2020) alongside an array of other thoughtful upgrades made over the years.

527 Cornwall Road, Winter Park