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$400,000
4 Beds ⋅ 2 Baths ⋅ Winter Park Pines Rep SubDv. ⋅ 32792 Zip Code
Needs TLC. Property is being sold as-is. Age of big ticket items unknown. Buyer/buyer's agent to verify condition of property via walkthrough. Limited-service listing - Please see realtor remarks for showing instructions.

2833 Prince John Road, Winter Park
$425,000
3 Beds ⋅ 3 Baths ⋅ Autumn Glen SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. Location is Everything. If you want the best home in the best location look no further. This three bedroom two and half bathroom home is located in the much desired Autumn Glen community. The home is perfect and has a very flexible floorplan with the 3rd bedroom currently configured as a loft with a closet for the work from home person and can be easily converted to a third bedroom if needed. The first floor features a spacious dining area and a step down into a large living room with sliders to pool and patio. The gourmet kitchen with eating space includes upgrades like Custom cabinets, Stainless appliances , reach in pantry breakfast bar and tile flooring all overlooking the living/dining area. The primary suite is located downstairs and features a walk in closet with hidden storage access under the stairs, updated primary bath with with upgraded vanity, custom lighting and garden tub. Upstairs features a large guest bedroom, updated guest bath and the loft than can easily converted to a third bedroom. Some of the updates on this home include, Newly painted interior, home has been replumbed and newer roof. Moving outside to the beautiful open air pool with spill over spa framed with tropical palm trees, banana tree, custom deck, additional storage shed, updated landscaping and all this surrounded by a fully fenced yard. The fenced yard provides privacy and room to enjoy the outdoors. The community is located just around the corner from Red Bug Elementary, Tuskawilla Middle and Lake Howell High School.. Other community features include tennis/pickleball courts, a playground, and a gazebo overlooking the community pond—perfect for bringing your fishing pole. If you're looking for the right house in the right location, this is the one. Autumn Glen is ideally located just around the corner from Red Bug Elementary, Tuskawilla Middle, and Lake Howell High School. Community amenities include tennis and pickleball courts, a playground, and a gazebo overlooking the community pond—perfect for relaxing or casting a fishing line. If you’re looking for the right home in the right location, this is the one.

1816 Meadowgold Lane, Winter Park
$465,000
4 Beds ⋅ 3 Baths ⋅ Bear Gully Forest SubDv. ⋅ 32792 Zip Code
Price reduced!! Spacious Winter Park home on over a half acre with no rear neighbors!. In Bear Gully Forest community and has over 2,000 s/f- with a Living Room, Dining Room, Eat-in Kitchen and more. The home's fully-equipped kitchen has excellent cabinet space and appliances that include a stove, microwave, and dishwasher. An inside laundry room has a washer/dryer combination for your convenience. Bedroom with 1/2 bath upstairs. Roof new in 2018 with a 10 year full warranty.

4190 Bear Gully Road, Winter Park
$469,900
3 Beds ⋅ 2 Baths ⋅ Garden Lake Estates Unit 3 SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. Welcome to this beautifully updated 3-bedroom, 2-bath home with a New Roof 2021, screened-in pool, ideally located in the heart of Winter Park. Step inside to a fresh, move-in-ready feel with new flooring throughout, new light fixtures, new windows, and new doors—all thoughtfully selected to give the home a clean, modern look. The open, inviting layout is perfect for everyday living and entertaining, and the screened pool area creates a private Florida retreat for relaxing weekends, family gatherings, or evening swims—without the bugs. Conveniently close to Winter Park’s shopping, dining, parks, and local favorites, this home offers the best of Central Florida living in a prime location. More photos coming soon—don’t miss your chance to see this one!

1280 Gladiolas Dr, Winter Park
$475,000
3 Beds ⋅ 2 Baths ⋅ Park Manor First Add SubDv. ⋅ 32792 Zip Code
This charming and affordable Winter Park abode offers its next owners loads of possibilities: from building your own dream home on the best lot in the neighborhood to enjoying what’s already here. 2042 Yorkshire Drive is a nearly quarter acre (.24) corner lot in desirable Winter Park with sought-after schools: Lakemont Elementary, Maitland Middle, and Winter Park High. Beautiful views from the kitchen window and dining room overlook the charming pond of The Mayflower Winter Park, and imagine what a view could be had from the second story of a new home built on the lot. Luxury homes are being built all around in this neighborhood. Currently, this 3 bed, 2 bath home has approximately 1,700 sq ft including a large mud-room/utility room and a new bonus room (extra 120+ sq ft not included in property record sq ft) leading to the backyard covered porch. NEW Roof 2023, NEW HVAC 2023, updated electric and replumb with CPVC. Stepping inside the great room, beautiful hardwood floors and wood burning fireplace with stacked stone surround are sure to please. An ample size dining room leads to the updated kitchen with stainless steel appliances, granite counter tops, and white wood cabinets. Down the main hallway are 2 guest bedrooms, beautifully updated hall bathroom with tub/shower combo, and the primary bedroom with updated ensuite with walk-in shower. Outback, the covered porch is perfect for your home grill master, and the large yard is ideal with space for kids to play on the premium turf and for pets to run around in the fully fenced real grass space. Not on a cut-through street, so solitude and quiet abound despite the close location to the best of Winter Park – YMCA Fitness is just around the corner, as is Sprouts, Publix, the shops and restaurants of Park Avenue (2 miles away), and Winter Park Village (10-minute drive). Zoned A-1 with no HOA or CDD, live in the property as-is, rent it out, or tear it down and build your dream home in this fabulous location. Lot dimensions: 136x80x110x61.

2042 Yorkshire Drive, Winter Park
$440,900
4 Beds ⋅ 2 Baths ⋅ Winter Park Forest SubDv. ⋅ 32792 Zip Code
Welcome to 824 Garrett Court, a beautifully updated 4-bedroom, 2-bath home located on a quiet cul-de-sac in the highly desirable Winter Park Forest community. This bright and spacious residence is one of the only homes listed in this sought-after neighborhood in 2025. The interior features luxury vinyl flooring throughout, 4inch baseboards, an updated kitchen with stainless steel appliances (including a gas range and gas water heater) quartz countertops and fresh lighting throughout. Additional upgrades include newer windows and doors, a roof replaced in 2019, AC replaced in 2018, and ductwork encapsulated in 2024 for enhanced efficiency and air quality. The exterior is equally impressive, situated on a 0.23-acre lot with zoysia grass (extensive sprinkler system) and fruit trees throughout the entire yard. Enjoy peace of mind with a new fence installed in 2019, as well as gutters and fresh exterior paint. The screened-in back porch provides the perfect space for year-round outdoor living. Winter Park Forest is known for its close-knit community, tree-lined streets, and prime location. It sits just 5 minutes from Publix, Sprouts, Aldi and Costco and less than ten minutes from Park Ave and downtown Winter Park. The home is zoned for top-rated Lakemont Elementary, Maitland Middle, and Winter Park High School. Don’t miss this rare opportunity to own in one of Winter Park’s most coveted neighborhoods.

824 Garrett Court, Winter Park
$439,900
3 Beds ⋅ 3 Baths ⋅ Winter Park Estates SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. Opportunities like this are rare. Perfectly suited for multi-generational living, mother-in-law suite potential, or rental income, this versatile POOL home sits on an oversized lot with no HOA in one of Central Florida’s most desirable locations — Winter Park. The flexible floor plan allows for comfortable separation of living spaces, making it ideal for extended family, guests, or income-producing arrangements, while still maintaining a natural sense of connection throughout the home. All major high-ticket items have already been taken care of, offering true peace of mind for years to come. Updates include a newer roof 2022, new AC system 2025, new water heater 2025, energy-efficient double-pane windows 2025, resurfaced pool with a new pool pump 2025, fresh interior and exterior paint 2025, and new quality flooring throughout. The updated kitchen features 42-inch shaker cabinetry with soft-close drawers, generous storage, and new appliances, creating a functional and inviting space for daily living and entertaining. Step outside to your private outdoor retreat—ideal for gatherings, relaxation, or future enhancements. The location truly elevates this property. Just minutes from Rollins College, Full Sail University, AdventHealth Winter Park Hospital, and the Cady Way / Gateway Trail. Everyday conveniences are nearby, including Sprouts Farmers Market, Publix, Costco, boutique shopping, cafés, and fine dining along Park Avenue and Baldwin Park. Quick access to major highways ensures easy connectivity throughout Central Florida. Zoned for highly regarded Winter Park schools and surrounded by consistent buyer demand, this home offers a compelling combination of versatility, extensive upgrades, and a prestigious address. Call for your private tour today!

2835 Bongart Road, Winter Park
$499,000
4 Beds ⋅ 2 Baths ⋅ Winter Woods Unit 01 SubDv. ⋅ 32792 Zip Code
Under contract-accepting backup offers. PRICE REDUCED!!! ROOF 4 yrs. old, newer A/C, In-ground Pool. Enclosed Patio — a beautifully maintained turnkey home nestled in the heart of Winter Park, one of Central Florida’s most sought-after communities. Surrounded by renowned golf courses, top-rated Seminole County schools, lush parks, and family-friendly neighborhoods, this exceptional residence offers the perfect blend of comfort, convenience, and the elevated Winter Park lifestyle buyers are searching for. This spacious 4-bedroom + office home is completely move-in ready and vacant — just bring your furniture and clothes and start living! From the moment you walk through the front door, you’ll love the bright open-concept layout filled with natural light, updated finishes, granite countertops, modern appliances, and an inviting wood-burning fireplace that creates the perfect family gathering space. Designed for entertaining and Florida living, the oversized Florida room/lanai overlooks a stunning private pool and beautifully landscaped fenced backyard, creating the ultimate indoor-outdoor experience. Whether hosting weekend BBQs, pool parties, holiday gatherings, or simply relaxing after work, this home was built for making memories. Additional highlights include: • 2,092 square feet of living space • 4 bedrooms plus dedicated office/bonus room • Large open kitchen with granite countertops and abundant cabinet space • Spacious primary suite with pool views • Huge covered Florida room perfect for entertaining • Private in-ground pool • Full irrigation system and landscaped yard • Wood-burning fireplace • NO HOA • Attached 2-car garage plus additional parking • Fully fenced backyard for privacy and pets • Move-in ready condition Located in the highly desirable Winter Woods/Lake Howell area, this home is centrally positioned near major highways including SR-417, I-4, Howell Branch Road, and SR-436, making commuting to Downtown Orlando, Winter Park Village, UCF, Orlando International Airport, beaches, shopping, dining, and all Central Florida attractions incredibly convenient. Winter Park is known for its charm, tree-lined streets, upscale dining, boutique shopping, beautiful golf communities, and strong sense of community. Families love the area for its excellent schools, nearby parks, recreational amenities, and safe neighborhood atmosphere. This is more than just a home — it’s a lifestyle opportunity in one of Florida’s premier communities.

2217 Sussex Road, Winter Park
$426,000
3 Beds ⋅ 3 Baths ⋅ Enclave At Hawks Crest SubDv. ⋅ 32792 Zip Code
**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Nestled in the heart of Winter Park, 2224 Shadowland Loop offers a beautiful blend of comfort, style, and low-maintenance living in this spacious 3-bedroom, 3-bathroom townhouse. The interior features an inviting open layout with high ceilings, modern finishes, and tile and carpet flooring all throughout. The well-appointed kitchen flows effortlessly into the main living and dining areas, creating a seamless environment for entertaining or everyday living. All three bedrooms include generous walk-in closets, while the primary suite offers a peaceful retreat with its own private bathroom and serene ambiance. A versatile loft on the second floor adds valuable flex space that is ideal for a home office, media area, or playroom. Outside, the home offers a cozy enclosed rear patio perfect for relaxing, dining outdoors, or enjoying your morning coffee in privacy. A spacious two-car garage provides convenience and additional storage. The community surrounding Shadowland Loop is quiet, welcoming, and beautifully maintained, with tree-lined streets and easy access to the best of Winter Park. Residents enjoy proximity to top-rated schools, charming parks, boutique shopping, vibrant dining spots, and the area’s beloved lakes and recreation. With its thoughtful design, modern amenities, and exceptional location, this townhouse delivers the ideal Winter Park lifestyle.

2224 Shadowland Loop, Winter Park
$420,000
3 Beds ⋅ 2 Baths ⋅ Bel Aire Pines SubDv. ⋅ 32792 Zip Code
Welcome to this beautifully updated Winter Park home offering modern finishes, strong mechanical upgrades, and a spacious open layout. Major improvements include a brand-new roof installed in October 2025, new windows and sliding door (2024), and a new A/C system (2020), providing long-term comfort and efficiency. Inside you’ll find new porcelain tile flooring installed in 2022, neutral interior tones, and abundant natural light flowing through the main living areas. The kitchen was fully renovated in 2022 and features upgraded cabinetry, corian countertops, pantry storage, and stainless steel appliances. All bedrooms include walk-in closets, and the primary suite showcases an updated dual-sink vanity and a walk-in shower, while the guest bath offers granite countertops, a tub/shower combo, and direct access to the screened lanai. Stepping outside, the property sits on a generous corner lot with mature landscaping and multiple outdoor spaces perfect for entertaining. The backyard features new pavers added in 2024, a covered outdoor grill/kitchen station, a gazebo, fruit trees, garden beds, an enclosed lanai, and a storage shed. The home also offers a shaded carport, a two-car garage, an irrigation system spourced from a private well, and a beautifully maintained front exterior with stone façade and lush greenery. To complete the package, this residence enjoys a prime Winter Park location just minutes from Costco, Publix, Full Sail University, UCF, Rollins College, Baldwin Park, Downtown Orlando, 417, Orlando Executive Airport, shopping, dining, and numerous conveniences.

3236 Knottypine Avenue, Winter Park
$400,000
3 Beds ⋅ 2 Baths ⋅ Suburban Homes SubDv. ⋅ 32792 Zip Code
Welcome to this beautifully renovated 3-bedroom, 2-bath home located in Seminole County — a rare find in Winter Park with NO HOA OR CDD! This delightful residence offers a perfect blend of modern updates and practical features throughout. Enjoy bright, inviting living spaces, a functional layout, and a master suite featuring its own private exterior door, offering added convenience for guests, multigenerational living, or potential rental use. This home has been thoughtfully renovated from top to bottom, featuring modern appliances, fresh interior and exterior paint, and a new septic system (2025) — giving you peace of mind for years to come. Additional Upgrades Completed in 2024 Include: - New roof (2025) - New electric panel (2024) - Hurricane-rated, energy-efficient double-pane windows - New plumbing - New water heater (2024) - New interior & exterior doors with updated hardware - New bathroom fixtures - New soffit venting - Motion-activated exterior lighting - All-new blinds throughout the home - Fully fenced backyard perfect for pets, privacy, and entertaining Located in a quiet Winter Park neighborhood close to great schools, shops, dining, and major roadways, this beautifully updated home is truly move-in ready. Offered at $404,990, this property delivers exceptional value, comfort, and convenience. Don’t miss your chance — schedule your showing today!

5357 Orange Avenue, Winter Park
$445,000
3 Beds ⋅ 2 Baths ⋅ Winter Park Pines Merrie Oaks SubDv. ⋅ 32792 Zip Code
Welcome home to this 3-bedroom, 2-bath residence featuring a spacious 2-car garage and a long list of valuable updates. Enjoy peace of mind with a re-roof (2017), whole-home re-plumb with Pex and PVC (2024), new A/C system (2024), and new modern ceramic tile flooring in the kitchen, family room, foyer and hallway (2024). The hot water heater was replaced in 2022, and the home is enhanced with energy-efficient double-pane argon gas windows and a sliding glass door (2014). Inside, you’ll find a bright, open layout perfect for everyday living and entertaining. The upgraded windows fill the home with natural light while improving comfort and efficiency. The spacious kitchen, inviting living areas, and well-appointed bedrooms offer flexibility for any lifestyle. Outside, the property features a private fenced yard ideal for relaxation or outdoor gatherings. Located in desirable Winter Park, you’re just minutes from top-rated schools, shopping, dining, and parks. This move-in-ready home combines modern upgrades with a prime location—an exceptional opportunity you won’t want to miss!

2743 Merrie Oaks Road, Winter Park
$425,000
3 Beds ⋅ 2 Baths ⋅ Eastgate Sub SubDv. ⋅ 32792 Zip Code
The house is located in great location and features 3 bedrooms, 2 bathrooms. It sits on a corner lot and offers high ceilings throughout.

1909 Edwin Boulevard, Winter Park
$460,000
3 Beds ⋅ 3 Baths ⋅ Winter Park Estates SubDv. ⋅ 32792 Zip Code
Welcome home to this charming 3-bedroom, 3-bathroom single-family residence nestled in the quiet, established neighborhood of Winter Park Estates. Boasting the highly desirable Winter Park school district, this location offers both prestige and tranquility, yet is conveniently located near major roads which make getting around town a snap! Nearby restaurants and entertainment include Aloma Bowl, Aloma Cinema Draft House, and Park Ave. Inside, the spacious, open layout features a dedicated formal dining room, perfect for hosting, and a versatile bonus room that makes an ideal, secluded home office or flexible living space. The laundry room includes a fully plumbed 3rd bathroom. Enjoy the peace of mind provided by a newer HVAC system, water heater, and the modern convenience of recently updated bathrooms. Residents will enjoy the two-car carport equipped with a Tesla charger and nice sized shed in back for additional storage. Entertain guests or enjoy quiet evenings on the covered back patio, in the sprawling, fully fenced backyard. This home offers the quintessential Florida lifestyle—comfort, style, and an incredible setting. Don't miss this opportunity!

714 Denton Road, Winter Park
$470,000
3 Beds ⋅ 2 Baths ⋅ Kenilworth Shores Sec 03 SubDv. ⋅ 32792 Zip Code
Located in an established Winter Park neighborhood, 502 Dunblane Drive offers an opportunity for those looking to build new or invest in a property with plenty of potential. This 3-bedroom, 2-bath home sits on a well-sized lot in the 32792 area of Winter Park and features a private backyard, perfect for relaxation, gardening, or entertaining. The property is ready for a full renovation or reconstruction, making it an ideal canvas for builders, investors, or anyone looking to create a custom residence from the ground up. The existing structure provides a basic footprint, but the true value lies in the land and the flexibility it offers. Whether you envision designing a modern new build, developing an income-producing property, or taking on a remodel, this lot serves as a canvas for your ideas. Located just minutes from everyday conveniences, the property offers quick access to shopping, dining, parks, and reputable Winter Park schools. Nearby roadways make commuting simple, while the surrounding community provides a peaceful residential setting with strong long-term appeal. With its favorable location, private backyard, and extensive potential for redevelopment, 502 Dunblane Drive offers a unique opportunity to design your ideal home in a well-established Winter Park community.

502 Dunblane Drive, Winter Park
$418,000
3 Beds ⋅ 2 Baths ⋅ Lakemont Heights SubDv. ⋅ 32792 Zip Code
Visit this charming one-story Winter Park home across from the Winter Park YMCA. Enter this adorable single-story home with a comfortable primary suite and two oversized bedrooms. The home boasts a wonderful backyard for outdoor living and a welcoming front porch that welcomes you in. The home has new Hybrid vinyl laminate throughout the home and terrazzo flooring in the baths. When you enter the front door, you will find large front windows and plenty of natural light. Enter through the French doors into the oversized backyard, offering ample space for gathering and play. Top-rated schools, no HOA, across from Winter Park YMCA and Phelps Park. This house is minutes away from Interstate 4 and major roadways.

1030 N Lakemont Ave., Winter Park
$385,000
3 Beds ⋅ 2 Baths ⋅ Garden Grove SubDv. ⋅ 32792 Zip Code
Lovely pool home in the desirable community of Winter Park, conveniently located near shopping, medical offices, and UCF. Freshly painted inside and out, this home features a kitchen with tile and granite, and all appliances included. The kitchen opens to the great room, which offers easy-care tile flooring throughout the main living areas. Enjoy the enclosed porch (not included in the square footage) and a spacious backyard with a large swimming pool and vinyl privacy fencing. No HOA. Close to Winter Park shopping and major conveniences.

5563 Garden Grove Circle, Winter Park
$450,000
4 Beds ⋅ 3 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code
Priced to sell! Welcome to this 4-bedroom, 3-bathroom home offering 1,829 sq. ft. of inviting living space in one of Winter Park’s most desirable neighborhoods. Inside, you’ll find a spacious family room with plenty of natural light from large windows, and elegant French doors leading to the porch. The split floor plan of this home provides privacy and comfort for the primary suite that features its own set of French doors that open to the screened porch, along with an updated en-suite bathroom. Additional highlights include ceiling fans in all bedrooms, stylish window shutters throughout, and an updated guest bathroom. Outside, enjoy relaxing on the screened porch overlooking the peaceful yard, perfect for morning coffee or evening gatherings. The home also offers a two-car garage and sits on a quiet street surrounded by well-kept homes. Located just 1 mile from Winter Park High School, under 4 miles to Park Avenue and Rollins College, and just 10 miles from Orlando International Airport, this home offers both comfort and convenience. Golf enthusiasts will appreciate being just minutes from Winter Park Pines Golf Course. You’ll also love being close to top-rated schools, shopping, and dining. This home blends charm, functionality, and an unbeatable location—schedule your showing today!

639 Friar Road, Winter Park
$425,000
3 Beds ⋅ 2 Baths ⋅ Winter Woods Unit 03 SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. Welcome home to 2218 King Richards Court — a beautifully updated pool home tucked away on a quiet cul-de-sac in the highly desirable Winter Woods community of Winter Park. This charming 3-bedroom, 2-bathroom residence offers the perfect blend of modern updates, comfort, and location. Step inside and immediately notice the brand-new flooring that flows throughout the spacious living areas, complementing the home’s open and inviting layout. The fully remodeled kitchen (2025) features all-new stainless steel appliances, sleek cabinetry, quartz countertops, and stylish finishes — a true showpiece for anyone who loves to cook or entertain. Enjoy peace of mind knowing the roof, HVAC, and water heater have all been updated within the last 4 years, ensuring years of worry-free living. The primary suite offers a private retreat with an en-suite bathroom, while two additional bedrooms provide flexibility for guests, a home office, or family. Outside, step through sliding glass doors to your screened-in patio and sparkling pool, surrounded by lush landscaping and a fully fenced backyard — ideal for relaxing or hosting gatherings year-round. Additional highlights include a two-car garage, block construction, no HOA, and a prime location close to downtown Winter Park, Park Avenue shopping and dining, UCF, Rollins College, and major roadways for easy commuting. Whether you’re a first-time homebuyer, downsizing, or looking for a move-in-ready property in a sought-after neighborhood, this Winter Park gem truly has it all.

2218 King Richards Court, Winter Park
$505,000
4 Beds ⋅ 2 Baths ⋅ Tamarak SubDv. ⋅ 32792 Zip Code
Welcome to this charming 4 bedroom, 2 bath home located in the desirable Charter Oaks subdivision of Winter Park. The centrally located kitchen features stainless steel appliances, granite countertops, and a breakfast bar that seamlessly connects to the family room. Enjoy cozy evenings by the wood burning fireplace or host gatherings in the separate dining room and spacious living room. Step outside to your own private retreat with a fully fenced yard and a covered screened patio with pool, perfect for year round entertaining and relaxation. This home also includes fully owned solar panels offering energy efficiency and reduced utility costs. Nestled in a quiet tree lined neighborhood with no HOA, this home provides the perfect balance of peace and convenience. You will be just minutes from Park Avenue, boutique shopping, world class dining, and the scenic Winter Park Chain of Lakes. Families will appreciate access to top rated schools, nearby parks, and recreational opportunities. With easy access to major highways and a short drive to downtown Orlando, this location simply cannot be beat.

1691 Bomi Circle, Winter Park
$450,000
3 Beds ⋅ 2 Baths ⋅ Kenilworth Shores Sec 01 SubDv. ⋅ 32792 Zip Code
Value is in the land/lot with potential for a renovation/remodel. Excellent opportunity to own a block home in Winter Park with a preexisting pool and some valuable upgrades including tankless water heater, newer washer/dryer, and newer HVAC.

443 S Lakemont Avenue, Winter Park
$425,000
3 Beds ⋅ 2 Baths ⋅ Wrenwood Unit 3 3rd Add SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. Beautifully Renovated 3-Bed, 2-Bath Home in Winter Park!!! Experience modern living at its finest in this fully renovated 3-bedroom, 2-bathroom home located in the heart of Winter Park. Recently updated with a new roof (installed within the last six months), HVAC systembupdated within the last few years, and upgraded plumbing, this residence offers both peace of mind and contemporary style. The interior features a luxurious open-concept design with premium finishes, designer fixtures, and a fully remodeled kitchen complete with custom cabinetry and stainless steel appliances. The spacious primary suite includes a beautifully updated ensuite bathroom. Perfectly situated near A-rated schools, premier shopping, dining, and entertainment, this move-in-ready home delivers the ideal blend of elegance, comfort, and convenience in one of Central Florida’s most desirable locations.

5201 Ardmore Drive, Winter Park
$435,500
3 Beds ⋅ 2 Baths ⋅ Garden Lake Estates Unit 1 SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. Welcome to this stunning Winter Park pool home, offering 3 bedrooms and 2 bathrooms across 1,668 square feet of thoughtfully designed living space. Upon entering, you are greeted by a spacious, open living area where the living and dining rooms flow seamlessly together, creating a perfect space for entertaining or relaxing with family. The kitchen features stainless steel appliances, abundant cabinetry, and generous counter space, complemented by a breakfast nook that opens to the family room. A sliding glass door leads from the family room to the enclosed Florida room, providing a bright, versatile space to enjoy year-round. The split bedroom floorplan ensures privacy, with the primary suite boasting an en suite bathroom complete with a walk-in shower. Step outside to a beautifully landscaped backyard with an in-ground pool and a pergola, ideal for outdoor gatherings or quiet afternoons. The enclosed Florida room with A/C overlooks the yard, making it perfect for indoor-outdoor living. Sitting on over a quarter acre, this home offers ample space for relaxation and recreation. Recent upgrades include fresh paint, new carpet, a brand-new hot water heater, and a new kitchen sink and faucet. Conveniently located near grocery stores, restaurants, and with easy access to highways, UCF, downtown Orlando, and all the city has to offer, this home combines comfort, style, and location in one exceptional package. Don’t miss the opportunity to make this Winter Park gem your new home. Mortgage savings may be available for buyers of this listing.

1630 Gladiolas Drive, Winter Park
$458,000
4 Beds ⋅ 3 Baths ⋅ Bel-Aire Pines, Unit Two SubDv. ⋅ 32792 Zip Code
Virtually Staged. Stunning Two-Floor Home in Coveted Winter Park School District Immaculately maintained and truly move-in ready, this unique two-story residence features distinct living quarters with private entrances to both levels. The main floor offers a spacious split-bedroom layout with three bedrooms and two full baths, including a primary suite with an en-suite bathroom and generous walk-in closet. The fully equipped kitchen boasts newer appliances and opens to a bright living area. The expansive 800 sq. ft. upper level functions as a self-contained living unit, ideal for multi-generational arrangements, home offices, or rental income potential. This versatile space includes one bedroom, a full bathroom, a private balcony, and a full open-concept living and dining area complete with a full-size refrigerator and stove. Located in the highly rated Winter Park School District, this home offers the perfect blend of top-tier education and Central Florida lifestyle. Residents enjoy easy access to world-class entertainment, situated just 26 miles (approx. 35 minutes) from Walt Disney World. Additional features include a large two-car garage with washer/dryer hookups, ample driveway parking, fresh interior paint, and a brand-new roof with a transferrable warranty. All major systems are well-maintained and in excellent working condition.

3312 Heartwood Avenue, Winter Park
$470,000
3 Beds ⋅ 2 Baths ⋅ Garden Lake Estates Unit 2 SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. **2025 ROOF** Pride of ownership shines throughout this well maintained 3 Bedroom + OFFICE home, ideally situated on a spacious corner lot in a quiet, neighborhood with NO HOA. With 2,031 square feet of living area including the enclosed porch, this property offers exceptional flexibility and room to grow. Step inside and immediately feel at home in the bright, open layout featuring soaring vaulted ceilings, neutral tones, and wood look luxury vinyl plank flooring that flows seamlessly throughout the home. The living room welcomes you with abundant natural light and a sense of openness, leading into a dedicated formal dining area that overlooks both the pool and main living areas, perfect for family gatherings or entertaining friends. The updated kitchen has been tastefully renovated with custom cabinetry, quartz countertops, and stainless steel appliances, creating a functional space that opens directly to the family room. Whether you’re preparing meals, watching a movie, or keeping an eye on the pool, this layout ensures you’re always part of the action. From the family room, sliding glass doors open to the expansive enclosed porch, a versatile bonus area surrounded by windows on two sides that let in plenty of light and gentle Florida breezes. This space offers countless possibilities — use it as a game room, second living room, home gym, or entertaining space overlooking the pool. Outside, enjoy year round relaxation in your screened pool and patio area, perfect for cooling off on warm afternoons or hosting weekend barbecues. The vinyl fence adds privacy and a clean, low maintenance look to the backyard. The split bedroom floor plan ensures comfort and privacy for all. The primary suite features a newly renovated bathroom with stylish finishes, while the secondary bedrooms are generous in size and share a well appointed guest bath. The dedicated office provides a quiet retreat for working from home, studying, or hobbies. Additional highlights include an oversized side-entry garage with built-in storage shelving and a workbench, ideal for projects or extra storage space. Major updates have already been taken care of for peace of mind — including a new roof (2025) and new pool screens (2025). This is a truly special home that combines modern updates, flexible living spaces, and a private outdoor retreat all in a desirable location close to shopping, dining, and top-rated schools. Schedule your private tour today!

1931 Aster Drive, Winter Park
$427,500
3 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 15 SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. Price ENHANCEMENT! The best value in the area. Do not miss out on the opportunity to be the next owner of Conifer Avenue! This POOL home is amazing in every way and is truly a must see! Original Owner with incredible pride of ownership. Brand NEW Roof, Brand NEW Water Heater 2025, HVAC 2020, entire replumb and newer windows throughout. Nestled in the highly coveted community of Eastbrook in Winter Park. A perfect location just minutes to everything. This residence boasts an array of desirable features. As you stroll down the beautiful walkway into the stunning foyer with striking chandelier, you are mesmerized by the beauty and flow of home. Separate formal dining room and expansive formal living area creating a stylish, classic feel. Three bedrooms and two full baths with oversized primary bedroom inviting French Doors leading you to garden and pool deck. Large kitchen-family combo. Kitchen centered between airy family room and spacious formal dining room. Striking stainless steel appliances. Gorgeous tile flooring throughout combining durability and elegance. Beautiful French Doors leading out to lanai porch and open swimming pool with large deck. Close to a quarter acre of land completely fenced for your fury family. Very large, screened in lanai with fabulous swimming pool. Oversized 2 car garage with an abundant of storage options both inside and out. Comes with washer and dryer. This is the ideal entertainment home. What more could you ask for…I-4 and 417 minutes away for Disney or a day at the Beach. Offering supermarket, restaurants, shopping and so much more. Close to Historical Downtown Winter Park and desired Park Avenue with weekly Farmer’s Market. Then you have the convenient SunRail taking you around Central Florida. Excellent A-Rated Seminole County Schools. Location, Location, Location. Welcome Home!!!

2152 Conifer Avenue, Winter Park
$455,500
3 Beds ⋅ 2 Baths ⋅ Greenview At Winter Pines SubDv. ⋅ 32792 Zip Code
This property is currently under contract.

1317 Medinah Court, Winter Park
$445,000
3 Beds ⋅ 3 Baths ⋅ Enclave At Hawks Crest SubDv. ⋅ 32792 Zip Code
Welcome to this beautifully designed, move-in-ready townhome— the largest end-unit in one of Winter Park’s most sought-after gated communities! This spacious townhome is conveniently located in the gated community of Hawks Crest, offering 2,312 sq ft of low-maintenance living. With 3 bedrooms, 2.5 bathrooms, a 2-car garage, filled with natural light thanks to abundant windows and soaring ceilings. The paved driveway and lush landscaping welcome you home. Step inside to find a flex space ideal for a home office, den, or second living area. The open-concept main level boasts 9-foot ceilings and seamlessly connects the expansive living room, dining area, and chef-style kitchen complete with quartz countertops, shaker cabinetry, stainless steel appliances, and a large center island perfect for entertaining. Glass sliders lead to the covered patio perfect for your morning coffee or relaxing evenings outdoors. Upstairs, a spacious loft provides a versatile bonus area—great for a media room, playroom, or home gym. The oversized primary suite impresses with tray ceilings, a spa-like en-suite bathroom featuring dual vanities, a walk-in shower, private water closet, and a generous walk-in closet. Two additional bedrooms also offer walk-in closets and share a stylish full bathroom. A conveniently located upstairs laundry room (washer and dryer included) completes the upper level. Residents of Hawks Crest enjoy access to a suite of resort-style amenities including a community pool, playgrounds, parks, picnic areas, and more. Ideally located just steps from Park Maitland Preschool and neighborhood favorites like Foxtail Coffee, Kelly’s Homemade Ice Cream, and Donut King, with quick access to Downtown Winter Park and major highways. Don’t miss your chance to own this exceptional home in one of Winter Park’s most desirable communities!

2420 Firstlight Way, Winter Park
$398,000
3 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 05 SubDv. ⋅ 32792 Zip Code
Welcome to 3529 Australian Circle, a beautifully updated 3-bedroom, 2-bathroom POOL home located in the desirable EASTBROOK subdivision of WINTER PARK. Designed for comfort and everyday living, this home blends modern updates with timeless character. Step inside to find an open floor plan enhanced by high ceilings, WOOD-LOOK TILE flooring in the main living areas, and BAMBOO flooring in all three bedrooms. The REMODELED kitchen (2022) serves as the heart of the home, featuring BUTCHER BLOCK countertops, timeless cabinetry with soft-close drawers, a large breakfast bar, and a new mini-split system for improved air circulation. The kitchen flows seamlessly into the dining area and great room, creating a welcoming space for both entertaining and everyday moments. Adding warmth and character, the shiplap ceilings in the kitchen and great room tie the design together. The interior was freshly PAINTED in 2023, while crown molding (2024) adds a refined finishing touch. Step through the French doors into your private backyard oasis—complete with a covered porch featuring a tongue-and-groove ceiling, a fully FENCED yard, and a large open-air pool accented with flagstone. The 2023 irrigation system keeps the beautiful exotic palms thriving, and the system draws from a backyard aquifer, helping to save on water bills. The primary suite offers a peaceful retreat with an en-suite bathroom, granite countertop, and a walk-in shower with travertine tile. Two additional bedrooms share a stylish second bathroom. Practical updates provide peace of mind, including a roof (2018), A/C (2018), electrical panel (2021), water heater (2022), and double-paned windows. The SIDE-ENTRY one-car GARAGE adds convenience and curb appeal. Take advantage of an Exclusive Offer: 1% of loan amount toward closing costs or rate buy-down. Inquire today! Located on a quiet street with no HOA restrictions, this home is zoned for top-rated Seminole County schools and just minutes from Park Avenue’s shopping and dining, Rollins College, Winter Park Hospital, and nearby museums. With its thoughtful updates, inviting layout, and unbeatable location, this home offers an exceptional opportunity to enjoy the Winter Park lifestyle. Schedule your private tour today!

3529 Australian Circle, Winter Park
$445,000
3 Beds ⋅ 3 Baths ⋅ Enclave At Hawks Crest SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. This end unit townhouse is filled with natural light, thanks to its abundance of windows and soaring ceilings, creating a bright and open atmosphere. As you step inside this home, you'll be greeted by high ceilings and neutral colors which enhance the abundance of natural light. The expansive great room is perfect for entertaining, and the kitchen features sleek espresso cabinets, stunning granite countertops, and stainless-steel appliances. The great room also opens to a screened lanai, ideal for enjoying the Florida weather. There is also a half bath on the main level. As you make your way upstairs, you'll discover a thoughtfully designed split floor plan. There are two generously sized bedrooms and a nearby bath, while on the other side is a spacious primary suite and laundry room. Both elegant bathrooms are adorned with granite countertops. This home boasts a 2-car garage, a long paved driveway and ample guest parking nearby. This gated community of Hawk's Crest offers fantastic amenities, including a resort-style pool, playground, parks, and picnic areas, all with low monthly HOA fees(which include cable and internet). Perfectly situated just a 2-minute walk from the new Park Maitland Preschool and a 5-minute drive to Trinity Prep, one of Central Florida's premier private middle/high school. Also near the entrance of the community is Foxtail Coffee, Kelly’s Homemade Ice Cream, and The Ravenous Pig restaurant. You will find this community is centrally located, as you are just 10 minutes from the thriving downtown Winter Park and easy access to all major highways. Don't miss your chance to own this beautiful townhome—schedule your showing today!

2380 Shadowland Loop, Winter Park