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$370,000
3 Beds ⋅ 3 Baths ⋅ Hyde Park SubDv. ⋅ 32792 Zip Code
Beautiful SPLIT plan, 3 bedroom 2 bath for sale. The property has been well maintained and it is ready for its new owners. The family room has a fireplace and the Kitchen features a breakfast nook opening on a private back yard. The natural gas community features a fishing dock, sports courts, playground and walking paths and is within 5 minutes to shopping and restaurants, 20 minutes to Park Avenue and 30 minutes to Downtown Orlando. Extra bonus…..zoned for the fabulous Seminole County Schools. This central location has it all! The roof was replaced in 2020 and the AC was recently replaced ! School district and room dimensions to be independently verified.

1448 E Brookshire Court, Winter Park
$450,000
3 Beds ⋅ 3 Baths ⋅ Lake Waunatta Village SubDv. ⋅ 32792 Zip Code
Welcome home to this immaculately maintained 3-bedroom, 3-bathroom brick home in Winter Park, ideally located in one of Central Florida’s most sought-after areas and offering the freedom of no HOA. Thoughtfully cared for and upgraded, this home blends timeless construction with modern comfort and exceptional functionality, making it perfect for everyday living and entertaining. The heart of the home is the stunning kitchen, featuring quartz countertops, an oversized farmhouse sink, stainless steel appliances, stylish cabinetry, and updated lighting, creating a bright and inviting space for cooking and gathering. Wood-look flooring flows through the main living areas, leading to a warm and welcoming living room highlighted by a charming painted brick fireplace. The spacious layout offers comfortable bedrooms and well-appointed bathrooms, providing flexibility for families, guests, or work-from-home needs. A large laundry room with a utility tub sink adds everyday convenience and functionality. Step outside to your private backyard retreat with a screened patio and sparkling pool, ideal for enjoying Florida living year-round. A storage shed in the backyard provides convenient space for tools, lawn equipment, and outdoor gear. The oversized two-car garage is a rare and valuable feature and includes a full bathroom with shower, making it perfect for a workshop, hobby area, home gym, or pool access. The garage refrigerator, workbench, and shelving convey, creating a move-in-ready space for projects and storage. Additional peace of mind comes with a roof replaced in 2021, adding long-term value and helping reduce insurance concerns. Located close to parks, shopping, dining, and everything Winter Park is known for, this home offers the perfect blend of style, flexibility, and lifestyle. This is a rare opportunity to own an immaculately maintained brick 3/3 home in Winter Park with no HOA, modern updates, and features that truly set it apart.

7618 Waunatta Court, Winter Park
$430,000
4 Beds ⋅ 3 Baths ⋅ Country Lane SubDv. ⋅ 32792 Zip Code
Enjoy the convenience of living just minutes from top-rated schools, colleges, shopping, and major highways in this beautifully updated, light-filled home set within a well-established, family-friendly lakefront community. The home features 2018 roof, fencing, and plumbing. The interior paint, fully remodeled kitchen with appliances, half bath updates and tile flooring were completed in 2021. Exterior was painted 2025. Community has private access to Tennis court, lake front park and playground. Additional highlights include a top-of-the-line whole-home power generator, reverse osmosis water filtration system, security cameras, and a new thermostat. Vaulted ceilings and abundant natural light enhance the spacious living and dining areas. The kitchen offers space for a breakfast nook. Sliding doors lead to a screened-in patio accessible from both the kitchen and family room. A convenient half bath is located downstairs.

1543 Lawndale Circle, Winter Park
$424,900
3 Beds ⋅ 2 Baths ⋅ Casa Aloma SubDv. ⋅ 32792 Zip Code
Located in the highly desirable Casa Aloma neighborhood of Winter Park, this updated 3-bedroom, 2-bath, 2,083 sq ft home offers unique architectural appeal paired with thoughtful modern enhancements. Built in 1969, the home features concrete block construction on a concrete foundation, providing durability and peace of mind. Situated on a corner lot with updated landscaping, the property offers excellent curb appeal and outdoor functionality. Inside, the home has seen numerous recent updates, including new quartz kitchen countertops (2025), updated bathrooms, and updated walls and flooring throughout. The bonus room provides flexibility for use as an additional bedroom, home office, or secondary living area. Major system improvements include PEX plumbing, a newly installed 17 SEER AC system, a new water heater, electrical updates completed in 2008, and a metal roof installed in 2013 over 1x12 tongue-and-groove decking, offering exceptional strength and longevity. The home is protected by an active termite bond, with Sentricon installed in 2025. The backyard is highlighted by a 15’ x 30’ in-ground pool, a new vinyl fence (2023), and a five-zone in-ground sprinkler system with a programmable timer. The property is located in Flood Zone X (no flood insurance required) and has no HOA. Enjoy an excellent location known for top-rated schools, just minutes from AdventHealth, Full Sail University, FL-436, and an abundance of shopping and dining options. Do not miss the opportunity to purchase a well-maintained home with proven rental income and long-term investment potential.

1367 Tierra Circle, Winter Park
$440,000
5 Beds ⋅ 2 Baths ⋅ Howell Estates Rep SubDv. ⋅ 32792 Zip Code
A Fully Renovated Gem in the Heart of Winter Park Welcome to this stunningly renovated 5-bedroom, 2-bathroom residence, perfectly positioned in one of Winter Park’s most sought-after neighborhoods. Offering over 2,000 square feet of beautifully designed living space, this home seamlessly blends modern elegance, everyday comfort, and an unbeatable Central Florida location—all set on a quiet, picturesque, tree-lined street. Exceptional Upgrades & Features Include: New A/C units (2021) Fully re-piped plumbing New water heater Elegant porcelain tile and plush carpeting New baseboards throughout At the heart of the home is a show-stopping chef’s kitchen, thoughtfully redesigned with brand-new solid wood shaker cabinetry, sleek quartz countertops, a farmhouse-style sink, and stainless steel appliances—perfectly balancing style, durability, and functionality. The open-concept floor plan flows effortlessly into the expansive living and dining areas, creating an inviting space ideal for entertaining or everyday living. All five bedrooms offer exceptional versatility, easily accommodating family, guests, or a private home office. Both bathrooms have been completely remodeled with spa-inspired finishes, delivering a refined sense of luxury and relaxation. Step outside to a spacious backyard, perfect for pets, weekend gatherings, or outdoor entertaining, with ample room to add a pool or create your dream garden oasis. Unbeatable Location: Just minutes from Park Avenue, Full Sail University, the Cady Way Trail, and an impressive selection of dining, shopping, and cultural attractions, this home places you at the center of everything that makes Winter Park one of Central Florida’s most desirable communities. This move-in-ready home is a rare opportunity—offering modern upgrades, generous space, and a prime location.

1028 Princess Gate Boulevard, Winter Park
$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
$268,950
2 Beds ⋅ 2 Baths ⋅ Coronation Add SubDv. ⋅ 32792 Zip Code
BACK ON MARKET!! Buyer financing fell through! **Qualified buyers may be eligible for up to $40,000 in down payment assistance** Welcome home to this fully renovated 2-bedroom, 1.5-bath residence! This home features a brand-new kitchen, new flooring throughout, and beautifully updated bathrooms. Nestled in a quiet neighborhood, it offers a large backyard—perfect for outdoor entertaining or future expansion. Ideal for a first-time homebuyer or anyone seeking stress-free living. Best of all, NO HOA! Conveniently located near major highways, great schools, shopping, and dining in the highly desirable Winter Park area. Don’t wait—make this home yours today!

3220 Netherwood Drive, Winter Park
$350,000
3 Beds ⋅ 2 Baths ⋅ Casa Aloma SubDv. ⋅ 32792 Zip Code
Welcome to the beautiful Winter Park! Roof is 5-years-old. A/C is about 6-years-old. Water heater is about 6-years-old. Property does have some damage in the ceiling of the garage where some water leaked prior to having a new roof placed in 2021. PLEASE NOTE I AM NOT AVAILABLE ON THE SABBATH/SATURDAYS.

1438 Tierra Circle, Winter Park
$714,000
4 Beds ⋅ 3 Baths ⋅ Pelican Bay SubDv. ⋅ 32792 Zip Code
Fantastic, updated Winter Park abode with 4 bedrooms, 2.5 baths, beautiful soaring wood plank ceilings, sparkling salt-filtration pool, and almost 3,000 sq ft is available now. This executive home located in the upscale Pelican Bay neighborhood is sure to please with so many recent updates, an oversized lushly treed lot (.46 acre), a long paver driveway and front walk, and private community lakefront park with fishing dock, picnic tables, and 1/2 basketball court. Stepping inside, the spacious family room with 2 story brick fireplace and double glass sliders opening to the covered lanai is the heart of the home and one impressive space. A large formal dining room with built-in cabinets and wine rack is just off the kitchen, making entertaining a breeze. Lovely wood plank ceilings continue throughout the kitchen, breakfast bar, and dinette areas. High-grade, beautiful level 3 granite countertops adorn the solid wood cabinetry and breakfast bar while stainless steel appliances will be a hit with the home chef. Don’t miss the charming covered patio or the convenient laundry room and half guest bath leading to the oversized 2-car garage. Three spacious guest bedrooms with wood flooring (all with larger than average closets) and a full bath with double sink vanity and access to pool deck make up the rest of the first floor. Upstairs off the loft is the private den/office space and HUGE primary suite. Cathedral ceilings with tall windows, glass slider out to your private balcony, and expansive walk-in closet with custom built-in cabinets make this a true owner’s retreat. Total luxury bathroom remodel (2025) includes double vanities with quartz countertops, fog-free LED backlit mirrors, separate toilet room with Japanese style toilet with built in bidet, and a 2-person glass walk-in shower with wall jets and rain-shower heads, adding to the spa feeling. All the fun will be had in the tropical backyard with a 48’ long covered lanai and giant screen enclosed, heated pool (NEW electric pool heater 2024). And of course, the paver walkway outside the screen leads to another patio, perfect for sunbathing or relaxing around a firepit on a cool Florida evening. Home updates: NEW main HVAC 2025 - Total primary bath remodel 2025 - NEW pool heater, LED pool light, and pool pump 2024 - NEW exterior electrical panel/surge protector 2024 - NEW water softener system 2022 - NEW roof 2021 – New electrical panel 2020 and ask for a full list of even more upgrades and improvements.

1449 Pelican Bay Trail, Winter Park
$370,000
3 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 05 SubDv. ⋅ 32792 Zip Code
Virtually Staged. Back on the market and better than ever! New water heater and minor repairs addressed and ready for the new owner! Come see this newly renovated home in the Eastbrook neighborhood of Winter Park. Offering 3 bedrooms and 2 full baths it’s the perfect sanctuary for families and entertainers alike. You will enjoy the bright, airy feel of the open floor plan accentuated by the vaulted ceilings that flood the space with natural light. The stylish interior includes luxury vinyl plank flooring throughout, complemented by elegant tile in the bathrooms and laundry room. Relax in not one, but two generous living areas, perfect for family gatherings, entertaining or cozy nights in. Cook like a pro in your eat-in kitchen featuring brand new ENERGY STAR stainless steel appliances, ample cabinetry, and convenient carport access for effortless unloading. The generous backyard provides a private oasis for outdoor activities, barbecues, and gardening enthusiasts. Plus, the expansive driveway and two-car carport ensure plenty of parking for your guests. Recent upgrades include ceiling fans, blinds, fresh paint, stainless steel appliances, a newer roof (2017) and a well-maintained air conditioner (only 4 years old) ensuring peace of mind for years to come. Located in Seminole County, known for great schools and in a community with NO HOA fees, giving you the freedom to enjoy your space. Plus, you're just moments away from shopping, dining, and parks!

1617 Chilean Lane, Winter Park
$629,000
3 Beds ⋅ 2 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code
Welcome home to a place where hard work has been done and everyday living feels effortless. This beautifully renovated three-bedroom, two-bath home is move-in ready, offering peace of mind and thoughtful, classic updates throughout. It’s ideal for a family ready to settle in and start making memories from day one. Set directly along scenic Cady Way Trail, you’ll love having miles of paved paths right outside your door for biking, recreation and weekend adventures, all while staying connected to nearby parks, shops and Winter Park conveniences. The trail even connects to Brookshire Elementary School in under a five-minute walk. Inside, the home shines with fresh interior paint, smooth ceilings, updated lighting and fans, and durable NuCore waterproof LVP flooring throughout the main living and bedroom areas. Baths feature refreshed flooring, vanities and toilets, while the kitchen blends character and function with an added pantry for storage, restored terrazzo floors, new soft-close wood cabinetry, quartz countertops, gold hardware and an LG stainless steel appliance package. Classic touches elevate this kitchen to a whole new level and beckons for company. Outside, enjoy a freshly painted exterior, new vinyl fencing, a concrete patio ideal for play or entertaining, and updated garage door equipment and opener. A complete window package from New South windows brightens the space and gives a curb appeal that turns heads. Major systems are taken care of too, with a 2018 roof, 2024 electrical panels, a 2022 air-conditioning system, and recently cleaned air handler, compressor, and ductwork for added comfort and efficiency. This is the kind of home that lets you skip the projects and focus on what matters most like living, relaxing and enjoying your new neighborhood. Winter Park Pines is also home to an 18-hole public golf course and directly connects you to Baldwin Park via the trail.

513 Cornwall Road, Winter Park
$247,900
2 Beds ⋅ 2 Baths ⋅ Cedarwood Village 1 SubDv. ⋅ 32792 Zip Code
This 2 bedroom, 2 bathroom condo is located in Winter Park's Cedarwood Village near local shops, restaurants, and schools. Features include a spacious floor plan with custom upgrades throughout, a lovely kitchen with stainless steel appliances, waterfall countertops, and breakfast bar, an open living room with fireplace, dining room with wine bar, and gorgeous primary suite with a walk-in closet and walk-in shower. Additional features include soaring ceilings with skylights, a laundry room, and beautiful screened patio. Community amenities include a pool, tennis court, and club house.

2487 Tahoe Circle, Winter Park
$158,775
3 Beds ⋅ 2 Baths ⋅ Tanglewood Sec 3 Rep SubDv. ⋅ 32792 Zip Code
This home is located in desirable Winter Park. Has loads of potential. Great location. House is solid and needs some work, but this offering is priced right and ready to go. Sold As-Is.

1823 Maywood Road, Winter Park
$755,000
4 Beds ⋅ 2 Baths ⋅ Greenview At Winter Pines SubDv. ⋅ 32792 Zip Code
Fully updated 4 bed/2 bath Winter Park Pines home ready for a new owner! Tucked away at the end of a quiet cul-de-sac, this fully renovated home offers the perfect blend of modern luxury and serene surroundings. The brand new kitchen and bathrooms showcase quartz countertops, elegant gold fixtures, and custom details, complemented by new engineered wood flooring, interior laundry, and new windows and sliding doors that fill the space with natural light. Additional upgrades include new doors, trim, soffits, fresh interior and exterior paint, and a beautiful paver patio. Outside, enjoy all-new landscaping with fresh sod and a new irrigation system. Major improvements provide peace of mind, including a NEW ROOF (2025), garage door (2025), electric panel (2024), and a NEW HVAC system (2026). Sitting at the end of the cul-de-sac and backing up to the scenic Cady Way trail, ideal for biking, walking, and running, the property provides both privacy and an active lifestyle right outside your door. This home is zoned for highly rated Winter Park schools: Brookshire Elementary, Glenridge Middle, and Winter Park High School. There is an optional HOA in the Winter Park Pines community.

1317 Medinah Court, Winter Park
$387,000
3 Beds ⋅ 2 Baths ⋅ Country Lane SubDv. ⋅ 32792 Zip Code
Modern upgrades meet peaceful lakeside living with NO REAR NEIGHBOR. Freshly painted inside and out, this refreshed home is move in ready and checks all the boxes. The modern kitchen features granite countertops, stainless steel appliances, custom pull out shelving, and plenty of counter space for cooking, coffee bars, and hosting friends. A charming atrium adds natural light and a unique architectural edge you wont find everywhere. Outback the private patio opens to scenic park views with no rear neighbors giving you the privacy and space you have been looking for. Just a short walk to Lake Florence, you'll also love the exclusive lakefront park with fishing pier, playground and tennis courts making outdoor active and scenic living part of everyday life.

1655 Tremont Lane, Winter Park
$379,990
3 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 05 SubDv. ⋅ 32792 Zip Code
Stunning Newly Remodeled Move-In Ready Home! Property Highlights: • 3 Bedrooms | 2 Bathrooms – Both bathrooms fully modernized with contemporary fixtures, sleek tile work, and high-end finishes • Brand-New Flooring Throughout – Fresh, durable, and stylish flooring for a clean, modern look • Gourmet Kitchen with Quartz Countertops – Gorgeous new quartz surfaces, updated cabinetry, and stainless steel appliances • Newer Roof & Brand-New AC System – Key updates completed for efficiency, comfort, and worry-free living • Open-Concept Living – Bright, airy layout with excellent flow and plenty of natural light • Spacious Bedrooms – Three comfortable bedrooms with good closet space and natural light • Private Backyard – Low-maintenance outdoor area perfect for relaxing or entertaining • Ample Parking – Roomy driveway accommodates multiple vehicles • Prime Location – Close to great schools, parks, shopping, and convenient transit This beautifully remodeled home is 100% move-in ready with all the important upgrades already done! Enjoy fully modernized bathrooms, brand-new flooring throughout, stunning quartz countertops, a newer roof, and a brand-new AC system—everything you need for comfortable, contemporary living without lifting a finger. Priced to sell and ready for its new owner—schedule your private tour today! One or more pictures are virtually staged !

1378 Chilean Lane, 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
$714,000
3 Beds ⋅ 2 Baths ⋅ Kenilworth Shores SubDv. ⋅ 32792 Zip Code
C H A R M I N G INSIDE & OUT! Delightful curb appeal & quaint front porch welcome you HOME! Move right into this ONE STORY immaculate & charming home on a beautiful tree-lined street in Winter Park. You will be enthralled with the hardwood floors, crown molding, amazing floor plan & tons of natural light! Spacious living room with bay window leads to dining room with original built-ins & french pocket doors invite you into family room with cozy fireplace. Updated kitchen boasts white cabinets, stone counters, stainless steel appliance & a cozy breakfast nook with french doors leading to open patio & serene, fenced backyard. Lovely primary bedroom offers renovated ensuite bath. Extras include: Oversized 2 car garage, Brookshire Elementary, Glenridge Middle & Winter Park High, ROOF 2021. NEW PLUMBING 2023. NEW DUCTWORK 2023. NEW ELECTRIC PANEL 2023. NEW INSULATION 2023. PRIMARY BATH RENOVATED 2024. NEW GUTTERS & LEAF-GUARDS 2024. NEW LAWN & LANDSCAPE 2024. IRRIGATION AUTOMATION 2024. WELCOME HOME!

636 Dunblane Drive, 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
$724,900
4 Beds ⋅ 4 Baths ⋅ Landings At Hawks Crest SubDv. ⋅ 32792 Zip Code
Located within the gated community of Hawk’s Crest, one of Winter Park’s most desirable neighborhoods, this beautifully maintained two-story home is set on an oversized lot with tranquil pond views and a layout designed to live effortlessly. Light-filled, open, and thoughtfully upgraded, the home offers a balance of comfort, style, and everyday functionality. A pavered driveway and walkway create an inviting arrival, leading into a bright interior with soaring ceilings and abundant natural light. The main living space flows seamlessly, anchored by a chef’s kitchen featuring quartz countertops, stainless steel appliances, solid wood cabinetry, and a generous island with breakfast bar—perfect for casual meals, entertaining, or gathering at the end of the day. The kitchen opens naturally to the dining and family rooms, creating a connected space that feels both open and welcoming. Sliding doors lead to a covered lanai overlooking the pond, extending the living space outdoors and providing a peaceful backdrop for morning coffee or evening relaxation. Inside, upgraded luxury vinyl flooring and custom roller shades add warmth and a polished finish throughout the main living areas. The first-floor primary suite offers a private retreat with serene water views, a spacious walk-in closet, and a spa-inspired bath with dual vanities and a walk-in shower. A dedicated office on the main level adds flexibility and can easily function as a fifth bedroom if needed. Upstairs, a generous loft provides additional living space—ideal for a media room, play area, or secondary lounge—while three well-sized bedrooms offer comfort and versatility for guests, hobbies, or working from home. Energy-efficient features, ample storage, and thoughtful design make the home as practical as it is inviting. Residents of Hawk’s Crest enjoy resort-style amenities including a community pool, fitness center, clubhouse, playgrounds, and scenic walking paths, along with HOA-included lawn care for low-maintenance living. Ideally situated near shopping, dining, outdoor recreation, and major roadways, this home offers both convenience and a sense of retreat within Winter Park. Come experience the lifestyle and setting that make this home truly special—schedule your private showing today.

1340 Blue Stem Lane, 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
$330,000
3 Beds ⋅ 2 Baths ⋅ Country Lane SubDv. ⋅ 32792 Zip Code
PRICE REDUCED! PLUS SELLER OFFERS $7500 DECOR CREDIT TO BUYER! Make it your very own in 2026! Great opportunity to add your personal touches to this super 3 bed / 2 bath home in desirable Country Lane neighborhood. Vaulted ceiling bring tons of natural light into this great room style floorplan. Bonus room off dining area for office or crafts with door to fenced back yard - perfect for pets and play! Sunny kitchen at the heart of the home, with ample cabinet space. 3 good sized bedrooms, with great closets. Primary bedroom has access to private courtyard for morning coffee, exercise or meditations! Large 2 car garage with utility area. Mature landscape and rear gate to greenbelt area with short stroll to tennis and playground and lake access. Great schools and close to all Winter Park, Maitland has to offer!

1573 Lawndale Circle, Winter Park
$363,000
3 Beds ⋅ 2 Baths ⋅ Country Lane SubDv. ⋅ 32792 Zip Code
HIGHEST AND BEST DUE BY 12P ON 12/28. Prepare to fall in love with this comfy, cozy retreat tucked along a charming tree-lined street. From the inviting front elevation to the welcoming sitting porch and long driveway, this home instantly feels like “the one.” Inside, soaring vaulted ceilings and beautiful wood flooring create a warm, open atmosphere, while the eat-in kitchen shines with stainless appliances and extended counter space—perfect for baking, entertaining, or simply spreading out and enjoying your morning coffee. It’s a kitchen designed for gathering and making memories. The split-bedroom floor plan offers privacy for the primary suite, complete with its own bath and peaceful views of the private, fenced backyard. Step out to the spacious back patio—an ideal spot for early morning coffee or evening grilling. Enjoy peace of mind and energy efficiency with solar panels installed in 2023, helping keep utility costs low while adding modern value to this already wonderful home. Just a short stroll brings you to the community’s private lake access and tennis courts, adding a touch of lifestyle and recreation right outside your door. Conveniently located minutes from downtown Winter Park, major roadways, shopping, and dining, this home truly puts everything you need within easy reach. Charming, energy-efficient, and full of heart—this is a place where every day feels a little more enjoyable.

1436 Auburn Green Loop, 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
$390,000
3 Beds ⋅ 2 Baths ⋅ Country Lane SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. Welcome Home! Incredible opportunity to live in the desirable Country Lane community in Winter Park! This charming 3-bedroom, 2-bath POOL home features an extra-large backyard, ideal for entertaining, play, or future outdoor projects. Inside, you’ll love the beautiful engineered hardwood floors throughout—NO carpet! Major updates include New A/C (2022), Re-pipe (2022), and Roof (2015) for added peace of mind. The community of Country Lane offers outstanding amenities including a playground, tennis courts, multiple green spaces, and access to Lake Florence. Residents enjoy limited lake access perfect for kayaking, paddleboarding, canoeing, peaceful evening sunsets, and relaxing morning fishing. This home offers comfort, convenience, and an unmatched lifestyle—schedule your showing today!

1566 Lawndale Circle, 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
$560,000
4 Beds ⋅ 2 Baths ⋅ Brookshire Heights SubDv. ⋅ 32792 Zip Code
Welcome to 2350 Cady Way! Ideally located within walking distance to Brookshire Elementary and directly across from Showalter Field, this home offers easy access to the Cady Way Trail, Baldwin Park’s downtown area and dog park, Winter Park AdventHealth Hospital, and the Crosby Wellness Center, and is just a 5 to 10 minute drive to Park Avenue’s shopping, dining, and entertainment. Step inside to a bright and inviting living room with sliding doors to the backyard and a shared fireplace with the adjacent family room. The family room offers built-in shelving, cabinet storage, and sliding doors leading to a screened-in porch. The kitchen connects to a spacious laundry room with built-in cabinetry and floating shelves, with direct access to an oversized two-car garage featuring built-in shelving and storage cabinets. On the opposite side of the laundry room is a functional mudroom with an additional door to the backyard. The primary bedroom features a walk-in closet with excellent natural light. The primary bathroom includes a walk-in shower, granite countertops, and built-in storage. The secondary bathroom also offers granite countertops, built-in storage, and a bathtub. Throughout the home you will find abundant storage, exceptional natural light, and new remote-controlled ceiling fans. Major updates include a new HVAC system, full plumbing re-pipe, updated electrical panel, exterior flood lighting, new flooring, new fence, new dishwasher, and chimney repairs completed in 2021. Additional improvements include new garage doors and openers in 2024, and in 2025 a new refrigerator, new roof with a 10-year warranty, fresh interior paint, a landscape refresh, and brand new windows.

2350 Cady Way, Winter Park
$525,000
4 Beds ⋅ 2 Baths ⋅ Casa Aloma SubDv. ⋅ 32792 Zip Code
Welcome to 2665 Tierra Circle, a captivating Mediterranean-inspired residence nestled in the desirable Casa Aloma neighborhood of Winter Park. This thoughtfully maintained 4-bedroom, 2-bath home spans 1,885 square feet and has been lovingly cared for by a single owner for the past 23 years, evident in every detail throughout. Step inside to discover a flowing floor plan featuring distinct living, dining, and family rooms, all bathed in abundant natural light, particularly during the afternoon hours. The home's signature feature is its numerous French doors that seamlessly connect the interior spaces to enchanting garden islander styled courtyard areas, creating an indoor-outdoor living experience reminiscent of classic Mediterranean architecture. Elegant tile flooring flows throughout the home, complemented by crown molding that adds a refined touch to each room. The primary bedroom serves as a private retreat with its en suite bathroom featuring a walk-in shower, while three additional guest bedrooms share a well-appointed hall bath. Notably, the dividing wall between the third and fourth bedrooms has been removed to create a generous suite, offering flexibility to reinstate a fourth private bedroom with simple drywall installation if desired. The true showpiece of this property is the mature landscaping and garden spaces that surround the home, offering multiple courtyard areas perfect for entertaining or peaceful relaxation. The private pool provides a refreshing escape, while block walls throughout ensure complete privacy on the spacious 0.24-acre corner lot. Practical updates include a 2021 HVAC system and 2019 roof, natural gas utilities, and a large laundry and storage room. The two-car garage completes this exceptional offering, presenting a rare opportunity to own a meticulously maintained retreat in one of Winter Park's most sought-after neighborhoods.

2665 Tierra Circle, 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