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$860,000
4 Beds 2 Baths 32792 Zip Code
Rare opportunity to own an established daycare operating from two structures on the same parcel, offered together with the real estate. The business currently provides immediate income for a hands-on owner or family-run operation. One structure is currently utilized for daycare operations, while the second structure is a single-family home that offers excellent potential for future daycare expansion (subject to licensing and approvals)—a unique value-add opportunity for growing operators. The property is already configured for childcare use with existing operations in place, making this an ideal turn-key opportunity for families looking to step into business ownership or operators seeking to expand their footprint. Sale includes real estate. Business goodwill, licensing, and operations may be included or negotiated separately. Convenient location with strong demand for childcare services. Please do not disturb staff or business operations. Showings by appointment only.

1521 Heron Wood Place, Winter Park

$1,670,000
5 Beds 5 Baths Brookshire Heights SubDv. 32792 Zip Code
Welcome to this stunning modern custom smart home, a true statement of luxury and design offering 3,033 square feet of impeccably curated living space with 5 bedrooms and 4.5 bathrooms. From the moment you arrive, the pavered driveway, architectural lighting, and manicured landscaping set the tone for a home built for both elegance and ease. The heart of the home is bathed in natural light, thanks to oversized picture windows that frame every space beautifully. Wide-plank wood flooring, 7.5” baseboards, crown molding, and custom lighting elevate the open-concept design, while built-in cabinetry and floating shelves add warmth and sophistication. This home was designed to entertain effortlessly—indoors and out. The gourmet kitchen is nothing short of exceptional, featuring top-of-the-line Thermador appliances, a gas cooktop, built-in convection ovens,quartz countertops, and custom cabinetry to the ceiling with extra under-island storage. A fully equipped extra prep kitchen enhances functionality, while a wine refrigerator and elegant finishes make hosting unforgettable gatherings seamless and stylish. The luxurious primary suite is a private sanctuary, offering generous space and serene ambiance. The spa-inspired ensuite boasts dual sinks, a soaking tub, and refined finishes throughout. Two expansive walk-in custom closets provide exceptional storage and organization, completing a retreat designed for comfort, indulgence and a peaceful view of the pool. Four additional bedrooms—each thoughtfully designed—offer flexibility for family, guests, or home offices. Custom closets and beautifully appointed bathrooms ensure comfort and privacy for everyone. Step outside to your own private oasis. The smart saltwater pool features a sun shelf and advanced automation, perfect for relaxation or entertaining. A motorized screen encloses the lanai, creating a seamless indoor-outdoor living experience. The fully outfitted outdoor kitchen includes a grill, sink, and refrigerator, ideal for al fresco dining. Pavered patios, landscape lighting, and lush surroundings complete the resort-style feel. This home is equipped with EV chargers, electric shades, a second laundry room upstairs, a full security system with cameras, gutters, termite bond, and a smart pool system, blending cutting-edge technology with peace of mind. Perfectly situated near top-rated schools, popular restaurants, and the Winter Park Pines golf course, this home offers both convenience and lifestyle—an entertainer’s dream in an unbeatable location.

501 Darcey Drive, Winter Park

$214,990
2 Beds 2 Baths Goldenrod Villas Condominium Associates SubDv. 32792 Zip Code
Location, Location, Location! This highly sought-after two-bedroom, two-bath condo in Winter Park won’t last long! Ideally situated close to the University of Central Florida, it's a perfect investment opportunity for parents offering lower monthly payments compared to the high costs of on-campus housing. Upgrades made in 2020 include a new roof, air conditioning system, and enhanced attic insulation. Additionally, a mini-split AC unit has been added to the rear enclosed Florida room, ensuring comfort year-round. Imagine cozy winter nights by the corner fireplace in the inviting living area! The cathedral ceilings in the living room create an open and spacious atmosphere, complemented by the convenient open floor plan connecting the kitchen and living areas. The kitchen features Corian countertops and a breakfast bar, perfect for casual dining, alongside a separate area for enjoying meals.For added convenience, a full-size washer and dryer are tucked away in a closet off the kitchen, making laundry days a breeze while you relax in the living room. Unwind in the enclosed Florida room with a good book and a glass of wine, or step outside to your private fenced brick paver patio, perfect for your pets to roam freely. The patio also includes a storage shed, ideal for storing holiday decorations or recreational equipment. Both bedrooms come with spacious walk-in closets. The guest bedroom offers a convenient pocket sliding door to the bathroom, along with an additional door leading to the main hallway for guest access. With affordable condo dues, this property stands out as a budget-friendly option compared to other condos and townhouse communities in the area. Location highlights close to 417 toll roads and St Rd 436(Semoran) for easy access and only an hour's drive to the beaches, 40 minutes to major attractions, 30 minutes to Orlando International Airport, and only 20 minutes to downtown Orlando. The owner is very motivated hence the reason this condo is 15K-10K priced below market value with comparable Condos selling for 230K-240K. Don’t miss your chance to make this wonderful condo your new home or excellent investment!!

7744 Country Place Unit C4, Winter Park

$180,000
2 Beds 2 Baths Four Seasons Condo SubDv. 32792 Zip Code
Beautiful 2 bedroom / 2 bath first floor condo in Winter Park's Four Seasons community. Great floorplan with large living room, separate dining space, and updated kitchen with white cabinetry and granite countertops. New windows installed, new water heater 2023, new roof 2023, replumbed, AC 2015! Primary bedroom with walk in closet and en-suite bath with walk in shower. Enjoy a cozy screened porch with a laundry closet. HOA fee includes pest control, water, sewer and trash services. Four Seasons offers 3 swimming pools, tennis, shuffleboard and a clubhouse. This pet friendly community is located just minutes from Park Avenue, Sprouts, Whole Foods, Winter Park YMCA, Rollins College, Full Sail University, shopping and restaurants galore.

200 Saint Andrews Boulevard Unit 2302, Winter Park

$760,000
4 Beds 3 Baths Tanglewood Sec 3 Rep SubDv. 32792 Zip Code
Welcome to 5233 Lake Howell Road, a thoughtfully updated residence offering modern finishes, extensive upgrades, and a private backyard retreat designed for both everyday living and effortless entertaining. Inside, white porcelain tile flooring and recessed lighting create a bright, cohesive atmosphere throughout the main living spaces. Expansive rear-facing windows frame serene views of the beautifully landscaped backyard. The fully renovated kitchen is both stylish and functional, featuring new cabinetry, under-cabinet lighting, a built-in oven, cooktop, microwave drawer, and new sink. The open-concept layout flows seamlessly into the Florida room, where abundant natural light enhances the inviting ambiance. The living area is anchored by a resurfaced wood-burning fireplace, adding warmth and timeless character. The primary suite serves as a peaceful retreat, complete with a renovated bathroom, custom closet system, and a conveniently located in-suite laundry area with custom frosted glass doors and a new stackable washer and dryer. Two additional guest bathrooms have also been renovated, and custom closet systems extend throughout the home, including guest bedrooms and hallway storage. The backyard is a true oasis, highlighted by a newly resurfaced 16x32 pool and multiple spaces for al fresco dining, lounging, or gathering around the fire pit. The new paver patio offers the perfect spot to unwind with a good book. The fully fenced yard features refreshed landscaping with artificial turf, landscape lighting, and a new irrigation system serving both the front and rear yards. A custom greenhouse/workshop with a misting system adds a unique and functional outdoor element, while thoughtful drainage enhancements, including a French drain along the rear of the home and patio drainage to the front sidewalk, provide added peace of mind. Major improvements include a new roof (2023), water heater (2023), HVAC system and ductwork (2023), and a full plumbing update (2023). Additional features include a mini-split system, drip irrigation, updated electrical and LED lighting throughout, Pella double-paned windows, remote shades throughout, Leafguard gutters, expanded circular driveway, and added attic insulation. The home is also equipped with Google cameras and a doorbell at both front and rear entrances, as well as pre-wiring for a pool heater. This move-in-ready home seamlessly blends modern comfort with thoughtful upgrades, all set in a desirable Winter Park location just minutes from the YMCA, Interlachen Country Club, Phelps Park, Park Avenue, and a variety of dining destinations.

5233 Lake Howell Road, Winter Park

$1,400,000
5 Beds 5 Baths Waters Edge At Hawks Crest SubDv. 32792 Zip Code
Set within the exclusive Winter Park community of Waters Edge at Hawks Crest, this stunning Kerrville II Meritage model offers refined luxury living on a premium lot boasting serene pond views. Thoughtfully designed for both elegant entertaining and everyday comfort, the open-concept layout is filled with natural light and showcases high-end finishes and upgrades throughout this 5 bedroom 4 ½ bath home. The gourmet kitchen services as the heart of the home, featuring premium cabinetry, quartz countertops, a spacious center island, and top-tier appliances, all flowing seamlessly into expansive living and dining areas. Enjoy peaceful mornings with picturesque pond views, sitting leisurely at the breakfast nook as you watch the sunrise or step onto your extended lanai to enjoy a dip in your sparkling saltwater, heated, self- cleaning pool, and spa. The main floor showcases a formal living room and dining room, private guest suite bedroom with its own bath leading to the pool area, perfect for multi-generational living or guests. The owner's suite is a private retreat overlooking the pool and water, complete with a spa-inspired bathroom, upscale finishes, and generous walk-in closets. Additional bedrooms and versatile living spaces provide flexibility for a media room, home office, fitness room or additional guest accommodations. The 3 car garage has overhead storage shelves, and an electric charging station. Hawks Crest is a resort-style community offering a fitness center, playground, clubhouse, pool, and private dock on Lake Howell perfect for kayaking, canoeing, paddle boarding, fishing or just relaxing. This prime location is ideally situated just minutes from Park Avenue's renowned shopping, dining and cultural attractions. Schedule your private showing today and experiencer the lifestyle of luxury Florida living.

1144 Wading Waters Circle, Winter Park

$475,000
3 Beds 2 Baths Georgetown Estates SubDv. 32792 Zip Code
3 bedrooms PLUS an office (or 4th bedroom) AND a "flex space". Easy access to all of Winter Park, UCF, and south Seminole County from this convenient, central location! If you've been searching for a spacious pool home with plenty of space for playing, entertaining, or even working from home -- you've found it here! When you walk in, you'll appreciate the intuitive flow of living space into the kitchen, with built-in eating space. Off of the kitchen, you'll find a bonus space (perfect for an office or home gym) as well as a large indoor laundry room/mudroom, and the converted garage which is ideal for a playroom or secondary living space. On the other side of the home, 2 secondary bedrooms, an oversized hall bathroom, and a primary with en suite bath. There are additional touches that go a long way, too, including the custom plantation shutters throughout the home and updated countertops in the kitchen. Much of your time will be spent in the backyard, enjoying a fenced in pool, screened porch, new custom shed (2025), and fully fenced yard with turf play area. Systems in the home have been well maintained: roof (2017), HVAC (2017), tankless gas water heater (2018), and brand new electrical updates (2026). The home was also re-plumbed in 2008.

3207 Lowndes Drive, Winter Park

$400,000
3 Beds 2 Baths Garden Grove SubDv. 32792 Zip Code
Discover a delightful pool home nestled in the heart of vibrant Winter Park, where you can enjoy the freedom of no HOA. Sunlight pours into every room, creating a warm and inviting atmosphere ideal for first-time buyers or families seeking a lovingly maintained, move-in-ready retreat. The kitchen features sleek granite countertops, abundant cabinetry, and all appliances, seamlessly flowing into the dining area for effortless entertaining and everyday living. Durable tile floors add style and practicality throughout the main spaces. Step onto the enclosed porch, a cozy spot overlooking a spacious backyard with a sparkling pool and privacy fence, perfect for unwinding or hosting memorable gatherings. Enjoy peace of mind with no HOA and several thoughtful updates: including a new roof was replaced in 2015, a heating and cooling system was replaced in 2019, enhanced attic & updated air conditioning ducts in 2020, garage door was replaced & vinyl floors installed in all three bedrooms in 2022, and parts of the hot water heater were replaced in 2025. The home also has a fully paid-off solar system, which helps lower electric bills and saves you money. Conveniently close to Winter Park’s best shopping, dining, medical offices, UCF, and major roads, making it easy to enjoy everything in the area. Whether you’re celebrating by the pool or enjoying a quiet morning on the porch, this move-in-ready house is ready for your special moments. Come see where your next chapter can start.

5547 Garden Grove Circle, Winter Park

$660,000
5 Beds 4 Baths Sanctuary At Aloma SubDv. 32792 Zip Code
NEW ROOF AND SOLAR PAID OFF AT CLOSING!!! Located in desirable Winter Park, this POOL home offers exceptional value. This spacious 5-bedroom plus den area, 3.5-bathroom house has a beautiful pond view from the front door. 3 car garage space and 6 car driveway give you plenty of space for storage and parking. 3,111 square feet of comfortable living space plus a gorgeous screened-in pool with spa. The home features high ceilings that create an open, airy feel throughout. The kitchen showcases elegant granite counters and modern stainless steel appliances. Hard flooring flows through the main living areas, offering both style and easy maintenance. Solar panels on the home save you hundreds each month on electricity. SELLER WILL PAY OFF SOLAR PANELS AT CLOSING! Step outside to your private backyard oasis with a screened-in pool and jacuzzi spa, ideal for year-round Florida living. The fully vinyl fenced yard provides privacy and security for families and pets. This move-in ready property means you can start enjoying your new home immediately. The location offers incredible convenience with easy access to Winter Park shopping, restaurants, and world-famous theme parks. Major roads are nearby, making commuting simple whether you work locally or need to travel throughout Central Florida. The gated community adds security and peace of mind. Winter Park is known for its charming downtown area, excellent schools, and beautiful parks. This neighborhood combines suburban tranquility with urban accessibility, giving you the best of both worlds. Schedule your showing today!

5275 Pine Lily Circle, Winter Park

$255,000
2 Beds 2 Baths Cedarwood Village 1 SubDv. 32792 Zip Code
Recently Improved to $259,900 - One of the BEST Values in Winter Park !! Welcome home to this spacious two-story Winter Park condo located in the sought-after Cedarwood Village community. Tucked away among mature landscaping yet close to everything, this residence offers a comfortable blend of privacy, architectural character, and convenience in a prime Central Florida location. The main living area features soaring 16.5-foot vaulted ceilings, a wood-burning fireplace, and sliding glass doors that lead to a screened rear porch, creating a seamless indoor-outdoor connection. Two skylights and a second-story loft overlooking the living room add architectural interest and flexible space ideal for a home office, reading nook, or guest retreat. The thoughtfully designed split floor plan enhances functionality and privacy. Additional highlights include a spacious kitchen with breakfast bar and island, a primary suite on the main level, and a screened back porch perfect for relaxing or entertaining. Community amenities include a swimming pool and tennis courts, supporting a low-maintenance, active lifestyle. Located just minutes from Rollins College, with convenient access to local retail shopping, dining, and everyday conveniences, this home is also a short drive to downtown Orlando, offering easy access to museums, theaters, and a variety of local events—combining the charm of Winter Park with excellent city connectivity. All measurements and information should be verified.

2501 Tahoe Circle, Winter Park

$1,200,000
6 Beds 4 Baths Lakeside Estates SubDv. 32792 Zip Code
Elevate your lifestyle in the prestigious Lakeside Estates, a private gated Winter Park community anchored by Garden Lake. In a quiet cul-de-sac, on a wrapping corner lot on over 1/3 of an acre and only a short distance to the playground making it easy. A six-bedroom, four-bath home sprawls over 4,200 square feet with back of the house opening to a covered porch with a generously sized saltwater pool, framed in by a podocarpus hedge for privacy, creating a backdrop for entertaining. An additional green space behind hedge for plenty of room to grow. This home has all functions you need with a formal dining and living spaces alongside a spacious family room that is open to kitchen and overlooks backyard. The island takes center stage with a waterfall edge feature and bar seating, custom 42-inch cabinetry, stainless appliances, a cozy eat-in kitchen nook with loads of workspace and closet pantry for ease of storage. A fantastic first-floor guest suite or flex space makes working from home easy. Go upstairs to where all the fun happens. A super large bonus room has additional home theatre rooms accessed through stylish barn doors and it is all snuggled in, everyone will want to stay. Primary suite enjoys a large walk-in closet and a spa bath retreat with soaking tub, walk-in shower and dual vanities. Other features of the home include wood floors throughout, custom window treatments, custom pool with paver decking and a summer kitchen with an abundance of privacy, professionally landscaped, three-car tandem garage with brick drive, long-lasting barrel tile roof, designer light fixtures and more. Lakeside Estates offers exclusive access to a community pier, playground and a boat dock for non-motor kayaks, fishing, canoes, paddleboards and more. In the highly rated Seminole County School district as well as minutes from Trinity Prep, Geneva School, Christian Circle and more. Enjoy world-class restaurants, shopping and beautiful parks and trails, close to major roadways, UCF, Valencia and downtown Orlando. A pristine location, coupled with a unique Winter Park community, is a rare find. Homes do not come along in this neighborhood often, making it a special opportunity for the discerning buyer.

3711 Vinsetta 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

$255,000
2 Beds 2 Baths Windward Square Sec 2 SubDv. 32792 Zip Code
Virtually Staged. ALL PLAY and NO WORK! Imagine coming home to a space where weekends are made for relaxing, entertaining, and enjoying the best of Florida living. This single-story, two-bedroom, two-bath townhome offers an effortless lifestyle in a location that puts everything within reach. Vaulted ceilings create an open, airy feel in the spacious living and dining area, while sliding glass doors lead to a private, fenced backyard with a large concrete patio?perfect for morning coffee, weekend barbecues, or unwinding after a long day. With no rear neighbors and views of the community green space, you?ll enjoy added privacy and tranquility. The kitchen is designed for everyday ease, featuring ample cabinetry, a breakfast bar, and all appliances included, making move-in simple. Retreat to the oversized primary suite with a walk-in closet and direct patio access, creating a true indoor-outdoor flow. The second bedroom offers flexibility for guests, a home office, or creative space. Step outside your front door and enjoy resort-style amenities, including three swimming pools, tennis courts, a clubhouse, and a playground—all with low HOA fees. With parking for three vehicles, convenience is built right in. Located close to shopping, dining, major roadways, and just minutes from Winter Park’s Park Avenue, this home delivers both comfort and connection. Owner-occupant only community—ideal for those looking to put down roots and enjoy a true neighborhood feel. Live more. Maintain less. Welcome home.

2651 Cayman Way, 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

$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

$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

$182,900
2 Beds 2 Baths Stratford A Winter Park Condo SubDv. 32792 Zip Code
Move-in ready! Exceptional value in the heart of Winter Park! Welcome to this beautifully maintained 2-bedroom, 2-bath ground-floor condominium, where comfort, convenience, and an unbeatable location come together. The thoughtfully designed floor plan features an open-concept living and dining area, a screened patio overlooking peaceful landscaped gardens, and recent upgrades and maintenance, including a new electrical panel (2024), washer & dryer (2024), dishwasher (2023), refrigerator (2020), and a complete A/C system service (2025). Enjoy resort-style amenities at Stratford at Winter Park, including two swimming pools, two lighted tennis courts, a fitness center, clubhouse, and car care facilities, all within a beautifully maintained community. Perfectly located just minutes from Park Avenue, Baldwin Park, Full Sail University, Rollins College, AdventHealth Winter Park, shopping, dining, cafés, golf courses, and major highways, this home offers the ideal balance of everyday convenience and the sought-after Winter Park lifestyle. Competitively priced and offering exceptional value in today's market, this move-in-ready home is an excellent choice for a primary residence, seasonal getaway, or long-term investment. Motivated seller. Schedule your showing today. Note: Some photos have been virtually staged for illustrative purposes.

205 Lewfield Circle Unit 205, Winter Park

$182,000
2 Beds 2 Baths Stratford A Winter Park Condo SubDv. 32792 Zip Code
This charming and well-maintained 2 bedroom, second-floor condo in Winter Park is ready for you to call your own! The home features comfortable carpeted living areas throughout. The centrally located galley kitchen offers plenty of cabinet and counter space and connects directly to the dining room. The spacious living room gets plenty of natural light through large sliding glass doors, opening to a covered and screened rear porch with a pool view. The primary suite features a walk-in closet and a private bath with a floor-to-ceiling tiled walk-in shower. The HOA completed roofing and plumbing improvements in 2019, and all exterior and grounds maintenance is handled by the on-site HOA. The Stratford community offers two pools, a community and fitness center, and tennis courts. Just minutes from popular Downtown Winter Park with its dining and shopping, with easy highway access via the 417 and I-4, and surrounded by nearby lakes and parks, this is one opportunity you don’t want to miss. Call today to schedule your private tour!

256 Lewfield Circle Unit 256, Winter Park

$175,000
2 Beds 2 Baths Four Seasons Condo SubDv. 32792 Zip Code
Welcome to this charming Seasons unit townhome offers a comfortable living experience in one of Winter Park’s most convenient locations. Thoughtfully updated and well cared for, the home combines practicality with beautiful touches. Inside, you’ll find laminate flooring throughout the main living areas, granite kitchen countertops, and a fresh, neutral interior palette. The functional floor plan is enhanced by excellent natural light. Providing flexibility for daily living and entertaining. Four Seasons residents enjoy access to multiple swimming pools, tennis courts, a fitness center, clubhouse, and beautifully maintained grounds that create a peaceful, park-like setting. With close proximity to Full Sail University, shopping centers, restaurants, and major highways, this property offers both convenience and long-term value an ideal option for a primary residence or a smart investment opportunity in.

200 Saint Andrew Unit 3103, Winter Park

$249,000
2 Beds 2 Baths Windward Square Sec 1 SubDv. 32792 Zip Code
*ACCEPTING BACKUP OFFERS* Welcome to 2432 Barbados Dr, Winter Park! This beautifully updated 2-bedroom, 2-bath home that delivers the perfect blend of comfort, privacy, and that easy Florida lifestyle. From the moment you arrive, you’ll appreciate the peace of mind that comes with a BRAND NEW roof, along with a layout that feels both functional and inviting. Inside, the home offers a bright, open living space that flows effortlessly for everyday living or entertaining friends and family. The split-bedroom setup provides privacy for everyone, with two full bathrooms that make hosting guests (or working from home) simple and comfortable. Step outside and you’ll find the real showstopper! A stunning, private backyard; your very own quiet retreat for morning coffee, weekend cookouts, gardening, or letting pets play. It’s the kind of outdoor space that’s hard to find and easy to fall in love with. Windward Square offers a recently removed pool, playground, sidewalks, security gate, and stunning landscape; all for an HOA less than $100 a month! Conveniently located near SR-436 and Howell Branch Rd, you’re close to shopping, dining, and everything that makes Winter Park such a sought-after place to call home! Whether you’re a first-time buyer, downsizing, or looking for a smart investment in a prime location, this one checks the boxes. Schedule your private showing today!

2432 Barbados Drive, 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

$90,500
1 Beds 1 Baths Colonies SubDv. 32792 Zip Code
GREAT INVESTMENT OPPORTUNITY! Seller is motivated! Completely remodeled and move-in ready, this beautiful 1-bedroom, 1-bathroom condo in Winter Park offers the perfect blend of comfort, convenience, and value. Located just 11 minutes from Orlando International Airport and close to UCF, Full Sail University, shopping malls, restaurants, major highways, and popular theme parks, this home is ideal for both homeowners and investors. The condo features brand new kitchen countertops and cabinets, giving it a fresh, modern look throughout. Whether you're searching for an affordable place to call home or a great addition to your rental portfolio, this unit is a fantastic option. Enjoy easy access to the community pool just a short walk away, and take advantage of the prime location within short distance to Target, local dining spots, and even a Twistee Treat. With so much to offer and tons of potential, this gem won’t last long, schedule your showing today!

3060 George Mason Avenue Unit 10C, 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