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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.

PENDING SALE; ACCEPTING BACK UP OFFERS. Tucked into one of Orlando’s most beloved neighborhoods, this home offers space, flexibility, and freedom with no HOA. Situated on a corner lot, you'll fall in love with the spacious, well-maintained backyard, a screened porch for outdoor living, and an oversized storage shed—perfect for gardening, hobbies, or extra storage. Inside, timeless original terrazzo and hardwood floors add warmth and character, beautifully complemented by a tastefully updated kitchen and an adjacent interior laundry room with built-in storage solutions and a deep freezer (and it's climate controlled!). The flexible floor plan includes two primary suites with en suite bathrooms, ideal for guests or an in-law suite, plus a third bedroom AND versatile flex space perfect for an office, nursery, or home gym. One of the primary bedrooms also has built-in flex space and a built-in kitchenette (morning room); it has endless potential due to its size. Major updates provide peace of mind, including a 2018 roof, 2025 HVAC, and newer windows. Zoned for highly rated Pershing K–8 and Boone High School, the location is hard to beat—minutes from downtown Orlando shopping and dining, just 15 minutes to Orlando International Airport, and around the corner from a community public boat ramp for weekend adventures.

Built in 2019, this stunning 4-bedroom, 3.5-bathroom residence combines timeless craftsmanship with modern sophistication in one of Winter Garden’s most desirable locations. Offering over 3,100 square feet of thoughtfully designed living space, this home pairs elegant interior finishes with extensive upgrades that make everyday living both effortless and refined. Step inside to find custom interior shutters, crown molding, and enhanced trimwork throughout, setting a tone of understated luxury. The chef’s kitchen impresses with double ovens, a gas cooktop, and a spacious layout that seamlessly connects to the open family room—complete with a custom-built entertainment center and cabinetry. Upstairs, the loft features a custom wet bar with built-in cabinetry, lighting, and sink—an ideal space for entertaining or relaxing at the end of the day. Retreat to the primary suite, where automatic blinds, a custom closet system, and a serene ensuite bath create a true sanctuary. Each bedroom includes customized storage, reflecting thoughtful attention to detail throughout the home. Outdoor living is equally remarkable: a fully equipped outdoor kitchen with kegerator, natural gas fire pit, outdoor shower, and motorized screens make this space perfect for year-round enjoyment. The custom second-floor porch adds an elevated retreat overlooking the property. Practical features abound, including a whole-home generator (serviced annually), saltwater and carbon filtration system, gas tankless water heater, new dishwasher and disposal, and metal shelving in the garage for optimized storage. Even exterior details—like added outlets for holiday lighting—reflect the home’s careful design. This property has been meticulously maintained, with biannual HVAC servicing, monthly pest control, a subterranean termite bond, annual generator and backflow servicing, and more—all ensuring peace of mind and long-term value. The neighborhood offers a beautiful community pool, just a short walk from the property. It is golf-cart friendly, too! Located just steps from the West Orange Trail, this home offers convenient access to historic Downtown Winter Garden, local shops, dining, and top-rated schools including Dillard Street Elementary, Lakeview Middle, and West Orange High.

Welcome to this inviting and well-maintained 5-bedroom home, perfectly situated on a generous corner lot of over one-third of an acre. With a desirable split floor plan, two separate living areas, and original terrazzo floors, this home offers a wonderful blend of mid-century charm and thoughtful updates for today’s lifestyle. Whether you work from home, aspire to have a playroom, or love an in-home gym, you'll have space for whatever your unique needs might be! At the heart of the home is a sophisticated kitchen, beautifully updated in 2003 with custom wood cabinetry and quartz countertops, offering both function and style. The primary bathroom, remodeled in 2010, continues the theme of tasteful upgrades throughout. The roof was replaced in 2023 and the HVAC was replaced in 2017. The electrical panels and the plumbing have also been updated. Step outside to your private backyard retreat featuring a large, sparkling pool enclosed by a 2013 screened lanai, perfect for relaxing or entertaining year-round. The expansive yard provides plenty of space for a garden, playset, or future addition—the possibilities are endless. This home has been lovingly cared for, with major updates including windows repaired or replaced in 2002 and 2024, new attic ductwork in 2020, and a driveway replaced in 2009. A two-car garage completes the picture, offering ample storage and convenience. With its spacious layout, timeless finishes, and generous lot, this home is a rare find that perfectly balances comfort, character, and potential. It is zoned for highly rated Orange County Public Schools and is conveniently located to the best of Winter Park including the Cady Way Trail, the Winter Park Pines Golf Club, and Lake Baldwin Park.

Here is the combination of charm and location you have been looking for in a home! This 3 bedroom, 2 bath, pool home is located in the highly sought-after Audubon Park Garden District, zoned for Audubon K-8 and Winter Park High School. Surrounded by mature oak trees, you'll love living just steps away from Leu Gardens! Enter the home into the gorgeous living room, noticing the light hardwood floors, plantation shutters, crown molding, and lighted built-in shelving with cabinets. Adjacent to the living room and just off of the kitchen, space to enjoy your meals in the cozy dining room, overlooking the backyard and pool. Off of both the living/dining area, to one side, is a large bonus room, which has enchanting, vaulted ceilings, a built-in desk with cabinets, a wall of windows to let that Florida sunshine in, as well as additional storage. You will also be able to access both the pool and the garage from this room. The kitchen overlooks the sparkling pool and large fenced in backyard, where you're sure to enjoy playing, swimming, grilling, and entertaining. The kitchen has newly painted cabinets and fixtures, beautiful granite counter tops, and all new stainless-steel appliances. Down the hall you will find the primary bedroom with an en suite bathroom, two closets, and access to the pool through another French door. All bedrooms have beautiful hardwood floors, plantation shutters, and ceiling fans. The roof is only 3 years old, and HVAC is 5 years old. The location of this house can’t be beat with just less than 2 miles to Publix, Baldwin Park, The Milk District, dining, and local shopping! Less than 4 miles is downtown Orlando! Also close by is Rollins College, Park Avenue, and the quaint cities of Winter Park and Maitland! And if you’re traveling for work or pleasure, the Orlando International Airport is only 30 minutes away! Come see this adorable home today!

You know it's going to be a winner when the primary walk-in-closet, alone, is 8'x10'! This beautiful Orwin Manor home has it all: 3 bedrooms, 2 bathrooms, and indoor laundry room, updated kitchen and baths, a detached 1 car garage, flex space for a playroom or office, and incredible systems updates like a 2018 roof, 2020 water heater, and 2022 HVAC. Once you get past the beautiful curb appeal, you'll step into a multifunctional living space with options for living and dining. You'll appreciate the split plan layout with two secondary bedrooms in one hallway and an expansive primary suite in the back of the home. All of the bedrooms have freshly cleaned carpet and the living spaces in the home are a versatile engineered hardwood. The kitchen, complete with dry bar and wine storage, is in the middle of the home making for easy entertaining and it's filled with convenient storage! Out back, enjoy the well-maintained yard space and 1 car garage for parking and/or storage. The location is ideal, as it's centrally located to the best of both Winter Park and Orlando. Less than a mile from Foxtail Coffee and Kelly's Ice Cream on Orange Ave, 1.5 miles from Rollins College, less than 2 miles from Publix, and so much more.

Welcome home to this beautifully maintained property on more than a third of an acre in one of Winter Park's favorite neighborhoods -- affectionately known as the Tree Streets! 1711 Chestnut Ave blends classic Florida design with intentional, modern systems. In both the front and back of the home, you'll appreciate the attention to detail in the landscape design, which will be in full bloom each Spring. The irrigation system for the lawn is on it's own well system. Enter the home to enjoy two separate living spaces, a split plan that offers a spacious primary suite and three secondary bedrooms, and three full bathrooms. The kitchen has been renovated to include custom cabinetry, granite countertops, and stainless steel appliances. It is open to the Family Room with an incredible view of the oversized backyard and pool. The mature landscaping out back offers privacy to enjoy this retreat, complete with ample space for outdoor living and entertaining! Some notable upgrades to this property include brand new HVAC systems (2) in 2021 and 2022, water heater in 2019, hurricane-rated windows between 2015-2017, home security in 2015, engineered hardwood flooring in 2015, custom wood shutters in 2017, new pool pump in 2016, and a re-plumb in 2005. Zoned for highly rated Orange County Public Schools (Lakemont, Maitland, and Winter Park), you're also central to some of the best shopping and dining in Winter Park: 2 miles from Park Avenue, 0.4 miles from the Winter Park YMCA, 0.3 miles from Phelps Park (playground, pickleball, tennis), 1.5 miles from the nearest Publix, 1.1 miles from Interlachen Country Club, and 14 miles from Orlando International Airport.

Welcome home to this beautifully updated and maintained College Park bungalow! Step inside and enjoy this historic restoration from start to finish. The living room, dining room, and kitchen flow perfectly for entertaining and efficient living and the 2 bedrooms share a large jack-and-jill bathroom with a double vanity and shower. The kitchen displays custom cabinetry and stunning quartz countertops along with newer appliances (all installed in 2021). The windows were professionally restored with the original trim for historical accuracy and aesthetic. In the back of the home, you'll love the Florida Room, which would make a perfect home office, gym, or secondary living space. Outside in the backyard, there is incredible, private space for gathering, outdoor living, and/or your pets. The yard is fully fenced, including the driveway, which has its own gate access to the detached 2-car garage. There are additional updates throughout, including new electrical and panel (2021), roof (2020), plumbing and electric water heater (2021), wood fence and gate (2021), garage doors (2022), irrigation (2022), crawlspace and attic professionally secured (2023). The HVAC system is approx. 8 years old and has been maintained annually. Fiber internet is available on the street.

Just in time for summer! Here's the trifecta of size, location, and condition that you've been waiting for! This beautiful 5 bedroom, 2 bath, 2 fireplaces, corner lot with a pool home is ready for your family! Come make memories for years to come as this home is large enough to grow in. Beautiful hardwood floors through out main living areas, large tiled Florida room with fireplace overlooking the pool on nearly a third of an acre. A lovely kitchen, suitable for entertaining, with a formal dining and living room on either side with a second fireplace in the living room. Your family will also love having an inside laundry room right off of the 2 car garage. Need lots of storage? No problem! This home has plenty with 3 hall closets, additional closet in the second bathroom, and all of bedrooms have walk in closets! If you need some exercise or want to meet your neighbors, right across the street, is the Winter Park Golf Club where you can walk nine holes or mingle at the new Bonfire restaurant! This house is also zoned for top rated schools, Brookshire Elementary, Glenridge Middle School, and Winter Park High School. All bedrooms have new carpet. Interior and exterior of home has been repainted. Four point system dates are as follows, Roof: 2022, HVAC:2023/2024, Plumbing: 2006, Electrical: 2006, Water heater: Tankless, 2023. All this house needs is you! Come see this beauty today!

This incredible home has only ever had one owner! It's your opportunity to own .34 acres on a Winter Park cul-de-sac, complete with mature landscaping and backyard access to the Cady Way Trail. The oversized backyard has endless potential -- bring your ideas for a pool, an addition, or an amazing garden. Inside the home, you'll find a 4 bedroom, 2 bath split floor plan with multiple living space options, including a fully enclosed back porch. If you're looking for great storage space, this home offers 9 closets, including a walk-in closet in each of the bedrooms. Each of the two bathrooms includes a double vanity and tub/shower combo. It also has a full 2 car garage and an indoor laundry room with a large utility sink! The roof was replaced in 2017, the water heater is from 2015, and one of the two electrical panels was replaced in 2024. 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 that puts on neighborhood programming for members.

Here's your chance to live in the heart of College Park, walkable to highly rated Princeton Elementary! This home is move-in ready, no matter whether you need space for an in-home office, a playroom, a home gym, or a backyard retreat. You'll notice the versatile bamboo floors from your first step inside and then realize how effortless entertaining can be in this open-concept first floor. This living space flows beautifully into the back patio, where mature landscaping and pavers make it feel like a low-maintenance retreat. Built in pantry/storage space off of the eat-in kitchen is the perfect place to center your home organization, work on homework, or stash your Costco haul. There is a first floor primary bedroom with a large closet, but the door has been removed so that the current owners can enjoy this space as a playroom. Upstairs, there are three more bedrooms including a spacious primary suite. The current owners love that the laundry is conveniently located in the primary closet so there is never a need to haul laundry up or down the stairs. The loft area has served as a secondary play space, a reading nook, and a home office so can be used for whatever flex space you might imagine! The roof is brand new (2024), the HVAC was replaced in 2016, and the water heater is from 2017.

Back on Market with NEW HVAC! Charming 2/2 located in desirable College Park neighborhood! This adorable 1940's home sits on nearly a quarter of an acre and is walking distance to coffee shops, restaurants, grocery stores and entertainment! Just minutes from I-4, you can be in Downtown Orlando, or at one of Central Florida’s many theme parks in no time. The updated kitchen boasts functional storage systems and a dining nook with built-in seating. The kitchen opens up to the formal living room for you to enjoy family time and entertain guests year-round. A bright and airy sunroom features floor-to-ceiling windows with built-in blinds and French doors out to your beautifully maintained back deck. Back inside, the oversized primary suite features ample storage, a flex space to be used as an office or nursery, an in-suite laundry room, and built-in library shelving. The attached ensuite boasts a beautiful claw-foot tub, spacious walk-in shower, brand-new vanity, even more storage, and direct access to the backyard. Another full bathroom is located directly across from the secondary bedroom, which is flooded with natural light and boasts a built-in closet system to maximize storage space. Off of the sunroom, there is an attached single-car garage with a workshop bench. Schedule a showing for this adorable move-in ready home today and make it yours!

NOW ACCEPTING BACK UP OFFERS. Here's your opportunity to own a charming Winter Park bungalow with convenient access to 1792, I4, and all of the best shopping and dining in Winter Park, Maitland, and College Park. On the exterior of the home, you'll appreciate with the mature landscaping and the very low traffic, dead-end street that is Eland Ave. Notable systems include the roof, which was replaced in 2015 and the HVAC, which was replaced in 2022. In the backyard, the pool and hot tub provide an oasis environment that you're sure to fall in love with. The pool was resurfaced in 2023, along with new pavers, LED lighting, and tile so it looks and feels brand new! The hot tub was added in 2018 and will convey with the property. Inside, the space is perfect for entertaining and the layout is highly multifunctional. The kitchen overlooks the family room with all of its natural light and original wood flooring and there is a large bonus room, ideal for a home office or a playroom/secondary living space depending on the buyers' needs. 3 bedrooms and 2 bathrooms can be found down the hall. Additional upgrades to this property include windows, exterior LED lighting, and the irrigation system. This home is zoned for Hungerford Elementary, which is an OCPS Magnet Program for Advanced Curriculum (STEAM). In less than 10 minutes, you can get from this property to Park Avenue (6 minutes), Hannibal Square (7 minutes), Winter Park Village (5 minutes), Edgewater Drive (7 minutes), I-4 (3 minutes), Rollins College (10 minutes), and Lake Lily Park (6 minutes).

What’s better than being steps away from Park Avenue and all of the shopping, dining, and charm that downtown Winter Park has to offer? Being able to retreat to your first floor corner unit condo, complete with a designated covered parking spot, Safestep accessible bathtub, natural light in every room, and private patio to enjoy your morning coffee. Andalucia, on the corner of Interlachen and Swoope, is a .2 mile walk from Winter Park Country Club and a .4 mile walk from Central Park! This small community offers residents an unparalleled living experience in the heart of historic Winter Park, while providing a secluded, quiet atmosphere. Enjoy the mature landscaping right outside your backdoor as well as a peaceful courtyard for residents. Updates to this unit include a brand new roof (2024),  fresh paint (2024), newer flooring, appliances, and kitchen cabinetry (2019), and new light fixtures (2024). Come take a look at your new home today!

SOLD

Enjoy the finest that Winter Park, Florida has to offer in this refined lakefront property on Winter Park Chain of Lakes, Lake Mizell. Situated in the elegant neighborhood of Windsong, this well-maintained 5 bedroom, 7 bath home is ready for waterfront living, sunset entertaining, and convenient access to Winter Park’s renowned shopping and dining. Its new owners will appreciate space for 4 cars between the two garages, an expansive master suite complete with a wet bar and a private covered balcony, elevator access to the second floor, central vacuum system, and gourmet kitchen with walk-in pantry and prep space. Notable updates to this spacious property include plumbing fixtures and light fixtures, resurfaced pavers, fresh landscaping, and more. Come fall in love with the picturesque views, the 7500+ ft of luxury living, and the tree-lined street where you’re likely to encounter Windsong's resident peacocks!