Winter Park Real Estate | Winter Park Properties between $300,000 and $500,000 for Sale

4 Beds ⋅ 2 Baths ⋅ Tanglewood Sec 3 Rep SubDv. ⋅ 32792 Zip Code

**RARE WINTER PARK OPPORTUNITY!** Bring your vision to this 1959 block home situated on a spacious 0.25-acre lot in the City of Winter Park, with the prestigious Interlachen Country Club golf course directly behind the property. Whether you choose to renovate the existing 4-bedroom, 2-bath home or pursue a complete redevelopment, this property offers an exceptional opportunity to create something special in a highly desirable location. The existing home features solid block construction, 4 bedrooms, 2 bathrooms, a concrete swimming pool, and a 2019 roof, providing a great starting point for renovation or redevelopment. The generous lot and established location offer plenty of potential for a new custom residence designed to take advantage of the surrounding Winter Park lifestyle and golf-course setting. Enjoy convenient access to some of Central Florida's most sought-after amenities, including Interlachen Country Club, Park Avenue, Downtown Winter Park, Winter Park Village, Rollins College, Central Park, shopping, dining, parks, and cultural attractions. Interlachen's 18-hole championship golf course provides a beautiful backdrop just beyond the property, while Winter Park's renowned Park Avenue district offers upscale shopping, restaurants, galleries and entertainment nearby. An excellent opportunity for builders, investors, renovators or buyers looking to create their own Winter Park residence in an established setting surrounded by golf, dining, shopping and recreation.

5218 Lake Howell Road, Winter Park

$365,000

3 Beds ⋅ 2 Baths ⋅ Ridge High Sub SubDv. ⋅ 32792 Zip Code

Welcome home to Winter Park! This beautifully renovated 3-bedroom, 1.5-bath home offers the perfect combination of classic Florida living and extensive modern updates. Much of the hard work has already been done—just bring your furniture and start enjoying your new home! Step inside to discover new luxury vinyl plank flooring throughout, fresh interior paint, and a bright, refreshed feel. The renovations go well beyond what you can see, including new electrical wiring and electrical panel, new plumbing, and a new HVAC system—major improvements that add comfort and peace of mind for years to come. The exterior has also been freshly painted, giving the home a clean and inviting appearance. And then there’s the backyard! This fabulous oversized outdoor space offers plenty of room to create your own Florida retreat. Add a swimming pool, outdoor kitchen, garden, play area—or perhaps all of the above. There’s room to dream! Located in the highly desirable City of Winter Park, this renovated home provides an opportunity to enjoy one of Central Florida’s most sought-after communities without having to tackle a long renovation list yourself. New flooring, new HVAC, new electrical, updated kitchen and bath, fresh paint inside and out, plus a backyard with serious potential. Come take a look—you may have just found the Winter Park home you’ve been waiting for!

2136 Linden Road, Winter Park

$424,900

3 Beds ⋅ 3 Baths ⋅ Enclave At Hawks Crest SubDv. ⋅ 32792 Zip Code

Hawk's Crest is a care free resort style master planned community in Winter Park, Florida. With it's Modern style architecture, this 3 bedroom, 2 1/2 bathroom townhome is meticulously maintained with an HOA that covers more than most. While driving through the community you will pass the community pool and recreation area which is conveniently nestled at the end of Bantam Way. The curb appeal of the paver driveway and home design will make you feel you are home. Inside you will be greeted by a foyer before entering the home itself. On the main floor you will find a half bathroom/ guest bathroom, tile flooring throughout, excellent natural light, living room, dinette, and the statement kitchen sure to please. The kitchen boast granite counter tops, shaker style cabinets, a extra large kitchen island with a breakfast bar, ample size walk-in pantry, refrigerator 2026, all other appliances 2021, new and upgraded kitchen hardware, newer faucet, and newer large single basin sink. Upstairs you will find all the bedrooms, inside laundry room and both full bathrooms, The primary suite is an ample 20 x 15 with trey ceiling, en-suite bathroom, and walk in closet with a custom closet organizer. The en-suite bathroom is highlighted by a dual vanity sink, granite countertops, shaker style cabinets, and shower stall. Both additional bedrooms are an impressive 15 x 12 with walk in closets. The inside laundry room has upgraded cabinets. Out back you will find a quiet covered rear patio with space for seating, a grill, and more. Other highlights to mention include the tesla electric charger in the garage and freshly added cabinets and granite countertops in the drop zone just off the inside garage entrance. Community common areas include a resort style pool with covered social gathering area and a community playground. The HOA covers the cable, internet, community pool, exterior building maintenance, common area maintenance and more. Hawk's Crest is just minutes to Park Avenue Winter Park, 417, UCF, shopping, restaurants and much more. Just a short walk to the out-parcel building in the front of the community you will find local favorites like Foxtail coffee, Kelly's Ice cream, and the Park Maitland School. Don't miss this opportunity. These townhomes go quickly.

1521 Bantam Way, Winter Park

$380,000

3 Beds ⋅ 1 Baths ⋅ Winter Park Estates SubDv. ⋅ 32792 Zip Code

Mid-century style meets modern convenience in this beautifully updated Winter Park home, offering a move in opportunity with no HOA. Extensively improved since 2022, the home features refinished terrazzo floors, a full repipe, updated electrical panel, new water heater, new roof with fascia and soffit, gutters, new garage door, and a renovated open kitchen with dual induction burner and beautiful cabinetry. Additional improvements include new fencing, exterior and interior paint, drainage enhancements, new sidewalk and stepping stones, updated lighting and ceiling fans, and more. Side yard access allows ample space for boat, trailer, etc. Additional storage in the 1.5 car oversized garage. This home has been meticulously updated with love, and the sellers will contribute $10,000 towards closing costs, interest rate buy down, or home updates. Ideally located near the Winter Park YMCA, Baldwin Park, dog park, local hospitals, and zoned for Winter Park High School. Enjoy easy access to Park Avenue, with its exceptional restaurants, shopping, and charming downtown atmosphere just minutes away.

2626 Ambergate Road, Winter Park

$425,000

3 Beds ⋅ 3 Baths ⋅ Enclave At Hawks Crest SubDv. ⋅ 32792 Zip Code

Welcome to the Enclave at Hawks Crest, where this modern 3-bedroom, 2.5-bath townhome gives you 1,755 square feet of space without a long list of things to maintain. A paver driveway, two-car garage, and clean exterior make a great first impression, and inside, high ceilings and plenty of natural light keep the main level feeling open and bright. The kitchen sits right in the middle of it all with a large island, stainless steel appliances, and a walk-in pantry, opening naturally to the dining and living areas. Out back, sliding doors lead to a covered, screened patio overlooking greenspace, giving you a little breathing room without a backyard to take care of. Upstairs, the primary suite is spacious with a tray ceiling, large walk-in closet, and ensuite bath with dual sinks and a tiled shower. Two additional bedrooms sit at the opposite end of the hall, along with a second full bath and, thankfully, the laundry room is upstairs too. This home has been meticulously maintained by its original owner since 2021. The HOA handles the exterior and landscaping, and the gated community includes a resort-style pool, playground, and dog park. Zoned for A-rated Eastbrook Elementary, Tuskawilla Middle, and Lake Howell High, and you're just minutes from Park Avenue, with Kelly's Ice Cream and Foxtail Coffee a short walk from your front door. Low maintenance, high convenience, and Winter Park right outside your door. Call today for your private showing!

2349 Shadowland Loop, Winter Park

$360,000

4 Beds ⋅ 3 Baths ⋅ Ridge High Sub SubDv. ⋅ 32792 Zip Code

Great investment opportunity in Winter Park. 4 bedroom 2.5 bathroom. Large covered patio overlooks huge completely fenced back yard. New roof 2025, HVAC system 2020, water heater 2024 and upgraded electric panel re-piping of water system with Pex in 2010. Terrazzo flooring through most of the home. Excellent Seminole County neighborhood located just minutes to Downtown Winter Park, City of Orlando, Orlando International Airport, UCF & Full Sail Universities, Rollins College, Banking, Shopping & Winter Park Hospital. Within 1 hour of area attractions, Atlantic Coast Beaches, Cap Canaveral.

2122 Ridge Drive, Winter Park

$349,500

2 Beds ⋅ 1 Baths ⋅ Village Condos SubDv. ⋅ 32789 Zip Code

Virtually Staged. **Rare opportunity to own in the highly desired Downtown of Winter Park for under $350,000!** Enjoy the highly desired downtown Winter Park lifestyle with Park Avenue’s boutiques, restaurants, cafés, arts and culture, Rollins College, the Winter Park Train station, Casa Feliz, seasonal festivals and community events all just a short walk from your front door. This charming 2-bedroom, 1-bath condo offers an inviting open-concept living and dining area, along with a kitchen featuring granite countertops and convenient counter seating. Condo is highlighted with beautiful plantation shutters. Located within a charming, intimate condominium community, it offers a wonderful combination of comfort, location and low-maintenance living, all within an area known for its highly regarded Winter Park-area schools. Whether you’re searching for a primary residence, a second home, a great option for downsizing, or an investment property, this is your opportunity to own a piece of one of Central Florida’s most desirable cities. Imagine strolling to dinner on Park Avenue, meeting friends for coffee, walking to Rollins College, enjoying the beauty and history of Casa Feliz, browsing the shops, attending an art festival or catching the train — all without worrying about finding a parking space. Simply walk out your front door and enjoy the incredible lifestyle that makes Winter Park such a special place to call home. **Opportunities to own downtown Winter Park real estate at this price point are rare. Don’t miss your chance — schedule your private showing today before this one is sold. A location and lifestyle like this won’t last long!**

500 N Pennsylvania Avenue Unit G, Winter Park

$495,000

4 Beds ⋅ 2 Baths ⋅ Wrenwood Unit 3 3rd Add SubDv. ⋅ 32792 Zip Code

UPDATED 4-BEDROOM POOL HOME IN WINTER PARK WITH NO HOA! Welcome to 3020 Nicholson Drive, a beautifully updated 4-bedroom, 2-bath home with a private pool, 2-car garage, and NO HOA, tucked into the established Wrenwood neighborhood of Winter Park. From the thoughtfully updated interior to the backyard designed for Florida living, this home offers the space, flexibility, and location you've been looking for. Step inside to a bright and inviting interior featuring new LVP flooring throughout, a split-bedroom floor plan, and multiple living and dining spaces that provide plenty of room to spread out, gather, and entertain. The kitchen features abundant cabinetry and counter space, stone countertops, a built-in oven and cooktop, and a window overlooking the backyard. Custom epoxy flooring in the kitchen and entry adds durability and a unique finishing touch. The primary suite is one of the home's standout spaces, featuring a beautifully remodeled bathroom with a double vanity and an oversized glass-enclosed shower, along with a custom-built closet with shelving and organization designed to maximize storage and functionality. But the backyard may be where you'll want to spend most of your time. Step outside to a private in-ground pool, covered screened patio, fenced backyard, and an expanded pool deck with additional pavers, creating multiple spaces to lounge, entertain, dine outdoors, or simply enjoy the Florida sunshine. There's even green space beyond the pool, giving the backyard a more open feel than you might expect from a pool home. The home also offers important improvements already completed for you, including a roof replaced in 2019, re-pipe completed in 2013, and HVAC system replaced in 2018/2019. A professionally installed security system and security cameras add another layer of functionality. The location ties it all together. Situated in Winter Park's Wrenwood neighborhood, 3020 Nicholson Drive puts you within easy reach of some of Central Florida's favorite destinations, including Park Avenue, Winter Park Village, and Baldwin Park, with shopping, dining, entertainment, and everyday conveniences nearby. Convenient access to SR 436 and the 408 also makes it easy to reach Downtown Orlando and destinations throughout Central Florida.

3020 Nicholson Drive, Winter Park

$365,000

3 Beds ⋅ 3 Baths ⋅ Cranes Creek SubDv. ⋅ 32792 Zip Code

Beautiful, move in ready townhouse located in the highly desirable area of Winter Park. This well-maintained home provides confort, convenience and a versatile layout perfect for modern living. Featuring a spacious 2 car garage and a flexible 4th room on the first floor, ideal for a home an office, guest bedroom or additional living space. Enjoy being just minutes from shopping, dining and everyday essentials, all while living in a quiet and attractive community. This home is the perfect blend of style, functionality and location. Ready for its next owner.

7506 Cranes Creek Court Unit 30, Winter Park

$384,000

32792 Zip Code

BUSINESS OPPORTUNITY – Established Winter Park veterinary practice available for acquisition. Winter Park 436 Pet Doc Hospital operates from a highly visible location at 1810 State Road 436 (Semoran Blvd), providing excellent access to Winter Park, Casselberry and the greater Orlando market. Opportunity to acquire an established veterinary operation rather than building a practice from the ground up. Contact listing agent for information regarding financials, equipment/assets, occupancy terms and additional business details.

1810 State Road 436, Winter Park

$309,900

3 Beds ⋅ 3 Baths ⋅ Cranes Crk SubDv. ⋅ 32792 Zip Code

Welcome home to this inviting 3-bedroom, 2.5-bath townhome offering a comfortable floor plan and several recent updates. All three bedrooms are conveniently located on the second floor and feature newly installed carpet, providing a fresh and comfortable feel. The main living areas feature easy-care ceramic tile throughout the living room and dining room, as well as in the bathrooms. The kitchen is equipped with new appliances, including a range/oven, dishwasher and microwave, making it ready for its next owner. An interior laundry area conveniently located near the kitchen helps make everyday chores a little easier. The interior has also been recently painted, giving the home a clean, refreshed appearance. Sliding glass doors from the dining room lead directly to the patio, providing a great spot for morning coffee, outdoor dining or simply enjoying some fresh Florida air. An attached one-car garage provides the added convenience of covered parking and additional storage. With new carpet, fresh interior paint, new kitchen appliances and a functional 3-bedroom layout, this townhome is ready for you to make it your own. Schedule your showing today!

7530 Cranes Creek Court, Winter Park

$415,000

3 Beds ⋅ 2 Baths ⋅ Albert Lee Ridge SubDv. ⋅ 32789 Zip Code

Welcome home to this adorable and beautifully updated 3-bedroom, 2-bathroom home in the heart of Winter Park! From the moment you arrive, the cheerful teal front door adds the perfect pop of color and sets the tone for the charm you’ll find throughout. **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Step inside to the inviting living room, where the home’s original hardwood floors immediately make an impression. Just beyond, the formal dining room and updated kitchen create a comfortable flow for both everyday living and entertaining. The kitchen features newer 2024 appliances, granite countertops, and plenty of character, blending modern convenience with the timeless feel of the home. French doors open from the living area to what may be the showstopper of the property - a massive, newly fenced backyard offering an incredible amount of space for entertaining, gardening, pets, play, or simply enjoying the outdoors. And for something truly special, the backyard features a custom treehouse built directly into the tree, creating a one-of-a-kind feature you won’t find in just any home. All three bedrooms are thoughtfully positioned down the hallway, with the primary bedroom tucked away at the back for added privacy with its own ensuite bathroom with a generously sized shower. The thoughtful updates, including a 2019 roof, double-pane windows, updated electrical panel, and updated plumbing, provide peace of mind while preserving the home’s classic details, creating a space that feels both move-in ready and full of personality. And then there’s the location! Enjoy easy access to I-4, making commutes and exploring Central Florida a breeze, while being just minutes from the shopping, dining, and entertainment of Winter Park Village and Park Avenue. With amazing shopping and everyday conveniences right around the corner, this home puts the best of Winter Park within easy reach. Charming, updated, full of character, and sitting on an incredible backyard — this is a Winter Park home you won’t want to miss!

2126 Albert Lee Parkway, Winter Park

$450,000

5 Beds ⋅ 3 Baths ⋅ Ridge High 1st Add SubDv. ⋅ 32792 Zip Code

Welcome to 2181 Linden Road, where modern updates meet the everyday convenience of Winter Park living. Thoughtfully renovated and designed with flexibility in mind, this home offers a versatile layout, contemporary finishes, and a private separate-entry suite that adds valuable space for guests, a home office, or additional living arrangements. With no HOA, the property offers added flexibility rarely found in this sought-after area. The location is a standout. Enjoy easy access to Winter Park’s renowned Park Avenue, with its boutiques, restaurants, cafés, galleries, and local events, while nearby Winter Park Village adds even more shopping, dining, entertainment, and everyday conveniences. Outdoor enthusiasts will appreciate close access to the Cross Seminole Trail, Lake Baldwin Park, the Winter Park Chain of Lakes, scenic parks, and recreational opportunities. Downtown Orlando, major employment centers, Advent Health Winter Park, Rollins College, Full Sail University, SR-436, SR-426, and I-4 are also conveniently accessible. Winter Park continues to invest in its future, with ongoing improvements to Park Avenue, expanded infrastructure and streetscape enhancements, and a citywide Parks & Recreation Master Plan focused on improving parks, trails, open spaces, recreation, and community facilities for years to come. This is more than a renovated home it is an opportunity to enjoy the lifestyle, connectivity, character, and continued growth that make Winter Park one of Central Florida’s most desirable places to call home.

2181 Linden Road, Winter Park

$475,000

2 Beds ⋅ 2 Baths ⋅ Winter Park Pines Rep SubDv. ⋅ 32792 Zip Code

Welcome to this charming 2 bedroom, 2 bath home, with light and bright open floor plan, spacious rooms and many updates and upgrades. Roof was replaced (2019), new A/C (8/26), fully renovated kitchen with quartz counters, cabinetry, and stainless appliances. Pella double pane windows (2020), new French doors and interior doors, and new soffits and gutters in 2025. Enjoy outdoor living in the lanai overlooking a large fenced backyard with native landscaping. This highly desired neighborhood offers excellent schools, quiet streets, community pool, hiking and biking trails, and nearby public golf course. Live minutes from Advent Hospital, city conveniences, downtown Park Avenue shops and restaurants. Also easy access to neighboring towns, Orlando and airports. This is a perfect starter home or downsize home for those want all the comforts and privacy of a home, neighborhood and community in smaller space and are not ready for an apartment and high HOA fees.

2824 Prince John Road, Winter Park

$340,000

2 Beds ⋅ 1 Baths ⋅ Olympia Heights SubDv. ⋅ 32789 Zip Code

Welcome home to this charming 2-bedroom, 1-bathroom gem nestled in the heart of Winter Park AND College Park. This charming single-story concrete-block home blends timeless character with everyday convenience. It has a dimensional-shingle roof, and a full-length driveway leading to a covered carport deliver lasting value and practical, protected parking with an attached laundry & storage room. Located just minutes away from Downtown Orlando, Disney, Universal and Advent Health, this sought-after location offers convenience and comfort. This home boasts not only a prime location but also a cozy ambiance that will make you feel right at home. With its Terrazzo floors adding warmth and character, and the spacious fenced-in backyard providing privacy and room for outdoor activities, this property is ideal for those seeking the perks of Winter Park and College Park living as well as the fun outgoing, Orlando attractions.

1941 Oglesby Avenue, Winter Park

$359,000

3 Beds ⋅ 3 Baths ⋅ Aloma Trails SubDv. ⋅ 32792 Zip Code

Virtually Staged! Amazing Townhome! GATED Community of Aloma Trails Townhomes in a great Winter Park location, 3 bedroom, 2.5 bathroom with features of spacious living and comfortability. This stunning Townhome has Ceramic Tile flooring throughout the first floor leads to a kitchen with all the upgrades including SS appliances. 42” Cabinets, upgraded granite countertops and backsplash, and an island with plenty of seating along with a carpet in the second floor and all bedrooms. The master suite is outfitted with large Walk-In closet, glass-enclosed shower with dual sinks, and oversized cabinets. The two additional bedrooms share a second full bath and there is a half bath on the main floor convenient for guests. Separated interior laundry closet provides convenience and comfort. A nice big Car Garage and driveway, which will easily suit for multiple vehicles as necessary. This community comes with hassle-free lawn care, and well-maintained common areas and a BEAUTIFUL location. The fitness enthusiast will enjoy the Crunch Fitness facility just across the community and, the CADY WAY trail and the CROSS SEMINOLE trail- all just steps away from your front door. Walmart, Costco and Publix are almost 3 min driving distance. Close to Park Ave in Winter Park, SR 417, UCF, Fulsail University, and just 40 minutes to the Beach! Add in top notch Seminole County Schools. You don't need to look any further for your Dream Home! Schedule your viewing today! Note: Some of the pictures are showing the virtual staging of the unit and the furnitures/decorative items are not included to the listing.

7605 Aloma Pines Court, Winter Park

$429,998

3 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 8 SubDv. ⋅ 32792 Zip Code

Welcome home to 2112 Eastbrook Blvd, a fully remodeled gem tucked into the sought-after Eastbrook neighborhood of Winter Park! This 3-bedroom, 2-bathroom home has been fully remodeled and made to entertain. From the kitchen to the patio, it's perfect for your family gatherings. It also sits on a spacious .23 acre lot, one of the biggest perks of this property and a huge opportunity for buyers who want room to garden, entertain, play, or simply spread out in their own backyard oasis. Step inside and you'll find durable, low-maintenance porcelain tile flooring throughout the main living areas, with waterproof laminate flooring in all the bedrooms. It's a stylish, practical combination that's as easy to love as it is to live with. The kitchen is truly the heart of this home. Crisp white cabinetry offers plenty of storage, black stainless steel appliances add a modern touch, and the oversized island (finished with its own contrasting gray cabinetry) creates the perfect gathering spot for cooking, casual dining, or entertaining guests. It flows right out to the patio for effortless indoor to outdoor entertaining. The primary suite features a beautifully updated en-suite bathroom with a sleek walk-in shower, offering a clean, spa-like feel. This home isn't just cosmetically updated. The big-ticket items are done too: the electric panel was replaced in January 2025 and the home has new AC units, giving buyers real peace of mind on top of the style. You'll also find a 2-car garage and an oversized driveway with plenty of extra parking, all wrapped around a completely remodeled interior from top to bottom. This home is truly move-in ready. With no HOA, a prime Winter Park location, and a lot size that's hard to find at this price point, 2112 Eastbrook Blvd is a rare opportunity for buyers looking for space, style, and flexibility. Homes like this, fully renovated with an oversized lot and no HOA, don't come around often in this area. Schedule your showing today!

2112 Eastbrook Boulevard, Winter Park

$450,000

4 Beds ⋅ 2 Baths ⋅ Howell Estates Rep SubDv. ⋅ 32792 Zip Code

The one you’ve been waiting for! This beautifully redesigned home offers 4 bedrooms, 2 bathrooms, and nearly 1,700 square feet of thoughtfully curated living space. Manchester offers both style and peace of mind with major upgrades including a 2026 A/C, 2024 roof, 2026 windows, Brand new privacy fence, 2026 garage door, and 2026 electrical panel. At the heart of the home is a stunning designer kitchen featuring custom wood cabinetry, Taj Mahal countertops, a dedicated coffee bar, and an open layout designed for both entertaining and everyday living. Every space has been intentionally designed to be as functional as it is beautiful, with a split floor plan, custom bathrooms, and ample storage throughout. The private primary suite is thoughtfully positioned on its own side of the home and features a walk-in closet and en-suite bathroom. Situated on an oversized lot, the spacious backyard offers plenty of room for entertaining, playing, and making memories. With beautiful finishes, extensive upgrades, and zoning for A-rated schools, Manchester is one you won’t want to miss. Come see it before it’s gone!

1011 Manchester Circle, Winter Park

$409,900

3 Beds ⋅ 3 Baths ⋅ Grayson Square SubDv. ⋅ 32792 Zip Code

Almost brand new and move in ready CORNER townhome in Winter Park! This beautiful 3 bedroom 2.5 bathroom home with just under 1,800 sq. ft. offers a large 2 car garage, light and bright living spaces, clean and modern designer features, and comes equipped with a full kitchen appliance package and washer/dryer. The first floor offers expansive living spaces with enough room for a dining area and family room. All of which flow seamlessly into the open kitchen. With white cabinets and Quartz counter tops, the kitchen is a show stopper! The entire first level is adorned with tile and offers a half bathroom and access to the covered back porch. Just up the stairs, you will find all of your bedrooms and full bathrooms. The primary bedroom and en suite bathroom are ample in size and also offer a large walk in closet. Both secondary bedrooms are down the hall and share a large full bathroom. The small gated community of townhomes offers a community pool and serene pond. HOA includes cable! Make sure to put this on your must see list!

2857 Clever Lane, Winter Park

$419,000

4 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 06 2nd Rep SubDv. ⋅ 32792 Zip Code

Virtually Staged. Modern design , open concept layout , sleek quartz counter top , all new appliances, new luxury vinyl plank flooring, new lanai upgrade. This beautiful 4 bedroom and 2 full bath is situated on a 8,250 square feet lot, which was newly fenced in 2024 which gives a sense of privacy and spaciousness. As you exit the interior through the French door into the lanai . There is two detached shed for your storage convenience. This beautiful done home was renovated in ,2024 with lot of upgrades and it is situated in desirable winter Park , which is close proximity to shopping, downtown ,highways , airport , universities( U.C.F) etc. No H.O.A fees ,the open concept layout gives this home a sense of comfort , convenience , spaciousness and a pleasant and relaxing ambiance. The home is move in ready and the front yard is ready for your customized landscape.Be the lucky one to own this home.Roof was redone in February/2020.

1842 Puritan Avenue, Winter Park

$499,000

4 Beds ⋅ 2 Baths ⋅ Olympia Heights Annex SubDv. ⋅ 32789 Zip Code

Income Producing Duplex in Winter Park, Florida! Great investment opportunity in a desirable location! This duplex features two 2-bedroom, 1-bath units, each approximately 600 square feet, with private entrances, central AC, and a private screened patio area. Both units are currently leased, providing established rental income and long-term occupancy. Each unit offers a spacious living area and a functional kitchen, with a shared laundry room equipped with a washer and dryer for added convenience. Both units include a full bath with updated showers. Enjoy all of Downtown Winter Park, including the shops and restaurants along Park Avenue, Winter Park Village, and an abundance of entertainment and recreational options such as Mead Botanical Garden, Winter Park Tennis Center, Winter Park Golf Course, and much more. The property also offers easy access to major highways and is just minutes from Rollins College. Don't miss this opportunity to own an income-producing property in one of Central Florida's most desirable areas with no HOA. Pictures were taken prior to occupancy.

2183 Crandon Avenue, Winter Park

$410,000

3 Beds ⋅ 2 Baths ⋅ Lake Bell Terrace SubDv. ⋅ 32789 Zip Code

Nestled in Winter Park's Lake Bell Terrace neighborhood, this 3 bedroom, 2 bathroom home is located close to everything that makes Winter Park special, Park Avenue's shops and restaurants, Winter Park Village, Mead Botanical Garden, the Winter Park golf course, and more. Inside, an open, light-filled living area flows effortlessly into the kitchen and dining room, with wood and tile flooring throughout. A large bonus room adds flexible space for a home office, playroom, or media room, while the spacious bedrooms and abundant storage make everyday living easy. Outside, a classic front porch invites cozy mornings with coffee, a screened patio provides year-round outdoor living, and the beautiful backyard with additional open patio is perfect for grilling and gathering. A dedicated laundry/utility room and attached 1 car garage complete this Winter Park gem.

1955 Eland Avenue, Winter Park

$425,000

3 Beds ⋅ 2 Baths ⋅ Oakcrest-516 SubDv. ⋅ 32792 Zip Code

Welcome to this beautifully updated 3-bedroom, 2-bathroom home nestled in a quiet and desirable Winter Park neighborhood. From the moment you arrive, you’ll appreciate the lush new front landscaping and inviting curb appeal. Inside, the open-concept floor plan creates a spacious and welcoming atmosphere, complemented by soaring vaulted ceilings and beautiful brand-new tile flooring throughout the home. The thoughtfully designed split floor plan provides excellent privacy, with the primary suite separated from the additional bedrooms. The spacious living areas flow seamlessly into the kitchen and dining spaces, creating an ideal layout for both everyday living and entertaining. Fresh, modern finishes throughout make this home truly move-in ready. Step outside to your brand-new backyard pavers, creating a beautiful outdoor space perfect for relaxing, entertaining, or enjoying Florida’s year-round sunshine. With a 2-car garage, stunning updates, beautiful landscaping, and a peaceful neighborhood setting, this Winter Park home offers the perfect combination of comfort, style, and location.

7384 Grand Avenue, Winter Park

$499,000

3 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code

Charming 1950 block bungalow in sought-after Orwin Manor! This inviting 3-bedroom, 2-bath home sits on a generous corner lot with a side-load driveway and garage, offering added breathing room, curb appeal, and convenience. A paver walkway leads to the covered front porch, setting the tone for the home’s classic character and welcoming appeal. Inside, original hardwood floors complement a renovated, generously sized kitchen—ideal for everyday living and entertaining. Recent improvements include a 2020 roof, 2021 HVAC system, plus new windows, doors, and added insulation. The dining room features French doors opening to a newly poured concrete patio and charming backyard offering loads of potential for gardening, play, pets, or creating your own private outdoor retreat. Previously utilized as an investment rental, this property presents an excellent opportunity for an owner-occupant or investor seeking a desirable Winter Park location with strong rental appeal. Enjoy close proximity to AdventHealth’s world-class Orlando campus, as well as the shopping, dining, and lifestyle destinations of Winter Park, Park Avenue, Mills 50, and downtown Orlando. A wonderful opportunity to own a character-filled home in one of the area’s most desirable central neighborhoods.

1652 Berkshire Avenue, Winter Park

$400,000

3 Beds ⋅ 2 Baths ⋅ Garden Grove SubDv. ⋅ 32792 Zip Code

Completely renovated 3bed/2bath, split floorplan, single family home in the heart of Winter Park. With brand new roof, updated kitchen and bath, brand new stainless steel appliances, new interior and exterior paint, new porcelain tiling in all wet areas, and new laminate flooring in all bedrooms. Other highlights include a brand new front storm door, tiled screened patio and garage floors, brand new vinyl sidings, and a spacious fenced backyard, suitable for gardening, family gatherings and entertainment. Schedule, and check out this beauty today!

5588 Garden Grove Circle, Winter Park

$339,900

3 Beds ⋅ 2 Baths ⋅ Fairview Heights Rep SubDv. ⋅ 32789 Zip Code

Opportunity awaits in this 3-bedroom, 2-bath concrete block home located in the established Fairview Heights area of Winter Park. Offering 1,344 square feet of living space on a 6,460-square-foot lot, this single-story residence features a functional floor plan with tile flooring throughout the main living and dining areas. A covered rear entry leads to a brick paver patio and a fully fenced backyard with mature trees, providing space for entertaining, pets, or outdoor enjoyment. According to the seller, the roof was replaced approximately 10 years ago and the HVAC system approximately 6 years ago. Buyers are encouraged to verify all information and permits. The property is currently tenant-occupied on a month-to-month lease and may be delivered vacant at closing with a minimum of 30 days' notice, or continue as an investment opportunity. No HOA. Conveniently located near shopping, dining, parks, major roadways.

310 Granada Drive, Winter Park

$495,000

3 Beds ⋅ 2 Baths ⋅ Woodcrest Unit 5 SubDv. ⋅ 32792 Zip Code

Welcome to 5316 Halyard Court, a beautifully updated pool home nestled in the heart of Winter Park. This move-in-ready residence offers the perfect blend of modern finishes, comfortable living spaces, and an incredible backyard designed for enjoying the Florida lifestyle. From the moment you arrive, you'll appreciate the inviting curb appeal, updated front entry, and thoughtfully maintained interior. Inside, the home features an open and functional layout accented by luxury wood-look flooring throughout, neutral designer colors, crown molding, recessed lighting, and abundant natural light. The spacious living areas flow seamlessly together, creating an ideal setting for both everyday living and entertaining. The generously sized bedrooms provide flexibility for families, guests, or a home office, while the updated bathrooms offer clean, contemporary finishes. The primary suite serves as a comfortable retreat with its own private en-suite bath. Step outside to your own private oasis featuring a sparkling in-ground pool surrounded by an expansive travertine paver deck, a screened lanai perfect for year-round relaxation, and a fully fenced backyard shaded by mature trees. Whether you're hosting weekend barbecues, enjoying a quiet evening by the pool, or letting pets and family play, this outdoor space offers endless possibilities. Additional upgrades include owned solar panels for enhanced energy efficiency and long-term savings, an attached two-car garage, and a spacious lot that provides both privacy and room to enjoy the outdoors. Ideally located, this home is just minutes from Downtown Winter Park and the renowned Park Avenue shopping and dining district, Rollins College, Full Sail University, AdventHealth Winter Park, UCF, Valencia College, and numerous parks, golf courses, and recreational amenities. Convenient access to SR-417, SR-436, University Boulevard, and Aloma Avenue makes commuting throughout Central Florida simple and efficient. Combining an exceptional location with modern updates and resort-style outdoor living, 5316 Halyard Court is a rare opportunity you won't want to miss.

5316 Halyard Court, Winter Park

$389,900

3 Beds ⋅ 3 Baths ⋅ Grayson Square SubDv. ⋅ 32792 Zip Code

Welcome home to this beautifully maintained, nearly new Pulte Townhome in the heart of Winter Park! Built in 2023, in the gated community of Grayson Square, this stylish two story residence offers 3 bedrooms, 2.5 bathrooms, and an attached one car garage, combining modern design with everyday convenience. The open-concept main living area is perfect for entertaining, featuring elegant quartz counter-tops, Whirlpool stainless steel appliances, ample cabinet space, and a large island overlooking the living and dining areas. Enjoy the upgraded smart home technology, high speed internet and cable already included into the low HOA, making working from home and streaming effortless. Upstairs, you will find a spacious primary suite complete with a generous walk-in closet and a private en-suite bathroom designed for comfort and relaxation. Two additional bedrooms provide plenty of room for family, guests. or a dedicated home office. Also to note is that there are no direct rear neighbors, allowing you to enjoy peaceful outdoor views on the back covered patio. The community is beautifully maintained and offers a resort-style pool and cabana and sidewalks for evening strolls. One of the homes most desirable features is the one thing you need the most but comes unseen is the 10 year transferable Pulte home warranty. Located just minutes from Winter Parks renowned shopping, dining, entertainment, parks and top commuter routes like 417, you'll enjoy easy access to everthing Central Florida has to offer while coming home to a quiet, friendly neighborhood. If your looking for a modern, energy efficient home with premium finishes and virtually maintenance free simple living, this is the one youve been waiting for!

2017 Canny Cove, Winter Park

$449,000

3 Beds ⋅ 2 Baths ⋅ Stansbury Estates SubDv. ⋅ 32789 Zip Code

Tucked away on a quiet street just minutes from the heart of Winter Park, this beautifully updated bungalow offers the perfect blend of character, modern updates, and flexibility. The true standout is the detached 1-bedroom, 1-bath guest house, a rare feature that's ideal for visitors, a private home office, fitness studio, creative space, or even an income-producing opportunity. The main home features two spacious bedrooms and a beautifully renovated bathroom, while timeless charm is showcased throughout with original hardwood floors, crown molding, custom built-ins, and an open-concept living space. The thoughtfully designed kitchen combines butcher block and custom concrete countertops with quality appliances, while the adjacent laundry and utility room adds extra functionality. Step outside to a backyard designed for year-round Florida living. The covered patio, complete with café lighting and ceiling fans, overlooks a fully equipped outdoor kitchen with custom concrete countertops, creating the perfect setting for entertaining. Lush tropical landscaping, an outdoor shower, and abundant storage complete the private outdoor oasis. Beyond its charm, this home is packed with practical upgrades including a metal roof, whole-house natural gas generator, and an exterior security camera system, providing comfort and peace of mind through every season.

2007 Cornell Avenue, Winter Park

$435,000

3 Beds ⋅ 2 Baths ⋅ Garden Lake Estates Unit 1 SubDv. ⋅ 32792 Zip Code

This is an Excellent split plan pool home. Tile floors in the Family room, Living Room, and Dining room keep with the Florida syle. The bedrooms feature wood floors in all the bedrooms.The screened in pool is also heated and has a Heated Spa. It is conveniently located in Seminole County with a Winter Park address. It also features a ROOF that is only two years old ! You can cool off in the screened in pool on hot days. During the cooler time of year you can use the Heater for both the pool and Spa.The screen enclosure helps to make the pool more inviting. You also have a covered porch area for entertaining. There is yard space that is fully fenced. The back yard also has a shed for storing your yard tools. SOLD AS IS. Contact the Listing Agent for a personal tour !

3740 Hawthorne Lane, Winter Park

$425,000

3 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 06 SubDv. ⋅ 32792 Zip Code

Discover the epitome of comfortable living in this fantastic single-family home situated on a generous and spacious corner lot. This meticulously renovated property features 3 bedrooms and 2 bathrooms, offering a perfect blend of modern style and cozy charm. Step inside to experience the allure of an open floor plan that seamlessly connects the living spaces. The kitchen, fully renovated and boasting a contemporary design, is the heart of this home—a perfect gathering place for family and friends. Indulge in the luxury of a private backyard oasis, where tranquility meets outdoor enjoyment. A delightful retreat awaits with a nice backyard, ideal for entertaining or simply unwinding under the stars. Plus, your vehicles and recreational gear are well taken care of with a 2-car garage and an additional boat space. The charm continues outdoors with a great covered lanai, providing the perfect setting for al fresco dining or cozy evenings by the fireplace. Every detail of this home has been thoughtfully curated to enhance your lifestyle. Don't miss the opportunity to make this Winter Park residence your own—where spacious living, thoughtful design, and comfort converge. Schedule your tour today and envision the possibilities that await in this truly remarkable home!

1886 Clematis Lane, Winter Park

$420,000

3 Beds ⋅ 2 Baths ⋅ Howell Branch Woods SubDv. ⋅ 32792 Zip Code

Virtually Staged. Discover this spacious 3-bedroom, 2-bathroom home offers 1,483 sq ft of comfortable living space with a functional layout and plenty of room for everyday living. The home features a well-appointed kitchen, open living areas, and generously sized bedrooms. Outside, enjoy a private backyard with a swimming pool, creating the perfect space for relaxing, entertaining, and enjoying the Florida lifestyle.

5409 Albert Drive, Winter Park

$339,000

3 Beds ⋅ 2 Baths ⋅ Eastbrook Subd Unit No 05 SubDv. ⋅ 32792 Zip Code

Welcome to this beautifully updated 3-bedroom, 2-bath home in beautiful Winter Park! This move-in-ready property features stylish wood-look tile flooring throughout, creating a seamless, modern look that's both attractive and easy to maintain. The home has two beautifully renovated bathrooms with contemporary finishes, along with a newer A/C and a new roof in 2026. The air-conditioned laundry room has plenty of storage space. Step outside to your spacious, fully fenced backyard, where you'll find plenty of room to entertain, play, or unwind around the cozy fire pit. The generous outdoor space offers endless possibilities for gatherings, gardening, or simply enjoying Florida's beautiful weather. A rare highlight is the oversized swing gate providing convenient side-yard access with ample room to park an RV, boat, trailer, or other recreational vehicles. Zoned for Seminole County Schools (A Rated school zone 2025/2026)! Best of all, there's no HOA, giving you the freedom to make the most of your property without additional HOA restrictions. Perfectly situated just minutes from Costco, grocery stores, shopping, dining, and the popular Cady Way Trail, this home offers the ideal combination of comfort, convenience, and outdoor recreation. With easy access to major roadways and everything Winter Park has to offer, this home truly has it all. Welcome home!

3562 Bougainvillea Drive, Winter Park

$464,000

3 Beds ⋅ 2 Baths ⋅ Casa Aloma SubDv. ⋅ 32792 Zip Code

Okay, let's talk about this one. Yes, there's green carpet. Yes, it needs your vision. I know exactly what you're thinking right now. But hear me out, because this house has some things going for it that are genuinely hard to find. Start with the location. In under 10 minutes in any direction, you could be having lunch on Park Ave, shopping at Altamonte Mall, or launching your boat up in Maitland. That kind of range is rare in Central Florida, and this spot has it. And there's no HOA here, which if you know, you know. Then there's the pool. A real pool, tucked behind a block wall for total privacy, so you can actually enjoy it without the whole street watching. That kind of setup doesn't come around often. This is a 3 bedroom, 2 bath home with real bones and real space. The layout gives you room to breathe, and the systems that actually matter have already been taken care of. Water heater, brand new in 2026. HVAC, also brand new in 2026. Roof was done in 2025. Plumbing was updated in 2017. So the expensive, unglamorous stuff, the stuff that actually protects your investment, is already handled. The home has been professionally cleaned and pressure washed, so it's not just clean, it's move in ready clean. You could genuinely move in as is and update it slowly, on your own timeline, as your taste and budget allow. No rush. No pressure. Just a solid home with good bones, a pool, an unbeatable location, and all the boring but important stuff already done for you. Sometimes the right house isn't the one that's already finished. It's the one that's ready for you to finish it.

2703 Tierra Circle, Winter Park

$499,000

Aloma SubDv. ⋅ 32792 Zip Code

Medical Office Conversion Opportunity directly across from Advent Health Winter Park Hospital. Existing building offers potential for professional office conversion or can serve as the site for future medical or office development. Professional Office Future Land Use, outstanding visibility, and the opportunity to assemble the adjacent parcel create an exceptional investment in one of Central Florida's premier healthcare corridors.

2231 Nairn Drive, Winter Park

$499,000

Aloma SubDv. ⋅ 32792 Zip Code

Medical Office Conversion Opportunity directly across from Advent Health Winter Park Hospital. Existing building offers potential for professional office conversion or can serve as the site for future medical or office development. Professional Office Future Land Use, outstanding visibility, and the opportunity to assemble the adjacent parcel create an exceptional investment in one of Central Florida's premier healthcare corridors.

230 Strathy Lane, Winter Park

$389,000

3 Beds ⋅ 3 Baths ⋅ Grayson Square SubDv. ⋅ 32792 Zip Code

Step into this beautifully designed townhome featuring an open-concept kitchen, dining, and living area—perfect for everyday living and entertaining. The modern kitchen boasts stainless steel appliances, gray cabinetry, and quartz countertops. Upstairs, the spacious primary suite offers a walk-in closet and a private in-suite bath with dual quartz vanities, while two additional bedrooms, a full bath, and a convenient laundry closet complete the second floor. Relax on the covered lanai and enjoy the privacy of this home's cul-de-sac location. The HOA includes landscaping, exterior maintenance and repairs, high-speed internet, and access to the gated community, providing low-maintenance living. With no CDD, this home is an excellent option for both homeowners and investors. Ideally located in highly desirable Winter Park, Grayson Square is just minutes from SR-436, SR-434, and SR-417, with Publix, Starbucks, shopping, dining, and top-rated Seminole County schools nearby. Park Avenue is only a short drive away, making this home the perfect combination of convenience, comfort, and value.

2033 Canny Cove, Winter Park

$425,000

Eastgate Sub SubDv. ⋅ 32792 Zip Code

A great opportunity to own land in one of Winter Park's most sought-after pockets. This property's true value lies in its prime homesite. You can build your dream home or renovate to suit, all while capturing the location that can't be replicated. Tucked in an established, tree-lined neighborhood minutes from Park Avenue's boutiques and dining, Winter Park's chain of lakes, and easy access to I-4, this address puts you at the center of it all. Zoned for top-rated Winter Park schools, this is the kind of location families compete for. Whether you're an investor, builder, or buyer looking to create something custom, this is a foundation worth building on. Land + location + schools — the trifecta that makes Winter Park real estate hold its value.

1909 Taylor Avenue, Winter Park

$395,000

3 Beds ⋅ 2 Baths ⋅ Justamere Camp Rep SubDv. ⋅ 32789 Zip Code

Virtually Staged. Conveniently located just minutes from I-4, downtown Orlando, and Winter Park, this versatile home offers the perfect blend of comfort, flexibility, and location. The upper level features two bedrooms and one full bath, while the lower level includes one bedroom and one full bath. Each floor has its own private entrance and full kitchen, making it ideal for multi-generational living, rental income, a guest suite, or added privacy. Situated on a beautiful, tree-lined dead-end street, the property offers a peaceful setting while remaining close to shopping, dining, and entertainment. Inside, you'll find contemporary fixtures, stylish finishes, updated appliances, and an abundance of natural light throughout. The spacious backyard and inviting seating area provide the perfect space to relax or entertain family and friends. Major updates include a recently replaced roof, HVAC system, and electrical panel, offering added peace of mind. Some photos have been virtually staged to help showcase the home's layout and potential.

2568 Lotafun Avenue, Winter Park

$335,000

3 Beds ⋅ 3 Baths ⋅ Via Lago/Hanging Moss Condo SubDv. ⋅ 32792 Zip Code

Great investment opportunity, tenant occupied/income producing Winter Park property in gated community.

2526 Passamonte Drive Unit 10F, Winter Park

$414,900

4 Beds ⋅ 2 Baths ⋅ Garden Lake Estates Unit 3 SubDv. ⋅ 32792 Zip Code

Oversized corner lot in quiet neighborhood with highly desired Seminole County schools. Well-built block on slab four bedroom home with split floor plan. Enclosed large Florida room. Shed. Existing irrigation well (but pump not working--no warranty on well). Double gate to back yard for parking RV/toys (back left). Roof 2018; water heater 2018; HVAC 2017; CPVC plumbing.

1401 Aster Court, Winter Park

$368,000

4 Beds ⋅ 2 Baths ⋅ Eastbrook Sub SubDv. ⋅ 32792 Zip Code

Beautifully updated 4-bedroom, 2-bath pool home in Winter Park offering modern upgrades and flexible living space. The home features new tile flooring throughout, a fully renovated kitchen with a stunning waterfall quartz island, and two beautifully remodeled bathrooms. The garage has been updated with new flooring and a new garage door. Major improvements include a new roof (2024), new A/C (2023), complete home repipe (2022), updated electrical panel, and pavers in both the front and back of the home. The swimming pool was resurfaced with new tile in 2023 and is approximately 12 feet deep, creating the perfect backyard retreat.

885 Carnation Drive, Winter Park

$439,900

3 Beds ⋅ 1 Baths ⋅ Pines SubDv. ⋅ 32789 Zip Code

Seller is highly motivated. Competitively priced for a quick sale. Don't miss your opportunity to own this beautiful home! First time on the market in over 60 years! Filled with decades of cherished family memories, this beloved home is ready for its next chapter. Located in the highly desirable Winter Park 32789 ZIP code, 2041 Jewell Avenue offers an unbeatable location just minutes from Dubsdread Golf Course, College Park, and downtown Winter Park, with quick access to I-4, making commuting throughout Central Florida a breeze. Lovingly maintained and thoughtfully updated over the years, the home features a 2024 roof, central air conditioning, and a large, wheelchair-accessible walk-in shower, providing enhanced comfort and accessibility. The spacious, fully fenced backyard offers plenty of room to relax, entertain, garden, or play. Situated on a quiet dead-end street, you'll enjoy minimal traffic and a peaceful neighborhood setting. The original fourth bedroom has been converted into a generous laundry room, adding convenience and extra storage while offering flexibility for future customization if desired. Whether you're looking to move right in, renovate, or create your dream home in one of Central Florida's most sought-after neighborhoods, this property presents an exceptional opportunity. Now it's your turn to create a lifetime of memories and make this treasured home your own.

2041 Jewell Avenue, Winter Park

$424,400

1 Beds ⋅ 1 Baths ⋅ Knowles Manor North Condo SubDv. ⋅ 32789 Zip Code

Virtually Staged. LOCATION! LOCATION! LOCATION! Welcome to Knowles Manor...a charming 11 unit condo perched on quiet brick street in the heart of Olde Winter Park...just steps from the Winter Park 9 golf course, Casa Feliz, and the boutiques, restaurants, and vibrant lifestyle of Park Avenue, this location is hard to beat. This delightful first-floor residence is the perfect place to call home or an ideal pied-a'-terre for seasonal living. Inside you'll find easy maintenance tile flooring throughout, a full kitchen and bath, abundant closet space, and an adorable screened rear porch-perfect for relaxing with your morning coffee or unwinding at the end of the day. Additional highlights include a quaint community patio, one assigned parking space steps from your front door, a new HVAC system installed in 2021, and a new roof 2025. Whether you are looking for a full time residence, a weekend retreat, or a low maintenance Winter Park getaway, this charming condo is ready to welcome you home. HOA $217 per month!! Welcome Home!

644 N Knowles Avenue Unit 3, Winter Park

$494,999

2 Beds ⋅ 1 Baths ⋅ Seville Park SubDv. ⋅ 32789 Zip Code

Charming renovated bungalow on a brick street in the heart of Winter Park! Recently updated with new finishes and appliances throughout. Huge back yard with plenty of potential space for ADU! Move in ready, no HOA, and just a short stroll from Rollins College and beautiful Park Avenue. A rare must see opportunity!

981 Aragon Avenue, Winter Park

$449,900

3 Beds ⋅ 2 Baths ⋅ Orange Terrace SubDv. ⋅ 32789 Zip Code

WOW! NEW PRICE! $10,000 SAVINGS!! RENOVATED AND MOVE IN READY! Make this beautiful three-bedroom, two-bath home in desirable Winter Park 32789 your next place to call home! Extensively updated throughout, this home offers the perfect blend of modern style, comfort and convenience. Filled with natural light, this home features a beautifully renovated kitchen with an open pass-through breakfast bar and seating, ideal for entertaining and everyday living, a large stainless sink beneath a window and plenty of stunning quartz countertop space. Both baths have been tastefully remodeled, and nearly every aspect of the home has been thoughtfully updated to create a fresh, contemporary feel. Major improvements provide added peace of mind, including a new roof in October 2023, an HVAC system in 2023 and a water heater in 2024. Enjoy the convenience of a large covered carport with built-in storage, plus a huge backyard with endless possibilities for gardening, pets, play or future expansion. An additional storage shed, added in 2018, offers even more space for tools, hobbies and outdoor equipment. Ideally located with quick access to Interstate 4 and 17-92 and just minutes from Park Avenue, Winter Park Village, College Park and Downtown Orlando, you'll enjoy some of Central Florida's finest shopping, dining, entertainment and cultural attractions right at your fingertips. All this and NO HOA! Combining extensive renovations, major system updates, an oversized backyard in an unbeatable and convenient location, this exceptional Winter Park home is truly move-in ready and waiting for its next owner. Call to schedule your appointment today!

259 Orange Terrace Drive, Winter Park

$465,000

3 Beds ⋅ 2 Baths ⋅ Garden Lake Estates Unit 1 SubDv. ⋅ 32792 Zip Code

Welcome to this beautifully maintained 3-bedroom, 2-bathroom home nestled in the highly desirable Winter Park area. Combining comfort, style, and an unbeatable location, this charming residence offers the perfect opportunity for homeowners seeking a move-in-ready property in one of Central Florida's most sought-after communities. Step inside to discover a bright and inviting floor plan designed for both everyday living and entertaining. The well-appointed kitchen features stainless steel appliances, granite countertops, and ample cabinetry, creating a functional and stylish space for preparing meals and gathering with family and friends. The home's well-maintained interior reflects pride of ownership throughout, offering a warm and welcoming atmosphere from the moment you arrive. The spacious living areas and comfortable bedrooms provide plenty of room to relax and unwind, while the thoughtful layout maximizes both comfort and convenience. This home's upgrades include : Roof replaced in 2021, Replumbed in 2020,, Water heater replaced in 2018, AC will be replaced prior to closing, Updated kitchen, and Hardwood flooring throughout — no carpet! Whether you're hosting guests, working from home, or simply enjoying a quiet evening in, this home is designed to fit a variety of lifestyles. Located in the heart of Winter Park, you'll enjoy easy access to the area's renowned dining, shopping, parks, and cultural attractions. Spend weekends exploring the boutiques and cafés along Park Avenue, enjoying a scenic boat tour through Winter Park's picturesque lakes, or visiting nearby gardens, museums, and recreational trails. With convenient access to Downtown Orlando, major employers, top-rated schools, and world-famous attractions, this location offers the perfect balance of suburban charm and urban convenience. Don't miss this opportunity to own a well-cared-for home in one of Central Florida's premier neighborhoods. Schedule your private showing today and discover everything this wonderful Winter Park property has to offer!

3641 Hawthorne Lane, Winter Park

$450,000

4 Beds ⋅ 3 Baths ⋅ Country Lane SubDv. ⋅ 32792 Zip Code

Discover the potential of this spacious 4-bedroom, 2.5-bath home located at 1564 Lawndale Cir in desirable Winter Park. Featuring a comfortable floor plan with generous living space, this home offers flexibility for everyday living, entertaining, working from home, or hosting guests. The bedroom layout provides privacy and functionality, while the location offers convenient access to shopping, dining, parks, schools, major roadways, and nearby Orlando destinations. With its size, layout, and prime Winter Park location, this property is a great opportunity for buyers looking to personalize a home and create lasting value. Don’t miss your chance to schedule a private showing.

1564 Lawndale Circle, Winter Park

$449,000

32789 Zip Code

Some opportunities don't announce themselves. They show up quietly in Winter Park's most sought-after zip code, waiting for someone who knows exactly what to do with them. This vacant lot inside Waterbridge sits in the 32789 zip code, a rare chance to build the home you've always had in mind, in a neighborhood that has already decided who it is. Waterbridge is a tight-knit, tree-lined enclave where the homes are custom and the neighbors stay. Lots like this do not come available often. The address puts you minutes from Park Avenue's galleries and weekend farmers market, AdventHealth Winter Park, and the employers and services that make this corridor one of Winter Park's most connected. The schools zoned here, Glenridge Middle and Winter Park High, are among the most respected in Orange County and part of why buyers seek out this zip code specifically. Build the primary suite you've never been able to find. Design the kitchen around how you actually cook. Choose the ceiling heights, the materials, the layout. Every decision a resale home will never let you make is yours to make here. A lot in Waterbridge represents something that rarely surfaces: the convergence of a blank canvas and a proven address.

Jessica Court, Winter Park

$379,000

3 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 06 2nd Rep SubDv. ⋅ 32792 Zip Code

SELLER FINANCING. Stunning 3-bedroom, 2-bath remodeled home with no HOA, ideally located on the border of Winter Park and Orlando. This move-in-ready property features a new roof installed in July 2025, an updated kitchen with beautiful granite countertops and brand-new appliances. Enjoy the perfect combination of comfort, style, and convenience with easy access to shopping, dining, schools, and major roadways. Don't miss this one! Schedule your private showing right away!

1605 Puritan Avenue, Winter Park

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