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$350,000
3 Beds ⋅ 2 Baths ⋅ Woodcrest Unit 01 SubDv. ⋅ 32792 Zip Code
Discover the perfect blend of comfort and convenience in this beautifully remodeled 3-bedroom, 2-bath home located in Winter Park’s desirable Woodcrest neighborhood. Featuring quartz countertops, stainless steel appliances, and thoughtful modern updates throughout! Newer roof (2018), plumbing (2021), and windows (2019)! This home is truly move-in ready. Enjoy relaxing on the covered back patio, hosting with ease in the open living spaces, and being just minutes from top-rated schools, parks, dining, and everything Winter Park has!

5110 N Woodcrest Drive, Winter Park
$85,000
2 Beds ⋅ 2 Baths ⋅ Winter Park Woods Condo SubDv. ⋅ 32792 Zip Code
2 Bedrooms and 1.5 upgraded condo unit in Winter Park Woods

110 Scottsdale Square Unit 110, Winter Park
$495,000
4 Beds ⋅ 2 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. ?? Mid-Century Modern Gem in Sought-After Winter Park Pines Lovingly maintained and move-in ready, this Mid-Century Modern 4-bedroom, 2-bath home (just under 1,700 sq. ft.) offers light-filled living and timeless style in the heart of Winter Park Pines. Set beneath graceful mature oaks, the landscaped front yard provides a welcoming canopy. Step through the front door into a travertine-floored foyer overlooking the open living and dining areas — ideal for entertaining or relaxing in natural light. The modern kitchen features: Painted wood cabinetry, Granite countertops and stainless steel appliances (range, refrigerator, microwave, dishwasher, and wine fridge), Peninsula bar with prep sink for easy meal prep, French doors opening to the backyard. All four bedrooms feature ceiling fans and brand new textured carpet. The primary suite includes two closets and an updated marble-tiled bath. Enjoy the fully fenced backyard with garden space and irrigation system—perfect for pets, play, or quiet evenings under the trees. There’s also extra storage off the courtyard-entry carport, plus a pantry and coat closet for everyday convenience. Insulated, upgraded windows, Upgraded electrical service, Fresh paint throughout, New carpet and fixtures. The prime location is located just steps from Winter Park Pines Golf Course and minutes from Park Avenue, Winter Park Village, and Baldwin Park Town Center. Convenient to shopping, dining, and top-rated schools.

422 S Ranger Boulevard, Winter Park
$340,000
3 Beds ⋅ 2 Baths ⋅ Glenmoor SubDv. ⋅ 32792 Zip Code
This is the Opportunity of Winter Park 2025 !! Possibilty for 4th bedroom or Office! Nov 26 Price improvement! make the deal ! All the Big items are Fresh and Ready New Shingles on the Roof in 2018, HVAC System is from 2017, Hot Water Heater is 2019, Interior Walls Ceilings and Trim were just Completely repainted,Stainless Steel Appliance package. Bathrooms have been updated as well. All New Hinges and Door Knobs with Nichol Finish, New LED Lights for max efficiency and modern brighness. Ceiling Fans in most rooms. Side Entry Garage on 1/3 Acre Lot with extra Parking pad/driveway. Boat/Trailer storage behind fence at end of 2nd Driveway. Great Floor Plan with tile floors through out. Located in the most desired schools and access to all the best Orange County has to offer.Plenty of opportunity for some sweat equity as well.Chance to Move in before the Holidays and just intime to file for Homestead in 2026 See it today!! Now is the Time to make your Best deal

7728 Glenmoor Lane, Winter Park
$505,000
4 Beds ⋅ 2 Baths ⋅ Tamarak SubDv. ⋅ 32792 Zip Code
Welcome to this charming 4 bedroom, 2 bath home located in the desirable Charter Oaks subdivision of Winter Park. The centrally located kitchen features stainless steel appliances, granite countertops, and a breakfast bar that seamlessly connects to the family room. Enjoy cozy evenings by the wood burning fireplace or host gatherings in the separate dining room and spacious living room. Step outside to your own private retreat with a fully fenced yard and a covered screened patio with pool, perfect for year round entertaining and relaxation. This home also includes fully owned solar panels offering energy efficiency and reduced utility costs. Nestled in a quiet tree lined neighborhood with no HOA, this home provides the perfect balance of peace and convenience. You will be just minutes from Park Avenue, boutique shopping, world class dining, and the scenic Winter Park Chain of Lakes. Families will appreciate access to top rated schools, nearby parks, and recreational opportunities. With easy access to major highways and a short drive to downtown Orlando, this location simply cannot be beat.

1691 Bomi Circle, Winter Park
$500,000
3 Beds ⋅ 2 Baths ⋅ Brookshire Heights 1st Add SubDv. ⋅ 32792 Zip Code
Gorgeous move in ready or spacious corner lot to build your Dream Home, fully updated 3 bedroom, 2 full bath , corner lot home in a coveted Winter Park neighborhood! The interior is completely renovated throughout, including kitchen with stone countertops, two year old appliances, all new bathrooms with shower glass doors, flooring with plank tiles, two year old A/C unit and air handler, new lighting, roof 5 yrs old. Inside laundry room now included under air also provides newer washer and dryer. Interior and exterior freshly painted, new wooden fence, new spacious wooden back pergola, enlarged paver area in the back, new landscape, new shed, new irrigation system with well, new RV/ trailer garage with gravel, professionally installed garage epoxy, custom made closets, updated electrical breaker box, additional 220 electrical outlet for electric cars and more! This is a great location that is just blocks from Brookshire Well served by a variety of Top-Rated Orange County Schools, the neighborhood is only .5 miles to Brookshire Elementary, 1.8 miles to Glenridge Middle School, .3 miles to Winter Park High School and 3.2 miles to Rollins College. This Winter Park Community is surrounded by great outdoor activities including the Cady Way Trail, 2 miles from Baldwin Park, .7 miles from the Showalter Field and .8 miles from Winter Pines Golf Club. A shopping and dining gem, you will also be only 3.3 miles from Park Ave, 6.2 miles from Downtown Orlando and 1.4 miles away from the Winter Park Hospital. Call today before this one is gone! Decorations attached to the walls are not for sell.

2412 Middleton Avenue, Winter Park
$223,000
3 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 05 SubDv. ⋅ 32792 Zip Code
Sold data only.

1378 Chilean Lane, Winter Park
$450,000
3 Beds ⋅ 2 Baths ⋅ Kenilworth Shores Sec 01 SubDv. ⋅ 32792 Zip Code
Value is in the land/lot with potential for a renovation/remodel. Excellent opportunity to own a block home in Winter Park with a preexisting pool and some valuable upgrades including tankless water heater, newer washer/dryer, and newer HVAC.

443 S Lakemont Avenue, Winter Park
$110,000
3 Beds ⋅ 2 Baths ⋅ Winter Park Woods Condo SubDv. ⋅ 32792 Zip Code
For Sale Purpose Only

106 Scottsdale Square Unit 106, Winter Park
$425,000
3 Beds ⋅ 2 Baths ⋅ Wrenwood Unit 3 3rd Add SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. Beautifully Renovated 3-Bed, 2-Bath Home in Winter Park!!! Experience modern living at its finest in this fully renovated 3-bedroom, 2-bathroom home located in the heart of Winter Park. Recently updated with a new roof (installed within the last six months), HVAC systembupdated within the last few years, and upgraded plumbing, this residence offers both peace of mind and contemporary style. The interior features a luxurious open-concept design with premium finishes, designer fixtures, and a fully remodeled kitchen complete with custom cabinetry and stainless steel appliances. The spacious primary suite includes a beautifully updated ensuite bathroom. Perfectly situated near A-rated schools, premier shopping, dining, and entertainment, this move-in-ready home delivers the ideal blend of elegance, comfort, and convenience in one of Central Florida’s most desirable locations.

5201 Ardmore Drive, Winter Park
$528,000
4 Beds ⋅ 2 Baths ⋅ Wrenwood Heights SubDv. ⋅ 32792 Zip Code
Experience the perfect blend of modern luxury and timeless charm in this newly renovated 4-bedroom, 2-bath Winter Park retreat. Thoughtfully designed with an open-concept layout, this home features sun-filled living spaces, a beautifully appointed kitchen with premium finishes, and a generous great room ideal for entertaining. A versatile spacious sunroom bridges indoor and outdoor living, offering the perfect spot for a home office, gym, or relaxation lounge as it opens to the backyard oasis. Outside, lush landscaping frames a large inground pool and expansive patio—an idyllic setting for gatherings or peaceful retreat. Just minutes from Park Avenue, top-rated schools, and Winter Park’s vibrant dining and shopping, this home captures the essence of Central Florida living at its finest. New roof installed 09/2025, Pool resurfaced 09/2025.

4991 Tangerine Avenue, Winter Park
$435,500
3 Beds ⋅ 2 Baths ⋅ Garden Lake Estates Unit 1 SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. Welcome to this stunning Winter Park pool home, offering 3 bedrooms and 2 bathrooms across 1,668 square feet of thoughtfully designed living space. Upon entering, you are greeted by a spacious, open living area where the living and dining rooms flow seamlessly together, creating a perfect space for entertaining or relaxing with family. The kitchen features stainless steel appliances, abundant cabinetry, and generous counter space, complemented by a breakfast nook that opens to the family room. A sliding glass door leads from the family room to the enclosed Florida room, providing a bright, versatile space to enjoy year-round. The split bedroom floorplan ensures privacy, with the primary suite boasting an en suite bathroom complete with a walk-in shower. Step outside to a beautifully landscaped backyard with an in-ground pool and a pergola, ideal for outdoor gatherings or quiet afternoons. The enclosed Florida room with A/C overlooks the yard, making it perfect for indoor-outdoor living. Sitting on over a quarter acre, this home offers ample space for relaxation and recreation. Recent upgrades include fresh paint, new carpet, a brand-new hot water heater, and a new kitchen sink and faucet. Conveniently located near grocery stores, restaurants, and with easy access to highways, UCF, downtown Orlando, and all the city has to offer, this home combines comfort, style, and location in one exceptional package. Don’t miss the opportunity to make this Winter Park gem your new home. Mortgage savings may be available for buyers of this listing.

1630 Gladiolas Drive, Winter Park
$300,000
3 Beds ⋅ 2 Baths ⋅ Slovak Village SubDv. ⋅ 32792 Zip Code
A MUST SEE! Beautifully remodeled 3 bedroom 2 bath home. Third bedroom has its own separate entrance as well. Large foyer and living room. Kitchen has beautiful 40 inch cabinets and granite counter tops. Septic system was just replaced in September. Close to everything.

121 Stefanik Road, Winter Park
$85,000
2 Beds ⋅ 2 Baths ⋅ Winter Park Woods Condo SubDv. ⋅ 32792 Zip Code
Entry for Sale Data Only

346 Scottsdale Square Unit 346, Winter Park
$357,500
3 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 8 SubDv. ⋅ 32792 Zip Code
LOCATION LOCATION LOCATION!! This 3 bedroom 2 bath home features an open floor plan with loads of natural light. Generous sized Kitchen and Living Areas. Large fenced backyard. New paint inside and out, along with new ceiling fans and light fixtures. Roof is 2018, Replumbed 2016 and HVAC 2019. This home is a must see!!!

2065 Cocos Lane, Winter Park
$458,000
4 Beds ⋅ 3 Baths ⋅ Bel-Aire Pines, Unit Two SubDv. ⋅ 32792 Zip Code
Virtually Staged. Stunning Two-Floor Home in Coveted Winter Park School District Immaculately maintained and truly move-in ready, this unique two-story residence features distinct living quarters with private entrances to both levels. The main floor offers a spacious split-bedroom layout with three bedrooms and two full baths, including a primary suite with an en-suite bathroom and generous walk-in closet. The fully equipped kitchen boasts newer appliances and opens to a bright living area. The expansive 800 sq. ft. upper level functions as a self-contained living unit, ideal for multi-generational arrangements, home offices, or rental income potential. This versatile space includes one bedroom, a full bathroom, a private balcony, and a full open-concept living and dining area complete with a full-size refrigerator and stove. Located in the highly rated Winter Park School District, this home offers the perfect blend of top-tier education and Central Florida lifestyle. Residents enjoy easy access to world-class entertainment, situated just 26 miles (approx. 35 minutes) from Walt Disney World. Additional features include a large two-car garage with washer/dryer hookups, ample driveway parking, fresh interior paint, and a brand-new roof with a transferrable warranty. All major systems are well-maintained and in excellent working condition.

3312 Heartwood Avenue, Winter Park
$365,000
4 Beds ⋅ 2 Baths ⋅ Eastbrook Sub SubDv. ⋅ 32792 Zip Code
Welcome Home to Eastbrook in Winter Park! This beautifully maintained 4-bedroom, 2-bath home offers the perfect blend of comfort, charm, and modern updates — all nestled on an OVERSIZED CORNER LOT in the desirable Eastbrook community with NO HOA and NO CDD. Step inside to find 1,530 sq ft of thoughtfully designed living space, freshly painted in 2025 to give every room a bright, inviting feel. The renovated primary bathroom shower (2025) adds a touch of luxury, while the repiped plumbing (2024) comes with a transferable 30-year warranty for peace of mind. Enjoy outdoor living at its best with a brand-new fence and paved driveway (2023). Major updates have already been taken care of, including a new HVAC (2021), new water heater (2023), and a 9-year-old roof, ensuring this home is move-in ready and worry-free. You’ll love the convenient location — just 10 minutes to Downtown Winter Park and 15 minutes to Baldwin Park, putting shopping, dining, and local charm right at your fingertips. Located in the heart of Winter Park, Eastbrook is known for its welcoming vibe, tree-lined streets, and proximity to top-rated schools, parks, and more. Whether you're a first-time buyer or simply ready for your next chapter, this home has everything you’ve been looking for — style, updates, and location all in one!

1083 Eastbrook Boulevard, Winter Park
$699,450
4 Beds ⋅ 2 Baths ⋅ Greenview At Winter Pines SubDv. ⋅ 32792 Zip Code
**Multiple offers received*** Please submit highest and best by 10/20/2025 at 4:00 pm This beautifully maintained golf course home offers effortless living in an established Winter Park neighborhood. As you drive along the charming tree-lined streets, the home greets you with impeccable landscaping and timeless curb appeal. Step inside the foyer and discover a bright, open floor plan that seamlessly connects the dining area, kitchen, and living room. Soft natural finishes create a breezy, relaxed feel, while the cozy fireplace anchors the living space, which is perfect for gathering with loved ones. The kitchen is both stylish and functional, featuring stainless steel appliances, stone countertops, a farmhouse sink, and refinished cabinetry. The stylish island provides casual dine-in seating, and the custom pantry and laundry room offer exceptional storage, plus a convenient folding counter and hanging space. Your private primary suite is tucked away to the left of the kitchen, offering serene views and sliding doors that open to the screened lanai overlooking lush, mature landscaping. The walk-in closet provides generous storage, and the updated ensuite bath includes a walk-in shower with both handheld and fixed showerheads. A split floor plan offers three additional bedrooms and an updated guest bath with a tub and glass enclosure perfect for guests. Relax on the screened lanai and enjoy peaceful golf course views and privacy. The brand-new roof provides peace of mind, and the widened paver driveway offers both style and convenience. The garage is equipped with a workbench and built-in shelving for all your storage needs, plus an additional shed and fenced side yard create more outdoor space to enjoy. Located within the Winter Park school district, this home offers the perfect blend of privacy and convenience — just 8 minutes from Lake Baldwin Park, 10 minutes to Corrine Drive’s shopping and dining, 12 minutes to Park Avenue, and 20 minutes to Downtown Orlando.

1346 Golfside Drive, Winter Park
$470,000
3 Beds ⋅ 2 Baths ⋅ Garden Lake Estates Unit 2 SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. **2025 ROOF** Pride of ownership shines throughout this well maintained 3 Bedroom + OFFICE home, ideally situated on a spacious corner lot in a quiet, neighborhood with NO HOA. With 2,031 square feet of living area including the enclosed porch, this property offers exceptional flexibility and room to grow. Step inside and immediately feel at home in the bright, open layout featuring soaring vaulted ceilings, neutral tones, and wood look luxury vinyl plank flooring that flows seamlessly throughout the home. The living room welcomes you with abundant natural light and a sense of openness, leading into a dedicated formal dining area that overlooks both the pool and main living areas, perfect for family gatherings or entertaining friends. The updated kitchen has been tastefully renovated with custom cabinetry, quartz countertops, and stainless steel appliances, creating a functional space that opens directly to the family room. Whether you’re preparing meals, watching a movie, or keeping an eye on the pool, this layout ensures you’re always part of the action. From the family room, sliding glass doors open to the expansive enclosed porch, a versatile bonus area surrounded by windows on two sides that let in plenty of light and gentle Florida breezes. This space offers countless possibilities — use it as a game room, second living room, home gym, or entertaining space overlooking the pool. Outside, enjoy year round relaxation in your screened pool and patio area, perfect for cooling off on warm afternoons or hosting weekend barbecues. The vinyl fence adds privacy and a clean, low maintenance look to the backyard. The split bedroom floor plan ensures comfort and privacy for all. The primary suite features a newly renovated bathroom with stylish finishes, while the secondary bedrooms are generous in size and share a well appointed guest bath. The dedicated office provides a quiet retreat for working from home, studying, or hobbies. Additional highlights include an oversized side-entry garage with built-in storage shelving and a workbench, ideal for projects or extra storage space. Major updates have already been taken care of for peace of mind — including a new roof (2025) and new pool screens (2025). This is a truly special home that combines modern updates, flexible living spaces, and a private outdoor retreat all in a desirable location close to shopping, dining, and top-rated schools. Schedule your private tour today!

1931 Aster Drive, Winter Park
$627,000
4 Beds ⋅ 3 Baths ⋅ Kenilworth Shores Sec 03 SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. Income-Producing Opportunity! Welcome to this versatile Winter Park POOL HOME! At present, this property is split into two separate living quarters with the main house offering 3 bedrooms & 2 bathrooms and the adjoining guest suite offering 1 bedroom & 1 bathroom. Each living quarter has its own kitchen, laundry, climate control & outdoor living space. Rent out the guest suite, share an address with an independent someone, or use the adjoining door to make one fluid space. There are tile floors throughout all areas and a 2-car carport with long driveway in front of both front doors. The heated, chlorine pool is nestled inside a fenced backyard and can be accessed by both living quarters; however, there is an outdoor retractable privacy divider to separate the outdoor spaces if so wished. The property holds 2 sheds; the larger, cottage-style shed is fully powered and insulated, and has a shelving unit on a swing hinge to create a bar at the shed’s double doors for outdoor entertaining. The propane firepit stays and is ready for your housewarming party! Notable updates include 2019 ROOF, 2022 main house A/C, 2024 pool pump & filter, 2025 pool heater. This home has been repiped, rewired, and has updated windows. A breaker box expansion was completed to provide power to the pool heater & cottage shed. The guest suite has a built-in mini split a/c, dehumidifier, water filtration under the kitchen sink & a murphy bed plus armoire storage which will stay. This corner lot property proudly stands a quarter mile to Ward Park and slightly over a mile to Lake Baldwin Park for a sample of the city’s plentiful recreation opportunities. Come explore this opportunity before it’s gone!

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

2152 Conifer Avenue, Winter Park
$235,000
32792 Zip Code
This land is located in a PRIME area for development. Drive down the street (and Wilde Ave) and check out all the amazing new homes being build in this neighborhood. No HOA. There was once a home on the property, had water and septic. Due diligence up to buyer. You won't find another opportunity like this in Winter Park. .73 acres in a quiet area to build your perfect dream home! **ALL PREVIOUS LISTINGS WERE FRADULENT* Agent is related to owners of property. Someone was impersonating actual seller and contacting unsuspecting realtors in attempt to scam buyers.

7449 Restful Street, Winter Park
$500,000
3 Beds ⋅ 2 Baths ⋅ Brookshire Heights SubDv. ⋅ 32792 Zip Code
This is a stunning, fully renovated 3-bedroom, 2-bathroom home situated in the heart of Winter Park, offering a move-in ready experience with major system updates for peace of mind, including a New Roof (End of 2023), a Tankless Water Heater (2024), and a new A/C System (2020). The interior features an expertly redesigned, open-concept floor plan perfect for entertaining, with the dining room overlooking the living room, a chef's kitchen boasting updated cabinetry, countertops, and a breakfast nook, and a private Master Suite with a walk-in closet and a master bath with double sinks and a walk-in shower. The unbeatable location places you just minutes from Park Avenue, Baldwin Park, AdventHealth's state-of-the-art hospital, and the Winter Park Wellness Center, and is zoned for top-rated schools, while offering an active lifestyle with a short stroll to the Cady Way Trail, Cady Way Pool & Pickleball Courts, and Showalter Fields. Seize a rare opportunity to invest or build in one of Winter Park's most rapidly appreciating neighborhoods. The true value of this offering is in the land, perfectly positioned for a high-end renovation or a brand-new luxury custom home, as this street is undergoing a dramatic transformation, with recent new construction and luxury renovations selling consistently well over the million-dollar mark—this is your chance to secure a stake in this proven growth area! Schedule a private showing today to experience this unparalleled Winter Park opportunity!

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

1317 Medinah Court, Winter Park
$660,000
4 Beds ⋅ 2 Baths ⋅ Williamsburg SubDv. ⋅ 32792 Zip Code
Welcome to this well-maintained Winter Park home, proudly cared for by its original owner. With a BRAND NEW ROOF and BRAND NEW AC system, this property combines peace of mind with long-term value. Set on a spacious quarter-acre lot with NO HOA, it offers flexibility, privacy, and convenience in one of Central Florida’s most desirable locations. This home features a durable roof with a 10-year transferable warranty, engineered to withstand winds of up to 130 mph for lasting protection and peace of mind. Step inside through the front entry into a light-filled formal living room, where large windows set a warm and welcoming tone. Just to the right, the formal dining room provides the perfect space for family gatherings or entertaining. Flowing naturally into the main family room, you’ll find a cozy fireplace that anchors the space and creates an inviting setting for everyday living. The kitchen is designed for function with all appliances included, ample counter space, and a thoughtful connection to the laundry room, which features generous storage and everyday convenience. Off the family room, the Florida room is bright and versatile—ideal for a home office, reading nook, or playroom. One of the standout features is the expansive 483 sq. ft. bonus room, offering endless possibilities as a game room, studio, or additional living space to suit your lifestyle. Outdoors, a screened-in porch overlooks the fenced backyard, providing a comfortable spot to relax, garden, or host gatherings. An included shed adds extra storage for tools and equipment. Each bedroom is well-sized, offering comfort and practicality, with bathrooms that have been cared for and maintained with attention to detail. The thoughtful layout balances privacy and community spaces, making it both functional and inviting. Location is key, and this home delivers. Just a few minutes’ walk takes you to the scenic Cady Way Trail, Winter Park Pines Golf Course, and Winter Park High School. Nearby parks, shopping, dining, and top-rated schools add to the convenience, while downtown Winter Park, Orlando attractions, and major highways are only a short drive away. Perfect for buyers seeking a primary residence, an Orlando relocation home, or a smart Central Florida real estate investment, this property is a rare find. With only one owner since construction and NEW major systems in place, this Winter Park gem is ready for its next chapter. Contact us today for a private tour or more details on this exceptional opportunity.

2421 Summerfield Road, Winter Park
$335,000
3 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 09 SubDv. ⋅ 32792 Zip Code
Are you looking for a great house set on an incredible piece of land? Well look no further because this house sits in the subdivision Eastbrook. This split floorplan has a large open kitchen with a large area for eating breakfast and a separate dining room. The master boasts of a walk in closet and an remodeled master bath. While this house still has a lot of it's original charm, it has been loving maintained and you would make home owner number 3! The main bathroom has an a completely remodeled shower and easily accessible for any age! The size of the lot of yard has endless potential whether you want to add a pool, playground or even an additional room it is up to you! Oh and the AC unit is from 2020 and the hot water heater is new too! This property is as is/where is.

3525 Baxter Drive, Winter Park
$199,000
2 Beds ⋅ 2 Baths ⋅ Whisperwood Condo SubDv. ⋅ 32792 Zip Code
One of the lowest-priced homes in Winter Park with nearly 1,400 square feet, a private carport, screened balcony, community pool, and easy access to UCF, Full Sail, Rollins, Valencia East, Orlando International Airport, and downtown Orlando! The monthly HOA covers many exterior maintenance items so you can enjoy low-maintenance living.This 2 bedroom, 1.5 bathroom condo features a townhome style layout with spacious living areas. Recent enhancements include the removal of dated laminate to reveal ceramic tile flooring throughout the main level, installation of stylish luxury vinyl plank on the upper level, new carpeting on the staircase and landing, and a full interior repaint. In addition, the sliding glass doors were professionally serviced, including roller replacement, track repairs, and installation of new locks to ensure smooth, secure operation. Deluxe vinyl fencing was installed throughout the community by the HOA replacing the older wooden fencing. The fencing was replaced with the vinyl after the listing photos were taken, please view the video to see the replacement vinyl fencing. Enjoy convenient features including an in-unit washer and dryer combo, storage under the stairs, and a large carport with an attached storage shed. The spacious primary bedroom opens to a large screened-in balcony. Whether you’re a first-time home buyer, student, investor, or looking to make your move into Winter Park, this home offers affordability, convenience, and plenty of potential!

7471 Canford Court Unit 19, Winter Park
$345,000
3 Beds ⋅ 2 Baths ⋅ Winter Park Estates SubDv. ⋅ 32792 Zip Code
Welcome to your slice of Winter Park paradise! Nestled in the sought-after neighborhood of Winter Park Estates, this 3-bedroom, 2-bath home sits on a quarter-acre lot surrounded by mature landscaping and Florida sunshine. Inside, natural light pours through the windows, highlighting spacious living areas and an inviting Florida room that overlooks the sparkling pool—perfect for relaxing or entertaining. The two-car garage includes a workbench area, ideal for projects or extra storage. Whether you’re dreaming of updating, expanding, or simply enjoying the Florida lifestyle as-is, this home offers a blank canvas for whatever your heart desires. Zoned for top-rated schools and located just minutes from the best of Winter Park dining, shopping, and parks—this is an opportunity you won’t want to miss.

731 Bongart Road, Winter Park
$899,000
4 Beds ⋅ 3 Baths ⋅ Greenview At Winter Pines SubDv. ⋅ 32792 Zip Code
Discover elevated living in this stunning 4 bedroom, 2.5 bathroom pool home, perfectly situated overlooking a tranquil pond and Winter Park 18 hole golf course. Surrounded by a lush tropical backyard oasis, this residence blends modern sophistication with effortless comfort, creating a serene retreat that’s ideal for that perfect start to the morning with a cup of coffee or a relaxing wind down at sunset with a glass of wine. Inside, vaulted wood-trimmed ceilings and a wood-burning fireplace set a warm, inviting tone across 2,455 sq. ft. of thoughtfully designed space. The kitchen features contemporary cabinetry paired with quartz and butcher block wood countertops and a designer tile backsplash. Stainless steel appliances, including a beverage refrigerator, add a professional touch, while a built-in banquette provides seating for six—perfect for entertaining and everyday living. The primary suite offers wood floors, a walk-in closet, and a spa-like bath with dual floating vanity, soaking tub, and seamless glass shower. Enjoy outdoor living at its finest with pergola-covered sitting areas, outdoor shower, fire pit, and sparkling pool. Situated on a private tree-lined cul-de-sac, this home is located in a prime location just minutes from Cady Way Trail, Cady Way pool & courts, Winter Park Pines Golf Course, Crosby Center for Health and Wellbeing, Ward Park, Showalter Athletic Complex, Advent Health Winter Park Hospital and less than 10 minutes to Historic Park Avenue fine dining and shopping. Don’t miss your chance to own this rare Winter Park gem—schedule your showing today! ROOF - 2016 HVAC - 2023(2) PLUMBING - 2020 ELECTRICAL - 2021 WATER HEATER - 2020

1648 Cypress Point Lane, Winter Park
$398,000
3 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 05 SubDv. ⋅ 32792 Zip Code
Welcome to 3529 Australian Circle, a beautifully updated 3-bedroom, 2-bathroom POOL home located in the desirable EASTBROOK subdivision of WINTER PARK. Designed for comfort and everyday living, this home blends modern updates with timeless character. Step inside to find an open floor plan enhanced by high ceilings, WOOD-LOOK TILE flooring in the main living areas, and BAMBOO flooring in all three bedrooms. The REMODELED kitchen (2022) serves as the heart of the home, featuring BUTCHER BLOCK countertops, timeless cabinetry with soft-close drawers, a large breakfast bar, and a new mini-split system for improved air circulation. The kitchen flows seamlessly into the dining area and great room, creating a welcoming space for both entertaining and everyday moments. Adding warmth and character, the shiplap ceilings in the kitchen and great room tie the design together. The interior was freshly PAINTED in 2023, while crown molding (2024) adds a refined finishing touch. Step through the French doors into your private backyard oasis—complete with a covered porch featuring a tongue-and-groove ceiling, a fully FENCED yard, and a large open-air pool accented with flagstone. The 2023 irrigation system keeps the beautiful exotic palms thriving, and the system draws from a backyard aquifer, helping to save on water bills. The primary suite offers a peaceful retreat with an en-suite bathroom, granite countertop, and a walk-in shower with travertine tile. Two additional bedrooms share a stylish second bathroom. Practical updates provide peace of mind, including a roof (2018), A/C (2018), electrical panel (2021), water heater (2022), and double-paned windows. The SIDE-ENTRY one-car GARAGE adds convenience and curb appeal. Take advantage of an Exclusive Offer: 1% of loan amount toward closing costs or rate buy-down. Inquire today! Located on a quiet street with no HOA restrictions, this home is zoned for top-rated Seminole County schools and just minutes from Park Avenue’s shopping and dining, Rollins College, Winter Park Hospital, and nearby museums. With its thoughtful updates, inviting layout, and unbeatable location, this home offers an exceptional opportunity to enjoy the Winter Park lifestyle. Schedule your private tour today!

3529 Australian Circle, Winter Park