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$450,000
3 Beds 2 Baths Winter Park Estates SubDv. 32792 Zip Code
Under contract but will accept back-up offers. Beautiful Pool Home in Desirable Winter Park Estates. Seller is Motivated. Welcome to this charming and thoughtfully updated pool home in the highly sought-after Winter Park Estates subdivision—zoned for top-rated schools, including Winter Park High School. This mid-century gem blends modern comfort with timeless style, located in one of Central Florida’s most beloved neighborhoods. Property Highlights: Sparkling saltwater in-ground pool with newer pavers and decorative lighting Three new awnings provide shade and style for relaxing poolside Covered rear porch with mid-century style masonry garden and succulent plants Summer kitchen—perfect for outdoor entertaining Newer vinyl fencing surrounds a private, spacious backyard Backyard shed for tool storage or a workshop space Modern kitchen with built-in lighting, hidden compartments, and custom cabinetry Updated bathrooms with stylish, contemporary finishes Wood-burning masonry fireplace for cozy ambiance Blinds-in-glass French doors provide elegant access to outdoor living spaces Interior laundry room for added convenience This home offers the best of both worlds: classic mid-century character with today's sought-after updates. Whether you’re hosting guests by the pool or enjoying a peaceful evening at home, this residence is built for comfort and enjoyment. All measurements are approximate and should be verified by the buyer and their agent.

2648 Amsden Road, Winter Park

$1,206,400
4 Beds 4 Baths Bear Gully Pointe SubDv. 32792 Zip Code
Welcome to 4048 Gilder Rose Pl, an impressive four-bedroom, three and a half bathroom residence spanning over 3,300 square feet, located in Winter Park at Bear Gully Pointe, a gated community featuring a spring fed 137 acre lake. This beautifully updated home perfectly balances modern style with practical living, offering an inviting retreat for those seeking both comfort, sophistication and completely turn key. After entering the gated community and arriving at this show stopping residence, your guest will either be able to park in your circular drive way up front or your extra long side entrance that leads to your 3 car garage with epoxy floors and built in storage. The garage also includes a Tesla EV charger and tankless hot water heater. Once parking up front you'll step through the double front doors into a spacious, open-concept layout filled with natural light and accented by luxury vinyl plank flooring. Upon entering your grand foyer you will walk past the office with custom built ins on your left and your formal dining room on your right. Once you reach the hallway on your left your guests will be able to use the half bathroom, the hallway separates the half bathroom from the beautiful kitchen. The kitchen features custom cabinetry, quartz countertops, built-in stainless steel appliances, a gas cook top for the chef of the house and a central island that includes a wine fridge, ideal for both daily meals and entertaining guests. You will be able to enjoy meals at your eat in kitchen or the breakfast nook that flows into the living room. The primary suite is a true sanctuary, with a seating area to enjoy your morning coffee in front of the gas fireplace or outside on your private patio the Primary suite is complete with two generous walk-in closets and a luxurious en-suite bath, featuring dual vanities, a frameless glass shower, a soaking tub and plenty of natural light. Each additional bedroom is thoughtfully designed, providing comfort and privacy for family members or guests. There is enough space for families big and small, 4 bedrooms plus an office/bonus room. Walk through your brand new Pella Doors (not pictured, that's how new they are) to your own personal oasis, boasting a sparkling pool with a custom flagstone patio provides the perfect space for outdoor gatherings, all framed by lush, mature landscaping and a conservation view. Whether you're soaking up the Florida sun or hosting weekend barbecues with your summer kitchen that features built in speakers, a gas grill, a sink and plenty of chilled space for your beverages of choice, this space is designed for making memories. In the evening you'll want to gather around your built in wood burning fireplace. Situated in Winter Park, this home offers easy access to top-rated schools, boutique shopping, and award-winning dining, making it the perfect choice for those seeking the best of Central Florida living. This neighborhood is highly desirable for families looking to be near Tuskawilla and easy access to Trinity Prep. Don’t miss this opportunity to make this exceptional Winter Park residence your own – <iframe src="https://my.matterport.com/show/?m=JgcRhZG1izN" frameborder="0" width="853" height="480" allowfullscreen allow="xr-spatial-tracking"></iframe>

4048 Gilder Rose Place, Winter Park

$1,100,000
4 Beds 4 Baths Lake Florence Preserve SubDv. 32792 Zip Code
Virtually Staged. Incredible Value!!! Major price reduction! Private Lakefront Living! Move-in Ready! Wake up to water views, quiet mornings and the kind of lifestyle that rarely becomes available in the Winter Park/Howell Branch area. Set along the shores of a private ski lake- Lake Florence, this single-level lakefront residence offers a serene retreat within an intimate gated enclave of just 28 homes. A setting that feels private and peaceful that is increasingly hard to find. Designed for both everyday comfort and effortless entertaining, the thoughtfully planned 4-bedroom, 3.5-bath layout includes a dedicated office, formal dining room and a desirable three-way split floor plan that provides flexibility and privacy for today’s lifestyle. At the heart of the home, the gourmet kitchen blends beauty and function with quartz countertops, a substantial center island, natural gas cooktop, 42" solid wood cabinetry, walk-in pantry, and a generous butler’s pantry—perfect for hosting or simply enjoying the flow of daily living. Rich wood flooring carries throughout the home connecting the kitchen seamlessly to the light-filled family room and casual dinette area. The primary suite is a true lakefront sanctuary featuring peaceful water views, two walk-in closets and a spa-inspired bath with dual sinks and an oversized shower with dual shower heads. Many upgrades are to be found through out this home such as an extra oversized storage closet, crown molding, custom mud room off of the laundry room, high ceilings, tray accents and abundant natural light to enhance the home’s relaxed, refined feel. Outdoors, the property transforms into a private lakefront escape. Enjoy sweeping water views, a sparkling pool and spa, custom rock waterfall, screened-in lanai and a fully fenced yard framed by tall privacy hedges and mature trees—ideal for quiet evenings or weekend gatherings. Direct lake frontage and access to a nearby community dock complete the lifestyle experience. A three-car garage with a separate AC wall unit offers added versatility—perfect for a workshop, home gym, or additional storage. Thoughtfully positioned, this home represents a rare opportunity to own a lakefront retreat that delivers serenity, lifestyle and value—all within close proximity to shopping, dining and top-rated schools in a prime location!

2922 Reef Knot Place, Winter Park

$449,999
4 Beds 2 Baths Woodcrest Unit 03 SubDv. 32792 Zip Code
The home you’ve been waiting for is here! This beautifully remodeled gem in the desirable Woodcrest neighborhood of Winter Park is move-in ready and perfect for its next owner. Featuring a sparkling private pool, this home offers modern living with style and comfort. Inside, you’ll find an open-concept floor plan ideal for entertaining and everyday living. Luxury vinyl flooring runs throughout the home, complemented by a fully updated kitchen with advanced lighting, brand-new appliances, and sleek finishes. The kitchen flows seamlessly into the Florida room, where large newly installed windows give a clear view of the inviting pool area. Step through sliding glass doors from the kitchen to enjoy a covered back porch—great for outdoor dining—or access the fully updated laundry room, complete with a new water heater and plumbing. The fourth bedroom is set apart in a private in-law suite layout, just off the laundry room, with its own access to the pool. This oversized room features a walk-in closet with charming barn doors and a front-facing window for natural light—perfect for guests, a home office, or multi-generational living. Conveniently located near shopping, recreation, and top-rated schools, this home checks every box. Don’t miss your chance to own this stunning property—schedule your showing today!

7446 Houston Court E, Winter Park

$450,000
3 Beds 3 Baths Enclave At Hawks Crest SubDv. 32792 Zip Code
Welcome to Hawks Crest – where modern living meets convenience and comfort. Built in 2019, this beautifully upgraded 3-bedroom, 2.5-bath townhome offers the perfect blend of style, function, and low-maintenance living—ready for you to move right in. From the moment you arrive, you’ll be charmed by the paver driveway and walkway framed by lush landscaping, leading to a bold, eye-catching front door. Step inside to find a versatile flex space ideal for a home office, gym, or playroom. The main level features soaring 9+ foot ceilings and tile wood flooring throughout. The open-concept layout effortlessly connects the living room, dining area, and chef-inspired kitchen—perfect for entertaining and everyday life. The kitchen showcases stunning quartz countertops, a stainless steel farmhouse sink, shaker-style cabinetry, and a large island with bar seating. Slide open the rear doors to your fully screened-in patio, a peaceful retreat to enjoy your morning coffee or unwind with evening drinks. Upstairs, a generous loft provides additional space for a second living area, playroom, or workspace. The expansive 23' x 14' primary suite is a true sanctuary, complete with tray ceilings, a luxurious en-suite bath featuring dual vanities, quartz countertops, a walk-in shower, private water closet, and a spacious walk-in closet. Two additional bedrooms—each with ceiling fans and walk-in closets—share a well-appointed full bathroom with quartz counters and a tub/shower combo. The laundry room is conveniently located upstairs and includes a washer and dryer. Hawks Crest is a gated community offering resort-style amenities including a sparkling pool, playground, parks, picnic areas, and more—all with low HOA fees that cover cable, internet landscaping, pool, entrance gate, playground, common areas, and exterior building and roof insurance . Ideally located just a 2-minute walk from the new Park Maitland Preschool and a 5-minute drive to Trinity Prep, one of Central Florida’s top private schools. You’ll also love the convenience of nearby favorites like Foxtail Coffee, Kelly’s Homemade Ice Cream, and The Ravenous Pig. Downtown Winter Park is only 10 minutes away, with easy access to major highways for commuting. Key Updates (2019): Roof | HVAC | Plumbing | Electrical. Don’t miss this opportunity to own a thoughtfully designed, move-in-ready home in one of Winter Park’s most sought-after communities—schedule your private tour today!

1624 Little Wren Lane, Winter Park

$290,000
2 Beds 2 Baths Windward Square Sec 2 SubDv. 32792 Zip Code
Discover One of Winter Park’s Best-Kept Secrets — Windward Square! Welcome to your beautifully renovated 2-bedroom, 2-bath townhome in the highly sought-after Windward Square community. This move-in ready home boasts a bright, open floor plan, with a modern kitchen that flows effortlessly into the spacious living area. The fully updated kitchen features brand-new stainless steel appliances, including a refrigerator with ice maker, plus 42" upper cabinets — ideal for everyday living and entertaining. The primary suite offers a generous walk-in closet, and both bedrooms are filled with natural light. Step outside to your private, screened-in patio and fenced backyard — perfect for morning coffee or evening relaxation. Additional highlights: Three dedicated parking spaces Beautiful green space throughout the community Resort-style amenities at Windward Square include: Three swimming pools, including a dedicated kids' pool Tennis courts Playground Putting Green Welcoming clubhouse Located just minutes from Full Sail University, UCF, shopping, dining, and all that Winter Park has to offer. Zoned for top-rated schools, this townhome provides the perfect blend of comfort, convenience, and community living. Don’t miss your opportunity to own a home in one of Winter Park’s most charming and well-maintained neighborhoods!

2541 Leeward Way, Winter Park

$119,000
2 Beds 2 Baths Golfside Villas Condo SubDv. 32792 Zip Code
Beautifully Remodeled 2-Bedroom Condo Near Full Sail. Great first home or investment property. Discover the perfect blend of comfort and convenience in this beautifully updated 2-bedroom, 2-bathroom second-floor condo, just a short walk from Full Sail University. Ideally located minutes from top hospitals, shopping, dining, and only 15-20 minutes from UCF and Orlando International Airport, easy access to sr436. Step inside to find a bright and inviting living space with tile and newly installed carpet flooring throughout. The community features a sparkling pool and a conveniently located laundry room with coin operated machines. HOA fees cover water, sewer, and exterior maintenance, making this an effortless living experience. The seller is looking for a fast closing.

1000 S Semoran Boulevard Unit 608, Winter Park

$430,000
3 Beds 2 Baths Cedar Ridge Unit 2 SubDv. 32792 Zip Code
Welcome to this well maintained three bedroom, two bathroom pool home, with a one year old roof in Winter Park! Perfectly designed for comfortable living, this home features a versatile office space, ideal for working from home. Inside, you’ll find an open floor plan with vaulted ceilings, spacious living areas with a cozy fireplace surrounded by built in shelves. This home features a well-equipped kitchen with plenty of cabinet space. The bedrooms are generously sized, including a primary suite with a private bathroom and a walk in closet. Step outside to your own private retreat, complete with a sparkling pool and lush landscaping, perfect for relaxing or entertaining in true Florida style. Situated in a desirable neighborhood, you’re just minutes away from excellent schools, nearby charming Park Avenue, delicious dining, parks and nearby access to The 417. This home offers both comfort and convenience in one wonderful package and is ready for someone to personalize and make it truly their own.

2003 Bentwood Drive, Winter Park

$610,000
4 Beds 2 Baths Greenview At Winter Pines SubDv. 32792 Zip Code
OUTSTANDING LOCATION, LOCATION, LOCATION! Peace, quiet, and golf course living! This truly rare opportunity places you alongside the 13th tee and offers tranquil backyard views of the 16th fairway of Winter Park’s beautiful WP18 golf course—a picturesque links-style setting in Winter Park. Tree-lined street welcomes you to this serene setting with NO neighbors front, back or side yard! This single story, 4-bedroom, 2-bath home features over 2,000 sq ft of living space, including formal living and dining rooms, an eat-in kitchen, and a spacious family room with vaulted, beamed ceilings and a cozy wood-burning fireplace. Step outside to a 30x11 covered patio and screen-enclosed pool, ideal for relaxing or entertaining with a view! Additional features include: NEW ROOF (NOVEMBER 2024)* Large indoor laundry room* NO HOA!* Zoned for Brookshire Elementary, Glenridge Middle, and Winter Park High* Seller has lovingly owned this home for 33+ years. Bring your vision and renovation ideas to transform this gem into your own private retreat! WELCOME HOME!

1507 Golfside Drive, Winter Park

$645,000
5 Beds 3 Baths Lake Waunatta Woods SubDv. 32792 Zip Code
Welcome to 4030 Cool Water Ct! Nestled in the highly desirable Lake Waunatta Woods neighborhood, this spacious Winter Park Pool home is zoned for top-rated schools, including Winter Park High School and Lakemont Elementary School. With a new roof installed in 2022, this 5-bedroom, 3-bath home offers peace of mind along with undeniable charm. Situated on an oversized lot surrounded by mature trees and lush landscaping, it’s a rare find in a community known for its large lots, quiet streets, and beautiful greenery. Step inside to soaring ceilings and a stunning formal living room with a wood-burning fireplace and floor-to-ceiling stonework. Natural light pours through the large and numerous windows across the front of the house! This custom-built home exudes unique character throughout, blending timeless architectural details with modern updates that make it truly one-of-a-kind. The heart of the home is a chef’s dream kitchen featuring a massive island, gleaming quartz countertops, stainless steel appliances, and abundant cabinet space. Gorgeous wood floors flow throughout the downstairs living areas, including the formal dining room, a spacious family room, and a full bedroom and bathroom perfect for multigenerational living. Upstairs, you’ll find four additional generously sized bedrooms, all with brand new carpet, and two more full bathrooms, including an oversized primary suite that is massive! The expansive layout ensures privacy and comfort for every member of the household. Step outside to your own tropical retreat: a resort-like, large, screened pool and patio area that’s perfect for year-round fun, relaxation and entertaining! The uniquely shaped pool adds a touch of luxury, while the massive patio seamlessly connects to the kitchen and family room—creating the ultimate indoor-outdoor living experience. The lush landscaping and mostly fenced backyard provide ample privacy and a peaceful atmosphere for entertaining or enjoying quiet family moments. This beautiful property offers the perfect blend of warmth, character, and modern updates in one of Winter Park’s most sought-after neighborhoods. All of the shopping, restaurants, or leisure activities you can dream of are within just a few minutes in any direction! Don’t miss this exceptional opportunity, schedule your private showing today!

4030 Cool Water Court, Winter Park

$472,000
3 Beds 2 Baths Harbour Ridge SubDv. 32792 Zip Code
Nestled in one of Winter Park’s peaceful neighborhoods with *NO HOA*, this meticulously upgraded 3 bedrooms, 2 bath pool home plus 2 versatile bonus rooms, perfectly blends modern comfort, sustainable living, and timeless charm. With two vacant city-owned lots directly to the west, the property enjoys uninterrupted golden sunset views that fill the home with natural light. The exterior showcases a thoughtfully refreshed soft grey paint complemented by elegant slate ledgestone accents on both the front and rear, reflecting true pride of ownership. A sleek, durable **METAL ROOF** installed in 2022 enhances curb appeal while offering long-lasting protection, and a full **wraparound PVC privacy fence** enclosing the property. The main living area boasts tile floors flowing seamlessly throughout the family room, dining and leading into a kitchen that serves as the heart of the home. Granite countertops, custom wood cabinets, stainless steel appliances come together in a space that’s both stylish and highly functional. A Bright Bonus Room off the Family Room, is the perfect space for entertainment or casual retreat. Smart upgrades like a Nest thermostat and programmable KASA light switches allow for effortless, energy efficient control of your environment. The spacious primary suite boats an updated bathroom and connects through French doors to a versatile bonus room, ideal as a home office, nursery, or private retreat, featuring its own closet and a wall-mounted AC unit for personalized comfort. The two additional bedrooms share a full modern bathroom featuring a bathtub. This home is packed with features designed for sustainable, efficient living. Energy saving windows were installed in 2016, while a new HVAC system and upgraded ductwork in 2021 ensure year-round comfort. Twenty-two owned LG solar panels, added in 2022 (owned and fully paid), reduce energy bills to an average of around $30/month and also provide eco-friendly pool heating. Two additional panels with Enphase inverters are included for future expansion. A tankless water heater adds even more efficiency, providing endless hot water on demand while saving on energy costs. A 2023 installed whole house water softener and a generator ready plug wired into the electrical panel offers backup power when needed. Additional smart home conveniences include eight hard-wired surveillance camera ports and full home lighting and climate automation. Plus, this home is completely smoke-free and pet-free. Step outside to your private backyard retreat. A full landscape redesign, paired with a three-zone irrigation system, creates a lush, easy-to-maintain setting. The oversized screened pool enclosure (2022) includes a high-performance super gutter and 400 feet of integrated LED lighting, perfect for evening swims and lively gatherings. Enjoy outdoor living to the fullest with a solar heated pool and shower, a 10x12 gazebo, a 5x7 barbecue gazebo, and a large wooden playground complete with overhead canopy support beams. Fruit lovers will appreciate the mature avocado, apple, mandarin, orange, and pineapple trees! Lovingly transformed over the years, this one-of-a-kind home is a rare find where modern upgrades meet everyday comfort. Listing Price based on a recent professional appraisal, this is your chance to own a truly exceptional property in a quiet, sought-after Winter Park neighborhood. Come experience the lifestyle you’ve been waiting for!

2832 Buccaneer Drive, Winter Park

$750,000
5 Beds 3 Baths Lake Ann Estates Unit 1 SubDv. 32792 Zip Code
One or more photo(s) has been virtually staged. Spacious 5 bedroom, 3 bathroom courtyard ranch home offers the perfect blend of comfort and functionality on a spacious .73 acre lot. Upon entering the home, you step into a foyer with the living room/den, dining room, owner’s suite and en suite bathroom to the left, a centrally located kitchen and the family room and additional bedrooms and bathrooms to the right. The kitchen highlights beautiful cabinets, granite counter tops and an eat-in dining space. The family room features a wood burning fireplace providing a warm and cozy space for relaxation. This split floor plan home offers four additional bedrooms and two bathrooms with a privacy door to separate the bedrooms from the living areas. Enhancing the home’s appeal are two bonus areas: a sitting room overlooking the lanai and pool and an adjacent room ideal for a billiard or rec room with wet bar and counter seating. The oversized pool and screened lanai is perfect for entertaining guests. The front, back and side yards are all generous in size. Two car attached garage, 1 car detached garage and additional outdoor covered parking with electric access. Upgrades include hot water heater 2025, electric panel 2024, pool equipment 2024, exterior & interior paint 2024, new luxury vinyl flooring 2024, new lighting and fans 2024. Located in the well-established community of Lake Ann Estates. Don’t miss out! Call today to schedule your showing.

103 Longhorn Road, Winter Park

$421,000
3 Beds 2 Baths Winter Park Pines SubDv. 32792 Zip Code
Spectacular pool home in the Winter Park Pines on a corner lot with a side entry 2 car garage. Roof replaced in 2018. This 3 bedroom 2 bath home is a blank canvas just waiting to be customized to your particular taste. Pool has gunite with diamond brite finish. The particular location of this home could be perfect for raising a family and pets. Breakfast bar in kitchen. Sliding glass doors in the family room leads to the screened patio and the pool area as well as another set of sliding glass doors in the primary bedroom that opens to the pool area. Pocket doors between living room and family room. Front door also has a glass storm door. Sprinker system on well. Room measurements are approximate. Buyer to verify all schools and room measurements. Pool light and pool heater not working. Pool equipment at the home, washer and dryer and 2nd refrigerator in garage is included.

2817 Fitzooth Drive, Winter Park

$1,010,000
5 Beds 5 Baths Bear Gully Pointe SubDv. 32792 Zip Code
Welcome to this beautifully designed executive pool home with private in-law quarters, nestled on an oversized corner lot in the gated community of Bear Gully Pointe in Winter Park. Thoughtfully crafted with architectural elegance, this residence features timeless details including plantation shutters, crown molding, and hardwood flooring throughout the first floor. Step inside and be greeted by soaring ceilings, a sweeping circular staircase, and expansive views of the screened lanai and sparkling pool and spa. The bright, open layout includes a spacious first-floor primary suite with a sitting area, spa-like bath, and a custom walk-in closet, as well as a second bedroom conveniently located on the main level. Upstairs you’ll find two additional bedrooms, two full bathrooms, and a versatile loft. Ideal for multi-generational living or guest privacy, the detached in-law suite offers its own living space, full bath, and private access from across the pool. At the heart of the home is a gourmet kitchen equipped with granite countertops, stainless steel appliances, gas cooktop, double ovens, center island, butler’s pantry, oversized walk-in pantry, and a cozy breakfast nook—perfect for entertaining. Additional features include a generous laundry room with washer and dryer, a spacious 3-car side-entry garage with epoxy floors, gas water heater, circular front drive, extended side driveway, and beautifully manicured landscaping. Bear Gully Pointe offers community tennis courts and a playground, all just minutes from Trinity Prep, major highways, UCF, and Orlando International Airport. This is Florida living at its finest.

2880 Old Castle Drive, Winter Park

$150,000
2 Beds 3 Baths Hidden Oaks Condo Ph 6 SubDv. 32792 Zip Code
Under contract-accepting backup offers. Great investment opportunity for contractors & handymen!! Location, Location, Location. FOREIGN SELLER! FIRE DAMAGD IN KITCHEN AREA!! PRICE REFLECTS CURRENT CONDITION!!! 2 bedroom, 2.5 bath townhouse located off of Goldenrod Road, just south of University Ave located in the sought after community of Hidden Oaks!. Living and dining room combination, half bath, large kitchen with dine in area. Fenced in private patio. WATER HEATER REPLACED IN 2020 AND AC REPLACED IN 2022!! REMEDIATION & CHEMICAL CLEANING IS CURRENTLY BEING DONE THROUGHOUT THE UNIT. ALL INSULATION AND DRYWALL ARE CURRENTLY BEING REPLACED. UNIT IS BEING SOLD AS-IS AND ALL INTERIOR WALLS WILL BE READY FOR TEXTURE & PAINTING AFTER ALL WALLS ARE CLOSED & REMEDIATION IS COMPLETED. Community pool and playground. Close to UCF, Full Sail, Valencia and Rollins College. HOA fee includes water and trash pickup. all located on the main floor. Currently zoned for sought after WP High School. Plenty of shopping.

3318 Amber Wood Way Unit 100, Winter Park

$270,000
2 Beds 2 Baths Windward Square Sec 1 SubDv. 32792 Zip Code
Nestled in the heart of the highly desirable Windward Square community, this beautifully maintained home offers the perfect blend of comfort, style, and convenience. Step inside from the tranquil front patio and be welcomed by a surprisingly spacious open floor plan that instantly feels like home.The kitchen shines with newer appliances, granite countertops and beautiful upgraded cabinetry. Beautiful tile flooring, freshly painted interior, large closets with stylish closet doors. The thoughtfully designed layout includes 2 bedrooms, 2 full bathrooms, and a versatile BONUS room—ideal as a home office, guest space, or cozy den.Enjoy your morning coffee or unwind in the evening on the large screened-in patio overlooking the newly fenced backyard. Many Recent upgrades offer peace of mind: Replumbed in 2022, Water heater replaced in 2021, TRANE A/C system (installed 8 years ago) with advanced humidity control panel for year-round comfort. In addition, the Windward Square offers a resort-style lifestyle with two sparkling pools, a kiddie pool, tennis courts, shuffleboard, and a playground—all for a remarkably low HOA fee of just $95 per month. You’ll also appreciate the convenience of three private parking spaces directly in front, plus ample guest parking throughout the community. Ideally located just off SR 436 and Howell Branch Road, this home is minutes from shopping, dining, major highways, and top-rated schools. Whether you’re a first-time homebuyer, downsizing, or seeking a prime investment opportunity, this move-in ready gem is not to be missed. Schedule your private showing today and discover why this home stands out!

2426 Windward Way, Winter Park

$518,000
4 Beds 2 Baths Garden Lake Estates Unit 2 SubDv. 32792 Zip Code
Welcome to this beautifully remodeled 4BD/2BA home, featuring tons of updates, energy-efficient systems, and a desirable split floor plan. Enjoy new Luxury LVP flooring throughout the entire residence and ceramic tile in the bathrooms. Upon entry, you’re greeted by a spacious living room that flows seamlessly into a thoughtfully expanded kitchen, complete with custom Schuler cabinets, quartz countertops, a quartz backsplash, Frigidaire Gallery appliances, a 33” undermount sink, a reverse osmosis system, and a hot/cold glass rinser. The kitchen also features a large walk-in pantry with a built-in countertop and a breakfast nook with bench seating and storage—perfect for casual dining and added functionality. Just off the kitchen, the cozy family room provides the perfect space for relaxing or entertaining. The split layout offers three bedrooms on one side and a private primary suite on the other, complete with a bonus room, ideal for a nursery, home office, or flexible space. Both the primary and guest bathrooms were fully remodeled in 2022. Step outside to enjoy a screened-in pool and fenced yard—ideal for year-round outdoor living. Major upgrades include a newer roof (2019), new windows (2022), new Carrier A/C system and ductwork (2024), refreshed attic insulation, a whole-home surge protector, solar panels (2022), a solar pool heater (2023), a water purification system, and more. Located in a top-rated Seminole County school district, this move-in-ready home offers the perfect blend of comfort, and functionality. A true lifestyle upgrade!

1360 Gladiolas Drive, Winter Park

$749,000
4 Beds 2 Baths Brookshire Heights 4th Add SubDv. 32792 Zip Code
Nestled in the heart of sought-after Winter Park, this beautifully updated 4-bedroom, 2-bathroom home offers 2,509 square feet of versatile living space designed for comfort, functionality, and style. Perfect for families or anyone needing room to grow, the home features multiple living areas including a formal living room with a bay window and elegant shutters, a cozy family room, a bright sunroom, and an office space—ideal for remote work or study. The heart of the home is the spacious kitchen, featuring light cabinetry, stainless steel appliances, double ovens, ample storage, and a convenient breakfast bar overlooking the sunroom, which also offers space for casual dining. Enjoy a private retreat in the split floorplan primary suite, complete with generous walk-in closets, dual sinks, and a walk-in shower. Beautiful white oak flooring runs throughout much of the home, adding warmth and sophistication. Step outside to a lushly landscaped backyard with plenty of space to add a pool—your personal outdoor oasis awaits. Huge storage space above the garage. Key updates include a new roof (2018), new electrical panels, AC (2018), Nest thermostat, new irrigation well, paver driveway, and fresh interior/exterior paint (2022)—all ensuring peace of mind and energy efficiency. Zoned for Brookshire Elementary, Glenridge Middle, and Winter Park High schools. With easy access to Winter Park’s iconic Park Avenue and nearby Baldwin Park, you’ll enjoy premier shopping, dining, and entertainment just minutes from your doorstep. Don’t miss the opportunity to own this move-in-ready gem in one of Winter Park’s most desirable neighborhoods!

627 Darcey Drive, Winter Park

$415,000
3 Beds 2 Baths Garden Grove SubDv. 32792 Zip Code
Charming 3-Bedroom, 2-Bathroom Home with Pool in the Heart of Winter Park Nestled in the desirable Park Avenue area of Winter Park, this beautiful single-family home offers the perfect blend of comfort and convenience. Enjoy easy access to the vibrant downtown Winter Park, known for its charming boutiques, cafes, and cultural attractions. This home features 3 spacious bedrooms and 2 bathrooms, with a screened-in in-ground pool—ideal for enjoying Florida's sunny weather. Relax by the cozy fireplace or take advantage of recent upgrades, including a new roof (2021) and electric water heater (2023). Other highlights include a 2-car garage and plenty of space for family living. The property is also easily accessible, with quick access to major highways, including I-4. Distance to key locations: Downtown Orlando: 10 miles Orlando International Airport (MCO): 14 miles Walt Disney World Resort: 15 miles Universal Studios Orlando: 11 miles Daytona Beach: 56 miles Cocoa Beach: 60 miles University of Central Florida (UCF): 11 miles Seminole State College (Sanford/Lake Mary Campus): 15 miles Living in Winter Park means enjoying easy access to local parks, lakes, and outdoor activities, all while being close to key transportation routes. Don’t miss the opportunity to make this charming home your own—schedule your private showing today!

5575 Garden Grove Circle, Winter Park

$200,000
2 Beds 2 Baths Wrenwood Condo SubDv. 32792 Zip Code
Beautifully Updated 2BR/2BA Winter Park Townhome that is move-In Ready for a homeowners or investors. Rare opportunity to own a well-maintained 2-story townhome in a desirable Winter Park community. This spacious unit features 2 large bedrooms and 2 full bathrooms, an open floor plan, and numerous recent updates. Downstairs boasts ceramic tile and premium luxury vinyl flooring. The kitchen and bathrooms have been thoughtfully renovated with modern finishes. Enjoy outdoor living on the private screened patio, with the community pool located just steps away. The home features: Indoor laundry, Roof replaced in 2022, HVAC replaced in 2017, Concrete block construction, Abundant storage space and a Pet-friendly community. Low monthly HOA covers exterior maintenance, roof, building insurance, water, trash, pool, and grounds care. Conveniently located near Full Sail University, Valencia College, and UCF, with quick access to 417, 429, and I-4.

4952 Tangerine Ave Unit 4952, Winter Park

$250,000
3 Beds 2 Baths Villas Of Casselberry Ph 3 SubDv. 32792 Zip Code
Welcome to this charming 3-bedroom, 2-bath home nestled in the desirable Villas of Casselberry community. This zero-lot-line property offers low-maintenance living with the privacy of a single-family home. Featuring a functional layout and a 1-car garage, rear patio and outside storage. This starter home is perfect for first-time buyers, or as an investment. Enjoy easy access to top Seminole County schools and local Orlando area attractions — just minutes from UCF, Full Sail University, OIA, and the vibrant shopping and dining scene along Winter Park’s iconic Park Avenue. Whether you're commuting for work or exploring the best of Central Florida, this home puts you right in the heart of it all.

1827 Blaine Terrace, Winter Park

$286,000
3 Beds 2 Baths Eastbrook Sub Unit 06 Rep Of Pt Of Blk 14 SubDv. 32792 Zip Code
Location, Location, Location! Don’t miss this fantastic opportunity in highly desirable Winter Park—a beautiful 3-bedroom, 2-bath home with a heated pool! Recent Upgrades Include: Pool resurfaced (2023), Electrical panel replaced (2023), New roof and AC (2021), New water heater, Fully fenced backyard for privacy and convenience. While the home boasts major mechanical updates, the price reflects cosmetic updates needed, including fresh paint, new flooring, and bathroom remodels—perfect for adding your personal touch or boosting resale value. No HOA! This property offers huge potential whether you're looking to invest, flip, or make it your dream home. Schedule your showing today!

1670 Clematis Lane, Winter Park

$1,180,000
4 Beds 5 Baths Bear Gully Pointe SubDv. 32792 Zip Code
A rare opportunity to own this beautiful pool home in Winter Park at Bear Gully Pointe, a gated community located on a spring fed 137-acre Lake. This perfect 3-way split floor plan with pool views has an open fireplace to enjoy the mornings & evenings. The conservation area in back makes a very private pool & patio area. Expect to be impressed when entering the home with expansive ceilings, open floor plan, and a beautiful gas fireplace in the family room. A very large kitchen with granite counter tops, Jenn Air appliances, lots of cabinet space, breakfast bar & large pantry. Wood floors and tile throughout the home. This home is perfect for entertaining boasting large open floor plan, lots of natural light and soaring ceilings. Beautiful wrought iron staircase to upstairs bedrooms and office that could be a 5th bedroom. The primary bedroom is on the first floor and one of the bedrooms upstairs has a balcony overlooking the pool and patio with sitting area; a perfect place to enjoy your morning coffee or reading your favorite book. This home has tons of extra storage space and a 3-car garage, tile roof and has recently been re-plumbed. Home is just over 4000 sq ft and sits on almost 1/2 acre. Close to restaurants, shopping, Trinity Prep, Park Avenue, 417, UCF and easy access to Orlando International Airport. Call for your private tour today!

4052 Gilder Rose Place, Winter Park

$177,000
2 Beds 2 Baths Whisperwood Condo SubDv. 32792 Zip Code
MOTIVATED SELLER. Welcome to this cozy and well-maintained condo with a townhome feel nestled in the desirable community of Winter Park. Offering 1,393 square feet of comfortable living space, this 2-bedroom, 1.5-bathroom home features an open-concept layout that creates a warm and inviting atmosphere. The spacious living and dining areas flow seamlessly together, enhanced by Vinyl wood flooring throughout the first floor and windows that bring in plenty of natural light. The thoughtfully designed kitchen includes ample cabinet space and opens to the main living area, making it ideal for both entertaining and everyday living. Upstairs, you'll find two generously sized bedrooms and a full bathroom, while a convenient half-bath is located on the main floor. This home also features an inside laundry area and plenty of storage throughout, offering practical convenience and functionality. Step outside to enjoy a screened-in patio overlooking a private, fenced-in backyard—perfect for morning coffee, relaxing evenings, or hosting friends. A covered carport adds protection and ease, while the location puts you just minutes from shopping, dining, and all the charm of Winter Park. Whether you're a first-time buyer or looking to downsize, this condo blends comfort, style, and convenience in a truly inviting setting.

7466 Canford Court Unit 25, Winter Park

$242,000
2 Beds 2 Baths Four Seasons Condo SubDv. 32792 Zip Code
Accepting Back-Up Offers/Charming 2-Story Condo in the Heart of Winter Park Located in the highly sought-after city of Winter Park, this beautifully maintained 2-bedroom, 1.5-bath condo offers the perfect blend of comfort, convenience, and community living. Along with a dedicated covered carport parking space. Just minutes from Park Avenue, top-rated shopping, and dining destinations, this home puts you at the center of it all. Step inside to a bright and open-concept living area that seamlessly connects the kitchen, dining, and living rooms—ideal for both relaxing and entertaining. The spacious back patio extends your living space outdoors, providing a private oasis for weekend gatherings or quiet evenings. Upstairs, you'll find two generously sized bedrooms, including a primary suite with dual closets for ample storage. The full bathroom is thoughtfully laid out, with a half-bath conveniently located on the main floor. Enjoy resort-style amenities in this well-maintained community, featuring multiple pools, tennis courts, sidewalk-lined courtyards, a fitness center, and a welcoming clubhouse. Whether you're a first-time buyer, downsizing, or looking for a smart investment in one of Central Florida’s most desirable neighborhoods, this home is a must-see! HOA FEE INCLUDES: Maintenance Grounds, Pest Control, Pool Maintenance, Recreational Facilities, Sewer, Trash, Water

200 Saint Andrews Boulevard Unit 3002, Winter Park

$192,000
2 Beds 2 Baths Wrenwood Condo SubDv. 32792 Zip Code
WATCH REAL VIDEO & 3D TOUR! Welcome to 4878 Tangerine Ave, a beautifully MOVE IN READY- NEW ROOF - NEW FLOORS- FRESH PAINT updated 2-bedroom, 2-bathroom condo nestled in the serene and highly desirable Wrenwood Condominiums of Winter Park with Community POOL/GYM and ample parking. Yard maintenance, Roof replacement, Trash, and Water are included in the HOA. Step inside and be greeted by abundant natural light, a spacious open living room, and tasteful updates throughout. The kitchen and bathrooms have been thoughtfully refreshed, while large windows brighten every corner of this inviting space. Step out onto your PRIVATE SCREENED PORCH with extra storage, the perfect spot to unwind with breathtaking views of the expansive, peaceful green space and quiet surroundings. Come view this 2 bed / 2 bath home conveniently located 10mins from Winter Park Downtown Historic District /THE GROVE shopping area 3mins/Rollins College and 5 mins from AdventHealth Winter Pk,, BALDWIN PARK (10mins), UCF (12mins), FULL SAIL university (5mins), the Orlando International Airport (20mins), top-rated restaurants, Winter Park Pines Golf Club, ALDI grocery store(2mins) and with quick access to major highways 408(10mins) and 417(5mins) and freeways—making your daily commute and weekend getaways a breeze. Key Features: • Updated interiors with clean, modern finishes, WOOD KITCHEN cabinets • Large living room ideal for entertaining or relaxing • Private, covered patio with tranquil views • Water, Roof replacement,Yard maintenance, and Trash are included in the HOA • Quiet/private location within a well-kept community • Community swimming pool and ample parking •Zoned in Winter Park High School! This home offers the perfect combination of comfort, convenience, and value—ideal for first-time buyers, downsizers, or anyone seeking low-maintenance living in a prime location. Whether you’re enjoying a peaceful morning on the patio or heading out to explore everything Winter Park has to offer, this home provides the lifestyle you’ve been looking for.

4878 Tangerine Avenue Unit 4878, Winter Park

$800,200
4 Beds 4 Baths N/A SubDv. 32792 Zip Code
One or more photo(s) has been virtually staged. Do you have a vision? Do you love Nature? Welcome to this Exceptional Bear Gully Lakefront Retreat – A Rare Blend of Privacy and Natural Beauty! Refurbish the house as it is, or start new on this amazing rare natural Florida lakefront ground. Tucked away on the serene shores of Bear Gully Lake, this one-of-a-kind property presents a rare opportunity to own a true Florida waterfront sanctuary. Set on a private 137-acre lake—renowned as one of the cleanest in the country—this 1.8 acre property currenty has a four-bedroom, 3.5-bathroom pool home. A 464-foot boardwalk walks you from the house through natural Florida landscape, guiding you to the lake and a 28x28 dock complete with a covered power lift—perfect for boating, fishing, paddle-boarding, wakeboarding, or simply relaxing while taking in sweeping lake views. Back at the house, you'll enter through a private courtyard that reveals a tranquil screened pool and spa with cascading waterfalls and an outdoor kitchen this is a true retreat. Step inside the main home to find soaring ceilings, warm wood accents, and spacious living areas ideal for gathering and entertaining. The heart of the home is a generous kitchen featuring unique granite countertops embedded with petrified wood, a breakfast bar, and seamless flow to both the formal dining room and family room with a cozy wood-burning fireplace. The expansive primary suite on the main level is a private haven, offering its own fireplace, walk-in closet, and spa-inspired ensuite bath. Upstairs, a dramatic loft overlooks the main living space, flanked by two bedrooms with a Jack and Jill bath. Separate from the main house, a private fourth bedroom and third full bath provide the perfect setup for an in-law suite, home office, or guest retreat. Ideally located just minutes from SR 417, UCF, Winter Park, and Downtown Orlando, this lakefront home combines everyday convenience with extraordinary living. Homes like this are rarely available—schedule your private showing today and experience the magic of Bear Gully Lake for yourself.

4107 Gabriella Lane, Winter Park