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$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
$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
$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
$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
$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
$330,000
2 Beds ⋅ 2 Baths ⋅ Winter Park Pines Villas SubDv. ⋅ 32792 Zip Code
*Buyer's financing fell through* Welcome to this beautifully renovated 2-bedroom, 2-bath home located in Winter Park! This move-in ready property features modern finishes throughout, a private courtyard, and a spacious backyard—perfect for relaxing or entertaining. The HVAC was replaced in 2018, offering peace of mind and energy efficiency. Conveniently situated just minutes from AdventHealth Winter Park, Rollins College, Full Sail University, and UCF. Enjoy nearby dining and shopping at East End Market, local favorites along Park Ave, and recreational options like Winter Pines Golf Course. Zoned for the highly sought-after Winter Park High School.

631 Warrenton Road, Winter Park
$455,000
3 Beds ⋅ 2 Baths ⋅ Bennington SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. Welcome Home! This immaculate 3-bedroom, 2-bathroom single family home is perfectly designed for comfortable family living. Featuring a desirable split floor plan, this move in ready gem offers space, style, and convenience in every corner. The heart of the home is the modern kitchen, complete with stainless steel appliances and brand new, gorgeous quartz countertops, perfect for preparing family meals or entertaining guests. Fresh interior paint throughout gives the home a bright, clean, and inviting feel, truly turn key condition! Step outside and enjoy the peaceful charm of a quiet street ending in a cul-de-sac, offering privacy and a wonderful area for families to play. Plus, you’re just minutes from local restaurants, parks, grocery stores, and major highways; everything a busy family needs is right at your fingertips. All that’s missing is you! Priced to sell and waiting for YOU to make it home. Schedule your showing today and see it for yourself. Don't miss it!

3304 Bennington Ct, Winter Park
$379,900
3 Beds ⋅ 2 Baths ⋅ Georgetown Estates SubDv. ⋅ 32792 Zip Code
Excellent value on this 3BR corner lot home in the well-established Georgetown Estates community of Winter Park. Recent quality updates include: (1) Roof new in 2023, (2) Replumbed in 2024, (3) New garage door in 2025, (4) Fresh exterior paint in 2025, (5) Fresh interior paint (bedrooms, baths, kitchen) in 2025, and (6) Bedroom carpeting new in 2025. Layout features spacious living room upon entry and dining area in back, adjacent to your prep kitchen. Kitchen is open to the family room, making for a great gathering space. All bedrooms tucked off the home’s hallway, with the primary suite in the front. Primary suite includes an ensuite bath with shower. Out back, you’ll enjoy having a generous sized screened lanai for relaxing or entertaining. The backyard is fenced and full of lush foliage which helps provide privacy as you enjoy fun in the sun. Plenty of storage space – the garage is extra deep and there’s a storage shed in the backyard. Excellent location – you’ll love the proximity to major roadways. The neighborhood has direct access to both SR 426 and SR 436, and you’re only about 10 minutes from SR 408. You’re 5 minutes from your Publix and about 10 minutes from the fabulous downtown Winter Park. This home was lovingly cared for by the same family for decades. Now it’s your turn to come in and make some new memories. Great deal!

3121 Thistlehill Drive, Winter Park
$365,000
3 Beds ⋅ 2 Baths ⋅ Autumn Glen Ph 1 SubDv. ⋅ 32792 Zip Code
Tucked away in a quiet Winter Park cul-de-sac, this 3-bedroom, 2-bathroom home sits in one of the area’s most convenient spots with low taxes, low HOA, and access to top-rated schools. The layout flows well, with updated bathrooms, an enclosed porch for extra living space, and a backyard that’s great for entertaining. There’s even a partial pond view that adds a little extra charm. Whether you’re a first-time buyer or looking for something you can put your own stamp on, this home offers tons of potential without the high price tag you’ll find elsewhere in Winter Park. The enclosed porch gives you flexible space to hang out, work from home, or host friends—and the yard has plenty of room to make it your own. With great bones, a prime location, and a price that leaves room for updates, this one is a smart buy in a neighborhood that rarely has homes available.

1748 Harvest Cv, Winter Park
$460,000
4 Beds ⋅ 2 Baths ⋅ Willa Grove SubDv. ⋅ 32792 Zip Code
some photos are virtually staged!Nestled on one of the largest pie-shaped lots in Willa Grove, this 4-bedroom, 2-bathroom home offers over 2,300 sq. ft. of versatile living space. Designed with a split-bedroom layout for enhanced privacy, the home features an open-concept family, dining, and kitchen area perfect for entertaining. The family room opens onto a large enclosed lanai overlooking a fenced backyard.The spacious Owner’s suite includes a walk-in closet, dual vanities, a separate shower, and direct access to the backyard. Two additional bedrooms include built-in workstation nooks and share a well-appointed bathroom. A flexible bonus room at the rear of the home can serve as a fifth bedroom, home office, playroom, or theater. Exterior features include a charming front porch, a detached carport with boat parking, a full-size storage shed, and an additional side driveway. a newer roof, 2016 HVAC system, quartz countertops, updated plumbing, improved insulation. Located within walking distance to Tuskawilla Middle School and Lake Howell High School, and just minutes from shopping, dining, parks, Full Sail University, UCF, and the 417. This move-in-ready home combines comfort, convenience, and flexibility—an exceptional opportunity not to be missed.

1742 Willa Circle, 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
$750,000
4 Beds ⋅ 3 Baths ⋅ Meadows At Hawks Crest SubDv. ⋅ 32792 Zip Code
Beautifully appointed on a premier homesite within the gated enclave of Hawk’s Crest, this contemporary masterpiece combines grandeur and elegance for your enjoyment of living. From the moment you step through the front door, soaring ceilings and a gracious foyer welcome you into a world of refined living. The luxurious, all-white kitchen is outfitted with top-of-the-line Café appliances and quartz countertops, ideal for casual family meals and gourmet entertaining. Sunlight pours through oversized windows, illuminating the open-concept floor plan and highlighting the custom stone fireplace in the living room. Just off the living area, the formal dining room showcases a bespoke 63-bottle wine rack set against a striking stone wall, creating a beautiful backdrop for hosting gatherings and entertaining guests. Upstairs, generously proportioned bedrooms offer versatility, while the primary suite presents serene waterfront views, ideal for your morning coffee or evening relaxation. Outside, the community-maintained, landscaped backyard offers beautiful pond views, creating a setting to curate unforgettable memories. Residents of Hawk’s Crest enjoy exclusive resort-style living within a leisurely visit from your front door. Amenities include a resort-style pool, virtual guard gate, clubhouse, fitness center, splash pad, two playgrounds, a dog park and direct access to Lake Howell. Convenience is just a short distance away, with Park Maitland Preschool, Kelly’s Ice Cream and Foxtail Coffee right at the entrance of the neighborhood.

1151 Wildmeadow Run, Winter Park
$468,470
4 Beds ⋅ 2 Baths ⋅ Howell Estates Rep SubDv. ⋅ 32792 Zip Code
Welcome to your private oasis—where thoughtfully designed living spaces and beautiful upgrades come together in one incredible home. Whether it’s poolside afternoons, entertaining under the lanai, or cozy nights inside, this property delivers the Florida lifestyle you’ve been searching for. Step inside this well-maintained split floor plan home and enjoy a spacious family room that flows effortlessly into a covered rear oversized porch and screened-in pool—perfect for relaxing or hosting friends. The remodeled kitchen features upgraded wood cabinetry, granite countertops, stainless steel appliances, and a lovely backsplash. The primary suite offers its own retreat, complete with a separate vanity area, walk-in closet, and updated shower. Throughout the home, you’ll find wood plank vinyl flooring—no carpet—and beautifully upgraded bathrooms with granite countertops and custom tile finishes. The property layout is perfect for anyone needing space for a home office, guest room, or kids' area. The exterior boasts charming arched openings and a private front courtyard, ideal for morning coffee or quiet evenings surrounded by your own landscaping. Step into the backyard and discover the perfect Florida escape: a large covered lanai, sparkling pool, and a privacy fence for ultimate seclusion. It's the ideal spot for grilling, lounging, or soaking up the sunshine. Located just minutes from Park Avenue where you’ll find incredible dining, shopping, and events, plus quick access to 417 for easy travel to the Orlando theme parks or Florida’s stunning beaches. Zoned for top-rated Seminole County schools, this home offers both comfort and convenience in one of Central Florida’s most desirable areas. Don't miss this opportunity to own a beautifully upgraded home in a prime location—schedule your tour today!

1026 Manchester Circle, Winter Park
$750,000
3 Beds ⋅ 2 Baths ⋅ Golfside Golf Course Sec 01 #3055 SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. Outstanding opportunity to be in one of the best neighborhoods, as well as golf holes, of the Winter Park Pines Golf Course and community of Golfside! Discover the perfect blend of comfort, style, and location in this beautifully updated Mid-Century Modern 3-bedroom, 2-bath home nestled on the lush fairway of the 9th hole (formerly the 18th hole.) With 1,740 square feet of living space, this residence offers an open and inviting layout ideal for both relaxation and entertaining. Step outside to your private backyard oasis featuring lush landscaping, a sparkling pool, soothing spa, and cozy firepit — all with serene golf course views. Patio furniture is included! Whether you're enjoying quiet mornings or hosting evening gatherings, this home offers the ultimate Florida lifestyle. It’s zoned for all top-rated schools, close to both downtown Winter Park & Baldwin Park’s shopping and dining areas. Cady Way bike trail access is located just down the street. Additional community places: Advent Health Winter Park Hospital and Medical Complex, Ward Park Athletic Complex, Center for Health & Wellbeing/Crosby Fitness Center, and Cady Way Park, are ALL within the neighborhood! Don’t miss the opportunity to live in one of Winter Park’s most desirable neighborhoods! Please see the attachments for even more details. Reach out to schedule a showing! All offers to be reviewed on Sunday evening, May 11th, 5PM.

2756 Summerfield Road, Winter Park
$465,000
4 Beds ⋅ 2 Baths ⋅ Lakemont Heights SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. Welcome to 1809 Pineview Circle, a charming and move-in-ready 4-bedroom, 2-bathroom home located in the heart of Winter Park. This single-story residence offers 1,631 square feet of well-designed living space on a spacious 8,576 square foot lot. From the moment you arrive, you’ll notice the home’s inviting curb appeal and quiet, tree-lined street that defines this established community. Inside, the home features a bright and open layout with ceramic tile flooring throughout, creating a clean and cohesive look. The generous living area flows seamlessly into a well-appointed kitchen equipped with essential appliances, ample cabinetry, and space for casual dining or entertaining. Each of the four bedrooms offers comfortable proportions and natural light, while the two updated bathrooms are thoughtfully designed with modern fixtures to complement the home’s overall aesthetic. Step outside to a large backyard, perfect for hosting gatherings, gardening, or simply enjoying Florida’s year-round sunshine. Additional highlights include central air conditioning (2019), recently replaced roof (2021), washer and dryer, and a solid concrete slab foundation with block walls. Located just minutes from top-rated schools, including walkable Lakemont Elementary, as well as local favorites like Phelps Park, the Winter Park YMCA, Park Avenue, Rollins College and an array of shopping and dining options, this home combines comfort and convenience in one of Central Florida’s most desirable areas. Whether you're a first-time buyer, growing family, or investor looking for a solid rental opportunity, 1809 Pineview Circle is in a prime location and won’t last long! Don’t miss the chance to make this well-maintained home your own.

1809 Pineview Circle, Winter Park
$689,500
3 Beds ⋅ 2 Baths ⋅ Greenview At Winter Pines SubDv. ⋅ 32792 Zip Code
Nestled on an idyllic tree-lined street, this charming 3-bedroom, 2-bathroom POOL HOME offers the Winter Park Lifestyle you've been dreaming of! Step inside to discover a beautifully appointed kitchen featuring granite countertops and NEW STAINLESS STEEL APPLIANCES. The light and bright formal dining room flows seamlessly into the spacious family room, complete with vaulted ceilings and a cozy wood-burning fireplace. Elegant plantation shutters throughout, adding a touch of sophistication and privacy. Escape to your private primary suite through elegant double doors, boasting a relaxing shower and bathtub, plus a convenient walk-in closet. Enjoy your privacy with the split floor plan. Both guest bedrooms share a bathroom and enjoy their own corner of the house. Outside, your own sparkling pool awaits for endless days of sun-soaked enjoyment, or lounging under the covered brick paver patio. This quarter acre lot allows for plenty of additional yard space around the pool. Upgrades Include: New AC and DUCTWORK (2023), NEW FENCE (2023), NEW PAINT (2023), NEW LANDSCAPING, IRRIGATION, and SOD (2023), NEW APPLIANCES (Dishwasher, Microwave, Refrigerator, Oven, Washer & Dryer) (2022), NEW DISPOSAL (2021), NEW POOL FENCE (2025), & NEW ELECTRICAL PANEL (2019). ZONED for High Rated Winter Park Schools: Brookshire, Elementary, Glenridge Middle School, and Winter Park High School. With quick access to the Cady Way Trail, and a short walk for Golfers to enjoy the Winter Pines Golf Club, this home has everything you’re looking for. ZONED for High Rated Winter Park Schools: Brookshire, Elementary, Glenridge Middle School, and Winter Park High School.

1129 Golfside Drive, Winter Park
$450,000
3 Beds ⋅ 2 Baths ⋅ Woodcrest Unit 5 SubDv. ⋅ 32792 Zip Code
Discover your dream home in Winter Park! This stunning 3-bedroom, 2-bathroom gem sits on a spacious 1/3-acre lot, offering the perfect blend of comfort, style, and outdoor living. Step inside to an inviting open-concept layout, where natural light floods the living, dining, and kitchen areas, creating an ideal space for entertaining or cozy nights. The modern kitchen boasts sleek appliances and ample counter space, flowing seamlessly into the living area. Retreat to the generous primary suite with its own updated bathroom, while two additional bedrooms provide flexibility for guests, a home office, or growing families. Both bathrooms feature contemporary finishes for a touch of luxury. Outside, paradise awaits! Dive into your private pool, perfect for Florida’s sunny days, or relax on the expansive screened lanai, ideal for al fresco dining or morning coffee or a dip into the jetted hot tub. The fully fenced yard offers privacy and plenty of space for pets, play, or gardening. With a new roof, new HVAC system, and plumbing re-pipe in 2016 this home is as worry-free as it is beautiful. Nestled in vibrant Winter Park, you’re minutes from top-rated schools, charming boutiques, gourmet dining, and scenic parks.

5326 Lanyard Court, Winter Park
$586,000
3 Beds ⋅ 2 Baths ⋅ Brookshire Heights 1st Add SubDv. ⋅ 32792 Zip Code
Welcome to this beautifully renovated 3-bedroom, 2-bathroom home in the highly desirable Brookshire Heights neighborhood! Nestled on the charming, tree-lined Banchory Road with sidewalks on both sides, this home is just a short stroll from Brookshire Elementary, the Cady Way Pool, Pickleball Courts, and Trail. In 2018, this home underwent extensive renovations, including a new roof, HVAC system, water heater, and fully updated kitchen and bathrooms. As you arrive, the inviting front porch greets you—a perfect spot to enjoy your morning coffee or unwind with a glass of wine in the evening while watching the kids play. Inside, you'll find an open-concept floor plan designed for effortless entertaining. The kitchen is a chef's dream, featuring soft-close cabinetry, quartz countertops, a spacious breakfast bar, and stainless steel appliances. It seamlessly flows into the living and dining areas, ensuring a bright and welcoming atmosphere. Adjacent to these spaces, a spacious Florida room offers endless possibilities as a playroom, sunroom, or relaxation area. The primary bedroom is a true retreat with two closets, including a walk-in, and extra space ideal for an office or nursery. The en-suite bathroom boasts a large shower, soft-close cabinetry, and quartz countertops. The secondary bathroom is equally well-appointed with a tub/shower combination and matching finishes. Step outside to a generously sized, fully fenced backyard with ample space for kids and pets to play. The home also features an attached 2-car garage and an additional laundry room for added convenience. Other updates include newer windows, re-plumbing, and updated electrical systems. This home offers the perfect blend of modern updates and a prime location, close to top-rated schools, fantastic restaurants, shopping, Ward Park, and the vibrant Park Avenue. Don’t miss this incredible opportunity to make this house your home!

2441 Banchory Road, Winter Park
$390,000
3 Beds ⋅ 3 Baths ⋅ Merrie Oaks Village Ph 01 SubDv. ⋅ 32792 Zip Code
Welcome to 264 Balfour Drive — an exclusive residence within a private enclave of just 13 elegant townhomes in the heart of Winter Park designed by architect Nils Schweizer. a student of Frank Lloyd Wright. Offering an attached two-car garage and a premier location, this home blends sophistication with comfort in every detail. Step into a grand living room where soaring ceilings and expansive windows bathe the space in natural light. The formal dining room transitions effortlessly into a thoughtfully designed galley kitchen, showcasing a newly renovated island, high-end Bosch dishwasher, and a French door leading to a truly remarkable outdoor retreat. The covered courtyard, adorned with a trellised garden and overlooking manicured community green space, offers the perfect setting for elevated entertaining and tranquil evenings under the stars. Upstairs, discover a versatile loft ideal for a refined home office, along with a luxurious primary suite featuring a glass-enclosed porch — a serene escape for morning coffee or evening unwinding. Two additional guest bedrooms and a well-appointed guest bath complete the upper level. This discreet and desirable community offers unmatched access to shopping, dining, Advent Health Medical Campus, Full Sail University, Cady Way Park with bike trails & pickleball courts and a short drive to the renowned charm of Park Avenue. Roof 2012, HVAC 2016. Zoned for top-rated schools: Brookshire Elementary, Glenridge Middle, and Winter Park High. WELCOME HOME!

264 Balfour Drive, Winter Park
$498,000
3 Beds ⋅ 2 Baths ⋅ Winter Park Estates SubDv. ⋅ 32792 Zip Code
Step into a slice of mid-century magic, your private oasis awaits. On an oversized corner lot with no rear neighbors, this one-of-a-kind mid-century gem is more than just a home, it’s an experience. With classic architectural charm, lush landscaping and thoughtful updates, you’ll feel like you’ve stepped back in time without sacrificing modern-day comforts. Enjoy the tranquility of nature with lush, low maintenance landscaping featuring palms, oaks, gardenia, jasmine, plumeria and more. A raised garden bed offers a taste of the good life, growing pineapple, asparagus, Japanese sweet potatoes and melon, ideal for home chefs and garden lovers alike. The irrigation system, with seven zones (two in use), keeps everything thriving with ease. Whether you're entertaining or simply unwinding, the large 9.5-foot-deep pool, newly refinished with tile and pebble tec for a natural lagoon feel, is the ultimate showstopper. And when you're done with a dip? The outdoor shower adds a beachy, resort-like vibe to your daily routine. Inside, enjoy a newly remodeled kitchen that’s as functional as it is stylish, complete with an immense walk-in pantry and great indoor storage throughout. A dedicated indoor washer/dryer area adds everyday convenience, making laundry feel less like a chore. Recent upgrades include new windows and sliders, updated plumbing and air conditioner (approximately three years old), and a roof in excellent condition (approximately 10 years old). The home’s new back windows and sliders frame views of the serene backyard, making indoor-outdoor living seamless. Outside, you’ll love the fabulous airy covered carport, and the long, shaded driveway provides ample space for guests or multiple vehicles, enhancing function and curb appeal. Families will love the top-rated schools nearby, and commuters will appreciate being just 10 minutes to downtown Winter Park, UCF, and *moments from State Road 417 and major highways. Don’t miss your chance to own this rare, private retreat in an unbeatable location. With its timeless style, modern updates and natural beauty, this home is a one-of-a-kind gem.

808 Denton Road, Winter Park
$1,165,000
5 Beds ⋅ 5 Baths ⋅ Cypress Reserve SubDv. ⋅ 32792 Zip Code
Welcome to 2832 Bear Island Pointe in Winter Park's premier gated community, Cypress Reserve! This meticulously maintained estate-like home is move-in-ready with 5 bedrooms plus a large office room with its own bathroom and separate exterior entry. Nestled near the serene Bear Gully Lake, this stunning residence offers the perfect blend of elegance, convenience, and resort-style living. The thoughtfully designed floor plan features a spacious first-floor primary suite with a spa-like ensuite, including double vanities, a soaking tub, a walk-in shower, and a generous walk-in closet (11x13 ft). A gourmet kitchen with granite counter tops and stainless steel appliances makes meal preparation effortless, while the formal living and dining rooms provide an ideal setting for entertaining. With five versatile bedrooms, there is plenty of space for guest rooms, home offices, a gym, or a library. High ceilings (11 feet) throughout the home enhance the open and airy feel. The laundry room is equipped with a stackable washer and dryer, built-in cabinets, and a sink for added convenience. The outdoor space is an entertainer’s dream, featuring a large screened-in pavered patio, an indoor pool and spa, and a built-in barbecue area perfect for hosting gatherings. A spiral staircase leads to a private balcony off the primary suite, offering a peaceful retreat with beautiful views. This home is also equipped with solar panels (owner owned), providing an energy-efficient solution that helps reduce utility costs while promoting sustainable living. Perfectly positioned between world-famous beaches and major attractions, this home is just minutes from top-rated schools, including UCF, Rollins College, Trinity Prep, and The Master's Academy. It also offers easy access to Orlando International Airport, premier healthcare facilities, and the scenic Seminole Trail. Experience the best of Winter Park living in this exceptional home. Schedule your private showing today.

2832 Bear Island Pointe, Winter Park
$790,000
4 Beds ⋅ 3 Baths ⋅ Kenilworth Shores Sec 04 SubDv. ⋅ 32792 Zip Code
Welcome to one of the most sought after neighborhoods of Kenilworth Shores in Winter Park! Nestled among tree-lined streets where the mail is still delivered right to your door, this beautifully appointed 4-bedroom, 3-bathroom home blends timeless elegance with modern comfort. From the moment you step onto the charming brick walkway, you'll fall in love with the lush, mature landscaping and inviting curb appeal. Enter through stately double doors into a home filled with thoughtful details—gleaming hardwood floors, crown molding, chair rail, and classic columns in the living, dining, and family rooms. The functional and spacious kitchen is ready for gatherings large or small, whether it's a festive Thanksgiving dinner or a casual poolside barbecue. A flexible space off the kitchen serves as the perfect spot for a breakfast nook, mudroom, or home office. The primary suite, seamlessly added in 2013, offers a private retreat with its own office/flex space, custom walk-in closet, and French doors opening to the pool area. The luxurious en-suite bath features a pedestal soaking tub, dual vanities, and a large walk-in shower with dual shower heads. Three additional bedrooms are situated on the opposite side of the home, including a secondary primary bedroom with its own en-suite bath—perfect for guests or multigenerational living. Step outside to your private tropical paradise featuring a spacious screened lanai, sparkling pool with sun shelf, fountains, and spa jets—an entertainer’s dream. Located just minutes from the Cady Way Pool, tennis and pickleball courts, playgrounds, Ward Park, Center for Health and Wellbeing, WP AdventHealth Hospital & ER, and top-rated schools (Brookshire, Glenridge and Winter Park High School) and colleges like Rollins, Full Sail, Valencia, and UCF. Plus, you’ll love the convenience of nearby shops, restaurants, and grocery stores. Less than 10 minutes from Downtown Winter Park shopping and fine dining. This is more than a home—it’s a lifestyle. Come experience it for yourself! ROOF - 2013 HVAC - 2013 ELECTRICAL UPDATES - 2013 PLUMBING - 2022 WATER HEATER - 2022

600 Brechin Drive, Winter Park
$749,000
5 Beds ⋅ 2 Baths ⋅ Golfside Golf Course Sec 01 SubDv. ⋅ 32792 Zip Code
Just in time for summer! Here's the trifecta of size, location, and condition that you've been waiting for! This beautiful 5 bedroom, 2 bath, 2 fireplaces, corner lot with a pool home is ready for your family! Come make memories for years to come as this home is large enough to grow in. Beautiful hardwood floors through out main living areas, large tiled Florida room with fireplace overlooking the pool on nearly a third of an acre. A lovely kitchen, suitable for entertaining, with a formal dining and living room on either side with a second fireplace in the living room. Your family will also love having an inside laundry room right off of the 2 car garage. Need lots of storage? No problem! This home has plenty with 3 hall closets, additional closet in the second bathroom, and all of bedrooms have walk in closets! If you need some exercise or want to meet your neighbors, right across the street, is the Winter Park Golf Club where you can walk nine holes or mingle at the new Bonfire restaurant! This house is also zoned for top rated schools, Brookshire Elementary, Glenridge Middle School, and Winter Park High School. All bedrooms have new carpet. Interior and exterior of home has been repainted. Four point system dates are as follows, Roof: 2022, HVAC:2023/2024, Plumbing: 2006, Electrical: 2006, Water heater: Tankless, 2023. All this house needs is you! Come see this beauty today!

2907 Summerfield Road, Winter Park
$266,000
2 Beds ⋅ 2 Baths ⋅ Fernbrook Trails Ph 3 SubDv. ⋅ 32792 Zip Code
This charming 2-bedroom, 2-bath townhome in the quiet and friendly Fernbrook Trails community in Winter Park is ready for it's new owner. This one-story home has a warm, open feel with wood-look tile flooring throughout. The kitchen has everything you need—stainless steel appliances, a closet pantry, and tons of cabinet and counter space—and it opens right up to the dining area, making it great for hosting or just everyday living. The primary bedroom is a cozy retreat with a walk-in closet, ensuite bathroom, and access to a covered lanai where you can relax and unwind. Out back, you’ll find a screened-in porch and a private fenced yard that backs up to a peaceful pond—no rear neighbors! It’s tucked away on a quiet street, and the small HOA even covers your lawn care. You’re just minutes from UCF, the 417, and nearby running trails. It’s the perfect spot if you’re looking for low-maintenance living in a great location!

5518 Cretan Way, Winter Park
$550,000
3 Beds ⋅ 2 Baths ⋅ Brookshire Heights 1st Add SubDv. ⋅ 32792 Zip Code
Charming one-story ranch home walking distance to Brookshire Elementary. Located on a .20-acre lot, this 3-bedroom 1.5 bath, home has 1,352 sq ft., including a screen porch conversion adding sq ft. Kitchen has been completely remodeled with stainless appliances, poured concrete counters, tile backsplash and double ovens. All new vinyl plank flooring throughout. New roof in 2022. New exterior paint. Fantastic location close to shopping, dining, parks, Advent Health, The Wellness Center, and Cady Way pool and trail. Additionally, a short drive to Rollins College, Full Sail University, Winter Park Pines golf course and Baldwin Park. Top-rated Winter Park schools. Great opportunity to add or build new. Welcome home!

2492 Brookshire Avenue, Winter Park
$455,000
4 Beds ⋅ 2 Baths ⋅ Lost Creek SubDv. ⋅ 32792 Zip Code
This meticulously maintained home is in the sought after LOST CREEK Subdivision of Winter Park. The home offers an open floor plan, large rooms, a great location, and volume ceilings. The kitchen has lots of counter space and an abundance of cabinets, plus a pantry. The bedrooms are a three-way split. Extra bedrooms are perfect for a secluded office, home gym, or guest room. The screened patio is accessible from the family room and one of the bedrooms. The open floor plan is excellent for entertaining. Outside you will find a generous STORAGE SHED and whole house GENERAC GENERATOR. Seminole County Schools. The ROOF is BRAND NEW (3-17-2025)! The home just got re-piped, and a NEW HOT WATER HEATER was installed (2-18-2025). The AC was replaced in 2023. The exterior has been recently painted. APPRASIAL has been done, and the home is ready for a new owner!

1157 Valley Creek Run, Winter Park
$710,000
4 Beds ⋅ 3 Baths ⋅ Annebury SubDv. ⋅ 32792 Zip Code
***MULTIPLE OFFERS RECEVIED! PLEASE SUBMIT HIGHEST & BEST OFFER BEFORE 3PM FRIDAY, 4/18/25!!***This exceptional 4-bedroom, 3-bath pool home with a 3-car garage is perfectly positioned on a spacious corner lot in a charming enclave of just 27 homes. Thoughtfully designed and meticulously maintained, this residence is a true gem you won’t want to miss. Inside, you’ll find plantation shutters throughout, wood flooring in all bedrooms, 5¼” baseboards, and walk-in closets in every bedroom—offering both style and function. The primary suite is a true retreat, featuring a coffered ceiling, sliding glass doors to the lanai and pool, and a spa-inspired bathroom complete with a custom linen closet and large walk-in closet. Upon entry, soaring volume ceilings and an open-concept layout create a bright, airy ambiance. The gourmet kitchen seamlessly connects to the great room and showcases GE Profile stainless steel appliances including a double oven, 42” cabinets, granite countertops, and a custom walk-in pantry—perfect for entertaining. Notable upgrades include: New Roof (2021) AC System (2017) Water Softener (2024) Newer Pool Pump The updated laundry room features new overhead cabinetry and countertops, leading into the expansive 3-car garage with a floored attic for additional storage. Located near top-rated schools, University of Central Florida, SR 417, and just minutes from the airport, downtown Orlando, and the beaches—this home is ideally situated for both comfort and convenience. Don’t miss the opportunity to show this stunning property to your most discerning buyer!

1726 Sarong Place, Winter Park
$415,000
3 Beds ⋅ 2 Baths ⋅ Hyde Park SubDv. ⋅ 32792 Zip Code
Location, Location, Location! Welcome to Hyde Park! This lovely home in Winter Park offers a blend of amenities and classic charm. The home boasts an open layout, creating spacious living which is great for entertaining and everyday living. A cozy wood-burning fireplace adds warmth and charm to the living space. New roof installed in 2018, new HVAC system in 2022, freshly painted exterior and interior. The kitchen is equipped with a gas stove for simple to gourmet meals and a large dining area with abundant sunlight. The Hyde Park neighborhood offers additional amenities such as a community dock on Lake Florence for fishing, boating, or skiing, a playground, tennis courts and basketball courts. This property has public water and sewer, as well as natural gas. This convenient location puts you in close proximity to shopping, major highways, and desirable schools, adding to its appeal. The combination of modern updates, functional spaces, and neighborhood amenities, makes this home an attractive option for anyone seeking a comfortable and convenient lifestyle.

3063 Ash Park Loop, Winter Park