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$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
$2,500,000
5 Beds ⋅ 4 Baths ⋅ Acreage & Unrec SubDv. ⋅ 32792 Zip Code
This approximately 4200 square foot home is situated on a 1.68-acre gorgeous lakefront lot in the desirable Winter Park area. The property features a completely updated main house and a detached the three-car air-conditioned garage is a car collector's dream. The primary bedroom suite offers a tranquil retreat, with modern features, ample square footage and completely remodeled en suite bathroom. The remaining two bedrooms with remodeled hall bath provide comfortable accommodations for family and guests. The updated and remodeled interiors showcase a warm, modern, inviting ambiance, with thoughtful design elements throughout. The open floor plan allows for seamless indoor-outdoor living, with access to the lakefront and private boat dock. The lakefront location offers unparalleled privacy and access to the serene waters, creating a serene and peaceful living environment. The property's unique features, including the updated interiors, separate living spaces, and prime lakefront setting, make it an ideal choice for those seeking a distinctive and well-appointed home. Some of the upgrades include new roof in 2022, New HVAC systems in 2022, new water heater in 2022, new kitchen in 2024, new bathrooms in 2024, new designer light fixtures throughout the house in 2024, upgraded flooring in 2022, new expanded back porch deck in 2022 with stunning views of lake and natural setting, new interior paint in 2024, new exterior paint in 2022, upgraded mother-in-law, guest house, office space, separated rental or teenager's retreat, new boat lift in 2022, new paver driveway in 2022, new water softener in 2022. No HOA restrictions.

2652 Lake Howell Lane, Winter Park
$480,000
4 Beds ⋅ 4 Baths ⋅ Slovak Village SubDv. ⋅ 32792 Zip Code
BRAND NEW ROOF SEPTEMBER 2025! Here’s your opportunity to own a beautifully updated duplex that combines comfort, convenience, and investment potential all in one. Each side offers 2 bedrooms, 1.5 bathrooms, a private driveway, and its own attached garage—ideal for owner-occupants, investors, or those seeking a multi-generational living setup. From the moment you arrive, the lush landscaping and well-kept exterior create a warm, inviting atmosphere. Step into the renovated vacant unit and you’ll immediately notice the fresh paint and luxury vinyl plank flooring that runs throughout the main level. The airy living and dining areas are filled with natural light and offers generous space to relax or entertain. The kitchen has been completely refreshed with sleek granite countertops, stainless steel appliances, modern lighting, silver-toned fixtures, and ample cabinetry, making it as functional as it is stylish. Upstairs, both bedrooms are generously sized and share a fully updated bathroom with granite countertops, a modern vanity, and a tiled walk-in shower. In contrast, the tenant-occupied unit features a shower/tub combo, offering added flexibility. A half bathroom on the main floor adds convenience for guests, while both garages come equipped with washer and dryer hookups—ready for move-in. Step outside to discover a pair of patios tucked beneath shady trees, each fully fenced in for added privacy and space for pets to roam freely, with plenty of room to garden, hang a hammock, or host summer grill-outs. Both sides share the same thoughtful layout, and the home is tucked into a quiet, no-HOA neighborhood—so you can enjoy your space without added fees or restrictions. Conveniently located close to schools, shopping, dining, and everything you need for day-to-day living. Live in one side while earning rental income from the other—the current tenant is in place through 9/30/25, providing steady revenue from day one. With updates already complete and a prime location, this is a rare find you won’t want to miss. Schedule your showing today before it's gone!

2608 Dora Court, Winter Park
$485,000
4 Beds ⋅ 4 Baths ⋅ Slovak Village SubDv. ⋅ 32792 Zip Code
BRAND NEW ROOF SEPTEMBER 2025! Welcome to this fantastic income-producing duplex, offering the perfect blend of comfort, convenience, and opportunity. Each side features 2 bedrooms and 1.5 bathrooms, with its own attached garage and private driveway. From the moment you arrive, you’ll appreciate the meticulously maintained landscaping that enhances the curb appeal and sets a welcoming tone. Step inside the vacant unit to discover fresh renovations, including new paint and luxury vinyl plank flooring that flows seamlessly through the main living areas. The living and dining rooms are spacious and airy, making them ideal for both relaxation and entertaining. The beautifully updated kitchen features brand-new granite countertops, sleek silver fixtures, stainless steel appliances, upgraded lighting, and plenty of cabinetry for all your storage needs. Upstairs, you’ll find two generously sized bedrooms and a shared bathroom that has been thoughtfully renovated with a modern vanity, granite countertops, and a stylish tiled walk-in shower, while the occupied unit features a shower/tub combo for added versatility. A convenient half bath is located downstairs for guests, and each garage includes washer/dryer hookups, adding to the home’s functionality and move-in readiness. Out back, you’ll find two private patios surrounded by shady trees—the prime spot to unwind with a glass of wine and take in beautiful evening sunsets. Both units share an identical floor plan, and the property is nestled in a friendly, no-HOA neighborhood, giving you the freedom to live without added fees or restrictions. Centrally located, you'll be just minutes from top-rated schools, shopping, dining, and everyday essentials. Whether you’re seeking a smart investment, a multi-generational living solution, or the option to live on one side while generating rental income from the other, this duplex offers endless possibilities. The second unit is currently tenant-occupied through 2/28/26, providing immediate income for the new owner. Don’t miss your chance to own this amazing duplex with so much to see. Call today before this rare property is gone!

131 Stefanik Road, 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
$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
$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
$402,500
3 Beds ⋅ 2 Baths ⋅ Harbour Ridge SubDv. ⋅ 32792 Zip Code
This fully reimagined corner-lot residence is more than a renovation; it’s a masterpiece, designed for modern living. Sited on nearly 0.40 acres, the home greets you with bold curb appeal, and sleek paver driveway that signal something truly special inside.

1301 Paradise Lane, Winter Park
$470,000
4 Beds ⋅ 3 Baths ⋅ Winter Park Estates SubDv. ⋅ 32792 Zip Code
Welcome to 417 Carvell Drive—where timeless mid-century modern design meets contemporary comfort. This beautifully updated 4-bedroom, 3-bathroom home sits on a spacious quarter-acre fenced lot in the heart of Winter Park. Thoughtfully designed with a split floor plan, the home features two primary bedrooms, ideal for multi-generational living or guest privacy. One of the suites includes a newly renovated bathroom with elegant modern finishes. The open layout, paired with large windows, fills the home with natural light, creating a warm, inviting atmosphere. The updated kitchen boasts granite countertops, wood cabinetry, and stainless steel appliances, offering both style and functionality. Manicured lawn, and inviting front porch add to the curb appeal. Solar panels add energy efficiency. The expansive backyard provides the perfect setting for relaxation, play, or entertaining. Located just steps from walking and bike paths, Cady Way pool, and Ward Park, this home offers easy access to outdoor recreation. It’s also walkable to shopping and dining, and just minutes from top-rated schools—delivering an ideal blend of comfort, convenience, and community. Bonus: Buyers may receive a closing cost credit of up to $4,850 when using the seller’s preferred lender—ask for details! Don’t miss your chance to own this move-in-ready, eco-conscious home in the heart of Winter Park. Schedule your private showing today!

417 Carvell Drive, Winter Park
$575,000
4 Beds ⋅ 2 Baths ⋅ Kings Cove SubDv. ⋅ 32792 Zip Code
Gorgeous, updated, 4 bedroom pool home in the Winter Park community of Kings Cove! Incredible outdoor oasis with a sparkling screened pool, spacious 35 x 13 covered lanai including a summer kitchen with refrigerator, sink and storage cabinets. The heart of the home is the renovated kitchen with quartz counters, breakfast bar, mosaic tile backsplash, pantry, and a large breakfast nook all overlooking the family room with vaulted ceilings and a wood burning fireplace. The primary suite includes a renovated bath with dual sinks, garden tub and large tiled shower. Second bedroom close by, perfect for home office or nursery. Separate living and dining room gives plenty of space for a family. Updates include New windows (2021), AC (2024), Roof (2019), wood flooring, updated plumbing, exterior painted (2019). Easy access to Hwy 417, shopping, restaurants and more!

4353 Steed Terrace, 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
$450,000
3 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 16 SubDv. ⋅ 32792 Zip Code
Welcome to your dream home in the heart of Central Florida! This immaculate, move-in ready 3-bedroom, 2-bath pool home is a true gem, nestled in an established neighborhood known for its top-rated schools, friendly community, and unbeatable location. Step inside to find tastefully updated living spaces that blend comfort with modern style. As you enter the foyer, you will find the formal living room to your immediate left. Continue on to find a family/bonus room with built-in cabinetry. The kitchen boasts updated finishes, stainless steel appliances (fridge and dishwasher 2023), and plenty of counter space. The dining room is through the kitchen, and is currently being used as an office, with a great view of the outdoor space. The bedrooms are split, offering a separate owner's suite. The home also features a bright and airy Florida room, perfect for morning coffee or quiet evenings. Step outside to your private backyard oasis with a sparkling pool, perfect for cooling off on warm Florida days or hosting weekend BBQs. Mature landscaping adds both privacy and curb appeal, and there's plenty of space for pets or gardening. Just minutes from downtown Winter Park, with easy access to shopping, dining, and major highways, this home truly has it all. Roof is 4 years old. Brand new Carpet in bedrooms. Schedule your showing today.

3317 Dormer Court, Winter Park
$426,000
3 Beds ⋅ 2 Baths ⋅ Winter Woods Unit 04 SubDv. ⋅ 32792 Zip Code
In the sought-after Winter Woods community of Winter Park, this 3-Bedroom and 2-Bathroom home with almost 1,700 SQFT of recently updated living space offers both functionality and convenience. Situated on an oversized lot overlooking a pond, this home is perfect for anyone seeking a turn-key opportunity with optimal privacy. Upon entering the home, a large and spacious living area is to the right, bright with plentiful natural light through the front windows. A hallway leads to the open family room and kitchen providing the ideal space for gathering with family and friends. The updated well-equipped kitchen features granite countertops, bar-top seating, wood cabinetry with ample storage, and newer appliances. The kitchen blends seamlessly to a dining area, also adjacent to the front living room. The master bedroom is located on the left of the home with an en-suite updated bathroom. The other two bedrooms are in the back of the home giving privacy for family or guests. The second bathroom is conveniently located in the hallway from the family room leading to the back bedrooms. All bedrooms are complemented with Luxury Vinyl Flooring. Sliding glass doors lead you to the covered back patio and yard overlooking a pond providing a quiet, peaceful, and serene place to relax and unwind. Just outside the kitchen is a large mudroom with Washer/Dryer and additional pantry or storage space. The mudroom leads to the large two-car garage with an additional work worm. A new roof was installed in 2023 as well as fresh interior and exterior paint. This home is ideally located just minutes from the renowned Park Ave and Rollins College as well as close to Full Sail University. Interlachen Country Club is just around the corner and the golf course runs just behind the pond. With easy access to major roadways leading to the 417 and Orlando International Airport, this home is ideal for active families, professionals, and anyone looking for the perfect Winter Park place to call their own.

2028 Sussex Road, Winter Park
$480,000
4 Beds ⋅ 3 Baths ⋅ Hyde Park SubDv. ⋅ 32792 Zip Code
Back on market due to buyer financing....Welcome to your dream home in the heart of Winter Parks sought after Hyde Park community. Situated at the end of a quiet cul de sac, this charming home offers 4 Bedrooms, 2.5 Baths with 1906 sf of comfort and character.. Step inside to find some fresh interior paint, vaulted ceilings, and a cozy, brick-accented fireplace that creates a warm and inviting atmosphere. Upon entry, you are greeted with cathedral ceilings, an abundance of natural light, and a conveniently located guest bathroom. The open living area is perfect for entertaining or gathering of family and friends. The primary bedroom is located on the first floor for added privacy and features an en-suite bathroom with dual sinks, a garden tub, and a separate shower., and lets not overlook the doors that lead to your outdoor oasis. Upstairs, you'll find a versatile loft space—ideal as a home office, playroom, or additional lounge area—along with three spacious bedrooms and a full bathroom with newly installed flooring. The kitchen and dining area offers ample space, where you'll find lots of cabinets for storage, stainless steel appliances, gas oven, and 2 separate sets of doors that lead to the backyard as well. Step outside to enjoy a large screened-in patio complete with a spacious pool—an essential for those warm Florida days and pesky mosquitos. This space is perfect for entertaining, or relaxing with a glass of wine. The surrounding grassy area, is perfect for your pets and/or gardening. Hyde Park offers fantastic amenities including a tennis court, basketball court, playground, and a community dock with access to Lake Florence. Conveniently located near shops, restaurants, downtown Winter Park, with easy access to the 417 Additional upgrades --- new double-pane windows throughout, new siding on the entire house (2022), and a new roof (2022).

3001 Little Cypress Cove, 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
$420,000
3 Beds ⋅ 2 Baths ⋅ Winter Woods Unit 03 SubDv. ⋅ 32792 Zip Code
Seize this exceptional opportunity to acquire a remarkable property in the esteemed town of Winter Park. The roof is only 4yrs old, with rain gutters around the entire house! The kitchen is updated, featuring a stone countertop, breakfast bar, and ample natural lighting. The GE refrigerator, dishwasher, and stove top are 2yrs old. The professionally maintained oversized swimming pool adds to the property’s allure. This home has been lovingly cared for and cherished by the same owner since 1972! Additional features include a new vinyl fence, new garage door, updated outdoor electrical box, lawn irrigation, and a wheelchair ramp in the garage. The asking price is a fair reflection of the property’s current condition. Come and get your great deal, then make it your own inside and out.

1604 Nottingham Drive, 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
$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
$705,000
4 Beds ⋅ 2 Baths ⋅ Golfside Sec 03 SubDv. ⋅ 32792 Zip Code
NEW LOWER PRICE 6/3/25, OWNER WANTS OFFERS. NO HOA. Fabulous RENOVATED home in the heart of Winter Park, where timeless charm meets tranquil Winter Park Pines golf course living. Nestled on a lush, manicured lot right on the 9th fairway, this expansive REMODELLED OPEN AND AIRY SPLIT-plan residence offers a SPLIT PLAN WITH 4 generously sized bedrooms, 2 full baths, and FABULOUS FLEX SPACE that can be a formal living room, office, playroom, bonus room, etc. This floor plan is effortlessly flowing... perfect for both entertaining and everyday living. Step inside and be greeted by warm natural light, rich wood-tile flooring, and the inviting ambiance of a classic wood-burning fireplace. Don’t let the lovely antique furniture fool you—this home is modern in all the right ways, with updated primary bath, renovated 2nd bath and new 2024 kitchen, an open-concept layout, and thoughtful design throughout. The open kitchen, fully renovated in 2024, is a chef’s delight. It blends seamlessly into the living and dining areas for a truly connected feel, perfect for hosting weekend brunches or casual weeknight dinners. French doors open gracefully to the cozy family room and the private primary suite from the lanai, creating an elegant connection between indoor comfort and outdoor serenity. The primary bathroom has been beautifully updated, and the second bathroom was fully renovated in 2016. Enjoy peace of mind with major system upgrades already completed, including a brand-new roof in 2025, a AC 2021, new water heater 2023, and newer windows throughout the home. Step outside to the screened-in patio and take in the sweeping golf course views, ideal for entertaining, morning coffee, grilling out, or simply enjoying the Florida breeze. Set on a generous 0.25-acre lot with plenty of space to add your dream pool! Families will appreciate the top-tier Winter Park school district, zoned for Brookshire Elementary, Glenridge Middle, and Winter Park High, some of the most sought-after schools in the area. With generous living space, elegant touches, and a truly unbeatable location, this Winter Park Pines gem is more than a house. It’s a lifestyle. Come experience it for yourself!

1139 Fairway Drive, Winter Park
$665,000
4 Beds ⋅ 4 Baths ⋅ Winter Park Pines Rep SubDv. ⋅ 32792 Zip Code
NEW ROOF 2019! GREAT PRICE! SPECTACULAR WINTER PARK HOME COMPLETELY RENOVATED AND UPGRADED INCLUDING A STUNNING KITCHEN! This four bedroom three and a half bath home has been meticulously updated and cared for! It has PORCELAIN WOOD LOOK TILE and WOOD flooring THROUGHOUT and NO CARPET. When you walk in the front door you are greeted by a grand and open design. This one-story home even has an IN LAW SUITE with its own private bathroom. When you walk up to the home you are greeted by the inviting front porch. Once entering the home you will find custom details such as crown molding, stunning countertops that look like artwork and much more! From the kitchen, family room, living room and dining room you can see the backyard and access the huge back lanai which comes with the mounted TV. The master bedroom is large and has a beautiful master bathroom! The secondary rooms are large as well with one being EXCEPTIONALLY LARGE and is an in-law suite. This home is located in the quiet community of Winter Park Pines offering beautiful canopying tree-lined streets and the feeling of a simple life with mail still delivered right to the mailbox at your front door. This home is perfectly located with easy access to anywhere you desire to go. You will be just 3 ½ miles to Park Avenue! In just a few moments drive you can be to the 408 Expressway or I4! This home is located just moments away from the Cady Way Pool where they also have tennis and pickleball courts, playgrounds and so much more. You are just moments from top-rated schools and even close to colleges such as Full Sail, Rollins, UCF and Valencia. Moments from Restaurants, Shopping, Advent Health Wellness Center and so much more! COME LIVE IN THE HEART OF IT ALL YET TUCKED AWAY IN A PEACEFUL QUIET ENCLAVE. Come visit this amazing, warm and friendly Winter Park neighborhood because you are sure to want to stay forever!

2817 Prince John Road, Winter Park
$420,000
3 Beds ⋅ 2 Baths ⋅ Winter Woods Unit 01 SubDv. ⋅ 32792 Zip Code
Don’t miss this beautifully maintained, move-in ready 3-bedroom, 2-bath gem in the highly desirable Winter Park area — and best of all, there’s no HOA! Step into the updated kitchen, complete with solid wood cabinetry, granite countertops, stainless steel appliances, and a wine fridge — perfect for cooking and entertaining. The kitchen seamlessly flows into a spacious great room, where sliding glass doors open to a large covered lanai overlooking a fully fenced backyard — ideal for relaxing evenings or lively gatherings. The primary suite features double closets and a spacious en-suite bathroom with a walk-in shower and dual vanities—ceramic tile flooring and elegant woodwork throughout the home, combining style and durability in every room. Centrally located with quick access to major highways, top shopping and dining spots, and community events. Zoned for highly rated English Estates Elementary, Tuskawilla Middle, and Lake Howell High. This is a rare opportunity to own a move-in-ready home in one of Central Florida’s most sought-after neighborhoods. Schedule your showing today!

2259 King Johns Court, Winter Park
$1,000,000
5 Beds ⋅ 5 Baths ⋅ Waters Edge At Hawks Crest SubDv. ⋅ 32792 Zip Code
This stunning 4,300+ square foot home is situated in sought after Waters Edge at Hawks Crest in Winter Park - a community known for its upscale charm and exceptional amenities. With 5 bedrooms, 4.5 bathrooms, 3 car garage, and a layout designed for both comfort and style, this home is perfect for modern living and effortless entertaining. Step inside to find a thoughtfully designed floor plan, complete with semi-private guest suite and half bath on the main floor. The heart of this home is the chef's kitchen, featuring stainless steel appliances, quartz countertops, a pantry, large island, and breakfast nook for casual meals. The great room offers soaring ceilings and an automatic window shade, creating a bright, airy space with just the right touch of sophistication. Upstairs, enjoy an expansive loft with wet bar. Just beyond the loft is a den/media room that offers the perfect flex space - it could be a movie theater, workout room, lounge, or even used as a 6th bedroom. The primary suite is a true retreat, featuring a walk-in dressing closet and a spa-inspired bathroom. Practical upgrades include an EV charger and generous storage throughout. Beyond your front door, Waters Edge at Hawks Crest offers resort-style amenities including a clubhouse, sparkling community pool, grilling station, playground, dog park, and dock on Lake Howell - perfect for sunsets, kayaking, or simply enjoying the natural beauty of the community. The community has everything you could want without worrying about any upkeep. Don't miss your opportunity to live in one of the newest and most desirable communities in Winter Park. Schedule your showing today!

2011 Soaring Oak Way, Winter Park
$899,000
4 Beds ⋅ 3 Baths ⋅ Waters Edge At Hawks Crest SubDv. ⋅ 32792 Zip Code
FANTASTIC 3000 SQ FT+ WINTER PARK WATER VIEW HOME LOCATED IN HIGHLY SOUGHT AFTER WATERS EDGE AT HAWKS CREST! Hawks Crest is one of Winter Park's finest and newest amenity rich gated communities! This is the very popular PALERMO MODEL WITH ALL THE TOP TIER UPGRADES!!!! Stone finish work, tile roof, optional extended rear screened lanai overlooking the water! Wow! The nicest and most upgraded Palermo to hit the market. Perfectly sited on a premium lot offering breathtaking water fountain views from the large fenced rear yard, expansive screened lanai and all main rooms of the house! An absolutely stunning, immaculate, "better than new construction" single story home with a showroom-like kitchen. Incredible upgrades. Too many to list! This property really needs to be seen in person to truly appreciate the feel, finish, setting and exposure that all come together here so nicely. Incredibly bright, open and airy floor plan that is flooded with natural light! Home boasts the most popular split plan with a generous private luxury primary master suite with water view. This great thoughtfully designed layout features an expansive kitchen/dining/family room combo, split plan primary suite, three additional bedrooms, a very large private office, two more well appointed full bathrooms, a second west wing family room/dining/bonus room combo and a generously-sized laundry room equipped with custom built-in features. The best finishes, location and exposure to hit the market at this price point in the community! Plus a MASSIVE 3 CAR GARAGE!Hawks Crest is a thoughtfully planned community featuring top tier resort-style amenities including swimming pool, virtual guard gate, clubhouse, fitness center, splash pad, playgrounds, dog park, and access to Lake Howell. Easy access to DT Orlando, Winter Park and all major employers! Park Maitland Preschool, Kelly's Ice Cream and Foxtail Coffee shop are located at the front of the neighborhood. A beautiful community that offers the perfect combination of peaceful, natural, Florida living and modern, refined conveniences. Central Florida/Winter Park living at it's best! VIEW WALK THROUGH VIDEO - at Virtual tour link

2012 Soaring Oak Way, Winter Park
$800,000
4 Beds ⋅ 3 Baths ⋅ Preserve At Hawks Crest SubDv. ⋅ 32792 Zip Code
Welcome to your dream home! This beautifully designed 4-bedroom, 3-bathroom home offers an elegant blend of style, comfort, and cutting-edge technology in the sought-after gated community of Hawks Crest, featuring resort-style amenities. Inside, you'll love the spacious interior with an ideal, open-concept floorplan. The home boasts eye-catching crown molding throughout the common areas and primary bedroom, picture frame molding in the front hallway, and a beadboard and molding-accented dining nook. The kitchen is a chef’s delight, featuring quartz countertops, soft-close ceiling-height cabinets, double ovens, stainless steel appliances, and recessed lighting in the living room for a warm and inviting atmosphere. The spacious primary bedroom features an en-suite bathroom with large walk-in closet, dual sinks and a stand-up shower with a tile backsplash, providing a spa-like retreat. Split from the primary, visitors will love the privacy of a guest suite that boasts a private en-suite bath. Two additional guest bedrooms are roomy and offer good closet space. Enjoy the convenience of an interior laundry room that's already plumbed for a sink. Step outside to a spacious extended patio with pavers, perfect for entertaining. Additional conveniences include hanging rack storage in the garage, gutters, and an app-controlled smart home system, managing everything from the front door lock and thermostat to the ovens, sprinkler system, and Ring doorbell. Plus, enjoy top-tier energy efficiency with spray foam insulation and high-performance windows. Located in a gated neighborhood with a virtual guard, you'll have access to an amenity center, resort-style pool with a large sun shelf, cabanas, grills, a gym, clubhouse, playgrounds, a dog park, and direct access to Lake Howell with a fishing dock and kayak launch. Enjoy a short drive to Downtown Winter Park with endless dining and shopping options. Hawks Crest also offers great proximity to Rollins College, UCF, Downtown Orlando, Central Florida beaches, hospitals and medical facilities, world-renowned theme parks including Walt Disney World & Universal Orlando, and Orlando International Airport. This home is a perfect blend of luxury, convenience, and modern living—schedule your private tour today! Click the link for the virtual 3-D tour!

2255 Marsh Sedge Lane, Winter Park
$392,500
3 Beds ⋅ 2 Baths ⋅ Cedar Ridge Unit 2 SubDv. ⋅ 32792 Zip Code
This 3-bedroom, 2-bathroom residence is situated on a corner lot, offering an inviting and comfortable living space. A notable feature of this property is the BRAND NEW ROOF and WATER HEATER, ensuring peace of mind for years to come. The split floor plan enhances both privacy and functionality. The master bedroom boasts a walk-in closet and a private ensuite bathroom. On the opposite side of the home are two generously sized bedrooms accompanied by a full bathroom. The eat-in kitchen is ideal for casual dining and family meals. The spacious living and dining room areas feature sliding glass doors that open onto a large screened-in porch, providing a seamless indoor-outdoor living experience. The screened-in porch overlooks a large yard, providing ample opportunities for outdoor activities and gardening. The property includes a two-car garage, equipped with a hurricane-proof door for added security and convenience. Ideally located, this charming home is near shopping, dining, and numerous other amenities, making it the perfect blend of comfort and convenience. This home is filled with potential. Do not miss the opportunity to make this lovely corner lot residence your own and enjoy the best of quiet neighborhood living.

2100 Shirewood Court, Winter Park
$250,000
3 Beds ⋅ 2 Baths ⋅ Four Seasons Condo SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. Welcome you to your charming 3-bedroom, 2-bathroom condo right in the heart of historic Winter Park! This spacious end unit spans 1,322 square feet and features beautiful designer touches that create a cozy and inviting atmosphere. Enjoy the stylish kitchen and baths along with a large primary bedroom that boasts an ensuite bathroom and a truly walk-in closet. Plus, a garden courtyard located right at your front door. One of the best parts, you’ve got a washer and dryer right in your unit. Everything was rebuilt or replaced since 2013- thanks to a complete rebuild, after a fire. So, you can relax knowing that you’ll enjoy modern comfort in an established neighborhood! This condo is perfect for everyone while still enjoying style and practicality. With nearby schools, parks, Cady Way Trail, and Park Avenue just a stone's throw away, you’ll be living in one of Florida’s most desirable locations. Living here means embracing all that Winter Park has to offer; from dining al fresco with friends in Baldwin Park to exploring local boutiques on Park Avenue. You’re close to great schools like Brookshire Elementary, Glenridge Middle School, and Winter Park High – not to mention Rollins College, Full Sail University, and UCF! The Four Seasons Condo Association takes care of so much for you: lawn care, landscaping, tennis courts, three pools, basically everything you need for easy living! They even cover the building insurance and have an on-site property manager ready to help. I wanted to give you a quick heads-up. We're in the process of getting the condo cleaned up and will be adding professional photos shortly. In the meantime, if you're interested, you owe it to yourself to check it out! Don’t miss out on making this lovely space your new home!

200 Saint Andrews Boulevard Unit 1004, Winter Park
$515,000
3 Beds ⋅ 2 Baths ⋅ Winter Woods Unit 02 SubDv. ⋅ 32792 Zip Code
Fully renovated Winter Park home! Remodeled in 2021, this exquisite home sits on a prime corner lot on a quiet cul-de-sac with sidewalks, just minutes from Interlachen Country Club. It is a short drive to downtown Winter Park’s premier shopping and dining. Designed for both entertaining and everyday living, the spacious open floor plan features upgraded kitchen with new cabinetry, stainless appliances and a large island – perfect for gathering with family and friends. There is an abundance of natural light in all the living areas. The primary suite offers serene garden views and two separate closets, while the split floor plan provides privacy for all. A versatile flex space makes an ideal home office, playroom, gym, or in-law suite. Enjoy year-round relaxation in the swimming pool and take advantage of the convenience of an indoor laundry room. With a newer roof, HVAC, electrical panels, this move-in-ready home is an incredible opportunity for carefree living.

1946 King Arthurs Court, Winter Park
$730,000
5 Beds ⋅ 3 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code
FULLY RENOVATED HOME IN THE HEART OF WINTER PARK! Welcome to 2925 Banchory Rd, a stunning, move-in-ready home featuring top-to-bottom luxury upgrades completed in 2021-2025. Every detail has been meticulously updated, blending modern elegance with the charm and convenience of Winter Park living. Recent upgrades include a fully replaced asphalt shingle roof (Jan 2021), energy-efficient HVAC (Jan 2022), and a completely remodeled kitchen with high-end finishes, new appliances, and custom cabinetry. The home also features three fully remodeled upscale bathrooms, new vinyl windows that enhance natural light and energy efficiency, and a newly installed steel entry door for added security and style. Additional upgrades include an upscale garage door replacement, a refinished pool and deck perfect for outdoor entertaining, and fresh interior and exterior paint in a modern neutral palette. The home also boasts new interior doors, updated lighting throughout, and elegant new tile flooring for a sleek and contemporary feel. Located in a prime Winter Park neighborhood, this home is zoned for top-rated Winter Park schools and is located near Cady Way Trail, offering access to scenic outdoor activities. It is minutes from Baldwin Park and Park Avenue, where boutique shopping, dining, and community events await. With convenient access to MCO Airport and all of Orlando’s top attractions, this fully renovated home is the perfect blend of modern sophistication and ideal location. Don’t miss this opportunity—schedule your private showing today!

2925 Banchory Road, Winter Park
$430,000
4 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 11 SubDv. ⋅ 32792 Zip Code
Prime Winter Park Location – Updated 4-Bedroom Home in Eastbrook with No HOA! Welcome to 3420 Arnel Drive, a beautifully updated 4-bedroom, 2-bath home nestled in the desirable Eastbrook neighborhood of Winter Park—with no HOA! This charming home offers modern updates, spacious living areas, and an unbeatable location just minutes from Park Avenue, top-rated Seminole County schools, and endless shopping, dining, and entertainment. Step inside to find an inviting open floor plan featuring a contemporary kitchen with sleek granite countertops, an oversized island, and stylish modern cabinetry. The family room flows seamlessly to the screened-in covered patio, creating the perfect indoor-outdoor living space. Enjoy easy-maintenance wood-look tile and laminate flooring throughout, plus a spacious fenced backyard, ideal for entertaining or relaxing. Recent upgrades include a newer roof, AC system, water heater, updated electrical panel, and fresh exterior and interior paint—making this home truly move-in ready! Located in a pedestrian-friendly neighborhood, this home is close to Eastbrook Elementary and just a short drive to Park Avenue’s boutique shopping, dining, and cultural attractions. With convenient access to major highways, public transportation, and recreational hotspots like Cady Way Trail and Goldenrod Park, this property offers the perfect blend of suburban tranquility and urban convenience. Don’t miss this incredible opportunity—schedule your private showing today!

3420 Arnel Drive, Winter Park