181 Virginia Drive Winter Park, FL 32789

$11,795,000 - 5Br/8Ba -  for Sale in Ellno Willo, Winter Park
New
$11,795,000
5 Beds
8 Baths
8,188 SqFt
Status Active
MLS # O6199109
Property Type Single Family Residence
Price Type --
Experience luxury living at its finest with this custom-built masterpiece on the shores of Lake Virginia, proudly crafted by the renowned Phil Kean Design Group. Boasting 5 or 6 bedrooms, 6 full baths, and 2 half baths (plus library/office, 2nd office, loft & lounge area, exercise rm, theatre, bonus/flex room & lots of storage) sprawled across 8188 heated square feet over 3 levels (includes high quality residential elevator), every detail of this home exudes sophistication and elegance. Step through the grand entrance adorned with a custom steel front door from Cantera, where natural marble stone flooring leads you into a space illuminated by art lighting from Troy Lighting and picturesque views directly towards Rollins College Chapel. The wood-paneled walls and ceiling design perfectly complement the custom 3-story Alan Mizrahi chandelier, setting the tone for opulent living. Entertain guests in the formal sitting room, complete with a custom Nero marble fireplace and a breathtaking 60 Alora chandelier. Eurowall 14-foot full collapsing doors seamlessly merge indoor and outdoor living spaces, while the kitchen beckons with Plato cabinetry, an Italian 60-inch range, and 4 slabs of Calacatta Italian marble. The double island, featuring countertops by Grothouse, is a chef's dream, accompanied by amenities like the Amuneal wine cabinet and Dacor full-height wine refrigerator. Relax in the family room under vaulted ceilings, where a 16-foot Eurowall opens to reveal views of the serene outdoors. A custom Nero Marquina marble fireplace adds warmth and charm, while automated draperies offer convenience at your fingertips. Retreat to the primary suite, complete with a beverage center and separate laundry room, before indulging in the luxurious primary bath featuring a bateau cast iron tub imported from London and heated floors. Additional bedrooms, all ensuite with walk-in closets, provide comfort and privacy for family and guests alike. Stay active in the fitness room equipped with wall-to-wall rubber gym flooring and a fully equipped “Mr. Steam” steam room. For entertainment, head to the third-floor theater boasting a 120-inch screen with Sony projector and Triad surround sound speakers. Outside, professional hardscape and landscape design by Corey Mills and Signature Landscape create a picturesque backdrop for outdoor living. Enjoy 148 feet of lake frontage with sea wall spanning property, a renovated boat house, and a newly installed dock with Trex decking and boat lift. Experience resort-style living with a pool designed and installed by Paradise Pools, featuring knife edge and Infinity edge designs, Pent Air equipment with mobile app control, and an outdoor kitchen equipped with DCS appliances, Sunbrite television, and more. Resting on an elevated (apprx ¾ acre lot) on Lake Virginia of the Winter Park Chain-of-Lakes, this exceptional property offers unparalleled luxury and waterfront living. Don't miss the opportunity to make this your own private paradise.

2026 Japonica Road Winter Park, FL 32792

$445,000 - 3Br/2Ba -  for Sale in Winter Woods Unit 04, Winter Park
New
$445,000
3 Beds
2 Baths
1,846 SqFt
Status Active
MLS # O6197886
Property Type Single Family Residence
Price Type --
Welcome to this charming Winter Park home, centrally located with easy access to amenities like Interlachen Country Club, the Winter Park YMCA, Seminole County Schools, Publix, and more. There are 3 bedrooms (one with a murphy bed built in!) and 2 bathrooms on one side of the house and an abundance of living space to enjoy on the other side. The kitchen opens up to a family room with french doors out to a large screened in porch overlooking your pool and spacious backyard. Best of all -- you won't need to do much to get this home ready for your things; HVAC was replaced in 2015, plumbing was updated in 2013, new electrical panel in 2015, and new water heater in 2013. The laminate flooring throughout is a fabulous blank slate and outside the landscaping is mature and well maintained. This home has a lot of great storage space, including a built-in storage shed off of the garage. Winter Woods has an optional HOA that covers things like community landscaping, and neighborhood events.

861 Bonita Drive Winter Park, FL 32789

$4,150,000 - 6Br/8Ba -  for Sale in Comstock Park, Winter Park
New
$4,150,000
6 Beds
8 Baths
6,939 SqFt
Status Active
MLS # O6199396
Property Type Single Family Residence
Price Type --
Welcome to Bonita Drive, located within Winter Park's charming brick-lined streets. This exquisite custom estate spans nearly 7,000 square feet, boasting Mediterranean architecture complemented by lush landscaping, creating a serene oasis in the heart of the city. As you step through the grand double glass-paneled door you're led to an elegant parlor room divided by ornate cast stone columns. The walls of the home are adorned with modern Venetian plaster, while Forbes and Lomax light switches, Waterworks faucets and custom vent covers add a touch of sophistication throughout the home. The gourmet kitchen is at the heart of the home featuring custom cabinetry, marble counter tops, and design elements from Portugal. A Lacanche range offers the convenience of gas and electric ovens. The kitchen is equipped with a spacious pantry room, two Sub-zero refrigerator drawers, a Sub-zero Pro 48 glass door refrigerator, a pebble ice machine, and paired with dual sinks and dishwashers. A butler's pantry, situated between the kitchen and dining area, offers a perfect space for entertaining, complete with a long marble counter for serving, a Sub-zero wine refrigerator, two additional Sub-zero refrigerator drawers, two warming drawers, and plaster shelving for storage. A generously sized primary bedroom is conveniently located off the main living area with privacy in mind, filled with natural light and complete with a sitting area and views of the pool. The primary bathroom suite, renovated in 2019, features designer touches from top to bottom. Connected to the bathroom is a thoughtfully designed closet equipped with custom shelving with plenty of room for storage and dressing. Upstairs is a state-of-the-art home theater, three additional bedrooms, and a dedicated laundry room with the largest capacity washer and dryer. A desk/office area caters to the needs of a home manager. Outside is a covered patio area overlooking the tranquil saltwater pool and spa. An in-law suite with a separate entry and guest quarters over the garage provides privacy and comfort for visitors. The rear garage, boasting three spaces and air conditioning, coupled with the front garage's single space, offers ample parking and storage options. The home has a four-zone air conditioning system ensuring year-round comfort. Additionally, the property is equipped with two tankless water heaters, one on each side of the house, a whole-house generator, and a water softener system. With its timeless elegance and modern amenities, this home offers a unique lifestyle of comfort and sophistication in the heart of Winter Park.

1511 Chestnut Avenue Winter Park, FL 32789

$695,000 - 2Br/2Ba -  for Sale in Lake Knowles Terrace, Winter Park
New
$695,000
2 Beds
2 Baths
1,275 SqFt
Status Active
MLS # O6199975
Property Type Single Family Residence
Price Type --
Welcome to this charming bungalow nestled in Winter Park's beloved Tree Streets neighborhood! You'll love living close by Phelps Park, the YMCA, Lake Knowles, and Lakemont Elementary. Plus, hop on your bike for a quick ride to downtown Winter Park and Park Ave for even more fun. Step inside to find a home that's been lovingly maintained, with backyard spaces perfect for enjoying the Florida sunshine. Relax with a cool drink on the front porch or host barbecues on the screened-in back patio. There's plenty of room in the spacious backyard for games and outdoor fun. Inside, original wood floors add warmth and character to the living areas and bedrooms. Need extra space? You've got it! There's a bonus room that's perfect for a home office, family room, playroom, or your own personal gym. Don't miss out on this fantastic opportunity to call this cozy bungalow home in one of Winter Park's most desirable neighborhoods!

1000 S Semoran Boulevard Unit 510 Winter Park, FL 32792

$209,000 - 2Br/2Ba -  for Sale in Golfside Villas Condo, Winter Park
New
$209,000
2 Beds
2 Baths
1,072 SqFt
Status Active
MLS # O6196852
Property Type Condominium
Price Type --
JUST PAINTED IN DECEMBER 2023 and NEW A/C UNIT 2022. Great Opportunity to own an income-producing rental unit as it is currently rented. 2 bedrooms and 2 bathroom at Golfside Villas. This unit is located on the 2nd floor facing the interior of the building by the pool. One assigned parking space plus guest parking next to the unit. HOA fees includes grounds maintenance, water and sewer. Laundry room located by pool area. Spacious open style living area. Renovated master bathroom. Key access for the pool and laundry area. No washer no dryer hook up inside the unit. Walking distance to Full Sail University and Baldwin Park Emergency Room. Conveniently located minutes to Winter Park Hospital, shopping and dining areas. Approximately 10-15 minutes away to the airport, UCF, Baldwin Park, Downtown Winter Park.

200 Saint Andrews Boulevard Unit 405 Winter Park, FL 32792

$185,000 - 1Br/1Ba -  for Sale in Four Seasons Condo, Winter Park
New
$185,000
1 Bed
1 Bath
727 SqFt
Status Pending
MLS # O6199970
Property Type Condominium
Price Type --
Property being sold as is. In good condition but dated.

1929 Houndslake Drive Winter Park, FL 32792

$449,000 - 3Br/2Ba -  for Sale in Cedar Ridge Unit 1, Winter Park
Open House
New
$449,000
3 Beds
2 Baths
1,584 SqFt
Status Active
MLS # O6199274
Property Type Single Family Residence
Price Type --
One or more photo(s) has been virtually staged. This 3 bedroom, 2 bath, pool home has been lovingly maintained and is move-in ready! From the moment you drive up, you will be impressed by the curb appeal and the oversized driveway. This open floorplan provides tons of space for you to host family gatherings. The kitchen has been nicely renovated with granite countertops and a stainless steel refrigerator and dishwasher. The kitchen and dining floors are a beautiful wood plank ceramic tile. Once you step into the large living room, your eyes will be drawn to the stunning wood beam across the ceiling and the engineered hardwood floors. The generously sized primary bedroom has doors that open to the back yard. Attached to the primary bedroom is your private bathroom with dual sinks, and a large travertine shower with 3 shower heads! There are also 2 walk-in closets! On the opposite side of the home you will find 2 more oversized bedrooms and a full bathroom with a jacuzzi tub. As an added surprise, there is a bonus room off the living room that adds another 200 sq ft (approx.) to the home! Use this space as a home office, play room, family room, bedroom, etc. - the options are limitless! Step out back to your beautiful backyard with your own personal solar heated lap pool. There is a custom built hardy board shed on the side of the house and there is also a car/RV parking pad with full hookup! The irrigation system is hooked up to a well pump. Roof is 2017. This home sits just minutes from Park Avenue, Rollins College, UCF, and tons of restaurants and shops. The only thing missing from this home is YOU. Schedule your private showing today!

1801 Legion Drive Winter Park, FL 32789

$1,690,000 - 5Br/5Ba -  for Sale in Green Oaks Rep 02, Winter Park
Open House
New
$1,690,000
5 Beds
4.5 Baths
3,518 SqFt
Status Active
MLS # O6199755
Property Type Single Family Residence
Price Type --
Welcome to 1801 Legion Drive, a stunning Southern traditional with a huge front porch and white picket fence in one of the best neighborhoods in Winter Park. The main house has 4 bedrooms and 3.5 baths and a separate office. There is an additional bedroom and full bath in the detached guest quarters. A large gourmet kitchen with white cabinetry, a stainless steel Thermador gas range and GE Monogram built-in refrigerator and microwave. The adjacent family room that opens to the kitchen has custom-built in shelving surrounding the brick fireplace and is the perfect place for family night movies. French doors lead to the large covered porch with another brick fireplace and an open patio for dining al fresco and also leads to the detached guest quarters which makes a perfect place for a home gym. Take a cool dip in the saltwater pool that was installed in 2018 or after a long day jump in the hot tub! The living room is located off the porch as well with French doors and features a wet bar and yet another brick fireplace (3). The master bedroom has French doors and two custom built-shelved closets, one is a large walk-in. A central laundry room is conveniently located between the split bedroom plan. There is a secondary master with en-suite and two more bedrooms and a shared bath. Conveniently located between Maitland and Winter Park, enjoy easy access to top-rated schools, upscale shopping, dining destinations, and recreational amenities. Embrace the quintessential Florida lifestyle in this prestigious community. Don't miss your opportunity to own this exceptional residence in Winter Park. Schedule your private tour today and discover the luxury and sophistication of 1801 Legion Dr.

3065 George Mason Avenue Unit B Winter Park, FL 32792

$105,900 - 1Br/1Ba -  for Sale in Colonies, Winter Park
New
$105,900
1 Bed
1 Bath
525 SqFt
Status Active
MLS # O6199315
Property Type Condominium
Price Type --
Coming soon Studio and 1 bathroom condo located at The Colonies Condominium in Winter Park. Galley style kitchen with combination Bedroom, family room, and dining room and great closet space. The Colonies walking distance to grocery Market; Laundromat, and Ice cream Twisty Cone.

1228 N Park Avenue Winter Park, FL 32789

$4,500,000 - 5Br/6Ba -  for Sale in Twelve Oaks, Winter Park
New
$4,500,000
5 Beds
6 Baths
5,320 SqFt
Status Active
MLS # O6199601
Property Type Single Family Residence
Price Type --
Presenting a rare opportunity nestled within the enclave of Twelve Oaks, one of the most coveted areas in Winter Park. Set along a private drive with only a dozen residences this Spanish farmhouse was crafted under the discerning eyes of architect Gary Hancock and master builder Carlos Posada. Spanning 5,320 square feet, this house boasts 5 bedrooms, 4 full baths and 2 half baths. It is the essence of “Olde Winter Park” but was built in 2002. As you enter through the front courtyard and the custom front door you are welcomed into the gathering room adorned with a 13-foot pecky cypress beamed ceiling, Saltillo tile, and a stone fireplace. There is a seamless transition to the loggia that opens to the serene courtyard. The farmhouse gathering kitchen offers opportunities for cooking, dining, and conversation and also opens to the loggia. The first-floor primary suite offers a vaulted ceiling, Australian cypress wood floors, large walk-in closet, adjoining room that can be for exercise or a sitting room to compliment the primary bedroom, and a “hidden” entrance into a fully wood paneled study with built in bookcases and fireplace. The exercise room and study both open to another screened porch. Upstairs you will find 3 bedrooms with 3 full baths and ample closets and storage. The back courtyard is surrounded by beautiful flowers, landscaping and lighting and is covered with a canopy of trees. You will find a fireplace, outdoor kitchen, dining area, and steps leading to the mother-in-law suite over the garage. This well-loved home has been well maintained, with thoughtful details that add to its undeniable charm. Once described as “magical”, this property is truly the essence of Olde Winter Park living. Close to the charming boutiques and restaurants on Park Avenue.

7543 Dockside Street Winter Park, FL 32792

$469,900 - 3Br/2Ba -  for Sale in Woodcrest Unit 5, Winter Park
New
$469,900
3 Beds
2 Baths
1,434 SqFt
Status Active
MLS # S5103770
Property Type Single Family Residence
Price Type --
Winter park!! New roof, ac wiring new, sod in the rear replaced, new breaker panel, backyard cleared, porch set up to for get togethers/Super Bowl parties etc. Here we have a 3 bedroom 2 bath single family home located in a (B) rated school district. This turnkey home is ready for its next owners. Perfect first home or upgrade to a new area with good schools. Centrally located with access to major highways. This home has been tastefully decorated and cared for. Entering the home you see the living room followed by the kitchen and onto a second living area. Home has a state of the art nest thermostat allowing you to control the temperature from your phone. You then encounter 2 guest bedrooms big enough for full size beds. Entering the dining room you can look through the plantation shutters for a nice view of the back yard porch area of the home. The master bedroom fits a king size bed and features a spacious walk-in closet. The master bathroom is updated with sink and glass shower enclosure. Out back you have a screened in porch all wired for tv and entertaining. Past the porch you have a sizable back yard for gardening and or entertaining. Bring your offers!!

1551 Harris Circle Winter Park, FL 32789

$2,100,000 - 4Br/4Ba -  for Sale in Sylvan Lake Shores, Winter Park
New
$2,100,000
4 Beds
3.5 Baths
3,300 SqFt
Status Pending
MLS # O6199085
Property Type Single Family Residence
Price Type --
Under contract-accepting backup offers. Captivating and bathed in abundant natural sunlight, this enchanting 4 bed, 3.5 bath home sits nestled in the heart of Winter Park, boasting over 60' of serene Lake Sylvan frontage. Recently renovated to perfection, this residence seamlessly combines charm with modern elegance. Step inside to discover a haven flooded with natural light, accentuating the stunning hardwood floors and welcoming atmosphere. Entertaining is a breeze with three wood-burning fireplaces, including one in the formal living area, where glass sliders offer panoramic lake views. The heart of the home lies in its gourmet kitchen, featuring stainless steel Bosch appliances, glass cabinetry, and a generously sized butcher block island—a culinary delight and a gathering space for friends and family. Upstairs, the luxurious master suite features cozy wood burning fireplace, his/her walk-in closets, and a spa-like bath boasting a zero-entry shower, soaking tub, and marble countertops—a true retreat for relaxation. Flexibility with a lower level that can serve as a fourth bedroom, home office, or game room, and added gym, while the transformed garage into a second family room and bedroom suite adds even more functionality and style. Step outside where a large front porch, newer back Trex deck, and downstairs patio invite you to enjoy breathtaking lake views . Impeccable additional upgrades in 2021, including a new roof, electrical updates, fresh paint, and modern lighting fixtures, ensure both beauty and functionality. Conveniently located just minutes from Park Avenue shops and restaurants, top-rated schools, and Rollins College, this home offers the quintessential Winter Park lifestyle. Water enthusiasts will appreciate the option for a dock for pontoon boats, kayaks, paddleboards and fishing making this residence perfect for those who crave the tranquility of lakeside living combined with the convenience of urban amenities. Motor boats not permitted. Don't miss the opportunity to experience the captivating charm and natural beauty of this Winter Park gem.

7921 Pleasant Pine Circle Winter Park, FL 32792

$644,900 - 5Br/3Ba -  for Sale in Enclave At Aloma, Winter Park
New
$644,900
5 Beds
3 Baths
2,572 SqFt
Status Pending
MLS # O6197471
Property Type Single Family Residence
Price Type --
Welcome to 7921 Pleasant Pines Circle located in the gated community of Enclave At Aloma in beautiful Winter Park! Built in 2015, this 2-story, 5 bedroom and 3 bathroom home offers 2,572 SF of flexible living space perfect for today's homebuyer. Upon arrival you are greeted by the charming covered front porch, a must have for Florida living. Entering the front door into the foyer entry you will find a study/den or “flex space offering a more private retreat from the spacious and open kitchen, dining and family rooms. Ceilings are over 9 feet and contribute to the overall open and airy feel as does the tasteful and neutral finishes. The kitchen features a center island, stainless appliances, a walk-in pantry and brand new quartz countertops and tile backsplash. Downstairs also has one bedroom, a full bathroom and a storage closet to round out the interior of the first floor. Heading upstairs you will find a spacious primary suite, 3 additional secondary bedrooms, hall bathroom with double sinks, laundry room (with recently upgraded washer and dryer included) and a loft/bonus room! 9 foot ceiling height carries to the second floor. The primary bedroom has a spacious ensuite bathroom with double sinks, large shower and a walk-in closet with custom built-ins. Exterior highlights include the attached 2-car garage, HUGE 10’x38’ structural lanai and large fully fenced backyard. The lot is also irrigated. Home exterior was recently painted in 2023. Other notable home features include the double pane windows and 2 HVAC units zoned by floor with Amazon Smart Thermostats. Enclave At Aloma is a gated community of 127 homes tucked away off Bear Gully Rd. and conveniently located close to plenty of dining and shopping options. Trinity Prep, Rollins College, downtown Winter Park, UCF and Full Sail are all just a short drive away. Residents also benefit from quick access to SR 417 making commutes to downtown Orlando or Orlando International Airport a much easier. The homeowners are the original owners and have lovingly cared for and maintained the property. Don’t miss out on this great opportunity. Be sure to schedule your private showing to tour this move-in ready home today!

215 Sandlewood Trail Unit 7 Winter Park, FL 32789

$300,000 - 2Br/3Ba -  for Sale in Sandalwood Creek Condo Ph 13, Winter Park
Open House
New
$300,000
2 Beds
2.5 Baths
1,132 SqFt
Status Active
MLS # O6198616
Property Type Condominium
Price Type --
WINTER PARK! LOW MONTHLY HOA! END UNIT! Enjoy coming home to your 2 BEDROOM/2.5 BATHROOM CONDO HUD APPROVED home!! As you enter this beauty you will be met with all NEW LUXURY VINYL FLOORING AND NEW BASEBOARDS throughout! You are greeted by your entry way and UPDATED HALF BATHROOM on the right with your TASTEFULLY UPDATED KITCHEN including newer STAINLESS STEEL APPLIANCES, new COUNTERS, PAINTED CABINETS with UPDATED HARDWARE along with NEW SINK and FAUCET and a BAY WINDOW that provides plenty of NATURAL LIGHT! The kitchen overlooks your dinette area WITH NEW LIGHT FIXTURE along with a LARGE LIVING ROOM space that has a FIREPLACE and a sliding glass door that allows you to enjoy mornings or evenings on your COVERED SCREEN PORCH that is surrounded by mature landscaping for PRIVACY. Upstairs you will find your primary suite including UPDATED BATHROOM AND FLOORING, second bedroom with a BALCONY to enjoy the outdoors, and an UPDATED SECOND FULL BATHROOM! The LAUNDRY CLOSET is also upstairs for your convenience. You will love being minutes away from Winter Park Village where there is an assortment of shops, restaurants, groceries stores, coffee shops, movie theaters, etc...This Sweet Condo will not last for long so call your agent today...IT WON'T DISAPPOINT! Roof - 2022, AC - 2023, Hot Water Heater - 2023, Replumbed - 2024