Homes for Sale in Winter Park

HOLIDAY SPECIAL: Seller to pay up to $20,000 towards buyer's closing costs! ENTIRE INTERIOR HAS BEEN FRESHLY PAINTED!! Discover the epitome of Winter Park living in this exceptional Douglas Grand brownstone, ideally located between Park Avenue and Hannibal Square! This remarkable residence features a private two-car garage within the secure Douglas Grand parking facility and boasts a personal street-side entrance, providing easy access to a plethora of shops, restaurants, and the SunRail station. Meticulously renovated in 2020, this townhome offers a stunning, spacious kitchen with an island, in-wall speakers, and sleek wood floors upstairs complemented by elegant new tile downstairs. High ceilings and ambient lighting enhance the open and inviting atmosphere. The luxurious master suite features two walk-in closets, dual vanities, a walk-in shower with double shower heads and body spray, a garden bathtub with smart TV connections, and a linen closet. The second bedroom offers a private bathroom and walk-in closet, while the third bedroom is generously sized with a walk-in closet. All bedrooms are equipped with Cat5 cable for seamless streaming, and the second floor includes a laundry room with ample storage. A new water heater adds to the home's convenience and comfort. High-end finishes throughout include Pella windows and doors, Kohler® fixtures, Sub-Zero, Wolf, and Bosch appliances, quartz countertops, surround sound speakers, and dual AC units. Recent updates feature new light fixtures, wired in-wall speakers, and WiFi-enabled thermostats, ensuring a modern living experience. The Douglas Grand community combines the charm of historical architecture with contemporary amenities. Centrally located in Downtown Winter Park, it provides easy access to the SunRail station, Winter Park Farmers Market, and numerous local attractions. Schedule your private showing today. Property may be under audio and visual surveillance.

Under contract-accepting backup offers. Welcome to your stunning dream home, nestled on an oversized, fenced-in lot in the wonderful Hawk's Crest community of Winter Park. Featuring soaring ceilings and abundant natural light throughout, this home is a haven of modern comfort and elegance. Plantation shutters on the windows and motorized blinds on the sliders add a touch of contemporary convenience. This 4-bedroom, 3.5-bathroom residence boasts a split-level floor plan with an open dining and living room area. Fully opening sliders seamlessly extend your living space onto a large screened-in lanai. The fully updated gourmet kitchen, equipped with stainless steel appliances, is at the heart of the home. On the first floor, you'll find the primary suite and a versatile office space highlighted by 8-foot French doors. Upstairs, a spacious loft and three additional bedrooms offer plenty of room for family and guests. The 2-car garage provides ample storage space. Enjoy a maintenance-free lifestyle at Hawk's Crest, a gated community where the HOA takes care of yard maintenance and irrigation. With a quarterly Master Association fee of $425.00, residents have access to fantastic amenities, including a fitness center, pool, splash pad, clubhouse, park, and playground. Embrace the beautiful Florida weather with direct access to Lake Howell for kayaking, paddle boarding, or fishing via the community dock. Don't miss the opportunity to make this exquisite home your own!

Under contract-accepting backup offers. Charming 3-bedroom, 2-bath home in the highly sought-after Orwin Manor neighborhood. This property boasts a 2019 roof and is perfectly situated between downtown Winter Park, College Park, and Downtown Orlando, offering the best of central Florida living. While the home is in need of updates, it is attractively priced to reflect this opportunity. Don't miss out on the chance to make this house your dream home in an unbeatable location!

Discover the charm and downtown Winter Park ambiance with this two-bedroom plus office, two-bath Mediterranean villa, a true “hidden gem” out of the way to find off Interlachen Avenue! The quaint six-villa condominium community is adjacent to the historic Winter Park Golf Course & Casa Feliz. Just footsteps from the vibrant shopping and dining on Park Avenue, this peaceful, private retreat is a European style sanctuary right in the heart of downtown Winter Park. This 1,610-square-foot, two-level condominium is a unique find and wonderful opportunity to make it your own private oasis. On the main level there is a lovely kitchen open to dining room and gorgeous living area featuring vaulted wood ceilings, a wood-burning fireplace, and two walls of French doors opening to separate private courtyards, covered lanai and fountain... There is also a secondary bedroom suite that includes an ensuite bath, perfect for guests or family. Lastly, there is a secluded office/sunroom with gorgeous arched windows and a separate entrance that offers a versatile space for work or relaxation. Upstairs solely encompasses the spacious primary suite boasting a sitting area, French doors and windows and two balconies including an expansive covered balcony off the bedroom, a walk-in closet, and ensuite bath. Embrace the old-world feel of the Spanish/Mediterranean architecture, complete with a newer community tile roof, recent new exterior paint, and peaceful winding courtyards. A secretive brick drive leads to the unit's two designated parking spots including one in a covered carport. Enjoy the Lock and Leave lifestyle with the enjoyment of downtown living and the seclusion of this Winter Park treasure. Walk to the Winter Park Golf Course, Casa Feliz, and stroll through the iconic streets of downtown Winter Park. Don’t miss this incredible opportunity to own a piece of Winter Park's history.

Welcome to this newly renovated gem nestled along the ninth hole of the WP18 golf course. This stunning property features 2584 square feet of living space, ideal for both relaxation and entertaining. Upon entry, you'll find an inviting open concept living area and kitchen, perfect for hosting guests or unwinding after a long day. With 4 bedrooms, this home offers flexibility for a home office or additional bed rooms. The split floor plan provides a primary bedroom that is a serene escape, complete with an en-suite spa bathroom. This sought after location in Winter Park has dining, shopping, entertainment, and the highly desired Brookshire Elementary just minutes away. Don't miss out on the opportunity to make this remarkable property your new home. Schedule a showing today!

Under contract-accepting backup offers. NO HOA. HURRICANE PROOF WINDOWS! No preparation required, owner has updated all windows including sliding door to pool with new hurricane proof windows. Assumable VA Loan at 2.25% for owners remaining balance. You do not need to be a veteran to qualify. This charming, move-in-ready pool home in Winter Park is fully upgraded and ready for its next owner. Featuring hurricane-rated windows, the property has been meticulously maintained and updated. Key upgrades include a new roof in 2021, a new AC unit in 2023, a renovated pool deck in 2021, new pool screens in 2022, and a pool heater installed in 2023. The appliances were updated in 2023, and the water heater was replaced in 2019. The home was also freshly repainted in 2024, and all 2.5 bathrooms have been modernized. The home is located on over a quarter acre with a fenced in yard.

Welcome to your very own private personal retreat! This truly one of a kind oasis of a property features 1.9 acres of lushly landscaped garden in Winter Park. A four-bedroom, three-bathroom main house with a two-car attached garage and a luxurious pool. With paid-for solar panels and a 37 seer Geo-Thermal HVAC means you will enjoy significant savings on your power bills. The additional detached garage (24x36) includes a roughed-in 20x22 space, perfect for an in-law suite, workshop, more garage space (the possibilities are endless) and an additional one car garage. This property boasts a picturesque pond and a private creek with a charming dock and seating areas for serene relaxation. As you approach the home the circular driveway leads to a large tranquil fountain welcoming you, setting the tone for the beautifully landscaped property. Step inside to find a spacious living room with a wood-burning fireplace, seamlessly flowing into the dining room and a dream kitchen. The kitchen is a chef's paradise, featuring a gas range, built-in oven, large island with seating, granite counters, a stylish tile backsplash and so much more. A bonus room off the kitchen and living room leads to the screened-in pool deck, perfect for entertaining. The saltwater pool with a spa and gas heater offers year-round enjoyment. Back inside, the split bedroom plan ensures privacy for all. The large primary suite includes an ensuite bathroom with a soaking tub, separate walk-in shower, and ample closet space with both a walk-in closet and an additional closet. The second bedroom is adjacent to a full bathroom, while the two additional bedrooms at the rear of the home share the third full bathroom. The outdoor space is equally enchanting, with your own pond and creek. Zoned agricultural, the property also includes a chicken coop, making it ideal for those looking to embrace a more self-sufficient lifestyle. This property is very unique in that the part to the west of the pond is not in the HOA, while the part East of the pond is. The wall along Dike Rd in front of this parcel is owned by the parcel The great location has you able to enjoy the best of Winter Park! Great shopping and dining awaits you! Don't miss the opportunity to see this beautiful property in person. Schedule your showing today and experience the tranquility and luxury of this unique home!

Prestigious Windsong community-Discover luxury living at its finest in this exquisite 5-bedroom, 5 full and 2 half-bathroom estate built by renowned Hal George (Parkland Homes). Boasting a traditional, red brick exterior and surrounded by a private 12 ft hedge, this meticulously maintained, light-filled home offers unparalleled privacy and modern elegance. Upon entry, you're greeted by a grand foyer, setting the tone for the home's impeccable craftsmanship and attention to detail. The main level features a well-appointed office and a spacious primary bedroom retreat that opens gracefully to the pool lanai, offering a seamless indoor-outdoor lifestyle. Beautiful primary bath features travertine marble, a spacious soaking tub, and a large shower, epitomizing luxury and relaxation. The heart of the home revolves around an open yet distinct layout, perfect for daily living and entertaining. The family, dining, and living rooms flow effortlessly, enhanced by new LED lighting and a gas fireplace for added ambiance. The gourmet kitchen is a chef's dream, showcasing granite countertops, pale oak cabinetry, and top-of-the-line appliances including a Wolf gas range, Subzero refrigerator, Bosch dishwasher, and Perrin and Rowe faucets; a window wall behind the dining banquette floods the kitchen with natural light and looks out onto the pool area and private backyard. Dual pantries provide ample storage space. Upstairs, a separate staircase on one side of the house leads to the fifth bedroom/bonus room with walk-in closet and bathroom, ideal for guests or a private retreat. Upstairs from the main living area are three bedrooms with en-suite bathrooms and a fourth “loft” room, perfect for a library, studio or playroom. Outdoors, indulge in resort-style amenities including a recently resurfaced, heated saltwater pool with a gas-heated spa, fiberoptic light tower, and Jandy Digital Assistant controller. The pool deck is at the center of a private, beautifully landscaped, backyard “room” surrounded by walls of green hedges, perfect for early morning coffee and birdsong or a glass of wine in the evening as the sun sets, washing the pool with color. The 2022 designer summer kitchen boasts marble countertops and a stainless steel Wolf gas grill. A pool bathroom adds convenience for guests. A mudroom and laundry area offer practicality and organization. Additional features include completely refinished wood floors throughout, a new security system with video cameras, a central vacuum, three AC units installed between 2015-2018, a whole house dehumidifier installed in 2023, and two hot water heaters. Outside, enjoy immaculate landscaping, a long driveway leading to a three-car garage with Tesla charging station, and serene touches like a Buddha garden. Located in the highly desirable Windsong, residents benefit from exclusive access to the Winter Park Chain of Lakes, pools and water park area for entertaining, and playgrounds. Minutes away from Park Avenue shopping and restaurants, Baldwin Park, parks, playgrounds, and excellent public schools including Brookshire Elementary, Glenridge Middle, and Winter Park High School. Don’t miss this rare opportunity to own a masterpiece in one of Winter Park’s most coveted neighborhoods. Contact us today to schedule your private tour and experience luxury living at its finest.

A custom masterpiece! 5 bedrooms, 5 full baths, and 3 half baths. The 5th bedroom is currently a media room upstairs w/ensuite full bathroom but could easily be a bedroom or in-law suite. The Winter Park Windsong community has many amenities such as lakefront clubhouse, splashpad area for families, lake for fishing/boating and plenty of walking paths along the lakes. The home has a large Master suite which features vaulted ceilings, separate his and her vanities, spa tub w/travertine and glass tile. Master shower has 3 separate water options w/ rainfall head, regular, and handheld option. Split his/her custom closet w/ hidden safe bolted to foundation of home. There is another bedroom downstairs w/ full bath which was used mainly for guests. The living areas are open and perfect for entertaining. The open-plan kitchen has an oversized granite island that can seat up to 8, w/ under-counter lighting and stone covered dimmable halogen “art light”, plus oversized cabinets w/ under-cabinet lighting, a Bosch dishwasher and a Wolf commercial range, Wolf steam oven & Wolf warming drawer, a Subzero refrigerator-freezer, and a custom tiled oven hood. Off the kitchen is a Butler’s Pantry and Walk-In Pantry w/ floor-to-ceiling custom shelving. Adjacent to the kitchen is a remote-controlled natural gas log fireplace w/ floor-to-ceiling stone veneer, and built-in seating w/under-seat hidden storage cabinets and dimmable halogen “art light” above the wood beam mantle. Past the laundry room, stairs lead to the second-floor man cave / game room / media room w/ drop down projector screen and surround sound system, full bath with shower, and hewn log bar with kegerator, plumbed and wired to be able to be easily converted to mother-in-law apartment. It also has a finished, oversized storage room. Across from the living room is a grand staircase leading to the loft area upstairs and two bedrooms w/ a full bath in each bedroom. This loft area space was helpful “homework” quiet space, also good for friends gathering after school or could be another game room. Off from the loft is a large, finished, air-conditioned storage room. The impressive outdoor space features a fully enclosable patio w/ remote-control drop-down screen system, al fresco natural gas grill, custom wood cabinetry, and a wood-burning hand-laid stone fireplace w/ natural gas starter system. Outdoor TV and wired for a second TV. The pool/hot tub is natural gas heated, custom lighting system in both pool and hot tub, pool has swim resistor system for “lap in place” swimming and a newer (May 2022) Hayward heater. Finished 3-car garage with stucco, molding and Loewen windows, plus a driveway that can park up to 8 cars. Just a few more details: Nest climate control, 3 air handlers and zones, whole-house EWS water filtration system (rated at 10 years or 2.5 million gallons), second water filter system at kitchen sink for double-filtered drinking and cooking water, blown foam Icynene insulation, wood floors throughout. Alarm system w/ motion sensors, Loewen windows throughout house, wood beams and coffered ceilings on main floor and master bedroom, Rheem dual tankless natural gas, “continuous on” hot water system, tongue and groove ceilings on front porch and back covered summer kitchen/fireplace area, M & S intercom system throughout, Hidden storage room at entry, keyless Schlage entry system. One-owner custom home - Cahill Builders. Matterport link https://my.matterport.com/show/?m=xvJdom2Npmn

SELLER WILL GIVE A $5,000 CREDIT TOWARDS CLOSING COSTS!! Unlock the potential of this two-bedroom, two-bathroom condominium located in the Colonies community. This unit is has stainless steel appliances and granite countertops in both the kitchen and bathrooms. Each bedroom features spacious walk-in closets. A new A/C unit was just installed! The community has desirable amenities including a pool, and a playground, making it a highly attractive rental option. Strategically located, this condo is within minutes of UCF, Valencia College, and Full Sail University. The surrounding area has great dining, entertainment, and shopping options, ensuring a high demand for rental properties. Additionally, easy access to major highways makes commuting and exploring Central Florida effortless. Capitalize on this exceptional investment opportunity in the Colonies community. Schedule a showing today and discover why this property is the perfect addition to your portfolio.

Under contract-accepting backup offers. Large two-bedroom two bath one story townhome located in popular Windward Square. Exterior has recently been painted with the new association approved colors. Community pools, clubhouse, playground. putting green, shuffleboard courts, and tennis courts are located behind the home. Private parking for three vehicles. HOA fees are $92.77 monthly. Seller will contribute $5,000 toward buyers closing cost.

Luxury is a lifestyle, and this Winter Park modern bungalow on a cobblestone street, is full of natural light, clean lines and crisp open spaces. With three bedrooms and 2.5 baths in the main house, this home has been thoughtfully renovated with style and is a home that beckons the green of the outdoor lifestyle. Over 2,400 square feet in main house and the garage was converted to an additional dwelling unit, adding ADDITIONAL 400 sf or so, current use is a studio, can easily transform to a guest house, mother-in-law suite or back to a garage, whatever function fits your needs. Front motorcourt can accomidate lots of vehicles, easy in and out and includes electric car charging station. The kitchen is open to the gathering room with spacious volume ceilings. Home was recently renovated with stainless appliances, including a Thermador gas range, clean-line cabinets with glass door accents, Cambria Gold quartz countertops, counter seating, a farmhouse sink and gorgeous window to the outside. Main living space is anchored by warm wood floors, with marble floors in bedrooms, all generous in size, with fresh light walls and an extensive lighting package throughout. All baths are updated with marble-influenced accents and gold finishes. Primary suite enjoys sleek authentic Carrera marble seamlessly throughout with walk-in closet for great organization. A luxurious bath retreat showcases a soaking tub, dual sinks and a chic open shower with a frosted window. The natural light in this home adds to the beauty in all spaces. Glass slider doors invite you to the outdoor oasis with an expansive covered pergola, cover is waterproof with the Herculas roof system. Lush greenery and mature landscape and majestic oaks round out the space and topped off with an upscale bar for making entertainment simple. This home was extensively renovated including roof and gutters, re-pipe, newer air conditioners, electrical panels, gas tankless water heater, parking motor court, professional landscape and landscape lighting, the additional separate studio recently updated, paved courtyard, bistro lighting and more. Location is paramount near Winter Park Racquet Club, terrific schools, zoned for Winter Park High, close to Park Avenue, fantastic shopping and restaurants. A great investment opportunity to live among the finest homes in Winter Park and in well well-established neighborhood providing a lifestyle like no other.