Homes for Sale in Winter Park

Experience urban sophistication with a small-town ambiance in this exquisite three-bedroom, 3.5-bath two-story condominium at The Douglas Grand, in the bustling heart of Winter Park. This home embodies luxury living with an array of upgraded high-end millwork that echoes the European-inspired charm of Winter Park. The first level reveals a culinary paradise with Busby custom cabinetry, a state-of-the-art Wolf oven and range, Sub-Zero refrigerator, and stunning quartz granite countertops. Entertain in grandeur in the dining and living rooms adorned with judges paneling and French doors that open to a sunny atrium. A generously sized guest bedroom includes a private bath and balcony offering picturesque views of Morse Boulevard, doubling as a second primary suite. Ascend via the elegant staircase or convenient elevator to the second floor where the opulent primary suite awaits, boasting an expansive walk-in closet, a fireplace and French doors leading to a magnificent 26-foot-wide outdoor terrace. The third bedroom, complete with an en-suite bath and a well-equipped laundry room, round out this level. Step just outside, you’ll discover a vast selection of fine dining and shopping, and cultural options encapsulating the essence of urban convenience combined with a charming neighborhood feel.

535 N Interlachen Avenue #304 Winter Park, FL 32789 Listing $395,000 1 bedroom, 1 ½ bath 726 sq feet. Everything inside is new!! Located in the heart of the historic District of Downtown Winter Park, Park Avenue, Winter Park Golf Course-boutique shopping and locally owned restaurants, and Rollins College. Top floor unit features new electrical, plumbing, new hurricane windows and sliders. Brand new kitchen including custom cabinets, quartz countertops and appliances. All new designer tile in bathrooms, custom vanities, shower tile and new fixtures. A/C 10 year warranty with certified climate control. New Luxury Vinyl Plank flooring. The complex features a new roof, recently resurfaced covered parking, elevator, and courtyard. Offered by Holt Home Team for under $400,000 in Downtown Winter park.

Don't miss seeing this move-in ready Winter Park home with no HOA.! This 3 bed/2 bath (split bedroom plan) home is a short walk to the Eastbrook Elementary and includes 2022 roof, 2024 A/C, double pane windows, plumbing re-piped and newer irrigation on well. The large, open kitchen currently has colorful cabinets but are scheduled to be painted a neutral white at the end of November. The large, attached island has been such a plus for holiday family gatherings as well as after school homework space. The laundry room is very spacious and has been handy for Costco shopping storage or holiday storage. The back screened in patio has been an Oasis for planting and gardening supplies. Outside, you'll find a large yard, perfect for outdoor activities, gardening, and plenty of room for the installation of a pool. Great location and close to Publix, shopping and restaurants.

Located in the heart of Winter Park's downtown corridor, 1010 N Pennsylvania Ave offers a luxurious Mediterranean-inspired design with so many modern upgrades, all just steps from Park Avenue’s shops, Winter Park Village, and Whole Foods Market. This stunning home, set on a prime lot adjacent to the Winter Park Golf Course, provides the perfect balance of privacy and convenience. Upon entering through custom double front doors, you’re greeted by an impressive foyer with soaring ceilings and a striking wall-mounted water fountain. The luxurious primary suite is privately situated on one side of the home and features an elegant bath, dual sinks, exquisite shower, and customized his-and-her walk-in closets. A second bedroom or office/study (with a private ensuite bath and walk-in closet) is also on the first floor across from the primary bedroom. This flexible space includes a custom walnut Murphy bed, allowing for dual use as a guest room or office.Continue into the open-concept home as it seamlessly flows from the living room to the dining room. A massive double-sided gas fireplace serves as a centerpiece between the dining room and family room areas. The gourmet kitchen is a chef's dream, outfitted with Sub-Zero Wolf appliances, a reverse osmosis water system, and a large island with bar-top seating that joins the family room. Oversized windows allow natural light to flood these spaces. Sliding doors open to an expansive 35-foot covered lanai, ideal for entertaining or al fresco dining. The lanai features a summer kitchen (with Egg grill) and retractable screens, leading out to a private saltwater pool and spa, which can be heated quickly through a mobile app. A fenced yard includes a small, turfed area, perfect for pets or play. A gate leads right out to the adjacent golf course. Upstairs, you’ll find a private third bedroom with an ensuite bath, along with a versatile multi-use space that can be used as a gym, theater room, or additional living area. For added privacy, a separate fourth bedroom suite is located at the rear of the home. This apartment-like suite includes a bedroom, private bath, living area with small refrigerator and sink along with a large second-story private terrace with sweeping views of the golf course. This living area features its own outside entry and security system, offering complete independence from the rest of the home and a door within that can be locked to separate, if desired. Additional features include a whole-home Briggs & Stratton generator, water softener system, tankless water heaters, two newer Trane 16 seer HVAC systems, a security system with multiple cameras, and exterior painting with a lifetime transferable warranty. With its unparalleled location and exceptional design, 1010 N Pennsylvania Ave is a rare opportunity to own a home that combines luxury living with modern convenience. Don’t miss your chance to make this exceptional property your next home! Feel free to request an upgrades and features sheet outlining all the wonderful aspects of this home! Seller has recent inspection report and home appraisal.

**This property qualifies for a closing cost credit up to $4,400 through the Seller’s preferred lender.** Welcome home to this charming 4-bedroom, 2-bathroom pool home zoned for top-rated schools in the Seminole County District of Winter Park! Sitting on almost ½ an acre, this spacious lot provides room for your boat, trailer, RV and more! Make your way inside to find the formal living and dining room up front with the floor to ceiling accent mirror wall. This split floor plan features the primary bedroom to the left with the pass-through updated bathroom connecting to a guest bedroom that would make the perfect nursey or at home office. The kitchen located at the heart of the home is the perfect space for family and friends to gather year-round with the dinette on the side, granite countertops, stainless steel appliances, and floor to ceiling cabinetry. Skylights in this open concept space draw in the natural light while creating a cozy feel in the living room tucked up at the back. The fireplace on one side with the sliding glass doors with serene views out back are the perfect setting for frequent movie nights at home. Step out back to the covered patio looking out to the new screened porch with your private solar heated pool and newly resurfaced deck. This fully fenced yard provides ample amounts of privacy while lounging in the pool or running around in the grassy area out back with the little ones. Recent upgrades include new windows, new fence, AC 2020, water softener, new duct work, new insulation, replumbed 2024, interior paint 2024, new bathrooms, new kitchen soft close cabinets, led lighting and under cabinet lighting, new appliances, new washer and dryer, and termite bond. Conveniently located in the coveted Winter Park neighborhood, this home offers easy access to top-rated schools, upscale shopping destinations, gourmet restaurants, and a vibrant cultural scene. Don't miss the opportunity to experience the best of Florida while living in this exceptional property. Schedule your private showing today!

Under contract-accepting backup offers. Impeccable home in the gated community of Hawks Crest in Winter Park. This charmer has 3-bedroom, 2-bath, and 2-car garage. Natural light floods the living space with numerous windows that blend the indoors with the outdoors. Beautiful improvements include paver driveway in front and back patio, designer's paint of neutral colors throughout, double pane windows, exquisite hardwood floor in all bedrooms, lovely quartz counter with matching backsplash in kitchen, all kitchen appliances stay even the almost new refrigerator, practical split floor plan enhancing the day-to day routines, inside utility, tile roof, vinyl fencing for privacy, and 1-story solid block construction. Spacious master bedroom has tray ceiling. Master bath with double vanities has separate tub and shower. HOA includes the yard care even the watering of the yard. This home is completed with enviable elegance with modern convenience. Community amenities include sparkling pool, fitness center, clubhouse, dog park, playground, direct access to Lake Howell for canoeing and kayaking. Rare opportunity for a less-than-5-year-old Winter Park home to come on the market these days! Hurry before it is gone!

Magnificent family home located in the elite Winter Park/ Kenilworth Shores neighborhood. Just a few minutes from the world renowned Park Ave which boasts an abundance of upscale shopping and restaurants. Winter Park is home to Rollins College, ranked one of Americas best. Located in top rated schools district, Brookshire, Glendridge and WPHS. Walk into a stunning living area with a cozy wood burning fireplace that leads into a large dining room and an open and spacious kitchen with all appliances and granite countertops. The home is 3 bedrooms and 2 baths with stunning wood floors. Large master with walk in closet and spacious bathroom. The bonus living areas include a large media room for those game and movie nights with family and friends. Enjoy the Florida evenings and mornings on your 20x18 screened in lanai with picturesque views of your manicured lawn and foliage with a grandfathered 8 ft fence for more privacy. Ceilings fans in all rooms and kitchen, new blinds, new toilets, newer roof, new Lenox HVAC and ductwork, new garage opener and new interior paint. Please see attached for list of upgrades. This home is move in ready for a growing family.

Investor Special! This Winter Park gem is an ideal find for investors or home flippers, with *no HOA* and sturdy block construction for peace of mind. Originally a 3-bedroom, 2-bath layout, the home is currently used as a 4-bedroom, 1-bath due to additional walls added by the previous owner. The second bathroom’s plumbing remains intact, simplifying restoration to the original setup. Featuring a split floorplan and an open layout, this property is perfect for modern renovations. Zoned for top-rated Winter Park schools — Lakemont Elementary, Maitland Middle, and Winter Park High School — it promises significant resale or rental potential. The large backyard includes an oversized, powered shed, ideal for storage, a workshop, or a creative space. With its sought-after location, spacious layout, and investor-friendly features, this home is a blank canvas ready to be transformed. Don’t miss out on this rare opportunity!

large corner lot (.31)nestled among majestic oaks and brick streets in high appreciating area. short walk to Park Ave. to enjoy gourmet restaurants, shopping, scenic boat tours, Rollins college and so much more. Located within the esteemed Winter Park school district. Great Winter Park underground utilities. Home built in 1950s has great bones updated 1970. Pool installed 1987, sewer line from home to road replaced 2009, A/C 2017. Original wood floors, home sits high with crawl space underneath. Value is on lot and location. (lot 97X140)has several live oaks on property. Builders welcome to walk the lot with notice to owner. LISTING AGENT IS OWNER.

Under contract-accepting backup offers. Ranch-style quaint home on corner lot with mature landscaping and open in-ground pool in desirable WINTER PARK PINES with lots of potential to turn into your forever home at a GREAT ENTRY LEVEL PRICE. ROOF is from 2004, FLAT ROOF OVER GARAGE is from MAY 2018 and HVAC is from 2016. The home features 3 bedrooms, 2 bathrooms, 2 car garage, and a Screened porch. The newer washer/dryer set is in the garage. The property is zoned for A-rated schools: Aloma Elementary, Glenridge Middle, and Winter Park High. The community boasts incredible amenities such as Winter Pines Public Golf Course, Cady Way Trail, community pool, park, playground, and recently built new Pickleball & Tennis courts. Close to the Orlando International Airport, local Lynx transportation, restaurants, and shopping centers.

Under contract-accepting backup offers. Welcome to your dream cottage! This adorable 2-bedroom, 2-bathroom charmer has serious curb appeal and tons of character. Step inside to find a cozy living/dining room combo with beautiful original wood floors and so much natural light pouring in from every window. The living room has an electric fireplace perfect for chilly evenings. The kitchen is ready for action with solid wood cabinets, granite counters, a stainless steel refrigerator, a Maytag dishwasher, and a range with hood. The second bedroom and full bathroom (hello, shower/tub combo!) are conveniently located right off the kitchen. Head upstairs to the spacious primary suite with built-in closets and cabinetry, plus a private bathroom. There’s even a bonus flex space off the primary suite that’s currently an office but could be anything you want—nursery, workout room, you name it! Tucked under the stairs, you’ll find a convenient inside laundry room. Outside, the fully fenced backyard is an absolute oasis, with mature trees and a covered back porch decked out in warm wood accents that make you feel like you’re on vacation. Located in the heart of Winter Park, this home is just minutes from all the fun on Orange Avenue and Park Avenue and zoned for top-rated Audubon K-8 and Winter Park High School. With a roof from 2018, AC from 2016, and updated plumbing and electrical, it’s move-in ready. Call today to schedule your private tour—this one won’t last long!

Welcome to this charming 2-bedroom, 2-bathroom condo located on the second floor in one of Central Florida’s most sought-after neighborhoods. This well-maintained unit features a spacious open-concept living area, providing a comfortable and inviting space for both relaxation and entertainment. The community offers an array of fantastic amenities, including a sparkling pool, tennis courts, and a playground, making it perfect for an active lifestyle. Conveniently situated with easy access to shopping, dining, and major highways, you’ll find yourself just minutes from downtown Orlando, the University of Central Florida (UCF), Full Sail University, and the vibrant Winter Park area. This home is ideal for first-time homebuyers or investors seeking a desirable rental property in a prime location. Don’t miss out on the opportunity to make this condo yours – schedule a showing today!