Winter Park FL Real Estate & Homes for Sale

Once in a lifetime opportunity! 1/3 acre Winter Park lakefront. Over 100 feet on the water with dock and boathouse. Just imagine beautiful sunrises from your spacious lanai and most of the other rooms in the home as well. Then a quick dip in your pool before the day gets rolling OR maybe cast your line out from the dock and land a nice bass for your dinner OR you could boat over to Hillstones for a gourmet dinner or Shake Shack for a casual meal and watch an amazing sunset. It is on an approximately 300 acre private lake with no public access so you don't have a lot of boat traffic at all hours of the day or night. Occasionally you may see a seaplane land for lunch or dinner. Now a little about the home. It is the epitome of mid-century modern. Custom built in 1958 for the National Sales Director of Dale Carnegie, so price was no object. No cutting corners on anything! There was no annual "Street of Dreams" event at that time, but if there had been, this spacious and well planned home would have been the hands down winner, with its stainless appliances and screened in pool with covered lanai. Intercom with music throughout and much much more.But, that was then and this is now. New roof November of 2023. Entire home replumbed, electric upgraded including new main breaker box. Living area has a 12 foot tall brick fireplace, huge laundry room that is also plumbed for a 3rd bath if you wish. Master suite has a walk in closet as does the den. The one in the den is presently set up as a wine cellar. (Sorry, the wines don't stay.) Oversize 2 car garage with built in cabinets.You really need to see it to believe it. Very possibly it will be "Love at First Sight"!

Great opportunity to live in Winter Park in the Dubsdread Golf Community. This 3 bedroom, 2 bath home is situated on a deep lot (50 x 140) with 1283 sq. ft., Bamboo hardwood floors in several rooms, split bedroom floor plan, large kitchen with tile floors, and oak cabinets, and the dining room has a tongue and groove wood ceiling. The primary bedroom has Bamboo floors, tongue and groove wood ceiling and a wall closet, adjoining bath with a shower, dual sinks and the laundry closet for the washer and dryer. The two other bedrooms share the hall bath which is light and bright and has a tub shower. A 12 x 16 sq ft enclosed porch is off the kitchen overlooking the large backyard with an adjacent patio. Two storage sheds in the backyard convey with the property. Home Updates: New Roof in August of 2017, New Electrical panel in August of 2023, Septic System located in the back was Inspected and cleaned out in August of 2023 and the HVAC System in 2018. This home is located minutes from Interstate 4, Downtown Winter Park, Advent Health Hospital and Downtown Orlando.

Nestled in the charming community of Winter Park, 1949 Strathaven Rd. seamlessly blends classic elegance with modern comfort. This four-bedroom, two-bathroom home offers a warm and inviting atmosphere, featuring a new roof, stucco, AC, and water heater. The well-appointed kitchen boasts stainless steel appliances, upgraded cabinetry, and quartz countertops, ideal for both casual meals and entertaining guests. Tile flooring throughout the home. Bathrooms feature beautiful porcelain tile and new vanities. With a spacious backyard and a convenient location near to Lake Baldwin Park, schools, and shopping, this property presents an excellent opportunity to enjoy the quintessential Florida lifestyle in a sought-after neighborhood with no HOA.

Welcome to Winter Park, FL! This charming one-bedroom, one-bathroom apartment is perfectly situated close to shopping and dining options, making it an ideal location for those seeking convenience. The community offers a refreshing pool where you can relax and unwind, and the lawn care service ensures a well-maintained and picturesque environment. With laundry facilities conveniently located on-site, you can easily take care of your laundry needs. Additionally, this apartment provides lake access, allowing you to enjoy the serene beauty of the nearby lake. Don't miss out on this fantastic opportunity to experience the best of Winter Park living.

Under Construction. Look no further than this beautiful modern farmhouse being built on a generous one-acre lot. Tucked back toward the end of a quiet road, the lush green lawn is bordered by picket fences and horse farms. You'll love the private country feel, while enjoying all the conveniences that Winter Park has to offer. The open-concept floor plan features 4 spacious bedrooms and 3 full bathrooms, plus a large upstairs bonus room and 3 car garage. If a pool is right for your family, there's plenty of room to add the pool of your dreams. Don't miss the opportunity to select your finishes to truly make it your own! Home is being sold As-Is and not the completed home.

Newly Renovated 4-bedroom 3-bath pool home in Virginia Heights Winter Park neighborhood. Zoned for Audubon k-8 School.

This 4-bedroom, 3.5-bath home located in Winter Park is truly stunning. From the moment you step inside, you'll be captivated by the attention to detail and the warm ambiance that permeates the entire home. The wood flooring in the foyer continues throughout most of the first floor, creating a beautiful and cohesive look. The office/study near the entry features a gas fireplace and windowpane pocket doors, offering a cozy and private space. The dining room is spacious and includes a large window seat, a convenient pass-through butler's pantry, and a wine cooler, perfect for entertaining and hosting unforgettable gatherings. Prepare to be amazed by the kitchen, which showcases custom wood cabinetry, commercial-style KitchenAid appliances, and a natural gas range. The open layout seamlessly connects the kitchen to the dining nook and great room, promoting effortless entertaining and family bonding. The great room opens up to a breathtaking courtyard lanai with a private saltwater pool, complete with fire and water features - a true oasis. The rear yard is secure with custom fencing and lighting, ensuring privacy and safety. The ground-floor primary bedroom offers a serene escape with double walk-in closets and a spa-like bath. Indulge in the hydro-massage tub, revel in the glass walk-in shower, and appreciate the double vanities, all designed to enhance your daily pampering routine. Upstairs, you'll find a versatile bonus room, three additional bedrooms, and two full baths. But that's not all. Step onto the unique covered outdoor space equipped with a gas fireplace, TV hookup, and summer kitchen, making it an ideal space for relaxation and outdoor enjoyment. This home is a work of art, featuring custom plantation shutters and thoughtfully designed feature walls, perfect for showcasing your prized artwork. Dimmable light controls, Nest thermostats, and app-enabled pool controls, convenience and energy efficiency are always at your fingertips. A charming residence adorned with a fresh coat of pristine white paint, accentuated by elegant blue ink details adorned with high-end carpeting, and enhanced with modern lighting fixtures and ceiling fans, this home is ready for you to move right in and make your own. Located in desirable Winter Park, this property offers proximity to the Winter Park Racquet Club, Park Avenue's shops and restaurants, the YMCA, and top-rated schools in Central Florida. Embrace the lifestyle you've always dreamed of in this exceptional Winter Park home.

Nestled in a cozy Winter Park neighborhood, this 3 bedroom/2 bath home is just steps away from Park Avenue, Rollins College, UCF and 436. It's been updated with a newer roof and A/C and has a family-friendly open plan. The family room has sliding glass doors leading to the spacious fenced backyard with a large patio. The kitchen has granite countertops, wood cabinets and stainless steel appliances. Flooring throughout is either ceramic tile or classic vinyl plank--no carpet!! Bathrooms have also been updated with new vanities and the master bathroom features a large walk-in shower. Oversized garage with extra storage space. Enjoy the top-rated Winter Park schools and no homeowners association!

This sophisticated New York-style condo, located on the fifth floor, offers picturesque tree-top and lake views. The one-story unit, spanning over 2000 square feet, has been beautifully updated with custom millwork throughout. It delivers an open layout featuring oversized living and dining areas that lead to an outdoor porch, perfect for indoor/outdoor entertaining. The stylish kitchen is well-equipped with custom wood cabinets, stainless steel appliances, granite countertops, and center island with breakfast bar. The condo includes a spacious guest suite with double closets and a dramatic guest bath with custom designer vanity & lighting plus large walk-in shower. The very generous Owner's suite offers plenty of additional lounging areas and treetop views. The spa-like owner's bath boasts dual custom vanities, a soaking tub, and a large walk-in closet with built-ins. Additional features include specialty glass panels doors throughout, automated blinds in the living room, and an indoor laundry closet. The well-maintained complex, located on the shores of Lake Osceola, provides underground parking and a storage closet, along with amenities such as a pool and community room. Notably, the property comes with a deeded boat slip to the Chain of Lakes. Situated just steps away from Winter Park's vibrant Park Avenue, residents can easily enjoy cafes, eateries, museums, and boutiques, as well as the convenience of Sun Rail/Amtrak. Overall, this condo offers a luxurious and convenient lifestyle in a sought-after location. The Condo fee includes: ELECTRIC, GAS, WATER, SEWER, MAINTENANCE, ON SITE MANAGER, POOL, GROUNDS MAINTENANCE, ROOFS, INSURANCE EXTERIOR and more. Mail and packages delivered to your front door - Easy Living!

Come and see this beautiful efficient fully equipped

Florida living at its finest! Situated on a pond overlooking the 7th fairway of the Winter Park Pines golf course (WP18), this 4 bedroom/2 bath, 2020 sq ft ranch home offers serene views of the pool, pond and well-manicured golf course. Enjoy the beauty of nature while sitting on your screen-enclosed lanai or soaking in the pool's hot tub. This one-story home offers a functional split floor plan with the primary and secondary bedroom (currently used as an office) on one side and 2 additional bedrooms and bath on the other side. Light and bright with an open floor plan, this property has had extensive renovations over the last 5 years including addition of wood flooring to secondary areas in "17, guest bath gut and remodel in "18, salt pool resurface and re-tile in "20, primary bath gut and remodel in "21, new roof, windows and French/sliding doors in '22, and new AC and kitchen remodel in 2023. The galley kitchen has a commercial grade refrigerator and a 6-bottle wine refrigerator, neutral tile backsplash, open shelving, and quartz counters. The adjoining family room has beamed, vaulted ceiling with the fireplace as the focal point and 2 sets of doors leading out to the lanai. The primary bedroom /bath features a walk-in closet, dual sinks and expansive shower with a slider opening to the screened lanai. Other amenities include an indoor laundry room, 2 car garage, side yard dog run. Great location with easy access to the shops and restaurants on Park Ave, a short walk or bike ride to the scenic Cady Way Trail or a short drive to Baldwin Park, the Crosby Wellness Center and the airport. Top rated school district. This beautiful home, located on a tree-canopied street in an established neighborhood, is a rare gem!

One or more photo(s) has been virtually staged. This charming Orwin Manor POOL home in Winter Park is ready for a new owner! This home has 2 bedrooms with another room that could be an office or third bedroom, along with two full bathrooms. The front door entry is filled with light from 3 large arched windows. As you enter the living and dining spaces, you will notice the original hardwood floors and beautiful gas fireplace for those cozy evenings. The Kitchen is open to the Family room with high ceilings and both overlook the back yard with Screened Porch and open Pool. The Master bedroom has 2 large closets and adjoins a full bathroom with double sinks and tub/shower. The Second bedroom can share this bathroom. Toward the back of the house is another large room that could be used as a 3rd bedroom or office with the second full bathroom nearby. There is an interior Laundry room off of the Kitchen. With a screened Porch leading to the Pool area, there is plenty of room for lounging and relaxing with friends and family. Don't miss the large storage/utility room with laundry tub. Recent upgrades include: Roof replaced 2023, HVAC replaced 2022, electrical panel has been updated and home has fresh interior paint and new carpet. This location is conveniently nestled between downtown Orlando, College Park and Winter Park with easy access to shopping and restaurants. This home has been listed in the City of Winter Park historic register.

Discover this captivating Mediterranean-style 3BR/4BA home nestled in the highly desirable Windsong community, boasting 2,952 sq. ft. of luxurious living space. The grand front entry welcomes you with a stone surround, travertine floors, and a solid mahogany door. The kitchen features custom stained-wood cabinets, granite countertops, a 6 burner gas range, island, and breakfast bar, complemented by a large hidden pantry and a butler's pantry leading to the dining room. The elegant wine room, adorned with a brick ceiling and iron gate, adds a touch of sophistication. The family room, with floor-to-ceiling stacked sliding glass doors, vaulted stained wood coffer ceiling, offers seamless patio and pool access, perfect for entertaining. The master suite features an oversized walk-in closet with custom wood built-ins, a jetted tub, and his/hers raised vanities. Two additional oversized guest suites on the 2nd floor each feature a full bath. Outdoor living is elevated with a courtyard, paved & covered patio, heated pool/spa, and low-maintenance landscaping. A paver driveway and epoxy garage, complete this exquisite property. Enjoy Windsong's amenities: a lakefront clubhouse & pool, kiddie pool & water park, playground, kayaks & paddleboards, and a pontoon boat for the Winter Park Chain of Lakes. Proximity to top-rated schools, Park Avenue, local restaurants, and shopping.

A NEWLY RENOVATED, FOUR bedroom/2 bath POOL home in Winter Park! This lovely ranch style house offers lots of pleasant surprises from the brand new roof to the beautiful wood-look ceramic tile floors. As you arrive at the paver driveway, and step inside through the front door entry, notice the open floor plan and gorgeous updated kitchen. Continue to roam through the house and observe the many upgrades including a fully renovated primary and hallway bath. Meander out to the back of the house and catch a glimpse of the screened patio extension, huge private back yard, and the fabulous in ground pool complete with a large pavered sundeck. This delightful home can also be leased furnished for an increased monthly rental amount. Conveniently located near Advent Health Winter Park, Phelps Park, Winter Park YMCA, Park Avenue, and Interlachen Country Club. Call for your showing appointment today!

A wonderful opportunity to live in the Heart of Winter Park with walking distance to Lakemont Elementary, Phelps Park, YMCA, Sprouts Farmers Market and lot's of great Restaurants. Popular Park Avenue is less than a 10 minute drive. This adorable updated 3 bedroom, 2 bath, plus sunroom home is so charming with Beautiful (original) hardwood floors throughout. The kitchen was opened up several years ago and is equipped with soft close white cabinets, granite countertops, SS appliances and a spacious walk in pantry. The Florida/Sunroom has an array of windows and opens to the large backyard. Many updates have been done over the years including kitchen & baths, windows, re-pipe, new window treatments, alarm system, outdoor speakers, painted inside and out, new hardware on all doors & kitchen cabinets, new washer & dryer, new disposal and a new roof (2021). This home has an FHA mortgage which your buyer may be able to assume. The interest rate is 2.25%. Buyer would have to come up with the difference between the sales price and loan amount and qualify for the loan. The current loan amount is approximately $308,000.

STUDIO CONDO LOCATED IN WINTER PARK PERFECT FOR SOLO LIVING OR FOR COUPLES. GROUND FLOOR UNIT WITH 549 SQFT. HAS A COMBO LIVING AREA/BEDROOM WITH NEW KITCHEN CABINETS AND GRANITE. COMMUNITY OFFERS A POOL WITH A DOG PARK. CALL WITH ANY QUESTIONS.

Welcome to the heart of Winter Park! This beautiful first floor condo is located in one of the town's most iconic buildings, Park Aire. Nestled between the famous Winter Park Golf Course and downtown area where shopping and dining are a must! Other close by attractions include, the Morse Museum, Central Park, Hannibal Square and Scenic Boat Tours. This updated condo features beautiful wood floors, updated kitchen, and nice view from oversized windows. Park Aire has a beautiful private pool area and lush garden area as well as reserved underground parking. This is a great opportunity to live on one of the most well known streets in Central Florida! Call for your showing today!

Beautiful newly built corner unit townhome, located in the heart of Winter Park. This open floor plan will please the most demanding resident. Enjoy natural light throughout every room and notice the MODERN DESIGN and UNIQUE FINISHES. Elegant GOURMET kitchen with STAINLESS STEEL appliances, WALK-IN pantry, DESIGNER soft-close WOOD CABINETS, easy-care QUARTZ COUNTER-TOPS in Kitchen & Bathrooms. The New Cairo oak wide plank wood flooring throughout the home and carpeted bedrooms upstairs provide comfort and style. Every bedroom includes an extended closet and is custom-made California Closets in the Main suite. Wide alley grey paver driveway, attached two-car garage with windows, and street parking. Control your daily air conditioning needs from your smartphone with your fully programmable Nest Thermostat. LOCATION AT ITS BEST!!! You are minutes away from downtown Winter Park and Park Avenue's unique shopping with local and international restaurants, nearby Rollins College, Winter Park Tennis Courts, and many parks to enjoy the outdoors. This WELL-MAINTAINED COMMUNITY is surrounded by beautiful MATURE LANDSCAPING and TREES providing a lush canopy of greenery, which is both aesthetically gorgeous. Within biking distance to the unique eateries, upscale shopping, and exciting cultural activities of PARK AVENUE and WINTER PARK VILLAGE, you can immerse yourself into the full Winter Park lifestyle right away. In addition to your opulent dining and shopping options, you're only a short drive from Orlando Museum of Art, Orlando Science Center, Dr. Phillips Center for the Performing Arts, Audubon Park Garden District, Leu Gardens, and Downtown College Park. Also, just minutes from Advent Health Hospital, Rollins College, Amway, Sunrail, Orlando City Stadium, I-4, and 408. Stay active and enjoy a morning walk/run or bicycle ride on the nearby Cady Way Trail. For art lovers, marvel at all the treasures and artworks featured at the world-famous Winter Park Art Festival. Washer and dryer are present but in as/is condition and for tenant convenience only. Small pets allowed (2 pet max, 40lb weight limit) with approval, additional pet fee per pet, and additional security deposit per pet. There is also an additional $20 pet application fee for the first pet, $15 for the second pet. Please review our full pet policy here: https://rentcare.petscreening.com/**FIVE STARS ***** RESIDENTS BENEFIT PACKAGEResidents are enrolled in the Resident Benefits Package. There is an additional $35.00 a month charge for this added to the advertised rent and is considered additional rent. This (RBP) includes HVAC air filter delivery, utility concierge services making utility connection a breeze during your move-in, our best-in-class resident rewards program, and much more! More details upon application.**RENTERS INSURANCE REQUIRED

LOCATION! LOCATION! LOCATION! - WINTER PARK, the most desirable area in Central Florida. GATED NEW community HAWK'S CREST, Three bedroom townhome in a gated community with swimming pool, playground and park.

Beautiful Winter Park 3 Bedrooms, 2.5 Bathrooms, Eat-In Kitchen and Spacious Loft/Office Area. [Pictures taken when house was vacant. TENANT OCCUPIED, 24 Hour Notice, Appointment Only. Available to move in December 15th 2023.] Enjoy the Screened in Patio through the French Doors. Cozy Fireplace in the Family Room with Vaulted Ceilings. Enjoy walking on the winding sidewalk in Autumn Glen's Lakeside Park with a Lovely Gazebo, Mature Trees, Tennis Courts, two lighted Fountains on the Lake and a Playground. Nice neighborhood close to Shopping, Red Bug Lake Park and Cross-Seminole Trail. The Greenway (417) is convenient, just over 2 miles.

Welcome to the exclusive gated community, Meadows at Hawk''s Crest, located in sought-after Winter Park northeast of Orlando. Beautiful water view at the back patio. There are two master bedrooms, one in the main first floor and another master bedroom and 2 bedrooms on the second floor. High ceiling in the family room. One bonus office downstairs. Gated community lawn care is included

Stop Looking!!! Gorgeous and Fully updated two-bedroom, two-story condo with spacious fully fenced backyard! Yes, Condo with backyard and screened lanai in Highly desired Winter Park area. Zoned for top-rated schools and just minutes from UCF, Full Sail, and Downtown Orlando! Condo is a very well maintained condo.Kitchenupdated with granite counter tops and stainless steel appliances.You will find additional dining space in the living/dining room combo!Step out back and enjoy the spacious screened lanai!The upstairs boasts two enormous bedrooms with nice closet space, a full bath with extended granite vanity, and extra linen storage in the hallway!Main bedroom featuresa screened-in BALCONY and Walk- in closet.Exterior features include an oversized carport with spacious storage unit.Great condo for owner occupantor investment property!

Welcome to 2139 Blossom Lane, where you have the rare opportunity to build your Winter Park dream home on the Lake Killarney canal. The lot boasts an impressive canvas of 19,833 square feet (~.46 acre), more than enough space for even the largest of visions to come to life. Minutes away from dining & shopping at the Winter Park Village, Ravadauge & Park Avenue. Take your boat to Hillstone for dinner and enjoy the sunset on the 234 acre private Lake Killarney. The canal also features a large turnaround at the end for easy access in and out. 100 feet wide at the street & over 60 feet of canal frontage. The neighborhood is lined with some of Winter Park's finest homes & only has one way in and one way out. No through traffic. Survey available. Open to seller/owner financing.

THIS GORGEOUS 2 BED/2.5BATHS MID-CENTURY MODERN ARCHITECTURALLY DESIGNED SINGLE FAMILY HOME IS NEWLY REMODELED AND NESSELED IN WINTER PARK COMMUNITY OF HIDDEN OAKS. THIS ELEGANT HOME FEATURES 1,031 SQ. FT. OF LIVING SPACE, A MODERN SWEDISH KITCHEN FEATURING CRYSTAL COUNTER TOPS WITH FUNCTIONAL DRAWERS, PORCELEN TILE FLOORS. STAINLESS STEELE APPLIANCES INCLUDE RANGE, RANGE HOOD, REFRIGIRATOR AND MICROWAVE/CONVECTION OVEN. BEAMED CIELING THAT FLOWS TO THE BEAUTIFUL LAMINANTE WOOD FLOORS. LOVELY DESIGNED MASTER AND QUEST BATHROOMS WITH STAINLESS STEELE FIXTURES AND WOOD LAMINATE CIELING FANS IN MASTER BEDROOM, LIVING ROOM AND FAMILY ROOM. BRAND NEW ROOF 2023, NEW 40 GALLON HOT WATER HEATER IN THE GARAGE. UPDATED PLUMBING, NEW ELECTRICAL PANEL AND UPDATED AC HANDLER, CONDENSER AND NEW AIR DUCTS. WONDERFULLY LANDSCAPED TO GIVE ULTIMATE CURB APPEAL. THIS HOME IS 10 MINUTES FROM DOWNTOWN ORLANDO, 15 MINUTES TO ORLANDO INTERNATIONAL AIRPORT, 10 MINUTES TO RETAIL SHOPPING AND RESTUARANTS, 15 MINUTES TO VALENCIAL STATE COLLEGE, 25 MINUTES TO UCF AND 30 MINUTES TO DISNEY WORLD.

Fractional Ownership. CUL-DE-SAC TUCKED AWAY PRIVATE POOL HOME OASIS IN THE MIDDLE OF EVERYTHING, WITH AN ENTERTAINING OPEN FEEL, STAINLESS APPLIANCES AND TILE THROUGHOUT YOU HAVE FOUND YOUR NEW HOME. A LARGE FENCED IN BACKYARD WITH POOL AND A LARGE ENTERTAINING FAMILY ROOM ACCESS DOOR OPEN UP AND ENTERTAIN IN BOTH AREAS. THE LARGE SCREENED IN COVERED FRONT PORCH GIVES YOU ANOTHER AREA TO SIT BACK AND RELAX AFTER DINNER ON IN THIS PRIVATE CUL-DE-SAC SETTING. All information recorded in the MLS is intended to be accurate but cannot be guaranteed. Buyers should independently verify all measurements, fees & policies, restrictions, leasing restrictions, taxes, schools, flood zones along with other features and details as considered part of the buyers due diligence and inspection. ALL PURCHASE OFFERS SHOULD BE ON LATEST AS-IS CONTRACT, ACCOMPANIED WITH PROOF OF FUNDS FOR CASH DEALS AND FINANCING APPROVAL LETTER WITH PROOF OF FUNDS FOR DEPOSIT AND CLOSING FUNDS NEEDED AS WRITTEN ON CONTRACT OFFER TO BE CONSIDERED A VALID OFFER TO PRESENT TO OWNERS.