Winter Park FL Real Estate & Homes for Sale

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Beds:
5
Baths:
4.00
Sq.Ft.:
3,164
Status:
NEW LISTING
MLS#:
O6371649
Type:
Single Family
Subdivision:
Lawndale
Lot size:
0.16 Acres
Year built:
2026
A broker reciprocity listing Courtesy: CHARLES RUTENBERG REALTY ORLANDO 407-622-2122
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ADDITIONAL INFORMATION

Under Construction. UNDER CONSTRUCTION. This 3,164 sq ft new construction home at 1523 Miller Ave, Winter Park, FL 32789 combines modern design, high-end finishes, and an unbeatable central location. Featuring 5 bedrooms, 4 full bathrooms, and a private salt-water pool, the home is designed for both everyday comfort and effortless entertaining. The open L-shaped living, kitchen, and dining area is filled with natural light and anchors the main level, creating a seamless flow ideal for hosting or relaxing. The chef’s kitchen overlooks the living space and extends outdoors to a covered back patio with a fully equipped outdoor kitchen complete with grill, sink, and wine fridge, perfect for Florida living year-round. Additional highlights include a shingle roof with metal accents, a pergola accenting the front of the garage, and clean architectural lines that elevate the curb appeal. The floor plan offers flexibility with generous bedroom sizes and well-appointed full baths, while the backyard retreat centers around the sparkling salt-water pool. Location is a major advantage—2 minutes to I-4, 4 minutes to Mills Avenue, 5 minutes to Park Avenue, 10 minutes to Downtown Orlando, and approximately 20 minutes to Disney, placing dining, shopping, nightlife, and major employers all within easy reach. A rare opportunity to own a brand-new construction home in one of Winter Park’s most connected neighborhoods.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,546
Status:
NEW LISTING
MLS#:
O6371239
Type:
Single Family
Subdivision:
Autumn Glen
Lot size:
0.14 Acres
Year built:
1986
A broker reciprocity listing Courtesy: RE/MAX TOWN & COUNTRY REALTY 407-695-2066
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ADDITIONAL INFORMATION

One or more photo(s) has been virtually staged. Location is Everything. If you want the best home in the best location look no further. This three bedroom two and half bathroom home is located in the much desired Autumn Glen community. The home is perfect and has a very flexible floorplan with the 3rd bedroom currently configured as a loft with a closet for the work from home person and can be easily converted to a third bedroom if needed. The first floor features a spacious dining area and a step down into a large living room with sliders to pool and patio. The gourmet kitchen with eating space includes upgrades like Custom cabinets, Stainless appliances , reach in pantry breakfast bar and tile flooring all overlooking the living/dining area. The primary suite is located downstairs and features a walk in closet with hidden storage access under the stairs, updated primary bath with with upgraded vanity, custom lighting and garden tub. Upstairs features a large guest bedroom, updated guest bath and the loft than can easily converted to a third bedroom. Some of the updates on this home include, Newly painted interior, home has been replumbed and newer roof. Moving outside to the beautiful open air pool with spill over spa framed with tropical palm trees, banana tree, custom deck, additional storage shed, updated landscaping and all this surrounded by a fully fenced yard. The fenced yard provides privacy and room to enjoy the outdoors. The community is located just around the corner from Red Bug Elementary, Tuskawilla Middle and Lake Howell High School.. Other community features include tennis/pickleball courts, a playground, and a gazebo overlooking the community pond—perfect for bringing your fishing pole. If you're looking for the right house in the right location, this is the one. Autumn Glen is ideally located just around the corner from Red Bug Elementary, Tuskawilla Middle, and Lake Howell High School. Community amenities include tennis and pickleball courts, a playground, and a gazebo overlooking the community pond—perfect for relaxing or casting a fishing line. If you’re looking for the right home in the right location, this is the one.

Beds:
1
Baths:
1.00
Sq.Ft.:
803
Status:
NEW LISTING
MLS#:
O6371260
Type:
Condo
Subdivision:
Colonies
Lot size:
10.07 Acres
Year built:
1974
A broker reciprocity listing Courtesy: JOHN SILVA REALTY & ASSOCIATES 407-420-7908
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ADDITIONAL INFORMATION

GREAT INVESTMENT OPPORTUNITY: Completely remodeled and move-in ready, this beautiful 1-bedroom, 1-bathroom condo in Winter Park offers the perfect blend of comfort, convenience, and value. Located just 11 minutes from Orlando International Airport and close to UCF, Full Sail University, shopping malls, restaurants, major highways, and popular theme parks, this home is ideal for both homeowners and investors. The condo features brand new kitchen countertops and cabinets, giving it a fresh, modern look throughout. Whether you're searching for an affordable place to call home or a great addition to your rental portfolio, this unit is a fantastic option. Enjoy easy access to the community pool just a short walk away, and take advantage of the prime location within short distance to Target, local dining spots, and even a Twistee Treat. With so much to offer and tons of potential, this gem won’t last long, schedule your showing today!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,572
Status:
NEW LISTING
MLS#:
O6371341
Type:
Single Family
Subdivision:
Albert Lee Ridge First Add
Lot size:
0.17 Acres
Year built:
1956
A broker reciprocity listing Courtesy: OPENDOOR BROKERAGE LLC 480-462-5392
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ADDITIONAL INFORMATION

One or more photo(s) has been virtually staged. Welcome to 958 Dupont Ave, a home that exudes charm and functionality. The kitchen is a chef's dream, boasting stainless steel appliances that add a sleek, modern touch. Step outside to a spacious, fenced-in backyard, perfect for privacy and outdoor activities. Enjoy leisurely afternoons or entertain guests on the covered patio, a delightful extension of the living space. A storage shed provides ample room for your tools and outdoor equipment. Inside, fresh interior paint gives the home a clean, updated feel. This property is a perfect blend of comfort and convenience, waiting for you to make it your own.. Included 100-Day Home Warranty with buyer activation

Beds:
4
Baths:
3.00
Sq.Ft.:
2,058
Status:
NEW LISTING
MLS#:
O6371014
Type:
Single Family
Subdivision:
Bear Gully Forest
Lot size:
0.53 Acres
Year built:
2003
A broker reciprocity listing Courtesy: ADVANCE REALTY & MANAGEMENT LLC 407-901-3636
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ADDITIONAL INFORMATION

Spacious Winter Park home on over a half acre with no rear neighbors!. In Bear Gully Forest community and has over 2,000 s/f- with a Living Room, Dining Room, Eat-in Kitchen and more. The home's fully-equipped kitchen has excellent cabinet space and appliances that include a stove, microwave, and dishwasher. An inside laundry room has a washer/dryer combination for your convenience. Bedroom with 1/2 bath upstairs. Roof new in 2018 with a 10 year full warranty.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,900
Status:
NEW LISTING
MLS#:
O6370558
Type:
Condo
Subdivision:
Whispering Waters/phillips Circle Rep
Year built:
1960
A broker reciprocity listing Courtesy: FANNIE HILLMAN & ASSOCIATES 407-644-1234
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ADDITIONAL INFORMATION

Enjoy the Winter Park lifestyle in this spacious 2-bedroom, 2-bath lakefront condo offering 1,900 square feet in the heart of downtown Winter Park. Enjoy serene lake views from the 120 sq ft screened porch—perfect for morning coffee or evening wine. The light-filled living area features soaring 8 ft 10 in ceilings, creating an open, airy atmosphere. A cozy family room offers built-in shelving and a wet bar, ideal for relaxing or entertaining. The galley kitchen features granite countertops, a natural gas range, and a convenient laundry closet with a stackable washer and dryer. The primary bedroom boasts a walk-in closet with ample storage, additional drawers and cabinets in a rear alcove, and a primary bath with dual sinks and a walk-in shower. The secondary bedroom includes an adjoining office alcove, while the secondary bath offers a tub/shower combination. Neutral tones flow throughout the condo, and the dinette provides beautiful views of Lake Osceola. Completely rebuilt in 2011 with new plumbing, electrical wiring, air conditioning, and ductwork, this home offers modern efficiency and peace of mind. A covered boat slip (#15) with lift, two covered parking spaces in the underground garage, approximately 90 sq ft of private utility storage, and a community pool complete this exceptional offering. Just steps from Park Avenue, enjoy walkable access to premier shopping, dining, museums, and seasonal events, making this a rare opportunity for true lakefront living in one of Winter Park’s most desirable locations.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,290
Status:
NEW LISTING
MLS#:
O6370723
Type:
Single Family
Subdivision:
Magnolia Gardens Sub
Lot size:
0.14 Acres
Year built:
1954
A broker reciprocity listing Courtesy: OUTLET REALTY 407-353-5518
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ADDITIONAL INFORMATION

NEW CONSTRUCTION–QUALITY WALKABLE WINTER PARK FULL SMART HOME This is not a renovation—this is a complete architectural transformation. Taken down to the studs and roofline, expanded, and rebuilt with intention, this custom luxury residence is ideally located just steps from Winter Park Village and minutes from iconic Park Avenue, offering a truly walkable, car-optional lifestyle. The home features a custom 51’ x 10’ driveway, mature Italian cypress trees, sculptural landscape elements, and elegant iron railing, creating exceptional curb appeal. Covered front and side porches welcome you into a thoughtfully designed interior blending contemporary architecture with refined mid-century influence. Over 300 square feet of newly added living space includes two additional bathrooms, an indoor laundry room, and an oversized primary suite designed as a private retreat. Custom liner windows in the dining room and primary suite provide abundant natural light and architectural character. Interior highlights include: • Tile flooring throughout with custom tile work • Designer kitchen with floating shelves • Smart stove, built-in under-counter microwave and dishwasher • LED under-cabinet and island lighting • Custom light fixtures and ambient lighting throughout • Primary bath with ceiling-mounted rain shower • Zebra blinds throughout • New stacked washer and dryer included The home is fully equipped with modern smart-home technology, including: • New AC system with smart thermostat • Tankless water heater and all-new plumbing • Smart lock entry • Smart soffit exterior lighting • Google doorbell camera and security floodlight cameras with two-way audio • Smart sprinkler system with weather monitoring The private backyard is enclosed with PVC privacy fencing and designed for outdoor living, featuring a porcelain-tiled covered patio and a separate poured slab ideal for a fire pit or grilling area, positioned safely away from the home. Enjoy unmatched proximity to dining, shopping, entertainment, parks, golf, train station, and everyday conveniences including Starbucks, Whole Foods, Publix, restaurants, and movie theater—all just moments away. Homes offering new-construction quality, designer finishes, smart-home integration, and this level of walkability rarely come to market. A turnkey opportunity for the most discerning buyer.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,755
Status:
NEW LISTING
MLS#:
O6370721
Type:
Townhouse
Subdivision:
Enclave At Hawks Crest
Lot size:
0.06 Acres
Year built:
2021
A broker reciprocity listing Courtesy: U S GLORY REALTY 407-222-7801
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ADDITIONAL INFORMATION

Welcome to this fabulous townhome in the much sought after Hawk's Crest neighborhood in winter park. The townhouse has perfect layout when you walk into the house, beautiful tile floor, one half bathroom downstairs. 3 Bedrooms upstairs with a big loft. It is a perfect floor plan to live here or as an investment. Resort style pool and playground. Near to everywhere, easy to find highway and shopping center.

Beds:
1
Baths:
1.00
Sq.Ft.:
645
Status:
NEW LISTING
MLS#:
V4946519
Type:
Condo
Subdivision:
Lakeside Manor Apts Condo
Lot size:
0.1 Acres
Year built:
1969
A broker reciprocity listing Courtesy: LPT REALTY LLC (DB) 877-366-2213
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ADDITIONAL INFORMATION

Welcome to lakeside living! This cozy one-bedroom, one-bathroom condo offers a blend of amenities and convenience. This perfectly located condominium has low HOA FEES and has no assessment fees! Enjoy your days fishing, boating, or hanging out by the pool overlooking gorgeous Lake Killarney, a 240 acre spring-fed lake! Cherish living on the shores of Lake Killarney, complete with coveted dock access and a refreshing pool. Located in the heart of Winter Park, one of the most sought-after zip codes in the Orlando metro area. Residents in the desirable Lakeside Manor community enjoy access to the boat slips, the clubhouse, the lakefront pool and the beautifully maintained landscaped courtyard. Bring your ideas and make this your own. HOA fees includes ground keeping, exterior and roof maintenance. Water is also included with a low monthly HOA fee of $240 a month. HVAC 2021 , Roof 2016, Conveniently located near I-4 for quick access to Orlando. Situated near Winter Park Village, College park and Baldwin Park. Appreciate the nearby hospitals, shopping, dining, museums, parks, botanical gardens and entertainment of Winter Park. Savor your lakeside retreat with low fees and low maintenance. All information deemed reliable but not guaranteed and should be independently verified. If qualified with preferred lender, a $1500 credit will be offered.

Beds:
4
Baths:
3.00
Sq.Ft.:
1,526
Status:
NEW LISTING
MLS#:
S5140952
Type:
Single Family
Subdivision:
Winter Park Estates
Lot size:
0.25 Acres
Year built:
1961
A broker reciprocity listing Courtesy: MY REALTY GROUP, LLC. 786-847-7421
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ADDITIONAL INFORMATION

Experience luxury living in this stunning, remodeled single-family home located in the heart of Winter Park. This spectacular residence features four spacious bedrooms and three modern bathrooms, boasting sleek laminate flooring throughout. The chef-inspired kitchen comes fully equipped with premium stainless steel appliances, while the massive backyard and sparkling pool provide an ideal setting for family gatherings and outdoor entertainment. Nestled in a prime location, this property provides the perfect blend of suburban tranquility and urban convenience. Residents enjoy proximity to schools and sit just minutes from the iconic Park Avenue shopping district. Whether commuting via the 436 or visiting local favorites like the Winter Park Farmer’s Market, everything you need remains right at your doorstep—the ultimate choice for the best of Central Florida living

Beds:
3
Baths:
2.00
Sq.Ft.:
1,803
Status:
NEW LISTING
MLS#:
O6370332
Type:
Single Family
Subdivision:
Kenilworth Shores
Lot size:
0.21 Acres
Year built:
1962
A broker reciprocity listing Courtesy: FANNIE HILLMAN & ASSOCIATES 407-644-1234
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ADDITIONAL INFORMATION

C H A R M I N G INSIDE & OUT! Delightful curb appeal & quaint front porch welcome you HOME! Move right into this ONE STORY immaculate & charming home on a beautiful tree-lined street in Winter Park. You will be enthralled with the hardwood floors, crown molding, amazing floor plan & tons of natural light! Spacious living room with bay window leads to dining room with original built-ins & french pocket doors invite you into family room with cozy fireplace. Updated kitchen boasts white cabinets, stone counters, stainless steel appliance & a cozy breakfast nook with french doors leading to open patio & serene, fenced backyard. Lovely primary bedroom offers renovated ensuite bath. Extras include: Oversized 2 car garage, Brookshire Elementary, Glenridge Middle & Winter Park High, ROOF 2021. NEW PLUMBING 2023. NEW DUCTWORK 2023. NEW ELECTRIC PANEL 2023. NEW INSULATION 2023. PRIMARY BATH RENOVATED 2024. NEW GUTTERS & LEAF-GUARDS 2024. NEW LAWN & LANDSCAPE 2024. IRRIGATION AUTOMATION 2024. WELCOME HOME!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,624
Status:
NEW LISTING
MLS#:
O6370371
Type:
Single Family
Subdivision:
Garden Lake Estates Unit 3
Lot size:
0.27 Acres
Year built:
1983
A broker reciprocity listing Courtesy: FLORIDA PRESTIGIOUS HOMES INC 754-246-2070
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ADDITIONAL INFORMATION

Welcome to this beautifully updated 3-bedroom, 2-bath home with a screened-in pool, ideally located in the heart of Winter Park. Step inside to a fresh, move-in-ready feel with new flooring throughout, new light fixtures, new windows, and new doors—all thoughtfully selected to give the home a clean, modern look. The open, inviting layout is perfect for everyday living and entertaining, and the screened pool area creates a private Florida retreat for relaxing weekends, family gatherings, or evening swims—without the bugs. Conveniently close to Winter Park’s shopping, dining, parks, and local favorites, this home offers the best of Central Florida living in a prime location. More photos coming soon—don’t miss your chance to see this one!

Beds:
3
Baths:
5.00
Sq.Ft.:
4,237
Status:
NEW LISTING
MLS#:
O6370317
Type:
Townhouse
Subdivision:
Park Hill
Lot size:
0.07 Acres
Year built:
2019
A broker reciprocity listing Courtesy: COLDWELL BANKER RESIDENTIAL RE 407-647-1211
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ADDITIONAL INFORMATION

A refined, custom brownstone with an exclusive Park Avenue address, offering an unparalleled Winter Park lifestyle enhanced by the finest designer selections throughout. The timeless brick elevation and expansive windows evoke the charm of a favorite city street while preserving the tranquility of this sought-after setting. This three-story townhouse offers 4,237 square feet of thoughtfully designed living space, featuring three en-suite bedrooms, three full baths, two half baths, and a private elevator. Offered fully furnished for the most discerning buyer, the residence welcomes you through a hand-forged iron gate, gas lanterns, and a brick walkway. The open living, dining, and kitchen areas are ideal for entertaining and flow seamlessly to a private open-air courtyard filled with natural light. Custom lighted built-ins with glass shelving, an entertainment bar, and an antique glass entertainment center with sliding doors allow the space to beautifully showcase art or conceal the television. Designer window treatments include exquisite drapery and plantation shutters, complemented by beautiful backsplashes, countertops, fine wallpaper, and detailed trimwork throughout. An exquisite lighting package features designer fixtures and ambient lighting. The chef’s kitchen is equipped with Wolf and Sub-Zero appliances, a center island with ample prep and serving space, and a walk-in pantry, blending perfectly with the dining area and courtyard for effortless entertaining. The private primary suite is appointed with a morning station, dual closets, and a luxurious bath featuring floor-to-ceiling windows, double marble vanities, a spacious glass-enclosed steam shower, and a luxury bathtub. The intimate third-floor rooftop terrace offers a gathering space and exterior half bathroom for convenience. Additional features include a Control4 home automation system, an upscale air-conditioned garage with ceiling storage and custom cabinetry, newer third-floor HVAC and condenser, newer mini-split in the upstairs exterior bath, three-story block construction with soundproof floors, five AC units, and three tankless gas water heaters.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,010
Status:
Active
MLS#:
O6369943
Type:
Condo
Subdivision:
Woodcrest Condo
Lot size:
0.81 Acres
Year built:
1969
A broker reciprocity listing Courtesy: OLYMPUS EXECUTIVE REALTY INC 407-469-0090
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ADDITIONAL INFORMATION

Opportunity property in the heart of Winter Park. Welcome to 1920 Woodcrest Drive, Unit 9, a 2 bedroom, 2 bathroom condo that has been fully gutted and is ready for a buyer with vision. This is a true blank canvas for a discerning owner occupant who wants to curate a space to their personal taste, or an investor seeking a value add renovation in a highly desirable area. Minutes from Baldwin Park and close to Park Avenue’s renowned shops and dining, with access to A rated schools. One assigned parking space included. Shared common laundry on site. Bring your designer and contractor and create something exceptional.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,470
Status:
Active
MLS#:
O6369653
Type:
Single Family
Subdivision:
Windsong-knowles Place
Lot size:
0.26 Acres
Year built:
2014
A broker reciprocity listing Courtesy: SELECTIVE REALTY GROUP LLC 407-627-1727
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ADDITIONAL INFORMATION

Welcome home to the prestigious community of Windsong in Winter Park. Upon entering this Toll Brothers-built home, you will notice no detail has been spared. Soaring ceilings greet you as you enter the foyer with elegant lighting. This 4-bedroom, 3.5-bath home is loaded with upgrades. The office features beautiful wood and detailed, custom bookshelves, complete with a double-door entry for added privacy. The formal dining room features a pass-through to the Butler's Pantry, which leads into a chef's oasis—Wolf stainless steel appliances for the serious chef, and solid surface countertops. The gourmet kitchen opens up to the family room. This home is a Great floor plan for entertaining friends and family. Eat in nook is located off the kitchen for dinners together. The primary suite is located on the first floor with a spa-like ensuite. Double vanity, extra-large shower, large bathtub for when a relaxing bath is just what you need after a long day. Upstairs, you will find a bonus room, as well as the remaining bedrooms. off the bonus room is a bedroom and a full bathroom, great for guests. The other two bedrooms and bathroom are located on the opposite side of the upstairs to create a split floor plan. Large backyard for enjoying the Florida weather. New EV charger in garage, new A/C unit. Home includes surround sound. This home features numerous upgrades, too many to list. Windsong community offers a resort-style pool with lake views, a playground, lake for fishing. Close to restaurants, schools, and shopping.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,584
Status:
Active
MLS#:
O6369603
Type:
Single Family
Subdivision:
Temple Terrace
Lot size:
0.3 Acres
Year built:
1978
A broker reciprocity listing Courtesy: GENSTONE REALTY 407-237-0905
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ADDITIONAL INFORMATION

Welcome to this classic ranch home offering 3 bedrooms, 2 baths, and a wonderfully livable floor plan designed for everyday comfort, work-from-home flexibility, and easy entertaining. With 1,584 sqft of living space this home lives large and offers generous room sizes, plenty of storage, and a layout that simply makes sense. From the big front patio, step inside to a bright living area with cathedral ceilings and natural light, leading into an updated kitchen featuring granite countertops and newer cabinetry. Stacked bedroom layout, and the bathrooms feature tile finishes and oak cabinetry. Flooring includes tile throughout most of the home, wood laminate in the primary bedroom, and carpet in two bedrooms. The home also features updated double-pane insulated windows. Some of the highlights of this home are the expansive screened-in Florida room, perfect for relaxing, dining outdoors, or hosting friends —while enjoying fresh air. Outside, you'll find a huge, fully fenced backyard with mature oaks, palms, bananas, flowering cactus, and an aloe garden. There’s ample room for a pool, future expansion, and RV / trailer storage. A storage shed with electric adds even more convenience. The location truly can’t be beat — centrally located near downtown Winter Park, Maitland, Casselberry, restaurants, theaters, lakes, bike paths, museums, five golf courses, and endless shopping and recreation. Zoned for highly regarded schools including Dommerich Elementary, Maitland Middle, and Winter Park High, this is a setting many buyers specifically seek out. The neighborhood is on city utilities; this home currently uses septic which may not function properly and may need to be connected to city sewer which is already on the street. This is a conventional and cash-only sale and is being offered As-Is, with buyers responsible for their due diligence including verifying fees, taxes, and property details.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,197
Status:
Active
MLS#:
O6369571
Type:
Single Family
Subdivision:
Pinewood Sub
Lot size:
0.19 Acres
Year built:
1947
A broker reciprocity listing Courtesy: KELLER WILLIAMS REALTY AT THE PARKS 407-629-4420
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ADDITIONAL INFORMATION

Income-producing home with a detached in-law apartment in a prime central Orlando location — ideal for a house hack, long-term rental, or short-term rental (Airbnb allowed). The main house is a two-bedroom, one-bath residence, while the in-law apartment is a completely detached one-bedroom, one-bath unit with separate entrances and separate mailboxes, offering excellent privacy and flexibility. The in-law apartment is currently rented for $1,350/month on a month-to-month lease, providing immediate income and flexibility. The main house was previously rented for $1,850/month, demonstrating strong and proven rental history. Live in one unit and rent the other, or rent both for attractive cash flow. The main home is well maintained with neutral finishes, updated flooring, modern lighting, and a functional layout filled with natural light. A spacious deck and outdoor area provide excellent separation and privacy between the main house and the in-law unit. Major updates include a roof approximately 11 years old, HVAC approximately 6 years old, copper plumbing, and a septic system recently pumped and in great condition. A 4-point inspection is available upon request. Conveniently located minutes from Winter Park, College Park, Downtown Orlando, major hospitals, dining, I-4, International Drive, and Orlando International Airport. A rare opportunity offering location, flexibility, and multiple income strategies.

Beds:
4
Baths:
4.00
Sq.Ft.:
2,540
Status:
Active
MLS#:
O6369267
Type:
Single Family
Subdivision:
Temple Estates
Lot size:
0.19 Acres
Year built:
1952
A broker reciprocity listing Courtesy: PREMIER SOTHEBY'S INTL. REALTY 407-644-3295
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ADDITIONAL INFORMATION

In the heart of Winter Park, this extensively renovated modern farmhouse offers exceptional value for the location. A circular drive and inviting front porch welcome you into light-filled living spaces enhanced by all-new energy-efficient windows, custom millwork and designer finishes throughout. The functional layout includes a first-floor guest suite, additional well-appointed bedrooms and updated baths. The kitchen opens seamlessly to the dining and family rooms, featuring custom cabinetry, stone countertops, stainless appliances, walk in pantry and built-in wine area. The family room flows to a covered lanai and summer kitchen, overlooking a paver deck, pool, fire pit and putting green, ideal for year-round entertaining. The fully fenced backyard offers privacy and access to a detached garage with additional storage. Upstairs, the primary suite features a private balcony, a sitting area, a walk-in closet, and a spa-inspired bath with a freestanding tub and an oversized shower. An additional upstairs fourth bedroom ensuite, currently used as a gym, offers flexibility for a home office or nursery. Renovated with quality and intention, including updated systems and recent roofs. Ideally across from Phelps Park and just a few blocks from Interlachen Country Club and the Winter Park Racquet Club.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,117
Status:
Active
MLS#:
O6369034
Type:
Townhouse
Subdivision:
Hidden Oaks Condo Ph 10
Lot size:
2.13 Acres
Year built:
1984
A broker reciprocity listing Courtesy: SPRINGHILL PROPERTIES LLC 646-236-0299
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ADDITIONAL INFORMATION

Excellent opportunity to acquire a 3-bedroom, 2-bath first-floor end-unit condo offering approximately 1,117 sq ft in a well-established community. The unit features a functional layout and a highly desirable location near UCF, Full Sail University, Valencia College, and major shopping and dining. Priced to sell, this property is ideal for investors seeking a light-to-moderate rehab with strong rental or resale potential, or for a first-time buyer looking to add value. Schedule a showing today and capitalize on this opportunity.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,548
Status:
Active
MLS#:
R11149335
Type:
Townhouse
Subdivision:
Winter Green
Lot size:
0.04 Acres
Year built:
1987
Courtesy: Compass Florida LLC 561-270-5384
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ADDITIONAL INFORMATION

The perfect hideaway home, nestled in the oaks, in coveted and charming Winter Park. Get the ''small-town'' feel, close to all the dynamic, high-energy Orlando has to offer. Your key gateway and home base to picturesque Central Florida. This versatile 2-story end-unit townhouse in a park-like setting lives like a single-family home. Privacy galore. It will appeal not just to 'Orlandoans' but also to snowbirds seeking Florida residency, investors, and South Floridians seeking a weekend retreat. Yes, the high-speed Brightline rail runs between Orlando and Miami. The 3rd bedroom features a loft/home-office design with custom cabinetry and a Murphy bed. Low-maintenance and pet-friendly lifestyle. You're home! Park, and enter your front door. Come and go at leisure without seeing a doorman.

Beds:
1
Baths:
1.00
Sq.Ft.:
645
Status:
Active
MLS#:
O6368580
Type:
Condo
Subdivision:
Lakeside Manor Apts Condo
Lot size:
0.04 Acres
Year built:
1969
A broker reciprocity listing Courtesy: HOMESMART 407-476-0451
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ADDITIONAL INFORMATION

Welcome to your next chapter of lakeside living! This charming one-bedroom, one-bathroom condo offers a perfect blend of tranquility and convenience in the heart of Winter Park. Step inside to discover a thoughtfully designed space where comfort meets style. The open-concept living area welcomes you with beautiful engineered wood floors, creating a seamless flow between the living room and kitchen. Natural light streams through the windows, highlighting the warm and inviting atmosphere throughout.Your private bedroom retreat features a generously sized closet, making storage a breeze. The well-appointed bathroom complements the living space perfectly. What truly sets this home apart is its privileged location near Lake Killarney, a stunning 239-acre spring-fed lake that serves as your backyard oasis. As a resident, you'll enjoy exclusive access to on-site boat slips, a launch, and an updated dock. Take a peaceful stroll along the 60-foot walkway leading to a covered gazebo - the perfect spot for your morning coffee or evening sunset views. The community amenities include a lakefront pool and clubhouse, while the meticulously maintained grounds showcase lush Florida landscaping. Located just moments from Winter Park Village, you'll find fantastic shopping, dining, and entertainment options right around the corner. Experience the joy of maintenance-free living while being connected to nature and urban conveniences. This hidden gem won't last long!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,085
Status:
Active
MLS#:
S5140472
Type:
Condo
Subdivision:
Winter Park Woods Condo
Lot size:
0.07 Acres
Year built:
1974
A broker reciprocity listing Courtesy: LPT REALTY, LLC 877-366-2213
View additional info

ADDITIONAL INFORMATION

Excellent opportunity to own this second-floor, 2-bedroom, 1/1-bath condo in a Conveniently location close to healthy centers, excellent schools, restaurants and shopping with easy access to Costco, Walmart, and various dining options. Only 4 miles from Winter Park SunRail Train Station and 20 minutes from Orlando International Airport. This unit offers a cozy living/dining area with sliding doors leading to a private balcony that includes extra storage.

Open House:

Friday, 1/9 4:00-6:00PM

More Open House Info >

Beds:
2
Baths:
1.00
Sq.Ft.:
808
Status:
Active
MLS#:
O6368234
Type:
Condo
Subdivision:
Aragon Condo
Lot size:
0.13 Acres
Year built:
1984
A broker reciprocity listing Courtesy: LPT REALTY, LLC 877-366-2213
View additional info

ADDITIONAL INFORMATION

Welcome to 851 Miles Ave #13, a beautifully renovated 2-bedroom, 1-bathroom second-floor condo in the heart of charming Winter Park, FL 32789! Meticulously updated since 2023, this home blends modern luxury with effortless comfort and is truly move-in ready. As you step inside, you’ll be greeted by elegant porcelain tile flooring throughout—offering both durability and a look that’s easy to maintain. The heart of the home, the kitchen, has been completely reimagined with sleek granite countertops, fresh cabinetry, and contemporary finishes that make cooking and entertaining a joy. The bathroom has also received a full renovation, featuring granite countertops and updated fixtures that enhance both style and function. With thoughtful design at every turn, this condo feels fresh, bright, and uniquely yours. Situated on the second floor for added privacy and natural light, this unit provides a peaceful retreat while still being close to all that Winter Park has to offer. Enjoy being minutes from Park Avenue, with its array of boutique shopping, acclaimed restaurants, art galleries, and outdoor markets. Explore scenic parks, lakeside boat tours, cultural attractions, and community events that make Winter Park one of Central Florida’s most desirable places to live. Whether you’re searching for your next home or an exceptional investment opportunity, 851 Miles Ave #13 showcases stylish updates, quality finishes, and a location you’ll love. Don’t miss your chance — schedule a showing today!

Beds:
1
Baths:
1.00
Sq.Ft.:
673
Status:
Active
MLS#:
O6367841
Type:
Condo
Subdivision:
Park Aire Condo
Lot size:
0.56 Acres
Year built:
1956
A broker reciprocity listing Courtesy: PARK TOWN REAL ESTATE LLC 561-801-9199
View additional info

ADDITIONAL INFORMATION

Location, Location, Location! Charming first floor 1 bedroom, 1 bath condo ideally located on North Park Avenue in the retro-chic Park Aire complex. Beautifully overhauled in 2018 with quartz counters, new cabinetry, new appliances, custom mosaic kitchen detail, new flooring, new lighting, updated electrical, with picturesque views of the Winter Park Golf Course and Casa Feliz. Enjoy a large walk-in closet, one assigned carport space, and a private storage room. The community offers a sparkling saltwater pool, two third-floor outdoor patios, laundry facility, elevator, and a guest-quarters efficiency available to owners for a nominal fee. Just steps from Park Avenue shopping and dining, cafes, churches, Winter Park Golf Club, Rollins College and more. No pets.

Beds:
4
Baths:
4.00
Sq.Ft.:
2,916
Status:
Active
MLS#:
O6367773
Type:
Single Family
Subdivision:
Winter Park Village
Lot size:
0.18 Acres
A broker reciprocity listing Courtesy: ONE LUXURY INTERNATIONAL LLC 407-312-8003
View additional info

ADDITIONAL INFORMATION

Under Construction. An architectural statement in the heart of Winter Park, this remarkable residence designed by renowned architect Gary Hancock is a masterclass in craftsmanship, architecture, and timeless elegance. From the moment you arrive, the home commands attention with a breathtaking façade defined by graceful archways and refined architectural symmetry. Every exterior line and material selection has been intentionally chosen to create a presence that feels both bold and enduring, setting this residence apart as something truly exceptional. Inside, the home unfolds into a light-filled interior where design and livability coexist seamlessly. Ten-foot ceilings, level 5 drywall, and an abundance of expansive windows allow natural light to pour into every space, illuminating the impeccable finishes and creating an airy, sophisticated atmosphere throughout. Upgraded designer light fixtures add warmth and character, while the open-concept layout is anchored by a stunning living area centered around a refined fireplace, offering a natural gathering space that feels both intimate and grand. Flowing effortlessly from the living room, the dining area opens through elegant doors to the outdoor entertaining spaces, beautifully blending indoor and outdoor living. At the heart of the home, the chef’s kitchen is as visually striking as it is thoughtfully designed. Custom cabinetry with integrated LED under-lighting, sleek quartz countertops, a paneled refrigerator, and a premium induction range are complemented by a full suite of high-end stainless steel appliances, reflecting the builder’s uncompromising commitment to quality, performance, and clean modern design. The primary suite is a private retreat, highlighted by a spa-inspired bath with a freestanding soaking tub, an expansive walk-in shower, and a beautifully designed walk-in closet with direct access to the laundry room for effortless everyday living. Each secondary bedroom continues the theme of elevated design, offering generous proportions, abundant natural light, and elegantly appointed en-suite baths that ensure comfort and privacy for family and guests alike. Outdoors, the home reveals another level of thoughtful craftsmanship. A covered patio with a fully equipped summer kitchen overlooks a sparkling pool and expansive backyard, creating a setting equally suited for quiet evenings or lively gatherings. What truly defines this residence is the extraordinary level of craftsmanship throughout. No detail has been overlooked, no finish treated as an afterthought, and no design decision made without intention. This is a home that feels as impressive in its execution as it does in its presence.

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Andrea Conner, License #BK3437731, Xome Inc., License #1043756, [email protected], 844-400-9663, 750 State Hwy 121 Bypass, Suite 100, Lewisville, TX 75067


Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of {{last updated}}. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Copyright 2026, My Florida Regional MLS DBA Stellar MLS.

Andrea D. Conner, License # BK3437731, Xome Inc., License CQ1043756, [email protected], 844-400-XOME, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

All listings featuring the BMLS logo are provided by BeachesMLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed. Copyright © 2026 BeachesMLS, Inc.




Winter Park Real Estate

Winter Park is located in Florida. Winter Park, Florida has a population of 29,672. Winter Park is less family-centric than the surrounding county with 27.95% of the households containing married families with children. The county average for households married with children is 31.51%.

The median household income in Winter Park, Florida is $88,688. The median household income for the surrounding county is $65,784 compared to the national median of $69,021. The median age of people living in Winter Park is 45.3 years.

Winter Park Weather

The average high temperature in July is 92 degrees, with an average low temperature in January of 49.4 degrees. The average rainfall is approximately 51.9 inches per year, with 0 inches of snow per year.

Winter Park Map

Winter Park Real Estate Market Conditions

  • Median sales price

    $503,500
    25.3%
    change since last quarter
  • # Active listings

    279
    30-day change

Winter Park Schools and Demographics

Education near Winter Park, FL

City County
High School Graduates 96.78 89.47
College Degree - 2 year 9.01 11.45
College Degree - 4 year 62.48 35.7
Graduate Degree 17.77 9.12
Expenditures per Student 12,701 12,701
Students per Teacher 17.3 17.3

Elementary Schools near Winter Park, FL

Grades Students P/T Ratio ZIP
Aloma Elementary School PK - 05 528 15.5 32792
Aspire Academy Charter KG - 05 111 8.5 32804
Audubon Park Elementary School PK - 05 1,182 14.8 32814
Brookshire Elementary School PK - 05 632 12.9 32792
Dommerich Elementary School PK - 05 603 15.1 32751
Eastbrook Elementary School PK - 05 809 14.2 32792
Fern Creek Elementary School PK - 05 326 12.1 32803
Hillcrest Elementary School PK - 05 463 14.5 32803
Hungerford Elementary School PK - 05 283 13.5 32751
Killarney Elementary School KG - 05 444 14.8 32789
Lake Silver Elementary School PK - 05 688 12.3 32804
Lake Sybelia Elementary School PK - 05 600 13.3 32751
Lakemont Elementary School KG - 05 656 14.6 32792
Orlando Science Elementary Charter KG - 05 482 15.1 32804
Princeton Elementary School PK - 05 488 13.2 32804

Middle Schools near Winter Park, FL

Grades Students P/T Ratio ZIP
Glenridge Middle School 06 - 08 1,415 18.4 32814
Maitland Middle School 06 - 08 909 18.9 32751
Robert E Lee Middle 06 - 08 1,034 17.2 32804

High Schools near Winter Park, FL

Grades Students P/T Ratio ZIP
Edgewater High School 09 - 12 1,782 20 32804
Lake Howell High School 09 - 12 2,229 19.1 32792
Winter Park High School 09 - 12 3,069 18.7 32792
Workforce Advantage Academy Charter 09 - 12 238 47.6 32803

Ungraded Schools near Winter Park, FL

Grades Students P/T Ratio ZIP
* Aloma High Charter School 09 - 12 510 42.5 32792
* Winter Park Education Center 11 - 12 0 32789
Broward Science Charter School UG - UG 0 32804
Central Florida Leadership Academy Charter 06 - 12 189 15.8 32803
Gateway 06 - 12 63 3.7 32804
Hospital Homebound PK - 12 229 4 32804
La Amistad School KG - 12 48 9.6 32751
Orlando Science Middle High Charter School 06 - 12 555 15.4 32804
Pace Center for Girls 06 - 12 34 6.8 32803
Silver Star Center 06 - 12 25 2.5 32804
Winter Park Tech AE - AE 0 32789

Demographics near Winter Park, FL

City County
Neighborhood Type Suburban
Population 29,672 1,409,949
Population Density 3,393 1,562
Median Age 45.3 35.7
People per Household 2.3 2.9
Median Household Income 88,688 65,784
Average Income per Capita 67,032 33,498

Real estate near Winter Park