Winter Park Homes For Sale & Real Estate - 409 homes

Remarks: Great investment opportunity, tenant occupied/income producing Winter Park property in gated community.

Listing is courtesy of: LEGACY CORNERSTONE INC (407-674-5601)

Listing Agent: Kathi Thomas (407-674-5601)

Remarks: Welcome to 2052 Leanne Ct, a home that exudes warmth and elegance. The living room is graced with a cozy fireplace, perfect for those chilly evenings. The kitchen is a chef's dream, boasting all stainless steel appliances for a sleek, modern look. The primary bedroom is a haven of comfort with double closets for ample storage. The primary bathroom is a sanctuary with double sinks, providing ample space for your morning routine. The fenced-in backyard provides a private outdoor space for relaxation and entertainment. The home has been recently updated with fresh interior and exterior paint, giving it a clean, refreshed look. New flooring throughout the home adds a touch of sophistication and durability. The new appliances ensure efficiency and convenience. Included 100-Day Home Warranty with buyer activation

Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)

Listing Agent: Karen Albright (480-462-5392)

Remarks: Under contract-accepting backup offers. Back on the Market - Buyer Financing fell through. Turnkey and move-in ready! This beautifully updated 3-bedroom, 2-bath home offers modern finishes and an ideal floor plan in a fantastic location! Recent improvements include fresh interior and exterior paint, new flooring throughout, a fully renovated kitchen, and updated bathrooms. Roof (2022) Enjoy comfortable living with thoughtfully updated interiors and flexible living space. The spacious primary suite features an attached bonus room that is perfect for a home office, nursery, fitness space, or private retreat. The community amenities include a playground, tennis courts, and private lake access with a dock, providing plenty of opportunities for recreation and relaxation. Don’t miss this opportunity to own this beautifully updated home with outstanding community amenities and convenient access to everything the area has to offer!

Listing is courtesy of: RESULTS TEAM PROP & INVESTMENT (321-637-3737)

Listing Agent: Susan Heacock

Remarks: A PRIVATE RESORT-STYLE SANCTUARY IN THE HEART OF WINTER PARK 5 Bedrooms | 4 Bathrooms | 3,400+ SF|Saltwater Pool & Spa|Minutes to Park Avenue Welcome to a rare offering where luxury, tranquility, and architectural sophistication converge. Nestled in one of Winter Park's most desirable neighborhoods, just minutes from the boutiques, fine dining, and cultural attractions of Park Avenue, this custom Mid-Century Modern residence delivers an extraordinary lifestyle defined by elegance, wellness, and privacy. The home is within the acclaimed Winter Park school district, less than four miles from Trinity Preparatory School, and minutes from Rollins College and the University of Central Florida, placing premier educational opportunities nearby. Thoughtfully designed with a Zen-inspired aesthetic, the home blends clean architectural lines with warm natural elements to create a refined, restorative living experience. From the moment you arrive, a sense of calm surrounds you, offering a peaceful escape while remaining minutes from everything Winter Park offers. Inside, soaring 10-foot ceilings, expansive walls of glass, and wide-plank engineered hardwood flooring create bright, open living spaces filled with natural light. A semi-floating steel staircase with solid white oak treads serves as a dramatic focal point, while designer Restoration Hardware lighting adds warmth and sophistication throughout. The main living area was designed for entertaining. A Dimplex fireplace anchors the great room, complemented by a custom wine bar. At the heart of the home, the chef's kitchen showcases a waterfall island, premium quartz countertops, marble backsplash, double-stacked cabinetry, and a custom pantry. High-end Samsung smart appliances, including a Family Hub refrigerator, WiFi-enabled convection wall oven, Flex Duo cooking system, and 36-inch Bluetooth cooktop, complete this exceptional culinary space. A first-floor guest suite and full bath provide flexibility for visitors, a private executive office, fitness studio, or wellness retreat. The finished two-car garage features epoxy flooring and a modern glass garage door. Upstairs, the primary suite serves as a private sanctuary. The spa-inspired bath features a freestanding soaking tub, dual-entry marble shower with a semi-frameless glass enclosure, dual vanities, and a custom walk-in closet. Beyond the walls of the home lies your own private paradise. Professionally designed by Exotic Landscape Company, the resort-style outdoor living space evokes the serenity of a Balinese retreat. The newly constructed saltwater pool and spa showcase glass tile finishes, mini-pebble surfaces, travertine coping, LED lighting, therapy jets, a cascading waterfall, and smartphone-controlled OmniLogic automation. A custom outdoor stone shower, yoga platform, lush tropical landscaping, and curated hardscapes create an environment dedicated to relaxation and wellness. Additional features include Eufy smart lock technology, Arlo video doorbell, Google Nest thermostat, WiFi-enabled irrigation, smart garage controls, Quality Edge Vesta steel plank siding, and an expanded driveway. Less than ten minutes from Park Avenue, this exceptional residence offers a rare opportunity to own a home that feels more like a private luxury resort. More than a home, it is a sanctuary where timeless design, resort-inspired living, and one of Central Florida's finest educational settings create an unparalleled lifestyle.

Listing is courtesy of: SIMPLICITY: A RE BROKERAGE CO (407-920-6020)

Listing Agent: Robert Sassos (407-920-6020)

Remarks: Under contract-accepting backup offers. Positioned in one of Central Florida’s most iconic and sought-after locations, this rare opportunity at 1900 Winter Park Road in Winter Park invites you to create something truly exceptional. Set on a spacious homesite, this property offers the flexibility to renovate, expand, or build your custom dream home from the ground up. Whether you envision a modern architectural masterpiece or a timeless estate, this is your canvas to bring that vision to life. What makes this opportunity even more compelling is the location. Just minutes from the charm and sophistication of Park Avenue, you’ll find yourself surrounded by brick-lined streets, boutique shopping, fine dining, and vibrant cultural experiences. Spend your mornings enjoying coffee at local cafés, your afternoons exploring art galleries, and your evenings dining under the lights of one of Central Florida’s most beloved destinations. Living in Winter Park is more than owning a home—it’s embracing a lifestyle. From the scenic beauty of the Winter Park Chain of Lakes, to the historic elegance of Rollins College, this area blends natural beauty, culture, and community in a way few places can. Residents enjoy: Boat tours and waterfront living along the chain of lakes Weekly farmers markets and local events A thriving arts scene including museums, galleries, and theaters Top-rated dining and boutique retail experiences A true sense of community with timeless charm This is more than just land. This is where vision meets opportunity. This is where your next chapter begins. Build the life you’ve been dreaming of—in the heart of Winter Park

Listing is courtesy of: RE/MAX ASSURED (800-393-8600)

Listing Agent: William Grim, Iii (407-314-9784)

Remarks: Under contract-accepting backup offers. Completely reimagined in 2025, this stunning 2-bedroom, 2.5-bath townhome offers the perfect blend of modern luxury and an unbeatable Winter Park location. Just minutes from Rollins College, Park Avenue, boutique shopping, award-winning dining, and everything that makes Winter Park so desirable, this move-in-ready home has been thoughtfully renovated from top to bottom with timeless, designer-selected finishes. The heart of the home is the beautifully redesigned kitchen featuring Sarah Sherman Samuel cabinetry and hardware, gorgeous marble countertops, a custom marble ledge, and all-new appliances. Throughout the home, you'll find new flooring, smooth-finished walls, fresh interior paint, recessed lighting with dimmers, updated electrical, new interior doors and hardware, and new baseboards, creating a clean, sophisticated aesthetic. Upstairs, both spacious bedrooms feature beautifully updated en-suite bathrooms, while the primary suite includes a custom marble-top vanity and a thoughtfully designed built-in closet system. Every bathroom has been fully renovated with high-end finishes that elevate the home's overall design. Step outside to your own private outdoor retreat featuring a large covered patio with low-maintenance turf—perfect for entertaining, relaxing, or enjoying your morning coffee year-round. Major mechanical updates provide added peace of mind, including a 2023 air handler, 2024 water heater, all-new A/C ductwork, and added attic insulation for improved energy efficiency. With nearly every surface and major system thoughtfully updated, this exceptional Winter Park townhome offers luxurious, turnkey living in one of Central Florida's most sought-after neighborhoods.

Listing is courtesy of: ALL REAL ESTATE & INVESTMENTS (407-917-8206)

Listing Agent: Cara Edwards (407-616-3204)

Remarks: Under contract-accepting backup offers. Perfect Property for Builder or Investor Nestled in the sought-after Karolina on Killarney neighborhood, this classic 1935 bungalow offers timeless character and an exceptional opportunity to create your dream home in one of Central Florida's most desirable locations. Situated on a generous lot, this 2-bedroom, 1-bath residence features approximately 1,408 square feet of living space with a flexible floor plan ready for your personal vision. Original architectural details provide a warm foundation for renovation, restoration, or expansion, while the spacious backyard offers ample room for outdoor entertaining, gardening, or future additions. Whether you're a homeowner looking to customize a historic property or an investor seeking your next project, this home presents outstanding value in a neighborhood surrounded by beautifully updated residences. Ideally located just minutes from Park Avenue's renowned dining, boutique shopping, museums, and year-round events, you'll also enjoy convenient access to Downtown Orlando, College Park, Winter Park Village, major hospitals, and top commuter routes. With no HOA and a prime location in the heart of Winter Park, opportunities like this are increasingly rare. Bring your imagination and unlock the incredible potential this charming property has to offer!

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)

Listing Agent: Elly Kennedy (407-376-8308)

Remarks: Under contract-accepting backup offers. Welcome to the heart of Winter Park. This beautifully maintained 4-bedroom, 2.5-bath pool home offers the perfect blend of warmth, functionality, and charm. From the moment you arrive, the curb appeal is unforgettable. Lush landscaping, mature greenery, and peaceful natural surroundings create a private and inviting setting that immediately feels like home. Inside you'll find an open and welcoming floor plan designed with both everyday living and entertaining in mind. The updated kitchen features stainless steel appliances, a spacious island, abundant cabinet storage, and seamless flow into the main living areas. A formal living area adds flexibility, offering the perfect space for a cozy sitting room, playroom, home office, or additional entertaining area. Natural light throughout the home creates a bright and airy atmosphere. Upstairs, you’ll find all four bedrooms and two full bathrooms, providing privacy and functionality for growing families. The screened-in porch overlooks a stunning backyard retreat complete with a sparkling pool, beautiful landscaping, and no rear neighbors for added privacy. Peaceful, quiet, and surrounded by nature and wildlife, this outdoor space makes it perfect for summer pool days, evening dinners outside, and making lifelong memories.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Brianna Lalumiere (727-641-3957)

Remarks: Lakefront Community! Enjoy Glorious Sunsets, Cocktails on the Deck and the Peace of Water and the Amazing Joy of Nature! All this near the heart of Winter Park and walking distance to all kinds of Shopping! One of few 1 Bedrooms and an Upstairs End Unit! Enjoy Spacious Room Sizes for easy Furniture Placement, Compact Kitchen, Bright Master Bedroom with additional Built-in Closets, Vanity and Mirrored Closets and updated Bath, accessible for Guests and close to Master! Updated Windows! Private Balcony! Owner is providing a One-Year Home Warranty and a $3,000 Flooring Credit. Make this affordable Unit your own!

Listing is courtesy of: REALCOM REAL ESTATE SERVICES INC (407-621-6856)

Listing Agent: Janice Erickson (407-621-6856)

Remarks: Exceptional opportunity to build new or renovate and expand on this desirable lot in Winter Park. Situated on a charming tree lined street and in a neighborhood that is experiencing a great deal of new development. The existing 1950s residence features parquet wood flooring and open living and dining spaces, which overlooks the backyard and open wooden deck. With generous space to work with, there are great possibilities to create your own custom residence. The property is zoned for long-established schools - Lakemont Elementary, which is just down the street from the property, as well as Maitland Middle and Winter Park High. Plus, ideally located within a short stroll to the Winter Park Y, Phelps Park, and minutes to downtown Park Ave's shopping and dining! Property is being sold AS IS.

Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)

Listing Agent: Dawn Romance (407-929-2826)

Remarks: Move-in-ready Winter Park gem in top-rated Seminole County schools! This 3BR/2BA home features a private split-bedroom layout. The home features laminated wood flooring in all the bedrooms and beutiful tile in the kitchen and bathrooms. Both bathrooms feature newly updated toilets. The expansive eat-in kitchen is a chef's delight, boasting premium granite countertops, solid light maple cabinets with elegant glass upper doors, and a breakfast bar opening to the large family room. Enjoy total peace of mind with extensive 2023 upgrades, including a BRAND NEW ROOF, new electrical panel, new energy-efficient windows, new French doors, and a new garage door for the 2-car garage.The HVAC system was manufactured in 2019 and installed in 2020 Step outside to a massive, fully fenced backyard featuring a large covered lanai with a brand-new aluminum frame and fresh screens—perfect for outdoor entertaining. Truly a turnkey property optimized for insurance savings and modern comfort. Schedule your tour today!

Listing is courtesy of: PREMIUM PROPERTIES R.E SERVICE (407-380-2800)

Listing Agent: Celimar Sierra, Llc (407-731-2678)

Remarks: NEW PRICE OFFERING IN EASTBROOK! Significant $15,000 price drop, placing it well below recent neighborhood comparables. Welcome to Winter Park's best-keep secret. Quiet, safe, family-oriented, with almost zero traffic and zero HOA restrictions and fees – Eastbrook is 32792’s hidden gem. This 3-bedroom, 2-bath home provides unmatched market value and instant equity, pairing mid-century charm with a long list of mechanical updates. Aside from the 7-year windows and electrical panels, and an 8-year, thoroughly-serviced and well-maintained AC unit inside and out, the water heater, exterior paint and window blinds are under a year old. PLUS the brand-new ceiling fans, light fixtures, gutter screens, smoke detectors, interior paint - and all conveying appliances in perfect working order - give you a worry-free, move-in-ready home. Now, let’s talk about that massive backyard oasis! Lush mature trees, a “grass-covered” patio, and a large concrete firepit all conspire to provide a perfect spot for entertaining and room for kids and pets to romp. The house's bonus features include a covered carport, huge separate, air-conditioned laundry room, tons of storage space inside and out, and a separate cross-fenced side yard for vehicles and other large items. To round out these stellar amenities, potential buyers will have peace of mind knowing the roof, electrical, and plumbing systems have all been recently inspected and found in tip-top shape! What’s not to love about this adorable, cozy house?

Listing is courtesy of: SAVVY AVENUE, LLC (888-490-1268)

Listing Agent: Moe Mossa (888-490-1268)

Remarks: Welcome to this beautifully updated condo, ideally nestled between Winter Park and Maitland. This inviting home features a versatile upstairs loft overlooking the living and dining areas—perfect for a home office, fitness space, craft room, or additional guest accommodations. The bright, cheerful eat-in kitchen is both stylish and functional, showcasing quartz countertops, a glass tile backsplash, abundant cabinetry, a pull-out spice rack, trash/recycling cabinet, and a built-in storage unit. Sliding glass doors open to the private front courtyard, filling the space with natural light. Conveniently located laundry area, complete with washer and dryer, is tucked within the kitchen. The spacious living room features a cozy wood-burning fireplace and flows seamlessly into the dining area beneath soaring vaulted ceilings accented by skylights. Sliding glass doors lead to a screened lanai with a slate tile floor and a storage closet—an ideal spot to relax and enjoy Florida living. The primary suite also opens directly to the lanai and offers a beautifully renovated en-suite bath with a luxurious walk-in shower, updated vanity, linen cabinet, and a custom walk-in closet with built-in organizers. The front bedroom also includes a generous walk-in closet. Enjoy added privacy with a picturesque, tree-lined green space across the street rather than neighboring condos directly in front. Two dedicated parking spaces are conveniently located just outside your door. Cedarwood Village offers an exceptional location directly across from Casselberry Commons Shopping Plaza and is just minutes from Full Sail University, UCF, and Rollins College. Residents enjoy a community swimming pool, tennis courts with pickleball lines, and designated dog-walking areas. Additional highlights include a new roof and skylights installed in 2020. Monthly HOA fees cover exterior maintenance, lawn care, and community amenities, making this the perfect opportunity to enjoy carefree living in one of the area's most desirable communities.

Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)

Listing Agent: Sheila Mathews (407-701-5656)

Remarks: ***FULLY REMODELED WINTER PARK POOL HOME NEAR BALDWIN PARK! *** 1 YR HOME WARRANTY INCLUDED — a beautifully updated 4-bedroom, 3-bath home with a dedicated office, ideally located near both Winter Park and the highly sought-after Baldwin Park community, known for its lakeside dining, walkability, parks, boutiques, and vibrant neighborhood atmosphere. This move-in ready home features an open and light-filled layout with designer finishes throughout, including updated flooring, custom cabinetry, modern lighting, and beautifully remodeled bathrooms and kitchen with premium appliances and upscale countertops. Major upgrades include a NEW roof (2023), windows (2023), water heater (2023), electrical panel (2023), plus updated plumbing and electrical throughout for true peace of mind. Enjoy spacious living areas, a luxurious primary suite, and a private backyard perfect for relaxing or entertaining. Conveniently located near top-rated schools, parks, shopping, dining, Park Avenue, and everything Winter Park living brings, this home combines modern updates with an unbeatable Central Florida location.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Youbel Montesino (954-608-4838)

Remarks: Oversized corner lot in quiet neighborhood with highly desired Seminole County schools. Well-built block on slab four bedroom home with split floor plan. Enclosed large Florida room. Shed. Existing irrigation well (but pump not working--no warranty on well). Double gate to back yard for parking RV/toys (back left). Roof 2018; water heater 2018; HVAC 2017; CPVC plumbing.

Listing is courtesy of: SPARROW REALTY & RENTALS (407-963-8326)

Listing Agent: Brian Dodd (407-963-8326)

Remarks: Welcome home to this stunningly renovated 4-bedroom, 2.5-bath with TWO additional rooms that can be used as an office space, playroom etc single-family residence located in the heart of Winter Park! This home offers an abundance of space, comfort, and modern convenience in one of Central Florida’s most desirable areas. Step inside to find a bright and open kitchen overlooking a spacious living area—perfect for entertaining family and friends. The additional office space provides a quiet spot for work or study, while the split floor plan ensures privacy and comfort for everyone. Each bedroom features ample closet space, and the home’s thoughtful layout makes daily living a breeze. Enjoy outdoor relaxation on the large backyard and covered porch, ideal for gatherings or peaceful evenings at home. The property also includes an exterior laundry room with washer and dryer for added convenience.

Listing is courtesy of: FLORIDA PROPERTY SPECIALIST (407-523-2323)

Listing Agent: Nancy Rossman (407-230-2536)

Remarks: This home is an adorable 4 Bed 3.5 Bath Home in the heart of Winter Park. You will feel right at home the moment you step in. lovely kitchen showcases gorgeous cabinets, stainless steel appliances, ample amount of cabinetry and counter space, and a breakfast bar, great for entertaining family and friends. Open floor plan. Home features a separate dining area off the kitchen. Spacious living space and bedrooms. Spend your evenings and weekends relaxing on the beautiful lakefront of Lake Killarney, enjoying the incredible sunsets under the shade of huge cypress trees OR poolside in the private fenced in backyard.

Listing is courtesy of: FLORIDA PROPERTY SPECIALIST (407-523-2323)

Listing Agent: Nancy Rossman (407-230-2536)

Remarks: Discover the potential of this spacious 4-bedroom, 2.5-bath home located at 1564 Lawndale Cir in desirable Winter Park. Featuring a comfortable floor plan with generous living space, this home offers flexibility for everyday living, entertaining, working from home, or hosting guests. The bedroom layout provides privacy and functionality, while the location offers convenient access to shopping, dining, parks, schools, major roadways, and nearby Orlando destinations. With its size, layout, and prime Winter Park location, this property is a great opportunity for buyers looking to personalize a home and create lasting value. Don’t miss your chance to schedule a private showing.

Listing is courtesy of: SET HOMES REALTY LLC (407-690-3314)

Listing Agent: Yahya Chhotani Llc (732-955-1302)

Remarks: In the heart of Winter Park's vibrant Hannibal Square, this exceptional one-story residence, completed in 2022, offers the ideal blend of contemporary design, refined finishes and an unbeatable accessible lifestyle. Thoughtfully designed with three bedrooms, two and one-half baths, and an open-concept floor plan, the home showcases clean architectural lines, soaring ceilings and walls of glass that fill the interior with natural light while framing views of the beautifully landscaped grounds. The chef's kitchen serves as the centerpiece of the home, featuring premium Wolf and Sub-Zero appliances, custom cabinetry, a center island with seating, and workspace for everyday living and entertaining. The adjoining dining area flows seamlessly into the spacious great room, where custom-built library shelving creates a striking focal point and adds warmth and character to the modern design. Beautiful polished concrete floors extend throughout the residence, providing a cohesive and sophisticated aesthetic. Designed with privacy in mind, the split-bedroom floor plan places the primary suite in its own secluded wing. This spacious retreat offers direct access to the covered rear patio and features a beautiful bath with dual vanities, an oversized walk-in shower, private water closet, and an impressive custom walk-in closet measuring approximately 11 by 9 feet. Conveniently accessible from the primary bath and laundry room, the thoughtfully designed closet enhances everyday functionality. On opposite side of the home, two additional guest bedrooms are connected by a well-appointed Jack-and-Jill bath, while a stylish powder bath is ideally located for visitors. Outdoor living is equally inviting with a covered patio with a privacy bamboo hedge that creates a peaceful backdrop for relaxing or entertaining. An attached two-car garage completes this beautifully appointed residence. Ideally near the acclaimed restaurants, wine bars, coffee shops, and boutiques of Hannibal Square, this home offers one of Winter Park's desirable lifestyles. Visit the renowned shopping, dining, galleries and sidewalk cafés of Park Avenue, enjoy nearby Central Park and community events, or take advantage of the proximity to Rollins College, the Winter Park Farmers' Market and major roadways providing convenient access throughout Central Florida. This is a rare opportunity to enjoy nearly new construction in one of Winter Park's sought-after neighborhoods, where modern luxury and exceptional accessibility come together.

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Mick Night (407-629-4446)

Remarks: Under contract-accepting backup offers. Cute as a button and move-in ready! This charming top floor 1-bedroom, 1-bath condo offers a bright, airy feel with an open-concept layout designed for comfortable living. Literally just steps away, you will enjoy peaceful views overlooking the hot tub and community pool from your private retreat above it all! The updated kitchen features beautiful white cabinetry with SOFT-CLOSE DRAWERS, providing both style and functionality. The spacious living area is enhanced by a vaulted ceiling that creates an expansive feel and allows natural light to pour in throughout the day. The primary bedroom continues the open, inviting atmosphere with vaulted ceilings and a generous walk-in closet. The bathroom offers a raised-height vanity with ample countertop space, making your daily routine both convenient and comfortable. This unit also comes with an INTERIOR LAUNDRY so you don’t have to worry about going off-site! Whether you’re relaxing at home on your SCREENED PATIO, enjoying the pool or hot tub, or taking in the view from your top floor location, this condo is the perfect blend of charm, comfort, and convenience. Come see it today!

Listing is courtesy of: VALENCE REALTY GROUP (407-797-5034)

Listing Agent: Chuck Valence (407-797-5034)