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$800,000
3 Beds ⋅ 2 Baths ⋅ Golfview Heights SubDv. ⋅ 32789 Zip Code
Rare opportunity in the heart of Winter Park! This property sits on a double lot (0.29 acres) — a true rarity in this highly desirable location. The existing 1953 concrete-block home (3 bed / 2 bath) with an attached garage apartment (studio + bath) and shared 2-car carport offers little to no current value and would require a complete renovation. Property will be sold as-is with no repairs. Furniture removal prior to closing is negotiable. The real value is in the land. With privacy at the end of a quiet street, and a doctor’s office next door, the property is ideally located steps from AdventHealth Winter Park Hospital, Lakemont Center, and just 5 minutes from Rollins College and Park Avenue’s shopping and dining. The property features a large tree-lined backyard, city water and sewer, cable, and electricity already available. Whether you choose to restore a solid 1950s block home or tear down and build your dream estate while saving on impact fees, this is a prime investment opportunity in one of Central Florida’s most sought-after areas.

1822 Greenwich Avenue, Winter Park
$162,000
1 Beds ⋅ 1 Baths ⋅ Mead Garden SubDv. ⋅ 32789 Zip Code
One or more photo(s) has been virtually staged. Come take a lovely stroll to Mead Gardens(47 acres), located just around the corner from this adorable condo in one of Winter Park’s most popular communities! The pool is located directly behind this condo! This cozy first-floor unit features brand-new luxury vinyl flooring that gives it a fresh, welcoming feel. The spacious living room has sliders that open up to a nice-sized screened-in Florida room—perfect for sipping your morning coffee or relaxing at the end of the day and the best part the pool is located directly behind your Florida room! With the large Florida palm tree as a reference point you can see how close to the pool this condo is! After you enjoy taking a hike around Mead Gardens- then come home to a nice swim in the pool! And here’s some exciting news: the seller is offering seller financing! That means the deed will be in your name, and with just 20% down and flexible terms, it’s an incredible chance for first-time buyers, or to add to your rental portfolio, or anyone looking for a sweet second home. If you've been dreaming of having a Winter Park address, this is your moment! You’ll absolutely love the fantastic location of this condo, and let’s not forget this condo is located less than 2 miles to Advent Health hospital, the Orlando Science center, shopping, restaurants and all that Winter Park has to offer! Don’t miss out on this wonderful investment opportunity. Show and Sell!!

1250 S Denning #122 Street Unit 00122, Winter Park
$1,500,000
4 Beds ⋅ 5 Baths ⋅ Tangerine Court SubDv. ⋅ 32789 Zip Code
Just Reduced $100,000 below appraised value!!!!! Experience refined living in this completely remodeled single story residence located in the heart of Winter Park. Enjoy luxury living in this impeccably maintained home. This beauty offers three spacious bedrooms and three beautifully appointed baths in the main house and a 1bed/1bth studio apt above the garage. Enter the spacious floorplan featuring open living and dining areas separated by a gorgeous double sided fireplace. The kitchen is a chef's dream with updated appliances and stunning marble countertops complete with lots of storage and work space. The living room features a panel of french doors overlooking the professionally landscaped and pavered back yard complete with a large resort style pool and soothing heated spa. Enjoy your morning coffee and your favorite afternoon beverage on the pavered lanai featuring remote control exterior shades. A half pool bath is part of this amazing landscape. The 2+car detached garage features an upstairs studio apartment perfect for guests, a home office or rental income. It is complete with a kitchenette, large bathroom and washer/dryer. The large master bedroom boasts two walk in closets, open step in shower, a double vanitiy and water closet . Lots of natural light, too!! Enjoy the guest room complete with an en-suite bath and, of course, the 3rd bedroom is perfect for family. Your paradise is only 2 miles from Park Avenue known and loved by so many for it's art galleries, restaurants, upscale shopping and parks. Top rated medical facilities within a short distance. This is lifestyle living at it's finest !

132 Burks Circle, Winter Park
$505,000
3 Beds ⋅ 2 Baths ⋅ Villa View Park SubDv. ⋅ 32789 Zip Code
Winter Park home for sale

1651 N Park Avenue, Winter Park
$555,000
3 Beds ⋅ 3 Baths ⋅ Park Shore SubDv. ⋅ 32789 Zip Code
One or more photo(s) has been virtually staged. Modern Comfort in the Heart of Winter Park! Built in 2019, this 3-bedroom, 2-bath, 1,798sf townhome offers the perfect blend of convenience and contemporary style in a private 12-unit community. Light and bright with high ceilings and tile floors, the open-concept living area features a quartz island kitchen with Samsung appliances, solid wood cabinetry, and a retractable sliding door that opens to a walled courtyard—ideal for dining and entertaining. Upstairs, you’ll find the spacious primary suite, two additional bedrooms, a secondary bath, and a laundry room. Additional features include a downstairs custom closet, upgraded sound system with subwoofer and speakers throughout the main living areas and patio, central vacuum, security system, and an attached two-car garage. Enjoy low-maintenance living close to I-4, College Park, Park Avenue, shopping, and dining.

1267 Michigan Avenue, Winter Park
$6,495,000
5 Beds ⋅ 7 Baths ⋅ Osceola Place SubDv. ⋅ 32789 Zip Code
Exquisite new construction with 5 Bedrooms 6.5 Baths and a 3 car garage, in the Heart of Winter Park perfectly positioned on an oversized lot just steps from Park Avenue’s renowned shops, fine dining, and the iconic Winter Park 9-hole golf course, this extraordinary custom residence is a showcase of timeless design and modern luxury. Conceived by acclaimed architect Dan Delong of Origins Residential Design and brought to life by Sean Wulff of Native Homes, every detail has been thoughtfully curated to impress even the most discerning buyer. The expansive floor plan encompasses 5 bedrooms, 6 full baths, and 1 half bath, blending sophistication and comfort across multiple living spaces. Highlights include a dramatic great room, inviting family room, private study, downstairs guest suite, a full bar featuring a 56-bottle wine refrigerator, and an upstairs game room ideal for both everyday living and elegant entertaining. A grand entry reveals the great room with soaring floor-to-ceiling windows and elegant Italian porcelain tile, all overlooking the serene pool and patio. The chef’s kitchen seamlessly connects to the family room and features Canadian-crafted European-style cabinetry, Wolf, Sub-Zero & Fisher & Paykel appliances (dual ovens, dual dishwashers, built-in coffee maker, wine cooler, and beverage center), quartzite countertops, a large island with bar seating, hidden walk-in pantry, plus whole house water softener and filtration systems for premium convenience. The first-floor primary suite is a true retreat with spa-inspired amenities and a custom-built walk-in closet complete with cabinetry and a spacious island. Also on the main level: a private guest suite and dedicated home office/study. Upstairs, a generous game room and three additional en suite bedrooms provide comfort and privacy for family and guests alike. Designed for seamless indoor-outdoor living, the residence boasts two covered lanais finished in Turkish Marble, disappearing screens, a summer kitchen with Urban Bonfire Cabinetry, refrigerator, and ice maker, along with a freestanding fire pit and lush tropical landscaping. The saltwater pool with sun shelf and heated gas spa ensures year-round enjoyment. Built to the highest standards, the home features R-14 block walls with core 500 insulation, open cell foam insulation in attic, Andersen windows, a flat concrete tile roof, and tongue-and-groove ceilings on all lanais. Additional luxuries include: Select European white oak wood floors and Italian porcelain flooring throughout 12’ ceilings on the main level, 10’ ceilings upstairs Cutting-edge construction for efficiency and durability

550 Palmer Avenue, Winter Park
$720,000
4 Beds ⋅ 3 Baths ⋅ Howell Forest SubDv. ⋅ 32789 Zip Code
Discover The Hills of Winter Park, a quiet, tree-lined community just minutes from Park Avenue. This beautifully updated single-family home offers 3,902 square feet of living space on a 0.20-acre lot. It features two spacious primary suites—one located upstairs with a vaulted shiplap ceiling, three walk-in closets, and a private balcony overlooking the pool and spa. The remodeled kitchen includes a 5’x10’ stone island, stainless steel appliances, a 42” Kenmore range, and opens to generous living and dining areas with a wood-burning fireplace. Additional highlights include a large recreation room with French doors leading to a screened lanai and private fenced backyard oasis, perfect for entertaining. Enjoy plenty of driveway and street parking, plus a dedicated area on the lot ideal for recreational storage—perfect for boats, trailers, or extra gear. While there is no garage, the home offers ample storage space throughout, including multiple walk-in closets and flexible indoor utility areas. Recent upgrades include a 2023 roof, indoor laundry room, and an American Home Shield warranty. A rare opportunity to live, work, and relax in the heart of Winter Park.

2955 Lolissa Lane, Winter Park
$359,900
3 Beds ⋅ 2 Baths ⋅ Dubsdread Heights SubDv. ⋅ 32789 Zip Code
One or more photo(s) has been virtually staged. Fantastic Opportunity / Dubsdread Heights in Winter Park! Do not miss out on this great opportunity to own a home in the desirable College Park area located in Dubsdread Heights. This charming 3-bedroom, 2-bath residence sits on an oversized 50 x 140 lot and offers 1,283 sq. ft. of air-conditioned living space. Featuring a split-bedroom floor plan, the home includes hardwood floors in several rooms, a spacious kitchen with tile flooring and wood cabinetry, and a dining room enhanced by a beautiful tongue-and-groove wood ceiling.The primary bedroom boasts wood floors, a tongue-and-groove wood ceiling, a wall closet, and an en-suite bath with dual sinks, a shower, and a laundry closet with a washer and dryer. The two additional bedrooms share a bright hall bath with a tub/shower combo. Just off the kitchen, a 12 x 16 enclosed porch overlooks the expansive backyard, which includes an adjacent patio and two storage sheds that convey with the property. Updates Include New Roof (August 2017), New Electrical Panel (August 2023), Septic System Fully Cleaned and Serviced (Early 2025) & HVAC System (2018) Located just one block from the Dubsdread Golf Course, this home is ideally situated minutes from I-4, Downtown Winter Park, Park Avenue, College Park, AdventHealth Hospital, and Downtown Orlando. Perfect as a primary residence or an excellent investment opportunity in a prime location.

780 Baffie Avenue, Winter Park
$1,389,500
4 Beds ⋅ 5 Baths ⋅ Lake Killarney Shores SubDv. ⋅ 32789 Zip Code
GORGEOUS NEW CONSTRUCTION IN WINTER PARK! Discover sophisticated modern living at 607 Ellen Drive — a brand-new construction masterpiece by the acclaimed Lazarus Homes, perfectly positioned in the heart of Winter Park. At this new price, it's simply unmatched value for new construction in this location. This impeccably designed 2,812-square-foot residence showcases striking contemporary architecture with clean lines, soaring ceilings, and natural light pouring in from every angle. The open floor plan flows effortlessly from space to space, creating the ultimate backdrop for everyday living and unforgettable entertaining. The chef's kitchen is nothing short of a showstopper — outfitted with top-of-the-line Monogram appliances, a sleek Ruvati sink, built-in oven and microwave, and a professional gas range. Show-stopping Taj Mahal Quartzite countertops bring both drama and durability, and you'll have the flexibility to add a full-height wine refrigerator or extra cabinetry to make the space truly your own. The living room delivers modern warmth with an electric fireplace and walls of glass sliders that open wide to a covered lanai and your own private pool — Florida indoor-outdoor living at its absolute best. Love to entertain? The home comes pre-stubbed for an optional outdoor kitchen, ready when you are. Retreat to the luxurious first-floor primary suite, a true private sanctuary with a spa-inspired en suite bath — double sink vanity, walk-in shower, soaking tub, and an oversized walk-in closet with custom built-ins and washer/dryer hookups. Upstairs, the impressive layout continues with a spacious bonus room, a striking loft framed in glass walls, three more bedrooms, two full baths, and a second laundry area for effortless convenience. A dedicated pool bath rounds things out for easy poolside enjoyment. Tucked into the sought-after Lake Killarney Shores community, this home is the ultimate blend of peaceful retreat and unbeatable location. Enjoy a low HOA, private boat launch access to Lake Killarney, and a walkable stroll to Winter Park's best restaurants, boutiques, and cultural hotspots. New construction, lake access, unbeatable location, and a brand-new price — this move-in-ready modern luxury home won't last long!

607 Ellen Drive, Winter Park
$645,000
2 Beds ⋅ 2 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code
Discover the timeless allure of this enchanting 2 bedroom, 1.5 bath home, built in 1936 and nestled in the heart of historic Winter Park steps from Lake Mizell. Located on one of the area's iconic brick-paved streets and surrounded by majestic oak trees, this Winter Park bungalow is a rare find. The home's classic design features original hard wood floors, original glass windows, a cozy wood-burning fireplace, and an abundance of natural light blending vintage charm with practical functionality. With its warm character and unbeatable location, this delightful property captures the essence of Winter Park living at its finest.

224 Overlook Road, Winter Park
$479,000
2 Beds ⋅ 1 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code
Beautiful piece of property on Clay St. in Winter Park. Fantastic location. Nearly a third of an acre. Minutes to downtown Winter Park , Advent Health medical center on Rollins St. and Dubsdread golf course. *Double gate fence for boat or RV. *Newer A/C in 2017. *Newer roof in 2017. *Garage *Huge fenced-in backyard. *Wood floors. Enjoy this home or build new on this great piece of property. Come and imagine the possibilities. What's your offer?

1386 Clay Street, Winter Park
$1,700,000
Kenilworth Shores Sec 06 SubDv. ⋅ 32789 Zip Code
An exceptional opportunity to design and build your dream lakefront home in Winter Park. Positioned on the shores of Lake Berry, one of the area's private and pristine ski lakes with no public ramp, this property offers a rare combination of privacy, location and potential. Set on over a half-acre of lakefront land, the property features a four-bedroom, two-and-one-half bath, single-story residence with a covered boat dock, ideal for enjoying lake life immediately or while planning a future custom build. The northeast-facing front provides the ideal orientation to capture breathtaking sunsets across the water each evening. Whether you choose to renovate the existing home or build a new architectural masterpiece, this offering presents the ultimate canvas for creating a generational lakefront retreat. Within minutes of downtown Winter Park, Park Avenue and A-rated public schools, this property combines the best of convenience, serenity and luxury lakefront living. A special opportunity to bring your vision to life on one of Winter Park's desired private lakes.

633 Balmoral Road, Winter Park
$375,000
3 Beds ⋅ 2 Baths ⋅ Albert Lee Ridge Add 02 SubDv. ⋅ 32789 Zip Code
Welcome to your next chapter at 1007 Early Ave in Winter Park, a charming 3-bedroom, 2-bathroom home. Thoughtfully maintained, this home combines character with modern comfort. Step inside to find inviting living spaces and enjoy peace of mind with a roof replaced in 2019. The spacious backyard is perfect for entertaining, gardening, or simply relaxing under the Florida sun. With plenty of room to play, it’s a rare find in Winter Park and offers potential for future outdoor upgrades or expansion. Located just minutes from downtown Winter Park, you’ll have easy access to top-rated dining, boutique shopping, and cultural attractions. Whether you’re a first-time homebuyer, a growing family, or looking for a smart investment in Central Florida’s thriving market, this home checks all the boxes! Schedule your showing today!

1007 Early Avenue, Winter Park
$414,000
3 Beds ⋅ 2 Baths ⋅ Dubsdread Heights SubDv. ⋅ 32789 Zip Code
Welcome to this fully remodeled, move in ready home perfectly situated on a spacious corner lot in Winter Park, just blocks from the Dubsdread Golf Course and close to the shops, restaurants, and charm of College Park and downtown Winter Park. Every inch of this 3 bedroom, 2 bath home has been thoughtfully updated to blend modern comfort with timeless style. Step inside to find a bright, open layout with beautiful tile flooring throughout for a clean, cohesive look. The spacious living and dining areas flow seamlessly together, creating an inviting space that’s ideal for entertaining or relaxing at home. The updated kitchen is a showstopper, featuring shaker cabinets, quartz countertops, a farmhouse sink, stainless steel appliances, and elegant finishes that make it both stylish and highly functional. Whether cooking a weekday dinner or hosting friends, this kitchen will quickly become the heart of the home. The primary suite includes a modern barn door entry to the walk in closet and a renovated bathroom with fresh, contemporary finishes. Two additional bedrooms and another updated full bathroom complete the interior, providing comfortable accommodations for family, guests, or a home office. Step outside and enjoy your private backyard retreat, fully enclosed with Vinyl Fencing for privacy. Entertain under the gazebo or relax on the paver patio. Take advantage of the 10x15 shed with power, perfect for a workshop, studio, or extra storage. Major system updates ensure peace of mind for years to come including double pane windows throughout, a 2020 AC unit and a 2016 roof. With its prime location, modern upgrades, and turnkey condition, this home is priced to sell and ready for its next owner. Schedule your private showing today!

740 Baffie Avenue, Winter Park
$4,720,000
5 Beds ⋅ 6 Baths ⋅ Camwood Sub SubDv. ⋅ 32789 Zip Code
*Under Contract - Accepting Backup Offers* An expression of modern luxury by SMRS Design and Cole Homes, The Maybourne masterfully blends Neoclassical elegance with Art Deco sophistication—all just steps from Winter Park’s iconic Park Avenue. A curved, manicured driveway leads to a grand entrance featuring bespoke double doors with electromagnetic privacy glass, setting the tone for the artistry within. Inside, a European hotel–inspired foyer greets guests with precast stone-clad walls, inlaid marble flooring, and a Murano-style polyhedral chandelier. Two first-floor guest suites, each with its own bath, are adorned with rift-cut white oak millwork, curved ceilings, and crystal chandeliers. At the heart of the home lies the main salon, where oak detailing and a deco-style stone fireplace with a holographic insert create an atmosphere of understated grandeur. The two-tone oak kitchen, wrapped in natural quartzite and anchored by a curved island and custom hood, features a curated suite of professional-grade appliances: • ILVE range • Miele refrigerator, freezer, and dishwasher • Sub-Zero wine and beverage preservation systems Adjacent, a dining area glows under a custom chandelier, while the powder bath impresses with wood and marble accents, an integrated stone sink, and a Saint Louis crystal faucet by Kallista. A scullery expands the culinary capability with a chef’s sink, Samsung Bespoke laundry and refrigeration, Wolf microwave drawer, and additional Miele dishwasher—ideal for both entertaining and daily ease. The first floor primary suite, discreetly hidden behind millwork, offers a serene retreat with an opulent closet system and a marble mosaic-clad bathing suite featuring Kohler digital shower technology and MTI tub. Upstairs, two additional ensuite bedrooms, a bonus room with walk-in closet, and a secondary laundry continue the home’s standard of refined luxury. Outdoors, the residence embraces resort-style living with a natural gas summer kitchen, infinity-edge pool, and 360-degree raised glass-tile spa. A two-car garage and porte cochere, both EV-ready, provide elegant utility. Modern conveniences include Lutron HomeWorks lighting and shade prewire, built-in SONOS audio zones, pre-installed speakers, and a commercial-grade Ubiquiti WiFi network ensuring flawless connectivity throughout. A feast for the senses, The Maybourne is more than a home—it’s a statement of artistry and craftsmanship, conceived for the most discerning Winter Park resident.

1302 Raintree Place, Winter Park
$586,000
2 Beds ⋅ 2 Baths ⋅ Village Winterset Inc SubDv. ⋅ 32789 Zip Code
RARE CORNER TOP-FLOOR CONDO WITH AMAZING VIEWS – FULLY FURNISHED AND IN THE HEART OF WINTER PARK! Discover the perfect blend of comfort, style, and unbeatable location! This beautifully maintained 2-bedroom, 2-bath corner unit sits on the top floor of the desirable Villages of Winterset, offering expansive views and abundant natural light throughout. Enjoy the convenience of two elevators, a private storage unit on the same floor, and on-site laundry just steps from your door. Your assigned covered parking keeps your car cool and protected, and the secured mid-rise building features key access, a call box for guests, and a welcoming lobby lounge. Step outside and you’re just a short walk to everything that makes Winter Park special — Park Avenue’s boutique shops and restaurants, Rollins College, the Morse Museum, Winter Park Golf Course, and the SunRail station. Central Park is right there for art festivals, concerts, and weekend strolls! Relax at home by the sparkling community pool, enjoy the sun deck or BBQ area, and soak in the charm of one of Winter Park’s most beloved communities. Winterset is owner-occupied only, where rentals and pets are not permitted ensuring peace, privacy, and pride of ownership all around. Come see why homes at Winterset rarely hit the market — and fall in love with your new Winter Park lifestyle!

265 E Canton Avenue Unit GE, Winter Park
$105,000
2 Beds ⋅ 1 Baths ⋅ Waterfall Cove SubDv. ⋅ 32789 Zip Code
Charming 2-bedroom, 1-bath condo located in the heart of Winter Park. This well-maintained unit offers comfortable living with an open layout, ample natural light, and convenient access to shopping, and dining. Enjoy the community pool and beautifully landscaped grounds, perfect for relaxing or entertaining. Ideal for first-time buyers, investors, or anyone looking to enjoy the Winter Park lifestyle.

1695 Lee Road Unit C214, Winter Park
$745,000
3 Beds ⋅ 2 Baths ⋅ Northwood - Winter Park Oasis SubDv. ⋅ 32789 Zip Code
An incredible location close to Park Avenue, this freshly renovated home exudes modern style and the walkable lifestyle that Winter Park is known for. This timeless Florida ranch features one-level living and is in a charming downtown neighborhood that is fresh and turnkey. Experience an open living concept with seamless flooring and designer selections throughout creating great spaces and function. The kitchen features clean-lined, neutral-toned cabinetry with a large island topped with quartz counters and bar seating with gold-toned, oversized pendants that take center stage. The adjacent bar area includes a built-in pantry, open shelving and a wine refrigerator, adding a touch of luxury to your everyday life. Just beyond the kitchen/living room, you'll discover a fantastic dining area and two well-appointed bedrooms. The shared bath is fully renovated with current selections, making it a retreat for family and guests. A desirable split plan with owner's suite is on opposite side of the home, adorned with beautiful light and airiness. A space-saving built-in wardrobe lines one wall, while the en-suite bath showcases stunning design elements, including a walk-in shower, dual sinks and a private water closet. The backyard invites you out through clear glass sliders to a charming backyard with a brick patio and a fully fenced backyard, lined with bamboo, which offers the privacy you desire. Entertain with shaded dining and lounging on sunny days with newer retractable awning (2021) controlled by a convenient remote. Additional features that make this home stand out include a newer roof (2020), newer air conditioner (2020), plumbing updated 2018, electrical panel update (2023), new backyard sod and irrigation (2025), freshly painted, a two-car garage with a new electric car charger (2022), a custom workbench and storage cabinets added in 2021. And let's not forget the incredible location, a couple of blocks from Winter Park 9 Golf Course, Park Avenue, Winter Park Village and Saturday farmers market, with Whole Foods, Publix and the Enzian just minutes away, this home is your private oasis in the heart of Winter Park.

630 Northwood Circle, Winter Park
$360,000
3 Beds ⋅ 2 Baths ⋅ Killarney Circle SubDv. ⋅ 32789 Zip Code
RARE FIND! MUST SEE! PRIME LOCATION! NO HOA! Check out this 3 bedroom 2 bath gem in the heart of beautiful Winter Park. This home is conveniently located close to shopping, dining, medical. Only minutes from Downtown Orlando and only a short drive to any of the Orlando amusment parks and airport. Home has been used as a rental for many years. Roof is 2020. HVAC replaced 2021. Whether you are looking to occupy or an investor looking for your next investment, this is it! Schedule your showing now!

611 Ololu Drive, Winter Park
$1,850,000
4 Beds ⋅ 5 Baths ⋅ Flora Park 2nd Add SubDv. ⋅ 32789 Zip Code
Welcome home to 1612 Magnolia Avenue. Built by the renowned custom home builder Lundev, this beautifully crafted transitional residence blends thoughtful design with luxurious comfort. From its striking exterior to the serene backyard oasis, every detail is designed to impress even the most discerning buyer. Upon entry, a dedicated office sits just off the foyer with custom floor-to-ceiling cabinetry and dual workstations, perfect for working from home. Across the hall, the formal dining room offers an elegant setting for entertaining and connects to the kitchen through a temperature-controlled wine cellar with storage for more than 400 bottles. The chef’s kitchen is a culinary dream featuring top-of-the-line appliances, a spacious island ideal for food preparation and presentation, and an open concept that flows seamlessly into the family room. A cozy gas fireplace anchors the family room, which opens through French doors to the covered lanai. Enjoy year-round outdoor living with a fully equipped summer kitchen that includes a grill, Green Egg BBQ, refrigerator, and wraparound counter space for hosting while overlooking the sparkling pool. The backyard is a private sanctuary complete with a luxurious pool and a large cabana with a wood-burning fireplace. The first-floor primary suite offers peaceful views of the backyard and a spa-like bath with dual sinks, a soaking tub, and a separate shower leading to an oversized walk-in closet with built-in storage. A mudroom, laundry room, powder bath, and convenient pool bath complete the well-planned first floor. Upstairs, three additional bedrooms provide ample space for family or guests. Two bedrooms share a Jack and Jill bath, while the third enjoys its own private en suite. This home has been extensively upgraded, combining comfort, sophistication, and modern convenience. Ideally located on a tree-lined street in one of Winter Park’s most desirable neighborhoods, it is minutes from the Winter Park Racquet Club, Park Avenue’s shopping and dining, YMCA, top-rated hospitals, and excellent public and private schools. Do not miss this rare opportunity to own a home that truly has it all. Welcome to the best of Winter Park living.

1612 Magnolia Avenue, Winter Park
$1,650,000
4 Beds ⋅ 3 Baths ⋅ Stonehurst Estates SubDv. ⋅ 32789 Zip Code
Nestled on a magnificent oversized lot in the heart of Winter Park, this 4-bedroom, 3-bath home offers plenty of space and opportunity. The backyard is a true highlight, featuring a large swimming pool and additional green space tucked just beyond the back hedges, adding a sense of privacy and flexibility for the outdoor area. Inside, the home showcases hardwood floors that flow throughout the living room, dining room, kitchen, family room, and bedrooms, creating a warm and inviting feel. A spacious family room with a cozy fireplace serves as the centerpiece of the home, while French doors open onto a vaulted screened porch, perfect for unwinding or entertaining with a view of the backyard. The kitchen offers stone countertops, and recent updates to the electrical, plumbing, and roof provide peace of mind for the next owner. This property is ideal for someone looking to renovate or update to their personal taste, or even to build a new home on this generous lot. Its location is hard to beat, set on a nice and quiet Winter Park street close to Park Avenue’s shops and dining, Rollins College, top-rated schools, and the area’s many lakes and parks. It’s a wonderful investment in both lifestyle and location.

1915 Stonehurst Road, Winter Park
$1,129,000
3 Beds ⋅ 3 Baths ⋅ Winter Park Residential SubDv. ⋅ 32789 Zip Code
RARE OPPORUNITY to Experience refined living in the heart of Winter Park with this exceptional and spacious 3-bedroom, 3-bath END UNIT residence at the highly sought Douglas Grand. This unit INCLUDES A DEEDED STORAGE UNIT AND 3 PARKING SPACES. Combining timeless elegance with modern comfort, this spacious home features high ceilings, an open-concept design, and exquisite finishes throughout. The gourmet kitchen is perfect for entertaining, offering custom cabinetry, stone countertops, premium stainless-steel appliances. The primary suite is a serene retreat with a spa-style bath, dual vanities, a soaking tub, and an expansive walk-in closet. Two additional bedrooms provide ample space for guests, an office, or a den. Enjoy the convenience of three designated parking spaces and a deeded storage unit, providing both practicality and peace of mind to store those holiday accessories and more. Residents of The Douglas Grand enjoy secure building access and maintenance-free living just steps from Park Avenue’s upscale shops, fine dining, and cultural attractions. Building is very well maintained with newer roofs recently completed in the last few years. This rare offering captures the essence of Winter Park luxury — convenient and perfectly located.

100 S Virginia Avenue Unit 314, Winter Park
$1,599,900
5 Beds ⋅ 5 Baths ⋅ Lawndale SubDv. ⋅ 32789 Zip Code
New Construction – Carefully Curated by SGC Conctruction. Discover Modern Luxury in Winter Park's Latest Neighborhood, Winter Park Grove! Step into a world of refined living with this breathtaking new construction pool home, located in the vibrant heart of Winter Park. Just moments away from the eclectic energy of Park Avenue, this modern masterpiece seamlessly blends sophistication, style, and convenience — all within walking or biking distance of premier restaurants, cafés, boutique shops, and entertainment venues. Designed for both daily comfort and elevated entertaining, the open-concept floor plan boasts thoughtful design and high-end finishes throughout. Luxury details abound, including engineered wood floors featuring an elegant herringbone pattern in the foyer, smooth finish Level 4 drywall, and a cozy electric fireplace that enhances the spacious great room, accentuated by LED mood lighting in the coffered ceiling. The expansive gourmet kitchen is a chef’s delight, equipped with ceiling-height cabinets for ample storage and premium Thermador appliances, including a 36” gas cooktop, wall oven, built-in microwave, French door refrigerator, and a wine fridge — all complemented by sleek cabinetry and contemporary details. A beautiful dry bar adjacent to the kitchen provides extra space for coffee, wine, or entertaining guests. Offering four generous bedroom suites, this home includes a luxurious primary suite on the main level, along with a versatile second suite on the first floor, ideal for use as an office or guest retreat. Upstairs, two additional suites are connected by a flexible bonus room — perfect for a home office, gym, second living area, or even a fifth bedroom. Step outside to your private outdoor oasis, featuring a covered lanai with a fully-equipped summer kitchen (complete with grill, sink, and refrigerator drawers), and a sparkling pool adorned with travertine decking — perfect for year-round Florida entertaining. The elegant exterior showcases outdoor lighting and lush landscaping, along with a gas generator to ensure your home is always prepared for storm season.Don’t miss your opportunity to own this exquisitely crafted home in one of Orlando’s most sought-after neighborhoods. Schedule your private showing today and experience the pinnacle of luxury living in Winter Park! There are special builder incentives available right now- Call for details!!

1510 Miller Avenue, Winter Park
$195,000
1 Beds ⋅ 1 Baths ⋅ Winter Park Gardens Condo SubDv. ⋅ 32789 Zip Code
Located in the historic Winter Park Gardens community, this condo has been meticulously maintained and updated. Featuring an open and inviting layout that flows seamlessly into a spacious living room, ideal for entertaining or relaxing.The kitchen boasts modern appliances, ample cabinetry, and plenty of counter space. The expansive sunroom serves as your personal oasis, overlooking the courtyard pond and lush gardens—perfect for morning coffee or evening unwinding with stunning floor-to-ceiling views. The spacious primary bedroom serves as a tranquil retreat, complemented by a full bathroom. Move-in ready with a renovated kitchen, bathroom, and new air conditioner. As part of the vibrant 55+ Winter Park Gardens community, you'll enjoy resort-like amenities including a community pool, walking paths, a courtyard with a pond and beautifully landscaped grounds. This condominium embodies refined, low-maintenance living with the HOA covering essentials like water, trash, pool upkeep, and common areas, allowing you to focus on what matters most—enjoying life. Just a short walk to the iconic Park Avenue with its world-class restaurants, boutique shops, and entertainment; Rollins College; Mead Botanical Garden for nature lovers; and downtown Winter Park. Easy access to I-4, and Orlando International Airport (13.7 miles).

700 Melrose Avenue Unit D21, Winter Park
$8,950,000
7 Beds ⋅ 11 Baths ⋅ Windsong-Preserve Point SubDv. ⋅ 32789 Zip Code
In the exclusive community of Windsong on Lake Berry, this magnificent 1.6-acre gated Mediterranean estate is a private oasis. With over 11,000 square feet of living area and a beautifully landscaped lakefront lot, this residence offers an exceptional blend of elegance, charm and privacy rarely found in Winter Park. The home features seven spacious bedrooms and nine full and two half baths. Entertain in the all-glass conservatory, dedicated theater room with motorized seating and a fully equipped game room. Modern conveniences throughout including gas-powered generators, an elevator and dumbwaiter. Two above-garage apartments provide ideal accommodations for guests and family. Outdoors, enjoy an expansive covered lanai, infinity edge pool and spa, boat dock with jet ski lift, and a summer kitchen complete with wood-burning fireplace, gas grill, refrigerator and icemaker, all overlooking the beautifully landscaped yard and lake. With its private gated entrance, this home is a one-of-a-kind opportunity to enjoy all the amenities Winter Park and Windsong have to offer.

1120 Preserve Point Drive, Winter Park
$700,000
Karolina On Killarney SubDv. ⋅ 32789 Zip Code
A unique opportunity in unincorporated Orange County, these three contiguous residential lots, each approximately 0.15 acres, totaling 0.45 acres or 20,244 square feet, are offered together as a prime redevelopment site. Zoned R-2, this assemblage is positioned adjacent to some of Winter Park’s most vibrant retail and restaurant corridors, including Hollieanna Shopping Center, Winter Park Village, Park Avenue, Lakeside, Lakeside Crossing, and Palm Hills, all recently redeveloped or newly constructed. The property features two cleared lots and one parcel with an existing single-family residence, historically used as an income property. All parcels are being sold as vacant land, presenting flexible options for future residential development. City sewer is connected, with potential annexation into the city of Winter Park and rezoning possibilities. Proximity to Interstate 4, U.S. Highway 17-92, and major retail destinations enhances accessibility and long-term investment value. Buyer to verify all redevelopment and rezoning requirements with Orange County and the City of Winter Park.

2002 Karolina Avenue, Winter Park
$550,000
2 Beds ⋅ 2 Baths ⋅ Andalucia Apts SubDv. ⋅ 32789 Zip Code
Experience effortless luxury living just blocks from iconic Park Avenue in this stunning, fully renovated condo located in the heart of downtown Winter Park. Perfectly designed for a lock-and-leave lifestyle, this beautifully upgraded residence blends timeless elegance with modern convenience. Step into a beautifully designed foyer entry that opens to bright, open living spaces with treetop views from the screened lanai. Every inch of this home has been thoughtfully updated—featuring crown molding, designer light fixtures, removal of popcorn ceilings, updated wiring, and plantation shutters throughout. Major systems are also newer, with an HVAC system and water heater (2020) for peace of mind. Gourmet kitchen is appointed with quartz countertops, white shaker cabinets, stainless steel appliances, dramatic backsplash and under cabinet lighting. Custom built-ins in dining area for additional storage. Large Owner’s Suite offers two custom closets with built-in organizers and spa like bath with walk in shower. Spacious secondary bedroom. Renovated guest bath with modern finishes. Andalucia is a boutique community with just 20 owner-occupied units—no rentals, no pets—ensuring a peaceful, neighborly environment. Additional highlights of this condo include a private storage closet, one covered parking space + guest parking, elevator, well landscaped courtyard and patio, community laundry room, cable and internet. Walk to Park Avenue’s shops, restaurants, museums, and the Winter Park Golf Course, Morse Museum of Art, Central Park, Farmer’s Market and SunRail station. Enjoy vibrant culture and charming streets just steps from your door. This move-in ready condo offers the best of upscale Winter Park living—schedule your private tour today!

535 N Interlachen Avenue Unit 203, Winter Park
$372,400
4 Beds ⋅ 2 Baths ⋅ Magnolia Gardens Sub SubDv. ⋅ 32789 Zip Code
Welcome to 770 Carver Street in the highly sought after Winter Park, Florida! This charming three-bedroom, one-and-a-half-bath home offers nearly 1,300 square feet of versatile living space, brimming with potential. Whether you’re a potential homeowner or an investor/developer seeking your next opportunity, this property presents an ideal canvas to bring your vision to life. The home boasts a spacious layout with ample natural light throughout. The large, fenced-in backyard is a standout feature, offering the perfect foundation to create your own private oasis—whether you envision a tranquil garden, a play area, or an outdoor entertainment space. Located in one of Winter Park’s most sought-after neighborhoods, you’ll enjoy unparalleled convenience. The home is just minutes away from top-rated schools, shopping, dining, major highways, and world-renowned attractions. More photos coming soon! Don’t miss out on this incredible opportunity to own in a prime location with endless possibilities. Schedule your private showing today and make your home dreams a reality!

770 Carver Street, Winter Park
$475,000
3 Beds ⋅ 3 Baths ⋅ Orange Terrace SubDv. ⋅ 32789 Zip Code
What a great location - Ready for move in before the holidays! Don’t miss this impeccable classic Florida ranch, 3/2 with hardwood floors, PLUS bonus bath in utility! Large sunny living room with wood burning fireplace, dining room, renovated kitchen with granite counters and wood cabinetry. Large bedrooms with great closets and good storage. Updated hall bathrooms with tub/shower and pedestal sink and primary suite bath with stall shower. Lovely landscaped fenced yard with screened porch and large gazebo for entertaining! 2 car garage, plus workbench and large utility room with access to rear and side yard. Perfectly located in Winter Park near Lake Killarney with easy access to I-4, College Park, Maitland and Downtown Orlando. Bonus - Walk to E-Tennis for those tennis and pickleball enthusiasts!

260 Orange Terrace Drive, Winter Park
$775,000
Lakeview Terrace SubDv. ⋅ 32789 Zip Code
Discover a truly unique offering in the heart of Winter Park! This property, located at 1760 Bryan Avenue, is being offered along with the adjoining lots at 1770 and 1780 Bryan Avenue. While available together as a rare collection of three consecutive parcels, each lot is also being sold separately at individual prices, giving buyers the flexibility to purchase one, two, or all three. Together, these lots provide remarkable options for future use: Combine all three to create a spacious 200' x 127' estate lot Split into two 100' x 127' lots Or develop three individual 66.6' x 127' lots Use this premium property to build an estate-like home, design a family compound, or develop all three lots as spec homes—the possibilities are endless. Whether you’re envisioning a dream residence or an investment project, this is a rare chance in one of Winter Park’s most desirable neighborhoods. Ideally located just minutes from Phelps Park, Park Avenue’s shopping and dining, and top-rated schools, this offering combines convenience with exclusivity. Don’t miss the chance to secure one or more of these exceptional parcels in the heart of Winter Park.

1760 Bryan Avenue, Winter Park