Location: Winter Park
Do Not Show Listings
1695 LEE RD #C214, WINTER PARK, FL 32789
$115,000186 Days on yellowkey MLS ID: S5136332
4 Days Off yellowkey (back on 3/30/2026)
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 881 Built: 1966Monthly Fee: $572 Tax: $1,729 (2024)Community: Waterfall CoveCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,729
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: 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.
Listing is courtesy of: PROFESSIONAL REAL ESTATE TEAM (407-483-4964)
Listing Agent: Diana Perez (407-483-4964)
5418 ARDMORE DR, WINTER PARK, FL 32792
$450,00034 Days on yellowkey MLS ID: O6389781
1 Days Off yellowkey (back on 3/30/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1560 Built: 1980 Tax: $4,236 (2025)Community: Wrenwood Unit 3 3Rd AddSingle Family
Taxes:$4,236
Elementary School: Eastbrook Elementary
High School: Lake Howell High
Tax Year: 2025
Middle School: Tuskawilla Middle
Remarks: One or more photo(s) has been virtually staged. **WELCOME HOME** A generous .23 ACRE LOT, NO HOA, fresh UPDATES and SOLID CONSTRUCTION come together in this MOVE-IN READY 3-bedroom, 2-bath home in the desirable Wrenwood community of Winter Park! Thoughtfully maintained and upgraded, this property offers the timeless character and modern touches you have been searching for. ****Major improvements start with FRESH EXTERIOR PAINT (2026) and a NEW HURRICANE RATED GARAGE DOOR with complete operating system (2025), followed by the FULLY FENCED BACKYARD with NEW FENCING (2023). The home also features a NEW ROOF (2020), and the durable 25-year interior and exterior paint delivers peace of mind and long-term value. Inside, the home showcases TILE & WOOD FLOORING THROUGHOUT, versatile living spaces, crown molding and charming architectural touches like arched entryways that add warmth and personality. The large UPDATED KITCHEN is a true standout, designed with solid wood cabinetry (soft-close doors!), granite countertops, STAINLESS STEEL APPLIANCES, built-in pantry storage and elegant overhead cabinet accent lighting – creating a space that feels both stylish and functional for everyday living with family or entertaining friends. The layout offers spacious rooms and abundant storage, while the PRIMARY SUITE includes its own private en-suite bath and a WALK-IN CLOSET with a CUSTOM SHELVING SYSTEM. Additional upgrades include updated plumbing fixtures, electrical outlets and systems, plus DOUBLE GLAZED/DOUBLE HUNG WINDOWS that pop out for easy cleaning. Step outside to enjoy Florida living on the LARGE SCREENED LANAI overlooking the fully fenced backyard, offering plenty of room for pets, play or future outdoor additions. The property also includes a 10x12 hurricane-secured Hardi-board storage shed, new lawn and mulch, and separate potable and irrigation water meters for added efficiency. Built with brick façade over concrete block construction, this home delivers the solid feel and craftsmanship that’s hard to find today – paired with modern updates and undeniable charm! Located in the established Wrenwood neighborhood of Winter Park, with easy access to 426, 436 and SR 417 – you will enjoy convenient access to shopping, dining, parks, and all that the Central Florida area has to offer. A well-built, beautifully maintained home with thoughtful upgrades throughout ~ Ardmore Drive ~ is ready to welcome its next owner. Easy to show, call today to schedule your tour!
Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)
Listing Agent: Jenny Wemert (407-809-1193)
525 LAKEVIEW AVE, WINTER PARK, FL 32789
$1,390,000271 Days on yellowkey MLS ID: O6325165
Bed: 4 Bath: 4.5 Liv Area Sq Ft: 3253 Built: 2026 Tax: $2,814 (2024)Community: Killarney EstatesSingle Family
Taxes:$2,814
Elementary School: Killarney Elem
High School: Edgewater High
Middle School: College Park Middle
Remarks: Under contract-accepting backup offers. Under Construction. Renderings available soon. Brand-new custom construction on coveted Lakeview Avenue marries classic Winter Park charm with crisp, contemporary living. Behind its inviting façade you’ll find an airy two-story layout featuring four bedrooms and 4 ½ baths, including a full en-suite guest retreat on the main level. Three additional bedrooms share the upper floor with a bright loft that easily flexes as a playroom, office, or second lounge.The heart of the home is a chef-ready kitchen outfitted for serious cooking—double wall ovens, a dedicated cooktop, and generous countertop space—anchored by a spacious walk-in pantry and a convenient mudroom drop zone to keep daily life organized. Just beyond, a soaring great room centers on a built-in fireplace, while wide sliders open to a covered rear porch perfect for year-round alfresco dining. Upstairs, every bedroom enjoys direct or semi-private bath access, giving the residence the feel of four private suites, and a dedicated laundry room means no hauling baskets downstairs. Practical perks abound: an oversized two-car garage for gear and golf carts, impact-rated construction engineered to the latest Florida wind code, and full pre-wire rough-ins ready for your preferred appliance and lighting packages. All this sits minutes from Park Avenue’s dining and boutique shopping, Rollins College, and Winter Park’s famous chain of lakes. Schedule your private tour and discover the fresh, low-maintenance lifestyle waiting for you in one of Central Florida’s most sought-after neighborhoods. Final design and features subject to change.
Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)
Listing Agent: Marie Helen Ledbetter (407-286-4363)
311 E MORSE BLVD #6-3, WINTER PARK, FL 32789
$315,000142 Days on yellowkey MLS ID: O6362964
3 Days Off yellowkey (back on 3/30/2026)
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 570 Built: 1960 Tax: $3,758 (2025)Community: Whispering WatersCondo
Taxes:$3,758
Elementary School: Audubon Park K8
High School: Winter Park High
Middle School: Audubon Park K-8
Remarks: Under contract-accepting backup offers. Discover your new downtown Winter Park ground-floor pied-à-terre. Two blocks from Park Avenue, the 1960s mid-century modern Whispering Waters Condominiums are a Winter Park landmark. Your remodeled end-unit studio features an updated open kitchen with plentiful wood cabinets, ceramic tile flooring throughout, new dual-pane windows, a stylish updated bathroom with a step-in shower, and wood built-ins in the living room. Open to the living room is a sleeping alcove that accommodates a queen-size bed. An additional 9’ by 6’ enclosed room could be used as a bedroom, an office, or a lounging space. With easy access from your new pad to both Interlachen Avenue and Morse Boulevard, your downtown Winter Park adventures await.< Included is one assigned parking space in the secured underground garage, where you will also find a community laundry room. Enjoy mail and package delivery directly to your door. Electricity, gas, water, and sewer are included in your monthly condo fee for worry-free simplicity. Community amenities include: • Community swimming pool; • Lakeview social club room; • Outdoor patios overlooking Lake Osceola; • On-site management. Whispering Waters is a 55+ Community.
Listing is courtesy of: FLORIDA ONE REAL ESTATE LLC (407-599-7070)
Listing Agent: Richard Traynor (407-619-6247)
2500 LEE RD #219, WINTER PARK, FL 32789
$164,000257 Days on yellowkey MLS ID: O6332524
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 851 Built: 1969Monthly Fee: $360 Tax: $2,392 (2024)Community: Lakeside Manor Apts CondoCondo
Taxes:$2,392
Remarks: Welcome to life on Lake Killarney, one of Winter Park’s most sought-after lakefront communities! This charming 2-bedroom, 1-bathroom condo offers an unbeatable location and resort-style amenities—perfect for those seeking the true Florida lifestyle.Enjoy direct access to Lake Killarney, where residents can take advantage of boat slips available at a low cost on a first-come, first-serve basis, as well as a private boat launch, a brand-new dock with covered over-water seating, a lakeside pool, and a clubhouse. The beautifully manicured green spaces and quiet courtyard areas create a peaceful, community-oriented atmosphere.Inside, this move-in ready unit has been freshly painted throughout and features new carpeting. The kitchen has been tastefully refreshed and offers plenty of cabinet space. An assigned parking space is located just steps from the unit, and there's an on-site laundry facility plus a private storage unit for added convenience.Tucked away yet close to it all, you’re just minutes from the shops and restaurants of Winter Park, with easy access to I-4 and other major roadways. Residents love living here—units don’t come available often, so don’t miss your chance to call this lakeside gem home!
Listing is courtesy of: SUNDIAL REAL ESTATE LLC (407-601-2200)
Listing Agent: Nicole Van Treese (407-462-9050)
1523 GOLFSIDE DR, WINTER PARK, FL 32792
$649,00019 Days on yellowkey MLS ID: O6392204
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1936 Built: 1979 Tax: $3,090 (2025)Community: Greenview At Winter PinesSingle Family
Taxes:$3,090
Elementary School: Brookshire Elem
Middle School: Glenridge Middle
Remarks: Under contract-accepting backup offers. POOL HOME, nestled along the 14th fairway of Winter Park Pines Golf Course (WP18). A peaceful retreat with no rear neighbors—ideal for tranquility and privacy. Offering 1,936 square feet, four bedrooms, two bathrooms and an inside utility room, this is a hard-to-find gem in Winter Park. Perfectly situated in a tree-lined community overlooking the golf course. Upon entering, you are greeted by a spacious foyer that leads into a formal living room and then transitions into a formal dining area. The updated kitchen includes a cozy breakfast nook. The inviting family room features vaulted ceilings, beams and a fireplace creating a welcoming atmosphere for gatherings and relaxation. The primary suite boasts his-and-her closets, enhancing functionality. This home is zoned for Brookshire Elementary, Glenridge Middle, and Winter Park High School. Recent updates include AC (2014), Windows (2020), New Roof (2025), New Electrical Panel (2025), and Re-pipe (2026). WELCOME HOME!
Listing is courtesy of: BALDWIN PARK REALTY LLC (407-986-9800)
Listing Agent: Brian Cirillo (321-231-1068)
607 ELLEN DR, WINTER PARK, FL 32789
$1,550,000176 Days on yellowkey MLS ID: O6354269
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 2812 Built: 2025Monthly Fee: $76 Tax: $4,224 (2024)Community: Lake Killarney ShoresSingle Family
Taxes:$4,224
Remarks: Discover sophisticated modern living at 607 Ellen Drive, a stunning new construction home by the acclaimed Lazarus Homes in the heart of Winter Park. This impeccably designed 2,812-square-foot residence showcases contemporary architecture with clean lines, high ceilings, and an abundance of natural light throughout. The open floor plan seamlessly connects living spaces, creating an ideal setting for both everyday life and elegant entertaining. The chef's kitchen is a true showpiece, featuring top-of-the-line Monogram appliances, a sleek Ruvati sink, built-in oven and microwave, and a professional gas range. Gorgeous Taj Mahal Quartzite countertops provide both beauty and durability, while thoughtful design elements include the option for a full-height wine refrigerator or additional cabinetry to suit your lifestyle. The living room offers a modern ambiance with an electric fireplace and expansive glass sliders that open to a covered lanai overlooking your private pool—perfect for Florida's indoor-outdoor lifestyle. For those who love to entertain, the home has been pre-stubbed for an optional outdoor kitchen. The luxurious first-floor primary suite provides a private retreat with a spa-inspired en suite bath featuring a double sink vanity, walk-in shower, soaking tub, and an oversized walk-in closet complete with custom built-ins and convenient washer and dryer hookups. Upstairs, the home continues to impress with a generous bonus room, a sophisticated loft with glass walls, three additional bedrooms, two full baths, and a second laundry area for ultimate convenience. A dedicated pool bath adds another layer of functionality for poolside enjoyment. Nestled in the desirable Lake Killarney Shores community, this home offers the perfect blend of tranquility and accessibility. Residents enjoy a low HOA, private boat launch access to Lake Killarney, and the convenience of being within walking distance to Winter Park's renowned restaurants, boutiques, and cultural attractions. This is move-in ready modern luxury at its finest.
Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)
Listing Agent: Kelly Price (407-645-4321)
744 CORNWALL RD, WINTER PARK, FL 32792
$715,000257 Days on yellowkey MLS ID: O6332168
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1968 Built: 1968 Tax: $5,359 (2024)Community: Winter Park PinesSingle Family
Taxes:$5,359
Remarks: Welcome to your dream home! This exceptional 4-bedroom residence features a desirable split floor plan, offering both privacy and functionality. Nestled on a quiet corner lot in the serene Winter Park Pines community, this property is just a few steps away from the scenic Cady Way Trail, perfect for outdoor enthusiasts.This home is surrounded by recreational opportunities, including a refreshing pool, pickleball courts, and miles of trails for jogging, biking, or leisurely strolls. Enjoy the outdoors while being in close proximity to shopping, dining, and the celebrated Winter Park schools.Recent updates make this home truly special. The new A/C system and upgraded electrical panel—complete with room for additional breakers—ensure your comfort and convenience. The manifold system has also been updated, and the roof was newly installed in 2018 for peace of mind.Additionally, half of the windows have been replaced with high-quality Anderson windows, enhancing both energy efficiency and natural light.Don’t miss the opportunity to own this well-maintained home in a vibrant neighborhood that perfectly balances recreation and relaxation. Schedule your showing today!
Listing is courtesy of: VERSALIS REALTY POWERED BY SELLSTATE (407-608-9593)
Listing Agent: Tammy Cuddy (407-608-9593)
259 E CANTON AVE #259, WINTER PARK, FL 32789
$629,00036 Days on yellowkey MLS ID: O6389246
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1040 Built: 1971 Tax: $3,603 (2025)Community: Village Winterset IncCondo
Taxes:$3,603
Remarks: Experience elevated living in this rare fifth-floor corner residence, perfectly positioned just one block from the iconic Park Avenue in the heart of Winter Park. With sweeping views of the downtown skyline and abundant natural light from multiple exposures, this residence offers an exceptional blend of comfort, elegance, and location. The thoughtfully updated kitchen features custom shaker cabinetry, granite countertops, and stainless-steel appliances, seamlessly connecting to the spacious living and dining areas. A charming sunroom provides the perfect setting for morning coffee, reading, or enjoying the city views. The generously sized primary suite offers a peaceful retreat, complete with an updated bath and a large walk-in closet with custom built-ins. The second bedroom has been thoughtfully opened to create a stylish office or den, ideal for working from home or relaxing with guests. Refined interior details include crown molding, bamboo flooring, and abundant natural light throughout, creating a warm and sophisticated atmosphere. Residents enjoy the security and convenience of a well-maintained mid-rise building featuring secure key entry, guest call box access, and a welcoming lobby. Perfectly suited for a lock-and-leave lifestyle, this residence is just steps from Park Avenue’s boutiques, acclaimed restaurants, museums, cafés, and the Winter Park Golf Course. Additional features include: • Private storage unit • Covered carport parking space • Guest parking and community pool. An exceptional opportunity to enjoy refined living in one of Central Florida’s most desirable locations. Please note: NO RENTALS, NO PETS.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Mary Colton (407-222-7388)
2423 VIA SIENNA, WINTER PARK, FL 32789
$2,200,00040 Days on yellowkey MLS ID: O6386867
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 3472 Built: 1990 Tax: $18,918 (2026)Community: Cinnamon ShoresSingle Family
Taxes:$18,918
Elementary School: Dommerich Elem
Tax Year: 2026
Middle School: Maitland Middle
Remarks: Welcome to 2423 Via Sienna, gracefully positioned on a quiet cul-de-sac in the heart of Winter Park. This charming, established enclave is just moments from the Winter Park Racquet Club, Phelps Park, the YMCA, and the renowned boutiques and dining of Park Avenue. This exceptional four-bedroom, three-and-a-half-bath pool residence has been taken to the studs and masterfully reimagined with timeless finishes and thoughtful design throughout. Upon entry, soaring ceilings and expansive windows create a light-filled, open interior ideal for both everyday living and elegant entertaining. The living and dining spaces are accented by tongue-and-groove ceilings, a gas fireplace, and bespoke built-ins, flowing seamlessly into a sun-drenched sunroom destined to become a favorite retreat. Chicago brick flooring, fixed glass windows, and accordion doors frame serene views of the private backyard oasis. The gourmet kitchen is both stunning and functional, featuring custom soft-close cabinetry, quartz countertops, floating shelving, exquisite millwork, and a full suite of Thermador appliances. A generous 4.9-by-10-foot island with storage on both sides anchors the space, complemented by a cozy breakfast nook and built-in bar. French doors provide effortless indoor-outdoor connection. Just beyond, a thoughtfully designed mudroom and pool bath with Chicago brick flooring offers convenient access to the pool area. A spacious first-floor bedroom—ideal as a guest suite, office, or den—along with a full bath completes the main level. Upstairs, the luxurious primary suite offers a private sanctuary with dual walk-in closets and a spa-inspired bath featuring separate vanities, soaking tub, steam shower, and private water closet. Two additional bedrooms share a well-appointed Jack-and-Jill bath with individual vanity areas for comfort and privacy. The expansive laundry room adds charm and practicality with a retro sink, built-in ironing board, and abundant storage. The tranquil backyard is designed for quintessential Florida living, showcasing a beautifully resurfaced pool surrounded by lush landscaping—perfect for entertaining or quiet relaxation. Additional highlights include engineered hardwood flooring throughout, designer lighting, a wrought-iron staircase, new baseboards and crown molding, fresh interior and exterior paint, newer roof (2023), two HVAC systems (2022 & 2023), and an oversized two-car garage with dedicated workshop space. Located within highly regarded A-rated schools.
Listing Agent: Wendy Williams Crumit (321-356-8590)
3204 NETHERWOOD, WINTER PARK, FL 32792
$299,99965 Days on yellowkey MLS ID: O6380637
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 1056 Built: 1983 Tax: $3,426 (2024)Community: Coronation AddHalf Duplex
Taxes:$3,426
Remarks: Discover this beautifully renovated 2-bedroom, 1.5 -bathroom villa in the heart of Winter Park! Nestled on a private cul-de-sac lot with no HOA, this home has been completely upgraded to offer modern comfort and style. Step inside to luxury vinyl flooring throughout, an open-concept living space, and a sleek kitchen with stainless steel appliances. The high-end bathroom remodel adds a spa-like touch, while the spacious bedrooms provide a cozy retreat. The highlight? A brand-new private pool, perfect for unwinding or entertaining in your own backyard oasis! Located just minutes from downtown Winter Park’s shopping, dining, and entertainment, with easy access to the airport, UCF, and major attractions. Whether you're looking for a starter home, investment property, or vacation retreat, this home is a rare find. Furnishings are negotiable. Schedule your showing today!
Listing is courtesy of: WATSON REALTY CORP. (407-589-1600)
Listing Agent: Renee Anthony (407-603-5935)
2020 VIA TUSCANY, WINTER PARK, FL 32789
$4,195,00020 Days on yellowkey MLS ID: O6394117
Bed: 4 Bath: 4.5 Liv Area Sq Ft: 4665 Built: 2026 Tax: $12,585 (2025)Community: TuscaniaSingle Family
Taxes:$12,585
Remarks: PRESTIGIOUS VIA TUSCANY NEW CONSTRUCTION. If location was a lottery ticket, you just hit the jackpot!!! Welcome to a masterpiece of modern elegance in the heart of the Winter Park Vias. Crafted by the renowned Element Home Builders, this stunning 4,665 sq. ft. estate offers an unparalleled blend of sophistication and comfort. The expansive open-concept floor plan features 5 generous bedrooms, 4.5 luxurious baths, and a dedicated executive office. At the heart of the home, a gourmet chef's kitchen flows seamlessly into a light-filled great room, perfect for grand-scale entertaining. Step outside to your private sanctuary: a brand-new custom pool and a sprawling covered lanai featuring a cozy outdoor fireplace. Situated on a premier corner lot with a brick-lined street, you are just steps away from the Winter Park Racquet Club and minutes from the world-class dining and shopping of Park Avenue. Experience the pinnacle of Winter Park living in a home designed for the most discerning buyer.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Mauro Costa (321-231-6800)
3207 LOWNDES DR, WINTER PARK, FL 32792
$495,00075 Days on yellowkey MLS ID: O6362285
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2028 Built: 1967 Tax: $4,172 (2024)Community: Georgetown EstatesSingle Family
Taxes:$4,172
Elementary School: Lakemont Elem
Remarks: Easy access to all of Winter Park, UCF, and south Seminole County from this convenient, central location! If you've been searching for a spacious pool home with plenty of space for playing, entertaining, or even working from home -- you've found it here! When you walk in, you'll appreciate the intuitive flow of living space into the kitchen, with built-in eating space. Off of the kitchen, you'll find a bonus space (perfect for an office or home gym) as well as a large indoor laundry room/mudroom, and the converted garage which is ideal for a playroom or secondary living space. On the other side of the home, 2 secondary bedrooms, an oversized hall bathroom, and a primary with en suite bath. There are additional touches that go a long way, too, including the custom plantation shutters throughout the home and updated countertops in the kitchen. Much of your time will be spent in the backyard, enjoying a fenced in pool, screened porch, new custom shed (2025), and fully fenced yard with turf play area. Systems in the home have been well maintained: roof (2017), HVAC (2017), tankless gas water heater (2018), and brand new electrical updates (2026). The home was also re-plumbed in 2008.
Listing is courtesy of: MILLER GRANT AND COMPANY (407-399-6031)
Listing Agent: Courtney Pelfrey (407-454-0538)
1914 BONANZA CT, WINTER PARK, FL 32792
$430,000130 Days on yellowkey MLS ID: O6365516
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1727 Built: 1968 Tax: $4,503 (2025)Community: Eastbrook Sub Unit 13Single Family
Taxes:$4,503
Remarks: SELLER MOTIVATED! Get ready to fall in love with this stunning Winter Park home! Tucked away in a peaceful cul-de-sac, this fully renovated 3-bedroom, 2-bath beauty blends modern style with everyday comfort. Step into the family room and instantly feel the openness of the bright, airy layout. The open floor plan creates a seamless flow from the living area to the brand-new kitchen, making the entire space feel spacious and inviting. Luxury vinyl flooring runs throughout the home, while quartz countertops sit elegantly atop all-new cabinetry. The grand center island pairs perfectly with the custom-built dry bar, complete with open shelving and extra cabinet storage, an entertainer’s dream! All brand-new stainless steel appliances are included. Just off the kitchen sits the light-filled Florida room, wrapped in oversized windows and sliding glass doors that flood the home with natural sunshine year-round. Both bathrooms have been tastefully updated with new tile, flooring, gold finishes, and beautiful new vanities. With a 2022 roof, two-car garage, fresh interior and exterior paint, and thoughtful upgrades throughout, this home delivers the peace of mind and elevated living you’ve been looking for. Don’t miss out, your Winter Park retreat is waiting! Schedule your showing today!
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Linda Jokbengboon (336-404-8871)
1120 PALMER AVE, WINTER PARK, FL 32789
$3,800,00055 Days on yellowkey MLS ID: O6376319
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 3413 Built: 1951 Tax: $20,754 (2024)Community: 3223171-3223171Single Family
Taxes:$20,754
Remarks: Miami Beach/Coral Gables meets Winter Park high-end luxury for today's upscale lifestyle. Phil Kean completely re-imagined this 3400 sq ft one story home from top to bottom leaving virtually nothing untouched! If you are looking for one level, indoor-outdoor living, all of the most up-to-date Bells and Whistles, in a #10 location,on a private oversized lot with circular driveway, minutes to Downtown Park Avenue, nestled among some of the most beautiful waterfront mansions in all of Winter Park, this will blow your socks off! Available to tour by appointment only. This is a show home for the International Builders Show, now completed and ready to show to the world. Understated elegance This one is not to be missed!
Listing is courtesy of: PHIL KEAN REAL ESTATE LLC (407-982-2265)
Listing Agent: Brad Grosberg (321-439-1494)
512 N LAKEMONT AVE, WINTER PARK, FL 32792
$500,00026 Days on yellowkey MLS ID: O6392353
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1413 Built: 1955 Tax: $2,136 (2025)Community: Eastgate SubSingle Family
Taxes:$2,136
Remarks: Set on an oversized corner lot in one of the most desirable pockets of Winter Park, this 3-bedroom, 2-bath pool home blends character, location, and opportunity. The backyard is a standout feature, with a resurfaced pool finished in Tahoe Blue PebbleTec and positioned for open sky views, a rare find in a neighborhood known for its mature tree canopy. It creates a bright, inviting outdoor space that feels both private and expansive. Inside, the home has been thoughtfully updated while still leaving room for your own design vision. The layout offers comfortable living spaces with plenty of natural light and flexibility for everyday living or entertaining. Convenience is a major highlight. Located near top-rated schools, including Lakemont Elementary School, Maitland Middle School, Winter Park High School, and just minutes from local favorites like Park Avenue, Rollins College, and the Cady Way Trail. Nearby access to the SunRail adds another layer of accessibility. This location delivers a strong mix of lifestyle and connectivity, with dining, shopping, parks, and daily essentials all close by. Offered with clear motivation due to relocation, this is a rare chance to secure a well-located pool home with long-term upside in one of Central Florida’s most established communities.
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: David Plasencia, Llc (407-579-9369)
670 WILLIAMS DR, WINTER PARK, FL 32789
$2,995,00078 Days on yellowkey MLS ID: O6376953
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 4091 Built: 2016 Tax: $15,321 (2025)Community: Park GroveSingle Family
Taxes:$15,321
Remarks: This stunning custom residence built by respected Winter Park Builder Charles Clayton blends classic elegance with refined modern comfort, offering seamless indoor–outdoor living and impeccable craftsmanship throughout. From the manicured lawn and stately traditional exterior to the welcoming front porch with old Detroit brick, the home’s curb appeal sets a tone of understated luxury, all wrapped in an elegant exterior. A foyer with extensive custom molding immediately captures attention, with sightlines extending to the private backyard and pool which creates a natural flow between interior living spaces and the outdoor retreat. Flanking the foyer, a richly detailed private study features custom millwork and a built-in bookcase, while the formal dining room provides an elegant space for entertaining. Expansive family room/dining area offers extensive molding, a gas fireplace, surround sound, and a wall of French doors which open to a covered Detroit Brick porch, creating a natural flow between interior living spaces and the outdoor retreat including a porch and pool. The space easily accommodates a large casual dining area and opens seamlessly to the kitchen. The light-filled chef’s kitchen showcases extensive marble surfaces, a Sub-Zero refrigerator, large farmhouse sink, and an open layout ideal for gathering. The main-level primary suite is a private retreat with direct porch access, dual walk-in closets. The primary bath features marble finishes, a glass-enclosed shower, pedestal soaking tub, and dual vanities. A spacious mudroom, large laundry room, and pantry area sit just off the kitchen, complete with a half bath and convenient access to the garage and porch. The two-car garage includes additional storage, complemented by a brick driveway. Upstairs, a central stair hall opens to an upstairs Family/Kid’s Gathering/Game Area. Bedroom 2 functions as a second primary-style suite, while bedroom 3 is a private suite with its own sitting area. Bedrooms 4 and 5 share a Jack-and-Jill bath, providing flexible space for family or guests. There is an upstairs storage room. Outdoor open pool with living is equally impressive. This exceptional home offers the ideal balance of architectural character, luxury finishes, engineered wood floor and a floor plan designed for comfort, privacy, and unforgettable gatherings.
Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)
Listing Agent: Brian Mitnik (407-421-2832)
668 OVERSPIN DR, WINTER PARK, FL 32789
$875,00026 Days on yellowkey MLS ID: O6392301
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2509 Built: 2018 Tax: $11,633 (2025)Community: Dubsdread HeightsSingle Family
Taxes:$11,633
Elementary School: Princeton Elem
Remarks: One or more photo(s) has been virtually staged. A contemporary, beautifully finished home offering standout value in one of Winter Park’s most coveted zip codes. With more than 2,500 square feet of bright, open living space, this property features a sleek fireplace, a large pantry area, a designer kitchen, and a massive two-car garage. The private primary suite sits upstairs along with additional bedrooms, a versatile loft, and a conveniently placed laundry room. A first-floor guest suite adds flexibility for visitors or a dedicated workspace. Outside, a spacious backyard and custom gazebo create an inviting place to unwind. Zoned for Princeton Elementary and positioned for quick, easy access to everything College Park and Winter Park have to offer, this home delivers rare quality and exceptional value for 32789. This home is available immediatly.
Listing Agent: Kris Kennedy (813-947-3509)
1807 HAMMERLIN AVE #G, WINTER PARK, FL 32789
$580,00029 Days on yellowkey MLS ID: O6391277
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1818 Built: 2006 Tax: $6,197 (2025)Community: Terrazo Del SolCondo
Taxes:$6,197
Remarks: Welcome home to this beautifully updated two-story end-unit, ideally located just steps from Michelin-star dining, local boutiques, and the vibrant East End Market. On weekends, enjoy leisurely strolls to the area’s popular farmers markets and neighborhood events. Situated in the heart of Winter Park, this residence offers the perfect blend of lifestyle, convenience, and charm in one of Orlando’s most sought-after communities. Designed for both everyday comfort and effortless entertaining, the first floor features an open-concept kitchen and living area filled with abundant natural light, along with a convenient half bath—ideal for hosting guests. Upstairs, the spacious primary suite boasts a private ensuite bathroom, walk-in closet, and a newly refinished balcony—perfect for morning coffee or evening cocktails. Two additional bedrooms provide generous space and share access to a second balcony, creating a seamless indoor-outdoor living experience. Recent upgrades include a new dishwasher and smart refrigerator (2022), new water heater (2025), refinished front balcony (2025), new roof, and new carpet upstairs (2026). Updated light fixtures and primary bedroom flooring within the last five years add a modern touch throughout. The $400 monthly HOA fee includes landscaping and insurance, offering low-maintenance living and added peace of mind. Zoned for some of Orlando’s top-rated schools and walking distance from the new Audubon Park K-8 School, this home presents a rare opportunity to enjoy the very best of Winter Park living. Don’t miss your chance to call this exceptional property home.
Listing is courtesy of: ALL REAL ESTATE & INVESTMENTS (407-917-8206)
Listing Agent: Courtney Dietch (407-952-3779)
2550 VENETIAN WAY, WINTER PARK, FL 32789
$2,450,00040 Days on yellowkey MLS ID: O6388219
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 5051 Built: 2008 Tax: $16,724 (2024)Community: Maitland Shores First AddSingle Family
Taxes:$16,724
Remarks: Chain of Lakes Water- Front Home with Private Boat Dock, Winter Park Luxury Living. Step into your future with this extraordinary custom built residence, inspired by the artistic richness of Fernando Botero. From your back lanai, step directly onto your private, custom boat dock featuring a covered, remote-operated boat lift, and cruise the Venetian Canal with direct access to WinterPark’s exclusive Chain of Lakes-Lake Virginia, Lake Mizell, Lake Osceola, Lake Maitland, Lake Nina, and Lake Minnehaha. Morning sunrises and golden afternoon sunsets create unforgettable moments to enjoy privately or share with family and friends. Built in 2008, this exceptional home welcomes you with a stunning rotunda accented by stained glass panels, setting the tone for the refined design found throughout. Vaulted recessed ceilings enhance the open floor plan, filling the home with natural light and architectural elegance. Thoughtfully curated details and custom finishes are showcased in every space. Offering approximately 5,051 square feet, the home features four spacious bedrooms, each with its own en suite bathroom. The owner’s suite is a private retreat with picturesque canal views and luxurious built-in features. The spa-inspired owner’s bath includes dual vanities, designer textiles, strategic lighting, expansive walk-in closets, a steam shower with dual stations and multiple shower heads, a Jacuzzi tub, bidet, linen storage,and a private water closet. Designed for effortless entertaining, the gourmet chef’s kitchen is both functional and beautiful. Highlights include an oversized working island, high-top bar seating,Thermador gas range,Thermadore double ovens,Thermadore refrigerator, wine cooler, hidden lighted walk-in pantry and multiple prep areas. The kitchen flows seamlessly into the formal dining room and the expansive great room, which showcases floor-to-ceiling views of the lushly landscaped backyard, paver patio and serene Venetian Canal water view. A stunning library with floor-to-ceiling canal views features a custom gas fireplace and built-in shelving, perfect for displaying books and treasured collections. The first floor features a convenient half bath adjacent to the laundry room, along with a lovely powder room ideal for guests. Upstairs, a striking staircase leads to three additional bedrooms and two bathrooms. One bedroom room has a private en-suite bathroom and the other bedrooms share an adjoining en- suite bath. There are two oversized, versatile gathering spaces complete with a built-in wet bar and beverage refrigerator. A spacious living area overlooks the canal and opens to an upper-level lanai-ideal for outdoor entertaining. This level also includes a home theater and flexible space suitable for an additional bedroom, office, or recreation room. Location is unmatched. Situated in the heart of Winter Park, this home offers easy access to both Winter Park and Maitland amenities. Enjoy Park Avenue dining, shopping, art festivals, farmers markets, outdoor concerts, scenic walking and biking trails, and beautiful green spaces. Zoned for top rated OCPS schools: Dommerich Elementary, Maitland Middle School, and Winter Park High School. This remarkable Winter Park Canal home combines timeless style, exceptional craftsmanship, private dock access, Venetian Canal frontage, and direct connection to the Winter Park Chain of Lakes-all in one of Central Florida’s most sought-after locations.
Listing is courtesy of: PALM PROPERTIES OF CF, INC. (407-467-0020)
Listing Agent: Felicia Donatelli (407-467-0020)
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