Location: Winter Park
Do Not Show Listings
1000 S SEMORAN BLVD #805, WINTER PARK, FL 32792
$174,70040 Days on yellowkey MLS ID: O6392099
REDUCED by $5,000 (2.8%) on 04/13/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1003 Built: 1969Monthly Fee: $355 Tax: $1,111 (2025)Community: Golfside Villas CondoCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,111
Elementary School: None
High School: Winter Park High
Tax Year: 2025
Middle School: Glenridge Middle
Remarks: Beautifully updated condo in a prime Winter Park location! This move-in ready unit features a beautifully renovated kitchen, updated bathrooms, and tile flooring throughout, offering a modern and low-maintenance living space. Ideally situated on South Semoran Blvd, you’ll love the convenience of being just minutes to Baldwin Park, Full Sail University, UCF, and Downtown Winter Park, with easy access to shopping, dining, and major roadways. One of the few units in the community featuring a screened patio AND an in-unit washer and dryer, providing added convenience and everyday ease. Low HOA fees make this an excellent opportunity for both homeowners and investors alike. Whether you're looking for a primary residence or an income-producing property, this condo stands out with its upgrades, location, and unique features. NEW ROOF April 2026! Call today to schedule your private showing.
Listing is courtesy of: SHAWFIELD REALTY GROUP (407-963-7749)
Listing Agent: Carrie Sue Shawfield (407-963-7749)
1781 INDIANA AVE #A, WINTER PARK, FL 32789
$545,00078 Days on yellowkey MLS ID: O6381195
REDUCED by $20,000 (3.5%) on 04/14/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1616 Built: 2008Monthly Fee: $464 Tax: $6,026 (2024)Community: Las Casas De IndianaTownhouse
Taxes:$6,026
Elementary School: Killarney Elem
High School: Edgewater High
Tax Year: 2024
Middle School: College Park Middle
Remarks: Welcome to 1781 Indiana Avenue, Unit A, a beautifully appointed three-bedroom, two and a half bathroom townhouse nestled in the heart of Winter Park. This inviting residence offers the perfect blend of comfort and convenience, featuring a spacious two-car garage and a private courtyard ideal for morning coffee, outdoor dining, or relaxing in the Florida sunshine. Inside, the thoughtfully designed floor plan provides generous living spaces, well-proportioned bedrooms, and an effortless flow for everyday living and entertaining. Located just minutes from Winter Park’s renowned shopping, dining, parks, and top-rated schools, this home presents an exceptional opportunity to enjoy low-maintenance living in one of Central Florida’s most desirable neighborhoods.
Listing is courtesy of: CARLISLE REALTY, LLC (407-557-4024)
Listing Agent: James Rouadi (407-557-4024)
541 W CANTON AVE, WINTER PARK, FL 32789
$2,800,00040 Days on yellowkey MLS ID: O6389829
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3553 Built: 2024 Tax: $4,692 (2024)Community: Winter ParkSingle Family
Taxes:$4,692
Elementary School: Lakemont Elem
Middle School: Maitland Middle
Remarks: Timeless elegance meets boutique craftsmanship at 541 W Canton Ave., an exceptional new construction home by Urban Perch, proudly featured in the 2025 Parade of Homes Orlando. Near Winter Park’s iconic Park Avenue, this French Quarter-inspired residence blends historic charm and rich character with elevated modern living and a refined sense of calm. From its dormer windows and custom-carved wood entry door, to its charming striped awnings and the flicker of gas lanterns, every detail of the exterior is carefully curated. Classic marble-paved patios frame the home, and a courtyard-style pool with fountain and sandblasted marble decking invites quiet relaxation or festive gatherings. Inside, soaring ceilings, beautiful hardwood floors and immersive color-drenched rooms create an inviting space that is luxurious but unpretentious, bold yet serene. The stunning staircase features a custom wrought-iron railing with an antique finish, offering a striking architectural focal point. The chef’s kitchen, a culinary sanctuary and social hub, is complete with graphite La Cornue range and pot filler, Monogram paneled refrigerator, custom plaster hood, quartzite countertops and backsplash, and grand center island that opens to a gathering room with a gas fireplace. This more relaxed living area flows effortlessly through French doors to the pool and patios, creating an ideal indoor-outdoor lifestyle. A butler’s pantry with a second refrigerator, cabinetry and prep space adds functionality, while the formal dining room, living room, and bar area with sink and built-in beverage cooler are ideal for entertaining. A beautiful downstairs powder bath features designer wallpaper, elegant sconces and custom cabinetry. The upstairs primary suite offers spa-like serenity, including a wet room complete with soaking tub framed by a picture window. Three additional bedrooms include one with an en-suite bath, while the other two share a hallway-accessible bath with double vanity and walk-in tiled shower. This masterpiece set in the heart of Winter Park, thoughtfully surrounded by lush landscaping and carefully placed privacy screens, offers polish and presence in an ideal location.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Bianca Khoury (407-797-1121)
633 BALMORAL RD, WINTER PARK, FL 32789
$1,795,000192 Days on yellowkey MLS ID: O6353491
3 Days Off yellowkey (back on 3/24/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2674 Built: 1968 Tax: $10,321 (2024)Community: Kenilworth Shores Sec 06Single Family
Taxes:$10,321
Elementary School: Brookshire Elem
Remarks: Under contract-accepting backup offers. 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 boat 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-a-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 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.
Listing Agent: Mick Night (407-629-4446)
2612 ROXBURY RD, WINTER PARK, FL 32789
$630,000140 Days on yellowkey MLS ID: S5139410
Bed: 5 Bath: 0.0 Liv Area Sq Ft: 2472 Built: 1957 Tax: $6,425 (2024)Community: Glencoe SubSingle Family
Taxes:$6,425
Remarks: SELLER MOTIVATED!! Potential of an extra one percent for closing costs, just ask your agent!! A FULLY MODERNIZED 5-bedroom, 3-bathroom home offering Modern style, flexibility, and comfort and its own ATTACHED 2bed/1 Bath IN-LAW SUITE!!! Step inside to an open and airy layout featuring Luxury vinyl plank flooring, fresh neutral paint, and large windows that fill the home with natural light. The upgraded kitchen is a true showstopper — boasting shaker cabinets, quartz countertops, subway tile backsplash, and stainless steel appliances with stylish hardware accents. Located just a 10 minute walk to Lake Killarney and a 3 minute walk to Killarney Elementary School! What is even more fantastic is the distance to I-4 is literally just 2 minutes away for fast and convenient travel to and from downtown Orlando and just 10 minutes from Park Avenue Winter Park!! So many restaurants, parks, local shops and family activities, Especially during the holidays!! Come see this home with potential income and your own private 3/2 as well. This home includes a versatile 2-bedroom, 1-bath in-law suite with its own private entrance, perfect for extended family, guests, or rental potential. Enjoy extra living space in the spacious Florida room, ideal for entertaining, relaxing, or creating the perfect indoor-outdoor flow. With its thoughtful upgrades and multi-generational layout, this home blends functionality with timeless design — truly move-in ready and waiting for you to make it your own!
Listing is courtesy of: EXP REALTY LLC (407-846-0940)
Listing Agent: Laura Mcadams (954-268-5421)
$630,000178 Days on yellowkey MLS ID: S5137596
Bed: 5 Bath: 3.0 Liv Area Sq Ft: 2472 Built: 1957 Tax: $6,425 (2024)Community: Glencoe SubSingle Family
Remarks: SELLER MOTIVATED!! Potential of an extra one percent for closing costs, just ask your agent!! Come view this NEXTGEN Home FULLY MODERNIZED 5-bedroom, 3-bathroom home offering flexibility, and comfort that Includes an Attached 2 Bed/1 Bath IN- LAW SUITE!! Step inside to an open and airy layout featuring Luxury plank flooring, fresh neutral paint, and large windows that fill the home with natural light. The upgraded kitchen is a true showstopper — boasting shaker cabinets, quartz countertops, subway tile backsplash, and stainless steel appliances with stylish hardware accents. Located just a 10 minute walk to Lake Killarney and a 3 minute walk to Killarney Elementary School! What is even more fantastic is the distance to I-4 is literally just 2 minutes away for fast and convenient travel to and from downtown Orlando and just 10 minutes from Park Avenue Winter Park!! So many restaurants, parks, local shops and family activities, Especially during the holidays!! Come see this home with potential income and your own private 3/2 as well. This home includes a versatile 2-bedroom, 1-bath in-law suite with its own private entrance, perfect for extended family, guests, or rental potential. Enjoy extra living space in the spacious Florida room, ideal for entertaining, relaxing, or creating the perfect indoor-outdoor flow. With its thoughtful upgrades and multi-generational layout, this home blends functionality with timeless design — truly move-in ready and waiting for you to make it your own!
207 E KINGS WAY, WINTER PARK, FL 32789
$3,650,000219 Days on yellowkey MLS ID: O6337304
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3719 Built: 2026 Tax: $2,975 (2024)Community: CharmontSingle Family
Taxes:$2,975
Elementary School: Audubon Park K8
Middle School: Audubon Park K-8
Remarks: Under Construction. Step into a world where the timeless charm of Old Winter Park meets the pinnacle of modern luxury designed by Winter Park Design and masterfully crafted by renowned builder Vimaro Homes. Nestled on one of Winter Park’s most coveted tree-lined streets, this stately home immediately commands attention with its double-entry driveway, framed by manicured landscaping and a sense of grandeur like no other. Inside, the home unfolds across more than 3,600 square feet of impeccably designed living space, with every room telling a story of quality, craftsmanship, and comfort. Rich herringbone hardwood floors stretch throughout the residence, complemented by bespoke millwork, and soaring ceilings. At the core of the home, the designer chef’s kitchen is a true showpiece, crafted for culinary excellence and effortless entertaining. Outfitted with top-of-the-line stainless steel appliances, custom cabinetry with designer hardware, and striking quartz countertops, the space is as functional as it is beautiful. A large island provides a natural gathering place, while an adjacent walk-in pantry offers seamless storage and prep. The primary suite is a retreat unto itself; a serene oasis tucked away for ultimate privacy. The spa-inspired en-suite bathroom rivals the finest resorts, featuring a soaking tub, walk-in shower with rainfall fixtures, designer lighting, dual vanities with custom cabinetry, and luxurious stone finishes throughout. A large, custom walk-in closet completes this elegant retreat. Beyond the main living areas, this home offers unique and thoughtfully designed spaces that elevate everyday living including a dedicated home office, a spacious loft, and a grand 3rd floor bonus room. Outdoors, a resort-style pool, covered lanai, and fully equipped summer kitchen create a private haven for year-round entertaining under the Florida sun. For the car enthusiast, this home offers a perfect fusion of elegance and functionality with a stately porte-cochere, a detached garage connected to the home by a breezeway, and an expansive motor court ideal for guest parking or showcasing a prized collection. Every element of this home speaks to impeccable taste and thoughtful design, from the curated finishes and luxury fixtures to the breathtaking architecture and designer lighting. Located just moments from Park Avenue, Rollins College, and Winter Park’s finest shopping and dining, you are truly in the heart of it all. More than a residence, this is a rare architectural masterpiece by Vimaro offering an unmatched lifestyle in the heart of one of Central Florida’s most coveted neighborhoods.
Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)
Listing Agent: Julie Christensen (407-592-2055)
1280 GLADIOLAS DR, WINTER PARK, FL 32792
$489,000119 Days on yellowkey MLS ID: O6370371
1 Days Off yellowkey (back on 4/14/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1624 Built: 1983 Tax: $5,162 (2024)Community: Garden Lake Estates Unit 3Spa: NoSingle Family
Taxes:$5,162
Elementary School: Red Bug Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
Remarks: One or more photo(s) has been virtually staged. Welcome to this beautifully updated 3-bedroom, 2-bath home with a New Roof 2021, screened-in pool, ideally located in the heart of Winter Park. Step inside to a fresh, move-in-ready feel with new flooring throughout, new light fixtures, new windows, and new doors—all thoughtfully selected to give the home a clean, modern look. The open, inviting layout is perfect for everyday living and entertaining, and the screened pool area creates a private Florida retreat for relaxing weekends, family gatherings, or evening swims—without the bugs. Conveniently close to Winter Park’s shopping, dining, parks, and local favorites, this home offers the best of Central Florida living in a prime location. More photos coming soon—don’t miss your chance to see this one!
Listing is courtesy of: FLORIDA PRESTIGIOUS HOMES INC (754-246-2070)
Listing Agent: Ian Trumbach (754-246-2070)
1500 GAY RD #8D, WINTER PARK, FL 32789
$267,00035 Days on yellowkey MLS ID: O6392693
0 Days Off yellowkey (back on 4/14/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1026 Built: 1972Monthly Fee: $425 Tax: $2,630 (2025)Community: Chateaux Du LacCondo
Taxes:$2,630
High School: None
Middle School: None
Remarks: Welcome to the most beautifully updated 2 Bedroom 2 bath End Unit in a Lakefront Community on Lake Killarney. This home features Quartz counter tops with a Granite Island and stainless steel appliances, along with a beverage refrigerator, and luxury vinyl flooring through out the whole unit. A huge living room offers loads of gathering and entertaining space in this cheerful home. Enjoy Florida outdoor living in the private patio. Home is move in ready!! The Community includes a private Boat Ramp and Dock, On-site Boat Parking, Heated Pool and Sauna, and a community grill. Enjoy Sunsets on Lakefront Deck and short walking access to Winter Parks Shops, Restaurants, Movies, Park Avenue, Farmers Market and Downtown Art Festivals. Come see this inviting home and make it yours today!
Listing is courtesy of: SOLID OAK REAL ESTATE LLC (321-888-9232)
Listing Agent: Trevor Laug (321-888-9232)
1618 INDIANA AVE, WINTER PARK, FL 32789
$685,00017 Days on yellowkey MLS ID: O6398673
Bed: 4 Bath: 0.0 Liv Area Sq Ft: 1604 Built: 1963 Tax: $5,477 (2025)Community: LawndaleApartment
Taxes:$5,477
Remarks: Beautiful income-producing duplex located in the highly desirable Winter Park area! This well-maintained property features two units, each offering 2 bedrooms, 1 bathroom, and a dedicated utility room for added convenience. Both sides provide functional layouts with comfortable living spaces, making it ideal for tenants or owner-occupants looking to offset their mortgage. Situated on Indiana Ave, this property is just minutes from Park Avenue, shopping, dining, and major roadways, offering both convenience and strong rental appeal. Whether you're looking to expand your investment portfolio or live in one unit while renting the other, this duplex presents a fantastic opportunity in a prime location.
Listing is courtesy of: NATIONAL REAL ESTATE (407-203-6903)
Listing Agent: Johnathan Lam (954-258-0720)
841 W SWOOPE AVE, WINTER PARK, FL 32789
$499,00091 Days on yellowkey MLS ID: O6373287
REDUCED by $241,000 (32.6%) on 04/13/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1396 Built: 1930 Tax: $3,824 (2024)Community: Capens AddSingle Family
Taxes:$3,824
Remarks: This Winter Park property offers exceptional potential in one of the most desirable and rapidly evolving areas of Central Florida. Zoned R-3, this parcel opens the door to redevelopment possibilities for builders, investors, or end users looking to create something special. Ideally located just minutes from Park Avenue and within walking distance to Winter Park Village, you’ll enjoy easy access to premier dining, shopping, entertainment, and lifestyle amenities. The property is also conveniently situated near Orlando Avenue, providing quick connectivity to surrounding areas. The existing structure is being sold as-is, and the true value lies in the land, zoning, and prime location. With ongoing redevelopment nearby and strong demand for new construction, this is an ideal opportunity to build a custom residence or explore allowable uses under current zoning (buyer to verify all development potential with the City of Winter Park). Whether you’re a builder, investor, or buyer with vision, this is your chance to secure a property in a high-demand corridor with long-term upside.Cash buyers and builders welcome. No HOA. City water and sewer. 32789 zip code.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Evelyn Alicea (407-340-8154)
640 N PARK AVE #5, WINTER PARK, FL 32789
$450,000133 Days on yellowkey MLS ID: O6367841
0 Days Off yellowkey (back on 4/13/2026)
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 673 Built: 1956Monthly Fee: $812 Tax: $4,623 (2024)Community: Park Aire CondoCondo
Taxes:$4,623
Remarks: Under contract-accepting backup offers. Location, Location, Location! Charming first floor 1 bedroom, 1 bath condo ideally located on North Park Avenue in the retro-chic Park Aire complex. Beautifully overhauled in 2018 with quartz counters, new cabinetry, new appliances, custom mosaic kitchen detail, new flooring, new lighting, updated electrical, with picturesque views of the Winter Park Golf Course and Casa Feliz. Enjoy a large walk-in closet, one assigned carport space, and a private storage room. The community offers a sparkling saltwater pool, two third-floor outdoor patios, laundry facility, elevator, and a guest-quarters efficiency available to owners for a nominal fee. Just steps from Park Avenue shopping and dining, cafes, churches, Winter Park Golf Club, Rollins College and more. No pets.
Listing is courtesy of: PARK TOWN REAL ESTATE LLC (561-801-9199)
Listing Agent: David Auerbach (407-619-5250)
1695 LEE RD #E103, WINTER PARK, FL 32789
$139,99034 Days on yellowkey MLS ID: S5146352
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 881 Built: 1966Monthly Fee: $482 Tax: $2,041 (2025)Community: Waterfall CoveCondo
Taxes:$2,041
Elementary School: Hungerford Elem
Remarks: One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Waterfall Cove, where urban convenience meets tranquil living. This charming 2-bedroom, 1-bathroom condo offers a cozy retreat with all the perks of modern living. Located in the heart of Orlando, this condo is perfect for those looking for a blend of city life and natural beauty. As you step into the condo, you're greeted by a bright and spacious living area, perfect for relaxing or entertaining guests. The kitchen features modern new (2025) appliances and ample storage space, making cooking a breeze. The bedrooms are spacious and plenty of natural light, creating a peaceful ambiance. One of the highlights of living at Waterfall Cove is the stunning waterfall feature that gives the community its name. This serene setting is perfect for unwinding after a long day or enjoying a peaceful morning coffee. The community also features a pool and fitness center, providing residents with plenty of opportunities to stay active and healthy. Waterfall Cove is ideally located near Interstate 4, making it easy to commute to major job centers in Orlando. It's also just a short drive away from downtown Orlando and Winter Park, where you can explore a variety of dining, shopping, and entertainment options. Additionally, the condo is close to Rollins College, making it a great option for convenient housing. For those who enjoy the outdoors, Waterfall Cove is close to several parks and nature reserves, where you can hike, bike, or simply enjoy the beauty of the Florida landscape. And if you're a coffee lover, you'll appreciate the proximity to Starbucks, where you can grab your favorite drink on the go. In conclusion, Waterfall Cove offers the perfect blend of comfort, convenience, and natural beauty. With its modern amenities, convenient location, and affordable pricing, it's no wonder why living in this area is so desirable. Don't miss out on the opportunity to make Waterfall Cove your new home! THIS PROPERTY MAY QUALIFY FOR UP TO 40,000.00 IN DOWN PAYMENT ASSISTANCE.
Listing is courtesy of: RE/MAX SELECT GROUP (954-905-2772)
Listing Agent: Jason Price (954-905-2772)
1822 GREENWICH AVE, WINTER PARK, FL 32789
$995,000188 Days on yellowkey MLS ID: A4669605
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1627 Built: 1953 Tax: $2,519 (2024)Community: Golfview HeightsSingle Family
Taxes:$2,519
Remarks: Under contract-accepting backup offers. 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.
Listing is courtesy of: FLATFEE.COM (954-965-3990)
Listing Agent: Cliff Glansen
106 S INTERLACHEN AVE #118, WINTER PARK, FL 32789
$1,395,00083 Days on yellowkey MLS ID: O6380506
REDUCED by $55,000 (3.8%) on 04/13/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1834 Built: 1971 Tax: $9,767 (2025)Community: Cloisters CondoCondo
Taxes:$9,767
Remarks: Experience lakefront living in the heart of Winter Park. One of only two residences in The Cloisters with soaring 9-foot ceilings, this first-floor, three-bedroom, two-bath home offers a rare blend of privacy, scale and panoramic Lake Osceola views. Just two blocks from Park Avenue and adjacent to the Alfond Inn, this condominium lives like a private residence with unmatched access to boutique shopping, fine dining and cultural landmarks. Designed for elegant everyday living and entertaining, the open floor plan showcases a chef’s kitchen with granite countertops, solid wood cabinetry, and an island for prep and serving. The spacious dining and living areas are enhanced by hardwood flooring, crown molding and a marble-trimmed wood-burning fireplace. More than 20 feet of sliding glass doors open to an expansive, L-shaped terrace that brings in natural light and offers breathtaking lake vistas. The oversized primary suite offers serene lake views and includes an en-suite bath with dual vanities, built-in closets and a walk-in shower. Additional features include a rare laundry and utility room with a full-size washer, dryer and sink, updated electrical and plumbing, and upgraded water heater and HVAC system. Just two blocks from Park Avenue, this residence places you in the heart of downtown Winter Park’s sought-after lifestyle. Enjoy effortless access to fine dining, boutique shopping, world-class museums, Rollins College and year-round cultural events, all in an accessible, lakefront setting. Whether going to the Saturday farmers market, dining alfresco along the avenue or taking in the scenic views of Lake Osceola from your private residence, this property offers a seamless blend of luxury and urban elegance.
Listing Agent: Drew Henner (407-406-0662)
1636 ELIZABETHS WALK, WINTER PARK, FL 32789
$2,195,00027 Days on yellowkey MLS ID: O6395638
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3412 Built: 2016Monthly Fee: $268 Tax: $25,133 (2025)Community: Windsong Elizabeths Walk 43/81Spa: YesSingle Family
Taxes:$25,133
Remarks: Discover refined living in this stunning custom-built home located in the coveted community of Windsong. Thoughtfully designed and expertly constructed by Goehring & Morgan, this four-bedroom, 4.5 bath residence offers a perfect balance of elegance, comfort and functionality. From the moment you enter, the home impresses with its airy, open-concept design, ideal for both relaxed living and effortless entertaining. The kitchen serves as a focal point, appointed with leathered granite countertops, a generous center island with seating and a seamless connection to the inviting family room, where a gas fireplace adds warmth and charm. Walls of sliding glass doors extend the living space outdoors to a beautifully designed lanai, complete with a gas-heated pool and a fully equipped summer kitchen featuring a grill, sink, beverage refrigerator and additional seating area. The main level also includes a well-appointed guest suite with a private bath, offering comfort and privacy for visitors, along with a dedicated office or study space. Upstairs, a spacious bonus room provides flexibility for a media room, playroom or lounge, while two additional bedrooms accompany the expansive primary suite. The primary retreat is designed for relaxation, showcasing dual walk-in closets and a luxurious bath with a freestanding soaking tub, oversized shower and separate vanities. High-end finishes are showcased throughout, including travertine flooring across the main living areas and rich wood floors that continue through the bedrooms, staircase, upper hallway and bonus room. As a resident of Windsong, you’ll enjoy access to exceptional community amenities, including resort-style pools, a splash pad, playground and access to the scenic Winter Park Chain of Lakes, creating a lifestyle that is both vibrant and serene in one of Central Florida’s most desirable settings.
3711 VINSETTA CT, WINTER PARK, FL 32792
$1,350,00097 Days on yellowkey MLS ID: O6376139
5 Days Off yellowkey (back on 4/13/2026)
Bed: 6 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4214 Built: 2015Monthly Fee: $178 Tax: $7,488 (2025)Community: Lakeside EstatesSingle Family
Taxes:$7,488
Remarks: Under contract-accepting backup offers. Elevate your lifestyle in the prestigious Lakeside Estates, a private gated Winter Park community anchored by Garden Lake. In a quiet cul-de-sac, on a wrapping corner lot on over 1/3 of an acre and only a short distance to the playground making it easy. A six-bedroom, four-bath home sprawls over 4,200 square feet with back of the house opening to a covered porch with a generously sized saltwater pool, framed in by a podocarpus hedge for privacy, creating a backdrop for entertaining. An additional green space behind hedge for plenty of room to grow. This home has all functions you need with a formal dining and living spaces alongside a spacious family room that is open to kitchen and overlooks backyard. The island takes center stage with a waterfall edge feature and bar seating, custom 42-inch cabinetry, stainless appliances, a cozy eat-in kitchen nook with loads of workspace and closet pantry for ease of storage. A fantastic first-floor guest suite or flex space makes working from home easy. Go upstairs to where all the fun happens. A super large bonus room has additional home theatre rooms accessed through stylish barn doors and it is all snuggled in, everyone will want to stay. Primary suite enjoys a large walk-in closet and a spa bath retreat with soaking tub, walk-in shower and dual vanities. Other features of the home include wood floors throughout, custom window treatments, custom pool with paver decking and a summer kitchen with an abundance of privacy, professionally landscaped, three-car tandem garage with brick drive, long-lasting barrel tile roof, designer light fixtures and more. Lakeside Estates offers exclusive access to a community pier, playground and a boat dock for non-motor kayaks, fishing, canoes, paddleboards and more. In the highly rated Seminole County School district as well as minutes from Trinity Prep, Geneva School, Christian Circle and more. Enjoy world-class restaurants, shopping and beautiful parks and trails, close to major roadways, UCF, Valencia and downtown Orlando. A pristine location, coupled with a unique Winter Park community, is a rare find. Homes do not come along in this neighborhood often, making it a special opportunity for the discerning buyer.
Listing Agent: Alison Mosley (407-304-6458)
543 E LAKE SUE AVE, WINTER PARK, FL 32789
$1,875,00021 Days on yellowkey MLS ID: O6397480
1 Days Off yellowkey (back on 4/13/2026)
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3657 Built: 1986 Tax: $14,126 (2025)Community: Lake Virginia Pt RepSpa: NoSingle Family
Taxes:$14,126
Remarks: Under contract-accepting backup offers. Welcome to Timberlane Shores—one of Winter Park’s most desirable neighborhoods! This beautiful 4-bedroom, 4.5-bath home sits on over a third of an acre in a quiet, tucked-away location with gorgeous updated landscaping. Inside, you’ll find wide-plank hardwood floors throughout and a thoughtfully designed floor plan with separate living and dining rooms plus a spacious family room. The bright kitchen features white cabinetry with pull-out drawers, marble countertops, subway tile backsplash, and newer appliances (2018), including a Sub-Zero refrigerator and Wolf gas 4 burner range. The kitchen opens to a bright sunroom with beautiful wood-like tile floors laid in a herringbone pattern (2018). Such a great space that is filled with natural light—perfect as a casual gathering space or playroom, making this an ideal home for entertaining. The sunroom overlooks the enormous backyard space and large pool area with custom designed pavers (2023). A downstairs guest suite with full bath provides comfort and privacy, while a dedicated office with built-in desks and brand new carpet adds functionality. Upstairs, the oversized primary suite boasts a beautifully appointed bathroom with dual sinks, marble countertops, soaking tub, and separate walk-in shower, along with a custom walk-in closet. Two additional upstairs bedrooms each offer en-suite baths, including one renovated in 2021. Recent updates include new windows (2017), solid wood front door (2021), renovated bath (2021), two new AC units and duct cleaning (2024), and a new roof (2024). This exceptional home offers the perfect blend of style, comfort, and location—truly a must-see.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Lisa Fleming (321-228-8341)
2919 BOWER RD, WINTER PARK, FL 32792
$779,00042 Days on yellowkey MLS ID: O6391025
3 Days Off yellowkey (back on 4/13/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2325 Built: 1971 Tax: $9,857 (2025)Community: Winter Park PinesSingle Family
Taxes:$9,857
Remarks: Beautifully updated 3BR/2BA pool home in the highly sought-after Winter Pines community of Winter Park! This move-in ready home offers a bright, open layout with multiple living spaces, perfect for both everyday living and entertaining. The upgraded kitchen features stainless steel appliances, granite countertops, breakfast bar, custom cabinetry, and a farmhouse-style undermount sink, all opening to a spacious dining area with a stunning exposed brick fireplace. A newly enclosed and fully air-conditioned back room (converted from the former porch) offers exceptional flex space—perfect for a bonus room, playroom, or additional living area. Designed to maximize Florida living, this space features an expansive sliding glass door that seamlessly blends indoor and outdoor living, while a separate dedicated HVAC system ensures optimal comfort year-round. The primary suite includes a walk-in closet, dressing area, and en suite bath with dual-sink granite vanity and step-in shower. Just off the primary bedroom is a newly added office/nursery space, perfect for working from home or a private retreat. Split floor plan with two additional generously sized bedrooms and a full bath for added privacy. Enjoy Florida living outdoors with a spacious patio, sparkling pool, and large backyard featuring brand-new sod—perfect for entertaining or relaxing. Additional upgrades include fresh paint and a high-end seamless metal roof. Prime location just minutes to Cady Way Park, shopping, dining, and zoned for top-rated schools. Don’t miss this one—schedule your showing today!
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Nick Mckee (407-913-0171)
850 JUANITA RAEL, WINTER PARK, FL 32789
$1,425,000113 Days on yellowkey MLS ID: O6370568
1 Days Off yellowkey (back on 1/12/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2306 Built: 1966 Tax: $6,218 (2024)Community: Green Oaks Rep 03Spa: NoSingle Family
Taxes:$6,218
Remarks: Under contract-accepting backup offers. Location, location, location. Sought after location on the North end of Park Avenue. Avoid the traffic in and out of Downtown Winter Park while being minutes away from everything on the Avenue. One of the very few single level homes of this quality in Winter Park 32789. Single story ranch on a lovely, private, large corner lot. 2306 heated and cooled square feet. Primary bedroom en-suite with 3 additional bedrooms and 2 additional bathrooms, 15,000 sq ft large corner lot with oversized side-entry garage and over-sized laundry room. Magnificent, private back yard oasis with pool and covered veranda. Freshly painted inside and outside. New lovely oak wood floors, newer roof and windows, new hardware and updated lighting. Oversized two car garage with storage. This home is move-in ready and all the model-home furniture is available to purchase as well.
Listing is courtesy of: PHIL KEAN REAL ESTATE LLC (407-982-2265)
Listing Agent: Brad Grosberg (321-439-1494)
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