Location: Winter Park
Keyword(s): Winter Park High
Keyword(s) High School: Winter Park High
Do Not Show Listings
311 E MORSE BLVD #1-3, WINTER PARK, FL 32789
$1,895,00084 Days on yellowkey MLS ID: O6406368
REDUCED by $30,000 (1.6%) on 07/13/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2304 Built: 1960Monthly Fee: $2,471 Tax: $16,493 (2025)Community: Whispering Waters/Phillips Circle RepCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$16,493
Elementary School: None
High School: Winter Park High
Tax Year: 2025
Middle School: Audubon Park K-8
Remarks: Enjoy the Winter Park lifestyle in this beautifully renovated 2-bedroom, 2-bath lakefront condo offering 2,304 square feet in the heart of downtown Winter Park. Located on the second floor of Building 1, this light-filled residence was extensively remodeled in 2023 with an open floor plan and raised ceiling heights that give the home an airy, comfortable feel throughout. The spacious living room and kitchen take full advantage of the breathtaking views of Lake Osceola, while two fireplaces—one in the living room and another in the primary bedroom—add warmth and character to the space. The kitchen has been updated with white cabinetry, stainless steel appliances, double ovens, induction cooktop, tile backsplash, center island, and wine/beverage refrigerator. Formal living and dining spaces offer plenty of room for entertaining, and the oversized entertainment room off the primary bedroom features a closet and separate entry, making it a great option for a third bedroom, media room, or home office. The primary suite offers a walk-in closet and en-suite bathroom with a shower and dual sinks. The secondary bedroom includes two closets along with a separate alcove ideal for a reading nook or office space. A Florida room, currently used as a storage room, features brick flooring. Other highlights include plantation shutters throughout, beautiful exposed beams, additional storage closet in the garage, and two designated parking spaces in the covered garage. Residents enjoy a community pool, gated underground parking with elevator access, and an unbeatable location just steps from Park Avenue’s shops, restaurants, museums, and seasonal events. A rare opportunity to enjoy spacious lakefront living in one of Winter Park’s most desirable communities.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Megan Cross (407-353-9997)
1581 FOREST AVE, WINTER PARK, FL 32789
$3,275,000141 Days on yellowkey MLS ID: O6382377
REDUCED by $118,000 (3.5%) on 07/20/2026
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4683 Built: 1954 Tax: $20,042 (2024)Community: Ellno WilloSpa: NoSingle Family
Taxes:$20,042
Elementary School: Audubon Park K8
Tax Year: 2024
Remarks: This exceptional Winter Park residence offers a floor plan rarely found in the area, with nearly all living spaces thoughtfully positioned on a single level for effortless everyday living. Completely rebuilt in 2018 by renowned custom builder Posada Homes, a member of the elite Master Custom Builders Council, the home blends modern design, crisp architectural lines, and timeless elegance across an expansive 0.39-acre lot along one of Winter Park’s most picturesque tree-lined streets. The home immediately captivates with its refined architecture and beautifully manicured grounds. Inside, sunlight streams through expansive windows, illuminating hardwood flooring, intricate millwork, and thoughtfully curated finishes that reflect the craftsmanship of a true custom build. Just off the foyer, a hidden wine room provides a sophisticated surprise, perfect for those who love to entertain. At the center of the home is the chef’s kitchen designed for both beauty and functionality. Outfitted with premium Thermador appliances, sleek quartz countertops, a generous center island, and custom cabinetry, the kitchen flows effortlessly into the expansive great room where high ceilings, designer lighting, and elegant architectural details create an atmosphere that is both inviting and refined. Tucked away for privacy, the primary suite is positioned just off a luxurious family room featuring custom built-ins and a gas fireplace. The primary suite itself is a true sanctuary, complete with a sitting area, private coffee bar, and a spa-inspired bath featuring dual vanities, a soaking tub, and an oversized walk-in shower. Rarely found in Winter Park, all bedrooms are conveniently located on one level, including two primary suites, allowing the home to deliver seamless livability without sacrificing architectural interest or sophistication. Upstairs, a private office, half bath, and bonus room provide the perfect space for work, media, recreation, or relaxation. Outdoors, the home transforms into a private resort-style retreat. A covered lanai overlooks the sparkling pool and expansive grounds, creating the ideal setting for entertaining or quiet evenings at home. Adding even more flexibility, a 252-square-foot detached studio currently functions as a gym but could easily become a summer kitchen cabana, guest retreat, or art studio. Located within walking distance of Park Avenue’s boutiques, restaurants, and cafés, and just moments from Rollins College and the Winter Park Chain of Lakes, this residence embodies luxury living at its finest. Don’t miss this rare opportunity to own one of Winter Park’s most outstanding homes. The current flooring offers a rich look, and for those who prefer a lighter palette, the seller is open to providing a credit toward flooring updates and coordinating the installation of new flooring if desired.
Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)
Listing Agent: Julie Christensen (407-592-2055)
1836 GRINNELL TER, WINTER PARK, FL 32789
$999,000175 Days on yellowkey MLS ID: O6380457
4 Days Off yellowkey (back on 7/6/2026)
REDUCED by $51,000 (4.9%) on 05/06/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1907 Built: 1995 Tax: $11,979 (2025)Community: Lake VirginiaSingle Family
Taxes:$11,979
Elementary School: Brookshire Elem
Middle School: Glenridge Middle
Remarks: Under contract-accepting backup offers. Virtually Staged. Beautifully renovated home in the heart of highly desirable Winter Park, surrounded by multi-million-dollar properties. Move-in ready and thoughtfully updated throughout. Set on an expansive lot approximately 79 x 152 (11,305 square feet) provides plenty of space to build your future dream home! This light-filled home features wide-plank flooring, recessed lighting, and all new modern fixtures. The entryway features comfortable seating, built in cabinets with an electric fireplace and wine refrigerator. The sleek, updated kitchen offers a gas range, stylish finishes and a functional layout perfect for everyday living and entertaining. Retreat to the spacious primary bedroom with a fabulous ensuite bath, complete with a soaking tub, dual vanities, a large separate shower, and a generous walk-in closet. A split-bedroom floor plan provides added privacy and comfort. The fully fenced backyard offers plenty of room for a pool and includes private parking for a boat on the side of the home. Whether you enjoy the home as it is or choose to build your dream residence, the possibilities are endless. New roof installed in 2022.
Listing Agent: Cindy Kuykendall (407-718-3235)
3006 NORTHWOOD BLVD, WINTER PARK, FL 32789
$1,189,00035 Days on yellowkey MLS ID: O6419056
REDUCED by $10,000 (0.8%) on 07/23/2026
Bed: 4 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2075 Built: 1953 Tax: $4,188 (2025)Community: Northwood TerraceSpa: NoSingle Family
Taxes:$4,188
Remarks: Reimagined from the ground up for modern living while honoring its original mid-century modern heritage, this 1953 Winter Park residence pairs authentic MCM character with the ease of all-new finishes and systems. Four bedrooms and three full bathrooms are arranged around an open living, dining, and kitchen core that opens to a light-filled sitting area. White oak floors run throughout, while designer lighting and ceiling fans, clean horizontal lines, and warm natural finishes carry the home's MCM soul. The kitchen anchors the home with Taj Mahal quartzite counters and brand new KitchenAid stainless steel appliances. Step out to an expanded rear patio overlooking a private fenced backyard, ideal for entertaining or quiet evenings at home. Move in with confidence: new roof, all-new windows, new 200-amp electrical service, all-new plumbing with new water heater, new HVAC ductwork, and a new Nest thermostat. The attached garage and dedicated interior laundry complete the layout. The location is the rare kind you can live on foot: walk to East End Market, Kelly's Homemade Ice Cream, Redlight Redlight, Sushi Lola's, and the sought-after Audubon Park K-8 School. Winter Park High and the shops and dining of Park Avenue are just minutes away. A thoughtfully rebuilt classic in one of the area's most established and connected neighborhoods.
Listing is courtesy of: ORLANDO HOMES GROUP LLC (407-923-6524)
Listing Agent: Daren Ellington (407-923-6524)
1000 S SEMORAN BLVD #305, WINTER PARK, FL 32792
$129,0007 Days on yellowkey MLS ID: O6428044
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 735 Built: 1969Monthly Fee: $355 Tax: $1,377 (2025)Community: Golfside Villas CondoCondo
Taxes:$1,377
Remarks: Freshly Updated 1-Bedroom Condo – Perfect for Homeowners or Investors! Whether you're looking for your first home, downsizing, or adding to your investment portfolio, this move-in-ready 1-bedroom, 1-bath condominium is an excellent opportunity. Featuring brand-new luxury vinyl plank flooring and a freshly painted interior, this home offers a clean, modern feel throughout. The open-concept floor plan seamlessly connects the kitchen, dining, and living areas, creating a bright and inviting space for everyday living and entertaining. A set of French doors leads to the screened-in porch, providing the perfect spot to enjoy your morning coffee or unwind after a long day. The spacious bedroom features a large walk-in closet, offering plenty of storage. This condo also includes one assigned parking space, along with additional guest parking for visitors. Residents enjoy access to a community pool and onsite laundry facilities, adding to the convenience of low-maintenance living. Ideally located just minutes from SR 408, the University of Central Florida (UCF), shopping, dining, restaurants, and entertainment, this condo offers an unbeatable combination of comfort, convenience, and value. Whether you're searching for a primary residence or a smart investment opportunity in a high-demand area, this Central Florida gem is one you won't want to miss!
Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)
Listing Agent: Melissa Vance (407-489-5166)
777 HALIFAX AVE, WINTER PARK, FL 32792
$1,500,00021 Days on yellowkey MLS ID: O6422901
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3109 Built: 2021 Tax: $16,519 (2025)Community: Park Manor First AddSpa: NoSingle Family
Taxes:$16,519
Elementary School: Lakemont Elem
Middle School: Maitland Middle
Remarks: Virtually Staged. Built in 2021 by David Weekley Homes, this thoughtfully designed 5-bedroom, 4.5-bath residence delivers 3,109 square feet of refined, light-filled living in one of Central Florida's most desirable locations. The sought-after Easterley floorplan opens into a bright, open-concept layout where soaring ceilings and abundant natural light set an effortlessly elegant tone, with generous room to gather, work, and unwind. At the heart of the home, a gourmet kitchen anchors the space with quartz countertops, a gas range, premium GE appliances, and a walk-in pantry—equally suited to weeknight dinners and lively entertaining. The first-floor primary suite offers a private retreat with a spa-inspired bath featuring a walk-in shower and a separate soaking tub, while four additional bedrooms provide flexible space for guests, a home office, or a playroom. Already plumbed and wired for a pool, the backyard is primed to become your own private oasis—simply add the design you've always envisioned. The location is exceptional. The home is zoned for top-rated schools, is just a short walk to the Winter Park YMCA, moments from Interlachen Country Club, and less than a mile from AdventHealth Winter Park—an unbeatable commute for those in the medical field. Park Avenue's upscale shopping and dining is just two miles away, with Baldwin Park's shops, restaurants, and lakeside trails only three miles from your door. Best of all: NO HOA. Modern construction, an unmatched address, and true Winter Park living—all in one.
Listing is courtesy of: SAFFORD REAL ESTATE LLC (407-461-3172)
Listing Agent: Jared Smith (229-406-0372)
2010 SUMMERFIELD RD, WINTER PARK, FL 32792
$575,00021 Days on yellowkey MLS ID: O6420140
REDUCED by $19,500 (3.3%) on 07/24/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1889 Built: 1957 Tax: $7,917 (2025)Community: Kenilworth Shores Sec 07Single Family
Taxes:$7,917
Remarks: Welcome to this beautifully maintained and thoughtfully updated home in the desirable City of Winter Park, offering an exceptional blend of comfort, space, and convenience. From the moment you arrive, the freshly installed, vibrant green front lawn and attractive landscaping create an inviting first impression. Inside, the cathedral ceiling enhances the spacious feel of the open floor plan, complemented by luxury vinyl flooring and ceramic tile throughout. The well-appointed kitchen features white cabinetry, granite countertops, and a new stainless steel appliance package that adds a modern touch. The home's versatile layout offers plenty of room for everyday living and entertaining, including a separate family room, a bright Florida Room, and a dedicated office or exercise room equipped with an energy-efficient mini-split system and convenient access to the carport. The inside utility room includes a full-size washer and dryer, as well as a second side-by-side refrigerator for added storage and convenience. The spacious primary bedroom provides a comfortable retreat with a private bath featuring maple cabinetry, ample vanity storage, and a roomy walk-in shower. The guest bath offers a tub/shower combination. Step outside to enjoy the spacious, fully fenced backyard—perfect for relaxing, entertaining, gardening, or enjoying the Florida sunshine. Additional features include a storage shed, sprinkler system supplied by a separate well, and a one-car carport with parking for up to three additional vehicles. Major updates include an AC system replaced in 2017, a new roof and electrical panel in 2019, and replumbing completed in 2019. Best of all, you are walking distance to Winter Park High School and just minutes from local dining, shopping, and everyday conveniences. With its spacious floor plan, flexible living areas, attractive updates, generous outdoor space, and prime Winter Park location, this home is a must-see. Schedule your private showing today! Buyer/buyer's agent to verify all schools and room measurements. Appliances convey as is. Brio Management LLC, Seller, is owned by 2 Florida Licensed Real Estate Brokers.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Barry Sanford Pa (407-694-5598)
1871 BARKER DR, WINTER PARK, FL 32789
$779,00015 Days on yellowkey MLS ID: O6425831
0 Days Off yellowkey (back on 7/24/2026)
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2231 Built: 1957 Tax: $8,858 (2025)Community: South Lakemont ShoresSpa: NoSingle Family
Taxes:$8,858
Elementary School: Baldwin Park Elementary
Remarks: Under contract-accepting backup offers. Rare Winter Park gem, nestled between Lake Baldwin and the heart of Winter Park. This fully refreshed, single-story home features brand-new interior and exterior paint, complemented by newly refreshed landscaping. Offering 3 bedrooms and 3 full bathrooms, the highly desirable split floor plan includes two primary suites. The main primary suite boasts an updated shower, vanity, and a spacious walk-in closet. The second suite features a garden tub with shower and its own walk-in closet. The updated kitchen is equipped with floor-to-ceiling cabinets for ample storage and a custom built-in kitchen nook with bench seating. Additional highlights include a cozy fireplace, laminate flooring, plantation shutters, an air-conditioned laundry room, and an incredible oversized 3-car garage. Enjoy Florida’s outdoor living year-round with a screened porch and a spacious, fully fenced backyard. Superb location under a half-mile to Baldwin Park, 2.5 miles to Park Avenue, and 3 miles to Rollins College. Zoned for highly rated Winter Park schools and situated just moments from the Lake Baldwin dog park.
Listing Agent: Rikhil Amin (407-792-8069)
616 BRECHIN DR, WINTER PARK, FL 32792
$999,00070 Days on yellowkey MLS ID: O6409911
REDUCED by $46,000 (4.4%) on 07/24/2026
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2638 Built: 1961 Tax: $4,251 (2025)Community: Kenilworth Shores Sec 04Single Family
Taxes:$4,251
Remarks: Welcome to your fully reimagined Florida home. Among tree-canopied streets in the desired Kenilworth Shores neighborhood, this mid-century modern ranch home was completely transformed in 2005. The redesign added substantial square footage and created a completely unique, functional floor plan that separates it from any other home in the area. Spanning 2,638 square feet of seamless indoor-outdoor living, the property features four bedrooms, 4.5 baths, including three complete en-suite setups that offer maximum privacy for family or guests, plus a dedicated 130-square-foot office. Key property features include elegant design. Step onto gorgeous, rich Brazilian cherry wood flooring that flows beautifully through the open living spaces. Work from home where a dedicated, quiet office space provides an environment for remote work, study or creative projects. Spacious kitchen allows you to enjoy an open-concept floor plan, an eating space in the kitchen, solid wood cabinetry, Silestone countertops and coordinating GE Profile appliances, including a convection oven microwave, giving the kitchen dual oven capacity. Indoor laundry room is a convenient, separate indoor laundry room that keeps household chores organized, quiet and out of sight. Private saltwater oasis allows you to relax in your fully fenced, private backyard featuring an in-ground saltwater pool with spa jets and solar heat. Turnkey infrastructure where peace of mind comes built-in with a new roof (2022), fresh exterior paint and trim (2022), and an updated 200-amp electrical panel. Smart home and systems, equipped with an app-controlled smart security system covering all doors and windows, an EcoBee thermostat and energy-efficient LED recessed lighting. Location and lifestyle benefits include top-tier education, zoned for premier Orange County schools, including Brookshire Elementary, Glenridge Middle School and Winter Park High School (home to a globally recognized International Baccalaureate program). Active recreation to Cady Way Park to enjoy the community pool, playground, sports fields and extensive bike trails. Unbeatable convenience just minutes away from Winter Park Pines Golf Course, two Publix grocery stores, and the upscale dining, boutique shopping, and museums of Park Avenue and Baldwin Park Town Center. This exceptional property blends classic Winter Park lifestyle with the modern infrastructure you demand.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Alison Mosley (407-304-6458)
200 SAINT ANDREWS BLVD #2904, WINTER PARK, FL 32792
$230,0008 Days on yellowkey MLS ID: O6427536
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 1219 Built: 1970Monthly Fee: $430 Tax: $3,519 (2025)Community: Four Seasons CondoCondo
Taxes:$3,519
Remarks: WHAT A GEM! Tucked away in a private, sought after community and so conveniently located in breathtaking Winter Park. Here’s a beautifully maintained, upgraded and move-in ready home. With 2 large bedrooms and 1.5 bathrooms, this unit spans 1,219 square feet, providing an ideal space for cozy living. Enjoy the benefits of a peaceful and friendly community, with well-manicured grounds and a welcoming atmosphere. This charming home has been tastefully updated with upgraded laminate flooring, a renovated kitchen with granite countertops, newer cabinets and a stylish backsplash. The floor plan offers a dining & family room open combination which looks out on the porch and brings in plenty of natural light. Both nicely sized bedroom suites are on the second floor and have a shared & updated bathroom. Ample storage on the back patio for your bike and all your extra toys allowing you to enjoy your weekends. This is an extremely well managed community with an onsite manager taking pride in the community and care for their residents. Four Seasons community provides super amenities including a cubhouse with library, a renovated fitness center, 3 swimming pools, tennis courts, a laundry facility steps away and shuffleboard. Walk to Cady Way Park with tennis courts, baseball and soccer fields, playgrounds, community pool and Cady Way Trail. Minutes to Advent Health Winter Park Hospital, shopping on Park Avenue, Rollins College, Valencia, Full Sail and UCF. This pet friendly community and charming condo has everything you need! Great opportunity to own in FOUR SEASONS condominiums where LOCATION, LOCATION, LOCATION is prime!
Listing Agent: Sharon Mikol (407-963-3679)
1130 PARK NORTH PLACE, WINTER PARK, FL 32789
$2,200,000127 Days on yellowkey MLS ID: O6392394
REDUCED by $295,000 (11.8%) on 06/29/2026
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 4011 Built: 1968 Tax: $9,744 (2025)Community: Park NorthSingle Family
Taxes:$9,744
Remarks: Under contract-accepting backup offers. WALK TO PARK AVENUE from this RARE nearly HALF ACRE homesite with OVER 4,000 SQUARE FEET and 5 BEDROOMS in one of Winter Park's most desirable locations. Leave your car at home and enjoy Park Avenue's renowned restaurants, boutiques, cafés, parks, and the Winter Park Golf Course just moments from your front door. Tucked away on a quiet cul-de-sac, this timeless two story residence offers the perfect combination of space, warmth, and an exceptional floor plan designed for both everyday living and effortless entertaining. From the moment you step inside, the home feels welcoming with expansive living spaces, soaring ceilings, and abundant natural light. The main level is anchored by a spacious primary suite, while the family room features dramatic ceilings and opens seamlessly to the kitchen and casual dining area, creating the true heart of the home. French doors lead to a screened patio with a charming Southern feel that overlooks the expansive backyard, offering endless possibilities for a pool, outdoor entertaining, or future expansion. A separate formal living room provides additional flexibility, while the formal dining room connects to a butler's pantry, making hosting gatherings both functional and elegant. Upstairs, you'll find four generously sized bedrooms with beautiful original hardwood floors, providing ample space for family, guests, home offices, or a playroom. LOCATION. LOT SIZE. WALKABILITY. Opportunities to own a nearly half acre property this close to Park Avenue are exceptionally rare. Enjoy the very best of Winter Park with premier shopping, award winning dining, parks, golf, and everything that makes this one of Central Florida's most coveted addresses just a short stroll away.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Jennifer King (407-595-3272)
708 BALMORAL RD, WINTER PARK, FL 32789
$1,690,00022 Days on yellowkey MLS ID: O6423883
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2786 Built: 1960 Tax: $6,459 (2025)Community: Kenilworth Shores Sec 06Spa: NoSingle Family
Taxes:$6,459
Remarks: A rare elevated corner lot in the heart of Winter Park — walkable to Park Avenue's boutique shops and restaurants, and set on one of the area's most desirable streets. Substantial homesite, prime location, endless potential. Coming soon. Reach out to the listing agent if you would like more information about the property.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Caitlin De Oliveira (407-267-7196)
2708 LION HEART RD, WINTER PARK, FL 32792
$614,500149 Days on yellowkey MLS ID: O6387685
REDUCED by $500 (0.1%) on 07/23/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1785 Built: 1963 Tax: $7,007 (2024)Community: Winter Park Pines RepSpa: NoSingle Family
Taxes:$7,007
Remarks: Welcome to 2708 Lion Heart Rd, where timeless charm meets modern elegance in the heart of Winter Park. This beautifully reimagined home has been thoughtfully renovated from top to bottom, offering a seamless blend of style, comfort, and functionality. Step inside to discover brand-new luxury vinyl plank flooring flowing throughout, creating a warm and cohesive feel in every room. The stunning two-tone kitchen is a true centerpiece, featuring sleek quartz countertops, contemporary finishes, and new appliances to be installed at closing—perfect for both everyday living and entertaining. The upgrades continue in the fully renovated bathrooms, where carefully selected color palettes and high-quality finishes provide a fresh, sophisticated look designed to stand the test of time. Every detail of this home has been meticulously considered, leaving no space untouched. Outdoors, enjoy your private oasis with a newly resurfaced pool—ideal for relaxing weekends or hosting gatherings year-round in Florida’s sunshine. This move-in-ready gem offers the perfect opportunity to own a like-new home in a highly desirable location. Come experience the beauty, quality, and lifestyle that 2708 Lion Heart Rd has to offer—your dream home awaits.
Listing is courtesy of: EQUITYPRO LLC (407-203-6860)
Listing Agent: Navid Rokh (321-900-5977)
1037 N VIRGINIA AVE, WINTER PARK, FL 32789
$649,00036 Days on yellowkey MLS ID: O6419694
0 Days Off yellowkey (back on 7/23/2026)
Bed: 3 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 1101 Built: 1960 Tax: $7,186 (2024)Community: Tantum AddSpa: NoSingle Family
Taxes:$7,186
Remarks: Under contract-accepting backup offers. THE best kept secret in WP! Newly renovated charming bungalow located directly on famed 4th Fairway on WP9 – Winter Park Golf Course! Quiet, private & secluded setting with gorgeous views on dead end street. Walk or bike to Park Avenue, dining and shopping, Rollins College and Winter Park Village. New roof and water heater 2023, refinished hardwood floors, new kitchen with stainless appliances, renovated bath, 3 generous bedrooms, bonus Florida Room, PLUS single car garage. Open patio in backyard with separate firepit seating area overlooking the golf course. Great rental and/or build your dream home! Don’t miss this “one of a kind – live your best Winter Park life” opportunity!
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Lisa Gould (407-721-7612)
2504 FORFARSHIRE DR, WINTER PARK, FL 32792
$630,00015 Days on yellowkey MLS ID: O6424656
0 Days Off yellowkey (back on 7/22/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1915 Built: 1962 Tax: $2,733 (2025)Community: Brookshire Heights 2Nd AddSingle Family
Taxes:$2,733
Remarks: RARE TWO-OWNER MID-CENTURY MODERN HOME IN WINTER PARK PROPER!! You will fall in love as the canopy of trees along Forfarshire Drive leads you to the door of this desirable Winter Park address. A fresh exterior re-envisioning brings a modern curb appeal, complete with a beautifully tiled covered front porch, glass entry door, Zen fountain and low architectural awnings provide an immediate sense of style and anticipation of what awaits inside the home. Upon entry, a large open living area with over-sized picture window and a stylish dining area, adorned with Brazilian hardwood flooring create a relaxed living experience. Updated kitchen includes white cabinetry (undermount counter lighting), Sile Stone countertops with undermount sink, stainless fridge & dishwasher and brush nickel hardware finishes. A large rear bonus room with storage closet space (designer built-ins) and oversized slider door leads to fenced and private backyard, the perfect retreat to relax and unwind. This wide-shoulder split floorplan offers a left-side primary bedroom with hardwood flooring and a large en suite office with access door to backyard, all wrapped windows with sophisticated Plantation shutters. The right side guest wing includes two large bedrooms flanking a remodeled full guest bathroom. KEY UPDATES INCLUDE: Architectural Shingle Roof (2016), Double Pane Windows (throughout), Knockdown Ceilings, Recessed LED Lighting & Touch Control Switches, PEX Plumbing, Interior Panel Box, Garage Opener. Walking distance from the finest amenities in the area: Cady Way Walking Trail, Ward Park, Winter Park Pines Golf Club and the area’s finest Winter Park School District (Brookshire Elementary, Glenridge Middle, Winter Park High). This home combines prestige and affordability in one irreplaceable address. See it before the opportunity has passed you by!!
Listing is courtesy of: RE/MAX CENTRAL REALTY (407-333-4400)
Listing Agent: Bill Miller (407-415-2263)
1271 PALMER AVE, WINTER PARK, FL 32789
$2,275,00011 Days on yellowkey MLS ID: O6426530
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2835 Built: 1948 Tax: $23,515 (2025)Community: J Kronenberger SubSpa: NoSingle Family
Taxes:$23,515
Remarks: This WINTER PARK POOL HOME is set on a corner lot with entrances from both Palmer Avenue and Temple Drive. Located within Winter Park's exclusive J Kronenberger community, this luxury property is tucked away approximately a half mile to Winter Park's YMCA, Phelps Park & the lovely Kraft Azalea Garden, and approximately 1.5 miles to Park Avenue's restaurants, boutiques and farmer's market. The floor plan offers 4 bedrooms, 4.5 bathrooms & a home office/bonus room. The bedrooms are organized in a triple split plan arrangement that frames the open-concept gathering areas. Three bedrooms have private ensuite bathrooms, the 4th bedroom is placed directly next to the hall bath, and the office/bonus room sits adjacent to the guest half bath...everyone has a bathroom! Multiple exits lead out to the backyard, seamlessly merging the indoor and outdoor spaces. Mature hedges provide natural privacy for the open-air pool, spacious pool deck and backyard lawn. Additionally, a backyard paver path provides access to the property's 2-car detached garage. There is plenty of parking for year-round entertaining with the front half circle drive and the rear 2-car garage with multi-car driveway. This home uses natural gas to fuel the range, tankless water heater and outdoor firepit on the pool deck. Recent updates include outdoor perimeter lighting, rear fence, privacy hedges & irrigation. Prime real estate within Winter Park’s historic tree-lined streets.
Listing is courtesy of: REDFIN CORPORATION (407-708-9747)
Listing Agent: Sheri Malin (407-603-5221)
303 SCOTTSDALE SQ #303, WINTER PARK, FL 32792
$80,00021 Days on yellowkey MLS ID: O6424296
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1020 Built: 1974 Tax: $1,392 (2025)Community: Winter Park Woods CondoCondo
Taxes:$1,392
Remarks: Great location for homeowner or investor. Located close to FullSail and UCF and major roads, shopping, eating and more. Don't hesitate to see this one before it is gone!
Listing Agent: Lisa Wright (321-231-3141)
2824 WOODSIDE AVE, WINTER PARK, FL 32789
$600,00023 Days on yellowkey MLS ID: O6423146
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 912 Built: 1952 Tax: $5,163 (2025)Community: Orangewood ParkSingle Family
Taxes:$5,163
Remarks: Location, location, location. Wonderful home located in Winter Park besides Baldwin Park. Live in this home now - or purchase for the property and build your custom home! The yard is large. Large shed in the yard to store all of your yard essentials. You will love the area and the convenience to what makes this area special...steps from East End Market, lots of amazing restaurants, shopping, Leu Gardens, and so much more. Updates to the home include: Roof: 2020, HVAC 2019, Elecrical - new utility box, Plumbing: re-plumbed Kitchen and both bathrooms. Welcome Home.
Listing is courtesy of: PARKSIDE PROPERTIES, LLC (407-376-6635)
Listing Agent: Kristin Haughwout-Osorio (407-376-6635)
2948 ANTIQUE OAKS CIR #94, WINTER PARK, FL 32792
$150,000327 Days on yellowkey MLS ID: O6342254
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 749 Built: 1984Monthly Fee: $300 Tax: $1,831 (2024)Community: Parkview Village CondoCondo
Taxes:$1,831
Elementary School: Aloma Elem
Remarks: Welcome to this bright and cozy 1-bedroom, 1-bathroom corner unit located in the highly desirable Winter Park area of Orlando. This well-maintained condo features ceramic tile flooring throughout, a spacious walk-in closet in the master bedroom, a laundry closet with washer and dryer included, and modern light fixtures. Enjoy the outdoors on your very nice private balcony, and take advantage of private stairs from the outside entrance—a rare and convenient feature. Located in a beautifully kept community with easy access to shops, restaurants, and all of Winter Park's charm. Ideal as a first home, seasonal getaway, or investment opportunity!
Listing is courtesy of: THE PAMPAS REAL ESTATE GROUP, LLC. (561-234-7771)
Listing Agent: Santiago Silva (561-234-7771)
2715 PRINCE JOHN RD, WINTER PARK, FL 32792
$494,90053 Days on yellowkey MLS ID: O6415084
REDUCED by $4,000 (0.8%) on 07/22/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1565 Built: 1963 Tax: $7,101 (2025)Community: Winter Park Pines RepSingle Family
Taxes:$7,101
Remarks: GREAT HOME & GREAT VALUE — home needs cosmetic work and some TLC - if you DIY you could have instant equity. Thoughtful floor plan with two living spaces and a screened-in porch. Located in desirable Winter Park, 3 blocks from parks, cycling trails, and a public pool, plus minutes from Park Avenue’s shops and restaurants. Enjoy top-rated schools and a lovely, walkable neighborhood. Zoned for BROOKSHIRE ELEMENTARY which is 3 blocks away. New roof (12/2021), New water heater (12/2021), Re-piped (1/2022, no polybutylene), New garage door and opener (2/2022), New AC evaporator coil (6/2022) and New French drain system (6/2023). The home has an irrigation system and irrigation well and New gutters (2/2022). OWNER FINANCING available for owners or flippers. All room dimensions must be independently verified by the buyer.
Listing is courtesy of: VIA PROPERTIES LLC (321-229-6085)
Listing Agent: Donna Peebles (321-229-6085)
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