Location: Winter Park , 32792
Do Not Show Listings
8433 COMMANDER CV, WINTER PARK, FL 32792
$440,00046 Days on yellowkey MLS ID: O6416635
REDUCED by $5,000 (1.1%) on 07/15/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1903 Built: 1986Monthly Fee: $76 Tax: $3,556 (2025)Community: Trinity BaySpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,556
Elementary School: Eastbrook Elementary
High School: Lake Howell High
Tax Year: 2025
Middle School: Tuskawilla Middle
Remarks: Welcome to 8433 Commander Cove, ideally situated on a quiet cul-de-sac in the highly sought-after Trinity Bay community. Upon entering this spacious home you're greeted by soaring vaulted ceilings, a formal dining area, and a stunning cathedral-style front window that fills the space with natural light. The separate enclosed kitchen offers functionality and charm, with French doors leading to a covered, tiled lanai. Step outside and enjoy a large patio surrounded by mature trees and lush landscaping—an ideal setting for morning coffee, outdoor entertaining, and family barbecues. The inviting family room showcases vaulted ceilings, a grand brick fireplace, and a versatile bonus den/office with a window, perfect for working from home or additional living space. Conveniently located off the family room is an indoor laundry area and half bath. The first-floor primary suite offers privacy and comfort, featuring a dual-vanity bathroom and private French door access to the covered lanai. Upstairs, you'll find three generously sized bedrooms, each equipped with ceiling fans and ample closet space, along with a second dual-vanity full bathroom. Whether you're a first-time homebuyer or looking for room to accommodate a growing family, this home offers exceptional value and functionality. Residents of Trinity Bay enjoy access to a community pool, community playground, and a private neighborhood boat ramp with access to the Lake Burkett and Lake Martha Chain of Lakes, where boating, water skiing, fishing, and other recreational activities are welcomed. Don't miss this opportunity to own a beautiful home in one of the area's most desirable neighborhoods!
Listing is courtesy of: CEPEDA REAL ESTATE LLC (407-900-1792)
Listing Agent: Brandi Cepeda (407-900-1565)
1914 BONANZA CT, WINTER PARK, FL 32792
$429,99975 Days on yellowkey MLS ID: O6408461
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1727 Built: 1968 Tax: $4,497 (2025)Community: Eastbrook Sub Unit 13Single Family
Taxes:$4,497
Remarks: Welcome to your winter Park retreat! Step into this beautifully renovated 3 bedroom, 2 bathroom home where modern meets timeless comfort. Designed with an open floor plan, the living space flows seamlessly, making it perfect for both entertaining and everyday living. The brand new kitchen shines with contemporary finishes, while the new flooring throughout the home adds warmth and style. Both bathrooms have been thoughtfully renovated, offering a clean and modern feel. The Florida room, wrapped in huge windows. floods the home with natural light, creating a bright and inviting space you'll love year round. Step outside to enjoy a covered patio, ideal for morning coffee or relaxing evenings with friends and family. With its prime location, this home is a blend of convenience, charm, and modern living ready for you to make it your own. Call and schedule your showing today!
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Judy Julien, Pa (407-234-4051)
4353 STEED TER, WINTER PARK, FL 32792
$614,99034 Days on yellowkey MLS ID: TB8517548
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2275 Built: 1989Monthly Fee: $29 Tax: $7,031 (2024)Community: Kings CoveSingle Family
Taxes:$7,031
Elementary School: Red Bug Elementary
Tax Year: 2024
Remarks: MOTIVATED SELLER – QUICK CLOSE AVAILABLE! Welcome to this beautifully maintained 4-bedroom, 2-bath home in the desirable Kings Cove community of Winter Park. From the moment you arrive, you'll appreciate the spacious layout and impressive updates throughout. The heart of the home features a beautifully appointed kitchen with quartz countertops, ample cabinetry, and a seamless flow into the family room, making it perfect for everyday living and entertaining. Vaulted ceilings and a cozy wood-burning fireplace create a warm and inviting atmosphere. Step outside to your own private outdoor oasis. The screened-in pool area is designed for year-round enjoyment and features a spacious patio, covered lanai, and a fully equipped outdoor kitchen complete with refrigerator, sink, and cabinetry—ideal for hosting family and friends. The primary suite offers a relaxing retreat with dual sinks and plenty of space to unwind. Additional highlights include a fenced backyard, new windows (2021), new roof (2019), and a new AC system (2024), providing peace of mind for years to come. Conveniently located with easy access to SR 417, shopping, dining, and everyday conveniences, this exceptional home combines comfort, style, and location. Don't miss this opportunity—schedule your private showing today!
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Barbara Robinson (706-540-4593)
525 S LAKEMONT AVE, WINTER PARK, FL 32792
$2,099,99051 Days on yellowkey MLS ID: O6414770
REDUCED by $99,010 (4.5%) on 07/14/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3330 Built: 2026 Tax: $7,133 (2024)Community: Kenilworth Shores Sec 01Spa: YesSingle Family
Taxes:$7,133
Elementary School: Brookshire Elem
High School: Winter Park High
Middle School: Glenridge Middle
Remarks: Winter Park Luxury Awaits You! Welcome to your dream home—a stunning custom-built luxury residence offering the perfect blend of elegance, comfort, and modern design. Featuring 4 spacious bedrooms and 4 beautifully appointed bathrooms, this masterpiece showcases custom cabinetry and closets throughout, ensuring every space is both functional and refined. The chef’s kitchen is a true showpiece, complete with a coffee bar, walk-in pantry with customized shelving and designer lighting, and seamless flow into the open-concept living and dining areas. A wine room adds sophistication and convenience for the entertainer at heart. Upstairs, enjoy a spacious loft area with a wet bar, perfect for hosting guests or creating an additional entertainment lounge. Step outside to your private outdoor oasis, featuring a heated pool, fireplace, outdoor kitchen, and surround sound system—designed for year-round entertaining and relaxation. This home is pre-wired for security cameras and enhanced by custom landscaping and lighting, offering beauty and privacy from day to night. Located in highly sought-after Winter Park, Florida, near world-class dining, shopping, and top-rated schools. Contact us today for a private showing!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)
Listing Agent: Nicole Cates (407-948-6000)
1438 TIERRA CIR, WINTER PARK, FL 32792
$514,90088 Days on yellowkey MLS ID: O6403855
REDUCED by $5,000 (1.0%) on 06/24/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1627 Built: 1968 Tax: $1,630 (2024)Community: Casa AlomaSpa: NoSingle Family
Taxes:$1,630
Elementary School: None
High School: None
Middle School: None
Remarks: Charming, Fully Renovated Pool Home in Sought-After Winter Park. Welcome to this beautifully updated pool home, ideally located in desirable Winter Park—just minutes from premier shopping, dining, and entertainment, with easy access to major roadways for a seamless commute. From the moment you step inside, you’re greeted by a warm, modern aesthetic that blends comfort with style. To the right, a spacious step-down living room offers abundant natural light and lovely views of the front yard. To the left, the formal dining room flows effortlessly into the heart of the home—a stunning, fully renovated kitchen and inviting family room overlooking the private pool and patio. The kitchen is designed to impress, featuring solid wood cabinetry, stainless steel appliances, sleek modern lighting, ample counter space, and a center island perfect for gathering. The adjoining family room is anchored by a stylish electric fireplace, creating a cozy ambiance while offering serene views of the outdoor living area. This home features a desirable split-bedroom floor plan, providing privacy and flexibility. The primary suite is tucked away on one side, while two additional bedrooms and a full bathroom are located on the opposite wing—ideal for family or guests. Extensive upgrades provide peace of mind and modern appeal, including a newer roof (2021), a newer AC (2019) fully renovated kitchen and bathrooms, 5-inch baseboards, knockdown ceiling texture, textured walls, luxury vinyl plank flooring throughout, fresh interior and exterior paint, and updated electrical and plumbing fixtures. Step outside to your private oasis—a fully fenced backyard with a screened-in pool enclosure and lanai, perfect for relaxing or entertaining year-round in true Florida style. This move-in-ready gem truly has it all. Don’t miss your opportunity—schedule your private showing today!
Listing is courtesy of: COLDWELL BANKER REALTY (407-333-8088)
Listing Agent: Tony Nicolas (630-514-9342)
1886 CLEMATIS LN, WINTER PARK, FL 32792
$425,0005 Days on yellowkey MLS ID: O6428045
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1238 Built: 1960 Tax: $4,330 (2025)Community: Eastbrook Sub Unit 06Spa: NoSingle Family
Taxes:$4,330
Remarks: Discover the epitome of comfortable living in this fantastic single-family home situated on a generous and spacious corner lot. This meticulously renovated property features 3 bedrooms and 2 bathrooms, offering a perfect blend of modern style and cozy charm. Step inside to experience the allure of an open floor plan that seamlessly connects the living spaces. The kitchen, fully renovated and boasting a contemporary design, is the heart of this home—a perfect gathering place for family and friends. Indulge in the luxury of a private backyard oasis, where tranquility meets outdoor enjoyment. A delightful retreat awaits with a nice backyard, ideal for entertaining or simply unwinding under the stars. Plus, your vehicles and recreational gear are well taken care of with a 2-car garage and an additional boat space. The charm continues outdoors with a great covered lanai, providing the perfect setting for al fresco dining or cozy evenings by the fireplace. Every detail of this home has been thoughtfully curated to enhance your lifestyle. Don't miss the opportunity to make this Winter Park residence your own—where spacious living, thoughtful design, and comfort converge. Schedule your tour today and envision the possibilities that await in this truly remarkable home!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Steven Greening (407-595-7917)
1000 S SEMORAN BLVD #305, WINTER PARK, FL 32792
$129,0005 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)
5409 ALBERT DR, WINTER PARK, FL 32792
$430,0005 Days on yellowkey MLS ID: C7528794
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1483 Built: 1977 Tax: $5,337 (2025)Community: Howell Branch WoodsSingle Family
Taxes:$5,337
Remarks: Virtually Staged. Discover this spacious 3-bedroom, 2-bathroom home offers 1,483 sq ft of comfortable living space with a functional layout and plenty of room for everyday living. The home features a well-appointed kitchen, open living areas, and generously sized bedrooms. Outside, enjoy a private backyard with a swimming pool, creating the perfect space for relaxing, entertaining, and enjoying the Florida lifestyle.
Listing is courtesy of: SOVEREIGN REAL ESTATE GROUP (305-662-1502)
Listing Agent: Raul Pino (305-662-1502)
3562 BOUGAINVILLEA DR, WINTER PARK, FL 32792
$339,0005 Days on yellowkey MLS ID: O6427582
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1149 Built: 1960 Tax: $2,805 (2025)Community: Eastbrook Subd Unit No 05Single Family
Taxes:$2,805
Remarks: Welcome to this beautifully updated 3-bedroom, 2-bath home in beautiful Winter Park! This move-in-ready property features stylish wood-look tile flooring throughout, creating a seamless, modern look that's both attractive and easy to maintain. The home has two beautifully renovated bathrooms with contemporary finishes, along with a newer A/C and a new roof in 2026. The air-conditioned laundry room has plenty of storage space. Step outside to your spacious, fully fenced backyard, where you'll find plenty of room to entertain, play, or unwind around the cozy fire pit. The generous outdoor space offers endless possibilities for gatherings, gardening, or simply enjoying Florida's beautiful weather. A rare highlight is the oversized swing gate providing convenient side-yard access with ample room to park an RV, boat, trailer, or other recreational vehicles. Best of all, there's no HOA, giving you the freedom to make the most of your property without additional HOA restrictions. Perfectly situated just minutes from Costco, grocery stores, shopping, dining, and the popular Cady Way Trail, this home offers the ideal combination of comfort, convenience, and outdoor recreation. With easy access to major roadways and everything Winter Park has to offer, this home truly has it all. Welcome home!
Listing is courtesy of: SHORESTONE PROPERTY GROUP (407-452-9818)
Listing Agent: Tania Crandall (407-452-9818)
777 HALIFAX AVE, WINTER PARK, FL 32792
$1,500,00019 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
$575,00019 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)
7488 WHISPERWOOD DR #28, WINTER PARK, FL 32792
$220,00036 Days on yellowkey MLS ID: O6419151
REDUCED by $10,000 (4.3%) on 07/17/2026
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1578 Built: 1974Monthly Fee: $575 Tax: $3,078 (2025)Community: Whisperwood CondoCondo
Taxes:$3,078
Elementary School: Cheney Elem
Remarks: Rare Two-Story 2BR/2.5BA Condo with Two Private Suites in Winter Park. Highlights: Two-story floor plan condominium with a townhome-style layout, 2 spacious bedrooms, each with its own private ensuite bathroom, 2.5 bathrooms, Functional kitchen with stainless steel appliances, Open-concept living and dining area, Private fenced patio – perfect for relaxing, grilling, or entertaining, Covered parking plus additional guest parking, Community pool. The HOA covers exterior maintenance, roof, trash, landscaping and community pool, allowing owners to enjoy a low maintenance lifestyle. Why You'll Love It !! This well maintained townhome offers the perfect combination of comfort, convenience, and value. The bright, open floor plan is ideal for everyday living, while the two upstairs ensuite bedrooms provide privacy for homeowners, guests, or roommates. Enjoy your morning coffee or unwind in the evening on the private fenced patio—your own outdoor retreat. Prime Winter Park Location: Conveniently located just minutes from: Full Sail University, University of Central Florida (UCF), Downtown Winter Park, Major highways (417 & 408), Shopping, dining, parks, and entertainment Great Opportunity, Whether you're a first-time homebuyer, downsizing, or looking for an investment property, this home offers exceptional value in one of Central Florida's most convenient locations. Schedule your private showing today and discover everything this Winter Park townhome has to offer.
Listing is courtesy of: PARKVIEW REAL ESTATE (407-312-6472)
Listing Agent: Miranda Azer (407-312-6472)
1369 BLUE STEM LN, WINTER PARK, FL 32792
$799,000113 Days on yellowkey MLS ID: O6396971
REDUCED by $20,000 (2.4%) on 07/24/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2589 Built: 2021Monthly Fee: $413 Tax: $6,074 (2024)Community: Landings At Hawks CrestSingle Family
Taxes:$6,074
Remarks: Nestled in one of the most sought-after neighborhoods in Winter Park, this exceptional gated residence offers the perfect blend of elegance, comfort, and modern efficiency. Ideally located just five minutes from top-rated private schools, this two-story single-family home is designed for both luxurious living and everyday functionality. Upon entry, you are welcomed by a dramatic grand foyer featuring soaring ceilings of nearly 20 feet, creating an impressive and light-filled living space. The open layout seamlessly connects the main living areas, ideal for entertaining and family gatherings. This thoughtfully designed home features 4 spacious bedrooms and 3.5 bathrooms, including dual primary suites—one conveniently located on the main level and another upstairs—providing flexibility for multi-generational living or guest accommodations. A dedicated private office on the first floor offers the perfect work-from-home environment. Step outside to a beautifully maintained backyard with premium artificial turf, fully fenced for privacy, and a screened rear patio—perfect for relaxing or enjoying Florida’s outdoor lifestyle year-round. Extensively upgraded throughout, the home showcases high-quality finishes with no carpet—featuring elegant flooring and tile across all living areas, along with a solid wood staircase that adds warmth and sophistication. The garage is equally well-appointed with a premium epoxy-coated floor, offering both durability and a clean, polished look. Energy efficiency is a standout feature of this home, equipped with a tankless water heater for on-demand hot water and reduced energy consumption, as well as solar panels that help significantly lower utility costs. This is a rare opportunity to own a meticulously upgraded home in a prime Winter Park location—ideal as a primary residence or a high-potential investment property.
Listing is courtesy of: U S GLORY REALTY (407-222-7801)
Listing Agent: He Gao (407-955-0138)
7426 BLUE JACKET PL E, WINTER PARK, FL 32792
$324,9006 Days on yellowkey MLS ID: O6427029
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1150 Built: 1971 Tax: $753 (2025)Community: Woodcrest Unit 03Single Family
Taxes:$753
Remarks: Virtually Staged. Opportunity Awaits in the Heart of Winter Park! Welcome to 7426 Blue Jacket Place, a 3-bedroom, 2-bathroom home that's ready for its next chapter. Nestled on a quiet street in an established neighborhood, this property offers a fantastic opportunity for buyers looking to add their personal touch and create the home of their dreams. Plus, enjoy added peace of mind knowing the roof was replaced approximately six years ago. Inside, you'll find a spacious layout featuring a large living area, a functional kitchen with an adjoining dining space, and generously sized bedrooms. The screened-in porch is the perfect place to relax and enjoy the peaceful backyard. Step outside and discover one of this home's standout features—a beautiful, mature camphor tree that creates a picturesque backyard retreat with plenty of shade and room to garden, entertain, or simply unwind. The property also includes a storage shed, ample outdoor space for endless possibilities, and an existing 25-foot-deep well on the property, offering potential for future use. Conveniently located near shopping, dining, major roadways, parks, and all the highly sought-after Winter Park amenities, this home offers an unbeatable location with tremendous potential. Whether you're a first-time homebuyer, investor, or someone looking for a renovation project, this is an opportunity you won't want to miss. Bring your vision and make 7426 Blue Jacket Place your own!
Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)
Listing Agent: Abby Nelson (407-571-1445)
1456 E BROOKSHIRE CT, WINTER PARK, FL 32792
$449,00012 Days on yellowkey MLS ID: O6425661
2 Days Off yellowkey (back on 7/24/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1673 Built: 1987Monthly Fee: $33 Tax: $4,650 (2025)Community: Hyde ParkSingle Family
Taxes:$4,650
Remarks: Under contract-accepting backup offers. Tucked away on a peaceful cul-de-sac, this beautifully updated Winter Park gem offers the perfect blend of modern style, functional design, and peace of mind. From the moment you arrive, the quiet setting welcomes you home to 1456 E. Brookshire Court. Step inside to discover a bright and airy interior featuring soaring vaulted ceilings that elevate the main living areas, creating a spacious and grand atmosphere. The thoughtfully designed split floor plan ensures maximum privacy, separating the serene primary suite from the additional bedrooms. Throughout the home, tasteful interior upgrades provide a sleek, move-in-ready aesthetic. Major highlights include brand new roof installed in 2020 for years of low-maintenance ownership. Enjoy the outdoor oasis out back complete with paver patio overlooking an expansive, deep backyard—perfect for weekend barbecues, play, or designing your dream pool. Zoned for highly sought-after Seminole County Public Schools while offering easy access to local dining, shopping, and parks. Don't miss the opportunity to own this turn-key retreat in a prime Winter Park location. Schedule your private showing today
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Steven Luppert (407-484-9178)
885 CARNATION DR, WINTER PARK, FL 32792
$385,00017 Days on yellowkey MLS ID: S5153456
INCREASED by $10,000 (2.7%) on 07/24/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1240 Built: 1959 Tax: $5,196 (2025)Community: Eastbrook SubSingle Family
Taxes:$5,196
Remarks: Beautifully updated 4-bedroom, 2-bath pool home in Winter Park offering modern upgrades and flexible living space. The home features new tile flooring throughout, a fully renovated kitchen with a stunning waterfall quartz island, and two beautifully remodeled bathrooms. The garage has been updated with new flooring and a new garage door. Major improvements include a new roof (2024), new A/C (2023), complete home repipe (2022), updated electrical panel, and pavers in both the front and back of the home. The swimming pool was resurfaced with new tile in 2023 and is approximately 12 feet deep, creating the perfect backyard retreat.
Listing is courtesy of: RADIUS REALTY GROUP LLC (407-541-0779)
Listing Agent: Tashania Brown (321-442-2512)
2703 TIERRA CIR, WINTER PARK, FL 32792
$469,0006 Days on yellowkey MLS ID: O6427460
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1737 Built: 1970 Tax: $1,360 (2025)Community: Casa AlomaSingle Family
Taxes:$1,360
Elementary School: English Estates Elementary
Remarks: Okay, let's talk about this one. Yes, there's green carpet. Yes, it needs your vision. I know exactly what you're thinking right now. But hear me out, because this house has some things going for it that are genuinely hard to find. Start with the location. In under 10 minutes in any direction, you could be having lunch on Park Ave, shopping at Altamonte Mall, or launching your boat up in Maitland. That kind of range is rare in Central Florida, and this spot has it. And there's no HOA here, which if you know, you know. Then there's the pool. A real pool, tucked behind a block wall for total privacy, so you can actually enjoy it without the whole street watching. That kind of setup doesn't come around often. This is a 3 bedroom, 2 bath home with real bones and real space. The layout gives you room to breathe, and the systems that actually matter have already been taken care of. Water heater, brand new in 2026. HVAC, also brand new in 2026. Roof was done in 2025. Plumbing was updated in 2017. So the expensive, unglamorous stuff, the stuff that actually protects your investment, is already handled. The home has been professionally cleaned and pressure washed, so it's not just clean, it's move in ready clean. You could genuinely move in as is and update it slowly, on your own timeline, as your taste and budget allow. No rush. No pressure. Just a solid home with good bones, a pool, an unbeatable location, and all the boring but important stuff already done for you. Sometimes the right house isn't the one that's already finished. It's the one that's ready for you to finish it.
Listing is courtesy of: EXP REALTY LLC (407-305-4300)
Listing Agent: Tony Ubaldini (407-250-9237)
814 DENSMORE DR, WINTER PARK, FL 32792
$425,000104 Days on yellowkey MLS ID: O6399773
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1610 Built: 1960 Tax: $5,402 (2025)Community: Winter Park EstatesSingle Family
Taxes:$5,402
Remarks: Welcome to this charming home situated on a spacious lot in a quiet, established neighborhood in Winter Park. From the moment you arrive, you’ll appreciate the inviting curb appeal, expansive front yard, and peaceful setting that make this property feel like home. Inside, the home offers a light and open layout with a seamless flow between the living, dining, and kitchen spaces—perfect for both everyday living and entertaining. The updated kitchen features modern cabinetry, granite countertops, stainless steel appliances, and a functional layout with bar seating, making it both stylish and practical. The bedrooms are comfortably sized with great natural light, offering flexibility for family, guests, or a home office. The bathrooms have been thoughtfully updated, including a beautifully renovated shower with modern tilework that adds a fresh, clean feel. The Florida room in the back creates a relaxing space for drinking coffee or curling up for a family movie night. Step outside to a generously sized backyard with endless potential—whether you envision creating an outdoor entertaining space, adding a pool, or simply enjoying the open green space. With plenty of room to spread out, this yard offers the kind of flexibility that’s hard to find. Conveniently located near local shopping, dining, and major roadways, this home offers both comfort and accessibility. Zoned for great Winter Park schools. Whether you’re a first-time buyer, investor, or looking to downsize, this property presents an incredible opportunity to own a home with room to make it your own.
Listing is courtesy of: ORANGE SLICE PROPERTIES (863-632-9765)
Listing Agent: Liz Jones (407-619-6345)
616 BRECHIN DR, WINTER PARK, FL 32792
$999,00068 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
$230,0006 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)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.