Displaying: For Sale
Location: Winter Park
Property Type(s): Single Family
Beds: 3 to 3
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Winter Park - 103 properties found
3207 LOWNDES DR, WINTER PARK, FL 32792
$485,000146 Days on yellowkey MLS ID: O6362285
0 Days Off yellowkey (back on 5/31/2026)
REDUCED by $10,000 (2.0%) on 04/23/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2028 Built: 1967 Tax: $4,172 (2024)Community: Georgetown EstatesSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,172
Elementary School: Lakemont Elem
High School: Winter Park High
Tax Year: 2024
Middle School: Maitland Middle
Remarks: Under contract-accepting backup offers. 3 bedrooms PLUS an office (or 4th bedroom) AND a "flex space". Easy access to all of Winter Park, UCF, and south Seminole County from this convenient, central location! If you've been searching for a spacious pool home with plenty of space for playing, entertaining, or even working from home -- you've found it here! When you walk in, you'll appreciate the intuitive flow of living space into the kitchen, with built-in eating space. Off of the kitchen, you'll find a bonus space (perfect for an office or home gym) as well as a large indoor laundry room/mudroom, and the converted garage which is ideal for a playroom or secondary living space. On the other side of the home, 2 secondary bedrooms, an oversized hall bathroom, and a primary with en suite bath. There are additional touches that go a long way, too, including the custom plantation shutters throughout the home and updated countertops in the kitchen. Much of your time will be spent in the backyard, enjoying a fenced in pool, screened porch, new custom shed (2025), and fully fenced yard with turf play area. Systems in the home have been well maintained: roof (2017), HVAC (2017), tankless gas water heater (2018), and brand new electrical updates (2026). The home was also re-plumbed in 2008.
Listing is courtesy of: MILLER GRANT AND COMPANY (407-399-6031)
Listing Agent: Courtney Pelfrey (407-454-0538)
2157 LAKE DR, WINTER PARK, FL 32789
$689,00026 Days on yellowkey MLS ID: O6412258
REDUCED by $70,000 (9.2%) on 05/31/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2124 Built: 1962 Tax: $1,605 (2025)Community: Killarney PointSingle Family
Taxes:$1,605
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Welcome to this beautifully maintained Winter Park home in coveted 32789, offering over 2,600 square feet, peekaboo Lake Killarney views, and a peaceful setting on a quiet private lakefront street. From the moment you enter, pride of ownership shines through, with custom built-ins throughout creating stylish and functional living spaces. The heart of the home is the updated kitchen and dining area, featuring high-end bamboo floors, stainless steel appliances, real wood custom cabinetry, and a large island overlooking a versatile flex space perfect for a formal living room, den, or office. The spacious great room is warm and inviting with a wood-burning fireplace and a dramatic wall of four French doors that fill the space with natural light. The elegant primary suite offers a walk-in closet and a spacious bath with dual vanities, a soaking tub, and separate shower. Step outside to a covered patio and expansive backyard with plenty of room to entertain, garden, or unwind. Just minutes from Park Avenue, premier shopping, dining, and Winter Park’s beloved parks and amenities, this is a rare opportunity to own a move-in-ready home in one of Central Florida’s most sought-after neighborhoods on .33 acres. Brand new roof and newer AC for total peace of mind. Schedule a private tour today.
Listing is courtesy of: SHORES REAL ESTATE (407-353-0106)
Listing Agent: Jacob Johnson (407-353-0106)
1433 ASTER CT, WINTER PARK, FL 32792
$389,00042 Days on yellowkey MLS ID: O6407873
0 Days Off yellowkey (back on 5/29/2026)
REDUCED by $10,000 (2.5%) on 05/21/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1363 Built: 1984 Tax: $1,057 (2025)Community: Garden Lake Estates Unit 3Single Family
Taxes:$1,057
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to this charming 3-bedroom, 2-bath home with a 2-car garage, perfectly situated on a quaint, low-traffic street. This thoughtfully designed split floor plan offers both privacy and functionality, while soaring vaulted ceilings create an open, spacious feel throughout. The updated kitchen serves as the heart of the home, offering modern touches and great flow for everyday living or entertaining. Enjoy peace of mind with a newer A/C, adding comfort and value for years to come. Step outside to a fully fenced backyard overlooking a tranquil pond—perfect for relaxing, entertaining, or enjoying Florida’s beautiful weather. Whether you’re a first-time buyer, downsizing, or looking for a smart investment property, this home offers the ideal combination of comfort, charm, and opportunity in Florida.
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Dominick Florio (321-377-4045)
1340 PLACE PICARDY, WINTER PARK, FL 32789
$1,599,000133 Days on yellowkey MLS ID: O6382113
3 Days Off yellowkey (back on 3/30/2026)
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3459 Built: 1997 Tax: $7,515 (2025)Community: FontainebleauSingle Family
Taxes:$7,515
Elementary School: Dommerich Elem
Remarks: Under contract-accepting backup offers. Set on an oversized 1/3-acre lot in the heart of Winter Park, this one-owner home was custom built in 1997 and has been meticulously maintained ever since. Solid block construction, timeless stone accents, and mature landscaping give it great curb appeal from the moment you arrive. Step inside to a spacious foyer with hardwood floors that carry through most of the main living areas. To the right, the living room features built-in shelving and a bay window that fills the space with natural light. It flows into the formal dining room, also with hardwood floors, plantation shutters, and plenty of room to host. A conveniently located powder bath serves this side of the home. To the left is the heart of the house - a generously sized kitchen with abundant white cabinetry, stone countertops, a center island, double ovens, a built-in pantry with pull-out storage, and a breakfast bar. The separate eat-in area overlooks the backyard and opens to the screened porch through French doors. The kitchen connects to a large family room with coffered ceilings, a gas fireplace, built-ins, and additional French doors leading outside. The home offers a three-way split floor plan for privacy. The primary suite sits on its own wing and is very spacious, featuring crown molding, a bay window, and French doors to the patio. The en-suite bath includes double vanities, large "His & Hers" walk-in closets with custom closet systems, a soaking tub, separate shower, and private water closet. On the opposite side of the home, you’ll find a generously sized secondary bedroom with its own en-suite bathroom and walk-in closet. Toward the back of the house is a third bedroom with a built-in desk, French doors to the exterior, and an en-suite Jack-and-Jill bath that also serves the family room. The first floor also includes an indoor laundry room with ample cabinetry and a utility sink. Upstairs, a huge bonus room offers incredible flexibility - game room, media room, office, or potential fourth bedroom. There is also space to add a bathroom if desired. Out back, a large screened porch with high ceilings overlooks a peaceful, lushly landscaped yard with plenty of room to enjoy Florida living. Additional features include plantation shutters throughout, a spacious two-car garage, and an unbeatable location just minutes from Park Avenue’s shopping and dining. Zoned for highly rated Dommerich Elementary, Maitland Middle, and Winter Park High. Call today to schedule your private showing!
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Maria Van Warner (407-256-8066)
1092 EASTBROOK BLVD, WINTER PARK, FL 32792
$399,00040 Days on yellowkey MLS ID: O6407251
REDUCED by $11,000 (2.7%) on 05/27/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1122 Built: 1959 Tax: $4,373 (2025)Community: Eastbrook SubSingle Family
Taxes:$4,373
Remarks: Remodeled pool home located in the highly sought after desirable Winter Park school district. This property has a.27 acre corner lot with room to expand and a pool/spa perfect for relaxing or entertaining guest.Inside the living room features vaulted ceilings that create a bright open feeling and a huge screened in patio for outdoor entertaining. The bathrooms have been beautifully remodeled, there are new windows, new electric outlets throughout, new light fixtures, roof replaced in 2022,kitchen beautifully redone 2020 with new cabinets and Granite counter tops. Additional upgrades throughout the home include new luxury vinyl flooring, new vanity in master bath, new enhanced pool liner, new robot pool vacuum, new garage door house has been painted inside and out. The location is close to shopping, Costco and other stores also located near by. Full Sale, Rollins College and downtown Winter Park to the west and UCF to the East within close proximity. This is a must see. Owner is realtor.Buyer to verify room measurements.
Listing is courtesy of: JC FLORIDA REALTY LLC (407-257-8265)
Listing Agent: Eva Firios (321-662-1501)
621 HUNTINGTON AVE, WINTER PARK, FL 32789
$1,795,00086 Days on yellowkey MLS ID: O6394464
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2399 Built: 2008 Tax: $12,854 (2025)Community: Winter Park RevSpa: NoSingle Family
Taxes:$12,854
Elementary School: Audubon Park K8
Middle School: Audubon Park K-8
Remarks: Experience elevated living in this fully transformed luxury residence in the heart of Winter Park, where design, premium finishes, and effortless functionality come together seamlessly. This 3-bedroom, 3.5-bath pool home offers approximately 2,400 square feet of impeccably curated living space, designed for those who appreciate both style and substance. Expertly designed by Morrone Interiors, every detail reflects a refined, cohesive aesthetic. Step inside to warm oak wood floors and a light-filled open-concept layout ideal for both everyday living and upscale entertaining. The chef’s kitchen is a true statement, featuring custom oak cabinetry, sleek quartz countertops with a dramatic waterfall island, and an expansive breakfast bar. Top-of-the-line appliances include a Sub-Zero refrigerator, Wolf 6-burner gas professional range with grill and double ovens, Wolf microwave, Miele dishwasher with PowerDisk system, and a built-in Miele coffee station. The kitchen flows effortlessly into both a breakfast nook and a separate dining area, while the designer bar serves as a stunning focal point—complete with two Sub-Zero dual zone wine refrigerators accommodating more than 200 bottles, along with additional Sub-Zero refrigerator and freezer drawers. Downstairs all blinds are motorized and have gorgeous custom drapes. Upstairs, all three bedrooms are en suite, offering a private retreat for family and guests. A versatile loft area features a custom-designed laundry space concealed behind built-in cabinetry for a clean, streamlined aesthetic. One bedroom has been thoughtfully designed as a home office with a built-in Murphy bed, providing flexibility without compromising luxury. The outdoor space is equally refined, featuring low-maintenance turf, a beautifully designed pool, and a covered lanai perfect for relaxing or entertaining. A built-in grill area and lush privacy hedging create a serene backyard oasis, with landscaping professionally designed and maintained by Signature Landscaping. Additional highlights include a 2-car garage and a Sonos sound system in the living room and lanai, enhancing the home’s elevated lifestyle experience. Most furnishings are available for purchase separately, offering a truly turnkey, designer-furnished opportunity. Ideally located just minutes from Park Avenue, top-rated schools,Rollins College, fine dining, and boutique shopping, this exceptional home represents the very best of Winter Park luxury living. Perfect lock and leave home with the perfect location!
Listing is courtesy of: OLDE TOWN BROKERS INC (407-425-5069)
Listing Agent: Noelle Leblanc (407-491-2744)
1600 S PENNSYLVANIA AVE, WINTER PARK, FL 32789
$1,200,00045 Days on yellowkey MLS ID: NS1088189
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2158 Built: 1958 Tax: $5,218 (2025)Community: Banks Colonial EstatesSpa: YesSingle Family
Taxes:$5,218
Remarks: Welcome to this charming 3 bedroom, 2 bath home located in the highly desirable area of Winter Park. Situated on an oversized lot, this property offers both comfort and space with a layout designed for everyday living and entertaining. The home features a inviting living area along with a unique sunken sunroom just off the two-car garage; perfect for a relaxing sitting room, home office, or play space. The well-appointed kitchen and dining areas flow easily into the main living spaces, creating a warm and functional environment for family and guests. Step outside to your private backyard retreat where you’ll find a sparkling pool and hot tub surrounded by a huge yard, offering plenty of room for outdoor gatherings, gardening, or simply enjoying Florida living. With its generous lot size, thoughtful layout, and prime Winter Park location close to shopping, dining, and top-rated schools, this home is a wonderful opportunity for anyone looking to enjoy the best of Central Florida living.
Listing is courtesy of: EXIT REAL ESTATE PROPERTY SOL (386-763-3008)
Listing Agent: Jami Giles (386-478-8284)
1617 CHILEAN LN, WINTER PARK, FL 32792
$367,500161 Days on yellowkey MLS ID: O6373026
1 Days Off yellowkey (back on 5/15/2026)
REDUCED by $2,400 (0.6%) on 04/30/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1359 Built: 1960 Tax: $3,432 (2024)Community: Eastbrook Sub Unit 05Single Family
Taxes:$3,432
Elementary School: Eastbrook Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Back on the market and better than ever! New water heater and minor repairs addressed and ready for the new owner! Come see this newly renovated home in the Eastbrook neighborhood of Winter Park. Offering 3 bedrooms and 2 full baths it’s the perfect sanctuary for families and entertainers alike. You will enjoy the bright, airy feel of the open floor plan accentuated by the vaulted ceilings that flood the space with natural light. The stylish interior includes luxury vinyl plank flooring throughout, complemented by elegant tile in the bathrooms and laundry room. Relax in not one, but two generous living areas, perfect for family gatherings, entertaining or cozy nights in. Cook like a pro in your eat-in kitchen featuring brand new ENERGY STAR stainless steel appliances, ample cabinetry, and convenient carport access for effortless unloading. The generous backyard provides a private oasis for outdoor activities, barbecues, and gardening enthusiasts. Plus, the expansive driveway and two-car carport ensure plenty of parking for your guests. Recent upgrades include ceiling fans, blinds, fresh paint, stainless steel appliances, a newer roof (2017) and a well-maintained air conditioner (only 4 years old) ensuring peace of mind for years to come. Located in Seminole County, known for great schools and in a community with NO HOA fees, giving you the freedom to enjoy your space. Plus, you're just moments away from shopping, dining, and parks!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Brenda Feliciani (407-405-0931)
1725 CAROLLEE LN, WINTER PARK, FL 32789
$1,005,00059 Days on yellowkey MLS ID: O6402656
0 Days Off yellowkey (back on 5/22/2026)
REDUCED by $10,000 (1.0%) on 05/12/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2335 Built: 1960 Tax: $8,445 (2025)Community: Green TerraceSingle Family
Taxes:$8,445
Elementary School: Brookshire Elem
Middle School: Glenridge Middle
Remarks: Nestled in one of Winter Park’s most sought-after neighborhoods, this charming and meticulously maintained home offers three bedrooms, two baths, an open floor plan, hardwood floors, and thoughtful updates throughout. Recent improvements include a new AC, new hot water heater, new driveway and walkway pavers, and refreshed front and backyard landscaping featuring a magnolia tree, camellias, gardenias, and more. Just minutes from Park Avenue’s beloved restaurants, cafés, and boutiques, as well as the scenic Winter Park Chain of Lakes, this home offers both character and convenience. With easy access to I-4, SR-417, Orlando International Airport, and top-rated schools, it is a wonderful opportunity to enjoy classic Winter Park charm in a beautifully cared-for home.
Listing Agent: Kyle Grafton (203-246-8512)
2973 SANBINA ST, WINTER PARK, FL 32789
$377,88041 Days on yellowkey MLS ID: O6407521
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1128 Built: 1965 Tax: $5,253 (2025)Community: Howell HeightsSingle Family
Taxes:$5,253
Remarks: Welcome to an incredible opportunity to own a home in one of Central Florida’s most desirable zip codes — Winter Park 32789 — for under $400,000! Surrounded by million-dollar neighborhoods, this 3-bedroom, 2-bath home offers outstanding value, endless potential, and a prime location close to shopping, dining, parks, and everything Winter Park has to offer. Located in a highly sought-after school district featuring Dommerich Elementary School, Maitland Middle School, and Winter Park High School, this property is ideal for homeowners and investors alike. Inside, you’ll find a Great Room floor plan with a separate dining room, split-bedroom layout, neutral interior paint and luxury vinyl plank flooring installed just four years ago throughout the home. The galley kitchen offers functional space and flows easily into the main living areas, while updated vanities and ceiling fans throughout add comfort and style. A large inside laundry room provides additional convenience. Sliding glass doors lead to a screened back porch overlooking the expansive backyard on this .23 acre lot — offering plenty of room to entertain, garden, expand, or create your dream outdoor retreat. Additional features include a 1-car carport and strong long-term investment appeal, as this property has been income-producing for decades. Whether you’re looking to personalize your forever home, secure a valuable investment, or break into Winter Park’s premier 32789 zip code at an exceptional price point, this property is packed with opportunity!
Listing is courtesy of: SUN PROPERTIES, INC. (407-645-5700)
Listing Agent: Andrew Musashe (407-645-5700)
1960 WINTER PARK RD, WINTER PARK, FL 32789
$899,00049 Days on yellowkey MLS ID: O6406091
0 Days Off yellowkey (back on 5/20/2026)
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1864 Built: 1948 Tax: $7,103 (2025)Community: CharmontSpa: NoSingle Family
Taxes:$7,103
Remarks: Under contract-accepting backup offers. Discover the perfect canvas for your dream home at 1960 Winter Park Road! With utilities and sewer connected, plus a complete roof replacement in 2019, newer gutters with gutter guards added in 2020, and various new appliances and thoughtful upgrades since, this ¼-acre lot presents the ideal opportunity to either build new, or remodel. Zoned for the highly esteemed Audubon K-8 School, this property offers an ideal location nestled in one of the most coveted pockets of Winter Park. Stroll down the brick-lined street and land at East End market, Kelly’s Homemade Ice Cream, and all the shops and restaurants along the vibrant Corrine Drive corridor; walk around the corner to Blue Jacket Park; or venture North just 2.5 miles to discover the cultural delights of Park Avenue in downtown Winter Park. The existing 1940's home is still bursting with charm and potential. From the moment you arrive, the circular paver driveway and inviting front porch set the tone for a home that balances warmth and functionality. The main residence offers 2 bedrooms and 2 bathrooms across 1,500+ square feet, complemented by a detached 1-bedroom, 1-bath guest cottage. Ideal for extended stays, a private office, hobby space, or flexible living arrangements, the detached cottage presents endless possibilities, with enough space available for creative modifications to suit your needs. A paver 2-car parking pad off the circular drive allows room for temporary or long-term guests, with the added convenience of private entry to the detached dwelling via a paved walkway through the side gate. The main home is well-laid-out, with multiple living & dining spaces to make everyday living and entertaining a breeze, all anchored by hardwood flooring throughout. A spacious, paver side patio and large rear deck offer separate, gated outdoor living areas for versatility and enjoyment, while the rear deck overlooks a private, fenced-in backyard just waiting to be transformed into the perfect Florida oasis. If you are looking to land just a few minutes from downtown Orlando and downtown Winter Park, with easy Access to I-4…this is the location for you!
Listing Agent: Marystuart Day (407-620-8683)
7532 AZUREBROOK CT, WINTER PARK, FL 32792
$410,00048 Days on yellowkey MLS ID: O6406380
0 Days Off yellowkey (back on 5/18/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1402 Built: 1979 Tax: $4,889 (2025)Community: Laurel SpgsSingle Family
Taxes:$4,889
Elementary School: Aloma Elem
Remarks: Under contract-accepting backup offers. Located on a quiet cul-de-sac with NO HOA, this adorable Winter Park home sits on an oversized lot with an incredible backyard and endless room for entertaining, relaxing, or play. With a mid-century modern feel and charming curb appeal, this 3-bedroom, 2-bath home is full of character and functionality. As you enter through the foyer, you’re welcomed by an oversized living room to the left, complete with a cute flex space perfect for a home office, reading nook, or play area. The updated kitchen sits at the center of the home and features quartz countertops, bar seating, and views overlooking the dining room, creating a seamless flow for everyday living and entertaining. Laminate flooring runs throughout all main living areas and bedrooms for a clean and modern look. Down the hallway, you’ll find all three bedrooms and two bathrooms, including the spacious primary suite with a large closet and an updated ensuite bathroom featuring a brand-new vanity and stylish paneling details. The dining room and flex area both lead out to the screened-in patio, giving you the perfect indoor-outdoor setup. Step outside to the true showstopper — a massive backyard with endless possibilities, a fire pit area, and plenty of room for activities, gatherings, pets, or even future additions. (zoned R-1A) Additional highlights include an extra-long driveway with space for up to 6 cars plus a 2-car garage. A rare find in Winter Park!
Listing Agent: Christina Frucci (321-303-6881)
346 S RANGER BLVD, WINTER PARK, FL 32792
$475,000284 Days on yellowkey MLS ID: S5134662
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1592 Built: 1965 Tax: $5,339 (2024)Community: Winter Park PinesSingle Family
Taxes:$5,339
Remarks: PRIME LOCATION! Beautiful 3 Bedroom 2 Bathroom home is located in sought after Winter Park Pines with NO HOA and NO CDD. It is situated on a Corner Lot (0.22 Acre) and is a super short distance to the High Rated schools in Winter Park. The interior is extremely well kept with engineered wood floors, crown molding, and a beautiful glass entry door. There is a captivating white-washed stone fireplace and built in shelving for an elegant look in the Family Room. The kitchen has stainless steel appliances, wood cabinets with under cabinet lighting, and bar top seating. Primary Bedroom has a walk-in closet and a glass door shower with tile walls and built-in niches. The Primary bathroom has private access to the screened patio (Florida Room) and spacious backyard. The gated fence opens extra wide for boat, RV or your trailer entry. This entry is very convenient to back any trailer size. For outdoor activities, you just step out of the house and go on a Cady Way Trail for biking, skating, and walking activities. For tennis lovers there are very well kept tennis courts where sport enthusiasts practice their skills in pickleball. Right next to the tennis courts is a playground that offers cozy shaded areas with slopes, swings, and climbing walls. Publix, Costco, Walmart and the post office are all located nearby. For evening promenade the downtown Winter Park, located just a few miles away, offers unique restaurants, cozy coffee shops and bars. To see this amazing 3 bedroom home for sale in Winter Park, call today and schedule a showing! NOTE: Roof - July 2023. HVAC - 2015. No HOA, NO CDD.
Listing is courtesy of: IMPERIAL REALTY OF FLORIDA INC (407-346-4746)
Listing Agent: Tanya Vyushkina (407-346-4746)
3054 BLUEBROOK DR, WINTER PARK, FL 32792
$410,00074 Days on yellowkey MLS ID: O6398450
REDUCED by $17,500 (4.1%) on 05/15/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1939 Built: 1973 Tax: $6,422 (2025)Community: Laurel SpgsSingle Family
Taxes:$6,422
Remarks: Just Reduced the Price! "Open the Doors to Your Dreams" of owning an Affordable Home with a pool in Winter Park. The home features a Spacious Kitchen with Upgraded Cabinets, and stone countertops; Primary bedroom suite is amazing. You will love the layout and upgraded primary bathroom; Beautiful Porcelain tile flooring throughout the home; Large family room with fireplace; Large screened back porch/LANAI. And here is an inground pool in the back yard. You will enjoy entertaining in this home featuring a gourmet kitchen with granite countertops, and stainless steel appliances. This property may qualify for Seller Financing (Vendee). If property was built prior to 1978, Lead Based Paint Potentially Exists. Come tour this home today. We expect this one not to be on the market long at this REDUCED price.
Listing is courtesy of: WEATHERSPOON REALTY INC (407-878-4468)
Listing Agent: Eugene Weatherspoon (407-878-4468)
423 OLOLU DR, WINTER PARK, FL 32789
$549,000168 Days on yellowkey MLS ID: O6369976
REDUCED by $40,000 (6.8%) on 05/14/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1920 Built: 1981 Tax: $4,030 (2024)Community: Killarney CircleSingle Family
Taxes:$4,030
Elementary School: Killarney Elem
High School: Edgewater High
Middle School: College Park Middle
Remarks: PRICE IMPROVEMENT! Welcome to this beautifully remodeled two story home in one of Winter Park’s most desirable upscale neighborhoods, offering timeless charm, modern upgrades, and no HOA restrictions. Completely renovated in 2019, this property features a newer roof, windows, A/C system, electrical, plumbing, driveway, and a fully fenced yard with a private entry gate, along with fresh exterior & interior repaint completed in 2025. Inside, you will find bright, open living spaces and a modern kitchen designed for both everyday living and entertaining. Upstairs, a spacious family room opens to a covered balcony with serene lake views, creating an ideal space to relax or entertain. The flexible layout also allows for two separate living areas, making it well suited for multi-generational living or rental income. Step outside to enjoy the expansive gated yard with plenty of room for gatherings along with ample parking. Conveniently located just minutes from shopping, dining, Downtown Orlando, Downtown Winter Park, Full Sail University, and Rollins College, this home offers an exceptional location. The seller is offering 1% closing cost Buyer credit with a full price offer. Do not miss this rare opportunity to own a beautifully updated home with endless potential in a highly desirable location. Contact us today to schedule your private showing!
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Jill Healey (407-797-1420)
517 ROUGHBEARD RD, WINTER PARK, FL 32792
$565,00072 Days on yellowkey MLS ID: O6399029
1 Days Off yellowkey (back on 5/2/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1873 Built: 1971 Tax: $4,323 (2025)Community: Winter Park Pines Unit 17Single Family
Taxes:$4,323
Remarks: Under contract-accepting backup offers. Welcome home to the Winter Park Pines where the trees line the streets and the mailman delivers to your door. This beautifully maintained 3-bedroom, 2-bathroom home offering 1,873 square feet of comfortable living in the highly desirable and serene Winter Park Pines community. This light-filled residence features a thoughtfully designed split floor plan with high ceilings, fresh interior paint (2026), skylights, and laminate and tile flooring throughout, creating a bright and inviting atmosphere from the moment you enter. The open living and dining areas are anchored by a charming wood-burning brick fireplace, while crown molding, ceiling fans, and French doors add both style and functionality throughout the home. The well-appointed kitchen includes white and gray cabinetry, stainless steel appliances, and a convenient pantry closet, perfect for both everyday living and entertaining. It flows seamlessly into the main living areas, making it easy to gather with family and friends. The spacious primary suite offers a private retreat, thoughtfully separated from the secondary bedrooms, and features a walk-in closet with custom built-ins, ceiling fan, and French doors leading to the expansive and shaded backyard. The renovated en-suite bathroom showcases double vanities and a beautifully tiled shower with frameless glass enclosure. The secondary bedrooms are well-sized and versatile, with easy access to the renovated hall bathroom featuring a granite double vanity, navy cabinetry, and direct access to the backyard, ideal for indoor-outdoor living. Step outside to enjoy a fully fenced, landscaped backyard situated on a generous .22-acre lot. The expansive patio with terracotta tile flooring provides the perfect space for outdoor dining, entertaining, or simply relaxing in a private setting. Additional highlights include a two-car garage and a Ring home security and surveillance system for added peace of mind. Located just minutes from top-rated Winter Park schools, the Cady Way Trail, Winter Park Pines Golf Course, Advent Health Winter Park campus, Crosby Wellness Center and a variety of shopping and dining options, this home offers both tranquility and convenience. Residents also enjoy access to nearby community amenities including a pool, playground, beach volley ball courts and tennis/pickleball courts. With close proximity to major roadways, downtown Winter Park, and Orlando International Airport, this property truly combines comfort, location, and lifestyle. Don’t miss the opportunity to make this exceptional home yours in one of Winter Park’s most sought-after neighborhoods. Roof 2020, HVAC 2022, Plumbing 2014, Water Heater 2021.
Listing Agent: Amy Turner (407-803-3885)
5331 OAK CT, WINTER PARK, FL 32792
$460,000344 Days on yellowkey MLS ID: S5130868
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1263 Built: 1976 Tax: $2,311 (2024)Community: Wrenwood Heights Unit 2Spa: NoSingle Family
Taxes:$2,311
Remarks: Welcome to Wrenwood Heights Community!! Very well Maintain Pool Home on CUL-DE-SAC LOT!! Great community with no HOA. House located on spacious large lot 0.31 Acre. House features Open Concept with 3 bedroom and 2 bathroom! New Roff 2024. Pool was resurfaced in 2025. Fully Fenced Backyard with upgraded Paver patio and mature landscaping and Fruit trees. Community located in Winter Park close to parks, shopping, dining and main highways. Seminole County schools! Call today to schedule your private showing!
Listing Agent: Nataliya Voroshylo Hylton (407-284-7247)
1354 INDIANA AVE, WINTER PARK, FL 32789
$589,900112 Days on yellowkey MLS ID: O6387500
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1269 Built: 1947 Tax: $5,352 (2024)Community: Metzingers AddSingle Family
Taxes:$5,352
Remarks: One or more photo(s) has been virtually staged. Fabulous location in Winter Park! Completely remodeled from top to bottom this stunning home blends modern design with everyday comfort in a highly desirable Winter Park location. Thoughtfully updated with stylish and contemporary finishes throughout this home offers a bright and open feel that’s perfect for today’s lifestyle. The beautifully renovated interior features a modern kitchen, quartz countertops, soft-close shaker cabinets overlooking the dining room & family room. The updated bathrooms and fresh finishes throughout create a move-in ready home that feels brand new! The spacious layout flows seamlessly into the outdoor living area where you’ll find a large fenced-in backyard with a pavered patio and a cozy fireplace perfect for entertaining, relaxing or enjoying Florida evenings. Located just minutes from shopping, dining, parks, and top Winter Park amenities this property is an excellent opportunity for first-time homebuyers or investors looking for a turnkey home in a prime location. A rare opportunity to own a fully updated home with modern style and a spacious backyard in the heart of Winter Park!
Listing Agent: Ellen Bessette (407-496-0076)
632 COUNTRY CLUB DR, WINTER PARK, FL 32789
$1,050,000607 Days on yellowkey MLS ID: O6250417
0 Days Off yellowkey (back on 9/29/2025)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2342 Built: 1952 Tax: $4,638 (2023)Community: Lords SubSpa: NoSingle Family
Taxes:$4,638
Tax Year: 2023
Remarks: Under contract-accepting backup offers. Experience lakeside living in Winter Park, FL with this custom LAKEFRONT PROPERTY on the shores of Lake Killarney, a 234 acre PRIVATE LAKE. There are a limited number of lakefront properties within the City, especially on skiable lakes, so this home presents a unique opportunity. Boasting an EXPANSIVE DOCK, one that’s grander than current building standards allow (but is grandfathered in), this backyard provides an ideal place to launch your water adventures, soak up scenic sunsets, and travel by lake to Hillstone for a meal. The CUSTOM POOL is waiting to be enjoyed! It features a custom waterfall, grotto, built-in seating/table and adjacent koi pond, all with a lake view. Recent updates to the home include: shingled roof (2018), DOUBLE PANE WINDOWS (2015), and HVAC (2016). Travertine and tile floors cover the entire home, there is no carpet. The back family room has multiple French doors and offers an expansive view of the lake. Fireplaces are featured in both the office and living room. The convenience of 632 Country Club is unmatched. It is approximately .6 miles from grocery shopping like Whole Foods and Publix or the Winter Park Village - a vast outdoor mall featuring a 20-screen Regal Cinema, Ruth's Chris Steakhouse and Bar Italia, to name a few. For everyday errands like HomeGoods, or workouts at LA Fitness, there is an even closer shopping plaza. An Interstate 4 (I-4) onramp is approximately 2 miles away. Winter Park is bursting with Old Florida charm and was named #38 historic world destinations in 2008 by National Geographic Magazine. At its heart is Park Avenue, famed for its cobblestoned and tree-lined streets with over 140 boutiques, museums, a train station, and world-class dining. 632 Country Club is approximately 1.5 miles from luxurious Park Avenue and 5 miles from downtown Orlando.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)
Listing Agent: Kristin Duncan (407-274-5911)
2020 COCOS CT, WINTER PARK, FL 32792
$458,990104 Days on yellowkey MLS ID: O6389901
1 Days Off yellowkey (back on 4/24/2026)
REDUCED by $1,000 (0.2%) on 04/17/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1715 Built: 1966 Tax: $1,410 (2024)Community: Eastbrook Sub Unit 8Spa: NoSingle Family
Taxes:$1,410
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Beautifully renovated pool home in the highly desirable Eastbrook community of Winter Park, featuring major recent upgrades including a new AC system, windows, doors, and flooring throughout the home. This move-in ready 3-bedroom, 2-bath residence sits on an oversized 0.30-acre corner lot in a quiet cul-de-sac with no HOA. The home offers a bright open-concept layout with abundant natural light and a seamless flow between the living, dining, and kitchen areas—ideal for both everyday living and entertaining. The updated kitchen features modern cabinetry, stainless steel appliances, and generous counter space. Both bathrooms have been tastefully renovated, and the spacious bedrooms provide comfort and flexibility. Step outside to a private backyard with a sparkling pool and plenty of outdoor space perfect for relaxing or hosting gatherings. Additional highlights include a 1-car garage, roof replaced in 2016, updated electrical, and a newer water heater (2021). Located within the top-rated Seminole County school district and just minutes from Park Avenue, Rollins College, shopping, dining, museums, and Winter Park Hospital. A fantastic opportunity to own a beautifully updated home in one of Central Florida’s most desirable locations.
Listing is courtesy of: SERHANT (786-296-8626)
Listing Agent: Julimar Barreiro Pastrana (407-590-8604)
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