Location: Winter Park
Do Not Show Listings
1605 PURITAN AVE, WINTER PARK, FL 32792
$389,00043 Days on yellowkey MLS ID: O6417098
REDUCED by $10,000 (2.5%) on 07/27/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1285 Built: 1963 Tax: $3,605 (2025)Community: Eastbrook Sub Unit 06 2Nd RepSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,605
Elementary School: Eastbrook Elementary
High School: Lake Howell High
Tax Year: 2025
Middle School: Tuskawilla Middle
Remarks: SELLER FINANCING. Stunning 3-bedroom, 2-bath remodeled home with no HOA, ideally located on the border of Winter Park and Orlando. This move-in-ready property features a new roof installed in July 2025, an updated kitchen with beautiful granite countertops and brand-new appliances. Enjoy the perfect combination of comfort, style, and convenience with easy access to shopping, dining, schools, and major roadways. Don't miss this one! Schedule your private showing right away!
Listing is courtesy of: CENTURY 21 CARIOTI (407-573-2121)
Listing Agent: Angelica Tomlinson Llc (407-222-8676)
1351 ONECO AVE, WINTER PARK, FL 32789
$1,150,00014 Days on yellowkey MLS ID: O6425827
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2474 Built: 1951 Tax: $9,725 (2025)Community: Lake Knowles Terrace 2Nd AddSpa: NoSingle Family
Taxes:$9,725
Elementary School: Lakemont Elem
High School: Winter Park High
Middle School: Maitland Middle
Remarks: Located on one of Winter Park's picturesque brick streets in the highly desirable “Tree Streets”, this beautifully updated home offers incredible curb appeal with a circular driveway, charming front porch with brick flooring, and mature landscaping. Inside, a spacious foyer with soaring ceilings welcomes you, while engineered hardwood flooring runs throughout the main living areas. The recently renovated kitchen is the heart of the home, featuring quartz countertops, custom oak cabinetry with gold hardware, a center island with seating, stylish backsplash, and stainless steel appliances, including a gas range. The kitchen opens to the spacious dining room and inviting family room with built-ins, high ceilings, and French doors that fill the space with natural light. One of the home's most unique features is its thoughtfully designed layout. The original 1951 portion of the home offers two bedrooms, including the original primary suite with a large walk-in closet and private bath, plus a beautifully renovated hall bathroom. An addition completed in the early 2000s created an impressive owner's retreat on the opposite side of the home, complete with vaulted ceilings, French doors to the backyard, an oversized walk-in closet with custom organization, and a spacious bathroom with double vanities, soaking tub, separate shower, and private water closet. A fourth bedroom, tucked away in its own wing off the dining room, features built-ins, a large walk-in closet, and is conveniently located near the indoor laundry room. Situated on a generous .24-acre lot, the backyard offers plenty of room to add a pool while still leaving space to enjoy the yard. A long driveway leads to the rear one-car carport and an oversized storage room. Major updates include a 2020 roof and 2021 AC. All of this is just minutes from Park Avenue's renowned shopping, dining, and events, with easy access to top-rated Winter Park schools, parks, and everything that makes this neighborhood one of Central Florida's most sought-after places to call home.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Maria Van Warner (407-256-8066)
2041 JEWELL AVE, WINTER PARK, FL 32789
$439,90031 Days on yellowkey MLS ID: O6420660
REDUCED by $30,100 (6.4%) on 07/27/2026
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1508 Built: 1947 Tax: $999 (2025)Community: PinesSingle Family
Taxes:$999
Elementary School: None
High School: None
Middle School: None
Remarks: Seller is highly motivated. Competitively priced for a quick sale. Don't miss your opportunity to own this beautiful home! First time on the market in over 60 years! Filled with decades of cherished family memories, this beloved home is ready for its next chapter. Located in the highly desirable Winter Park 32789 ZIP code, 2041 Jewell Avenue offers an unbeatable location just minutes from Dubsdread Golf Course, College Park, and downtown Winter Park, with quick access to I-4, making commuting throughout Central Florida a breeze. Lovingly maintained and thoughtfully updated over the years, the home features a 2024 roof, central air conditioning, and a large, wheelchair-accessible walk-in shower, providing enhanced comfort and accessibility. The spacious, fully fenced backyard offers plenty of room to relax, entertain, garden, or play. Situated on a quiet dead-end street, you'll enjoy minimal traffic and a peaceful neighborhood setting. The original fourth bedroom has been converted into a generous laundry room, adding convenience and extra storage while offering flexibility for future customization if desired. Whether you're looking to move right in, renovate, or create your dream home in one of Central Florida's most sought-after neighborhoods, this property presents an exceptional opportunity. Now it's your turn to create a lifetime of memories and make this treasured home your own.
Listing is courtesy of: IAD REAL ESTATE (407-720-0020)
Listing Agent: Martha Coronel (321-438-2737)
722 S RANGER BLVD, WINTER PARK, FL 32792
$799,90028 Days on yellowkey MLS ID: O6421873
REDUCED by $25,100 (3.0%) on 07/27/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2164 Built: 1967 Tax: $455 (2025)Community: Winter Park PinesSpa: NoSingle Family
Taxes:$455
Elementary School: Aloma Elem
Middle School: Glenridge Middle
Remarks: Impeccably Renovated Turn-Key Oasis with a Resort-Style Backyard! No HOA with yard large enough for possible ADU. Welcome home to this meticulously updated 4-bedroom, 3-bathroom residence where true pride of ownership shines through every detail. Absolutely turn-key and loaded with premium updates throughout, such as new electrical panel, newer water heater, new pool pavers, upgraded engineered floors throughout & much more! This home offers the perfect blend of modern luxury and effortless entertaining.The heart of the home seamlessly connects to the outdoors with a brilliant kitchen pass-through window, serving an enormous covered patio. Step into your own private, tranquil backyard oasis featuring a freshly resurfaced pool surrounded by stunning new pavers & large Perolga. Whether you are hosting a summer barbecue or rinsing off in your convenient outdoor shower after a swim, this backyard is built for Florida living at its finest. Property is zoned for highly rated schools with convenient location just moments away from Cady Way Park & trails, Rollins, UCF, & Full Sail Colleges, just 4 miles from vibrant dining(Park Ave) & premier shopping.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Karen Gore (407-810-0871)
1741 MIZELL AVE, WINTER PARK, FL 32789
$998,00069 Days on yellowkey MLS ID: O6410059
REDUCED by $52,000 (5.0%) on 07/27/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2015 Built: 1982 Tax: $11,682 (2025)Community: Lake Monte SubSingle Family
Taxes:$11,682
Elementary School: Brookshire Elem
Remarks: Culture, Convenience, Community! Discover refined living in the heart of Winter Park, where timeless luxury meets an unmatched lifestyle. This beautifully designed single-story residence offers three spacious bedrooms, a private office, two elegantly appointed baths and over 2,000 square feet of living space complete with a two-car garage and no HOA. Thoughtfully curated with sleek tile flooring throughout and no carpeting, the home exudes both style and comfort. The well-equipped kitchen features granite countertops, a pantry, and a charming breakfast area, flowing effortlessly into the expansive family and dining rooms. French doors open to a generous screened lanai and a private fenced backyard, creating the perfect setting for seamless indoor-outdoor entertaining. Designed with a desirable split floor plan, the luxurious primary suite offers private backyard access, dual walk-in closets plus an additional storage closet and a private bath with a spacious walk-in shower. Two additional guest bedrooms share a beautifully appointed bath with shower/tub, while one bedroom enjoys direct access to a dedicated office space, ideal for guests or working from home. Winter Park is celebrated for its distinctive blend of arts and culture, charming sidewalk cafés, acclaimed museums, upscale accessible neighborhoods, scenic lakes, outdoor recreation and year-round festivals. Surrounded by top-rated schools and picturesque tree-lined streets, this exceptional location offers premier conveniences. Near AdventHealth, Cady Way Trail and recreational parks, YMCA of Central Florida, public golf courses, Rollins College, Full Sail University and UCF. Whether you're seeking outdoor adventure, cultural enrichment, or everyday convenience, this location delivers it all. Schedule your private showing today and discover the best of Winter Park living. Roof - 2018, AC - 2015.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Farah Novin (407-234-0501)
724 MONMOUTH WAY, WINTER PARK, FL 32792
$849,94919 Days on yellowkey MLS ID: O6424409
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2832 Built: 1969 Tax: $9,215 (2025)Community: Winter Park PinesSingle Family
Taxes:$9,215
Remarks: LIGHTING FAST RESPONSE - FULLY RENOVATED 5-BEDROOM, 4-BATH WINTER PARK ESTATE Welcome to 724 Monmouth Way, a beautifully reimagined five-bedroom, four-bath estate designed for comfortable family living, elegant entertaining, and everyday luxury. Renovated in 2026, this spacious home features thoughtfully separated bedroom wings, impressive living areas, abundant natural light, and designer finishes throughout. The expansive 13-by-22-foot primary suite offers enough space for a private sitting area, reading retreat, or lounge within the bedroom. The luxurious primary bathroom features a double vanity, an oversized shower with dual showerheads, a heated smart toilet, and a six-foot freestanding soaking tub positioned beneath a built-in skylight. Marble fluted accent walls surrounding the tub and shower create a dramatic, spa-like atmosphere. A generous 7-by-8-foot walk-in closet provides abundant storage. At the heart of the home is a newly designed, chef-inspired kitchen featuring a striking 9-by-5-foot double-waterfall island, extensive cabinetry, exceptional storage, a custom range hood surround, and an elegant cabinet column that gives the kitchen a truly distinctive designer look. Two large skylights above the kitchen and adjoining casual dining area fill the space with natural light, creating a bright, open, and inviting atmosphere throughout the day. The adjoining butler’s pantry functions as a second kitchen and includes its own sink and faucet, full-size refrigerator space, extensive cabinetry, and additional countertop space. Prepare meals, store small appliances, and keep entertaining messes neatly tucked away from the main kitchen. A guest bedroom located near the primary suite includes its own private ensuite bathroom. This flexible left-wing space is ideal for overnight guests, a nursery, private office, fitness room, or multigenerational living arrangement. On the opposite side of the home, the right bedroom wing offers added privacy and separation from the primary suite. This hallway includes three additional spacious bedrooms, a full bathroom, and a convenient half bathroom. The large formal living room is filled with natural light from its front-facing windows. A separate 22-foot family room creates an impressive gathering space and features a dramatic 10-foot linear fireplace, making it the perfect setting for holidays, celebrations, movie nights, and everyday relaxation. Outside, the large, thoughtfully designed backyard features newly installed Zoysia grass, a private putting green, and naturally shaded areas perfect for relaxing, entertaining, or enjoying the Florida lifestyle. Major improvements include a new roof, electrical system, plumbing, and water heater completed in 2026, along with an HVAC system installed in 2019. This exceptional Winter Park home combines generous living space, modern luxury, flexible accommodations, dramatic natural light, and extensive renovations in one remarkable property.
Listing is courtesy of: CENTRAL TOWER PROPERTIES (321-948-3144)
Listing Agent: Cardiff Howell (321-948-3144)
7450 WYNNEWOOD SQ #189, WINTER PARK, FL 32792
$185,00015 Days on yellowkey MLS ID: O6425486
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1031 Built: 1984Monthly Fee: $450 Tax: $567 (2025)Community: Hidden Oaks Condo Ph 10Condo
Taxes:$567
Remarks: This charming 2-bedroom, 2.5-bathroom townhome style condo offers the perfect blend of comfort and convenience. Enjoy the peace of mind that comes with a new AC (2025), a new roof (2021), newer water heater (2019) and new refrigerator and dishwasher ensuring your home is both energy-efficient and well-maintained. The entire first floor features ceramic tile, while the upstairs boasts beautiful laminate wood flooring—no carpet here! Both bedrooms are located upstairs, each with its own ensuite bathroom and additional storage above the mirrors. Downstairs, you'll find ample space for entertaining or simply relaxing, enhanced by the convenience of a wet bar. Located just minutes from UCF and Full Sail University, this condo is perfect for anyone looking to enjoy the vibrant local community without the long commute! With shopping, dining, and recreational activities nearby, you'll have everything you need right at your fingertips. Don’t miss out on this fantastic opportunity—schedule a showing today!
Listing is courtesy of: GLOBAL PROPERTIES SALES & MGMT (407-675-6999)
Listing Agent: Kim King (407-448-6774)
2487 HARBOUR WAY, WINTER PARK, FL 32792
$290,00015 Days on yellowkey MLS ID: O6422155
REDUCED by $10,000 (3.3%) on 07/27/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1803 Built: 1978Monthly Fee: $95 Tax: $5,059 (2025)Community: Windward Square Sec 1Townhouse
Taxes:$5,059
High School: Hagerty High
Middle School: Chiles Middle
Remarks: Welcome to 2487 Harbour Way, a spacious single-story townhome offering 3 bedrooms, 3 full bathrooms, and 1,803 square feet of comfortable living space. The practical layout features inviting living and dining areas, a well-equipped kitchen, central air, and a walk-in closet. Outside, garden space, lighting, and sidewalks add to the home's appeal. Enjoy a low-maintenance lifestyle in Windward Square, where residents have access to a community pool and playground, with the pool included in the low monthly HOA fee. Conveniently located near schools, parks, shopping, dining, and everyday essentials, this Winter Park property offers space, convenience, and community amenities in one appealing package. Schedule your private showing today!
Listing is courtesy of: LOKATION (954-545-5583)
Listing Agent: Joel Garay (203-522-2231)
641 NORTHWOOD CIRCLE, WINTER PARK, FL 32789
$1,669,00059 Days on yellowkey MLS ID: O6412554
REDUCED by $56,000 (3.2%) on 07/24/2026
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2756 Built: 2023 Tax: $18,393 (2025)Community: Winter Park OasisSingle Family
Taxes:$18,393
Remarks: Tucked away on a peaceful cut-de-sac in the heart of Winter Park, this striking modern residence offers a rare blend of privacy, walkability and refined design. A private courtyard entrance sets the tone, creating a serene arrival and sense of retreat from the moment you step onto the property. Inside, polished concrete floors and an open, light-filled layout define the home's contemporary aesthetic, with clean lines and seamless flow designed for everyday living and effortless entertaining. Step outside to your own private oasis- complete with a pool and tranquil outdoor spaces- perfect for enjoying Florida living year-round. The home's prime location allows for an exceptional lifestyle- just a short stroll to Park Avenue's renowned shops and dining and an even shorter stroll to the golf course. Offering a unique combination of modern design and in-town convenience, this is Winter Park living at its most elevated.
Listing Agent: Sandra Cuba (305-878-0167)
1120 WISCONSIN AVE, WINTER PARK, FL 32789
$1,084,00065 Days on yellowkey MLS ID: O6406800
REDUCED by $11,000 (1.0%) on 07/27/2026
Bed: 3 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2213 Built: 2021 Tax: $10,451 (2025)Community: Henkel AddSingle Family
Taxes:$10,451
Elementary School: Killarney Elem
High School: Edgewater High
Middle School: College Park Middle
Remarks: Curated with intention and finished without compromise, 1120 Wisconsin Avenue is a rare opportunity to own a bespoke Winter Park residence where elevated design meets effortless everyday living. Every detail of this 2,213-square-foot, three-bedroom, three-and-a-half-bath home has been thoughtfully considered — from the custom Pella® multi-point entry door that welcomes you into a light-filled, open-concept gathering room, to the chef's kitchen anchored by a dramatic waterfall island and ZLINE commercial-style gas range with soft-close cabinetry and curated high-end appliances throughout. A private courtyard entry sets a serene tone before you've even stepped inside. The seamless indoor-outdoor connection continues through Pella® wood-clad sliding glass doors to a covered BBQ kitchen lanai — your own tranquil outdoor retreat. The primary suite is a true sanctuary: a generous walk-in closet, a sitting area, linen storage, and a spa-caliber bathroom with a double-sink vanity and oversized walk-in shower. Upstairs, two spacious en-suite bedrooms and a versatile loft with built-in storage offer flexibility for guests, family, or a refined home office. Finished with stunning hardwood floors, soaring ceilings, custom window treatments, spray foam insulation, and dual-zone climate control, this home is as quietly practical as it is undeniably beautiful. Whether you're entertaining or simply unwinding, 1120 Wisconsin Avenue offers the ease and elegance of a true lock-and-leave lifestyle in one of Winter Park's most sought-after neighborhoods.
Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)
Listing Agent: Kelly Price (407-645-4321)
7336 FOREST HILL CT #240, WINTER PARK, FL 32792
$163,500153 Days on yellowkey MLS ID: O6386461
0 Days Off yellowkey (back on 7/26/2026)
REDUCED by $6,400 (3.8%) on 07/23/2026
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 990 Built: 1984Monthly Fee: $450 Tax: $2,899 (2025)Community: Hidden Oaks Condo Ph 12Condo
Taxes:$2,899
Remarks: Under contract-accepting backup offers. Updated Winter Park Townhome!! If you are looking for LOCATION this is the property for you. This well maintained END unit is move in ready: two-story 2 Bedrooms 1.5 Bath townhome style condo with two designated parking spaces. Upon entering you are greeted with a large living and dining room space. Tiled floors, tons of light, neutral colors, wet bar area are a few of the amazing qualities of this space. Just off the dining room you will find the kitchen and eat in kitchen area. Updated cabinetry, quartz counters, stainless steel appliances and tons of storage. The eat in kitchen space is highlighted with a decorative wall and sliders leading to your fully fenced private backyard space. Upstairs you will find hardwood flooring, two bedrooms and master bathroom with double vanity set and brown glass sink top in dark coffee. Hidden Oaks community features on-site security, community pool & fenced playground area. Near Full Sail, UCF, Valencia & Rollins College, with easy access to shopping, Winter Park schools, Medical Facilities, Downtown Orlando, Downtown Winter Park, FL-408, FL-417 and the airport. This wonderful unit has it all...the only thing missing is YOU!
Listing Agent: Steven Looper (321-662-3582)
1807 HAMMERLIN AVE #G, WINTER PARK, FL 32789
$499,000135 Days on yellowkey MLS ID: O6391277
REDUCED by $16,000 (3.1%) on 07/26/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1818 Built: 2006 Tax: $6,197 (2025)Community: Terrazo Del SolCondo
Taxes:$6,197
Elementary School: Audubon Park K8
Middle School: Audubon Park K-8
Remarks: Virtually Staged. **Price Improvement** Welcome home to this beautifully updated two-story end-unit, ideally located just steps from Michelin-star dining, local boutiques, and the vibrant East End Market. On weekends, enjoy leisurely strolls to the area’s popular farmers markets and neighborhood events. Situated in the heart of Winter Park, this residence offers the perfect blend of lifestyle, convenience, and charm in one of Orlando’s most sought-after communities. Designed for both everyday comfort and effortless entertaining, the first floor features an open-concept kitchen and living area filled with abundant natural light, along with a convenient half bath—ideal for hosting guests. Upstairs, the spacious primary suite boasts a private ensuite bathroom, walk-in closet, and a newly refinished balcony—perfect for morning coffee or evening cocktails. Two additional bedrooms provide generous space and share access to a second balcony, creating a seamless indoor-outdoor living experience. Recent upgrades include a new dishwasher and smart refrigerator (2022), new water heater (2025), refinished front balcony (2025), new roof, and new carpet upstairs (2026). Updated light fixtures and primary bedroom flooring within the last five years add a modern touch throughout. The $400 monthly HOA fee includes landscaping and insurance, offering low-maintenance living and added peace of mind. Zoned for some of Orlando’s top-rated schools and walking distance from the new Audubon Park K-8 School, this home presents a rare opportunity to enjoy the very best of Winter Park living. Don’t miss your chance to call this exceptional property home.
Listing is courtesy of: ALL REAL ESTATE & INVESTMENTS (407-917-8206)
Listing Agent: Courtney Dietch (407-952-3779)
1611 CHESTNUT AVE, WINTER PARK, FL 32789
$1,040,00091 Days on yellowkey MLS ID: O6402502
REDUCED by $30,000 (2.8%) on 07/10/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2916 Built: 1973 Tax: $3,590 (2025)Community: Lake Knowles TerraceSingle Family
Taxes:$3,590
Remarks: NEW PRICE!! DON'T MISS THIS OPPORTUNITY! Situated on arguably the finest brick street in Winter Park, beneath a canopy of live oaks, this fully renovated 4-bedroom, 4-bath home delivers the rarest combination: the soul of an established neighborhood, unique charm and character, and the bones of new construction. Gutted to the studs and rebuilt with intention, every major system is new — every detail of this rennovation was completed with quality and permanence in mind. With elevated finishes, like designer tile and quartz countertops as well as floors and beautifully reimagined kitchen and baths. A second-floor addition adds a sprawling 21 x 24 foot private primary suite and home office, one of the many reasons this an ideal setup for MULTIGENERATIONAL families and those who work from home. A welcoming fireplace, lush mature landscaping, butler's pantry, numerous built ins, custom tile work, and an address minutes from Park Avenue make this one of Winter Park's most compelling offerings. Come imagine the possibilities.
Listing Agent: Olivia Maxwell (407-222-4440)
2015 SUMMERFIELD RD, WINTER PARK, FL 32792
$1,262,50042 Days on yellowkey MLS ID: O6418198
REDUCED by $12,500 (1.0%) on 07/23/2026
Bed: 4 Bath: 4.0 Gar: 1 Liv Area Sq Ft: 3024 Built: 1957 Tax: $7,243 (2025)Community: Kenilworth Shores Sec 07Single Family
Taxes:$7,243
Remarks: Welcome to one of Winter Park's most impressive move-in-ready homes, where luxury, comfort, and location come together seamlessly. Completely reimagined and renovated, this stunning 4-bedroom, 4-bath residence offers the rare combination of modern construction quality and an established Winter Park location just minutes from Baldwin Park, Park Avenue, Rollins College, and top-rated schools. From the moment you arrive, the circular driveway, modern architecture, and professional landscaping create a memorable first impression. Inside, soaring natural light and oversized porcelain tile floors lead you through an open-concept floor plan designed for both everyday living and entertaining. The heart of the home is an extraordinary chef's kitchen featuring premium Bosch appliances, an oversized quartz island, custom cabinetry, a walk-in pantry, and a stylish wet bar. Whether hosting holiday gatherings or enjoying a quiet morning coffee, this space was designed to bring family together. The private owner's retreat feels like a luxury resort, offering direct pool access, a spa-inspired bathroom, soaking tub, oversized walk-in shower, custom closet, and a private beverage station for added convenience. Step outside and discover what truly sets this property apart. The backyard was designed for Florida living at its finest, featuring a sparkling pool, expansive covered lanai, outdoor dining area, and a fully equipped summer kitchen complete with grill, refrigeration, storage, and sink. It's the perfect setting for family gatherings, weekend entertaining, or relaxing after a long day. A dedicated office, versatile flex room, pool bath, and guest suite provide the flexibility today's buyers demand for work, fitness, hobbies, multigenerational living, or media space. Beyond the home itself, you'll enjoy a lifestyle few locations can match. Walk or bike to nearby parks and trails, spend evenings dining on Park Avenue, explore Baldwin Park's restaurants and shops, and enjoy quick access to Downtown Orlando and Orlando International Airport. With luxury finishes, smart-home upgrades, resort-style outdoor living, and a premier Winter Park address, this is more than a home—it's a lifestyle opportunity rarely available in Kenilworth Shores. Schedule your private showing today and experience the difference for yourself.
Listing is courtesy of: UNITED REAL ESTATE PREFERRED (407-243-8840)
Listing Agent: Courtney Lindsay (206-486-5015)
1421 CHAPMAN CIR, WINTER PARK, FL 32789
$1,450,00048 Days on yellowkey MLS ID: O6415941
REDUCED by $100,000 (6.5%) on 07/11/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3578 Built: 2005Monthly Fee: $268 Tax: $10,592 (2025)Community: Windsong Elizabeths Walk 43/81Single Family
Taxes:$10,592
Remarks: Welcome to 1421 Chapman Circle, an elegant Spanish-Mediterranean home nestled within the highly coveted Windsong community in the heart of Winter Park. From the moment you arrive, the classic barrel tile roof and timeless architectural character set the tone for what awaits inside — a home with enduring style, gracious proportions, and tremendous potential to be personalized for its next chapter. Spanning over 3,500 square feet, this 4-bedroom, 3.5-bath residence offers a formal, well-appointed layout with soaring high ceilings, rich crown molding, and a thoughtful floor plan designed for both comfortable daily living and effortless entertaining. A dedicated first-floor office provides the ideal work-from-home space, while the separate formal dining room adds an air of sophistication perfect for hosting family and friends. The gourmet kitchen is the heart of the home, featuring granite countertops, premium Thermador appliances, and bartop seating — a space equally suited for casual mornings and lively gatherings. The living room opens through French doors to a generous wrap-around screened patio, seamlessly blending indoor and outdoor living in true Florida fashion. The first-floor primary suite is a private retreat, complete with French door access to the patio, a spacious walk-in closet, and a well-appointed en suite bath featuring a double sink vanity, a separate soaking tub, and a walk-in shower. Upstairs, three generously sized guest bedrooms share a hall bath, and a large bonus room and landing offer flexible space for a playroom, media room, or additional lounge area. A large upstairs utility room and additional walk-in storage beneath the stairs ensure that function is never sacrificed. The home is served by two HVAC units, both dated 2017. Beyond the front door, the Windsong community is nothing short of exceptional. Residents enjoy access to two resort-style pools, a splash pad for the little ones, scenic parks, a fishing dock, and coveted chain-of-lakes access complete with use of a community boat — a lifestyle that truly sets Windsong apart. Zoned for A-rated schools and ideally situated just minutes from the vibrant energy of Baldwin Park, Audubon Park, the Mills District, Downtown Orlando, and all that Winter Park has to offer, this address places you at the center of everything. Whether you're drawn to its classic architecture, its unmatched community amenities, or the incredible opportunity to update and truly make it your own, 1421 Chapman Circle is a rare find in one of Central Florida's most beloved neighborhoods.
1707 HARMON AVE, WINTER PARK, FL 32789
$639,00072 Days on yellowkey MLS ID: O6409180
REDUCED by $10,000 (1.5%) on 07/19/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1669 Built: 1927 Tax: $4,658 (2025)Community: LawndaleSingle Family
Taxes:$4,658
Remarks: A timeless blend of historic charm and modern luxury awaits in this beautifully restored 1927 Florida bungalow, nestled in the highly sought-after and peaceful neighborhood of Orwin Manor in Winter Park. Rich in character and thoughtfully updated throughout, this exceptional residence seamlessly combines the elegance of its original architecture with the comfort and sophistication of modern living. Upon entering, you are welcomed by an inviting foyer featuring new tile flooring and refined vertical shiplap detailing, setting the tone for the home’s timeless design. Custom transitions lead into the spacious living room, where original hardwood floors, a cozy fireplace, and smart lighting create a warm and inviting atmosphere ideal for both entertaining and everyday living. The formal dining room comfortably accommodates gatherings of eight and is highlighted by a stunning Serena & Lily chandelier, creating the perfect setting for memorable dinners and celebrations. Just beyond, the fully renovated chef’s kitchen serves as the heart of the home. Updated in 2020, it features elegant Calacatta countertops, an oversized island, premium Samsung appliances, and stylish West Elm lighting. An adjacent eat-in dining space offers a more casual setting and opens directly to the beautifully paved backyard, perfect for outdoor dining and entertaining. The home’s accommodations are equally impressive, including a serene primary suite complete with dual closets and a beautifully appointed bathroom featuring sleek matte finishes. Additional living spaces include a versatile recreation room and a well-appointed guest bedroom, each designed with both comfort and functionality in mind. A private attic provides valuable additional storage space. Every detail of the home has been carefully considered to enhance both aesthetics and practicality, including smart exterior lighting, a durable vinyl privacy fence, low-maintenance landscaping tailored to Florida living, and an updated Carrier HVAC system with a smart thermostat for year-round comfort. Preserving the integrity of the home’s historic character, original woodwork, including baseboards and casings, has been thoughtfully maintained, while curated paint selections and Trex exterior staircases add lasting beauty and durability. Ideally located just minutes from Park Avenue, College Park, and major thoroughfares, this remarkable property offers an exceptional combination of tranquility, convenience, and community. More than just a home, it is a rare opportunity to own a beautifully preserved piece of Winter Park history where timeless charm and contemporary elegance exist in perfect harmony. New roof 2026***
Listing Agent: Nicole Howell (321-217-7918)
950 HANOVER AVE, WINTER PARK, FL 32789
$460,000110 Days on yellowkey MLS ID: O6398273
REDUCED by $10,000 (2.1%) on 06/01/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1606 Built: 1956 Tax: $3,525 (2025)Community: Albert Lee Ridge 1St AddSingle Family
Taxes:$3,525
Remarks: Preferred lender credit available. Welcome home to your peaceful retreat tucked away near the end of a quiet street with views of Lake Wilderness. Completely updated in 2017, move-in ready so you can lock and leave with peace of mind to enjoy the everyday lifestyle of Winter Park and Central Florida this amazing location offers. Full updates made in 2017 include new roof, plumbing, electrical, windows, recessed lighting, a/c unit, and more. Natural sunlight flows throughout the home reflecting off the refinished wood floors creating an inviting and cozy environment. The open kitchen features quartz countertops, glass crafted tile backsplash, custom cabinets, breakfast bar and stainless steel appliances. Feel refreshed and relaxed as you step into the primary suite with barn doors leading into the spa-inspired bathroom, complete with dual vanities and a large walk-in tiled shower. The backyard is fully fenced and the outdoor patio is screened-in and covered. Extra storage space can be used in the outdoor shed or the one car attached garage. No HOA and not in a flood zone. The property’s exceptional location offers close proximity to I-4 East and West, upscale award-winning Winter Park restaurants and boutiques, Winter Park Village, WP9 Golf Course, Park Ave, and the upcoming state-of-the-art Lifetime Fitness center which features over 85,000 SqFt and 5 acres of the best that wellness amenities have to offer. Nearby EV charging stations located within 2 miles away make sustainable living effortless. Rare opportunity to settle into or invest in a peaceful updated retreat located in the highly desirable and vibrant community of Winter Park.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Michael Domi (407-212-8841)
2305 SUN VALLEY CIR, WINTER PARK, FL 32792, WINTER PARK, FL 32792
$279,90028 Days on yellowkey MLS ID: O6421422
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1295 Built: 1985Monthly Fee: $499Community: Cedarwood VillageCondo
Taxes:$0
Remarks: Beautifully renovated 2 bedroom, 2 bathroom condo at 2305 Sun Valley in Winter Park, offering a fresh modern design and thoughtful updates throughout. The fully redesigned kitchen features sleek cabinetry, quartz countertops, GE stainless steel appliances, a marble tile backsplash, abundant storage, recessed lighting, and a clean open feel that connects seamlessly to the main living areas. Wood-look porcelain tile flooring runs throughout the home, creating a cohesive, attractive, and low-maintenance finish. The spacious living area features vaulted ceilings, skylights, updated ceiling fans, and sliding glass doors that fill the space with natural light and lead to a covered screened patio overlooking green space. The primary suite includes an updated double vanity and a beautifully redesigned bathroom with a separate tub and newly installed shower. The second bathroom also offers an updated vanity and clean neutral finishes. Additional highlights include a 2021 AC, 2021 water heater, updated fixtures, generous natural light, and a screened outdoor living space ideal for relaxing and enjoying Florida’s indoor-outdoor lifestyle. This move-in ready Winter Park condo combines modern style, comfort, and everyday functionality. Residents enjoy access to a sparkling community pool, clubhouse, tennis and pickleball, and a pet walk with waste stations. Monthly fees also include roof and exterior building maintenance, exterior pest control, and landscaping, adding convenience and long-term value.The location is hard to beat, just minutes from Park Avenue, UCF, Rollins College, Full Sail University, shopping, dining, entertainment, and nearby medical facilities.
Listing is courtesy of: MARKET CONNECT REALTY LLC (407-250-4708)
Listing Agent: Ryan Barnett (321-312-0545)
1540 FLORENTINO LN, WINTER PARK, FL 32792
$315,00068 Days on yellowkey MLS ID: O6408841
REDUCED by $20,000 (6.0%) on 07/12/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1682 Built: 2004Monthly Fee: $175 Tax: $5,340 (2025)Community: Vistas At Lake HowellTownhouse
Taxes:$5,340
Elementary School: Sterling Park Elementary
Remarks: Come and see your new home in the sought after Vistas at Howell Branch community. This two story townhouse has 3 bedrooms, 2.5 baths, and open first floor, floor plan. Relax in the evening on your screened in porch. The master bedroom has a walk in closet and large master bath. Your washer and dryer are on the second floor centrally located to all the bedrooms. You will find yourself within walking distance of restaurants, grocery stores, and other retail outlets. It's central location puts within minutes of 436 and 417. Schedule your showing today!
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Ashley Fisak (407-848-7975)
311 E MORSE BLVD #1-3, WINTER PARK, FL 32789
$1,895,00083 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
Taxes:$16,493
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 Agent: Megan Cross (407-353-9997)
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