Location: Winter Park
Do Not Show Listings
230 KILLARNEY DR, WINTER PARK, FL 32789
$1,250,00012 Days on yellowkey MLS ID: O6415950
Bed: 4 Bath: 1.0 Liv Area Sq Ft: 1260 Built: 1925 Tax: $5,754 (2025)Community: Killarney EstatesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,754
Elementary School: Killarney Elem
High School: Edgewater High
Tax Year: 2025
Middle School: College Park Middle
Remarks: Virtually Staged. Own a piece of Lake Killarney, a rare opportunity to build your dream water-view estate in the heart of Winter Park. This exceptional homesite offers direct access to private, spring-fed, skiable Lake Killarney, complete with water rights and the ability to build your own private dock. An increasingly rare opportunity in one of Central Florida's most desirable communities. Ideally located just minutes from Park Avenue, Winter Park Village, Rollins College and downtown Orlando, you'll enjoy the perfect balance of lake life, tranquility and accessible convenience. Experience award-winning dining, boutique shopping, entertainment, cultural attractions and everyday conveniences just moments from your future home. Priced to encourage redevelopment, this property is adjacent to 240 Killarney Drive, creating a rare opportunity to purchase one or both parcels. Together, they form an extraordinary double-lot assemblage with expansive views of Lake Killarney and endless possibilities to design a landmark residence. Whether purchased individually or together, opportunities to own on Lake Killarney are exceptionally limited. Build the custom home you've envisioned while enjoying one of Winter Park's most coveted locations from this desirable corner homesite with private lake access and the ability to build your own dock.
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-581-7888)
Listing Agent: Shandy Ortiz (407-427-8619)
240 KILLARNEY DR, WINTER PARK, FL 32789
$1,275,00012 Days on yellowkey MLS ID: O6415977
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1329 Built: 1947 Tax: $6,161 (2025)Community: Killarney EstatesSingle Family
Taxes:$6,161
Remarks: Virtually Staged. Own a piece of Lake Killarney, a rare opportunity to build your dream water-view estate in the heart of Winter Park. This exceptional homesite offers direct access to private, spring-fed, skiable Lake Killarney, complete with water rights and the ability to build your own private dock. An increasingly rare opportunity in one of Central Florida's most desirable communities. Ideally located just minutes from Park Avenue, Winter Park Village, Rollins College and downtown Orlando, you'll enjoy the perfect balance of lake life, tranquility and accessible convenience. Experience award-winning dining, boutique shopping, entertainment, cultural attractions and everyday conveniences just moments from your future home. Priced to encourage redevelopment, this property is adjacent to 230 Killarney Drive, creating a rare opportunity to purchase one or both parcels. Together, they form an extraordinary double-lot assemblage with expansive views of Lake Killarney and endless possibilities to design a landmark residence. Whether purchased individually or together, opportunities to own on Lake Killarney are exceptionally limited. Build the custom home you've envisioned while enjoying one of Winter Park's most coveted locations from this desirable homesite with private lake access and the ability to build your own dock.
3463 ARNEL DR, WINTER PARK, FL 32792
$404,900134 Days on yellowkey MLS ID: O6390301
REDUCED by $5,000 (1.2%) on 07/24/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1770 Built: 1967 Tax: $4,648 (2024)Community: Eastbrook Sub Unit 11Single Family
Taxes:$4,648
Elementary School: Eastbrook Elementary
High School: Lake Howell High
Tax Year: 2024
Middle School: Tuskawilla Middle
Remarks: One or more photo(s) has been virtually staged. Pool Home *No HOA *Paid-Off Solar Panels **Roof (2018) Welcome to this well-maintained 3-bedroom, 2-bathroom home offering approximately 1,770 square feet, a 2-car garage, private pool, Roof (2018), Water Heater (2019), and fully paid-off solar panels for added energy savings. The renovated kitchen features quartz countertops, stainless steel appliances, modern cabinetry, an oversized island with an induction cooktop, and an open layout that flows into the main living areas. The spacious Florida Room is one of the home's highlights, featuring soaring wood ceilings, exposed beams, a built-in serving area, and direct access to the pool. It's a great space to relax, entertain, enjoy your morning coffee, or watch the big game. The primary suite offers a flexible bonus area that can be used as a reading nook, home office, vanity, workout space, or additional storage. The primary bathroom also has direct access to the pool. Step outside and enjoy a backyard that's hard to find in many pool homes. In addition to the private pool, you'll still have green space to enjoy, plus a barbecue connection already in place for outdoor cooking. Whether you're hosting friends, grilling on the weekend, or simply unwinding by the pool after work, this backyard is ready to enjoy. Conveniently located just minutes from Park Avenue, Rollins College, Full Sail University, UCF, shopping, dining, and major highways. Zoned for highly rated Seminole County schools.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)
Listing Agent: Alexa Monasterio Flores (786-915-9294)
722 S RANGER BLVD, WINTER PARK, FL 32792
$799,90027 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
High School: Winter Park High
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
$998,00068 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)
1750 WALNUT AVE, WINTER PARK, FL 32789
$2,195,00019 Days on yellowkey MLS ID: O6422700
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3691 Built: 2019 Tax: $17,303 (2025)Community: Conwill EstatesSingle Family
Taxes:$17,303
Elementary School: Lakemont Elem
Middle School: Maitland Middle
Remarks: Positioned in one of Winter Park's most desirable neighborhoods, this exceptional French Mediterranean residence is just moments from Phelps Park, the Winter Park YMCA, Lakemont Elementary, and Interlachen Country Club. Built by MichaelCharles Homes with interiors by Wolfe-Rizor Interiors, the home pairs timeless architecture with refined contemporary design, abundant natural light, and exceptional craftsmanship. The thoughtfully designed floor plan offers 4 bedrooms, 4 full bathrooms, and 1 half bathroom. The first-floor primary suite features a spa-inspired bathroom and an expansive custom walk-in closet with dedicated his-and-her wardrobe areas. A flexible adjoining room is ideal as a private office, nursery, fitness room, or optional fifth bedroom. On the opposite wing of the home, the private guest suite includes a full bathroom and walk-in closet. The second floor features two additional guest bedrooms, each with access to a full bathroom, along with a spacious loft that serves as the perfect media room, playroom, or secondary living area. At the heart of the home, the chef's kitchen showcases a large center island, custom cabinetry, and premium finishes. Oversized glass doors open to a covered lanai with outdoor dining, grilling space, and a resort-style pool. Framed by mature Japanese maple trees, the backyard offers exceptional privacy and a spacious lawn for recreation or entertaining. Situated on a quiet, oak-lined street, this custom-built home reflects the quality in every detail, presenting a rare opportunity to own an exceptional residence in the heart of Winter Park.
Listing is courtesy of: PALMANO GROUP RE BROKERAGE LLC (321-214-1211)
Listing Agent: Richard Palmano (407-232-5801)
724 MONMOUTH WAY, WINTER PARK, FL 32792
$849,94918 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
$185,00014 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
$290,00014 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
$1,669,00058 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)
1507 GOLFSIDE DR, WINTER PARK, FL 32792
$850,000118 Days on yellowkey MLS ID: O6395355
REDUCED by $49,000 (5.5%) on 07/03/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2003 Built: 1981 Tax: $2,783 (2025)Community: Greenview At Winter PinesSingle Family
Taxes:$2,783
Remarks: Virtually Staged. OUTSTANDING RENOVATION in a FANTASTIC LOCATION! Peace, Quiet & GOLF COURSE LIVING! This rare opportunity places you along the 13TH tee & offers tranquil backyard views of the 16TH fairway of the Winter Park Pines Golf Course (WP18)! Tree-lined street welcomes you to this completely renovated Floor to Ceiling ONE STORY beauty offers Serendipity LW Wood & porcelain tile flooring throughout. Updates include (but definitely not limited to) BRAND new kitchen with Stainless Steel Appliances, new cabinets & quartz countertops. Formal living & dining rooms PLUS Family room with vaulted ceilings featuring a new electric fireplace for amazing ambiance and sliding doors inviting you to new brick pavered 31x 11 screened porch overlooking newly refinished sparkling pool & golf course (no rear or side neighbors!!) Bedroom wing of home offers a large inside laundry room, beautiful guest/pool bath with dual sinks & shower/tub and 2 fresh guest bedrooms. THE PRIMARY SUITE has been thoughtfully remodeled with sliding doors to pool, AMAZING primary bath with oversized work-of-art shower with dual shower heads, dual vanity, separate water closet & HUGE walk-in closet! Extras include: NEW double paned windows & 3 sliding doors to pool/patio, crown molding, NEW roof November 2024, oversized 2 car garage, NEW landscaping, all NEW ceiling fans & light fixtures, NO HOA!! Zoned for Brookshire Elementary, Glenridge Middle & Winter Park High. WELCOME HOME!
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Catherine D'Amico (407-252-3210)
1120 WISCONSIN AVE, WINTER PARK, FL 32789
$1,084,00064 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
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)
1649 HARMON AVE, WINTER PARK, FL 32789
$1,250,000131 Days on yellowkey MLS ID: O6392216
REDUCED by $99,900 (7.4%) on 06/12/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3223 Built: 2018 Tax: $11,908 (2025)Community: LawndaleSpa: YesSingle Family
Taxes:$11,908
Remarks: Discover Orwin Manor, one of Winter Park’s established neighborhoods centrally located within an easy distance to the Orange Avenue WP corridor and minutes to downtown Orlando. Transitional architecture with modern leaning influences, this home is designed for ease of living. This four-bedroom 3.5-bath home stretches across nearly 3,200 square feet and features open kitchen to dining and living spaces that all blend into a covered porch to backyard retreat. The kitchen is the center of the home with custom double-stacked cabinetry to ceiling, upgraded appliances, large pantry with barn door, center island with bar seating, and full granite slab backsplash and counters add to the artistry of the kitchen. Ceilings are upgraded throughout with floating box details with ambient lighting that gently wash the ceilings and colors can be changed as you wish. Dining and living spaces are generous, and lined with transom windows for privacy and natural light that creates a beautiful backdrop to gather and entertain in. Invisible back doors fully open to the lanai and slide into the wall, staying hidden, an elegant upgrade. Covered porch with tongue and groove ceiling overlooks saltwater pool with hot tub and spillway. Professionally landscaped includes a turfed putting green for the golf enthusiast. Additional main floor flex space can be additional living or home office. Secondary bedrooms are upstairs with generous bonus space and laundry. First-floor primary suite is light and bright, with coffered ceilings and a large walk-in closet. Primary bath is neutrally appointed with dual floating vanities with vessel sinks, a soaking tub, and walk-in shower with seamless glass. A transom window provides privacy and a glow of sunshine and warmth. Lots of seller upgrades. This property is turnkey. Orwin Manor is a special neighborhood blending historic homes with new builds and great neighborhood park to go to. It is also a strategic location, minutes to Park Avenue in Winter Park, known for its upscale dining, elevated cafés and luxury local shopping, also a short distance to Orange Avenue corridor in WP featuring Foxtail Coffee & Buttermilk Bakery and more, and minutes to the Mills district, Advent Health on Rollins as well as major roadways. Great schools, zoned for Edgewater High, known for its magnet program and close to Lake Highland and many other private school options.
Listing Agent: Alison Mosley (407-304-6458)
7336 FOREST HILL CT #240, WINTER PARK, FL 32792
$163,500152 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
Elementary School: None
High School: None
Middle School: None
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
$499,000134 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
$1,040,00090 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)
7733 COUNTRY PL #G2, WINTER PARK, FL 32792
$229,50037 Days on yellowkey MLS ID: O6418682
REDUCED by $5,000 (2.1%) on 07/17/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1068 Built: 1982 Tax: $371 (2025)Community: Goldenrod Villas CondoCondo
Taxes:$371
Remarks: Step into a remodeled condominium in Goldenrod Villas, a peaceful, well-established community. This renovated, 2-bedroom, 2-bath villa features a light and airy layout and puts you in one of Central Florida's most coveted zip codes. With more than 1000 square feet of updated, move-in-ready living space, it's the perfect low-maintenance home base for a busy homeowners who wants style, comfort, and location all in one. The refurbished kitchen features quartz countertops, a tiled backsplash, new stainless-steel appliances (including a built-in microwave), freshly painted cabinets, and a laundry closet. No more laundromats!!The living room opens to a private, shaded, custom designed, screened patio, along with a fenced backyard that offers a quiet escape after a long day or space for a pet or other outdoor activities. Both bedrooms are generously sized with more than ample walk-in closets. Both bathrooms have new tile floors, new cabinets, sinks, toilets, and bright lighting. Practical upgrades have already been done for you: brand-new HVAC, duct work, water heater, plumbing, lighting, knock-down ceilings, flooring, and updated fixtures throughout. Custom windows will soon be installed, too. The roof was recently replaced, too. Home-buying worries be gone! What are we near—that is enticing? Drive outside the community and you're minutes from Aloma Avenue shopping, and major corridors including SR 436, 417, and 408.
Listing is courtesy of: PROPERTIES BY PATTY PLLC (407-896-3850)
Listing Agent: Patty Farless (407-924-7024)
275 N RANGER BLVD, WINTER PARK, FL 32792
$759,00049 Days on yellowkey MLS ID: O6415904
REDUCED by $16,000 (2.1%) on 07/22/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1950 Built: 1965 Tax: $6,817 (2025)Community: Winter Park PinesSpa: NoSingle Family
Taxes:$6,817
Remarks: Completely reimagined and professionally renovated, this stunning Winter Park POOL home offers approximately 1,950 square feet of thoughtfully designed living space with a rare 4-bedroom, 3-full bathroom floor plan, a 2-car garage, and an exceptional blend of style, function, and quality craftsmanship. At the heart of the home is a show-stopping open-concept kitchen featuring custom shaker cabinetry, quartz countertops, a dramatic oversized center island, designer lighting, a custom range hood, and a striking tile feature wall that creates a true focal point for the home. Warm wood accents, curated finishes, and seamless flow into the living and dining spaces make this home ideal for both everyday living and entertaining. The split-bedroom floor plan provides privacy and flexibility, with the primary suite situated on one side of the home and the secondary bedrooms located on the opposite side. All three bathrooms have been completely gutted and beautifully remodeled with high-end finishes and timeless design selections. Luxury vinyl plank flooring extends throughout the home, creating a cohesive and modern aesthetic. Major improvements include a NEW roof (2026), NEW AC system, NEW windows, NEW electrical, NEW water heater, RESURFACED POOL, updated lighting throughout, inside laundry room, and extensive interior renovations that allow buyers to enjoy the benefits of a truly move-in-ready home. Situated in the highly desirable Winter Park Pines area, residents enjoy convenient access to Park Avenue, Downtown Winter Park, Cady Way Trail, Rollins College, Full Sail University, UCF, shopping, dining, major roadways, and Orlando International Airport. Combining designer finishes, an open modern layout, a private pool, and an unbeatable location, this is a rare opportunity to own a fully renovated home in one of Central Florida's most sought-after communities. Schedule your private showing today.
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Belinda Gonzales (321-277-8994)
786 MCINTYRE AVE, WINTER PARK, FL 32789
$625,00017 Days on yellowkey MLS ID: O6424399
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1934 Built: 1988 Tax: $4,061 (2025)Community: Trotters RepTownhouse
Taxes:$4,061
Remarks: Virtually Staged. Welcome to 786 McIntyre Avenue, Winter Park, FL 32789—a serene retreat perched on a picturesque tree-lined brick street in one of Winter Park's most desirable neighborhoods. Just a short stroll from Rollins College and the renowned shops, restaurants, and charm of Park Avenue, this exceptional single-family townhome offers the perfect blend of comfort, style, and location—SINGLE FAMILY TOWNHOME with NO HOA! A charming driveway leads to the attached two-car garage and private front entrance. Inside, you'll be welcomed by a bright, airy interior featuring soaring ceilings, dramatic high windows, abundant natural light, and a cozy wood-burning fireplace. The spacious living room is surrounded by two private patios, creating a seamless connection between indoor and outdoor living. The updated kitchen boasts modern cabinetry, an open breakfast bar, and a cheerful eat-in dining area with direct access to one of the patios. The formal dining room, currently used as a home office, opens to the second patio, making it the perfect setting for al fresco dining or entertaining. Upstairs, the impressive 23' x 12' primary suite offers a peaceful retreat, complete with a spacious 20' x 8' ensuite bathroom. Two additional guest bedrooms share a convenient Jack-and-Jill bathroom, providing comfort and privacy for family or visitors. Meticulously maintained, this home features numerous recent updates, including a new HVAC system (2025) and beautiful wood shutters throughout. Located in the highly sought-after Audubon K-8 and Winter Park High School districts, this exceptional home combines timeless character, modern updates, and an unbeatable location. WELCOME HOME!
341 E READING WAY, WINTER PARK, FL 32789
$1,695,00029 Days on yellowkey MLS ID: O6420387
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3723 Built: 2007 Tax: $20,249 (2026)Community: CharmontSpa: YesSingle Family
Taxes:$20,249
Tax Year: 2026
Remarks: Virtually Staged. A rare opportunity to live on a quiet one-way street overlooking a park in the heart of Winter Park. Built in 2007 and meticulously maintained, this exceptional 4-bedroom, 4-bath pool home with a dedicated office offers timeless design, thoughtful updates, and an unbeatable location. A welcoming covered front porch provides the perfect spot to enjoy your morning coffee. Inside, soaring ceilings, extensive moldings, travertine and hardwood floors, and abundant natural light create an elegant first impression. Just off the foyer, French doors open to a private office, ideal for working from home. A secondary bedroom and full bath with a walk-in shower are conveniently located on the main level. The spacious kitchen flows seamlessly into the family room and features granite countertops, solid wood soft-close cabinetry, a gas cooktop, wall oven, breakfast bar, wet bar, walk-in pantry, and a sunny breakfast nook overlooking the lanai and pool. The adjoining family room is anchored by a gas fireplace and French doors leading outdoors. The covered lanai showcases a tongue-and-groove ceiling and remote-controlled screens, creating the perfect setting for year-round entertaining. The generous first-floor primary suite offers space for a sitting area and features two custom walk-in closets, dual vanities, a soaking tub, separate shower, and private water closet. A beautiful wrought-iron staircase leads upstairs to two generous en-suite bedrooms and a cozy loft. The private backyard is designed for relaxation and entertaining, featuring a saltwater pool and spa surrounded by lush landscaping. Additional highlights include two newer HVAC systems (2022 and 2023), a gas water heater (2022), central vacuum system, built-in Home Team pest defense system, and plantation shutters throughout. Located within the highly sought-after Audubon K-8 and Winter Park High School districts, this exceptional home is ideally situated between Park Avenue and Corrine Drive, with downtown Orlando just minutes away.
Listing Agent: Wendy Williams Crumit (321-356-8590)
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