Location: Winter Park
Do Not Show Listings
1500 GAY RD #18D, WINTER PARK, FL 32789
$275,0008 Days on yellowkey MLS ID: O6422691
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1026 Built: 1972 Tax: $3,244 (2025)Community: Chateaux Du LacCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,244
Elementary School: Killarney Elem
High School: Edgewater High
Tax Year: 2025
Middle School: College Park Middle
Remarks: Welcome home to carefree lakefront living in the heart of Winter Park, where everyday life is complemented by breathtaking sunsets over beautiful Lake Killarney and one of Central Florida's most walkable locations. Nestled within the Chateaux Du Lac lakefront community, this beautifully updated second-floor condominium offers 2 bedrooms, 2 bathrooms, and an inviting open floor plan designed for comfortable everyday living. Stepping inside, plantation shutters throughout the home create a timeless look while allowing natural light to fill the space. The spacious living and dining areas flow seamlessly together, making entertaining both easy and enjoyable. The updated kitchen is sure to impress with quartz countertops, a center island, modern subway tile backsplash, stainless steel appliances, and recessed lighting that completes the contemporary design. The owner's suite provides a relaxing retreat complete with an updated ensuite bathroom featuring stunning floor-to-ceiling herringbone-style subway tile, an overhead rain showerhead, and modern finishes. The guest bedroom is generously sized and offers a large walk-in closet, while the second bathroom has been beautifully updated to match with the same designer tilework and rain showerhead. Sliding glass doors lead out to your private balcony, creating the perfect place to enjoy your morning coffee or unwind in the evening after a day on the lake. A brand-new water heater installed in 2026 provides added peace of mind. Residents of Chateaux Du Lac enjoy an exceptional lakefront lifestyle with access to a heated swimming pool, clubhouse, community deck overlooking Lake Killarney, private boat ramp, BBQ grilling area, saunas, kayak and paddleboard storage, and updated on-site laundry facilities. Whether you enjoy boating, skiing, paddleboarding, fishing, or simply taking in spectacular sunset views, this amenity-rich community offers everything you need to embrace the Florida lifestyle. Perfectly positioned just moments from Park Avenue, you'll enjoy easy access to locally owned restaurants, boutique shopping, cafés, Trader Joe's, the Winter Park Village, movie theater, farmers markets, and the nationally recognized Winter Park Sidewalk Art Festival. With convenient access to I-4, commuting throughout the Orlando area is effortless while still enjoying the charm and elegance that make Winter Park one of the area's most desirable communities. Schedule your showing today!
Listing is courtesy of: MAVREALTY (727-314-3942)
Listing Agent: Robert Kirkwood, Iv (321-297-6489)
311 E MORSE BLVD #7-11, WINTER PARK, FL 32789
$299,000321 Days on yellowkey MLS ID: O6337061
REDUCED by $10,900 (3.5%) on 05/24/2026
Bed: 1 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 570 Built: 1960 Tax: $668 (2024)Community: Phillips Circle RepCondo
Taxes:$668
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Charming Downtown Winter Park Pied-à-Terre – Steps from Park Avenue! Welcome to Whispering Waters, a beautifully maintained mid-century community nestled on the shores of Lake Osceola. This light-filled corner studio offers a rare opportunity to own a piece of Winter Park’s most coveted location—just steps from Park Avenue, Central Park, and all the cultural charm the city has to offer. Located on the second floor, this spacious studio boasts an updated kitchenette, generous storage, and abundant natural light. Enjoy secure garage access, mail and package delivery to your door, and a relaxing retreat with sunrise views, osprey sightings, and even rocket launches visible from the community patios. Community Amenities: Sparkling pool, Club room for social gatherings, Peaceful outdoor patios overlooking Lake Osceola and Professional on-site management. Location Highlights include being one block to Park Avenue’s boutiques, cafes, and fine dining. Close to The Alfond Inn, museums, and galleries. Walkable to SunRail & Amtrak station. Moments from the Winter Park Farmers’ Market. This is a rare opportunity to own a stylish, low-maintenance home in the heart of downtown Winter Park where ELECTRIC, GAS, WATER, SEWER and TRASH are included in condo fee. Whether you're looking for a weekend retreat or full-time residence, this pied-à-terre is truly one-of-a-kind. Call today for your private viewing of this condo.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Mary Colton (407-222-7388)
2500 LEE RD #104, WINTER PARK, FL 32789
$254,90034 Days on yellowkey MLS ID: TB8517242
REDUCED by $5,099 (2.0%) on 07/07/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 956 Built: 1969Monthly Fee: $431 Tax: $2,327 (2025)Community: Lakeside Manor Apts CondoSpa: NoCondo
Taxes:$2,327
Remarks: Beautifully renovated and move-in ready 2-bedroom, 2-bath condominium offers thoughtful upgrades and a seamless open layout in one of Winter Park's most desirable lakefront communities. The heart of the home is the fully renovated kitchen (2025), featuring custom, soft close cabinetry with a built-in refrigerator surround, matching energy-efficient appliances, quartzite countertops, a light granite sink, and carefully selected high-end finishes, including antique brass hardware and faucet. Vinyl flooring creates a clean, cohesive look across the residence. Additional recent improvements include: Renovated primary shower featuring Italian porcelain tile and added storage shelving (2026) , Dining room chandelier and bedroom ceiling fans (2026), Fresh paint throughout (2026) Tankless water heater (2025) , New A/C system (2024), professionally serviced in June 2026, Renovated hallway bathroom and added storage shelving (2024). The floor plan offers a bright, open living space with two points of entry and an easy flow between the kitchen, dining, and living areas. Beyond the unit itself, residents enjoy an exceptional list of community amenities. The HOA includes water, trash, Spectrum high-speed internet, cable television with 150+ channels, and access to popular streaming services including Disney+, HBO Max, Peacock, and more. Set along scenic Lake Killarney, the community features a private dock, water access for boating and kayaking, a peaceful courtyard, abundant guest parking, and newly completed landscaping enhancements. The association has also recently completed significant infrastructure improvements to the community's incoming water system, with paving improvements and painting coming soon. A great opportunity to purchase a truly turnkey residence.
Listing is courtesy of: REALTY OF RIVERVIEW LLC (813-863-3948)
Listing Agent: Stephen Hachey (813-863-3948)
263 SCOTTSDALE SQ #263, WINTER PARK, FL 32792
$80,0001 Day on yellowkey MLS ID: O6424619
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1020 Built: 1974 Tax: $1,392 (2025)Community: Winter Park Woods CondoCondo
Taxes:$1,392
Elementary School: Brookshire Elem
High School: Winter Park High
Middle School: Glenridge Middle
Remarks: Great location for homeowner or investor. Located close to FullSail and UCF and major roads, shopping, eating and more. Don't hesitate to see this one before it is gone!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Lisa Wright (321-231-3141)
1000 S SEMORAN BLVD #408, WINTER PARK, FL 32792
$138,00015 Days on yellowkey MLS ID: R4911527
REDUCED by $10,000 (6.8%) on 07/13/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 776 Built: 1969 Tax: $1,937 (2025)Community: Golfside Villas CondoCondo
Taxes:$1,937
Remarks: Great for INVESTORS!..instant rent upon closing, start collecting the day after closing!!..Also can be great Spacious Other units currently available in same complex Great starter home../ ONE bedroom condo in Golfside Villas located in the heart of Winter Park. Great location for travel to Winter Park, Full Sail, UCF and/or the airport. Low HOA fees that cover all exterior items, along with pool and other amenities. Water and sewer is though HOA fees , nice bonus for tenants. This condo home is investment property with a long term tenant but can be ready for an owner occupant Current tenant is under market rent… opportunity to make some changes here. Schedule a showing today!
Listing is courtesy of: KIMBRIDGE REALTY, LLC (407-755-7367)
Listing Agent: Scott Butts (321-239-8509)
1000 S SEMORAN BLVD #404, WINTER PARK, FL 32792
$138,00015 Days on yellowkey MLS ID: R4911526
1000 S SEMORAN BLVD #306, WINTER PARK, FL 32792
$138,00015 Days on yellowkey MLS ID: R4911525
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 796 Built: 1969 Tax: $1,987 (2025)Community: Golfside Villas CondoCondo
Taxes:$1,987
Remarks: Virtually Staged. Great for INVESTORS!..instant rent upon closing, start collecting the day after closing!!..Also can be great Spacious Other units currently available in same complex Great starter home../ ONE bedroom condo in Golfside Villas located in the heart of Winter Park. Great location for travel to Winter Park, Full Sail, UCF and/or the airport. Low HOA fees that cover all exterior items, along with pool and other amenities. Water and sewer is though HOA fees , nice bonus for tenants. This condo home is investment property with a long term tenant but can be ready for an owner occupant Current tenant is under market rent… opportunity to make some changes here. Schedule a showing today!
2383 SUN VALLEY CIR #2383, WINTER PARK, FL 32792
$245,00085 Days on yellowkey MLS ID: O6400674
REDUCED by $5,000 (2.0%) on 07/11/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1295 Built: 1985Monthly Fee: $499 Tax: $2,560 (2024)Community: Cedarwood Village 1Condo
Taxes:$2,560
Elementary School: English Estates Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
Remarks: Nestled in a peaceful setting within the serene Cedarwood Village community, this charming one-story Winter Park condo offers a quiet retreat away from traffic noise, with a rear wooden fence for no visible neighbors for added privacy. The spacious 27-foot tiled and enclosed lanai creates the perfect place to relax and enjoy the tranquil surroundings. Cedarwood Village also offers low-maintenance living, with lawn care included in the HOA, along with amenities such as rebuilt tennis courts, a recently remodeled pool, a clubhouse, dog-walking areas, and newly paved roads. Conveniently located in a highly rated school district and close to shopping, dining, and entertainment, the property is also just minutes from Full Sail University, Valencia College, and UCF. Inside, the condo is beautifully updated and shows the care of meticulous owners. The modern kitchen features granite countertops, matching cabinetry, and an eat-in area with sliding doors leading to the private patio, while the bathrooms and dining room wet bar are finished with the same stylish cabinets and granite. The split floor plan includes tile flooring throughout the main living areas and wood floors in the bedrooms. The large living and dining spaces feature vaulted ceilings with skylights for abundant natural light, along with a cozy wood-burning fireplace. French doors from the living room open to the enclosed lanai, while the primary suite also has direct lanai access, ample closet space, and a private bath with both a tub and shower. Additional features include an interior laundry closet adjacent to the kitchen, updated plumbing, a roof replaced in 2018, and new ductwork installed in 2023. AC 2008. Seller providing a $5,000 Buyer credit at closing toward a new AC and Water Heater. Two assigned parking spaces are located directly in front of the unit.
Listing is courtesy of: WEICHERT REALTORS HALLMARK PROPERTIES (407-644-5385)
Listing Agent: Jeff Stewart (407-247-9762)
311 E MORSE BLVD #1-3, WINTER PARK, FL 32789
$1,895,00067 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
Middle School: Audubon Park K-8
Remarks: Enjoy the Winter Park lifestyle in this beautifully renovated 2-bedroom, 2-bath lakefront condo offering 2,304 square feet in the heart of downtown Winter Park. Located on the second floor of Building 1, this light-filled residence was extensively remodeled in 2023 with an open floor plan and raised ceiling heights that give the home an airy, comfortable feel throughout. The spacious living room and kitchen take full advantage of the breathtaking views of Lake Osceola, while two fireplaces—one in the living room and another in the primary bedroom—add warmth and character to the space. The kitchen has been updated with white cabinetry, stainless steel appliances, double ovens, induction cooktop, tile backsplash, center island, and wine/beverage refrigerator. Formal living and dining spaces offer plenty of room for entertaining, and the oversized entertainment room off the primary bedroom features a closet and separate entry, making it a great option for a third bedroom, media room, or home office. The primary suite offers a walk-in closet and en-suite bathroom with a shower and dual sinks. The secondary bedroom includes two closets along with a separate alcove ideal for a reading nook or office space. A Florida room, currently used as a storage room, features brick flooring. Other highlights include plantation shutters throughout, beautiful exposed beams, additional storage closet in the garage, and two designated parking spaces in the covered garage. Residents enjoy a community pool, gated underground parking with elevator access, and an unbeatable location just steps from Park Avenue’s shops, restaurants, museums, and seasonal events. A rare opportunity to enjoy spacious lakefront living in one of Winter Park’s most desirable communities.
Listing Agent: Megan Cross (407-353-9997)
1695 LEE RD #B108, WINTER PARK, FL 32789
$89,9997 Days on yellowkey MLS ID: O6422568
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 638 Built: 1966Monthly Fee: $347 Tax: $1,781 (2025)Community: Waterfall Cove Of Winter ParkCondo
Taxes:$1,781
Remarks: This charming 1bedroom, 1bathroom condo is a fantastic opportunity for both homeowners and investors. Located in a desirable area close to shopping, restaurants, and everyday conveniences, it offers comfort, convenience, and excellent value. The kitchen comes fully equipped with a refrigerator, stove, dishwasher, and microwave, and the unit also includes a washer and dryer for added convenience. Step outside onto your private outdoor balcony, the perfect spot to enjoy your morning coffee or unwind after a long day. Residents have access to a beautiful community swimming pool, creating a relaxing atmosphere to enjoy year-round. Whether you're looking for a place to call home or a great investment property, this condo has everything you need in an ideal location.
Listing is courtesy of: LOKATION (954-545-5583)
Listing Agent: Brandy Ray (949-449-5652)
1695 LEE RD #D211, WINTER PARK, FL 32789
$109,00097 Days on yellowkey MLS ID: O6396190
REDUCED by $5,000 (4.4%) on 07/06/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 881 Built: 1966 Tax: $2,051 (2025)Community: Waterfall Cove/Winter ParkCondo
Taxes:$2,051
Remarks: Welcome to this lovely open-concept 2 bedroom, 1 bathroom condo, perfectly situated in a fantastic area close to plenty of shopping, dining, and everyday conveniences. Ideal for first-time buyers, downsizing, or investors looking for a solid opportunity! This property highlights an open-concept bright interior with great natural light living and dining area. Two spacious bedrooms with 1 bathroom. Durable vinyl flooring with cozy carpeted bedrooms with a spacious walk in in closet in the primary bedroom. You will get a private balcony perfect for morning coffee or evening relaxation and the convenience of your our laundry with washer and dryer hookups included. This condo is perfectly located in a desirable area of Winter Park close to tons of and amenities.
205 LEWFIELD CIR #205, WINTER PARK, FL 32792
$182,900183 Days on yellowkey MLS ID: S5141588
REDUCED by $37,100 (16.9%) on 06/20/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 927 Built: 1973 Tax: $796 (2024)Community: Stratford A Winter Park CondoCondo
Taxes:$796
Remarks: INVESTOR - MOTIVATED SELLER - PRICE ADJUSTED! Wonderful! Exceptional Winter Park location! Amenities include 2 pools, lighted tennis courts, fitness center, car care facilities & clubhouse, enjoy the simple life in this 2 bedroom, 2 bath, ground floor unit. Sip your morning coffee while admiring the garden landscaping from your screen enclosed patio. Host a BBQ with family and friends at the community clubhouse or enjoy shopping at the many neighborhood retail and grocery outlets nearby. The quaint restaurants, coffee houses, golf courses, and farmers markets of Winter Park and Baldwin Park are within biking distance. There is always something to see and do at this prime location. Recent upgrades include: new electric panel (2024), new washer/dryer in unit (2024), new dishwasher (2023), refrigerator (2020).
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Eimi Moreno Carrera (321-945-6195)
1500 GAY RD #3C, WINTER PARK, FL 32789
$248,00026 Days on yellowkey MLS ID: O6417533
REDUCED by $2,000 (0.8%) on 07/09/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1026 Built: 1972Monthly Fee: $425 Tax: $3,244 (2025)Community: Chateaux Du LacCondo
Remarks: New Price/Seller Motivated! WINTER PARK LOCATION ALERT with AMAZING WALKABILITY to SO MANY shopping and dining options! Across from the newly renovated WP Shopping Village that includes top-rated restaurants, a movie theater, boutiques, grocery store and more! This 2bedroom/2 bathroom attractive second-story unit offers an updated kitchen and bathrooms with solid countertops. All solid flooring throughout - tile and laminate for easy care...no carpet. Enjoy the dining space that opens to the large great room and balcony where you'll love sitting in the evenings to relax. SPACIOUS BEDROOMS - Primary bedroom has an attached full bathroom and bedroom 2 has a LARGE walk-in closet. The 2nd Full Bathroom is accessed via a common hallway. The Chateaux Du Luc LAKEFRONT COMMUNITY offers FABULOUS AMENITIES that include an oversized heated pool, clubhouse, community deck, BBQ grill, 2 on-site saunas, updated on-site laundry facilities, and a resident-only boat ramp on skiable Lake Killarney. There's even storage for your Kayak or paddleboard! Roof 2025. Reach out today for your personal showing!!
Listing Agent: Heather Frazee (321-689-9465)
101 S NEW YORK AVE #311, WINTER PARK, FL 32789
$1,849,90027 Days on yellowkey MLS ID: O6416927
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3112 Built: 2008Monthly Fee: $1,303 Tax: $20,039 (2025)Community: Winter Park ResidentialCondo
Taxes:$20,039
Elementary School: Audubon Park K8
Remarks: Discover luxury living in this exquisitely renovated two-story condominium, ideally situated on the third floor of the highly sought-after Douglas Grand in the heart of Winter Park. This elegant three-bedroom, three-and-one-half-bath residence seamlessly blends sophisticated design with everyday comfort. Immediately captivating, the light-filled open floor plan showcases stunning new wide-plank white oak flooring, high ceilings, detailed crown molding, and all-new designer lighting throughout. The chef’s kitchen is a showpiece, featuring crisp white cabinetry, luxurious white quartz countertops, a spacious breakfast bar island, elegant gold hardware, and a built-in desk. A charming breakfast nook offers the perfect setting for morning coffee or casual dining. French doors open to a private enclosed atrium, creating a versatile outdoor retreat ideal for alfresco dining, relaxing, or entertaining guests in style. The expansive living and dining spaces flow effortlessly, while a private first-floor bedroom with en suite bath and walkout balcony provides an ideal space for guests, multigenerational living, or a home office. Upstairs, the primary suite serves as a peaceful sanctuary, complete with an indulgent soaking tub, dual vanities, an oversized walk-in closet, and French doors leading to a large private balcony with sweeping views of Winter Park's iconic Park Avenue—perfect for enjoying sunrise coffee or evening sunsets. A second upstairs en suite bedroom offers its own private bath and generous walk-in closet. Thoughtful features include an upstairs laundry room, a spacious storage closet with potential elevator conversion for future accessibility, and a secure gated garage with two reserved parking spaces. Perfectly positioned in the heart of Winter Park, Douglas Grand places you just steps from Park Avenue, the Winter Park Farmers’ Market, Rollins College, Hannibal Square, Winter Park Golf Course, the Winter Park Tennis Center, Winter Park Village, and an array of renowned dining, shopping, and cultural attractions. Enjoy an unparalleled walkable lifestyle in one of Central Florida's most desirable communities. Notable improvements include an interior renovation (2026), front elevation windows and French doors (2024), interior paint (2024), and HVAC system (2022).
Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)
Listing Agent: Tiffany Grindstaff (407-252-0927)
1500 GAY RD #17D, WINTER PARK, FL 32789
$249,90057 Days on yellowkey MLS ID: O6408516
REDUCED by $10,000 (3.8%) on 07/08/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1026 Built: 1972 Tax: $3,244 (2025)Community: Chateaux Du LacSpa: NoCondo
Remarks: MAJOR PRICE ADJUSTMENT! Fantastic Winter Park Location on Lake Killarney. This 2 Bedroom 2 Bath Upstairs Unit has Lake and Pool Views. Spacious Living Spaces and Generously-sized Bedrooms. Unique Updated Kitchen has Sub Zero Refrigerator, Bosch Dishwasher, Solid Surface Counters, unbelievable amount of Storage with Corner Cabinets, Drawers, pull-out Shelving and 3 Tiers of Lighting! Updates include: Water Heater in 2023, Range 2019, Refrigerator in 2020, A/C in 2020, Double-Pane Windows and Sliding Door in 2016, Updated Electric Panel, Replaced Ductwork and added Attic Insulation. Master Bath has Double-Sink Vanity. Guest Bath has newer Vanity and Retiled Shower with replaced Shower Pan. Unit recently Replumbed. Plantation Shutters, recently Repainted and Carpeted. Short Walk to Shopping, Restaurants, Theaters, and minutes to Park Avenue with it's Village Style Shopping, Central Park with Bandstand, Spring and Fall Art Festivals, Farmer's Market and Downtown Train Station. Drive into the Community, catch a view of the Lake, watch a Sunset on the Deck and you will know "you're Home"! OWNER WILL CONSIDER REPLACING CARPET IN LIVING AREA WITH LUXURY VINYL FLOORING WITH ACCEPTABLE CONTRACT!
Listing is courtesy of: REALCOM REAL ESTATE SERVICES INC (407-621-6856)
Listing Agent: Janice Erickson (407-621-6856)
151 N ORLANDO AVE ##115, WINTER PARK, FL 32789
$290,000224 Days on yellowkey MLS ID: O6362403
REDUCED by $8,000 (2.7%) on 06/28/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 710 Built: 1960 Tax: $2,965 (2025)Community: Lake Killarney CondoSpa: NoCondo
Taxes:$2,965
Remarks: Welcome to Lake Killarney Living ... Where Winter Park charm meets everyday convenience. Furniture negotiable, offering added flexibility for buyers or investors. Discover this beautifully appointed 2-bedroom, 1-bath condo in the highly sought-after Lake Killarney Condo Community, perfectly positioned just steps from Winter Park Village, dining, shopping, and the peaceful waters of Lake Killarney. Inside, you’ll find a bright, natural light–filled living space with an intimate, inviting feel. The efficient galley kitchen flows seamlessly into the living and dining area, making the home feel larger than its square footage. A rare bonus for condo living, the home includes a separate laundry room, offering added convenience and additional storage. Step outside to your private patio space, perfect for morning coffee, quiet evenings, or creating your own cozy outdoor retreat. There’s even room for a foosball table, making it a great spot to unwind, entertain, or simply grab a Coke and smile as you enjoy the Florida breeze. Residents enjoy an impressive list of community amenities, including a sparkling private pool, lush green spaces, and access to Lake Killarney’s private community dock, ideal for launching kayaks and paddleboards, fishing, or taking in serene lakefront views. Enjoy evening sunset strolls, weekend boating, or a relaxing afternoon by the pool. The community also offers convenient on-site laundry facilities, beautifully maintained grounds, and a welcoming neighborhood atmosphere. With strong rental appeal, an unbeatable location, and timeless Winter Park charm, 151 N Orlando Ave #115 is an ideal choice for first-time buyers, downsizers, or investors seeking long-term value in one of Central Florida’s most desirable lakefront communities. Schedule your private showing today and experience the lifestyle waiting for you at Lake Killarney.
Listing is courtesy of: CREEGAN GROUP (407-622-1111)
Listing Agent: Chris Creegan (407-622-1111)
1807 HAMMERLIN AVE #G, WINTER PARK, FL 32789
$515,000119 Days on yellowkey MLS ID: O6391277
REDUCED by $10,000 (1.9%) on 06/15/2026
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
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)
283 LEWFIELD CIR #283, WINTER PARK, FL 32792
$142,50012 Days on yellowkey MLS ID: O6420915
1 Days Off yellowkey (back on 7/12/2026)
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 678 Built: 1973 Tax: $1,729 (2025)Community: Stratford A Winter Park CondoCondo
Taxes:$1,729
Remarks: Under contract-accepting backup offers. Seller may consider buyer concessions if made in an offer ~ Recently UPDATED and ready for its next owner, this light-filled FIRST FLOOR condo unit offers LOW MAINTENANCE LIVING in the desirable Stratford community of Winter Park – with a monthly HOA that's lower than many comparable communities! Step inside through the semi-private INTERIOR ENTRY to an OPEN CONCEPT floor plan featuring updated bathroom finishes, WOOD LAMINATE & TILE FLOORING throughout, and a spacious living and dining area designed for everyday comfort and easy entertaining. The kitchen is equipped with STAINLESS STEEL APPLIANCES, breakfast bar seating, and a seamless connection to the main living spaces. A convenient IN-UNIT LAUNDRY closet adds to the home's functionality, while sliding glass doors lead out to a SCREENED LANAI overlooking a large green space for the perfect spot to enjoy your morning coffee or unwind at the end of the day. Stratford is a beautifully maintained community offering a park-like setting complete with a COMMUNITY POOL and peaceful surroundings thanks to the mature trees, making it easy to enjoy the Florida lifestyle without the upkeep of a single-family home. Ideally located at the corner of Lake Howell Road and Howell Branch Road with quick access to SR 436, you will appreciate being just minutes from abundant shopping, dining, medical services, parks, and everyday conveniences. Whether you are searching for your first home, a seasonal retreat, or an investment opportunity, this well-maintained Winter Park condo is one you won't want to miss. Call today to schedule a tour!
Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)
Listing Agent: Jenny Wemert (407-809-1193)
303 SCOTTSDALE SQ #303, WINTER PARK, FL 32792
$80,0004 Days on yellowkey MLS ID: O6424296
2450 GRAND TETON CIR #2450, WINTER PARK, FL 32792
$255,0004 Days on yellowkey MLS ID: O6418973
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1311 Built: 1981 Tax: $889 (2025)Community: Cedarwood Village 1Spa: NoCondo
Taxes:$889
Remarks: Rare end units like this don't come around often! Welcome to 2450 Grand Teton Circle, tucked away in the well-maintained, established community of Cedarwood Village in Winter Park. This 3-bedroom, 2-bath home is filled with natural light thanks to its end-unit location, and the open layout makes it easy to relax, entertain and enjoy everyday living. The spacious living and dining areas flow together nicely, while the kitchen offers plenty of room to cook, gather, and stay connected with family and friends. Over the past several years, this home has been thoughtfully updated, giving the next owner peace of mind. Major improvements include a new roof, skylights, HVAC system, water heater, kitchen appliances, washer and dryer, updated LED lighting, and fresh interior paint. Both bathrooms have been beautifully remodeled, the home has been replumbed by the HOA, and the primary closet has been enhanced with custom shelving. Additional updates include new flooring in the secondary bedrooms, updated window blinds, and thoughtful finishing touches throughout. The private screened lanai has been transformed into a cozy outdoor retreat with fresh paint, a ceiling fan, new screens and screen door, string lighting, and decorative greenery—making it the perfect place to enjoy your morning coffee or unwind after a long day. Life here is easy. Cedarwood Village is a beautifully maintained, established community featuring a community pool and Clubhouse for your special events, tennis courts, and pickleball courts. The HOA has also recently repainted the exterior of the buildings, helping keep the neighborhood looking fresh and inviting. Best of all, this home is value priced, giving you an incredible opportunity to own in desirable Winter Park without the premium price tag. You're just minutes from Winter Park's shopping and dining, Full Sail University, UCF, major employers, and convenient access to SR-417 and downtown Orlando. If you've been looking for a move-in-ready home in a fantastic location with years of thoughtful updates already completed, this rare end unit is definitely worth a look!
Listing Agent: John Campese (407-310-8974)
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