Winter Park, FL Homes for Sale with Pool

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  $185,000

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,058 Sq Ft

  4756 Tangerine Ave Unit 4756, Winter Park, FL 32792

  Discover the potential of this 2-bedroom, 2-bath end-unit condominium located in the desirable Wrenwood Condominium community in Winter Park, Florida. Offering 1,058 square feet of living space, this home presents an excellent opportunity for buyers seeking affordability, convenience, and the chance to add their own personal style. Inside, you'll find ceramic tile flooring throughout, knockdown

  Ada Sanchez HOME BUYER HELPER REAL ESTATE LLC

  4756 Tangerine Ave Unit 4756, Winter Park, FL 32792
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  $514,900

  Open House 8/09 $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,627 Sq Ft

  1438 Tierra Cir, Winter Park, FL 32792

  Charming, Fully Renovated Pool Home in Sought-After Winter Park. Welcome to this beautifully updated pool home, ideally located in desirable Winter Park—just minutes from premier shopping, dining, and entertainment, with easy access to major roadways for a seamless commute.From the moment you step inside, you’re greeted by a warm, modern aesthetic that blends comfort with style. To the right,

  Tony Nicolas COLDWELL BANKER REALTY

  1438 Tierra Cir, Winter Park, FL 32792
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  /7

  $2,099,000

  New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,865 Sq Ft

  938 Enclave Place, Winter Park, FL 32792

  Pre-Construction. To be built. Welcome to The Enclave, an exclusive boutique community in the heart of Winter Park featuring just 23 thoughtfully crafted residences by FG Schaub Custom Homes. Nestled beneath mature oak canopies and surrounded by lush natural beauty, this private enclave offers the perfect balance of tranquility, sophistication, and walkable convenience. Ideally located just

  Laura Earl CORCORAN PREMIER REALTY

  938 Enclave Place, Winter Park, FL 32792
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  $1,295,000

  $54K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,843 Sq Ft

  802 Hamilton Place Ct, Winter Park, FL 32789

  Now offered out an exceptional new price, the seller has thoughtfully repositioned this home to encourage serious buyer interest – seller is actively moving. This remarkable home represents one of the best opportunities in today’s Winter Park luxury market, featuring exquisite finishes, modern design, and an unmatched lifestyle just moments from Park Avenue.Built in 2018, this custom-designed

  Jacob Theisen FLORIDA CAPITAL REALTY

  802 Hamilton Place Ct, Winter Park, FL 32789
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  $1,599,000

  • 5 Beds
  • 3.5 Baths
  • 3,028 Sq Ft

  1864 Grinnell Terrace, Winter Park, FL 32789

  Situated in the heart of Winter Park, this custom-built Mediterranean-style estate offers an exquisite living experience that marries timeless architecture with modern innovation. A dramatic grand foyer introduces a residence where every finish has been meticulously curated, from Turkish travertine stone and rich wood flooring to Brizo hardware in Brilliance Polished Gold. At the heart of the

  Robyn Brehne COLDWELL BANKER REALTY

  1864 Grinnell Terrace, Winter Park, FL 32789
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  $799,900

  $25K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,164 Sq Ft

  722 S Ranger Blvd, Winter Park, FL 32792

  JUST REDUCED! 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,

  Karen Gore CHARLES RUTENBERG REALTY ORLANDO

  722 S Ranger Blvd, Winter Park, FL 32792
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  $205,000

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,149 Sq Ft

  1695 Lee Rd Unit C202, Winter Park, FL 32789

  This property located in a peaceful community IN WINTER PARK. and easy access to FL I-4 , short drive distance to Rollins College, UCF, Valencia college, Hospitals, shopping center, restaurants and Orlando Theme Park. This unit located on the second floor, it has 3 bedrooms 2, bathrooms, open floor plan. The community amenities include a large pool with lounge chairs, playground and gazebo. This

  Hoover Yap PRIMESTATE REALTY, INC.

  1695 Lee Rd Unit C202, Winter Park, FL 32789
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  /4

  $1,899,000

  New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,620 Sq Ft

  910 Enclave Place, Winter Park, FL 32792

  Pre-Construction. To be built. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneath mature oak canopies being built by FG Schaub Custom Homes. A short walk to Phelps Park, YMCA, dinner and shopping. Surrounded by natural beauty and designed with intention, The Enclave offers a rare opportunity to enjoy a

  Laura Earl CORCORAN PREMIER REALTY

  910 Enclave Place, Winter Park, FL 32792
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  /38

  $1,795,000

  • 3 Beds
  • 3.5 Baths
  • 2,399 Sq Ft

  621 Huntington Ave, Winter Park, FL 32789

  Experience elevated living in this fully transformed luxury residence in the heart of Winter Park, where design, premium finishes, and effortless functionality come together seamlessly. This 3-bedroom, 3.5-bath pool home offers approximately 2,400 square feet of impeccably curated living space, designed for those who appreciate both style and substance. Expertly designed by Morrone Interiors,

  Noelle LeBlanc OLDE TOWN BROKERS INC

  621 Huntington Ave, Winter Park, FL 32789
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  /34

  $499,000

  $31K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,092 Sq Ft

  2217 Sussex Rd, Winter Park, FL 32792

  PRICE REDUCED!!! ROOF 4 yrs. old, newer A/C, In-ground Pool. Enclosed Patio — a beautifully maintained turnkey home nestled in the heart of Winter Park, one of Central Florida’s most sought-after communities. Surrounded by renowned golf courses, top-rated Seminole County schools, lush parks, and family-friendly neighborhoods, this exceptional residence offers the perfect blend of comfort,

  Thess Hubilla PREFERRED REAL ESTATE BROKERS

  2217 Sussex Rd, Winter Park, FL 32792
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  $149,000

  $16K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 645 Sq Ft

  2500 Lee Rd Unit 232, Winter Park, FL 32789

  LAKEFRONT living just steps from the shore of 239-acre, spring-fed Lake Killarney! Welcome to Lakeside Manor and this charming second-floor end-unit condo offering partial lake views, private lake access, and an ideal blend of comfort and convenience.This 1-bedroom, 1-bath unit features a bright and inviting layout with luxury vinyl plank flooring throughout the main living areas,

  Wendy Rodriguez COLDWELL BANKER REALTY

  2500 Lee Rd Unit 232, Winter Park, FL 32789
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  /5

  $500,000

  • 4 Beds
  • 3 Baths
  • 2,031 Sq Ft

  2054 Eastbrook Blvd, Winter Park, FL 32792

  Check out this private pool home in lovely Winter Park. Offers 4 bedrooms, 3 baths and a 2 car garage. Huge kitchen overlooking family room. Inside laundry room. Fenced backyard. Zoned for Lake Howell High School.

  Melissa Stalzer LPT REALTY, LLC

  2054 Eastbrook Blvd, Winter Park, FL 32792
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  /14

  $179,900

  • 3 Beds
  • 2 Baths

  7340 Daniel Webster Dr, Winter Park, FL 32792

  This is a 3 bedroom and 2 bathroom condo. This condo has had everything replaced. Don't miss out on this opportunity. Call listing agent today for more information and to schedule a showing.

  Robert Castro RE/MAX - City Centre Realty

  7340 Daniel Webster Dr, Winter Park, FL 32792
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  $1,895,000

  $180K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 2,304 Sq Ft

  311 E Morse Blvd Unit 1-3, Winter Park, FL 32789

  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

  Megan Cross FANNIE HILLMAN & ASSOCIATES

  311 E Morse Blvd Unit 1-3, Winter Park, FL 32789
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  $267,000

  $12K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,295 Sq Ft

  2317 Sun Valley Cir, Winter Park, FL 32792

  Discover comfort and convenience in this charming, spacious 2-bedroom, 2-bath residence nestled in the heart of Winter Park! Step inside to an inviting living room with a vaulted ceiling. The fully equipped open-floor kitchen, featuring ample roomy cabinets, is perfect for everyday living and entertaining. The thoughtfully designed split floor plan enhances functionality and privacy. Elegant,

  Robert Arnold SAND DOLLAR REALTY GROUP INC

  2317 Sun Valley Cir, Winter Park, FL 32792
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  $1,625,000

  Open Sun 2PM - 4PM $70K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 3,723 Sq Ft

  341 E Reading Way, Winter Park, FL 32789

  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.

  Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

  341 E Reading Way, Winter Park, FL 32789
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  $2,195,000

  Open Fri 5PM - 7PM

  • 4 Beds
  • 4.5 Baths
  • 3,691 Sq Ft

  1750 Walnut Ave, Winter Park, FL 32789

  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

  Richard Palmano PALMANO GROUP RE BROKERAGE LLC

  1750 Walnut Ave, Winter Park, FL 32789
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  $460,000

  Coming Soon

  • 3 Beds
  • 2 Baths
  • 1,521 Sq Ft

  2826 Ambergate Rd, Winter Park, FL 32792

  NEW ROOF COMING! This is a great Pool home in Winter Park. Home features brick paved driveway, side entry garage, terrazzo floors throughout, new duct work, newer hot water heater and electrical panel. All new fans. Freshly Painted inside. Updated bathrooms. Kitchen has an eat in area, loads of cabinets for storage and stainless steel appliances. Step out the french doors to a covered patio that

  Rebecca Heatherington CHARLES RUTENBERG REALTY ORLANDO

  2826 Ambergate Rd, Winter Park, FL 32792
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  $500,000

  • 3 Beds
  • 2 Baths
  • 1,413 Sq Ft

  512 N Lakemont Ave, Winter Park, FL 32792

  Set on an oversized corner lot in one of the most desirable pockets of Winter Park, this 3-bedroom, 2-bath pool home blends character, location, and opportunity.The backyard is a standout feature, with a resurfaced pool finished in Tahoe Blue PebbleTec and positioned for open sky views, a rare find in a neighborhood known for its mature tree canopy. It creates a bright, inviting outdoor space

  David Plasencia COLDWELL BANKER REALTY

  512 N Lakemont Ave, Winter Park, FL 32792
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  $695,000

  • 4 Beds
  • 3 Baths
  • 2,312 Sq Ft

  715 S Ranger Blvd, Winter Park, FL 32792

  Welcome to your dream home in the highly sought-after community of Winter Park Pines! This beautifully maintained 4-bedroom, 3-bathroom residence offers 2,312 square feet of comfortable and stylish living space ideally designed for modern and multigenerational lifestyles.The recently remodeled primary suite is a true retreat, featuring new carpeting and tile flooring, dual granite vanities,

  Chuck Tolfa DAHLIA REALTY GROUP

  715 S Ranger Blvd, Winter Park, FL 32792
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  $182,900

  $67K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 927 Sq Ft

  205 Lewfield Cir Unit 205, Winter Park, FL 32792

  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

  Eimi Moreno Carrera LPT REALTY, LLC

  205 Lewfield Cir Unit 205, Winter Park, FL 32792
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  /44

  $6,888,888

  New Construction

  • 4 Beds
  • 4.5 Baths
  • 4,636 Sq Ft

  2661 Vía Tuscany, Winter Park, FL 32789

  Set in the perfect Winter Park location, within exclusive Via Tuscany, this unique, RESILIENT CONSTRUCTION residence built by Developer & Builder Group, offers a rare blend of enduring quality, refined privacy, and effortless sophistication. Showcasing the finest European finishes, premium appliances, and exquisite light fixtures; this home is filled with clear, natural light and fresh air,

  Belinda Moreno The Keyes Company

  2661 Vía Tuscany, Winter Park, FL 32789
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  /3

  $1,895,000

  New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,617 Sq Ft

  914 Enclave Place, Winter Park, FL 32792

  Pre-Construction. To be built. 914 Enclave Place is a beautiful Alys Beach inspired design. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneath mature oak canopies, being built by FG Schaub Custom Homes. A short walk to Phelps Park, YMCA, dinner and shopping. Surrounded by natural beauty and designed with

  Matthew Burks CORCORAN PREMIER REALTY

  914 Enclave Place, Winter Park, FL 32792
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  $750,000

  • 3 Beds
  • 2 Baths
  • 1,350 Sq Ft

  300 Carolina Ave Unit 402C, Winter Park, FL 32789

  Virtually Staged. Welcome to Park West Condominiums — one of Winter Park’s most coveted and rarely available condominium communities, ideally located just one block from the boutiques, dining, and charm of Park Avenue. This unique 4th floor residence offers an exceptional combination of space, privacy, and potential. Featuring 3 bedrooms and 2 bathrooms, the expansive floor plan has been enlarged

  Erin Baker FANNIE HILLMAN & ASSOCIATES

  300 Carolina Ave Unit 402C, Winter Park, FL 32789
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  $245,000

  Open Fri 12PM - 3PM $24K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,295 Sq Ft

  2383 Sun Valley Cir, Winter Park, FL 32792

  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

  Jeff Stewart WEICHERT REALTORS HALLMARK PROPERTIES

  2383 Sun Valley Cir, Winter Park, FL 32792
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  $1,262,500

  Open Sat 12PM - 4PM $13K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 3,024 Sq Ft

  2015 Summerfield Rd, Winter Park, FL 32792

  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

  Courtney Lindsay UNITED REAL ESTATE PREFERRED

  2015 Summerfield Rd, Winter Park, FL 32792
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  /21

  $140,000

  • 2 Beds
  • 2.5 Baths
  • 1,090 Sq Ft

  3021 Aaron Burr Ave Unit 3, Winter Park, FL 32792

  Townhouse opportunity—ideal for either personal residence or investment—featuring 2 bedrooms and 2.5 bathrooms. Conveniently located near supermarkets, shops, universities, and public transportation. At closing, all outstanding HOA special assessments will be paid off. The Townhome is rent $1,600. The unit is located in Winter Park Area HOME GUARANTY OF AMERICA HWA 13 MONTH INCLUDED.

  Daiana Garcia Medrano NAIM REAL ESTATE LLC

  3021 Aaron Burr Ave Unit 3, Winter Park, FL 32792
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  $159,000

  $6K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,108 Sq Ft

  7300 Daniel Webster Dr Unit 7, Winter Park, FL 32792

  Welcome home to this stunningly updated two-story condo that perfectly combines modern elegance with everyday comfort. Featuring 2 spacious bedrooms and 2.5 baths, this home has been thoughtfully updated with high-end designer finishes throughout. The first floor showcases stunning new tile flooring in a striking neutral pattern, creating a modern and inviting living space, while the second floor

  Rosa Rodriguez STIRLING INTERNATIONAL REAL ES

  7300 Daniel Webster Dr Unit 7, Winter Park, FL 32792
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  /31

  $475,000

  $65K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,592 Sq Ft

  346 S Ranger Blvd, Winter Park, FL 32792

  PRIME LOCATION! Beautiful 3 Bedroom 2 Bathroom home is located in sought after Winter Park Pines with NO HOA and NO CDD. It is situated on a Corner Lot (0.22 Acre) and is a super short distance to the High Rated schools in Winter Park. The interior is extremely well kept with engineered wood floors, crown molding, and a beautiful glass entry door. There is a captivating white-washed stone

  Tetyana Vyushkina IMPERIAL REALTY OF FLORIDA INC

  346 S Ranger Blvd, Winter Park, FL 32792
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  $598,000

  $17K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,434 Sq Ft

  4392 Wardell Place Unit 201, Orlando, FL 32814

  This exquisite second-floor condo is a rare corner unit beautifully nestled in the heart of Baldwin Park. Boasting 1,434 square feet of living space, the home features a spacious open floor plan with impressive high ceilings and stunning natural light and a wrap-around porch. Brand new luxury vinyl floors run throughout the entire home, which includes three bedrooms and two full bathrooms. The

  Brian Cirillo BALDWIN PARK REALTY LLC

  4392 Wardell Place Unit 201, Orlando, FL 32814
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  $2,995,000

  New Construction Open Sun 12PM - 3PM

  • 5 Beds
  • 6 Baths
  • 3,689 Sq Ft

  1204 Nottingham St, Orlando, FL 32803

  A REFINED CUSTOM SINGLE-STORY RESIDENCE WITH CASITA BY M. LAHR HOMES! Located in the highly sought-after Beverly Shores / Rose Isle neighborhood of Orlando / Winter Park, this newly completed custom residence represents a rare opportunity in one of Central Florida’s most desirable and seldom-available areas. This home reflects the level of craftsmanship, detail, and execution that has made the

  Robert Kurzreiter PA KELLER WILLIAMS REALTY AT THE PARKS

  1204 Nottingham St, Orlando, FL 32803
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  $689,000

  $160K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,000 Sq Ft

  2514 Tuscarora Trail, Maitland, FL 32751

  Priced below Appraised Value — and the seller is ready to move. This classic 4-bedroom, 2.5-bath Maitland pool home sits on a spacious quarter-to-half-acre lot with peaceful lake views and delivers 3,000 square feet of open, comfortable living. The updated kitchen and open floor plan make the interior as functional as it is inviting, but the real showstopper is outside — a sparkling pool

  Tom Noelke NOELKE REALTY

  2514 Tuscarora Trail, Maitland, FL 32751
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  $1,149,000

  • 3 Beds
  • 2.5 Baths
  • 2,642 Sq Ft

  2506 Woodside Ave, Orlando, FL 32803

  Welcome to 2506 Woodside Ave — a meticulously appointed 2017-built home with distinctive modern architecture tucked into one of Orlando's most beloved and established neighborhoods. Clean lines, bold design, and an unmistakable contemporary presence set this home apart on a street of charming older Florida homes and newer construction alike. Surrounded by mature trees and quiet streets where

  Steven Koleno BEYCOME OF FLORIDA LLC

  2506 Woodside Ave, Orlando, FL 32803
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  $2,490,000

  • 5 Beds
  • 5 Baths
  • 3,982 Sq Ft

  2656 Meeting Place, Orlando, FL 32814

  Set along one of Baldwin Park's most desirable park-facing streets, this fully reimagined five-bedroom, five-bath residence provides a rare blend of space, design, and lifestyle just moments from the charm of Winter Park. Spanning nearly 4,000 square feet, the home has been thoughtfully renovated with high-end custom finishes and a modern transitional aesthetic that feels both elevated and

  Chocky Burks CORCORAN PREMIER REALTY

  2656 Meeting Place, Orlando, FL 32814
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  /21

  $834,900

  • 3 Beds
  • 2 Baths
  • 1,959 Sq Ft

  2624 Tuscarora Trail, Maitland, FL 32751

  Discover a rare waterfront, pool-home in the desirable Dommerich Hills neighborhood. This exceptional property offers the ideal combination of family-friendly living, modern convenience, and breathtaking natural beauty.The open floor plan welcomes you with vaulted ceilings and natural light in the living room, dining room, kitchen, and family room. Bamboo flooring enhances the bedrooms and

  Lori Wall EPIC FLORIDA REALTY LLC

  2624 Tuscarora Trail, Maitland, FL 32751

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