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4-Bedroom Houses for Sale in Winter Haven, FL with Private Pool

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  • /67

    $975,000

    • 4 Beds
    • 4 Baths
    • 3,555 Sq Ft

    200 Island Way, Winter Haven, FL 33884

    Welcome to your own slice of paradise on the private shores of Lake Lewis located in the highly sought-after gated community of Orchid Springs Estates! This stunning Mediterranean-style estate offers the perfect blend of luxury, comfort, and timeless elegance. Boasting 4 spacious bedrooms and 4 full baths, this custom-designed home features a beautifully appointed kitchen ideal for entertaining,

    Agent Photo

    Steve Lockhart

    LOCKHART & ASSOCIATES INC

    (863) 343-1106

    200 Island Way, Winter Haven, FL 33884
  • /63

    $1,250,000

    • 4 Beds
    • 4 Baths
    • 4,070 Sq Ft

    2682 Wyndsor Oaks Place, Winter Haven, FL 33884

    PRICE JUST REDUCED $50,000! With and a new roof from 2023, this home offers its own private, covered, newly updated boathouse with a boat lift providing direct water access via private canal to Lake Winterset and the chain of 16 lakes here in Winter Haven! Legoland is also accessible by boat on Lake Eloise! It also boasts advanced features like tray and coffered ceilings, custom window & door

    Agent Photo

    Alexis Bress

    EXP REALTY LLC

    (863) 208-9214

    2682 Wyndsor Oaks Place, Winter Haven, FL 33884
  • /41

    $647,500

    • 4 Beds
    • 2 Baths
    • 2,736 Sq Ft

    710 Heritage Dr NE, Winter Haven, FL 33881

    Dreamy Updated Pool Home in Sought-After Hamilton Pointe! Welcome to your own private paradise in the heart of the well-established Hamilton Pointe neighborhood! This stunning 4-bedroom, 2-bathroom pool home sits on nearly half an acre of beautifully landscaped land, surrounded by mature trees that provide peace and charm.Step inside to discover a fully updated interior featuring

    Jill Lingenfelter CENTURY 21 MYERS REALTY

    710 Heritage Dr NE, Winter Haven, FL 33881
  • /43

    $725,000

    • 4 Beds
    • 2.5 Baths
    • 2,643 Sq Ft

    475 Archaic Dr, Winter Haven, FL 33880

    Welcome to your perfect sanctuary in the heart of Central Florida! With a freshly repainted exterior, this one-level home offers rare and breathtaking lake views and is ideally located in a desirable cul-de-sac. With 4 spacious bedrooms, 2.5 bathrooms, and an impressive range of high-end upgrades, this residence seamlessly combines comfort, style, and convenience. Upon entering, you’ll

    David Small KELLER WILLIAMS REALTY SMART 1

    475 Archaic Dr, Winter Haven, FL 33880
  • /73

    $770,000

    • 4 Beds
    • 2.5 Baths
    • 2,001 Sq Ft

    10 Webb Rd, Winter Haven, FL 33881

    Secluded 4-Bedroom Ranch on 5 Acres with Pool, Barns & Country Charm! Discover the perfect blend of privacy, convenience, and space with this 4 bedroom, 2.5 bath ranch-style home nestled on 5 acres in East Winter Haven. Tucked away at the end of a quiet road, this former citrus grove offers a peaceful, no-HOA lifestyle with plenty of room for your family, animals, and hobbies. Built in 1979, the

    Martin E Higgenbotham HIGGENBOTHAM AUCTIONEERS INTERNATIONAL LTD INC

    10 Webb Rd, Winter Haven, FL 33881
  • /59

    $649,900

    • 4 Beds
    • 3 Baths
    • 2,633 Sq Ft

    333 Lake Otis Dr SE, Winter Haven, FL 33880

    Welcome to this beautifully renovated pool home offering modern luxury, privacy, and ultimate functionality all with no HOA restrictions! Situated on a spacious corner lot, this 3-bedroom, 3-bath residence includes a dedicated office perfect for working from home or a 4th guest room. Inside, you'll find a brand-new designer kitchen with premium cabinetry, solid countertops, and stainless-steel

    Colin Wells SIGNATURE PROPERTIES OF CENTRAL FLORIDA LLC

    333 Lake Otis Dr SE, Winter Haven, FL 33880
  • /46

    $600,000

    • 4 Beds
    • 2.5 Baths
    • 2,640 Sq Ft

    3991 Island Lakes Dr, Winter Haven, FL 33881

    Welcome to your personal lakeside retreat! This stunning two-story home offers 4 spacious bedrooms, 2.5 bathrooms, and a versatile loft — perfect for a home office, game room, or creative space. Nestled in the Island Lakes, enjoy sweeping water views from your own backyard paradise, complete with a private dock for boating, fishing, or simply soaking in the sunsets.Step inside to an

    Laura Medina Ruiz RE/MAX HERITAGE PROFESSIONALS

    3991 Island Lakes Dr, Winter Haven, FL 33881
  • /74

    $544,900

    • 4 Beds
    • 3 Baths
    • 2,550 Sq Ft

    1 Lake Eloise Ln, Winter Haven, FL 33884

    Don't miss out on this amazing 4/3 single-family home with a pool near Lake Eloise in winter Haven! This remarkable home features a newer roof, HVAC, Water heater, Pool screen enclosure, pool pump, Flooring, Cabinets, Paint, Pool Solar, Granite counter tops, Walk in shower, Pool Maricte, Pool deck coating, Garage epoxy floor, resurfaced showers and more. This home sits on a well-manicured lot

    John Carter KELLER WILLIAMS REALTY SMART

    1 Lake Eloise Ln, Winter Haven, FL 33884
  • /55

    $549,900

    • 4 Beds
    • 3 Baths
    • 3,257 Sq Ft

    19 Meadowlake Ct, Winter Haven, FL 33884

    New Price Reduction - Priced to Sell! Step into luxury with this stunning ranch-style home in the gated Cypresswood golf community! Nestled on a peaceful cul-de-sac, this spacious 4-bedroom home blends modern elegance with timeless charm, making it the perfect retreat.Inside, wood-look tile flooring flows throughout the main living areas, offering both durability and style. The gourmet kitchen is

    Rebecca Redman Hamaoui REAL BROKER, LLC

    19 Meadowlake Ct, Winter Haven, FL 33884
  • /32

    $589,000

    • 4 Beds
    • 3 Baths
    • 3,058 Sq Ft

    952 N Heron Cir, Winter Haven, FL 33884

    PRICE REDUCED $61,000!!**Stunning Lakefront Home with Private Views, Pool, and Outdoor Living Spaces - Nestled in a serene lakeside setting, this beautiful home offers breathtaking, private lake views that create the perfect backdrop for everyday living. Featuring a spacious, well-designed layout, the home boasts 4 bedrooms and 3 bathrooms, with high ceilings and a cozy fireplace in the living

    Krystal Maddox DALTON WADE INC

    952 N Heron Cir, Winter Haven, FL 33884
  • /17

    $490,000

    • 4 Beds
    • 3 Baths
    • 2,733 Sq Ft

    4338 Thomas Wood Ln E, Winter Haven, FL 33880

    This dreamy 4 bedroom 3 bath pool home with ease to the Polk Parkway is waiting for your family. This 2,733 SqFt home is so spacious and ready for you to move in. The kitchen in home features all major stainless appliances and wine fridge, formal dining and living area, family room with gas fireplace, Three large bedrooms upstairs, and a master closet that will make you have to buy more clothes.

    Ruth Morales EBENEZER REAL ESTATE SOLUTIONS GROUP LLC

    4338 Thomas Wood Ln E, Winter Haven, FL 33880
  • /63

    $450,000

    • 4 Beds
    • 2.5 Baths
    • 2,434 Sq Ft

    5009 Strada Dr, Winter Haven, FL 33880

    Welcome to this well-maintained Winter Haven pool home, offering over 2,400 sq ft of living space on a corner lot. This 4-bedroom, 2.5-bathroom home includes a 3-car garage, wood floors in the kitchen, foyer, and dining room, and spacious rooms with generous closet space. Upstairs, a cozy loft provides the perfect spot to unwind.Step outside to a screened and heated inground pool and spa,

    Florentino Beltran KELLER WILLIAMS ADVANTAGE 2 REALTY

    5009 Strada Dr, Winter Haven, FL 33880
  • /49

    $450,000

    • 4 Beds
    • 3 Baths
    • 2,542 Sq Ft

    7352 Bent Grass Dr, Winter Haven, FL 33884

    Welcome home! Step into this stunning 4 bedroom, 3 bathroom home located in the desirable Miller's Landing community of Winter Haven, Florida. Boasting 2,542 sq ft of meticulously maintained living space, this residence offers the perfect blend of inside comfort and an outdoor oasis. As you enter, you'll be greeted with abundance of natural light throughout and high ceilings. The kitchen is the

    Mark Berdelle REAL BROKER, LLC

    7352 Bent Grass Dr, Winter Haven, FL 33884
  • /37

    $460,000

    • 4 Beds
    • 3 Baths
    • 2,667 Sq Ft

    351 Greenfield Rd, Winter Haven, FL 33884

    SPACE FOR EVERYONE! COUNTRY CLUB LIFESTYLE!! Huge four bedroom, three full bath POOL home on .52 acres! Lot overlooks the 13th tee in the private, guard-gated 24/7 golf community of Cypresswood Golf & Country Club. Beautiful brick wood-burning fireplace in family room plus a large bonus room that was being used as a game and theater room - a great spot!! The kitchen features quartz countertops

    Catherine Kluytenaar THE K TEAM REAL ESTATE SERVICES LLC

    351 Greenfield Rd, Winter Haven, FL 33884
  • /55

    $450,000

    • 4 Beds
    • 3 Baths
    • 2,067 Sq Ft

    4812 Mandolin Ct, Winter Haven, FL 33884

    Welcome to this stunning 4-bedroom, 3-bathroom home with a dedicated office and a sparkling inground saltwater pool, nestled in the gated community of Mandolin. From the moment you step inside, you’ll appreciate the seamless flow of laminate flooring throughout—offering a clean, carpet-free living experience. The heart of the home is the spacious, open-concept kitchen, featuring stone

    John Hubbert, Jr BHHS FLORIDA PROPERTIES GROUP

    4812 Mandolin Ct, Winter Haven, FL 33884
  • /47

    $2,600,000

    • 4 Beds
    • 4.5 Baths
    • 5,178 Sq Ft

    950 N Lake Otis Dr SE, Winter Haven, FL 33880

    There was a time when homes were designed to last—and this is one of them. Designed by award-winning architect Gene Leedy, this south-facing lakefront residence embodies a legacy of modernism uniquely attuned to Florida’s landscape and climate. As a founding voice of the Sarasota School of Architecture, Leedy’s vision was ahead of its time, helping to shape a movement that left its mark on

    Ashley Marbet COMPASS FLORIDA LLC

    950 N Lake Otis Dr SE, Winter Haven, FL 33880
  • /42

    $318,000

    • 4 Beds
    • 2 Baths
    • 1,750 Sq Ft

    3917 Warbler Dr, Winter Haven, FL 33880

    Welcome Home to Queens Cove!This stunning 4 bedroom, 2 bathroom home is located in the highly desirable community of Queens Cove in Winter Haven, FL. With a spacious open-concept layout, this home offers the perfect balance of comfort, style, and functionality.Step inside to find a bright and airy living space with a seamless flow from the living room to the kitchen and dining area

    Eli Medina LIVE FLORIDA REALTY

    3917 Warbler Dr, Winter Haven, FL 33880
  • /35

    $485,000

    • 4 Beds
    • 3 Baths
    • 2,569 Sq Ft

    305 Hernando Rd, Winter Haven, FL 33884

    Welcome to your Dream home!! Step into this stunning residence through a spacious, light-filled foyer and prepare to be impressed by the thoughtfully, well maintained designed layout and exceptional features throughout. This home offers oversized bedrooms and a versatile bonus room—perfect for a game room, home office, or even a private in-law suite. This home has a formal living area, family

    Sherry Sapp COLDWELL BANKER REALTY

    305 Hernando Rd, Winter Haven, FL 33884
  • /19

    $390,000

    • 4 Beds
    • 3 Baths
    • 1,743 Sq Ft

    904 15th St NE, Winter Haven, FL 33881

    WELCOME TO YOUR NEXT GEN TURN KEY HOME. This MULTI FAMILY USE home sits in the beautiful town of Winter Haven. Just a few minutes from Lake Elbert, restaurants, stores, Downtown Winter Haven & 4 minutes from Polk College. This home will draw you in from the moment you enter it with its beautiful open space and high ceiling. It's modern kitchen with marble countertop and new appliances will

    Liz Polo LPT REALTY, LLC

    904 15th St NE, Winter Haven, FL 33881
  • /39

    $400,000

    • 4 Beds
    • 3.5 Baths
    • 2,194 Sq Ft

    1317 Avenue A SE, Winter Haven, FL 33880

    Welcome to 1317 Avenue A SE in Winter Haven, FL – A truly one-of-a-kind! This 4-bedroom, 3.5-bath home (including an en suite) is overflowing with charm, character, and endless potential! Step into your private outdoor oasis featuring an inviting inground pool and a spacious screened-in porch—perfect for relaxing, entertaining, or enjoying your morning coffee in comfort.Inside, the home

    Don Jerue KELLER WILLIAMS REALTY SMART 1

    1317 Avenue A SE, Winter Haven, FL 33880
  • /27

    $440,000

    • 4 Beds
    • 3 Baths
    • 2,420 Sq Ft

    415 Smiley Ct, Winter Haven, FL 33884

    3 spacious bedrooms + 1 versatile study/office??? Large great room with excellent natural light??? Open kitchen integrated into the dining room, ideal for family sharing?? 3 full bathrooms: ?? Covered garage for 3 vehicles?? Large private pool with terrace area for outdoor enjoyment?? Large side garden, perfect for games, pets, or

    Adriana Sanchez AGENT TRUST REALTY CORPORATION

    415 Smiley Ct, Winter Haven, FL 33884
  • /35

    $379,900

    • 4 Beds
    • 2 Baths
    • 1,977 Sq Ft

    111 Beverly Dr, Winter Haven, FL 33884

    Perfect 4 Bed / 2 Bath Pool Home for entertaining! Don’t miss this beautifully maintained 4-bedroom, 2-bath split-plan home featuring the sought-after John Wood floor plan. Enjoy Florida living with a large screened-in pool and an oversized lanai, perfect for entertaining or relaxing outdoors. Recent updates include * remodeled kitchen and baths with Granite Counter-tops * a 7-year-old roof *

    Barry Macchione REMAX EXPERTS

    111 Beverly Dr, Winter Haven, FL 33884
  • /47

    $425,000

    • 4 Beds
    • 2 Baths
    • 2,069 Sq Ft

    114 Belmont Dr, Winter Haven, FL 33884

    Welcome to this spacious and beautifully designed pool home, perfect for entertaining and family living! As you step through the front door, you’re welcomed by a tiled foyer leading to a formal dining room with elegant wood laminate flooring and a cozy den that overlooks the pool area.The kitchen features tile flooring, a gas stove, abundant cabinetry, and a farmhouse sink with views of the

    Stacey Towns STACEY TOWNS REALTY LLC

    114 Belmont Dr, Winter Haven, FL 33884
  • /49

    $495,000

    • 4 Beds
    • 2 Baths
    • 2,172 Sq Ft

    413 Ruby Lake Place, Winter Haven, FL 33884

    Welcome to this beautifully maintained saltwater pool home offering comfort, style, and a prime location! Brickwork entry leads into an open foyer with tile flooring. The formal living and dining areas provide a picture-perfect view of the sparkling saltwater pool with a soothing fountain. The kitchen features granite countertops, stainless steel appliances, ample cabinet space, and flows into a

    Stacey Towns STACEY TOWNS REALTY LLC

    413 Ruby Lake Place, Winter Haven, FL 33884
  • /62

    $849,900

    • 4 Beds
    • 3 Baths
    • 3,020 Sq Ft

    1 Brogden Ct SE, Winter Haven, FL 33880

    Custom-Built by Hulbert Homes! Known for their exceptional quality and craftsmanship, Hulbert Homes delivers again with this thoughtfully designed home. From the custom mahogany double doors to the luxury vinyl flooring throughout, every detail has been carefully considered. This 4-bedroom, 3-bath home is filled with natural light and features high ceilings, crown moulding, and a spacious

    Brian Stephens EXP REALTY LLC

    1 Brogden Ct SE, Winter Haven, FL 33880
  • /54

    $444,900 Open Sat 10AM - 12PM

    • 4 Beds
    • 4 Baths
    • 3,586 Sq Ft

    16 Golfview Cir NE, Winter Haven, FL 33881

    Large and lovely two story mid-century pool home in the heart of Winter Haven/North Lake Elbert Heights, near Polk State College, Lake Elbert, the Diamondplex Sports Complex, and beautiful, exciting, and vibrant downtown! Enter the foyer to the living room and formal dining room with newer wood floors throughout and plenty of space for dinner parties and family time. The bright chef's kitchen has

    Natalie Oldenkamp BHHS FLORIDA PROPERTIES GROUP

    16 Golfview Cir NE, Winter Haven, FL 33881
  • /89

    $625,000

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

    255 Lake Link Rd, Winter Haven, FL 33884

    Welcome to your dream retreat on the shimmering shores of Lake Link in beautiful Winter Haven, Florida offering a 2-year paid Home Warranty! This stunning 4-bedroom, 3-bathroom lakefront home is a true tropical paradise, combining luxury, comfort, and functionality in a setting that feels like a private resort. Step inside and immediately feel the serenity of your completely upgraded oasis.

    Michele Elchin DALTON WADE INC

    255 Lake Link Rd, Winter Haven, FL 33884
  • /69

    $599,000

    • 4 Beds
    • 3 Baths
    • 3,225 Sq Ft

    3805 Gaines Dr, Winter Haven, FL 33884

    Seller motivated and will review all offers! Welcome to this stunning 4-bedroom, 3-bathroom ranch-style home located in the highly sought-after neighborhood of Winter Haven!Offering over 3,000 sq ft of living space, this property boasts spacious rooms and a bright, open layout — perfect for both everydayliving and entertaining. Highlights include ranch-style architecture, a beautiful

    Jody Pagan PAIGE WAGNER HOMES REALTY

    3805 Gaines Dr, Winter Haven, FL 33884
  • /28

    $849,900

    • 4 Beds
    • 2.5 Baths
    • 2,844 Sq Ft

    1002 Lake Elbert Dr SE, Winter Haven, FL 33880

    LAKE/POOL HOME with 160' of Lake Elbert Frontage! This beautiful brick residence offers resort-style living right at your doorstep with a private sandy beach or if you’re an avid boater, look to build your own boat dock! Other days relax in the back yard within your screened area and enjoy your heated pool with attached spa (new heater and chlorinator in 2024). Inside, this 4-bedroom, 2.5-bath

    Kevin Giguere EPIQUE REALTY, INC.

    1002 Lake Elbert Dr SE, Winter Haven, FL 33880
  • /76

    $499,000

    • 4 Beds
    • 2 Baths
    • 3,198 Sq Ft

    934 Lake Elbert Dr SE, Winter Haven, FL 33880

    Welcome to a one-of-a-kind lakeside retreat in the heart of Winter Haven — a beautifully preserved 1926 residence set on over half an acre of direct lakefront property along the serene shores of Lake Elbert. With more than 3,100 square feet of versatile living space, this property blends historic charm with modern flexibility for multigenerational households, remote work, or

    Chris Renfro KELLER WILLIAMS REALTY SMART

    934 Lake Elbert Dr SE, Winter Haven, FL 33880
  • /39

    $458,000

    • 4 Beds
    • 3 Baths
    • 2,433 Sq Ft

    212 Terranova Blvd, Winter Haven, FL 33884

    100% FINANCING AVAILABLE – NO PMI AND NO INCOME LIMIT – MAKING THIS HOME THE BEST OPTION FOR YOU AND YOUR FAMILY! This elegant and impeccably maintained 4-bedroom, 3-bath former model home with a solar-heated pool is located in a beautiful gated community and offers stunning conservation views. Used only as a second residence, it features a spacious layout with soaring ceilings, wood floors,

    Valerie Casals INVESTOR'S REAL ESTATE LLC

    212 Terranova Blvd, Winter Haven, FL 33884
  • /65

    $3,495,000

    • 4 Beds
    • 4 Baths
    • 3,659 Sq Ft

    180 Brigham Rd NW, Winter Haven, FL 33881

    PRICE ADJUSTMENT | NOW OFFERED UNDER APPRAISED VALUE ~ Click on the virtual tour link for a tour of the property. No HOA and conveniently between Tampa and Orlando, and away from the risks of hurricanes, surging waters and heavy traffic, experience this one-of-a-kind, privately gated estate in the heart of Central Florida, a contemporary masterpiece, embracing designs and element concepts from

    Louise Richer PREMIER SOTHEBY'S INTL. REALTY

    180 Brigham Rd NW, Winter Haven, FL 33881
  • /34

    $475,000

    • 4 Beds
    • 3 Baths
    • 2,663 Sq Ft

    148 Lake Otis Rd, Winter Haven, FL 33884

    Spacious 4-Bedroom, 3-Bath Pool Home in the admired Lakewood Community. Nestled on an oversized lot with mature trees, this remodeled tri-level home offers a perfect blend of modern luxury and comfort. With a spacious layout, a private pool, and an abundance of natural light, this home is designed for both relaxation and entertaining. As you enter, you’ll immediately notice the bright and airy

    Michelle Armbruster LOCKHART & ASSOCIATES INC

    148 Lake Otis Rd, Winter Haven, FL 33884
  • /25

    $465,000

    • 4 Beds
    • 2 Baths
    • 2,367 Sq Ft

    415 Ruby Lake Place, Winter Haven, FL 33884

    This home sounds like an amazing opportunity! Located in the gated and upscale Ruby Lake community, it offers a fantastic combination of convenience and luxury. With its beautiful 4 bedrooms and 2 bathrooms, it’s spacious enough for both family and guests, and the fresh updates like a new roof, AC, water heater, and freshly painted pool deck give it a move-in-ready feel. The stamped concrete

    Susan Brown COLDWELL BANKER REALTY

    415 Ruby Lake Place, Winter Haven, FL 33884
  • /21

    $335,000

    • 4 Beds
    • 2 Baths
    • 1,672 Sq Ft

    1610 Meadow Ln NE, Winter Haven, FL 33881

    Beautifully Remodeled 4 Bedroom, 2 Bathroom Home with NO HOA! Welcome to your dream home! This home features an open concept living, dining, and kitchen area with a spacious island and breakfast bar. The kitchen is a chef's delight, boasting stainless steel appliances, granite countertops, a gorgeous backsplash, and an oversized island perfect for seating and multiple cooks. This home has been

    Eric Chastain THE STONES REAL ESTATE FIRM

    1610 Meadow Ln NE, Winter Haven, FL 33881
  • /42

    $749,000

    • 4 Beds
    • 3 Baths
    • 3,790 Sq Ft

    2418 Berkshire Dr, Winter Haven, FL 33884

    Executive custom built home offered for the first time since it was built in 1991. As you enter through the upscale Eloise Pointe Estates community gated entrance and proceed to the largest corner lot (.75 acres) in the quaint established neighborhood you'll be greeted on the circular driveway and ushered past lush mature landscaping to the stately double door entry. Upon entering the large foyer

    Scott Kline KLINE REAL ESTATE SERVICES

    2418 Berkshire Dr, Winter Haven, FL 33884
  • /66

    $775,000

    • 4 Beds
    • 2.5 Baths
    • 2,001 Sq Ft

    10 Webb Rd, Winter Haven, FL 33881

    Auction Property. AUCTION! 10AM, Saturday, Sept. 13th.Secluded 4-Bedroom Ranch on 5 Acres with Pool, Barns & Country Charm!Discover the perfect blend of privacy, convenience, and space with this 4 bedroom, 2.5 bath ranch-style home nestled on 5 acres in East Winter Haven. Tucked away at the end of a quiet road, this former citrus grove offers a peaceful, no-HOA lifestyle with plenty

    Angie Poole HIGGENBOTHAM AUCTIONEERS

    10 Webb Rd, Winter Haven, FL 33881

Home Trends in Winter Haven, FL

Housing Trends

Median Sale Price
$299,200
Median Single Family Sale Price
$305,490
Median Townhouse Sale Price
$259,900
Median 2 Bedroom Sale Price
$135,000
Median 1 Bedroom Sale Price
$108,000
Average Price Per Sq Ft
$166
Number of Homes for Sale
150
Last 12 months Home Sales
1,070
Months of Supply
1.70
Median List Price
$324,825
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
-6%
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