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Ready to love where you live? This beautifully maintained 4-bedroom, 3.5-bath home in prestigious Cedar Creek offers the space, updates, and comfort you’ve been looking for. Conveniently located in a cul de sac with a large yard. Step inside to gorgeous hardwood floors and an inviting open floor plan designed for both everyday living and entertaining. The spacious kitchen features solid-surface countertops, a prep island, and plenty of storage, while the living room’s gas-log fireplace with built-ins creates the perfect spot to relax. The beautiful primary suite offers a private retreat with a soaking tub and walk-in shower. Three additional bedrooms provide plenty of room for family, guests, or a home office. The walk-out lower level adds valuable living space with a family room and full bath. Outside, enjoy the composite deck, lower level patio, and a beautifully maintained lawn with a sprinkler system. Beautifully cared for and move-in ready, this Cedar Creek home checks all the boxes. Taxes will be substantially lower with Homestead Exemption.

4 Beds ⋅ 4 Baths ⋅ 202641153 MLS ⋅ 3,006 SqFt. ⋅ Laurie Ladow

Ready to love where you live? This beautifully maintained 4-bedroom, 3.5-bath home in prestigious Cedar Creek offers the space, updates, and comfort you’ve been looking for. Conveniently located in a cul de sac with a large yard. Step inside to gorgeous hardwood floors and an inviting open floor plan designed for both everyday living and entertaining. The spacious kitchen features solid-surface countertops, a prep island, and plenty of storage, while the living room’s gas-log fireplace with built-ins creates the perfect spot to relax. The beautiful primary suite offers a private retreat with a soaking tub and walk-in shower. Three additional bedrooms provide plenty of room for family, guests, or a home office. The walk-out lower level adds valuable living space with a family room and full bath. Outside, enjoy the composite deck, lower level patio, and a beautifully maintained lawn with a sprinkler system. Beautifully cared for and move-in ready, this Cedar Creek home checks all the boxes. Taxes will be substantially lower with Homestead Exemption.

13086 Bear Creek Ct, Middlebury

Listing courtesy of Laurie Ladow from Cressy & Everett - South Bend. Cell: 574-532-8779

$434,900

Sprawling ranch in the highly sought-after Highland Hills neighborhood in Middlebury Schools! This 3-bedroom, 2.5-bath home has over 3,300 finished square feet with an open layout, spacious living areas, a cozy fireplace and spacious fenced-in backyard with patio. It features solid hardwood floors, a stunning primary suite with walk-in closet, and main-level laundry. The partially finished basement provides additional living space and tons of potential with an additional 1,500+ unfinished square feet. Recent updates include brand new HVAC furnace and central A/C (2026) new roof (2022), stainless steel appliances (2022), reverse osmosis water filtration system, and many other recent upgrades throughout.

3 Beds ⋅ 3 Baths ⋅ 202622750 MLS ⋅ 3,304 SqFt. ⋅ Andrew Myers

Sprawling ranch in the highly sought-after Highland Hills neighborhood in Middlebury Schools! This 3-bedroom, 2.5-bath home has over 3,300 finished square feet with an open layout, spacious living areas, a cozy fireplace and spacious fenced-in backyard with patio. It features solid hardwood floors, a stunning primary suite with walk-in closet, and main-level laundry. The partially finished basement provides additional living space and tons of potential with an additional 1,500+ unfinished square feet. Recent updates include brand new HVAC furnace and central A/C (2026) new roof (2022), stainless steel appliances (2022), reverse osmosis water filtration system, and many other recent upgrades throughout.

115 Greenfield Dr, Middlebury

Listing courtesy of Andrew Myers from Myers Trust Real Estate. Office: 574-875-5149

$649,900

Built by Town & Country Builders, this beautiful home offers timeless quality in one of the area's most sought-after neighborhoods. Set on a private, wooded lot within walking distance to parks and the Pumpkin Vine Trail. Four bedrooms each include a private bath, plus a bonus room ideal as a 5th bedroom, for a total of 3.5 bathrooms. Hand-scraped hardwood floors and granite kitchen countertops add warmth and quality throughout. The lower level includes a hot tub connection on the patio access, plus rough-in plumbing for a fourth full bathroom. Enjoy outdoor living on the screened porch overlooking the backyard, complete with a natural gas grill hookup. A spacious 3 car attached garage completes the package, along with a roof installed just three years ago. Don't miss your opportunity to call this exceptional Highland Woods property home!

4 Beds ⋅ 4 Baths ⋅ 202636820 MLS ⋅ 3,841 SqFt. ⋅ Steve Miller

Built by Town & Country Builders, this beautiful home offers timeless quality in one of the area's most sought-after neighborhoods. Set on a private, wooded lot within walking distance to parks and the Pumpkin Vine Trail. Four bedrooms each include a private bath, plus a bonus room ideal as a 5th bedroom, for a total of 3.5 bathrooms. Hand-scraped hardwood floors and granite kitchen countertops add warmth and quality throughout. The lower level includes a hot tub connection on the patio access, plus rough-in plumbing for a fourth full bathroom. Enjoy outdoor living on the screened porch overlooking the backyard, complete with a natural gas grill hookup. A spacious 3 car attached garage completes the package, along with a roof installed just three years ago. Don't miss your opportunity to call this exceptional Highland Woods property home!

211 Greenfield Dr, Middlebury

Listing courtesy of Steve Miller from RE/MAX Results. Office: 574-533-9581

$615,000

Beautifully remodeled home offers an impressive combination of modern updates, spacious living areas, and luxurious amenities. Featuring two large living rooms, there is plenty of space to entertain, relax, or create a dedicated family and gathering area. The remodeled kitchen provides a fresh, updated space for preparing meals and entertaining, while the fireplace adds warmth and character to the home. The finished basement offers additional versatile living space that can be used as a recreation room, gym, media room, or whatever best fits your needs. The home's luxury features continue with a steam shower, heated bathroom floors, and built-in sauna, creating a private spa-like experience. Step outside to enjoy the backyard and its beautiful water feature, adding a peaceful focal point to the outdoor space. With extensive remodeling, generous living areas, a finished basement, and exceptional amenities, this Middlebury property is ready to welcome its next owner. Buyer to verify tax's, square footage, room sizes and schools

4 Beds ⋅ 3 Baths ⋅ 202633095 MLS ⋅ 3,575 SqFt. ⋅ Cyle Jaskolka

Beautifully remodeled home offers an impressive combination of modern updates, spacious living areas, and luxurious amenities. Featuring two large living rooms, there is plenty of space to entertain, relax, or create a dedicated family and gathering area. The remodeled kitchen provides a fresh, updated space for preparing meals and entertaining, while the fireplace adds warmth and character to the home. The finished basement offers additional versatile living space that can be used as a recreation room, gym, media room, or whatever best fits your needs. The home's luxury features continue with a steam shower, heated bathroom floors, and built-in sauna, creating a private spa-like experience. Step outside to enjoy the backyard and its beautiful water feature, adding a peaceful focal point to the outdoor space. With extensive remodeling, generous living areas, a finished basement, and exceptional amenities, this Middlebury property is ready to welcome its next owner. Buyer to verify tax's, square footage, room sizes and schools

55755 Little Creek Ln, Middlebury

Listing courtesy of Cyle Jaskolka from Realty Group Resources. Cell: 574-312-9718

$279,900

Welcome home to this beautifully maintained 3-bedroom, 2-bath home nestled on a quiet street in one of Middlebury’s desirable neighborhoods. Conveniently located near schools, this move-in-ready home offers the perfect combination of comfort, convenience, and future potential. Inside, you’ll find an inviting layout featuring a spacious primary suite, updated stainless steel appliances, and newer mechanicals for added peace of mind. The home has been professionally cleaned and is ready for its next owner to move right in.The full unfinished basement offers an incredible opportunity to nearly double your finished living space, providing endless possibilities for additional bedrooms, a recreation room, home office, or workout area. Whether you’re a first-time homebuyer, looking to downsize, or searching for a home with room to grow, this property checks all the boxes. Available for a quick closing with immediate possession, you can start enjoying your new home right away. Don’t miss this fantastic opportunity to own a move-in-ready home in the heart of Middlebury!

3 Beds ⋅ 2 Baths ⋅ 202631867 MLS ⋅ 1,176 SqFt. ⋅ Chantel Boone

Welcome home to this beautifully maintained 3-bedroom, 2-bath home nestled on a quiet street in one of Middlebury’s desirable neighborhoods. Conveniently located near schools, this move-in-ready home offers the perfect combination of comfort, convenience, and future potential. Inside, you’ll find an inviting layout featuring a spacious primary suite, updated stainless steel appliances, and newer mechanicals for added peace of mind. The home has been professionally cleaned and is ready for its next owner to move right in.The full unfinished basement offers an incredible opportunity to nearly double your finished living space, providing endless possibilities for additional bedrooms, a recreation room, home office, or workout area. Whether you’re a first-time homebuyer, looking to downsize, or searching for a home with room to grow, this property checks all the boxes. Available for a quick closing with immediate possession, you can start enjoying your new home right away. Don’t miss this fantastic opportunity to own a move-in-ready home in the heart of Middlebury!

606 Claudia Ln, Middlebury

Listing courtesy of Chantel Boone from RE/MAX Results. Cell: 574-202-4408

$199,900

Escape to the tranquility of country living with this 6-acre property in the sought-after Middlebury Community School District. Surrounded by open skies and rural charm, this land offers the perfect setting for your dream home, hobby farm, or private getaway. Enjoy the peace and quiet of the countryside while still being just a short drive from local conveniences.

202614096 MLS ⋅ Crystal Miller

Escape to the tranquility of country living with this 6-acre property in the sought-after Middlebury Community School District. Surrounded by open skies and rural charm, this land offers the perfect setting for your dream home, hobby farm, or private getaway. Enjoy the peace and quiet of the countryside while still being just a short drive from local conveniences.

V/L County Road 28 ***, Middlebury

Listing courtesy of Crystal Miller from RE/MAX Results. Cell: 574-607-7156

$299,900

Step back in time and bring your vision to life with one of Middlebury’s most recognizable historic homes—the Krider nursery family home. Originally built in 1890, this remarkable property showcases a beautiful blend of Second Empire and Italianate architecture while offering an incredible opportunity to complete the restoration of a true local landmark. Situated on approximately 1.5 acres, the home has already undergone extensive structural and mechanical improvements, including all new electrical, a new electrical panel, new gas, water, and electrical service lines, a new metal roof (2017), basement tuck-pointing and the exterior of home. Home offers original hardwood flooring. City water has already been run to the property and simply needs to be activated. Inside, you’ll find timeless character at every turn, including a spacious study, formal dining room, an expansive enclosed wraparound porch featuring a log fireplace, and original architectural details waiting to be showcased. The current kitchen plans are at the rear of the home, with plans already envisioned for a future addition that would include a pantry and main-level bedroom. Upstairs offers space for four bedrooms and space for 2 bathrooms, seller envisioned a jack and Jill for one. Upstairs has a loft area with built-in bookshelf. Original shutters for the windows remain stored in the attic, preserving even more of the home’s historic charm. Additional improvements include a restored carport and detached garage. Whether you’re dreaming of restoring a grand historic residence, creating a bed and breakfast, or owning one of Middlebury’s most iconic homes, the Krider House offers a rare opportunity to finish a remarkable restoration while honoring its rich history. Home is being sold in its current condition. Buyer to verify all measurements, zoning, intended use, and historical preservation requirements, if applicable.

4 Beds ⋅ 1 Baths ⋅ 202629465 MLS ⋅ 2,256 SqFt. ⋅ Jennea Schirr

Step back in time and bring your vision to life with one of Middlebury’s most recognizable historic homes—the Krider nursery family home. Originally built in 1890, this remarkable property showcases a beautiful blend of Second Empire and Italianate architecture while offering an incredible opportunity to complete the restoration of a true local landmark. Situated on approximately 1.5 acres, the home has already undergone extensive structural and mechanical improvements, including all new electrical, a new electrical panel, new gas, water, and electrical service lines, a new metal roof (2017), basement tuck-pointing and the exterior of home. Home offers original hardwood flooring. City water has already been run to the property and simply needs to be activated. Inside, you’ll find timeless character at every turn, including a spacious study, formal dining room, an expansive enclosed wraparound porch featuring a log fireplace, and original architectural details waiting to be showcased. The current kitchen plans are at the rear of the home, with plans already envisioned for a future addition that would include a pantry and main-level bedroom. Upstairs offers space for four bedrooms and space for 2 bathrooms, seller envisioned a jack and Jill for one. Upstairs has a loft area with built-in bookshelf. Original shutters for the windows remain stored in the attic, preserving even more of the home’s historic charm. Additional improvements include a restored carport and detached garage. Whether you’re dreaming of restoring a grand historic residence, creating a bed and breakfast, or owning one of Middlebury’s most iconic homes, the Krider House offers a rare opportunity to finish a remarkable restoration while honoring its rich history. Home is being sold in its current condition. Buyer to verify all measurements, zoning, intended use, and historical preservation requirements, if applicable.

313 Bristol Ave, Middlebury

Listing courtesy of Jennea Schirr from McKinnies Realty, LLC Elkhart. Cell: 574-215-9291

$399,000

Located in the heart of downtown in endearing Middlebury, the possibilities in this home are ENDLESS! The upper two levels were once a Bed & Breakfast, with 4 Bedrooms and 5 baths. The lower level has a separate entrance with entirely separate living quarters! The historic charm exudes in the two upper levels. Rich woodwork, a butlers pantry and the original fireplace provide character that is rare to find! The yard is spacious and backs up to the extremely popular Pumpkinvine Trail, great for walking and biking enthusiasts! This is a rare gem! Don't miss your chance to make it your own! *Property had water in the basement and has been professionally remedied. The flooring has been removed and the seller is offering a $3,000 flooring allowance with an acceptable offer.

4 Beds ⋅ 6 Baths ⋅ 202619303 MLS ⋅ 4,112 SqFt. ⋅ Jami Stamm

Located in the heart of downtown in endearing Middlebury, the possibilities in this home are ENDLESS! The upper two levels were once a Bed & Breakfast, with 4 Bedrooms and 5 baths. The lower level has a separate entrance with entirely separate living quarters! The historic charm exudes in the two upper levels. Rich woodwork, a butlers pantry and the original fireplace provide character that is rare to find! The yard is spacious and backs up to the extremely popular Pumpkinvine Trail, great for walking and biking enthusiasts! This is a rare gem! Don't miss your chance to make it your own! *Property had water in the basement and has been professionally remedied. The flooring has been removed and the seller is offering a $3,000 flooring allowance with an acceptable offer.

435 S Main St, Middlebury

Listing courtesy of Jami Stamm from Coldwell Banker Real Estate Group. Cell: 574-596-4868

$549,900

Brand-new construction featuring 4-5 Bedrooms, 3 Full Bathrooms, and a desirable split-bedroom floor plan. The open-concept living area offers plenty of room to gather, while the upstairs bonus space provides flexibility for a home office, recreation room, hobby area, or additional living space. The kitchen comes complete with a full appliance package, and additional upgrades include a water softener and on-demand hot water heater. Enjoy low-maintenance living with slab construction, plus a covered front porch and an oversized covered rear patio overlooking neighboring woods for a peaceful and private setting. Move-in ready with modern finishes throughout.

5 Beds ⋅ 3 Baths ⋅ 202621264 MLS ⋅ 2,584 SqFt. ⋅ Nicolas Wyse

Brand-new construction featuring 4-5 Bedrooms, 3 Full Bathrooms, and a desirable split-bedroom floor plan. The open-concept living area offers plenty of room to gather, while the upstairs bonus space provides flexibility for a home office, recreation room, hobby area, or additional living space. The kitchen comes complete with a full appliance package, and additional upgrades include a water softener and on-demand hot water heater. Enjoy low-maintenance living with slab construction, plus a covered front porch and an oversized covered rear patio overlooking neighboring woods for a peaceful and private setting. Move-in ready with modern finishes throughout.

13120 Bear Creek Ct, Middlebury

Listing courtesy of Nicolas Wyse from RE/MAX Results. Office: 574-533-9581

$1,200,000

Welcome to this extraordinary custom all-brick estate nestled in the heart of Middlebury's prestigious Highland Woods subdivision. Perched atop the area's rolling hills, this exceptional Town & Country-built residence offers more than 6,000 square feet of beautifully finished living space and has been completely transformed with over $800,000 in luxurious updates completed within the past two years. Step inside the stunning foyer and discover impeccable craftsmanship and designer finishes throughout. The inviting lodge-inspired family room features a striking stone fireplace, while the spectacular custom kitchen is a true showpiece with premium finishes, abundant storage, and a hidden butler's pantry. The adjoining buffet and beverage area makes entertaining effortless, whether hosting holidays in the formal dining room or enjoying casual meals in the bright breakfast area overlooking your private back yard. You will love the spacious mudroom/laundry room. The perfect "drop spot" for coats, or backpacks. The main-level den/office with gorgeous custom woodwork provides the perfect work-from-home space. Upstairs, the luxurious primary suite features dual walk-in closets and a spa-inspired bath with a soaking tub and oversized tiled shower. Three additional bedrooms include a Jack-and-Jill bath with a walk-in shower and a third full bath with tub. The lower level is designed for entertaining with a custom kitchen, stone accents, a spacious family room with a second fireplace, bar area, two additional bedrooms, a fourth full bath, and a stunning wine room where fireside entertaining is at your fingertips for game nights, gatherings, or relaxing with friends. Outside, enjoy a private backyard surrounded by mature trees and abundant wildlife, along with a newly constructed deck ideal for outdoor living and entertaining. Beyond its beautiful finishes, this home offers peace of mind with new roof, windows, updated mechanicals, and a heated three-car attached garage. Every detail has been thoughtfully updated, and nothing has been overlooked. This is a rare opportunity to own one of Middlebury's finest homes.

6 Beds ⋅ 6 Baths ⋅ 202629033 MLS ⋅ 6,412 SqFt. ⋅ Julie Thatcher

Welcome to this extraordinary custom all-brick estate nestled in the heart of Middlebury's prestigious Highland Woods subdivision. Perched atop the area's rolling hills, this exceptional Town & Country-built residence offers more than 6,000 square feet of beautifully finished living space and has been completely transformed with over $800,000 in luxurious updates completed within the past two years. Step inside the stunning foyer and discover impeccable craftsmanship and designer finishes throughout. The inviting lodge-inspired family room features a striking stone fireplace, while the spectacular custom kitchen is a true showpiece with premium finishes, abundant storage, and a hidden butler's pantry. The adjoining buffet and beverage area makes entertaining effortless, whether hosting holidays in the formal dining room or enjoying casual meals in the bright breakfast area overlooking your private back yard. You will love the spacious mudroom/laundry room. The perfect "drop spot" for coats, or backpacks. The main-level den/office with gorgeous custom woodwork provides the perfect work-from-home space. Upstairs, the luxurious primary suite features dual walk-in closets and a spa-inspired bath with a soaking tub and oversized tiled shower. Three additional bedrooms include a Jack-and-Jill bath with a walk-in shower and a third full bath with tub. The lower level is designed for entertaining with a custom kitchen, stone accents, a spacious family room with a second fireplace, bar area, two additional bedrooms, a fourth full bath, and a stunning wine room where fireside entertaining is at your fingertips for game nights, gatherings, or relaxing with friends. Outside, enjoy a private backyard surrounded by mature trees and abundant wildlife, along with a newly constructed deck ideal for outdoor living and entertaining. Beyond its beautiful finishes, this home offers peace of mind with new roof, windows, updated mechanicals, and a heated three-car attached garage. Every detail has been thoughtfully updated, and nothing has been overlooked. This is a rare opportunity to own one of Middlebury's finest homes.

205 Greenfield Dr, Middlebury

Listing courtesy of Julie Thatcher from Coldwell Banker Real Estate Group.

$695,000

Here's an opportunity to own a versatile country property featuring two homes, a barn, and approximately 3 acres of pasture in Middlebury! Ideal for multi-generational living, hobby farming, or income potential. The primary residence offers 4 bedrooms and 2 full baths, a spacious living room with wood-burning fireplace, and a walkout basement complete with kitchenette, den, and additional bedroom. Recent updates include a new roof in 2025. Additional features include a large laundry/washroom, mudroom with sink and closet, and two decks for outdoor enjoyment. The second home includes 4 bedrooms, 1 full bath, and in-floor heat throughout, providing comfortable living or rental potential. Property is well-equipped with energy-efficient systems, including 15 solar panels, 48V system with two 300 Ah batteries, a 16-kW diesel generator backup and natural gas boiler heat. The 48’ x 32’ barn (built in 2020) is ideal for livestock or equestrian use and features 4 box stalls, 5 tie stalls, wash bay, and tack room. The property includes 2 geothermal waterers, a garden shed, apple trees, and raspberry plants. A unique rural property with flexible use and excellent homesteading potential—don’t miss this opportunity! The main home is wired for electricity - seller is willing to restore to NIPSCO power with a good offer.

4 Beds ⋅ 2 Baths ⋅ 202618544 MLS ⋅ 3,052 SqFt. ⋅ Leon Kramer

Here's an opportunity to own a versatile country property featuring two homes, a barn, and approximately 3 acres of pasture in Middlebury! Ideal for multi-generational living, hobby farming, or income potential. The primary residence offers 4 bedrooms and 2 full baths, a spacious living room with wood-burning fireplace, and a walkout basement complete with kitchenette, den, and additional bedroom. Recent updates include a new roof in 2025. Additional features include a large laundry/washroom, mudroom with sink and closet, and two decks for outdoor enjoyment. The second home includes 4 bedrooms, 1 full bath, and in-floor heat throughout, providing comfortable living or rental potential. Property is well-equipped with energy-efficient systems, including 15 solar panels, 48V system with two 300 Ah batteries, a 16-kW diesel generator backup and natural gas boiler heat. The 48’ x 32’ barn (built in 2020) is ideal for livestock or equestrian use and features 4 box stalls, 5 tie stalls, wash bay, and tack room. The property includes 2 geothermal waterers, a garden shed, apple trees, and raspberry plants. A unique rural property with flexible use and excellent homesteading potential—don’t miss this opportunity! The main home is wired for electricity - seller is willing to restore to NIPSCO power with a good offer.

57051 County Road 33, Middlebury

Listing courtesy of Leon Kramer from Bright Star Real Estate Services LLC. office: 574-821-7653

$425,000

Imagine owning a charming home just steps from the heart of one of Northern Indiana's most beloved tourist destinations. Located on historic Main Street in the quaint town of Middlebury, this property offers the ideal setting for a short-term rental, boutique Airbnb, or weekend getaway. The home sits on the Pumpkinvine Nature Trail and is just minutes away from Shipshewana's famous flea market and auctions, the Essenhaus Inn & Restaurant, Amish countryside tours, and endless opportunities for shopping, dining, and outdoor recreation. Whether visitors are coming for a girls' weekend, cycling adventure, Amish country experience, or Notre Dame football weekend, this location places them in the center of it all. Picture cozy gathering spaces, 4 thoughtfully designed bedrooms, and charming outdoor areas where guests can unwind after a day of exploring. With Middlebury's year-round tourism and limited boutique lodging options, this property presents an exciting opportunity to generate income while owning a piece of one of Indiana's most picturesque small towns. Whether you're looking to expand your investment portfolio or create a destination property with lasting appeal, this property offers location, charm, and exceptional Airbnb potential in one of the Midwest's hidden gems. All with a bonus apartment that could be rented!

4 Beds ⋅ 5 Baths ⋅ 202629722 MLS ⋅ 4,112 SqFt. ⋅ Jami Stamm

Imagine owning a charming home just steps from the heart of one of Northern Indiana's most beloved tourist destinations. Located on historic Main Street in the quaint town of Middlebury, this property offers the ideal setting for a short-term rental, boutique Airbnb, or weekend getaway. The home sits on the Pumpkinvine Nature Trail and is just minutes away from Shipshewana's famous flea market and auctions, the Essenhaus Inn & Restaurant, Amish countryside tours, and endless opportunities for shopping, dining, and outdoor recreation. Whether visitors are coming for a girls' weekend, cycling adventure, Amish country experience, or Notre Dame football weekend, this location places them in the center of it all. Picture cozy gathering spaces, 4 thoughtfully designed bedrooms, and charming outdoor areas where guests can unwind after a day of exploring. With Middlebury's year-round tourism and limited boutique lodging options, this property presents an exciting opportunity to generate income while owning a piece of one of Indiana's most picturesque small towns. Whether you're looking to expand your investment portfolio or create a destination property with lasting appeal, this property offers location, charm, and exceptional Airbnb potential in one of the Midwest's hidden gems. All with a bonus apartment that could be rented!

435 S Main St, Middlebury

Listing courtesy of Jami Stamm from Coldwell Banker Real Estate Group. Cell: 574-596-4868

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How much is your home worth?