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Welcome to this enchanting 1940 Tudor cottage nestled in the heart of Lexington's highly sought-after Chevy Chase neighborhood! Full of timeless character and storybook charm, this 4-bedroom, 2.5-bath home offers the warmth and craftsmanship that make historic homes so special. Beautiful hardwood floors, charming architectural details, and a lovely sunroom add to the home's inviting personality. Step outside to discover a peaceful backyard retreat, where birds are frequent visitors and beautiful azaleas burst into color each spring. A detached two-car garage adds convenience to this charming property. The location is just as special as the home itself! Enjoy the walkability of Chevy Chase, with beloved local restaurants, shops, and downtown Lexington attractions just a stroll away. Lovingly cared for by generations, this home is ready for its next chapter and someone who will appreciate its history, charm, and endless potential.

4 Beds ⋅ 3 Baths ⋅ 26029311 MLS

Welcome to this enchanting 1940 Tudor cottage nestled in the heart of Lexington's highly sought-after Chevy Chase neighborhood! Full of timeless character and storybook charm, this 4-bedroom, 2.5-bath home offers the warmth and craftsmanship that make historic homes so special. Beautiful hardwood floors, charming architectural details, and a lovely sunroom add to the home's inviting personality. Step outside to discover a peaceful backyard retreat, where birds are frequent visitors and beautiful azaleas burst into color each spring. A detached two-car garage adds convenience to this charming property. The location is just as special as the home itself! Enjoy the walkability of Chevy Chase, with beloved local restaurants, shops, and downtown Lexington attractions just a stroll away. Lovingly cared for by generations, this home is ready for its next chapter and someone who will appreciate its history, charm, and endless potential.

220 Chenault Rd, Lexington

$1,150,000

Located on one of Chevy Chase's most established streets, this stone-façade fourplex offers spacious units, extensive capital improvements, and room for future value-add. Since 2020, nearly every major building system has been updated, including a new shingle roof (2020), flat roof (2025), updated electrical with five separately metered panels, individual central HVAC systems for all four units, PEX plumbing updates, and capped chimneys. Exterior improvements include rebuilt composite front balconies, new upper-level stairs, and a resurfaced parking lot with underground downspout drainage directed away from the foundation. The building consists of three spacious 1BR/1BA units of approximately 1,150 SF each and one 2BR/1BA unit of approximately 1,850 SF. Hardwood floors run throughout, and one of the 1BR units features a fully renovated kitchen and bathroom. The remaining three units offer an opportunity for interior updates, with all three 1BR floor plans providing space for a potential second bedroom. The unfinished lower level includes four private storage rooms and shared laundry facilities. All four units are leased, with lease expirations ranging from April through June 2027. The property offers 5,670 SF above grade, an additional 1,890 SF unfinished basement, and sits on a 0.22-acre R-3 zoned lot.

5 Beds ⋅ 4 Baths ⋅ 26029281 MLS

Located on one of Chevy Chase's most established streets, this stone-façade fourplex offers spacious units, extensive capital improvements, and room for future value-add. Since 2020, nearly every major building system has been updated, including a new shingle roof (2020), flat roof (2025), updated electrical with five separately metered panels, individual central HVAC systems for all four units, PEX plumbing updates, and capped chimneys. Exterior improvements include rebuilt composite front balconies, new upper-level stairs, and a resurfaced parking lot with underground downspout drainage directed away from the foundation. The building consists of three spacious 1BR/1BA units of approximately 1,150 SF each and one 2BR/1BA unit of approximately 1,850 SF. Hardwood floors run throughout, and one of the 1BR units features a fully renovated kitchen and bathroom. The remaining three units offer an opportunity for interior updates, with all three 1BR floor plans providing space for a potential second bedroom. The unfinished lower level includes four private storage rooms and shared laundry facilities. All four units are leased, with lease expirations ranging from April through June 2027. The property offers 5,670 SF above grade, an additional 1,890 SF unfinished basement, and sits on a 0.22-acre R-3 zoned lot.

1409 Fontaine Rd, Lexington

$999,990

**This property is under contract with contingency to sell and a 48 hour kickout clause.** Welcome home to 331 Ridgeway Road! Situated in the HEART of Chevy Chase around the corner from the Henry Clay Estate, this beautiful Colonial has been meticulously(!) maintained, extensively updated, and couldn't be more ready for its next owners to move right in. The main level was designed for entertaining and easy living, featuring a floor plan that effortlessly flows from a sitting room to formal dining room to the spacious living room and finally the stylish and well-appointed chef's kitchen. Enjoy preparing meals with a professional-grade double oven, cooktop, microwave drawer, gorgeous granite countertops and subway backsplash, and an abundance of cabinet and pantry storage. Hardwood floors gleam throughout the first floor, and a newly updated mudroom and guest bathroom complete the amenities there. Upstairs, you'll first find a fantastic landing for a reading nook or home office. The back of the home boasts an expansive primary suite with two separate closets, as well as a newly renovated ensuite bath with the walk-in shower of your dreams. Two secondary bedrooms are conveniently joined by a Jack-and-Jill bathroom, and the huge fourth upstairs bedroom could also be used as a bonus/flex space with endless possibilities. A third full bathroom, also recently updated, and a laundry room with new cabinetry round out the second floor. The basement is home to 628sqft of just-painted unfinished space-- perfect for a home gym or all the storage you could ever need. There's a secluded side patio adjacent to the kitchen for family cookouts, and the backyard also feels private with full fencing and mature trees surrounding you. A LONG list of recent updates include new HVAC systems in 2024, new windows in 2022, new water heater in 2024, a five year old roof, new LVP upstairs in 2024, and fresh paint throughout a couple weeks ago. Homes like this don't hit the market in Chevy Chase very often, especially ones of this size and with an attached two car garage. Schedule your private tour today!

4 Beds ⋅ 4 Baths ⋅ 26027761 MLS

**This property is under contract with contingency to sell and a 48 hour kickout clause.** Welcome home to 331 Ridgeway Road! Situated in the HEART of Chevy Chase around the corner from the Henry Clay Estate, this beautiful Colonial has been meticulously(!) maintained, extensively updated, and couldn't be more ready for its next owners to move right in. The main level was designed for entertaining and easy living, featuring a floor plan that effortlessly flows from a sitting room to formal dining room to the spacious living room and finally the stylish and well-appointed chef's kitchen. Enjoy preparing meals with a professional-grade double oven, cooktop, microwave drawer, gorgeous granite countertops and subway backsplash, and an abundance of cabinet and pantry storage. Hardwood floors gleam throughout the first floor, and a newly updated mudroom and guest bathroom complete the amenities there. Upstairs, you'll first find a fantastic landing for a reading nook or home office. The back of the home boasts an expansive primary suite with two separate closets, as well as a newly renovated ensuite bath with the walk-in shower of your dreams. Two secondary bedrooms are conveniently joined by a Jack-and-Jill bathroom, and the huge fourth upstairs bedroom could also be used as a bonus/flex space with endless possibilities. A third full bathroom, also recently updated, and a laundry room with new cabinetry round out the second floor. The basement is home to 628sqft of just-painted unfinished space-- perfect for a home gym or all the storage you could ever need. There's a secluded side patio adjacent to the kitchen for family cookouts, and the backyard also feels private with full fencing and mature trees surrounding you. A LONG list of recent updates include new HVAC systems in 2024, new windows in 2022, new water heater in 2024, a five year old roof, new LVP upstairs in 2024, and fresh paint throughout a couple weeks ago. Homes like this don't hit the market in Chevy Chase very often, especially ones of this size and with an attached two car garage. Schedule your private tour today!

331 Ridgeway Rd, Lexington

$1,100,000

Back on the market and offering a rare second chance to own one of Chevy Chase's standout homes! After purchasing this exceptional property, the current owners made the heartfelt decision to remain in their longtime home of 38 years—creating an unexpected opportunity for the buyer who missed it the first time. This beautifully renovated and expanded Chevy Chase residence blends timeless character with sophisticated modern living in one of Lexington's most sought-after locations. Enjoy the lifestyle buyers love about 40502—tree-lined streets, sidewalks, nearby parks, locally loved restaurants, and convenient access to downtown Lexington, the University of Kentucky, and the new Publix. Offering approximately 3,200 finished square feet, the home is filled with inviting spaces designed for both everyday living and effortless entertaining. Natural light highlights warm hardwood flooring, detailed millwork, and an open, flowing floor plan. The beautifully updated kitchen features Taj Mahal quartzite countertops and backsplash by CounterCulture, custom cabinetry, stainless-steel appliances, and a farmhouse sink, with an easy connection to the dining and living spaces. The main-level primary suite is a true retreat, with a custom Closets by Design walk-in closet and a spa-inspired bath featuring heated tile floors, dual vanities, a private water closet, and an oversized walk-in shower with multiple shower heads and body jets. A second main-level bedroom, currently used as a home office, showcases the original brick fireplace and a custom Murphy Door bookcase concealing the closet. Outdoor living is equally impressive. A vaulted screened porch with wood ceiling and stone fireplace overlooks the beautifully landscaped backyard, while the custom stone patio, fire pit and landscape lighting by Redmond's Landscaping create an exceptional setting for entertaining or relaxing outdoors. The finished basement provides additional flexible living space with custom built-ins and ceramic tile flooring. Additional improvements include custom blinds throughout by The Blinds Man, first-level interior paint completed in 2025, a driveway security gate by Overhead Door Company and basement waterproofing completed by Champion Waterproofing in 2021 with sump pump and transferable lifetime warranty. Rarely does a Chevy Chase home combine this level of architectural character, thoughtful renovation, modern functionality, and location. If you missed 403 Chinoe the first time, here's your chance.

4 Beds ⋅ 4 Baths ⋅ 26024493 MLS

Back on the market and offering a rare second chance to own one of Chevy Chase's standout homes! After purchasing this exceptional property, the current owners made the heartfelt decision to remain in their longtime home of 38 years—creating an unexpected opportunity for the buyer who missed it the first time. This beautifully renovated and expanded Chevy Chase residence blends timeless character with sophisticated modern living in one of Lexington's most sought-after locations. Enjoy the lifestyle buyers love about 40502—tree-lined streets, sidewalks, nearby parks, locally loved restaurants, and convenient access to downtown Lexington, the University of Kentucky, and the new Publix. Offering approximately 3,200 finished square feet, the home is filled with inviting spaces designed for both everyday living and effortless entertaining. Natural light highlights warm hardwood flooring, detailed millwork, and an open, flowing floor plan. The beautifully updated kitchen features Taj Mahal quartzite countertops and backsplash by CounterCulture, custom cabinetry, stainless-steel appliances, and a farmhouse sink, with an easy connection to the dining and living spaces. The main-level primary suite is a true retreat, with a custom Closets by Design walk-in closet and a spa-inspired bath featuring heated tile floors, dual vanities, a private water closet, and an oversized walk-in shower with multiple shower heads and body jets. A second main-level bedroom, currently used as a home office, showcases the original brick fireplace and a custom Murphy Door bookcase concealing the closet. Outdoor living is equally impressive. A vaulted screened porch with wood ceiling and stone fireplace overlooks the beautifully landscaped backyard, while the custom stone patio, fire pit and landscape lighting by Redmond's Landscaping create an exceptional setting for entertaining or relaxing outdoors. The finished basement provides additional flexible living space with custom built-ins and ceramic tile flooring. Additional improvements include custom blinds throughout by The Blinds Man, first-level interior paint completed in 2025, a driveway security gate by Overhead Door Company and basement waterproofing completed by Champion Waterproofing in 2021 with sump pump and transferable lifetime warranty. Rarely does a Chevy Chase home combine this level of architectural character, thoughtful renovation, modern functionality, and location. If you missed 403 Chinoe the first time, here's your chance.

403 Chinoe Rd, Lexington

$1,090,000

Set on one of Lexington's most beloved tree-lined streets in the coveted Chevy Chase / Ashland Park area, this 1935 Kentucky limestone Cotswold/Tudor home is a rare blend of storybook character and modern living. From the steeply pitched gables and stone chimney with terracotta chimney pots to the arched red front door and bluestone covered porch, the curb appeal is straight out of a storybook. Timeless and natural materials were chosen throughout to honor the home's original architecture while quietly delivering every modern convenience. Inside, graceful arched doorways and refinished hardwood floors set a warm, inviting tone. A completely renovated open-concept kitchen anchors the main level with custom cabinetry, granite countertops, limestone backsplash, a gas range, and a breakfast-bar peninsula that flows effortlessly into the dining and living spaces — with double pocket doors opening to a light-filled sunroom. A custom travertine-slab fireplace with a herringbone-tile firebox and gas insert serves as a stunning focal point. Original curved ceilings in two of the upstairs bedrooms — a signature of authentic Cotswold design — and distinctive staircase balusters are charming reminders of the home's 1935 pedigree. The 2005 two-story addition expanded the living space with Hardie board siding, solid-wood interior doors with crystal knobs, and a stone skirt around the foundation — some of it original stone reclaimed from the main home. Walls of French doors along the addition open to the backyard, filling the home with natural light and creating a seamless indoor-outdoor flow. Custom built-ins throughout, including a glass-front dining room hutch and a laundry room/pantry with granite and travertine, reflect the same craftsmanship found in every corner. The spa-like primary bath is a true retreat, featuring a freestanding clawfoot soaking tub, a long double vanity with marble countertop, custom cabinetry, a chandelier, penny-tile flooring, and a custom laundry chute. A second-floor secondary bath is equally refined with a new porcelain tile shower and floor, custom cabinetry, and marble countertops. The finished basement is a destination of its own: custom and reclaimed-wood shelving, a bar area with a beverage fridge, a cedar closet, generous storage, and durable LVP flooring — with the adjacent utility area proactively waterproofed to protect the finished space. Outdoors, a generous 17' x 29' patio topped with Pennsylvania bluestone — accessible through multiple sets of French doors — creates an elegant, private setting for entertaining. Out front, professional landscaping and mature trees and hydrangeas, a bluestone covered front porch and walkway, and laurel-stone edging. A rare extra-deep 22' x 26' detached garage with carriage-style doors, coordinating stone front and Hardie board siding was designed to blend seamlessly with the home, and even reuses windows from the original house. Behind its timeless facade, this home offers the best of both worlds: the irreplaceable character of a 1935 Chevy Chase original, paired with thoughtfully updated interiors that honor its heritage down to the smallest detail. Walkable to the shops and restaurants of Chevy Chase and just minutes from the University of Kentucky, downtown, and everything that makes this one of Lexington's most sought-after neighborhoods. Property being sold as is with inspections welcomed.

4 Beds ⋅ 3 Baths ⋅ 26021097 MLS

Set on one of Lexington's most beloved tree-lined streets in the coveted Chevy Chase / Ashland Park area, this 1935 Kentucky limestone Cotswold/Tudor home is a rare blend of storybook character and modern living. From the steeply pitched gables and stone chimney with terracotta chimney pots to the arched red front door and bluestone covered porch, the curb appeal is straight out of a storybook. Timeless and natural materials were chosen throughout to honor the home's original architecture while quietly delivering every modern convenience. Inside, graceful arched doorways and refinished hardwood floors set a warm, inviting tone. A completely renovated open-concept kitchen anchors the main level with custom cabinetry, granite countertops, limestone backsplash, a gas range, and a breakfast-bar peninsula that flows effortlessly into the dining and living spaces — with double pocket doors opening to a light-filled sunroom. A custom travertine-slab fireplace with a herringbone-tile firebox and gas insert serves as a stunning focal point. Original curved ceilings in two of the upstairs bedrooms — a signature of authentic Cotswold design — and distinctive staircase balusters are charming reminders of the home's 1935 pedigree. The 2005 two-story addition expanded the living space with Hardie board siding, solid-wood interior doors with crystal knobs, and a stone skirt around the foundation — some of it original stone reclaimed from the main home. Walls of French doors along the addition open to the backyard, filling the home with natural light and creating a seamless indoor-outdoor flow. Custom built-ins throughout, including a glass-front dining room hutch and a laundry room/pantry with granite and travertine, reflect the same craftsmanship found in every corner. The spa-like primary bath is a true retreat, featuring a freestanding clawfoot soaking tub, a long double vanity with marble countertop, custom cabinetry, a chandelier, penny-tile flooring, and a custom laundry chute. A second-floor secondary bath is equally refined with a new porcelain tile shower and floor, custom cabinetry, and marble countertops. The finished basement is a destination of its own: custom and reclaimed-wood shelving, a bar area with a beverage fridge, a cedar closet, generous storage, and durable LVP flooring — with the adjacent utility area proactively waterproofed to protect the finished space. Outdoors, a generous 17' x 29' patio topped with Pennsylvania bluestone — accessible through multiple sets of French doors — creates an elegant, private setting for entertaining. Out front, professional landscaping and mature trees and hydrangeas, a bluestone covered front porch and walkway, and laurel-stone edging. A rare extra-deep 22' x 26' detached garage with carriage-style doors, coordinating stone front and Hardie board siding was designed to blend seamlessly with the home, and even reuses windows from the original house. Behind its timeless facade, this home offers the best of both worlds: the irreplaceable character of a 1935 Chevy Chase original, paired with thoughtfully updated interiors that honor its heritage down to the smallest detail. Walkable to the shops and restaurants of Chevy Chase and just minutes from the University of Kentucky, downtown, and everything that makes this one of Lexington's most sought-after neighborhoods. Property being sold as is with inspections welcomed.

409 Dudley Rd, Lexington

$1,499,000

Truly one of a kind, this remarkable home seamlessly blends the timeless character of a historic stone cottage with the comfort and functionality of a thoughtfully renovated ranch home. Envisioned by its creative owners, the home offers 4,891 square feet of beautifully designed and exceptionally livable space, where historic charm and modern updates come together in a truly special setting. The open-concept main living area features a spacious Great Room with an inviting fireplace, a generous Dining Area, and an updated Kitchen complete with new cabinetry, appliances, and a charming built-in dinette with seating. A dramatic wall of windows fills the space with natural light and overlooks the expansive bluestone patio and pergola, peaceful lily pond, and picturesque views of the original stone cottage. The main level offers four Bedrooms, two with en suite full Baths, and an additional full Bath and half Bath. A light-filled hallway lined with large windows leads to a comfortable Family Room, Laundry Room, Utility Room, and Safe Room. The second floor is dedicated to an impressive Primary Suite featuring a fireplace, newly added full Bath, three large walk-in closets, an Exercise Room, and a private Office—creating a spacious and serene retreat. Extensive upgrades include a new metal roof, whole home generator, geothermal heating and cooling, structured wiring and camera system, and dual 100-gallon water heaters. Please see the numerous other updates on the attached list. Additional highlights include a spacious two-car attached Garage and generous attic storage. Rich in character, thoughtfully updated, and designed for everyday living and entertaining, this exceptional property offers a rare opportunity to own a home unlike any other.

5 Beds ⋅ 5 Baths ⋅ 26018503 MLS

Truly one of a kind, this remarkable home seamlessly blends the timeless character of a historic stone cottage with the comfort and functionality of a thoughtfully renovated ranch home. Envisioned by its creative owners, the home offers 4,891 square feet of beautifully designed and exceptionally livable space, where historic charm and modern updates come together in a truly special setting. The open-concept main living area features a spacious Great Room with an inviting fireplace, a generous Dining Area, and an updated Kitchen complete with new cabinetry, appliances, and a charming built-in dinette with seating. A dramatic wall of windows fills the space with natural light and overlooks the expansive bluestone patio and pergola, peaceful lily pond, and picturesque views of the original stone cottage. The main level offers four Bedrooms, two with en suite full Baths, and an additional full Bath and half Bath. A light-filled hallway lined with large windows leads to a comfortable Family Room, Laundry Room, Utility Room, and Safe Room. The second floor is dedicated to an impressive Primary Suite featuring a fireplace, newly added full Bath, three large walk-in closets, an Exercise Room, and a private Office—creating a spacious and serene retreat. Extensive upgrades include a new metal roof, whole home generator, geothermal heating and cooling, structured wiring and camera system, and dual 100-gallon water heaters. Please see the numerous other updates on the attached list. Additional highlights include a spacious two-car attached Garage and generous attic storage. Rich in character, thoughtfully updated, and designed for everyday living and entertaining, this exceptional property offers a rare opportunity to own a home unlike any other.

269 Cassidy Ave, Lexington

$314,000

Seller will consider mid-term rental. In the heart of Chevy Chase is the most charming condo in a beautiful 4 plex building. On the first floor, this unit features tall ceilings, hardwood floors, white walls, white woodwork and many large windows offering great natural light. The building was renovated mid 2023 and turned into 4, 2 Bedroom, 1 Bath condos. At that time the new white Kitchen with stainless appliances and abundant cabinetry was installed. The hardwood floors were refinished and a white Bathroom was installed. The Heat Pump was installed for each unit. The inviting Living Room has a programmable electric fireplace with heater and entire unit has new vinyl windows with shades that adjust from top and bottom. There are 2 Bedrooms that each attach to the Bathroom. The laundry includes a stackable washer & dryer and is adjacent to the Kitchen. The unfinished Basement features a lockable storage unit for each unit. The HOA fee covers exterior maintenance & insurance. There is a large parking area in back with one reserved space per unit. About 5,000 dollars worth of furniture will stay with the property.

2 Beds ⋅ 1 Baths ⋅ 26005178 MLS

Seller will consider mid-term rental. In the heart of Chevy Chase is the most charming condo in a beautiful 4 plex building. On the first floor, this unit features tall ceilings, hardwood floors, white walls, white woodwork and many large windows offering great natural light. The building was renovated mid 2023 and turned into 4, 2 Bedroom, 1 Bath condos. At that time the new white Kitchen with stainless appliances and abundant cabinetry was installed. The hardwood floors were refinished and a white Bathroom was installed. The Heat Pump was installed for each unit. The inviting Living Room has a programmable electric fireplace with heater and entire unit has new vinyl windows with shades that adjust from top and bottom. There are 2 Bedrooms that each attach to the Bathroom. The laundry includes a stackable washer & dryer and is adjacent to the Kitchen. The unfinished Basement features a lockable storage unit for each unit. The HOA fee covers exterior maintenance & insurance. There is a large parking area in back with one reserved space per unit. About 5,000 dollars worth of furniture will stay with the property.

1400 Fontaine Rd Unit 1, Lexington

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