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Very Cool Houses

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99 Fairway Drive South Burlington VT 05403

South Burlington, VT99 Fairway Drive

Price$1,100,000

Est. Mortgage: $/month

Pending

MLS Number 5087845

  • Residential Single Family
  • Full Bath 2
  • Address 99 Fairway Drive
  • Construction Existing
  • Bedrooms 3

Tucked along the 10th hole of prestigious Vermont National Country Club, this beautifully maintained townhome offers an exceptional blend of comfort, elegance, and location. Cherished by its original owners, the home has been lovingly cared for and thoughtfully enjoyed over the years, creating a warm and inviting atmosphere throughout. Filled with natural light and overlooking the golf course, the main level features an open-concept kitchen, dining, and living area designed for both everyday living and entertaining. The kitchen offers ample prep and cabinet space, while the living room is anchored by a cozy gas fireplace. A first-floor office provides the perfect spot for working from home. Upstairs, the spacious primary suite includes a large walk-in closet and private bath with a whirlpool tub, creating a comfortable retreat at the end of the day. Two additional bedrooms and a full bathroom complete the second floor. The partially finished basement adds valuable bonus space ideal for a media room, home gym, playroom, or guest overflow. Set within one of South Burlington's most sought-after neighborhoods, this special home combines peaceful golf course living with close proximity to local amenities, recreation, and everything the area has to offer!

Listed by Joe Villemaire of Rockstar Real Estate Collective

$
$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on May 28, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1844 Halladay Road Middlebury VT 05753

Middlebury, VT1844 Halladay Road

Price$1,100,000

Est. Mortgage: $/month

MLS Number 5091765

  • Residential Single Family
  • Full Bath 2
  • Address 1844 Halladay Road
  • Construction Existing
  • Bedrooms 4

The classic Vermont farmhouse is on the market! This iconic property also enjoys classic Vermont mountain views that will complete the package. Nestled onto the landscape, the residence is perched up off the road looking west over conserved land to the Adirondacks. This property calls to you with its wrap around porch and handsome details, to come take a look inside! The adjacent barn is part garage, part barn, with a large finished room at the end that is a fully insulated, heated studio space- complete with bathroom! Used for years by the current owners who are artists, but could also be a wonderful music space, home office or even potential guest quarters. The main house has a true Vermont mudroom- big enough for all of your gear- and the way most will enter your home. Once inside you will enjoy the large, eat in kitchen with wood fireplace and built in cabinetry, that enjoys those western views. Butternut from the property was used for most of the trim in the home! The living room is adjacent, and features wood floors and a wood stove that can heat the downstairs. A front parlour serves as another living room, and currently hosts the piano for musical gatherings. An office, powder room and laundry are also on this floor. The living spaces open up to the fabulous wrap around porch where you can lounge day or night to your heart's content. The gracious stairs bring you up to four bedrooms and 2 1/2 baths- enough room for you and your guests! Located just minutes to downtown Middlebury, but your own private oasis and land for gardening or animals. Come check out this beautiful home and make it yours!

Listed by Sarah Peluso of IPJ Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on May 28, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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700 Whittier Road Derby VT 05830

Derby, VT700 Whittier Road

Price$1,100,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5089915

  • Residential Single Family
  • Full Bath 2
  • Address 700 Whittier Road
  • Construction Existing
  • Bedrooms 3

Situated on 10.3 private acres in Vermont's scenic Northeast Kingdom, this exceptional hilltop property offers stunning views & a peaceful country setting. In addition to the 4500+ sq.ft. home is an impressive 44'x88' workshop/garage with RV hook ups. The home has been completely remodeled inside and out in recent years and showcases quality craftsmanship and high-end finishes throughout all three levels of living space. The main level welcomes you with an open-concept design featuring a stunning kitchen with quartz countertops, stainless steel appliances, pantry, dining area, and an expansive living room highlighted by soaring 19'+ ceilings & a wall of east facing windows. Also on the main level is a spacious bedroom suite complete with a walk-in closet and tiled ¾ bath and an additional 1/2 bath. Upstairs offers a laundry room, two full baths, & two additional bedrooms, including an impressive 600+ sq.ft. primary suite featuring a 10'x12' walk-in closet, oversized 6'x6' tiled shower, soaking tub, and double vanity. The walkout lower level provides additional living & entertaining space with a family room & wet bar, office, music/theater room, craft room, ¾ bath, & utility room. The property also includes a heated 30'x30' attached 2-bay garage and an incredible 44'x88'+ detached heated workshop with 15' ceilings, two 14'x14' overhead doors, an additional 12'x12' door, separate septic system, ¾ bath, 200-amp electrical service, heated office, Rotary lift, air compressor, & work bench. Enjoy the incredible outdoor living spaces from the expansive composite front and rear decks, fully enclosed gazebo, and stone patio with a propane fire pit, all perfectly positioned to take in the remarkable views. Additional features include an 18KW standby generator, seven mini-splits providing heat and air conditioning, Harvey windows and doors, radiant heated floors, and two RV hookup sites. A truly exceptional property offering the perfect balance of luxury, comfort, and privacy.

Listed by Jenna Flynn of Jim Campbell Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on May 28, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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6 Old Ridge Road Winhall VT 05340

Winhall, VT6 Old Ridge Road

Price$1,100,000

Est. Mortgage: $/month

MLS Number 5090234

  • Residential Single Family
  • Full Bath 2
  • Address 6 Old Ridge Road
  • Construction Existing
  • Bedrooms 5

Tucked into Stratton Mountain Resort's sought after High Meadow neighborhood, 6 Old Ridge Road offers the rare combination of substantial square footage, significant recent exterior improvements, and the opportunity to personalize the interior aesthetic to your own taste. Encompassing over 4,600 sq. ft. across three finished levels, this expansive mountain home is designed for gathering, relaxing, and enjoying all four seasons in Vermont. Recent exterior improvements have significantly enhanced the home's appearance and overall exterior presentation. Extensive work included reconstruction and upgrading of major exterior sections, along with new windows, roofing, trim, upgraded siding, exterior refinishing, and fresh paint. Complemented by a standing seam metal roof and updated exterior detailing, the home now offers a refreshed mountain exterior with a warm and inviting presence. Inside, the layout is exceptionally functional and inviting. The main level features an open kitchen, dining area, and vaulted living room with fireplace, along with a sunroom, screened porch, stone patio, and private primary suite. A mudroom with half bath off the attached two-car garage adds convenience for ski season and everyday living. Upstairs offers three additional bedrooms, a full bath with double vanity, and an airy loft overlook. The finished walkout lower level is built for entertaining and flexible living, featuring a spacious family room with wood stove and sliders, custom bar area, guest bedroom and bath, additional half bath, laundry, utility areas, and wide hallways throughout. Located just minutes from the slopes, golf course, village, and shuttle access, this is a rare opportunity to own a substantial Stratton mountain home with significant exterior improvements already completed, while still offering the chance to bring your own vision and style to the interior spaces.

Listed by Trent Stephens of Wohler Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on May 28, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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846 Weeks Hill Road Stowe VT 05672

Stowe, VT846 Weeks Hill Road

Price$1,100,000

Est. Mortgage: $/month

MLS Number 5074105

  • Residential Single Family
  • Full Bath 1
  • Address 846 Weeks Hill Road
  • Construction Existing
  • Bedrooms 4

This classic Vermont homestead offers income potential and exceptional utility in a highly desirable Stowe location. Set on a private and peaceful 3.24+/- acre parcel just 13 minutes from Stowe Mountain Resort and 4 minutes to the Village, this property presents a rare opportunity to live, work, and invest in one of the most sought-after locations in New England. The main residence is a 4-bedroom, 3-bath home offering solid bones, stunning wood craftsmanship and tremendous potential for personalization. With its stunning wide plank wood floors and rustic beams it provides an excellent canvas for those with vision looking to restore and reimagine their own Stowe home. In addition to the main house, the property includes a single garage and a two vehicle garage separating the main house from the two apartments which provide additional income and excellent rental or multigenerational living potential. A large gambrel-style structure with substantial garage space and ample parking below, is ideal for commercial vehicles, equipment, landscaping operations, or contractor use. Set back from the paved road, nestled in just enough woods for privacy with just enough open space for gardens or recreation, this Colonial-style home offers so much flexibility in an unbeatable location. Unwind to the soothing sounds of the meandering stream in the private backyard or venture down the bank at the rear of the property to your personal swimming hole. This property is exceptionally well-suited for a contractor, landscaper, tradesperson, or investor seeking to operate from home while generating rental income, all in a location that truly cannot be beat. Enjoy immediate access to world-class skiing, fine dining, recreation, and the vibrant Stowe lifestyle. Explore the limitless potential of this unique and versatile property in one of Vermont's most desirable destinations. Photo gallery contains both current and virtually re-imagined images. Also listed as Multi-Family MLS#5075502.

Listed by Justin Reyher of New England Landmark Realty LTD

$
$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on May 28, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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127 Wynnridge Drive Rutland Town VT 05701

Rutland Town, VT127 Wynnridge Drive

Price$1,099,000

Est. Mortgage: $/month

MLS Number 5038848

  • Residential Single Family
  • Full Bath 3
  • Address 127 Wynnridge Drive
  • Construction Existing
  • Bedrooms 4

Welcome to a home where serenity and style unite in perfect harmony. Situated in the exclusive Wynnridge subdivision of Rutland Town, which offers the advantage of school choice, this custom home boasts 5,400 sq. ft. of refined comfort and timeless craftsmanship. Impressive curb appeal featuring stone accents, lush landscaping, charming cobblestone walkway leading to a lovely entrance. Step into the soaring 17-foot vaulted foyer that invites elegance and warmth. The great room showcases cathedral ceilings, granite, a gas fireplace, and beautiful built-in bookshelves, while custom windows frame breathtaking mountain views. Glorious dining room. The eat-in kitchen is a delight, with rich wood cabinetry, granite countertops, and upscale appliances. Adjacent, the den offers a fireplace providing an ideal oasis for relaxation. A three-season porch and spacious deck create an inviting environment for summer enjoyment. The main-level primary suite is flooded with natural light and features a luxurious bathroom for private retreats. On the second floor, discover three additional bedrooms, two full baths, one en suite, and a versatile den for work or play. The lower walk-out level is perfect for guests or extended living needs, featuring a family room, a bonus room, and a bath. Mechanical amenities include a Buderus boiler, central air conditioning, a central vac., and a new whole-house generator. Located in one of Rutland Town's most coveted neighborhoods. Minutes to Skiing & Lakes.

Listed by Freddie Ann Bohlig of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on May 28, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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420 Steendom Lane Lyndon VT 05852

Lyndon, VT420 Steendom Lane

Price$1,099,000

Est. Mortgage: $/month

MLS Number 5089197

  • Residential Single Family
  • Full Bath 1
  • Address 420 Steendom Lane
  • Construction Existing
  • Bedrooms 2

Discover your private retreat on 114 acres of Vermont woodland, just 17 minutes from Burke Mountain and under 2 miles from Caledonia County Airport, where scenic foliage flights and flight training are offered. This 2-bedroom, 2-bath post-and-beam Cape blends rustic charm with modern comfort, offering both a serene lifestyle and proven income through Airbnb. The main level features wood flooring, a sunlit great room with stone hearth, built-in bookcases, and dining area. The kitchen includes new stainless-steel appliances, gas range, and opens to a cozy living room with wood stove. A flexible office/guest room and a tiled ¾ bath with heated floors, laundry, and cold plunge tub complete the first floor. Upstairs, the primary suite offers a large walk-in closet, dual vanity, and tub/shower, while a guest bedroom has its own spacious closet. Outdoor living shines; relax on the porch overlooking the pond and footbridge, refresh in private outdoor showers, or enjoy the nearby wood-fired sauna. A firepit with benches, multiple campsites, and a dedicated RV site with hookups and deck create endless opportunities for hosting or rental income. A massive two-story garage/workshop with four bay doors accommodates equipment of almost any size. Energy independence is ensured with a solar array, Briggs & Stratton battery bank, and enclosed propane generator. With trails for year-round exploration, this property is both a tranquil homestead and an income-generating investment.

Listed by Adam Cross of Flex Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on May 28, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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471 Crosstown Road Berlin VT 05602

Berlin, VT471 Crosstown Road

Price$1,099,000

Est. Mortgage: $/month

MLS Number 5092762

  • Residential Single Family
  • Full Bath 2
  • Address 471 Crosstown Road
  • Construction Existing
  • Bedrooms 5

Discover an extraordinary Vermont retreat offering over 5,000 square feet of living space on more than 10 private acres. This fully furnished 5-bedroom, 4-bathroom property combines luxury amenities, exceptional income potential, and a peaceful setting, all just 30 minutes from Stowe. Designed to accommodate large groups while maintaining comfort and privacy, the home features expansive gathering spaces and an impressive lineup of resort-style amenities. Enjoy year round recreation with the indoor pool, relax in the hot tub after a day of adventure, or unwind in one of two private saunas. Being offered fully furnished, this turnkey property is ready for immediate enjoyment or continued rental operation. In addition to its appeal as a private residence or vacation home, the property has been a highly successful short term rental, making it an exceptional investment opportunity. Guests are drawn to the home's unique amenities, spacious accommodations, and convenient location near some of Vermont's most popular attractions. Set on over 10 acres, the property offers the perfect balance of privacy and accessibility. Enjoy the tranquility of a secluded Vermont setting while remaining just 30 minutes from Stowe's renowned skiing, hiking, dining, and year round recreation. Whether you're looking for a luxury mountain retreat, an income producing investment property, or both, this rare offering delivers space, privacy, and an unmatched collection of amenities in one remarkable package.

Listed by Maura O'Neill of Ridgeline Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on May 28, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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3642 Lime Kiln Road Monkton VT 05472

Monkton, VT3642 Lime Kiln Road

Price$1,095,000

Est. Mortgage: $/month

MLS Number 5084400

  • Residential Single Family
  • Full Bath 1
  • Address 3642 Lime Kiln Road
  • Construction Existing
  • Bedrooms 2

Set on 116 acres of rolling Vermont countryside with sweeping views and frontage along Little Otter Creek, this well-equipped horse farm offers both functionality and future potential. Approximately 30 acres are fenced and ready for horses or livestock, complemented by an impressive barn featuring five oversized 2" hemlock stalls-built for durability-even accommodating larger breeds, along with five versatile lean-tos, a hayloft with capacity for up to 1,000 bales, a spacious paddock, and a dedicated mare-and-foal stall. Additional outbuildings include a large equipment garage and gardening shed. The updated 2-bedroom, 1.5-bath home showcases a new kitchen with butcher block counters and a walk-in pantry, renovated baths, new flooring, fresh interior paint, a sun-filled wrap-around porch, and a walkout basement. A seller concession for kitchen appliances adds convenience, while a second permitted lot within the acreage offers valuable building potential. Ideally located in southern Monkton, just 10 minutes to Vergennes, 15 to Middlebury, and 45 to Burlington.

Listed by Lipkin Audette Team of Coldwell Banker Hickok and Boardman

$
$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on May 28, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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833 Shaw Mansion Road Waterbury VT 05677

Waterbury, VT833 Shaw Mansion Road

Price$1,095,000

Est. Mortgage: $/month

MLS Number 5065807

  • Residential Single Family
  • Full Bath 3
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4

Experience the perfect balance of Vermont serenity and modern sophistication in this stunning 4-bedroom, 4-bath home set on 10.09 private acres of open meadows and peaceful woodland with breathtaking views of the Worcester Mountain Range. Sunlight pours through the abundant windows and doors, highlighting the warm maple floors, elegant stone wood-burning fireplace, and the spacious kitchen featuring birch cabinetry, granite countertops, and ample room for gathering. The primary suite is a true retreat, complete with a custom walk-in closet with built-in shelving and a renovated spa-inspired bath showcasing a double vanity, tiled shower, and oversized soaking tub-a serene escape to unwind and enjoy the timeless tranquility of Vermont's classic landscape. The lower level offers even more flexible living space with a large recreation room perfect for a gym, game room, or media lounge, plus two additional rooms for guests or home offices and a full bathroom. The exterior access to the basement adds convenience & flexibility. Step outside to enjoy the stone patio, covered porches, and relaxing hot tub surrounded by the sights and sounds of nature. Freshly painted and move-in ready, this home perfectly blends privacy, natural beauty, and accessibility-just minutes from world-class skiing, scenic hiking trails, the Waterbury Reservoir, and Waterbury's charming downtown shops and dining. Explore the 3D tour and cinematic video to experience this exceptional home firsthand!

Listed by Valerie Guilmette of BHHS Vermont Realty Group/Waterbury

$
$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on May 28, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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235 Winter Haven Road Shelburne VT 05482

Shelburne, VT235 Winter Haven Road

Price$1,089,375

Est. Mortgage: $/month

Pending

MLS Number 5080375

  • Residential Single Family
  • Full Bath 3
  • Construction Existing
  • Bedrooms 4
  • Bathroom 5

Perched high at the end of a cul-de-sac with beautiful views of Shelburne Bay, this custom-built, 4-bedroom, 4.5-bath home blends comfort, space, and thoughtful design. An expansive wrap-around porch welcomes you in, featuring a creative removable screened section on the west side - perfect for relaxing while taking in the lake views. Inside, pristine hardwood floors and 9-foot ceilings create a bright, inviting feel with a wonderful balance of open living spaces and cozy gathering areas. The front entry is flanked by a fire-lit living room and a bright family room that flows seamlessly into the beautifully updated kitchen. The kitchen features white cabinetry with large storage drawers, granite countertops, stainless steel appliances, a center island, wine storage, pantry closet, and a spacious breakfast nook. Just off the kitchen is a formal dining room with built-ins-ideal for entertaining. A first-floor office/laundry room add exceptional functionality, recently updated with new flooring, custom cabinets, along with an additional walk-in pantry. Upstairs are four bedrooms and three baths, including a spacious primary suite with a walk-in closet and private bath featuring a soaking tub, separate shower, and double vanity. The finished lower level offers a large mudroom off the two-car garage with EV Charger, a generous craft or recreational room, full bath, and an impressive media room with built-in speakers. Step outside to the porch and patio to enjoy the ever-changing scenery of Shelburne Bay-just minutes from Shelburne Village or Downtown Burlington. Welcome home!

Listed by Deborah Hanley of Coldwell Banker Hickok and Boardman

$
$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on May 28, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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86 Wildwood Court Shelburne VT 05482

Shelburne, VT86 Wildwood Court

Price$1,089,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5092138

  • Residential Single Family
  • Full Bath 2
  • Address 86 Wildwood Court
  • Construction Existing
  • Bedrooms 3

Tucked away on over 3 private acres just minutes from Shelburne Village, this elegant custom home offers the perfect blend of refined living, thoughtful updates, and exceptional outdoor space with beautiful seasonal sunset and Adirondack views! Meticulously maintained, the 3-bedroom, 3-bath home features a welcoming open floor plan ideal for everyday living and entertaining alike. The refreshed gourmet kitchen is the heart of the home, showcasing white cabinetry, stainless-steel appliances, granite countertops, stylish tile backsplash, and inviting dining and sitting areas surrounded by dramatic floor-to-ceiling windows overlooking the peaceful setting. Just off the kitchen a fabulous screened porch provides the perfect spot for relaxing, dining, or entertaining outdoors. The kitchen flows seamlessly into the expansive living room highlighted by soaring vaulted ceilings, abundant south-facing windows, and a cozy gas fireplace. A formal dining room currently serves as an intimate sitting room, offering additional flexibility. Privately situated on the main level, the spacious primary suite features an en-suite bathroom with a custom subway-tiled frameless glass shower and soaking tub. Upstairs are two bright bedrooms with walk-in closets, a full bath, and a large unfinished space above the garage offering excellent potential for expansion, recreation, or a studio. The partially finished lower level adds nearly 1,100 square feet of living space, including a generous bonus room, office, and workshop. Outside, this remarkable property sits on 3.08 private acres with a partially fenced yard, beautiful gardens and landscaping, a bluestone terrace, new Trex deck, and beautiful stone walls, including a new stone wall by the home and historic walls along the roadway. Additional highlights include an updated roof and owned solar panels. Truly a special place to call home!

Listed by Deborah Hanley of Coldwell Banker Hickok and Boardman

$
$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on May 28, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

Broker Reciprocity 

Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated June 8, 2026 12:09 PM EDT